Penny Barber
I’ve been enjoying keeping you all locked up and I just can’t resist the urge to tease you during your morning diaper change. I’m mean, but sweet, baby-talking to you and reminding you that I’m in charge of you, your diapers, and your cute, little penis. As I remind you that you don’t have to worry about grownup things like tits and ass, I start stripping down and playing with my own tits and ass. I vibrate myself in my soft, pink panties, seeing how hard I can make you in your diaper. Maybe if you’re a good widdle boy I’ll let you nurse on my clit. MAYBE
chastity devices, diaper, diaper discipline, diaper fetish, key holding & chastity
Download link ----> Diaper Change Chastity Tease - June 02, 2017 - 1.75 GB
A Penny Barber Fantasy. Watch the full clip in my store! XOX Follow me on Twitter.com/PamperedPenny
milf, diaper, diaper discipline, diaper fetish, femdom pov
Download link ----> FREE You Belong in Diapers - December 09, 2021 - 222.45 MB
I was thinking it would be fun to humiliate you in a big, puffy diaper but then I had an even better idea. It would be so much more humiliating to use little dolly diapers for your little dolly dick. The adorably tiny diapers are the perfect size for your sweet little thingy. Just relax and enjoy having your cute little cock babied while you stare at my nice big tits. Once I get that little stiffy all powdered, lotioned, and taped up in its dolly diaper, I may even get out the vibrator as a little treat. These are definitely way more embarrassing than the big crinkly diapers but I bet you make a creamy in them just as fast.
femdom, sph, cock tease, diaper fetish, imposed ejaculations
Download link ----> Tiny Diapers for Your Tiny Cock - June 19, 2020 - 547.85 MB
I come in the interview for a babysitter job, but I don’t exactly look like your other applicants. I’m wearing a hot pink bodysuit, hot pants, and thigh high stockings. I talk about how I usually work nights and am usually really good with people. You’re not really sure what to ask me in the audition—er, interview. You try to focus on what I’m saying, but my breasts are straining against my thin bodysuit, I’m clearly not wearing a bra, and my shorts are practically panties.
Then you catch me saying something about how I have experience treating people like babies, even if I don’t have any actual experience babysitting. You ask what I mean. I offer to show you! But you’re going to have to get undressed in order to experience my diapering skills. I slowly strip you and my voice changes, becoming softer and sexier. I seduce you into diapers, trapping you just where I want you and reducing you to a widdle babie.
That’s when I notice that being diapered apparently gives you a stiffy! Would you like me to keep going? Well, it’s going to cost you, because this doesn’t feel like an audition anymore. It feels like I got the job—and I make a lot more doing this than you were offering for babysitting. I start teasing my nipple with a rattle while I tell you that maybe you should crawl over to your pants and get your wallet. You’re so horny that you’re ready to cum in a diaper, which you would never have thought possible! You just can’t keep yourself from handing over your hard-earned cash to continue the experience.
I strip out of my clothes, giving you a view of my big, round ass and my gorgeous tits. I start telling you how my diaper fetish led me to just sort of fall into this as I show you my pussy. Now, let me show you the special way that I like to put powder on the babie. I dirty talk to you as I ride your diaper until you have a truly embarrassing orgasm. Now that we’ve dealt with that pesky erection you’re free to wet your diaper, aren’t you? And that’s what’s going to make ME cum.
I bet you want to get out of that wet, dummy diaper, don’t you? Well, I want some more money. Diapers are expensive, as are naked women who will change you. Of course the babie doesn’t take off his own diaper. No more? Oh. Well, I guess you’re just going to have to stay in that diaper until your next paycheck comes
diaper fetish, money fetish, taboo, adult babies
Download link ----> Stripper ABDL Babysitter - February 27, 2017 - 1.72 GB
Mom helps you to be an obedient boy and you always enjoy our wanking sessions more when you are nice and comfortable beforehand. As long as you stroke it exactly like I tell you, then you will get to see Mom’s big beautiful breasts before your thingy pops. I know you want to rush to your countdown and get that special feeling but first you have to show me that you can follow directions about how to touch yourself. One hands or two, slow or fast, just follow along because Mommy knows your cock best.
milf, joi, big tits, taboo, mommy roleplay
Download link ----> Sweet JOI With Mom's Breasts - April 22, 2019 - 716.55 MB
Watch the full clip in my store. XOX
feet, milf, barefoot, pov sex, mommy roleplay
Download link ----> FREE Before You Go to College - March 05, 2021 - 144.74 MB
I am so proud of the strapping young man you have become but you will need more than good looks and a winning personality to be a success. That’s why I am implementing a sexual reward system to make sure your academic record matches your potential.
We are going to start off with one A grade equaling one blowjob but I think you will do much better than that. Especially after you understand the entire incentive structure. If you can get to peak academic performance then I will become your own personal Mommy Slut. You will be able to spank my big round ass or even fuck it, whenever you want. You can make rules for when I am allowed to cum or what I am allowed to wear. It will be like having your own personal MILF fuck toy that you can treat however you like. Only if you get those perfect grades, though. Would you like to see a little sample just to prove how far I am willing to go to make sure you get straight A grades?
milf, anal masturbation, submissive sluts, taboo, mommy roleplay
Download link ----> Mom Gives You Sexual Rewards - January 12, 2020 - 604.3 MB
You’re in diapers whether you like it or not, completely. But it isn’t all bad. I’m going to show you just how sensual being my widdle diaper boy can be, but giving you a warm, soapy enema and sucking your cock silly! Plastic pants will ensure that you don’t make a mess as I plop you down in the tub and tease you with my curvy body, bouncing my big breasts and round ass on your erection. Will you be able to maintain your assertion that you’re a big boy as you’re bombarded by the bizarre mix of humiliation and sex? Or will you succumb to being my diapered plaything, completely exposed and under my control?
diaper, diaper discipline, diaper fetish, enema, nurse
Download link ----> Rx: Diaper, Enema, Blowjob - October 18, 2020 - 1.76 GB
It was so fun to go out as Batgirl, and you looked GREAT as Batman. You fill out that costume nicely, sweetie, but Step-Mommy could still take you in a fight. Let’s go! Did you get an erection from wrestling with me?! It’s sooo…big. Straddling you while we’re dressed like this really turns me on, honey. I know we should’t, but Step-Mommy is going to show you her big tits and fat, round ass, and you’re going to show her that huge cock of yours. I’m going to suck your dick and get it as hard as possible before I slide you into my eager, wet pussy. After I ride you to a screaming orgasm, I drop the cape and let you give it to me from behind until you come deep inside of Step-Mommy. We can do this again, but you have to keep it a secret, okay, my little hero? XOXO
cream pie, costume, pov sex, superheroines, taboo
Download link ----> BatMommy Takes Your Costumed Cock - October 20, 2021 - 3.31 GB
Smells like somebody is burning something besides firewood wood over. I knew my darling boy couldn't go away to camp without getting into trouble so that is why I decided to be a chaperone on this trip. Now if you do not want me report this to the head counselor you better drop that J and grab your D. I want to watch you cum for me right here in the great outdoors. I don't care if it is embarrassing, should have thought of that before you let your Mom catch you smoking.
I am willing to help you pop before the group hike though. I bet the sight of my soft tits and big round ass exposed out in the wild will makes you want to stroke for me. Don't you want to see your Mom's wet pussy glistening in the sunshine ?
milf, public nudity, jerk off instruction, taboo, mommy roleplay
Download link ----> Wanking In The Woods With Mom - July 21, 2019 - 541.54 MB
Why did the little cucky boy run away from his babysitter after bath time? Are you embarrassed to get diapered by me or is there another reason you ran off to your Mommy's room all naked? I wonder if it has anything to do with the pair of panties you are trying to hide behind your back. It's so cute that you still want to sniff your wife's dirty panties even though she has sex with other men and makes you wear diapers at night.
I don't think your Mommy/wife would be very happy about you running away from your babysitter to play with her panties instead of waiting patiently to be diapered like a good boy. I wonder what she will do to the big baby when she finds her panties all sticky and your diaper all creamy. Oh don't worry they both will be before I am done with you tonight, diaper boy.
handjobs, cuckolding, diaper fetish, panty fetish, taboo
Download link ----> Cuckysitter Loves Teasing Diaper Boy - June 21, 2019 - 464.9 MB
Your father finally had me served with divorce papers, so you have a very tough decision to make: do you want to live with me or with your dad? You show me exactly where your loyalties lie with a 90 minute fuck fest on our white leather couch. We both let go: rutting, licking, sucking, and moaning the afternoon away. In the end, I don’t care if your father takes the house, the car, and all our savings as long as I get you.
This is a semi-POV shoot with Troy Francisco. He’s a really passionate lay anyway who prioritizes female orgasms, but I’d also been wanting to get my hands on him for a while, so this is A LOT OF SEX. Blowjobs, fingering, rimming, pussy-licking, fucking, and of course if you know me, you know how much I love hand jobs! In the end, Troy comes (you come) while being stroked between Mommy’s big, soft breasts, erupting and giving me quite a show!
milf, big tits, older woman / younger man ., taboo, mommy roleplay
Download link ----> Mommy's Getting Divorced - May 24, 2021 - 4.49 GB
This is the moment we’ve been working towards for so many years. I open and read your acceptance letter and…you got in! I prepared something special to celebrate this moment. Can you guess what it is, sweetie? Recounting all the sacrifices you made to accomplish this, I slowly remove my conservative dress to reveal the stunning shining lingerie I’ve been saving just for you. Mommy is going to make-up for ALL of the activities you missed being her perfect little go getter. I lavish you with praise as I get on my knees and take your beautiful cock in my proud and eager mouth. Tenderly kissing, licking, and sucking your manhood makes Mommy soooo excited. Sliding your perfect dick between my big soft tits, I tell you that Mommy will give you ANYTHING you want! You pick my pussy and fuck me from behind like the stud you are. After coming harder than I’ve ever come before, I let my hair down and ride you as hard as I can, coming again and again until you tell me you want to finish on my big tits. You give Mommy the biggest load of cum I’ve ever seen and I rub it all over my breasts before licking it off of my hand.
Mommy’s rewards will always be the sweetest, big boy. XOXO
pov sex, taboo, mommy roleplay, pov blowjob, cum on tits
Download link ----> Mommy's Sweet Rewards - January 28, 2022 - 4.52 GB
I catch my naughty little step-son sneaking around my room and finally confront him about playing in my panty drawer! I saw him with his hands down his pants in here once already and I suspect he has been messing with the old baby things stored in the attic. Sammy must have already been feeling guilty about being such a little pervert, because he starts begging to be punished almost immediately!
I am more than happy to provide the correction he needs, starting with a belt spanking on his bare bottom. Turning Sam’s little butt nice and red is just a warm-up to his real punishment though. If he is so interested in panties and diapers then maybe the wittle baby does not need to be wearing big boy pants at all! Until Sam earns back some big boy privileges he can expect to be diapered 24/7 and made to nurse whenever Mommy commands.
role play, diaper discipline, female domination, spanking f/m, tit worship
Download link ----> Spankings & Diapers For Sneaky Step-Son - December 07, 2018 - 924.21 MB
Seems that Mommy tried to get into a dress that was a little too tight around the shoulders and now I’m STUCK! Unable to get into or out of the dress, I really need your help sweetie. Don’t worry about the box of sex toys on my bed or the kinky panties I’m wearing. Please just help me out! I know it’s so easy to explore Mommy’s pussy and even see what one of my orgasms feels like on your cock, but I will absolutely ground you if you don’t stop IMMEDIATELY…after I cum a few more times.
milf, humiliation, pov sex, stuck, mommy roleplay
Download link ----> Mommy Gets Stuck and Fucked - January 29, 2021 - 3.02 GB
I really, really need a diaper change, Daddy. I am totally soaked and I am afraid my little skirt is going to get wet if you don't change my diaper soon. I will do anything to earn a fresh diaper. A blowjob seems like a fair trade if that's what you want.
Uh oh, I think your cock is too big to fit in my mouth, Daddy. I am trying to be a good diaper girl but it is just so huge. I guess you are just going to have to fuck my pussy on top of my wet diaper.
blowjob, big dicks, daddys girl, diaper fetish, dildo fucking
Download link ----> Begging Daddy for a Diaper Change - January 31, 2020 - 638.99 MB
Good morning, sir, rise and shine. Looks like a certain business baby absolutely soaked his overnight diaper. We better get you changed fast or you might be late for your first meetings. I was thinking about letting you wear some thinner diapers so you could be more discrete today but I am not sure that will be safe for my heavy wetting boss. Can you imagine if you soaked through to your trousers during a presentation?
I think you need something thick, and crinkly with a liner added for extra protection. I know you are only being fussy during your diaper change so I will play with that little stiffy. I might be able to squeeze in time to help you creamy really quick but I definitely won’t have time to put you in a fresh diaper afterward.
diaper fetish, office domination, taboo, adult babies
Download link ----> Secretary Loves Playing Mommy for You - December 27, 2019 - 634.16 MB
I guess somebody may have had a little more to fun than he could handle last night. Does Mommy need to help her hungover little man get himself sorted out? Oh wow, looks like your friends may have had a little fun with you last night because you are covered in sharpie. Now you know what can happen when you have too many. They even wrote on your adorable cock and balls!
Of course I cannot leave you with hearts drawn all over your penis and also of course you start to get hard as soon as I try to wipe off your dick. Maybe a nice, relaxing orgasm from Mommy will help your forget all about those means friends and your nasty hangover. It is only fair that if I have to clean your cock that I get to suck it too
blowjob, milf, role play, pov sex, taboo
Download link ----> Mommy Cleans You Up And Sucks You Off - January 27, 2019 - 1.76 GB
I have always been your biggest fan, Batman, and I am just so grateful to meet you. I would do anything to become your new Batgirl and I mean anything. All of my holes are yours to use and I would consider it the highest honor to have you cum on my face. Once I put the old Batgirl in her place then I hope you will let me have that sweet Batcock all to myself.
big loads, big tits, cosplay, pov sex, superheroines
Download link ----> Becoming Batgirl to Fuck Batman - January 05, 2020 - 657.68 MB
Oh, honey! Mommy is sooo glad you’re home. There’s something I’ve been meaning to ask you since your dad left and — now that I’ve had some liquid courage — I’m ready to just ask: would you satisfy Mommy sexually for your allowance instead of doing chores? Let’s start small. I’ve caught you staring at my big tits before, so why don’t you take this first bill from my cleavage and let me tell you how to make them feel good? You watch me tease my nipples with ice before I take out a twenty and tell you take your cock out. It’s so beautiful that I can’t help but worship it with my hands and tits. Finally a pull out a hundred and have you masturbate with me until I’m ready to take your perfect dick in my aching pussy. You give it to Mommy nice and hard, making me cum as you fill me with your jizz.
I think you’re going to enjoy earning your allowance a lot more from now on. XOXO
cream pie, dirty talking, embarrassment, pov sex, taboo
Download link ----> Earning Your Allowance - January 14, 2022 - 4.61 GB
Good morning, sweetie! I got up early to make you breakfast since you have such a big day of activities ahead of you. Are you alright? You have the strangest expression on your face. Wait — do you have an erection?! What’s that from? There is nothing wrong with my bikini. It’s comfortable and matches my apron. Okay, since it’s my fault you’re all hard, I’ll take care of it for you. Let me strip out of this tiny little swimsuit, and then give your big erection a nice blowjob. Mommy plays with her pussy, teasing you until you’re ready to cum all over that breakfast I made you. I don’t want it to go to waste, though. Why don’t you go get ready while Mommy finishes these cum-soaked pancakes?
milf, cum in mouth, taboo, micro bikini, pov blowjob
Download link ----> Very Inappropriate Breakfast With Mommy - July 28, 2021 - 2.85 GB
Watch the full clip in my store! XOX Follow me on Twitter.com/PamperedPenny
pov, milf, big tits, taboo, caught
Download link ----> FREE Mommy Catches You, and Helps - December 02, 2021 - 224.46 MB
It’s BBQ season again! That means I get to tease and torment you at all the family gatherings, slinking around in a slutty little bikini and making sure that you see my tits, ass, and FEET, adorned with sexy, little gold toe rings and a sparkly anklet. Auntie’s feet really do drive you wild, don’t they? And I bet your uptight little wife doesn’t use hers to stroke you off or to tantalize you, does she? I won’t tell that we cheated if you don’t. We sneak inside for a stealthy suck, stroke, and fuck. I hope we don’t get caught, but I also want your huge cock, even if you are my nephew. I use my whole body to please you, gushing over your gorgeous, gargantuan penis. Thank god you manage to pump a load of cum into my tight, taboo pussy before your wife comes looking for you. We quickly dress again and you go back to your wife as I go back to my husband, your bountiful semen still dripping out of my sex.
feet, milf, bikini, footjobs, taboo
Download link ----> Aunt's Sexy Summer Footjob - September 16, 2022 - 4.23 GB
I know these diapers are embarrassingly babysish but they were the only ones I could find big enough for you. I wish there was another way to deal with your bedwetting but I think it is time to accept that you need diapers. It won't be so bad, no one will see you in them besides me and they are really very soft. You might even like it. If you don't believe me then maybe I will just show you that diapers can feel good.
You can watch while I strip down, powder my bare bottom, and tape myself into one of these diapers that, I will admit, are a little embarrassing. If you promise to let me put you in one next then I promise to show you some funthings you can do in your diaper. Your bed gets to stay dry and you will get to feel really, really good in your cute little bottom and on your adorable thingy.
diaper, diaper fetish, mommy roleplay
Download link ----> Step-Mommy Diapers Herself and then You - September 04, 2020 - 561.03 MB
I am very happy about your report card but it is silly that you think I will believe that dirty story about your tutor. Maybe I should call Ella right now and ask her if she really got naked and sucked your cock to help you study harder.
Well, that phone conversation did not go the way I expected. I certainly can’t argue with the results of her sexual reward system though. I suppose if blowjobs are the best way to motivate you then it must be Mom’s turn to strip naked and suck your cock.
milf, big tits, blow jobs, taboo, mommy roleplay
Download link ----> Mom Motivates You with Blowjobs - November 24, 2019 - 684.33 MB
Okay, sweetie, I’ll stay home sick from work if you promise to take care of me. I ask you to grab mommy some blue cold medicine and something to nap in. You pour from the wrong bottle—which I take without checking—and bring me some slutty lingerie instead of pajamas. I catch you watching me change, but am too tired reprimand you. You offer to watch over me as I nap and, shortly after I close my eyes, you notice me begin to moan softly and grind my hips. Slipping my hand between my legs, I masturbate in front of you to a powerful orgasm that wakes me up.
I’m a little embarrassed, but I’m even more excited. Maybe this is the cold medicine talking, but Mommy really wants your fat cock! You whip it out and I eagerly suck and titty-fuck it while occasionally sniffling from my cold. I get sooo hot playing with your giant dick that I beg you to fuck my tight wet pussy until I come all over it. You ride mommy to several orgasms before pulling out and letting me suck the cum out of you.
Mommy sure hopes she didn’t get YOU sick. XOXO
pov, milf, pov sex, taboo, funny
Download link ----> Sick Mother Fucker - May 13, 2022 - 4.43 GB
Another day started with persistent little kisses all over my thighs but before I can even get my glasses on or even say "Good morning" I feel my legs spread open and my nightgown pulled down. My darling boy is getting a little too with his affections and his stiff young cock is so eager for pussy it is practically vibrating!
I make my warm pussy and even my tight ass available for him to use but he can be so rough! When I ask my special man to be gentle though, he just gives me a few spanks and tells me to be quiet. I guess I better get used to starting every day by getting thoroughly fucked and then covered in my son's cum!
anal, rough sex, role play, doggystyle, taboo
Download link ----> Making Mom His Reluctant Fucktoy - December 23, 2018 - 997.69 MB
I almost can’t believe that we finally got to do it. I mean, I’ve always thought you were hot, but I had no idea you would be so good in bed. So, would you like to stay the night? What do you mean you’d like to but you have to wear a diaper? Wow, you even brought some... Do you think I could…put it on you? It’s different and kind of exciting. As I figure it out, I notice your cock still glistening with my pussy juice. I suck you clean before I finish putting your diaper on. Then I slip into some lingerie and and tell you to come cuddle.
It’s the middle of the night when I wake you. This whole experience is turning me on again. Do you have any extras? Because I kind of want to…try one. You do and I spread my legs, revealing my still cummy pussy. You get me all diapered up and I can’t believe how horny I am. I masturbate over the diaper before begging you to rub yours against mine. I come hard while wearing it and reach down to touch yours when we’re finished. Was your diaper full of pee the entire time we were rubbing against each other? Well I suppose we need to get you changed then, dirty boy.
pov, diaper, diaper fetish, orgasms, pov sex
Download link ----> Diapered After Sex - February 18, 2022 - 4.58 GB
We honestly cannot believe a guy would go through all the trouble of bringing home two stacked older woman just to rest on the couch. Did our amazing tits intimidate you? Ohhh, I see. I guess I would also be scared of big breasted MILFs if my dick was that small.Well we actually suspect that a tiny cock is not your only embarrassing secret... judging by the wet spot on the couch and all the DIAPERS we found in your room. HA! You really did not have to be a scared little baby and avoid us all night. You might not be equipped for the threesome we were expecting but the two of us have lots of idea for fun things to do with a bedwetter with a itty bitty winkie that belongs in diapers.
milf, sph, big tits, diaper, diaper fetish
Download link ----> Bedwetter Teased By Busty MILFs - October 11, 2019 - 678.54 MB
I did not mean to walk in on your little photoshoot but since I am here, we may as well get some better dick pics for you. I can get it from angles that will make it look bigger but first let me make sure it is as hard as possible. I'll just get my tits out and play with your cock a little before we snap any more. You have a very nice dick, dear, and I just want to make sure you have some pictures that make you proud. I mean it really is very, very nice. Actually, sweetheart, I think your cock would look the best after it is has been freshly fucked.
handjobs, big tits, cock worship, taboo, mommy roleplay
Download link ----> Dick Pics With Mom - June 09, 2019 - 605.23 MB
You know I like to relax and catch up on my reading in our dungeon but you came sniffing around for some attention from Step-Mom anyway. I know you want me to play with that sweet cock of yours but you should know by now that I am not going to play nice. For every stroke or lick there has to be a smack or sting. I am happy to ride you until my wet pussy spasms all over your stiff dick but only after I tie your vulnerable balls to my bondage table.
I hope the pleasure is worth the pain but you will taking both for me, no matter what. If you want to play with Step-Mom then you better be ready to play rough.
milf, bondage, pov sex, mommy roleplay, goth
Download link ----> Kinky Sex with Goth Mom - May 30, 2020 - 464.6 MB
I was so surprised to get a phone call from your teacher that was not a glowing compliment. What has gotten you off track this semester? Sweetheart, being horny is normal and not an excuse for poor academic performance. What do you mean are horny for something “weird”? You can tell me and I promise I will do whatever I can to help you get your grades back up.
Wait, you want me to wear what? Stick that thing where? Oh goodness. Well, if dressing up in this slutty anime costume and wiggling my ass in your face with this plug in my hole is the only way to get you back to straight A’s, then I guess that is what I have to do.
milf, big tits, butt plug, taboo, mommy roleplay
Download link ----> Mom Plays Dress Up To Get Your Grades Up - August 04, 2019 - 550.35 MB
Good morning, sweetie! Mommy has been watching you rest and getting soooo turned on thinking about all the naughty things we’ll do together. Let’s start the day with a nice wet blowjob where you come in Mommy’s mouth. Then I’ll make YOU breakfast dressed only in my collar and an apron. I’m feeling too horny to wait for you to eat, so I masturbate to a squirting orgasm all over your food. I beg you to punish me with a thorough pussy pounding from your big dick while I clean up the mess. You give Mommy a delicious cream pie that gets all over the floor. After tidying up the kitchen, you join me in the bathroom where your Mommy-slave can properly wash your painfully erect penis with my big soapy tits and eager filthy mouth. You finish by showering me with cum while I masturbate to a screaming orgasm in the tub. I’m the luckiest sex slave in the whole world!
cream pie, milf, taboo, collars / leashes, cum on tits
Download link ----> Collared Mommy Sex Slave - August 12, 2021 - 3.13 GB
The idea of controlling my virile young son gets me so excited! You're going to be my little jerk off toy, stroking your cock just for me, looking at the porn that I choose, cumming where I say. Your new life is going to 100% revolve around impressing me with your thick loads, stroking for me as many times as you can every single day. Jerking off for Mommy is your new priority--before your job, school, and girlfriend. So take out your cock, and stark stroking to my full tits and fat MILF ass
milf, joi, jerk off instruction, masturbation encouragement, taboo
Download link ----> Mom's Cum Slave - June 10, 2018 - 1.82 GB
I am sure my special boy will get back on his feet in no time but if you want to move back in until your business takes off then there are going to be some rules you have to follow. First off, once a week you will go skinny dipping with your friends in the pool so Mommie can see from her bedroom window. Rule number two is that you have to put on a little jerkoff show for me once a day so Mommie can watch you cum. Lastly, I will be using your mouth however I please, whenever I please. Does that sound fair, sweetheart?
masturbation, lace/lingerie, fetish
Download link ----> Mommie's Cock Tax - April 04, 2016 - 597.53 MB
You’ve got a big date coming up with a super hot girl, but it’s gonna cost you! You ask me for an emergency increase in your allowance, but after a long day at work, I’m in no mood. Lucky for you I left my purse on the counter, but lucky for me I walk back in just in time to find you rooting around for my wallet.
I’m furious, but once you tell me what it’s for, I do calm down a little. In fact, maybe there’s something you can do to earn that money before your date. You see, I'm not just stressed over work. It’s been ages since I had a nice, thick, throbbing cock in my hungry pussy. If you fuck me like I desperately need to be fucked, I’ll happily give you a little cash.
I play with myself while sucking your gorgeous hard on, then lie back to take you deep inside of me. You make me feel amazing and bring out my inner slut, bending me over in the kitchen and fucking me hard like the horny slut I am. Too bad I gave all my cash to your sister earlier.
milf, pov sex, taboo, creampie, funny moments
Download link ----> Penny Barber - Mom Catches You Stealing - March 24, 2023 - 3.79 GB
Mommy suspects that you have been playing video games instead of masturbating like you’re supposed to, sweetie! You know if you don’t come regularly then your focus begins to suffer. Alright, let’s see if you can play without getting distracted. I slowly strip right next to you as you log into your game. As you play with your controller, Mommy plays with her big soft titties and sensitive wet pussy. You finally give up when I take out my vibrator and masturbate to a screaming orgasm. Having made my point, I take out your beautiful and achingly hard cock. You let me stroke it, lick it, and suck it until I beg you to fuck Mommy’s cock hungry pussy. After giving me the pounding I so desperately crave, you release all of your cum and cream pie Mommy’s greedy pussy. NOW I think you’ll be able to focus again, darling.
pov, garter & stockings, pov sex, taboo, pov blowjob
Download link ----> Mommy Knows Best - September 24, 2021 - 4.54 GB
When I get an almost too-good-to-be-true gig out in Las Vegas, it’s time to load up the car. (I can’t fly with all of my camera equipment.) But it’s a looooong drive! What’s a diaper girl to do? But it’s okay: Daddy suggests that he drive me—and keep me diapered the whole way!
So many questions come up. What if Daddy can’t get my diaper on quite right? What happens when we’re stuck in traffic and my diaper is overflowing—and I still have to pee? Will Daddy really give me that bottle full of his pee? Are diaper girls expected to share in driving duties? Was this a good idea?!
diaper, diaper fetish, pee, public outdoor, adult babies
Download link ----> Penny's Diapered Road Trip with Daddy - June 25, 2021 - 3.21 GB
Are you excited to cum for Mistress after being in your pretty pink chastity cage for so long? I have a little treat for my pantyboy's this time. I want you to put your hands behind your back first then I am going to let you smell every single pair of my dirty panties and even rub your little cocklette over the whole pile of panties! Aren't you the luckiest sissy in the world?
chastity devices, fetish
Download link ----> Sissy Panty Sniffer - January 21, 2016 - 776.15 MB
My stepdaughter Zara has had a real attitude problem lately. Her father and I have tried talking to her, but she insists on being snarky, not doing her homework, and hanging out with the wrong crowd. I come upon her texting her no-good friend Luna to come hang out. I’m sure that she hasn’t finished her homework yet, but I let it go and remind her that she’s supposed to fix her attitude.
Well, of course she hasn’t. When Luna comes over it’s nothing but sass and rude whisperings. I’ve had enough. It’s time for a diaper punishment! I strip Zara out of her little white dress and put her in a big, puffy diaper. She’s so tiny and cute that the diaper nearly engulfs her! Luna is shocked, but also amused. She laughs and points as I dress poor, sassy Zara in a humiliating sailor outfit and lock her into it with cuffs and a cute, white bondage belt with sweet, little roses. I even let Luna take a few pics on her phone to show to the kids at school tomorrow. Completely humiliated, Zara just stands there blushing and trying not to cry.
But Luna shouldn’t have been so sassy herself. Just as she’s mocking her friend for being in diapers, I inform her that I recently spoke to her Mommie, too, and that I have permission to apply my special brand of diaper punishment to her, too. I strip Luna down and put her in her own matching diaper. I may not have extra gear to lock her up (though I’ll certainly tell Luna’s Mommie where to buy a set), but I do the next best thing: I take all of Luna’s designer clothes away. So it’s naked or a diaper. No third option. Now it’s Zara’s turn to watch and giggle!
The girls are decidedly pouty about being stuck in diapers, so I give them a chance to get back the keys for Zara’s bondage. I tell her that if she wets her diaper, she can have the keys back, no problem. I make her stand in front of Luna and put my hand on her little diapered crotch so that I can feel her. Zara swallows her pride and manages to wet her diaper, right into Mommie’s hand. So I give her a set of keys—baby keys! Did she really think that she would get out of her punishment so easily? Of course not.
Rather than change Zara, I decide that I need a little retail therapy after dealing with two bratty girls. So I take the real keys, and all of Luna’s clothes, and head off, telling Zara to let her Daddie know that I’ll be home late
diaper, diaper discipline, diaper fetish, older woman / younger woman, taboo
Download link ----> Mommie Diapers Stepdaughter in front of - February 14, 2017 - 1.73 GB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
milf, pov sex, taboo, mommy roleplay, family
Download link ----> FREE Coming in Mommy's Pussy - August 19, 2022 - 95.16 MB
Your stupid American father has sent you to live with me in Paris, but that doesn?t mean that I have to do all this Mommy nonsense. You want breakfast? Stale cigarettes and leftover wine. You want to jerk off? No WiFi—only Mommy?s baguette-stuffed pussy. It?s a good thing you have a nice, fat cock for me to look at. I do love watching men, qu'est-ce que c'est?—make jerk off? As you stroke your big, American dick for Mommy, I masturbate feverishly, until I finally spill eau de pussy all over that baguette. Maybe having you live with me won?t be so bad after all, you spoiled-yet-handsome American brat.
milf, joi, squirting, taboo, mommy roleplay
Download link ----> French Mom Squirts as You Stroke - December 02, 2020 - 2.51 GB
Look, I’m sorry that I didn’t get you absolutely everything that you wanted for Christmas, but Mommy’s not made of money. Is there something you’d like besides that video game console? Seeing me naked. Very funny. Unless…you really want to. Naturally looking at my curvy body makes you nice and hard, even if I am your Mom. My long, flowing dark hair, big tits, and tiny waist would give any boy your age an erection. And it is quite an erection! Maybe there’s something that you can do for Mommy, and then I’ll buy you that stupid PS5…
Timestamps:
2:16 You ask Mom for sex
6:23 Stripping
7:46 Mommy shows you her crotchless panties
8:20 Mommy show you her pussy
11:26 Mom asks you see your cock
13:23 Mommy masturbates
18:07 Missionary sex
25:24 Doggy style sex
27:45 Simultaneous orgasm in Mommy’s pussy
28:30 Showing off your cream pie in my MILF pussy
milf, blackmail fantasy, pov sex, taboo, mommy roleplay
Download link ----> Fucking a PS5 Out of Mommy - January 05, 2021 - 4.17 GB
Have you noticed that I’ve been different since I started taking my new hormones? I feel like they’ve turned me into a bit of a bimbo. They’ve also made me soooo horny! Maybe…you should take one, too? It’s just that you’re kind of uptight when it comes to sex and I really want to tell you about my secrets fetish--big, puffy diapers!—and the other side effects of my hormones—a big, juicy futa cock that loves to be sucked…while you wear a diaper…and we’re dressed in sexy bimbo outfits. Look, just take the pill! It’s, like, totally worth it!
diaper, feminization, futa, futanari, sissification
Download link ----> May Cause Ditziness - December 13, 2020 - 4.53 GB
Sweetie, I’ve got just what you need to relax. I picked up a book on hypnotherapy! Just get comfortable while I guide you into a calm and suggestible trance. Fixate on my big full breasts and how they make you feel. Get so lost in my words and tits that you can’t help but be transformed into my little diapered toy. Suck your thumb for Mommy. Wear a diaper and a bib for Mommy. It makes me so wet to see you submit to Mommy. Watch me tease you and masturbate in front of you. I make your cock soooo hard in that diaper, darling, that you know you’ll come as soon as I tell you to. As I count down to our mutual orgasm, you feel all of my suggestions root themselves into your pliable mind. We come so hard together that you know you’ve become my perfect little diaper slave. Now let’s get you changed and ready for more training, precious. XOXO
pov, diaper, diaper discipline, diaper fetish, mesmerize
Download link ----> Mesmerized Into Diapers - November 19, 2021 - 4.61 GB
Find the full clip in my store! XO
pov, femdom, diaper, diaper discipline, diaper fetish
Download link ----> FREE Bonding With Mommy - July 08, 2021 - 154.79 MB
I do believe you that walking with an erection is uncomfortable but we really need to catch up to the rest of the group. I am sure you don't want your step-sister to walk back here and find out the family hike is delayed because you got a boner. Can't you just take care of it? You can jerk off this one time without porn. You young people today really are helpless without your phones.
Will it help if I show you my bare breasts? I think these big beautiful MILF tits should be more than enough to get you off. Ok fine, I will show you my thick round ass too. I don't believe you can't masturbate without seeing my naked pussy but I am tired of arguing. I will get naked for you but please try to cum before someone comes to see what is taking us so long.
public nudity, joi, big tits, taboo, mommy roleplay
Download link ----> Wanking in the Woods to Step-Mom - August 30, 2020 - 374.39 MB
This Valentine’s Day I have a real surprise for you honey. Are you ready? Here it is: I know about your little dominatrix girlfriend. But rather than cry about it, I’ve decided to take control of the situation. Apparently you like women who are in control, but if I’m really going to be in control, that means that I make the decisions. Instead of whips and chains and black leather, we’re going to be enjoying pink sissy dresses, fluffy diapers, and chastity! Because you’re not going to be just another fake sub chauvinistic pig. You’re going to be my sweet, padded, pink piggy plaything!
Includes: feminization, diapering, ABDL, bondage, humiliation, POV, chastity, butt plugs, prostate milking, and femdom.
diaper discipline, diaper fetish, femdom pov, sissy training
Download link ----> Valentines' Day Diaper Punishment - February 13, 2021 - 4.57 GB
Watch the full clip in my store. XO
pov, milf, pov sex, taboo, pov blowjob
Download link ----> FREE Spying on Auntie - May 06, 2021 - 180.99 MB
Follow me on Twitter @pamperedpenny
Follow me on Instagram @pampered_penny
Order a custom video [email protected]
XOXO
femdom, femdom pov, behind the scene
Download link ----> Get Your Wife into Femdom - September 10, 2017 - 1.75 GB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
milf, diaper, diaper discipline, diaper fetish, collars / leashes
Download link ----> FREE Earning Mommy's Collar - August 04, 2022 - 179.89 MB
I was actually feeling proud of little Sammy for how diligently he has been working on his science experiment but then I discovered that he was motivated by something other than academic ambition. The dirty brat was trying to build a mind control device and he planned to secretly test it on me for his own entertainment. I knew from the way he was always trying to look down my top or up skirts that it was not going to be some cute show where he made me quack like a duck.
I was proved right when he finally snuck up and blasted me with whatever gadget he had been constructing. Too bad I had already sabotaged it. I pretended to be totally under his control at first and sure enough, he ordered me to strip within his first few commands. He barely even tested my obedience or awareness before he was grabbing handfuls of my tits and proclaiming himself to be a genius. I let him live his perverted dream of having his step-mom as a mindless sex doll for a little longer before I snapped him over my knee and into his nightmare. From thinking he had absolute power over my body to begging me to stop spanking his bottom in less than two minutes. At least he will have some memories of seeing me naked to comfort him during the long months of chastity ahead.
milf, cock tease, magic control, spanking f/m, taboo
Download link ----> MILF Sex Trance Ends In Spanking - April 28, 2019 - 654.57 MB
I don't always hook-up on the first date, but I do always bring condoms and wear nice panties, just in case. My date for tonight must have a very different idea of bringing protection though because my hand definitely touches a diaper when I put it down his pants! He tries to make excuses and even run away but I make him expose that he wore training pants style pull-ups to our date! He admits he gets a naughty thrill from wearing the babyish underwear during dates but that he did not expect to actually take his pants off on the first date.
The little perv probably thought he could slink away in shame after his embarrassing confession but I am already pretty horny and also think the whole thing is kind of hilarious. Instead of kicking him out, I make him suck his thumb while I ride his cock and tease him with baby talk. I ask him humiliating questions about his diaper fetish, like if he wets the bed or if he would rather cum in my pussy or in his diaper. Not that I give the silly diaper boy a choice where his little thingy is going to wet.
diaper, diaper fetish, embarrassment, femdom sex
Download link ----> Diaper Fetish Exposed On First Date - March 29, 2019 - 762.84 MB
Look what I found in this old box in the garage: my school girl uniform! It looks kinda small, but…do you dare Mommy to try it on? I have had a few cocktails and I’m feeling really loose. Just promise not to tell your dad, okay? I make you close your eyes while I strip out of my clothes and try it on—you totally peek!—and it is indeed a bit small. You can see Mommy’s fat, round ass under the short plaid skirt. It’s such a tease that you flat out ask to see my panties! I’m feeling very persuadable, so I agree, showing off my sexy, pink thong. There’s something about wearing this that makes Mommy feel so…slutty. How about we do a little role-play? What does Mommy need to do to get out of detention? I’ll show you my tits, suck your cock, and even let you creampie my tight pussy! I can’t believe I’m doing this with my son, but it feels sooo good!
cream pie, pov sex, school uniform, taboo, mommy roleplay
Download link ----> Mommy Fucks You in Her School Uniform - July 05, 2021 - 3.93 GB
When your secretary quits out of the blue things start piling up. Luckily Mommy is willing to help out her little entrepreneur. I show up wearing a tight, low-cut dress, which is so distracting that you call me into your office and ask for…a massage. I think it’s a little odd, but I do want you to be relaxed for your big meeting later. That’s when you tell me what would really relax you: a blow job!
I strip out of my dress, down to just my high heels. I start to tease you with my big tits, long legs, and curvy body before I invite you to cum fill up Mommy’s mouth!
big boobs, milf, pov sex, secretary, taboo
Download link ----> Mom Is Your Cock-Sucking Secretary - November 22, 2018 - 1.82 GB
know why you always ask to be my lab partner, I mean everybody knows you have a crush on me. Another thing we all know about you is that you wet the bed. Did the little bedwetting baby think it was his widdle secret? The real reason I invited you into my room was not to work on our science project but to give you a special present so you know what I think of you. A nice, puffy baby diaper in just your size!
A diaper is really the only thing a bedwetter deserves to wear so I'm going to have to confiscate your nerd clothes. I don't know which is more pathetic, that you still wet the bed or that you got a tiny stiffy from being diapered and humiliated by the girl of your dreams! I bet I could make you cream your diaper with one glance at my amazing tits.
diaper discipline, diaper fetish, female domination, imposed ejaculations, school girl
Download link ----> Bedwetter Diapered By His Crush - February 22, 2019 - 844.13 MB
Did you say we were going to do something kinky today, Daddy? Diapers make me soooo horny. Watch me masturbate and wiggle and finger my ass to show you how wet I get just touching the pretty pink one I picked out. Once I get it on, it’s not long before I pee in it — which just excites me even more! I bring myself to orgasm after orgasm with my vibrator, pausing to melt ice on my big tits and to tell you how naughty I feel. I’m desperate to suck your dick, so I give you a bouncy blowjob while still wearing my wet diaper. After you come in my mouth, I rub it all over my body. This was all so dirty I have to masturbate one last time. Covered in you cum, with my pussy exposed over my wet diaper, I finger myself to a final squirting orgasm. That was just what I needed, Daddy!
diaper, diaper fetish, orgasms, squirting, pov blowjob
Download link ----> Diaper Sex - August 05, 2021 - 3.65 GB
You know I am not letting you ride in the car without a diaper, not after your little accident in the store the other day. Are you worried that someone might see your little thingy while you're getting diapered in the backseat? I suppose I could I take out my nice big breasts to distract from the little diaper boy getting his bottom powdered. I can't wait to tease and play with my little adult baby cutie on our car ride.
Do you feel all snug in your nice dry diapy? Well, that is a shame because now you have to pour this entire cold water bottle into your diaper. A cold, squishy diaper probably does not feel too good so you should probably pee to make it a warm, squishy diaper. Step-Mommy loves to squeeze your sweet little stiffy through your wet diaper. Do you think if I pulled over and took my tits out again you could make that soaked diaper nice and sticky for me?
public nudity, cock tease, diaper discipline, taboo, mommy roleplay
Download link ----> Creaming Your Diaper in the Car - September 25, 2020 - 539.43 MB
Were both completely naked while I baby talk to your cute little dick and pat it all over with the powder puff. I rub my big, sexy breasts against your erection and jerk you off with babie powder and babie oil, absolutely spoiling your cock. Then it’s time for your milking bib. I tie it around your cute little balls and cock to make sure that you only get cum on your bib and in your diaper. I stroke you nice and slow to start, teasing you with my hand and breasts. I talk dirty to you, reminding you that diaper changes are sexual and that you’re only allowed to cum in diapers. It isn’t long before you cum all over. I guess I’ve successfully trained you to be turned on by your diapers! I clean you up and finish diapering you—until you’re ready to make a creamy again. I’ll know when you’re ready because you’ll be sucking your thumb!
This is a fun, sexy clip where I just get to play with your cock. Ever wondered what it's like to be my boyfriend? Buy this clip and you'll know
diaper, diaper fetish, taboo, adult babies
Download link ----> Diapers are for Cum - February 28, 2017 - 1.74 GB
I've been conditioning you to be my cute widdle sissy baby in cloth diapers and plastic pants for a while, but did you know that I've also been conditioning your pretty little wife? I've implanted so many suggestions in her head that I can pretty much make her do whatever I want. Perhaps I should make her overcome with lust for me, or make her aroused by the idea of you wearing your thick, girly diapers. You'd love that, wouldn't you? Or is that just another suggestion that I've implanted in your head? I guess you'll never really know! But you will jerk off into your diaper while you watch your lesbian Mommies make out, then you'll nurse on our big, full breasts like the good widdle sissy baby I've conditioned you to be
diaper, diaper discipline, diaper fetish, sissy training, sissification
Download link ----> Therapist & Wife Sissify and Diaper You - June 22, 2018 - 1.82 GB
This video came out pixelated, so I can't post it for sale, but I thought it came out so well that I hate to throw it away. Hope you like it even though it isn't perfect!
Follow me on Twitter @pamperedpenny
diaper, diaper discipline, diaper fetish, taboo
Download link ----> Diapered for Your Big Date - June 11, 2018 - 1.84 GB
I hope you are excited for game night with Step-Mom. I was thinking maybe a few rounds of dirty Candyland? The rules are very simple. Each color card has a different sexual action that the player must perform. There is a color for taking off clothes, colors for touching yourself, and even one for getting to have an orgasm. I know you want to play any game where you get to stare at my big, full tits and jerk-off so I think we are both going to enjoy Strip Candyland tonight.
pov, milf, big tits, joi games, taboo
Download link ----> Strip Board Games with Step-Mom - April 26, 2020 - 720.58 MB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
strap-on, diaper discipline, diaper fetish, femdom pov, pegging
Download link ----> FREE Pegged & Pampered - August 26, 2022 - 201.39 MB
None of the other moms were down for a power walk, but I just know that I can convince my special boy to come along! After all, I know what you like: big tits, a fat ass, public masturbation, butt plugs, and S-E-X. You have to agree that all this power walking has really toned Mommy’s ass and thighs. Don’t you want to know how tight Mommy’s pussy get when she gets caught? Grab your sneakers and join me as I walk around the neighborhood, showing everyone what a little MILF slut I am!
pov, milf, public nudity, taboo
Download link ----> Mom Flashes & Fucks You Outside - September 02, 2022 - 4.45 GB
Ella and I cannot believe that a little dick brat like you cheated on women as hot as us. We also cannot believe how easy it was to turn you into our little diapered sissy plaything. From now on, we will be fucking each other and you will be dressed up in girly outfits and frilly plastic panties. You will be taking enemas for our amusement and downing bottles filled with our pee. If you are a very obedient little sissy baby we might just let you beg for the privilege of making a creamy in your squishy, soaked diapers.
sph, cuckolding, diaper discipline, enema, feminization
Download link ----> Sissy Baby Cheater with Ella Nova - June 25, 2020 - 581.94 MB
timer for two minutes and then I am going to stroke your cute little cock with baby oil as fast as I can. If you can last till the buzzer without shooting your load all over the place then you will get a special treat. If you can't control your little thingy like usual, then you are going to get diapered and put in some very embarrassing pink plastic pants. I know creaming yourself in less than two minutes is probably humiliating enough but little boys with no self-control belong in diapers anyway.
Just to make sure that you really earn that special treat, I will be wearing nothing except my pretty pink thong while I stroke that overeager little winkie of yours.
handjobs, cock tease, diaper discipline, humiliation
Download link ----> Diaper Challenge for PrematureEjaculator - February 28, 2020 - 661.79 MB
I am super nervous for our first date so of course the worst case scenario comes true. I totally soak my diaper right before you arrived. I am so embarrassed that I have to confess my deepest secret right away. I have to be diapered almost all the time and stressful situations ,like meeting up with my crush, always makes me wet myself.
I can't believe you are being so cool about this situation. Do you really want to watch me change my diaper? I guess that would be ok, if you really mean it. I thought starting my date with a wet diaper would be incredibly humiliating but diapering myself in front of you is actually really, really hot.
role play, diaper, diaper fetish, embarrassment
Download link ----> First Date Diaper Change - March 06, 2020 - 460.02 MB
After finding your sister’s panties in your bedroom, I decided to stake out your room and my suspicions were confirmed: you’re fucking your sister. But before I can make up my mind of what to do on the subject, I have a few tests to perform. I take out my notebook and proceed to measure how you respond to various visual sexual stimuli. Can you maintain eye contact while Mommy strokes her nipples? What happens if I strip down to my lingerie? Will you get hard? I conclude that it isn’t, in fact, your fault. You clearly have an overactive libido and, as your Mother, I really should be the one to deal with it. So, bring your erection over here and slip it into Mommy. I try not to enjoy it, but it isn’t long before I’m cumming all over your cock—just like your wanton slut of a sister did!
milf, older woman / younger man ., pov sex, taboo, mommy roleplay
Download link ----> Mommy Knows You Fuck Your Sister - March 01, 2021 - 3.6 GB
I got stood up yesterday, but I still had a pretty amazing time
milf, yoga pants, adult babies
Download link ----> Stood Up, but Still Fucked & Spoiled - February 06, 2017 - 1.74 GB
Now that your wife and I have you living full time as our diapered sissy baby, we think you need a part time nanny. Someone who will give you spankings, creamies, and diaper changes when your Mommies are busy. We thought the most humiliating choice to be your new sissy sitter would be your old secretary, Ella Nova, so she is on her way now. Can’t wait to show her that you have traded in board meetings and power suits for diaper wetting and frilly plastic panties. Do you think Ella will still have a crush on her old boss after the first time she cleans the pee-pee off your little sissy clitty during a diaper change? I bet she will be thrilled that she can just shut you up with a pretty pink pacifier after taking orders from you for years.
Maybe I will do the same thing that I did to your wife and use my powers of persuasion to turn Ella into my lesbian sex doll as well. I will be fucking all the women you used to lust after, while you can only beg to make creamies in your cloth diapers.
cuckolding, diaper discipline, feminization, humiliation, taboo
Download link ----> Ella Nova Is Your New Sissy Sitter - June 14, 2019 - 795.89 MB
I do so want you to be my little diaper babie. I’m willing to do whatever it takes to make it so. I secure your attention the best way I know how: by mesmerizing you with my big, soft breasts. You just can’t look away. They’re so beautiful and feminine. You find yourself compelled to do whatever I tell you, even act like a babie! I start reminding you of all the advantages of being a diapered little babie: 24/7 access to my breasts, unyielding love and attention, and the comfort of a soft, pillowy diaper! All you have to do is submit to the seduction of Mommie’s gorgeous breasts
diaper, diaper fetish, taboo, robo, adult babies
Download link ----> Breasts Compel You to Wear Diapers - February 28, 2017 - 1.73 GB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
milf, diaper, diaper fetish, pee, pov sex
Download link ----> FREE Diaper Hookup - August 15, 2022 - 98.28 MB
Would my special boy like a treat for his cute cock from Mommie? No real pussy for you sweetie but I have something almost as good in mind. Why don't we take of all our clothes and Mommie can use your little rubber toy pussy to make you feel good. Maybe you can show Mommie that your cock is ready for the real thing soon
handjobs, milf, taboo
Download link ----> Rubber Pussy Handjob from Mommie - February 05, 2017 - 372.2 MB
Your new efficiency expert has some, shall we say, unusual ideas about how to make the most of your time. Item one: A thick, crinkly diaper! She has to do a little work talking you into it, but eventually you agree to let her diaper you. You get so excited while being diapered that you actually cum! Unfortunately, it wouldn't be very "efficient" for me to be changing you all day, so you'll just have to be stuck in that cummy diaper until quittin' time!
milf, diaper, diaper discipline, diaper fetish, femdom pov
Download link ----> Efficiency Exert Diapers You - October 05, 2018 - 1.82 GB
People might think that we’re polar opposites, even though we’re brother and sister. I’m prim and bookish. You, if I’m honest, are kind of a slut. You start teasing me about why I don’t have a boyfriend. You’re sure that I’m really cute under that prissy exterior. And isn’t that a dirty book that I’m reading? You’re so annoying that I finally put down my book to inform you that I don’t want a boyfriend. I can just make myself cum if I want to. But if I was going to date someone, it would probably be a guy like you, even though I’m a little perturbed by you at the moment.
Then you say that you’re down. If I want to try being with a guy like my brother, you’re completely willing. You can see the slutty, pink lingerie I’m wearing under my clothes and I’m sure that you’re messing with me, but you insist. I look into your eyes and can’t help but admit that I do want you. I tell you to lock the door, then I start stripping and showing you exactly how slutty your stuck-up, buttoned-down sister can be
pov sex, sisters, slut training, taboo, transformation fantasies
Download link ----> Prim Sister Admits Her Lust - March 11, 2018 - 1.77 GB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
milf, pov sex, squirting, taboo, board games
Download link ----> FREE Mommy's Sex Addiction - February 24, 2023 - 88.46 MB
I knew something was wrong when I walked in on my girlfriend, Bambi, still naked with curlers in her hair, even though we were running late for a very important business dinner. I was still shocked when the little whiny baby admitted she had wet herself and ruined her dress right before I got home. I pulled the immature panty wetter over my lap so I could spank her naked bottom while I figured out what to do. I decided that if Bambi could not attend this important event as my adult partner then she would attend as my regressed little diaper girl.
First, I plugged her adorable little round ass then taped the crybaby into a big embarrassing diaper with babyish print. Next came a pretty pink little girl dress with frilly white stockings. I knew dressing her up like an adult baby girl and making her call me Mommy all night would make this dinner incredibly humiliating for Bambi but I needed one last touch to make sure she learned her lesson. While all the grownups are having wine, Bambi will be sipping from a bottle that contains a very, very special ingredient from her Mommy.
butt plug, diaper discipline, pee, spanking f/f, taboo
Download link ----> Bambi Belle's Regression Punishment - July 12, 2019 - 538.15 MB
Your teacher called and says you’re struggling. It’s been so hard keeping you focused on your work. What if Mommy let you see more of her… boobs while we studied together? I unbutton my dress and flash you some DD cleavage while reading from your history book — and it works! Mommy will give you whatever you want if you keep this up. I’m a little taken aback when you ask to see more of me, but I don’t see the harm and I’m so proud of you. I take my big tits completely out of my dress and play with them for your amusement before it’s time to make dinner.
I show up in a micro-bikini for our next session so we can get straight to work. You perform so well that I offer to give you another show, but this time you ask to see my … pussy. I’m embarrassed but, determined to keep you motivated, I pull my bikini bottom down and give you a full show of Mommy’s vulva. It feels naughty and I play with my clit a little while you watch before deciding to end the session.
You wait for me in the study on Saturday and I show up completely naked. I can’t tell you how proud I am, darling, so I’m going to have to show you. You take your throbbing cock out and let me stroke it, lick it, and suck it while I fawn over you. I get so horny playing with your dick that I bend over the table and let you drill my tight wet pussy from behind. You fuck me like a stud and make me squirt all over everything before pouring hot cum into my quivering sex.
Mommy didn’t know how much she’d LOVE being your study buddy! XOXO
pov, milf, cock tease, taboo, micro bikini
Download link ----> Slutty Mommy Study Buddy - April 08, 2022 - 4.23 GB
While obnoxiously snapping my gum I complain that Mom won’t give me any money to go out. She says that I’ve been asking for too much. You start to hint that you might have a way for me to earn some cash from you. When you tell me that you want me to take my clothes off, I initially don’t believe you. Go look at some porn, you perv! But, just out of curiosity, how much will you give me? Fuck! $100 is a lot. And…all I have to do is take my clothes off for you in a sexy way? Okay… I strip out of my daisy duke shorts and white bodysuit, spreading my pussy and shaking my fat ass for you. That’s when you spot something on my bedside table. I insist that it’s just a back massager, but you insist that there’s something much more fun that I can do with it. You’re so smart, big brother
blackmail fantasy, imposed stripping, sisters, strippers, taboo
Download link ----> Slut Sister Strips for $100 - July 16, 2017 - 1.75 GB
We’re having a lovely mom-son masturbation session. I’m so glad that I have this great big cock so we can jerk off together! That’s when my phone rings. Of course I don’t stop masturbating to answer it. Unfortunately for you, it’s your teacher calling to tell me that you’ve been slacking in your schoolwork. This simply won’t do! You’ve been a very bad boy. You’re going to have to be doing some aggressive sexual service for Mommie’s feta cock to make up for your negligence! I’m going to be fucking your ass and cumming in your mouth over and over again. Clearly you’re having trouble focusing because I haven’t been using you hard enough! We have a simultaneous orgasm with me shooting my cum right down your throat and you cumming all over my shiny, black heels. I make you watch me lick them clean in order to get you ready for round two
milf, futa, futanari
Download link ----> Grounded by Mom's Futa Cock - October 01, 2017 - 1.74 GB
I am fed up with you, my lazy hubby, but I have the perfect plan to make you give me the attention and love that I deserve. If you can’t worship me as a wife then you will have to learn to spoil me as a baby. I confront you wearing my robe with a regression formula in hand and I explain that if you can take good care of me in my new adult babyhood then I might give you a second chance as a real husband. I down the formula and take off my robe to reveal I am naked except for a puffy white diaper.
Now are you going to be a good Daddy or are you going bye-bye forever?
blackmail fantasy, diaper, taboo, toe sucking, adult babies
Download link ----> Wife's Ultimatum - April 05, 2019 - 659.13 MB
No storyline here, just lots of my big round diapered bottom and fat juicy pussy. I spank myself for being a naughty baby over my white plastic pants and crinkly diaper. Then I prove that I really am a naughty baby by getting out my dildo to give myself a nice big orgasm without even asking Step-Daddy's permission!
diaper fetish, dildo fucking, self-fuck
Download link ----> Solo Diapered Spank and Fuck - April 10, 2020 - 771.23 MB
Owen learns a lesson in paying proper attention to his girlfriend when Penny ties him to the bed and makes him study each pair of her panties... as she sits on his face wearing them. She demands reviews and comments about his favorites while she amuses herself ny playing with his fat cock. In the end she decides to be generous and let him cum on his favorite pair
femdom, mistress, lace/lingerie, fetish
Download link ----> Appreciating My Panties - January 26, 2015 - 839.26 MB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
sph, diaper discipline, diaper fetish, femdom pov, humiliation
Download link ----> FREE Babysitter Fucks the Diapered Cuck - August 24, 2022 - 173.59 MB
Ready to do some yoga with Mommy? I run through a series of sexy stretches and poses as you watch, practically drooling over my MILFy curves, which are accentuated by tight, my hot pink, yoga outfit. You’re barely keeping it together when I insist that you start participating more. You manage to resist, but when I lean in to help you stretch, my bit, MILF tits in your face, you can’t help but get an erection.
But it’s nothing to be embarrassed about, sweetie. And since Mommy made you all stiff, then Mommy can help you get release. I unclasp my sports bra and tell you to stroke your big cock as fast as I play with my big, soft tits. But don’t come yet. Watch me peel the pink leggings and thong off of my round, juicy bottom before sensuously oiling up my breasts and ass.
I know it’s naughty, sweetie, but I really like it. I drip oil onto my pussy and rub my clit in your face while you continue to jerk off to my instructions. I get closer and closer to coming before I can’t wait anymore and countdown to a simultaneous release and you cover my pussy in your jizz as I reach my own screaming orgasm.
Isn’t it fun to stretch it out with Mommy?
pov, joi, lotion/oil fetish, taboo, yoga
Download link ----> FREE - JOI to Mom's Yoga Body - July 28, 2023 - 183.22 MB
I’m soooo excited to meet you! This is my very first public diaper date, and I’m a little nervous. I love telling you all about what got me into the scene and the kinds of play I like to do. You’re such a good listener that I’ll let you peak up my dress as I wet the adorable diaper I picked out for today. I’m so excited that I expose my breasts and masturbate under the table right in the restaurant! Will you PLEASE come back to my place for a… change? Oh, thank you, thank you, thank you!
First, watch me wet myself some more and masturbate on my couch before I strip down to just a diaper and heels. Then I’ll take your big dick out of your wet diaper and give you the enthusiastic blowjob you deserve. But don’t cum just yet! It’s time to take off my diaper and fill my dripping wet pussy with that beautiful cock. Now don’t stop fucking me until you fill me with cum, diaper boy!
Oh, wow! Do you think we could do this again tomorrow?
cream pie, diaper, diaper fetish, pee, public flashing
Download link ----> Diaper Date Cream Pie - July 24, 2021 - 4.59 GB
Do you like my adorable pink uniform with this nice boob window and the word "Daddy's" written across my pantied bottom? I know you just want to pull your little cock out and start jerking away but you have to wait till I finish putting on my outfit. First I am going to unsnap my bloomers so I can tape myself up in this cute pink and purple diaper then I am going tell you exactly how I want you to stroke it.
Can you follow my wanking instructions like a good boy even with my big, round diaper butt right in your face? I am an expert at teasing little diaper pervs with just the right wiggles and crinkles but you better not make a creamy till I say so. If you play with yourself just like I tell you to then I might let you make my diaper all sticky with boy stuff.
cheerleaders, cock tease, diaper, diaper fetish, jerk off instruction
Download link ----> Diaper Cheerleader's Teasing JOI - February 08, 2019 - 1.94 GB
I know you are just my lowly assistant but today you have the privilege of witnessing history with the first demonstration of my new mind control device. You can also be my first test subject. Wait. Something is not right, I feel funny...
I don't know what happened to my machine but I will figure it out with my crayons and stuffies. If my diapy stays dry long enough. I tried to hold it like a big girl but it's too hard. You have to change my diaper if I do have an accident. That's the rules because you are the lowly assistant and I am the big smart boss. Yes, you do! I can't solve these hard math problems in a wet diaper.
diaper discipline, jeans/pants wetting, taboo, transformation fantasies
Download link ----> Scientist Regressed into Diaper Brat - June 05, 2020 - 518.71 MB
Follow me on Twitter @pamperedpenny
Follow me on Instagram @pampered_penny
XOXOX
latex, mistress, female domination, glove fetish, behind the scene
Download link ----> Uncollaring My Submissive - October 15, 2017 - 1.74 GB
If I am the only one that wants to play Monopoly then I guess we can have an orgy instead. Lola and I put on a little show for the boys as we strip each other out of our clothes and take a minute to appreciate each other's soft breasts and juicy asses. Lola insists on getting Step-Daddy's big cock all to herself and of course, she has to make some teasing comments about her step-brother's not so big one.
I don't mind taking care of my little guy's little guy, though. Big and small cocks of the family are both treated to blowjobs, tit fucking, and foot teasing before we flip over to offer up our wet pussies. Lola makes fun of her step-brother again because she is orgasming all over Step-Daddy's fat dick and I have to use my hand to get off while riding my special boy. She might regret all the teasing before Family Fuck Night is over since small things sometimes cum in huge loads.
sph, big loads, pov sex, taboo, mommy roleplay
Download link ----> Family Fuck Night with Lola Fae - April 19, 2020 - 709.64 MB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
milf, mesmerize, mind fuck, taboo, collars / leashes
Download link ----> FREE Melting Mommy's Mind - August 12, 2022 - 121.24 MB
Bambi likes to help Mommy diaper you at night, probably because she wants to add to your embarrassment about wetting the bed. When you start to get really fussy about being diapered by your giggling sister though, I decide it's time Bambi learned exactly how it feels have her bottom powdered and padded in front of a sibling!
Bambi is very pouty about being treated like a baby when she does not even wet herself so she quickly turns my own idea against me. If we really want to make you feel less shy about your diapers then I guess I better put one on too! Once we are all three taped up and crinkly, diaper time starts to turn into naughty playtime with lots of rubbing Bambi's cute padded bottom in your face and diaper crotch kisses from Mommy. Bambi and I make sure that from now on you like diapers so much you might just pop!
blow jobs, cock tease, diaper, diaper fetish, taboo
Download link ----> Bedwetter's Diaper Sex Reward With Bambi - January 04, 2019 - 1.47 GB
NaI could tell you were acting a little strange but I never expected you to confess your secret desire to be diapered and sissified. I imagine you were even more surprised that I was totally into the idea. I even have some stuff leftover from doing Mommydomme play in the past. When I tell you to get naked for your first diapering I see that you have already shaved off all your body hair. Looks like someone is very eager to be my little sissy baby.
I hope you know that this fantasy is going to play out how Mommydomme wants it to, not just whatever the baby wishes would happen. That means I get to finger your cute little bottom while I make you edge yourself over your open diaper as many times as I want. That also means a big vibrating butt plug and frilly pink outfits. Don't worry, you will still get to have lots of little sissygasms in your diaper as long as you are a good girl.
butt plug, diaper, diaper fetish, femdom pov, feminization
Download link ----> Girlfriend Encourages Your Diaper Fetish - May 26, 2020 - 945.14 MB
I’m parked over here, darling! Everyone else seems to have left, what took you so long? Oh my, you’re all sweaty and flushed. Do you like my new bikini? You asked me not to wear the one I had on earlier, so I changed. Did I make you hard again, sweetie? Get in the back seat and keep a look out and Mommy will help you come again. I’ll rub your hard-on all over my big tits before I see how much of it I can take in my mouth. This feels so naughty and is making Mommy so horny. Please fuck Mommy’s pussy in the back of our car! You can lose your virginity the same way Mommy did. After you give me a screaming orgasm, I let you decide pick where your cum goes again. In my coffee?! What is with you feeding me your cum today? I’ll do it because you fucked Mommy so well. Since my bikinis seem to give you so much trouble, how about I drive home naked?
milf, cum in mouth, pov sex, taboo, public outdoor
Download link ----> Very Inappropriate Ride Home With Mommy - July 30, 2021 - 2.96 GB
Your new room is really coming along, sweetie, but I have a great decorating idea for you. Let's match the paint color with your stiff cock! I brought the color samples so drop your pants and I can start comparing. I just think your boner turns a very cute pinkish red when you get excited so why not use that for some inspiration. I know watching me play with my big, full breasts makes you excited so just relax while I make sure you are ready.
I told you it gets a very pretty complexion when you are nice and hard. I do think there is one more thing we need to try, though. I want to compare the colors after your cock has been inside me. If you want Step-Mom's help with some decorating then I want your help with some dick.
milf, big tits, pov sex, taboo, mommy roleplay
Download link ----> Fucking Step-Mom in Your New Room - September 07, 2020 - 565.51 MB
How could I have guessed that dabbling with dark powers would make me a grow a huge dick? Now your mom has this giant cock just dangling right in front of your face and I don't know what we can do about it! Great idea, sweetheart, we should ask the ouija board how to rid of this monstrous mom cock since asking it a question caused my dick to appear.
C-U-M
I guess I am going to have to find a way to make this massive thing ejaculate if I want to get rid of it. It does feel really good to touch my own cock but I am not sure how to get myself off now that I am a dickgirl. Since you have a lot more experience with having a penis, could you help mom figure how to shoot her load, pretty please?
erotic magic, futa, taboo, mommy roleplay
Download link ----> Supernatural Futa Mom Needs To Cum - June 23, 2019 - 735.79 MB
A Penny Barber Fantasy. Become a member to see ALL my videos and follow me at Twitter.com/PamperedPenny! XOXOXO
Get the full video at www.manyvids.com/Video/4547616/Watching-Porn-With-Mommy/
pov, milf, taboo, caught, mutual masturbation
Download link ----> FREE - Watching Porn With Mommy - August 04, 2023 - 153.56 MB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
pov foot worship, taboo, scent fetish, mommy roleplay, cum on tits
Download link ----> FREE Scent of a Mommy - August 03, 2022 - 94.41 MB
You can't wear jeans and a T-shirt on Halloween, sweetheart. I was so excited to do fun stuff and pass out candy all night in our costumes. Don't you like my space woman outfit?
I bet I know what you want to be doing alone in your room all night instead of celebrating spooky times with your Mom. Maybe if I play with your cock right now then you won't have to skip Halloween to play with it by yourself later? I am willing to unzip my costume and let you see my perfect tits but I am only taking my costume off if you put yours on.
handjobs, costume, big tits, taboo, mommy roleplay
Download link ----> Mom's Tits Are Your Halloween Treat - October 20, 2019 - 634.23 MB
I think you know why your teacher called me but I am pretty sure you have no idea what she plans to do with you. You have been warned that there would be serious consequences if you did not stop getting distracted during class by drooling over cute girls. Your teacher has sent something that she believes will help discourage this behavior. It's called a chastity device.
Stop begging and take off your pants. You have had enough chances and now it is time for punishment. I know it is uncomfortable, that is the point, but it is about to get much worse. Your teacher also suggested that your little lesson should include Erectile Dysfunction medication and lots of cock teasing. Did you really think that the pill you just swallowed was pain medicine to help with your sore balls? Poor boy, you have no idea what sore balls really means. Yet.
milf, cock tease, taboo, key holding & chastity, mommy roleplay
Download link ----> Chastity Devices & Dick Pills from Mom - February 09, 2020 - 642.26 MB
I hope you understand that we have some traditions in our family that some might call peculiar. If you want to join us by marrying my darling girl then you must prove your sexual prowess to me. Right now in my bedroom. Once you see the slutty little bodysuit I am wearing under this dress you will realize I am very serious. I promise that your fiancee also insists I give you this trial by fuck and she simply won't marry you without my approval of your cock.
I think the sight of my big, soft breasts and curvy MILF ass will help you get over your reluctance. If I am not mistaken, this test will be quite easy for you. I get a very strong "big dick and knows how to use it" feeling from you. Now you just need to prove it by filling my pussy until I cum my brains out.
milf, older woman / younger man ., pov sex, taboo, mommy roleplay
Download link ----> Mother-in-Law Sex Initiation - June 14, 2020 - 722.25 MB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
pov, big tits, diaper, diaper discipline, diaper fetish
Download link ----> FREE Wifey Discovers ABDL Search History - September 05, 2022 - 227.71 MB
In this week's episode, somebody finds a mesmerize device and uses it to give Lois a diaper fetish! The usually sensible Mom now just wants to give seductive diaper changes and parade her own diapered butt all over the house. Will Lois come to her senses or will the redheaded housewife end up horny for big, crinkly diapers forever?
milf, cosplay, diaper fetish, mesmerize
Download link ----> Lois Griffin Diapers Peter and Herself - August 07, 2020 - 516.83 MB
It is finally time to let my little pantyboy out of chastity. This sissy is especially lucky because I brought her a pretty pink cocklette ring that says PRINCESS! Once the pantyboy is unlocked I cover her little princess stick in lots and lots of my favorite panties! The little sissy hasn't cum in so long I doubt she will able to last very long ebfore she explodes all over herself (and my panties)!
blowjob, chastity devices, femdom pov, panty fetish, sissy training
Download link ----> Covered In Panties - February 09, 2016 - 1.24 GB
It looks like a silly little baby made a silly little mistake when he made our hotel reservation. This is not the place Mommy told you to book but that is okay because they won't ever let us stay here again. Not after the housekeeper sees a grown man all tied up and diapered on the bed.
I think it is a very fair punishment for being a forgetful diaper boy and Mommy is the one who decides what is fair. Now I just have to decide if I want to put this nice fat dildo in your naughty mouth or your naughty bottom before I put you in bondage. Either way, I expect your diaper to be soaked and sticky when I get back from the bar. Don't worry, Mommy is going to take her time teasing you with my tits and ass before I go so it will be easier to make a creamy. Would it be more embarrassing for the housekeeper to find you wet and smelling of cum or just with a little stiffy in your diaper?
bondage, diaper discipline, diaper fetish, femdom pov, humiliation
Download link ----> Mommy's Punishment for Diaper Boy - January 24, 2020 - 628.24 MB
What would you like for Christmas this year, sweetie? A girlfriend!? Well those can be difficult to wrap, so don’t get your hopes up. I finish my umteenth cup of special eggnog, and go back to laying out holiday decorations.
Later, you come into my bedroom after I call you. Mommy’s wearing nothing but a Christmas sweater covering what appears to be VERY skimpy lingerie. A festive pillow sits in my bare lap. I think I know what you really want for Christmas, darling. Sex! Now, since we won’t be alone on Christmas, Mommy will just have to give you your present early. I strip down to my lingerie as you take your swelling cock out of your pants. Mommy makes your cock nice and slippery before riding you to several delicious cowgirl orgasms. Exhausted, I let you lay me down and fuck me as hard as you can in missionary until you cream pie my quivering pussy. Looks like Mommy’s present came early, too! XOXO
lace/lingerie, big tits, pov sex, taboo
Download link ----> Mommy's Your GF for Christmas - December 17, 2021 - 3.29 GB
I was already annoyed when I saw that your school was calling me because I really, really needed to pee. I decided to take the call in case it was an emergency but of course it was just more reports of your perverted behavior. I finally get done apologizing for your hidden cameras in the girl's locker room (squirming in desperation to pee the whole time) and run to the bathroom for some relief. Then, of course, right after I finally finish peeing and stripping naked for a shower, I realize you have brought your filthy habits into my house. I can't believe you would jerk off to your step-mom doing something so private!
hidden cam, milf, female desperation, pee
Download link ----> Pee Freak Caught Spying on Step-Mom - September 20, 2020 - 1.28 GB
Watch the full clip in my store!
diaper, diaper discipline, diaper fetish, femdom pov
Download link ----> FREE Conditioning You to Love Diapers - May 10, 2021 - 157.76 MB
I had a hilarious coaching session with a couple consisting of a trying-so-hard-to-be-dominant wife and pseudo submissive husband. (At least, it's hilarious if you like hearing about men being put in their place.) I wish them the best!
Follow me on Twitter | https://twitter.com/pamperedpenny
See me on Instagram | https://www.instagram.com/pampered_penny/
Perv out on me on FetLife | https://fetlife.com/users/53960
femdom, bdsm instruction, female domination, instructional, behind the scene
Download link ----> Strict Discipline for a Boring Husband - May 25, 2017 - 1.75 GB
Can you tell me what seems to be the problem, sweetheart? You have an owie "in your pants"? Oh, I see. I guess it does look a little red and maybe chafed a bit. I think maybe you have been playing with it too much. I bet all you need is a little ointment, a band-aid, and some kisses from Mom to make it all better.
I am worried that it might happen again though. You know that your dick is not meant just to be stroked by your hand and that you can always ask Mom to let you practice the real thing. Let me show you what I can do for your cock so you don't have to be rubbing it yourself so much.
blowjob, pov, milf, taboo, mommy roleplay
Download link ----> Mom Takes Care Of Your Over Wanked Cock - December 08, 2019 - 684.72 MB
After years of yearning, you finally work up the courage to tell me how you feel about me. But now that you finally have my attention, you don’t know what to do with it. How sad! I’ll make you a deal: if you behave and do exactly as I say then maybe we can make this work. Get on your knees, rub my feet, call me Mommy, and…let me say humiliating things to your small penis while I put you in a pretty, pink diaper! This isn’t exactly what you had in mind when you worked up the courage to ask me out, but you’re going to need some way to stand out against all my other little playthings. Wearing a diaper while you wait on me and my friends might be a little embarrassing, but you’ll do it for the woman of your dreams, won’t you? Of course you will.
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diaper, diaper discipline, diaper fetish, femdom pov, humiliation
Download link ----> Diapered by Your Crush - July 10, 2021 - 4.52 GB
I really wish I could drive you to school today, sweetie, but I am just so overworked and stressed right now. You can help me relax? Mommy will try anything.
Whoa, not only do I feel relaxed, I also feel incredibly horny! Before preparing the sugar cookies for bake sale later, I strip out of my dress, fondle my big juicy tits and ass, and finally put on nothing but an apron. You come home right as I pull the hot cookies out of the oven. I’m so horny that I drop to my knees in front of you, expose my breasts, and beg you to take your giant cock out. I blow you until I can’t take it anymore and make you ram that massive dick into Mommy’s tight, wet pussy. I ride you on the counter, squirting all over your dick so hard that you think I must be in heat.
You finish by helping Mommy decorate one of the cookies with your cum, which I gratefully devour. From now on, I’ll just come for you — I mean, to you — whenever I want to relaxxx.
pov sex, squirting, taboo, cooking, mommy roleplay
Download link ----> Penny Barber - Sugar Cookies - January 01, 2023 - 3.93 GB
You just had to make a snotty remark at me before my promotion interview, didn’t you? Well, guess what. I got the job! Now, if you want to keep your’s then you are going to have to do what I say. You’re going to come into my office first thing in the morning and let me humiliate your small penis while I put you in an adorable little diaper! You can sit in it on my floor for the rest of the day while we both get our work done. As a perk, I’ll work naked! While having a little erection makes the diaper less comfortable, I’m impressed that you still manage to fill it with pee. But I won’t let you get changed until the end of the day — and you’re going to have to take this note to Allison and see if she’ll do it for you. Remember little diaper slave, to get ahead, you have to be goal oriented.
diaper, diaper discipline, diaper fetish
Download link ----> Rival Coworker Diaper Punishment - August 20, 2021 - 3.87 GB
Even after all the sex we’ve been having, you’re still horny, because there’s still one thing you haven’t had: Mommy’s pussy. You know I want it, too, but I’m so worried that we’re going to ruin our relationship! However, after an entire day of fucking, sucking, licking, and stroking, I just can’t help myself anymore: I need your big, fat cock. So, when you walk in on me masturbating at bedtime, I invite you over for a mother-son fuck fest. You ride me frontwards and backwards before you finally commit the ultimate taboo sex act and come in my eager MILF pussy. I love you so much, honey!
milf, pov sex, taboo, mommy roleplay, pov blowjob
Download link ----> Finally Fucking Mom - October 16, 2020 - 1.82 GB
I am proud of the progress we have been making in your sessions but there is a form of therapy I think you should try. I must warn you that this treatment would require some significant changes to your lifestyle and would require that you promise to leave all decisions in my hands for the duration of this therapy. If you are sure you are ready to start then please get undressed and lie on the floor.
I need you naked on the floor so I can put you in your diaper, silly. Regression therapy is simply useless without diapers. Speaking of useless, that is an adorably tiny erection you have there. I guess somebody is excited to be so intimate with his therapist. I knew that you had a huge crush on me and that you were exactly the kind of man I like to make into cute little babies. I have so many ideas to regress and humiliate you. You will be wetting and creaming your diapers for my amusement from now on. Don't be too sad, diaper boy. If you are a good baby I might let you nurse on my amazing tits sometimes.
sph, diaper fetish, femdom pov
Download link ----> Therapist Makes You Her Diapered Sex Toy - April 24, 2020 - 709.26 MB
Watch the full ABDL clip TOMORROW in my ManyVids store! XO
diaper, diaper discipline, diaper fetish, taboo, nurse
Download link ----> Rx: Mommy Domme Extended Trailer - October 23, 2020 - 152.24 MB
I can barely believe how big and stiff your perfect cock gets when you make me wear a diaper. I just want to be a good girl so Daddy will fuck my brains out and if that means dressing up like a slutty school girl and wearing a big puffy diaper under my short little skirt then that is exactly what I will do. I do feel a little embarrassed being diapered but I am way too horny to really care. Even when you insist that I have to wet my diaper before I get fucked. This little diaper girl will do whatever it takes to earn Daddy's dick.
blowjob, daddys girl, diaper, diaper fetish
Download link ----> Diaper Slut Is Desperate For Your Cock - October 04, 2019 - 737.55 MB
Our family vacation has been so stressful. I sneak downstairs in our cabin to masturbate the tension away— and I catch you spying on me! Well, if Mommy can’t get time to herself then come join me in the loft for a secret nightcap. Did you like watching Mommy play with herself? I open my robe to reveal my big soft tits and tell you to take out your painfully obvious erection. You jerk-off exactly how I tell you to as I stroke my hard clit, finger my wet pussy, and tell you all the dirty things I want to do with you for the rest of the vacation. You delay your orgasm, as instructed, and let Mommy mount your beautiful cock. I ride you as hard as I can without waking your father and sister until I have to muffle my own screaming orgasm as you come inside me. Now I think this is going to be a REALLY fun vacation, sweetie. XOXO
pov, milf, orgasms, pov sex, taboo
Download link ----> Family Vacation Masturbation Frustration - September 10, 2021 - 4.62 GB
What would you like to do tonight, sweetie? Don’t tell me you’re busy looking for a new place to live again! I spread my legs, flashing you my bare pussy, and tell you I’m going to give you several reasons to stay with Step-Mommy. I grab my vibrator and let you watch as I bring myself to a delicious orgasm right in front of you. You’d be hard-pressed to find a roommate who will strip naked for you and put on a sexy show with their pretty glass dildo. I tell you to take out your cock and stroke it while you watch me masturbate. Step-Mommy is always soooo horny, darling, and I can see how hard it’s making you. I get on my knees and stroke your perfect cock before sliding it between my soft lips. You finally agree to stay if you can fuck my eager wet pussy and I ride you to a screaming orgasm before you release your thick load inside Step-Mommy.
If we’re going to be roommates, we should make some house rules. How does naked laundry day sound? XOXO
masturbation, milf, pov sex, taboo, pov blowjob
Download link ----> Mom Convinces You to Stay - March 25, 2022 - 3.98 GB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
milf, magic control, pantyhose footjobs, pantyhose, taboo
Download link ----> FREE Controlling Top Pantyhose - June 23, 2023 - 239.73 MB
Barely able to contain yourself after staring at Mommy's bare feet and perky nipples — poking through my questionably appropriate outfit — you grab your phone and some tissue the moment I leave to go shopping. I come racing back in after deciding to order a pizza, and I find you masturbating I the living room! I know I should be upset, but I’m fascinated by your beautiful cock. What if Mommy helped you…finish? I get down between your legs, lick my palm, and lovingly stroke your nervous erection. While I take it between my big tits, I sneak a peak at your phone to know what you were jerking off too. Seems like Mommy really is your type! I strip down to my sneakers and pleasure you with my eager mouth, snapping a few pics for your personal use later. I get maddeningly horny deep throating your fat dick and beg you to fuck me. I can’t help but scream as you make me come. You’re going to finish the way you started. I finger myself in front of you and count us down to a glorious simultaneous masturbatory orgasm.
Now, what do you like on your pizza, stud?
milf, masturbation encouragement, pov sex, taboo, caught
Download link ----> Mommy Catches You & Helps You Finish - December 03, 2021 - 1.34 GB
This is a really hot, sensual clip. Highly recommended!**
You’re so cute! Oh, but not when you have an erection. I only like your cock when it’s little and tiny and small. I give you a tough decision to make: we can keep your cock cute with either a chastity device or a diaper. You stutter and blush so much that it takes a bit for me to get it out of you that you want the diaper.
I powder your little cock down with a pink powder puff, but you just keep getting harder and harder, oozing precum and embarrassing yourself. I even put some diaper rash cream on, since you’re going to be in diapers for a whole week—longer if you’re not good. Because you can’t jerk off when you’re in a diaper. Don’t act so surprised. What did you think was going to happen?
Could you even jerk off in a diaper? I don’t think so. It’s too embarrassing. Even f I was teasing you, I doubt that you could do it, unless you’re some kind of pervert. Just to prove it, I take off my bra and start massaging your diapered cock with babie oil. This whole week I’m going to be walking around in slutty little outfits. Whenever you start to get an erection, your diaper is going to crinkle and remind you that you’re just a little adultbaby! We can gauge how much you like the new outfits I ordered by how much your diaper crinkles
chastity devices, diaper, diaper discipline, diaper fetish, key holding & chastity
Download link ----> Diapers or Chastity: You Have to Choose - March 20, 2017 - 1.75 GB
That boy, Alrik, is picking on you again. This time he gave you such a wedgie that Mommy has to get down and lick your poor little butthole. But don’t you worry, sweetie, because Mommy would do anything for you, even seduce some asshole just to give his asshole a taste of his own medicine. A few text messages and he’s over at our house, with no idea that I’m your mom, and even less of an idea of what’s in store for him! I’ve learned that there’s only one way to deal with bullies: break them down, humiliate them, and make them your submissive plaything. Trust me: it’s easier than you’d think. And that boy won’t be bothering you anymore—but he will be taking Mommy’s big dick whenever I say!
strap-on, femdom sex, pegging, rimming, mommy roleplay
Download link ----> Mommy Butt Fucks Your Bully - November 15, 2020 - 4.61 GB
Watch the full clip in my store! XOX
Follow me on Twitter.com/pamperedpenny
pov, fuck machine, fucking machines, taboo, mommy roleplay
Download link ----> FREE Fucking Machine Makes Mommy Your - July 17, 2021 - 156.03 MB
There is something very frustrating about so called "submissive" men who promise to obey my every command but only offer hesitation and excuses when things get real. Luckily, I know how to deal with fussy babies who are too scared to properly serve Me. A little special Mommy juice is all it takes to drain the willfulness out of you so I can remake you into the feminized diaper doll I desire.
Embarrassing pink diapers and sissified snap-crotch onesies are much more pleasing to me than the shoddy men's clothes you wore to our meeting. I have destroyed those boy clothes for you and I have special pink ribbon for your little thingy before we tape it up inside your diapy. There is one other thing we need to do before we finish diapering you. I have this little enema bulb that is going to help make sure you truly regret ever resisting my wish to diaper you
diaper discipline, diaper fetish, enema, feminization, taboo
Download link ----> Messy Punishment for Stubborn Sissy - September 27, 2019 - 803.52 MB
I am just so happy you decided to join our world of diaper sluts! Well if you did not want to join us then you should not have bought that naughty stuff online and made it so easy to find you. You are already naked and shaved so why not put on your diaper like a good baby? We are going to have so much fun picking out matching diapers, matching butt plugs, and maybe even matching tits if you are lucky.
Now just be a sweet little sissy baby and take your regression medicine so I can get both our bottoms covered in adorable, puffy diapers. If you don't make a fuss, I might even let you watch me cum in my diaper.
butt plug, diaper fetish, magic control, taboo, sissification
Download link ----> Diaper Bimbo Wants A Pet Sissy - August 02, 2019 - 841.21 MB
I am a little confused when I find a very old pair of skintight vintage jeans mixed in with the laundry. My ass always looked great in them but they have been stored in the attic for years. Now I find them in with the clean laundry and my son is very keen for me to try them on. So keen that he doesn't even give me a chance to undress myself and pulls my skirt down before I even know what is happening. I am a little embarrassed to have him see my butt in just a thong but try to just go along since he seems to really want to find out if the jeans still fit.
The jeans are tight but I can definitely still get them on and I have to admit my butt still does look great in these jeans. My son thinks they look so good we should take some pictures but for some reason he insists the photos would look better without a top in the way so he pulls my blouse over my head before I can react. When I started laundry today I certainly expect it would end with me topless, wiggling my hips, and posing with my denim covered ass popped out while my son takes photos of me. At least, I hope that is all he is doing back there.
ass fetish, jeans fetish, taboo, mommy roleplay
Download link ----> Obsessed With Mom's Jean Covered Ass - March 17, 2019 - 724.5 MB
I want to make sure my special boy starts his new year off with a bang so sit back and enjoy the sight of your mom naked except for my red evening gloves. I know you love to stare at my bare breasts anytime you can but I think they look sexiest when they are covered in your hot cum. Luckily I have some special lube to make it look like my soft tits are already covered in your sticky load.
I also brought baby oil and body glitter so you can decide which way you like your mom's big, beautiful breasts the most- sparkly, shiny, or plastered with cum. Either way, I will be expecting many loads of the real thing all over my perfect mom tits this year!
milf, role play, joi, big tits, taboo
Download link ----> Mom Shows Off Her Tits On New Year's Eve - February 17, 2019 - 763.33 MB
Watch the full clip in my store! XOX Follow me on Twitter.com/pamperedpenny
cream pie, pov sex, taboo, collars / leashes, cum on tits
Download link ----> FREE Collared Mommy Sex Slave - August 11, 2021 - 150.99 MB
I think you know why you have been sent to my office today, little mister. As the school counselor, I am here to help all students but I was pretty embarrassed when I saw that my own son had been sent to the office for making excessive bathroom pass requests. Do you want to explain why you have been taking so many restroom breaks? I have a theory but I am willing to hear alternate explanations before administering your punishment. If you don’t have anything to say for yourself then I guess we will just have to solve your little potty problem the old fashioned way, with a diaper.
You can whine and cry all you want but you will be diapered before returning to class and everyday going forward. Instead of missing valuable learning time wanking in the boys room, you can come here for diaper changes between classes. Don’t try to deny the real reason you keep asking for bathroom passes is to play with yourself. I think that between the embarrassing puffy diaper and this roll of extra sticky tape, I think we can solve all your little behavior issues at once.
diaper discipline, humiliation, taboo, tape bondage, teacher fetish
Download link ----> Diaper Punishment at School - May 26, 2019 - 777.58 MB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
milf, pov sex, religious, taboo, mommy roleplay
Download link ----> FREE Sunday Morning Wood - January 27, 2023 - 80.12 MB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
diaper, diaper discipline, diaper fetish, humiliation, mommy roleplay
Download link ----> FREE Diaper Bet With Mom - February 10, 2023 - 107.14 MB
Submitting to me does not just mean I decide what you wear or what you do, it means I also get to decide what you are. I think you are just a little baby who needs to be diapered by his Mistress. Not before I lock up up your cute widdle thingy though. You could try to argue but we both that if I want your butt in diapers and your cock in chastity, then that is what will happen.
Maybe if you are a very good baby for Mistress then I will let you polish my red latex panties with your tongue.
latex, chastity devices, diaper discipline, diaper fetish, femdom pov
Download link ----> Mistress Decides You Should be Her Baby - November 15, 2019 - 593.75 MB
Watch the full clip in my store! XOX Follow me on Twitter.com/PamperedPenny
pov, eye glasses, pov sex, taboo, mommy roleplay
Download link ----> FREE Mommy Can't Find Her Glasses - November 05, 2021 - 209.11 MB
Itʼs finally time to settle down for Family Movie Night! I made popcorn and everything! However, you canʼt seem to keep your attention on the movie when I look so good in my white bodysuit and velvet booty shorts, my bare feet propped up on the coffee table in way that makes you wish youʼd chosen a Tarantino flick. Of course, when I notice you staring, I just start to tease you. One thing leads to another and before we know it, Mommy is naked, sucking and stroking your big dick, using my hands, feet, tits, and mouth to please my darling son and coax out a thick, creamy load of incestuous cum.
feet, milf, footjobs, mommy roleplay, pov blowjob
Download link ----> Family Movie Night - October 08, 2020 - 1.8 GB
I'm wearing a sexy pink diaper and bib, trying to entice you to fuck me. I know how much you like to screw me when I'm all done up like a little baby doll, Daddy. My soft tits jiggle under my bib as I pose and primp for you, rubbing my diaper so that it crinkles softly. I get your big, thick cock out and start sucking it, playing with it, making you nice and hard for my wet, diapered pussy. You know you can't resist your little diaper girl, Daddy
daddys girl, diaper, diaper fetish, taboo, daddy roleplay
Download link ----> Diaper Girl POV Suck and Fuck - July 27, 2018 - 1.82 GB
Why is Mommy wearing nothing but a skimpy bikini top underneath my overalls? Because we were supposed to paint the extra room today, Sweetie! You always promise, but when it comes time to do a chore, Mommy has to find creative ways to motivate you, like wrapping my soft, wet mouth around your warm, hard cock. I remove my slutty little bikini top to give you a better view of my big soft tits while I do everything I can to coax a mouthful of cum out your beautiful erection.
After painting me with your cum, it’s only fair you help Mommy paint the office. Since you’re a little drained from earlier, I keep you motivated by stripping for you and finishing the chore naked! Despite the distraction of my curvy body, you’ve done an excellent job. Come let Mommy show you her appreciation while the paint dries.
I oil up my pussy and start masturbating while telling you how horny Mommy gets when you’re a good boy. I squirt all over myself and beg you to come fuck my sopping wet pussy. You put your cock in as deep as you can, making me squirt all over your throbbing erection, before filling my quivering sex with your creamy load. Mommy loves doing chores with you, sweetheart. XOXO
big boobs, pov, milf, pov sex, taboo
Download link ----> MILF Drips - April 02, 2022 - 3.09 GB
Watch the full video in my store! XO
big tits, butt plug, cougar, older woman / younger man ., taboo
Download link ----> FREE Mommy Makes You Miss the Bus - June 14, 2021 - 193.15 MB
I was planning to spend an evening with a nice glass of wine and my big book of Playboy centerfolds because I thought you had already gone to bed, sweetie. I just really enjoy the photography and well, maybe I like looking at the pretty girls too. Not as pretty as you though. Oh come on, I bet you would make a lovely girl.
How about you slip on a bra and panty set of mine and we see if it fits? If you are right then I will buy you concert tickets but if you can wear my clothes then I get to give you a makeover. Looks like someone is excited by just the idea of wearing his Mom's panties. Don't worry I think we still get these on over your little erection. I can't believe how sexy you look all dolled up. You do make a very pretty girl but I think you would look even prettier with your lips around my strap-on cock.
imposed fem, panty fetish, pov strapon, taboo, mommy roleplay
Download link ----> Mom Gives You A Girly Make Over - May 18, 2019 - 701.92 MB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
milf, diaper, diaper discipline, diaper fetish, femdom pov
Download link ----> FREE Mommy's Little Diaper Nerd - September 07, 2022 - 213.88 MB
Watch the full clip in my store. XO
milf, big tits, taboo, transformation fantasies, mommy roleplay
Download link ----> My Son's a Werewolf! Preview - October 29, 2021 - 149.52 MB
A Penny Barber Fantasy. Watch the full clip in my store! XOX Follow me on Twitter.com/PamperedPenny
milf, rope bondage, submissive sluts, taboo, collars / leashes
Download link ----> FREE Exposing Mommy's Kinks - December 16, 2021 - 181.62 MB
I did not really believe what I was seeing when my brother walked into my mom’s room and brazenly took out her vibrator to give himself a back massage. Apparently silly little Sammy thought that was why mom owned it. I had to mess with him once he found out and so I made sure he got familiar enough with the taste and smell to know exactly where mom uses it.
All the teasing and sexual embarrassment made me decide that it was only fair that Sam get as up close and personal with me as he was with mom’s pussy. Probably a tiny bit more since I was actually sitting on his face. Then I was even nice enough to give my naive little bro a lesson in how to correctly use the “massage aid” on himself.
face sitting, imposed ejaculations, sisters, taboo
Download link ----> Making Bro Try Mom's Vibe On His Cock - September 15, 2019 - 829.7 MB
Watch the full clip in my store! XO
milf, christmas, older woman / younger man ., mommy roleplay, gloves
Download link ----> Free Relieving Mom's Holiday Stress - December 24, 2020 - 159.0 MB
Do you like my outfit, Daddy? I bet that you’ll like what’s under it better. I strip out of my I <3 Daddy onesie, but leave my knee socks on, teasing you with my big, full breasts and cute diaper. I tell you how good it feels against my neatly trimmed pussy and how much I like wearing it. The only thing that will make me like my diaper more is if you cum in it, Daddy. I want to have to wear my cummy diaper until Daddy decides that it’s time for a change. I untappe my diaper and expose my wet pussy, showing you just where I want you to cum. Don’t you think that your widdle girl looks good with your cum splattered all over her pussy, tits, and diaper, Daddy
daddys girl, diaper, diaper discipline, diaper fetish, daddy roleplay
Download link ----> Jerk Off Into My Diaper, Daddy - January 01, 2018 - 1.75 GB
When I see you outside doing yard work, I can't help but call you over to show you my 34DD tits. I'm so horny I pull down my pantyhose and start playing with my pussy. Pull your cock out and I'll give you a blowjob like only an experienced older woman can, sucking and licking your dick until you cum all over my face.
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Download link ----> Blowjob from the MILF Next Door - April 03, 2021 - 844.32 MB
Mom said that if you don’t pull your grades up, I’m going to be in charge of your orgasms for a whole month. After a call from your teacher today, it looks like you’re going to wish that you had been nicer to me! I sat down and thought out how to torment you as much as possible. But I also want Mom to keep letting me control you, so I’ve had to be pretty devious about it. Your grades do have to come up, but not too much. I’m going to start off by letting you jerk off for ten whole minutes to the Victoria’s Secret website, but you have to use your left hand. Then it’s going to be a looooong dry spell until the end of your punishment when you’ll be allowed to jerk off again, but to some material that you might find a little more difficult, but I will find so much more amusing. You didn’t know that you had such a mean little sister, did you
joi, orgasm control, orgasm denial, sisters, taboo
Download link ----> Little Sister Controls Your Orgasms - June 30, 2017 - 1.75 GB
Your mom sent you to stay with me for a while. There isn’t much for you to do around here (or so I think), but after I take a shower I promise that we’ll do something fun! And then I find the phone you left hidden under the towels. Thought you’d get a little show, huh? Well, as it turns out, Auntie knows exactly how to amuse you and that overactive cock of yours. I just hope you don't mind that auntie doesn't have a condom!
Impregnation Aunt Taboo POV sex caught masturbating hand job encouragement
pov, milf, voyeur, impregnation fantasy, taboo
Download link ----> Spying on Auntie - May 06, 2021 - 3.16 GB
Watch the full clip in my store! XOX Follow me on Twitter.com/PamperedPenny
diaper, diaper discipline, diaper fetish, femdom pov, mesmerize
Download link ----> FREE Mesmerized into Diapers - November 19, 2021 - 216.56 MB
You really need to login to your online class, sweetheart, but you also have to let me change you out of that pee-pee diaper. I am sorry I forgot to put you in a dry one when you woke up but you won't be able to concentrate if you are all wet and squishy down there. I promise no one will notice this very fast and quiet diaper change.
I did not mean to let all those comments about your bedwetting and little penis slip out but I really don't think your classmates can't hear me. The diaper crinkling is loud but I am sure they don't realize what is causing the noise. I will just finish powdering your little thingy, take care of that cute little erection real fast, and then you can fully focus on your class. I am sure nobody will know that your Step-Mommy still changes your wet diapers.
diaper discipline, embarrassment, imposed ejaculations, taboo, mommy roleplay
Download link ----> Embarrassing Diaper Change During Class - June 12, 2020 - 552.93 MB
Dinner time is family time. I really wish that you would eat the wonderful meal Mommy prepared for you, including your veggies. But you’re a stubborn boy and you know that you can get Mommy to do perverted things if you play this right. We said that we weren’t going to fuck anymore, that we were going to be a proper mother and son, but it’s soooo easy for you to find some way to convince Mommy to give up her wet pussy.
Soon you have me on my knees, sucking your fat, disobedient cock, making me more horny than hungry. I rub my slutty Mommy pussy for you, coming all over the kitchen table before hopping up to ride you, bending over to take your big dick, and finally lying down on the counter, spreading my curvy MILF legs like the whore I am to take every last drop of your hot semen.
Now, will you PLEASE eat your veggies, honey? For Mommy?
pov, squirting, taboo, creampie, mommy roleplay
Download link ----> Eat Your Vaggies - October 21, 2022 - 4.11 GB
On last week's episode, Lois got mesmerized into treating her husband like a baby and now her step-son wants to be treated like a husband! Even seeing his own step-mom naked isn't enough, he wants a blowjob from Lois. Our redheaded housewife heroine has no intention of denying her sweet boy or his sweet cock!
milf, cosplay, mesmerize, pov sex, taboo
Download link ----> Lois Griffin Fucks Chris POV - August 09, 2020 - 593.01 MB
Where do you think you’re rushing off to? You know that Mommy has to help you take care of your libido before you go; otherwise you’ll just be getting humiliating erections all day! You try to hurry me up, but I really take my time playing with you, stroking your big, hard cock; sucking you to the point of orgasm over and over again; making you fuck my big, full Mommy tits; and even teasing my asshole and plugging myself with the biggest butt plug I own, just to make sure that your balls are really, truly drained before I send you off to school. You think you might still make it, but just as I let you explode in my mouth, you hear the familiar sound of an engine outside. Yep. Mommy definitely made you miss the bus. But at least we can get started on draining your balls for tomorrow, right sweetie?
pov, milf, pov sex, mommy roleplay, pov blowjob
Download link ----> Mommy Makes You Miss the Bus - June 14, 2021 - 3.88 GB
The full video is available in my store! XO
pov, threesome, pov sex, taboo, pov blowjob
Download link ----> Sharing My Sister with My Son Trailer - December 08, 2020 - 204.38 MB
You’re such a scaredy pants when it comes to horror movies! But it is my night to choose, and that’s my favorite genre. However, I can’t flip that cushion again, Mr. Pee Pants, so I’m afraid that I’m just going to have to diaper you. I know you’re embarrassed that I’m treating you this way, but I really don’t care. We both know who wears the pants in this relationship and who wears the diapers! If you can’t control your bladder, you certainly can’t control me—and you’ll have to do all the perverted, kinky things that make my pussy throb. For starters, I think I’ll put my hand down your diaper and touch your scared little erection while you watch this horror movie. You know, you can’t deny that you like being my widdle diaper boy while your tiny cock is coming al over my big tits and your soft diaper!
Timestamps:
0:17 Teasing you about wetting your pants
3:14 Diapering you
7:26 You pee in your diaper
9:13 Checking your wet diaper
11:04 Sexual diaper change
14:53 Tits out
15:21 Diapered handjob
16:46 Coming in your diaper and all over Penny’s tits and neck
femdom, diaper, diaper discipline, diaper fetish, femdom pov
Download link ----> Girlfriend Diapers You for Movie Night - January 10, 2021 - 2.52 GB
It was disappointing but not surprising when my hair appointment was interrupted by a phone call from my husband's babysitter, Bambi, telling me that he had wet his pants again. I had to hire Bambi because I could not trust my little baby hubby to be alone without either wetting himself or playing with himself all day but the poor girl has had enough of the pathetic sissy.
I come home with rollers still in my hair from the salon and find him on the kitchen floor, still sitting in a puddle of his own shame. He is equal parts terrified and humiliated, as I explain that Bambi quit because is he too much of a baby even for a babysitter and that I was silly to let him wear boxers at all. Despite being stripped out of his wet pants and into a baby diaper and frilly pink dress by his wife, the sissy baby still finds a way to make his situation more embarrassing. His little baby cock gets hard and he has another kind of accident during his diaper change, as if I needed more proof that he has no self-control. I have a hair appointment to finish, so he will just have to wear that squishy, creamy diaper under his pink sissy dress back to the salon with me.
handjobs, diaper discipline, imposed fem, humiliation, taboo
Download link ----> Diapered & Sissified For Wetting Himself - March 05, 2019 - 1.43 GB
I am so happy that you two are going to prom together. I was not sure my special little man would be able to get a date with his, you know, little problem. Oh you don’t know what I mean? I am surprised you have not caught him in the act by now. I know most boys love to play with themselves but my little wanker is just obsessed. I can’t count the times I have walked in on him either with his hand down his pants or his dick in his hand. Sorry if this is a little shocking, sweetie, but I just thought you would already know about his jerk off addiction. Speaking of your date, I wonder what is taking him so long to finish getting ready?
milf, embarrassment, humiliation, masturbation humiliation, taboo
Download link ----> Mom Tells Date About Your Jerk Off Habit - April 14, 2019 - 647.88 MB
Another guy cancelled on me. It’s so hard to date as a single mom! I’m sure your Dad is spending every weekend with another floozy, but it’s been ages since I had a hard cock buried in my pussy. Not that you understand: you clearly take after your father. Girls are calling the house constantly and some nights you don’t come home at all. Well, it’s time that Mommy started getting what she wants—and I want your huge dick! Maybe I shouldn’t be making rules after I’ve had a few cocktails, but your new chore is going to be making sure that I’m sexually satisfied, or I’ll send you to live with your dad. It will be nothing but studying and chores. So, if you want to continue staying with Mommy, being spoiled and catered to, you’re going to have to share that huge dick! I start by stripping out of my dress, showing you my curvy, round ass, begging you to fuck me before I take your gigantic cock in my mouth and between my tits. Getting fucked might be more than I bargained for as you stretch open Mommy’s pussy, showing me exactly why you’re so popular with the girls. Of course, Mommy’s just as big a slut as your are, and I’m not satisfied until you pump a huge load of cum deep inside of me.
pov, pov sex, taboo, mommy roleplay, pov blowjob
Download link ----> Fuck Me or I Send You to Live with Dad - May 28, 2021 - 3.24 GB
I have some great news sweetheart, I have signed you up to perform in the Easter Pageant. I know it is usually just for girls but no one will know you are boy once I dress you up in this adorable pink bunny suit. I am going to transform you into the most precious widdle bunny boy this town has ever seen. You are going to look so sweet up there with all the prettiest girls from your school, dancing around and shaking your puffy bottom with its cute bunny tail. Oh your bottom will have to be puffy from the diaper, silly. You do have to be diapered because you cannot unzip the bunny suit without Mommy’s help and so you will not be able to take any potty breaks. We wouldn’t want you to have an accident on stage, now would we?
I also have the cutest little bunny ears for you to wear and we are going to give you some whiskers and a precious, pink bunny nose. I want to see a sweet baby bunny not a fussy bunny so you better stop whining unless you want a Princess Pill. The special medicine that shrinks your little thingy and makes you feel little and girly. Maybe you would be more excited to be everyone’s little bunny after a Princess Pill or three.
diaper, imposed fem, humiliation, magic control, mommy roleplay
Download link ----> Made Into A Baby Bunny - May 03, 2019 - 716.37 MB
There is something thrilling about getting a hotel room just to fuck and that goes double when the secret sex is with my darling boy. I have been looking forward to getting your beautiful cock in my holes again and judging by how hard you are, the anticipation has been mutual.
I know you are eager to fuck but I want that stiff dick in my mouth and sliding between my big, soft tits before you get to my pussy. You are going to need to leave Mom utterly orgasm exhausted and delirious if I am going to make it to your next "business trip", AKA our next hotel sex party.
milf, titty fucking, dildo fucking, taboo, mommy roleplay
Download link ----> Hot Hotel Sex with My Son - February 02, 2020 - 549.55 MB
I understand you have come to talk to me about some bullying issues you have been having with the cheerleaders. I know school can very difficult for boys like you who are, um, sensitive let's say. Oh goodness, babydick is a very mean nickname but why would they call you that? I will need to take a quick look before I can decide how to help you confront this harassment so go ahead and unzip your pants for me, dear.
Well then. I see that this a well deserved, if still cruel, nickname for you. I think your best option would be to embrace that you are a bit of a sissy baby and show the other students that you are not ashamed of the truth. I recommend that you be diapered at school at all times moving forward. What is the point of trying to humiliate someone by calling them babydick if they are already wearing diapers openly in front of the whole school? I am going to send you back to class in this cute, puffy diaper and these nursery print plastic panties so everyone can start getting used to your new look. You can always ask your teacher for a pass back to my office when you need a diaper change.
milf, sph, diaper discipline, taboo, teacher fetish
Download link ----> Babydick Diapered At School - March 22, 2019 - 818.26 MB
When you said you wanted to try something kinky for fantasy sex night, I was definitely expecting something more adventurous than a butt plug. Well then show me the rest of it so we can to the orgasms! Oh wow. You are a dirty boy after all. I guess you want to watch your girlfriend powder her pussy and tape a puffy diaper over her big round butt.I am down to be Daddy's diaper slut for the night but then how are you going to fuck me, silly? Good point, I will still have a wet little mouth for Daddy to use after I am all diapered up.
blow jobs, butt plug, daddys girl, diaper fetish
Download link ----> Diapered Blowjob On Date Night - June 07, 2019 - 681.5 MB
Looks like some neglectful husband left his computer at home today with his lonely little wifey. I can’t believe what I found on there, but I LOVE it! Now you’re going to spending more quality time with me, and I’m going to become the Mommy-Dom you’ve been fantasizing about, you dirty AB boy. I strip out of my silk robe and sheer lingerie, pull out the first of your many diapers, and lovingly slide it underneath you. Your thingie becomes painfully erect as I drizzle babyoil all over it and my big soft tits. I stroke you hard while telling you how things are going to be from now on, and your widdle diapered cock erupts cum all over my big Mommy-Dom breasts. I’ve never seen you make so much before, and we’re just getting started, darling!
Three weeks later, you come home to me wearing nothing but an apron and high heels. Did you wet your diaper at work, sweetheart? Too bad, because I won’t change you until after dinner, so let’s get your bib on. You can stand to wear that wet diaper at least until dinner’s over, can’t you, sweetie? I tease while I feed you, exposing my beautiful tits. After dinner I lie you down, give you a sippy cup, strip you naked, and finally change your wet diaper. All this attention makes you marvelously stiff and I can’t help but clean your diapy cock with my loving tongue. Once it’s clean, you pick your next diaper from my new selection and then watch as I destroy the last of your big boy underwear. You’ll never need it again! Finally, I stroke your precious lil’ dick until you shoot a veritable geyser of cum for me, like a good diaper boy. Maybe staying home and coming for your Mommy-Dom should be your new job? XOXO
cum play, diaper, diaper discipline, diaper fetish, femdom pov
Download link ----> Wife Discovers Your ABDL Browser History - December 31, 2021 - 4.57 GB
I can’t believe you asked me for an advance on your allowance. You’re such an irresponsible young man. Now, give me your keys, Step-Mommy needs to borrow your car. I really need to get to work, honey, so just tell me what you want me to do. I give you all the money in my purse and ask you as nicely as possible before you make me strip for you and suck your beautiful cock. Despite my frustration, I let you know how much I enjoy blowing you. It makes me so wet that I agree to let you fuck me and cum in my pussy before you finally go looking for your keys. Thank you for helping Step-Mommy unwind before her big presentation today, sweetie! XOX
pov, cream pie, milf, big tits, taboo
Download link ----> Mommy Fucks You to Borrow Your Car - February 25, 2022 - 3.43 GB
I’m such a lucky sister to have a brother who is willing to be my personal trainer for free. I know how popular you are. You’re always booked solid! And you really get results. Your clients are all in amazing shape! They’re all women, too, I’ve noticed. You must have some special training program to get them so motivated. I wish you’d tell me what it is, even if it is dirty.
That’s when you reveal that it’s a simple reward-penalty system. If you give me a challenge, say 100 crunches, and I can’t do it, then I have to do something for you. However, if I can, then you have to do something for me. It doesn’t sound so kinky until you tell me what the rewards and penalties are: tit fucking, blow jobs, and full penetration of my wet pussy.
You can hardly believe it when I practically start begging you to give me a challenge. You agree, but you’re not going to make it easy on me
exercise, pov sex, sisters, taboo, yoga pants
Download link ----> Personal Training with Sis - January 07, 2018 - 1.72 GB
Masturbating, masturbating, masturbating! That’s all you ever do anymore, sweetie. We could go out, watch a movie, play a board game, but instead you’re taking extra long showers and missing dinner just so you can jerk off. And to top it off you say that I’M the problem for being such a prude!
The next time you see me I’m dressed in a skimpy cow-print bikini, with a matching horned headband, AND a black leather collar with a cow bell dangling over my big tits. Whose the prude now, huh? Hop up on the kitchen counter and let your slutty Mommy see how much she can milk you!
You get on all fours, dangling your massive erection straight down. I cover it in lube and stroke it and suck it while I tease you with my massive tits. You shoot cum all over the counter for me to greedily lick up while I plead for more. You masturbate so much, you must be able to come again. I tie my tits up with pink rope for some extra encouragement and rub your dick all over them until you give me a second dose of delicious jism.
Mommy is so fucking horny. It’s so hot that you can come this much. Please shove that beautiful fat cock into Mommy’s tight, wet pussy! I leave your cum on my tits and let them bounce wildly as you rail me from behind. You make me come over and over until you can’t take it anymore and decide to give Mommy a hot wet cream pie.
I think it’s going to be a lot easier to spend time together now, sweetie. XOXO
blowjob, titty fucking, cum play, pov sex, taboo
Download link ----> Mommy Milkers - October 21, 2022 - 4.02 GB
I wish I could say I am shocked by this terrible report card but your teacher has been dropping hints that you were having trouble focusing in class. Lucky for you, Mom has just the thing to get a young man back on track and laser focused on his goals. You will be wearing this adorable little accessory from now until I see a big improvement in your grades. I bet a smart boy like you can guess what it is for just by looking at the shape.
The chastity device will come off when your grades come up but until then, I am going to make sure every minute in that cock cage is as frustrating as possible. Porn randomly playing on the family TV, slutty little outfits around the house for me, or maybe no clothes at all. If you can back to a B average though, then I promise you will get a special reward when I unlock your cock.
milf, cock tease, taboo, key holding & chastity, mommy roleplay
Download link ----> Cock Locked Up After Bad Report Card - August 18, 2019 - 813.1 MB
You should probably have some idea why we are having this little meeting but I know you are going to be surprised by the key take away. There is a unique program being implemented for low quality performers, like you, and I have been assigned to over see your very special employment probation. Starting now, you will wearing diapers at work. Diapers that I will be changing. Do I look like I'm joking?
You can earn your big boy pants back by showing some improved results or you can lose your job. Unlike you, I take my career very seriously. I will be making certain your diaper probation is humiliating enough to provide plenty of motivation.
handjobs, diaper discipline, femdom pov, office domination
Download link ----> Put On Diaper Probation at Work - November 02, 2019 - 723.89 MB
I know I am wearing yoga pants, sweetie, but Mom is actually trying something called Tantra. It is not just sex yoga, silly. Tantra has many elements like, chakras, crystals, and cock worship. I would really love to show you you instead of just tell you about it. Only if you’re ok with us both getting naked and worshipping each other’s bodies of course.
big tits, taboo, yoga pants, mommy roleplay
Download link ----> Tantric Sex Practice with Mom - November 03, 2019 - 672.67 MB
Watch the full clip in my store or on my OF. XO
anal, milf, jeans fetish, pov sex, mommy roleplay
Download link ----> FREE Mom Jeans POV Anal Sex - January 21, 2021 - 152.87 MB
You’ve been called into the principal’s office—my office—yet again. You aren’t concerned at first, even as the list of your transgressions grows and grows. What’s the worst I could do to you anyway?
Then I pull a diaper bag out from under my desk.
I’ve obtained special permission to humiliate you into behaving better by making you wear diapers in school—in front of everyone!
Time to take drastic measures. You take out the hypnoring you found in your cereal box this morning. You point it at my face and … it works! I fall into a trance, call you Master, and agree to do whatever you say! It’s time to have some fun with this uptight disciplinarian.
You make me strip, completely unaware that anything is out of the ordinary as I continue to berate you. It’s so hot that you start masturbating right there in my office—and I let you!
When I’m down to nothing but my garter, stockings, and heels you command me to explain my dastardly diaper punishment plans as I suck my thumb like a little diaper slut. You don’t mind hearing all the humiliating punishments I had in store for you, because you convince me that the REAL punishment is making you watch me enact every single on of those embarrassing punishments on myself.
At your command, I diaper myself over my lingerie, wet it, and masturbate until I come in my soaking diaper, believing all the while that I’m subjecting you to the most abject humiliations. Could anything make this day better?
Yes: A wet, sensuous blow job from your diapered principal. I suck and tit-fuck your enormous erection whilst explaining what a great administrator I am and how this will all make you a better student. You command me to beg for you to come, and are surprised at what a mewling little diaper slut I’ve become. I beg well enough that you graciously oblige.
Thank god your Mom still buys the cereal that comes with prizes!
diaper, diaper discipline, diaper fetish, mesmerize, woman following orders
Download link ----> Penny Barber - F-ing With the Principal - January 13, 2023 - 3.79 GB
What do a string of vicious attacks in a small town have to do with a lonely, busty single mom and her deadbeat, well-hung son? Plenty.
You can’t tell your mom why you’ve been so lazy lately, missing both class and work to nap on the couch all day. You’re not sure how long you can resist her. She looks absolutely delicious.
MOMMY CLAIMS YOU - Sexy mom sucks your dick, then turns you into her pussy-eating sex toy.
Wearing an unbelievably sexy fishnet bodysuit, your mom seems to have fallen in line. Seemingly eager to obey you, she gets on her knees and sucks your fat, dominant dick, swallowing all your come. But a sassy look has come over her face. Apparently she’s been reading up on vampire lore and discovered a little-known fact: swallowing a vampire’s ejaculate enslaves him to you! She commands you to get on your knees and lick her pussy. She has an orgasm right in your face, her hard clit spasming. You think that being her sex toy might not be so bad, but then she gives you a list of chores to complete before she allows you to feed, all while she relaxes. You decide to do something about it and get back at her for her insolence.
pov, female domination, mind fuck, taboo, vampire
Download link ----> Penny Barber - My Son is a Vampire! Night 2 - October 25, 2023 - 2.58 GB
So you lost the big game today and…kind of humiliated yourself. Mommy is still proud of you for trying. Please don’t give up, sweetie. Let Mommy take car of you tonight before you make up your mind. I prepare the bedroom and remove my silk robe to reveal a red micro bikini. After rubbing your sore muscles, I take my top off and show you what Mommy is willing to do after every game to keep you motivated. I lick your powerful cock while letting you know how badly I want you to be an athlete, and then—when you convince me you’re committed—I let you fuck my proud wet pussy to several screaming orgasms before you give me a hot cream pie. Good boy! XXX
milf, massage, pov sex, taboo, mommy roleplay
Download link ----> Mommy's Pussy is for Athletes - November 18, 2022 - 3.51 GB
You little perv! You may very well be the filthiest, naughtiest client that has ever hired me. I can handle the highly inappropriate questions during my interview; I can even handle finding all the kinky ABDL toys you left around your house, but I draw the line at lowballing me! You clearly need a Step-Mommy-Dom to take you in hand, someone who can control you with her gorgeous, fat MILF breasts.
As I sensually reveal my perfect tits, lifted in my cupless nursing bra, the pacifier I found in your bathroom does an excellent job of keeping you quiet. Despite the meek, little, pacifier-muted noises you make, your cock twitches in anticipation as I slide the crinkly diaper I found “hidden” in your pillowcase under your hips. I don’t want to cover up that pretty cock of yours right away, though. No, I want to make sure you’ll behave yourself. I squeeze and tease your cute lil’ hard on until you spurt warm cum all over my apron. Aren’t you embarrassed to have no self control, little one?
Do you ever pee in your diaper? I tape you up and rub my hands and tits all over the fetishy material covering your crotch. It might be embarrassing, but I want you to wet your diaper your Step-Mommy-Dom. You get hard again in your warm, wet diaper as it’s squished against my big soft tits. I beg you to fill your diaper with cum for me as I rub against your wet, diapered cock. Good boys get orgasms, and as I moan and titty fuck your diaper, you show me what a good boy you can be!
We’re going to have a regular diaper playdate, you and I. So remember: the cleaner your house is the next time I visit, the more time we’ll have to make you come in your diaper again! XOXO
diaper, diaper discipline, diaper fetish, femdom pov, humiliation
Download link ----> Penny Barber - Maid to be My Mommy - May 12, 2023 - 3.37 GB
Watch the full clip in my store! XO
pov, blackmail fantasy, pov sex, taboo, mommy roleplay
Download link ----> FREE Earning Mommy's Engagement Ring - February 07, 2021 - 155.65 MB
You really hate hiking, but damn does Mommy’s ass look good in those jeans! I notice you lagging behind me, checking me out. Does Mommy’s big boy need some relief? We head off to our secret spot and I strip out of everything but my jacket and my hiking boots, my exposed nipples hard and horny.
My whole naked body bobs up and down on your cock as I lick and suck your hard dick and stroke my MILF clit. But Mommy didn’t think ahead and soon you cum all over me. There’s nothing to wipe up with except for my jeans and nothing to do but zip my jacket back up and hope that nobody notices I’m naked as we hike back to the car!
Timestamps:
1:32 Public teasing
2:37 Public stripping
6:55 Outdoor blowjob
18:10 Female masturbation and blowjob
18:37 Cum in mouth, dripping down Mommy’s tits and bush
19:45 Getting ready for the walk of shame
milf, outdoor public blowjobs, outdoors, public outdoor, mommy roleplay
Download link ----> Outdoor Blowjob from Mommy - February 14, 2021 - 2.87 GB
I cannot believe you just tried to take an upskirt picture of me. Did you really think I would not see what you were doing? My short skirt, and what I may choose to wear under it, is definitely none of your business. I might be into diapers but that does not mean you get to perv out on my kinky underwear. Maybe you should get to experience what it feels like to have a picture taken of your diaper without your permission. I know you are not wearing a diaper but I can fix that very easily.
Now you are going to give me your passcode so I can delete those photos of me. Or what? Well, I can think of a few things I can do to embarrass you since you are tied up and wearing a very puffy, very girly diaper right now. But you know I don't just wear diapers, sometimes I use them. I don't see why I should not sit on your face and wet mine right now. I bet that would teach you to keep your eyes off my diapers. Wet Diaper Face Sitting for Peeping Perv
diaper discipline, diaper fetish, face sitting, imposed ejaculations, humiliation
Download link ----> Wet Diaper Face Sitting for Peeping Perv - February 08, 2020 - 689.25 MB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
masturbation, cum in mouth, pov sex, taboo, mommy roleplay
Download link ----> FREE Sick Mother Fucker - August 03, 2022 - 94.57 MB
This custom scenario focuses a bit less on role play and a lot more on silly ABDL fun. I have a favor to ask of Ella my sweet little diapered adult baby girl. I confess that I am wet and need a change from my baby girl. Ella is shocked at first that Mommy sometimes wears diapers too but she starts to enjoy teasing me about needing my diaper changed like a baby. She even stuffs a pacifier in my mouth!
Of course, little Ella can’t make it all the way through the process of undoing my wet diaper and putting a dry one under my bottom without peeing in her own diaper. Ella does not even realize that she wet herself during my diaper change but Mommy always notices.
diaper fetish, taboo, adult babies
Download link ----> Diaper Changing Role Swap with Ella Nova - December 13, 2019 - 1.0 GB
I bet my special man is ready to relax after another hard day's work. Let's get you a nice bottle and take these big boy pants off. These big boy boxers need to go in the trash, in fact. I told you that I am going to keep destroying your grown-up underwear until you have no choice but to wear diapers to the office. You still have a few pairs left, don't worry.
I think I want you in the sissy pink diapers for tonight. You know it is up to Step-Mommy Wife to decide if you get to be a little baby boy or a little baby girl but maybe you can wear your boy diapers tomorrow. You just let me make all the decisions about your diapers. All you have to do is lie back, finish your bottle, and let Step-Mommy help you make a nice big creamy in your first diaper of the weekend.
handjobs, diaper fetish, taboo, sissification
Download link ----> Business Man is Wife's Sissy Baby - April 04, 2020 - 720.03 MB
I got us the cutest costumes for tonight’s halloween party, sweetie! Step-Mommy’s going as a cheerleader and you’re going as… well, there’s a bib, a bonnet, a bottle, and even a diaper! What do you mean it’s too embarrassing? I’ll give you THREE favors if you go with me. First you want to watch Step-Mommy change? I’m a little embarrassed, but I let you watch me strip and put on my slutty cheerleader costume. Then you ask me to dress YOU! Since I’ve done it before, it’s no big deal — even with your hard-on complicating matters. Finally, you ask me to fuck you! Keeping my word, I start by teasing you with my big tits and rubbing my pussy against your soft diaper. After coming on it, I take your hard dick out and slide you into my sensitive wet pussy. I ride you to another delicious orgasm before you come deep inside me.
You’ve used up all your favors and it’s time to go! If you want a dry diaper then you’re going to have to do a favor for Step-Mommy. XOXO
pov, diaper, diaper fetish, pov sex, taboo
Download link ----> Favor for Mommy - October 27, 2021 - 4.6 GB
You always thought that no one could come between your Mom and Dad, but when I run into them during what was supposed to be a romantic weekend away, I prove you wrong! I use your slut of a father, then humiliate your pathetic mother--in public! Pull up a chair as I share all the juicy details with you, whether you want to hear them or not
femdom, cuckolding, humiliation, lesbian domination, taboo
Download link ----> Penny Dominates Your Parents - June 17, 2018 - 1.81 GB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
cream pie, milf, pov sex, taboo, mommy roleplay
Download link ----> FREE Mom Catches You Stealing - March 24, 2023 - 96.74 MB
Of course Mommy will sign your permission slip, sweetie! What is it for? SEX ED!? Hmm. I don’t know if you’re ready for THAT yet. Here’s what, if you can show Mommy that you can get an erection like a big boy, then I’ll sign the form. I’ll even help you by showing you my big titties, my round ass, and my soft pussy. OH MY GOODNESS! That is quite the erection. I never realized what a big beautiful cock you had, darling. Please let Mommy play with it a little. I’m just going to stroke it, kiss it, and rub it against my big tits, okay? Now, If you really want to show Mommy that you are ready for sex ed then you are going to have to fuck me with that big dick of yours until you cum deep in Mommy’s pussy. Good boy!
pov, cream pie, pov sex, taboo, pov blowjob
Download link ----> Sex Ed With Mommy - October 01, 2021 - 4.58 GB
First you fuck up my lunch order, then you fuck up my nail appointment before my date tonight! You have one last chance to be a competent assistant before I fire your ass. Go to my place, pick up my dress for tonight, and bring it back here. That’s it! Think you can handle that?
What took you so long? You went snooping though my…oh no. You found my diapers and my ABDL outfits and took pictures of them? Seems like you get to be the boss for the moment. First you have me strip down to nothing but my heels before telling me to put on the humiliatingly adorable pink diaper you took from my stash. Then you have me write an email with a glowing performance review and a request for your raise while sitting on the floor topless and diapered!
Just as I think I’ve had enough, you tell me to put on my slutty evening dress OVER the diaper. I’ve never been asked to do something so kinky before and my embarrassment spikes my arousal as I acquiesce. Being dressed and treated this way makes me feel soooo submissive. I pose for you as you take dirty photos of me and tell me how hard this is making you. I don’t believe you until you show me, and then I immediately drop to my knees and take your stiff dick in my eager wet mouth.
You take more pictures and I wet my diaper while keeping your beautiful cock locked firmly between my soft lips. You come in my mouth just as my date for the evening calls, and I turn him down as I swallow your warm load. You know, I think that raise is going to come with some new responsibilities, stud. XOXOXO
milf, diaper, diaper discipline, diaper fetish, woman following orders
Download link ----> Mean Boss Becomes Diapered Submissive - April 22, 2022 - 4.54 GB
You're having a wanking good time when I burst into your room and ask what you're doing. You say, "Nothing," but there's only one reason that I know of why a boy would be alone in his room, naked, and on his phone! I snatch your phone and, sure enough, you were looking at satin panty porn!
I'm not surprised, though. Mommy has known about your obsession with satin panties for quite some time. In fact, I'm wearing satin lingerie right now! I strip out of my dress, teasing you and asking if seeing me like this makes you want to jerk off. I encourage you to masturbate while you stare at me--and to wear a pair of satin panties of your own! Now, cum for Mommy like a good little panty ass sniffer!
This is a custom video and includes the name "Scott"
milf, joi, jerk off instruction, panty fetish, satin panties
Download link ----> Mom Knows About Your Satin Panty Fetish - April 15, 2018 - 1.82 GB
I jimmy open Mom's boozeohol cabinet and want to try tequila with you, my brother, for the first time, but you're not so sure. I'm already going to get in a ton of trouble, though, so you'd better man up and do shots with me! Of course, I have no idea how much a shot is. Maybe I overdid it a little? Either way, when you suggest that we play with some sex dice that you have, I'm tipsy enough to go for it. They keep coming up with weird suggestions, though, like "Touch Neck." I think that we can do better than that. Say...fuck my tits?I mean, it hardly counts if we're brother and sister, right? We're just having fun--especially when you cum all over my big, soft breasts
big boobs, pov, big tits, games, sisters
Download link ----> Partying With Your Hot Sister - August 12, 2018 - 1.82 GB
Aw, did I wake you? I just wanted to see how your last big sleepover before college was going. You two have made quite the mess with all this candy, gaming, movies, and pizza. Looks like a good time, but do I smell…pee? Did you have an accident?! Lucky for you, I’m prepared for just such an emergency with a thick, crinkly diaper! Now let’s get you undressed and…oh, my! That is quite an erection you have there. I clean it with my warm, wet mouth—licking and sucking until you give me a load of yummy diaper boy cum. I swallow it like the dirty MILF you never knew I was, and then tape you up for the rest of the night.
The next morning, we have a little time together while your friend is in the shower. Your cock stiffens as I check your diaper only to find that you’re positively soaked. Is that an embarrassment boner? Because I think that you like this, your dirty diaper boy. I tease you as I jerk you off with your wet diaper, but before you can finish I let you thank me for taking care of you by stuffing that fat dick into my tight, hungry pussy. I ride you cowgirl on top of your wet diaper as you beg me to fuck you. You make me come hard on your engorged cock before shooting your hot jizz deep inside of me. Now let’s clean and change you once more, just to be sure you don’t have any accidents on the way home.
Do you mind if I visit you in your dorm next year?
milf, cum in mouth, diaper, diaper fetish, pov sex
Download link ----> Penny Barber - Best Sleepover EVER - April 28, 2023 - 4.43 GB
Watch the full clip in my store! XOX
diaper, humiliation, toilet humiliation, daddy roleplay, car
Download link ----> FREE Penny's Diapered Road Trip - June 26, 2021 - 148.74 MB
Ready to do some yoga with Mommy? I run through a series of sexy stretches and poses as you watch, practically drooling over my MILFy curves, which are accentuated by tight, my hot pink, yoga outfit. You’re barely keeping it together when I insist that you start participating more. You manage to resist, but when I lean in to help you stretch, my bit, MILF tits in your face, you can’t help but get an erection.
But it’s nothing to be embarrassed about, sweetie. And since Mommy made you all stiff, then Mommy can help you get release. I unclasp my sports bra and tell you to stroke your big cock as fast as I play with my big, soft tits. But don’t come yet. Watch me peel the pink leggings and thong off of my round, juicy bottom before sensuously oiling up my breasts and ass.
I know it’s naughty, sweetie, but I really like it. I drip oil onto my pussy and rub my clit in your face while you continue to jerk off to my instructions. I get closer and closer to coming before I can’t wait anymore and countdown to a simultaneous release and you cover my pussy in your jizz as I reach my own screaming orgasm.
Isn’t it fun to stretch it out with Mommy?
striptease, cum countdown, jerk off instruction, taboo, yoga pants
Download link ----> Penny Barber - JOI to Mom's Yoga Body - July 28, 2023 - 4.45 GB
Follow me on Twitter @pamperedpenny
Follow me on Instagram @pampered_penny
Visit my wishlist pamperpenny.com
milf, big tits, cougar, behind the scene
Download link ----> Getting Older in Porn - June 02, 2018 - 1.83 GB
Wearing a white lace bra, panties, garter belt, and stockings I’ve caught you stealing diapers from the hospital. I tease and humiliate you, telling you that I know you’re just a little diaper slut and threaten you with a spanking! I show off my lingerie before slipping into a diaper myself, powdering my pussy and touching myself. I let you watch me wet my diaper before I diaper you, too! I treat you like a babie, even having you nurse from my big, soft breasts while you cum in your diaper. I change out if my diaper while giving you rules for being changed out of yours. Then I change into sexy black lingerie and talk about furthering your diaper punishment, now that you’re my little diapered plaything. As a nurse I’ll be able to provide all the diapers that you widdle babie needs and make sure that you’re breastfed and jerked off daily!
This is a custom video with the name Wesley/Woofy in it
diaper, diaper discipline, diaper fetish, nurse play
Download link ----> Naughty Nurse Catches You Stealing Diape - February 06, 2017 - 1.96 GB
I love showing off my report card to remind you which sibling got all the brains in this house. I am having a great time mocking you with my straight A grades when you say something...strange that makes me feel a little funny. You start to talk about putting "triggers" in my audio books but thinking is so hard and I feel so squirmy in my panties that I just can't understand what you mean. Luckily, you change the subject to something I suddenly care about very much-slutty clothes!
You have brought me some new outfits as a present but you tell me I can only model them for you if I wear my other presents underneath. A stack of adorable, puffy diapers! For some reason, diapering myself and showing off my hot body to my brother sounds like the best idea ever. I can't wait to wiggle my diaper butt in your face while I try on these outfits that leave my tits totally bare. Do you think I should take some diaper selfies for my social media friends too? Duh! What a dumb question. Of course I should show off my cute diapers to as many people as possible!
diaper, diaper fetish, magic control, transformation fantasies, adult babies
Download link ----> Smart Sis Transformed Into Diaper Ditz - January 18, 2019 - 1.45 GB
When I rented this room to a strapping young man, I never thought to ask if you were a bedwetter. My mistake, I guess. I am not even sure how many nights in a row you have had an accident but that mattress is expensive and I can’t have you running up the water bill washing your sheets every single morning. After doing a little internet research, I have decided that the best course of action would be for you to spend your nights in diapers from now on. It’s not like I want you to be diapered but it certainly is not my fault that you wake up in a puddle of pee every morning. It is just an unexplainable mystery why this never happened before you moved here. Now strip naked so I can powder that nice, young cock. Strictly for practical reasons, of course.
I hope you can get these night time accidents under control soon because I would just hate to have to take the next step if you can’t stop wetting the bed. It would just be so embarrassing if you had to be diapered 24/7
milf, diaper discipline, diaper fetish, embarrassment, pee
Download link ----> Tricked Into Diaper By MILF Landlady - September 06, 2019 - 734.04 MB
Find the full video in my store! XO This video was voted on by my Twitter followers. To vote on future content, follow me on Twitter @pamperedpenny XOX
big toys, femdom pov, jerk off instruction, taboo, mommy roleplay
Download link ----> French Mom Squirts as You Stroke Trailer - December 02, 2020 - 122.36 MB
What could be more humiliating than getting caught with your hands in your shorts at a public pool? Maybe if your fellow lifeguard discovered you were wearing her stolen pink panties under your trunks and then sent you back to the pool in just a diaper? I was not really surprised Ella complained that Sam was touching himself and staring at her bikini covered ass instead of looking out for the safety of all swimmers. I definitely was surprised when we dragged him inside and saw that he was wearing a pair of my panties that had gone missing from my locker. We have a great time laughing at the little panty perv and teasing his tiny cock but mockery and blue balls is not a worthy punishment for public masturbation. Ella and I both agree that boys with baby dicks and no self-control definitely belong in diapers.
ass humiliation, cock tease, diaper discipline, female domination, sissification
Download link ----> Pool Perv Diapered by Penny and Ella - July 24, 2020 - 645.06 MB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
milf, diaper, diaper discipline, diaper fetish, femdom pov
Download link ----> FREE - Maid to be My Mommy - May 12, 2023 - 140.64 MB
A Penny Barber Fantasy. Watch the full clip in my store! XOX Follow me on Twitter.com/PamperedPenny
cream pie, milf, squirt, pov sex, taboo
Download link ----> FREE Mom Fucks You at Your Sleepover - July 30, 2022 - 1.56 GB
Find the full clip in my store! XO
pov, diaper, diaper discipline, diaper fetish, femdom pov
Download link ----> FREE Diapered by Your Crush - July 10, 2021 - 144.44 MB
I want to give my special boy a special treat today. I want you lie back so Step-Mom can give the sweetest and softest strokes to that adorable cock of yours. I am going to put on my white gloves after I take off your underwear but before I touch your stiffy. I am also going to create a little pillow of soft tissue for your cock to rest on while I spoil it with attention. I want everything to be so soft and gentle that by the time I take you over the edge its feels like you are cumming into a cloud.
handjobs, glove fetish, taboo, mommy roleplay
Download link ----> Soft Glove Handjob from Step-Mom - August 02, 2020 - 768.17 MB
I am not going to tolerate your lewd staring in my classroom any longer. I do not want to hear excuses for your behavior or blaming my appearance for your choices. From now on, I expect...
What was that sweetheart? I guess I lost my train of thought. Would you like some tea? How about some cookies? I only have store bought but I promise they will be homemade next time. I just want my darling to be happy and healthy. Is there anything else....
Nevermind, sweetie, I have something more important we should talk about. Mommy is starting to get very horny and she needs your help. Don't you like the way my body looks? Maybe if I just take off some clothes so you can see as much of me as you like. I am not sure why you are hesitating to fuck me right here on this desk but will you at least show mom your nice hard cock? Pretty please?
milf, joi, magic control, taboo, transformation fantasies
Download link ----> MILF Teacher Transformed Into Slutty Mom - March 31, 2019 - 735.48 MB
Almost every porn star gets tons of emails from losers asking how they can get into the industry. We don't usually get those kinds of messages from sexy guys with big four and a half-inch dicks like you, though. You are totally the exception to the rule and I am so excited to shoot some content with you. We just need to get you ready first. I need you to slip into this locking cock sheath and then I can add this special outer cover. I will explain it all after we get you set up.
Wow, I cannot believe you are so gullible. Did you really think your dick was big? Well, now that I have you in chastity and diapers we can launch your porn career. I hope you are still excited to be my co-star as a pathetic adult baby in diaper fetish videos.
latex, sph, diaper fetish, jeans/pants wetting, chastity
Download link ----> Tricked into Wetting Yourself - May 01, 2020 - 722.03 MB
I was really looking forward to having you and Ella all to myself for a few months but that won't happen if you two are partying with your friends the whole time. That's why you will be both be spending your vacation in diapers. Instead of willful young adults I will get to have two obedient and adorable little babies to play with all the time. If you try to resist or talk back then Step-Mommy has plenty of rope and tape to keep you still and quiet.
I have big fluffy diapers and cute little pink outfits in both your sizes. You will both be dressed up like precious sissies and have your diapers changed in front of each other so no need to be shy. Maybe it will be a bit more embarrassing for you when Ella sees you in girl clothes getting your sweet little winkie powdered but I still don't want to see any pouting. All I want to see are two tied up adults babies helplessly creaming their diapers.
bondage, diaper fetish, feminization, taboo
Download link ----> Mommy's ABDL Plans for You and Ella Nova - September 18, 2020 - 569.09 MB
I came up with the best Halloween costumes for this year’s contest. Since we’re having to do this over Zoom, I thought, why not go all out and wear something that we could never get away with wearing in public? And the theme for this year is supposed to be “Dye of Embarrassment!” So, here’s the plan: We both go...in diapers! Like, literally, when it’s our turn to show off our costumes, we both...just...wet ourselves! We’re certain to win! I used to always win--but then last year you refused to put on the matching princess dresses I got for us. My ex boyfriend and I always used to win, you know. So...you kind of owe me. Now put on your diaper! (And your lucky butt plug.) After we win I might just be so pleased with you that I spread my diapered legs for your eager, pee-covered cock.
diaper, diaper fetish, taboo, adult babies
Download link ----> Diapered w/Girlfrien for Costume Contest - November 05, 2020 - 1.76 GB
I bet you are wishing we could slip in some special alone time on this camping trip but there really is not much privacy out here. I suppose there is not really anyone around right now so I can at least give you a little peek at my bare tits. Just a quick look, though, You don't want someone to catch you jerking off to your topless Step-Mom. I certainly don't want anyone to catch me fingering my pussy while I spread my ass for you so I guess I better do it pretty quickly. Teasing you always gets me so wet but if I am taking all these risks then it is only fair that you take out your cock and stroke it for me too. I might be willing to put that hard dick in my mouth but only if you have the courage to take it out in the open air first.
milf, public nudity, taboo, mommy roleplay, pov blowjob
Download link ----> Camping Blowjob From Mom - September 27, 2020 - 570.64 MB
I am so excited to be your new nurse and I hope you are excited too, little one. I see that you are out of your diapers for some reason but we can fix that. I have your file right here and it definitely says you are a girl and that you still wear diapers. I am the nurse and you are the patient so I don't want to hear anymore fussing. You are going to wear this nice, fluffy diaper for Nurse Penny and stop telling stories about being a grown up man. See, this little thingy of yours is way too small to be a penis so you must be a baby girl who belongs in diapers. If you want to keep arguing then I can just stick a pacifier in that little mouth of yours.
Now, it also says in your chart that I need to make sure you are dressed appropriately and that I should expect you to go through a lot of diapers. I can take care of your clothes but it seems your diaper is still dry for some reason. Is the naughty girl trying to be willful and not wet in front of Nurse Penny?
sph, diaper, feminization, nurse play, taboo
Download link ----> Nurse Penny Decides You're A Diaper Girl - July 26, 2019 - 332.92 MB
On a whim, I decided to check your browser history and it seems that Mommie raised a little panty fetishist. But I started thinking and instead of finding your humiliating secret, I think that I may have found a means of motivating and controlling you. How strong is your panty fetish anyway? What if it’s your M0m wearing them? What if I just take off my robe, stand up, turn around, and show you my pretty, pink lace panties? Oh my. Are you trembling?
I try on 5 different pairs of panties until I find the best ones for controlling and motivating you. From satin bikini cut to polka dot thongs, I make you watch as I try on all these different panties so that I can measure your reactions (i.e. stroke speed) and turn you into my devoted little panty worshipper. Now, come give Mommie’s panties a nice, long lick. I make you put on a pair of my panties and watch me masturbate before you tribute my panties with your cum as we simultaneously orgasm
joi, panty fetish, pov sex, taboo
Download link ----> Mommie Exploits Your Panty Fetish - March 21, 2017 - 1.78 GB
I am excited about all the fun we can have tonight but I do have a question about all this adorable stuff I found. I don't see why your Step-Mommy would leave all these diaper changing supplies right here if she didn't want me to find them. A bedwetting problem would explain why she hired a babysitter for a boy your age.
Honestly, I think these diapers are totally cute and it is really precious how shy you are about needing them. Maybe we should put you in one right now, just to get the embarrassment out of the way. Lie down and take off all your clothes like a polite and obedient little bedwetter. If you do everything that your babysitter says then I might even let you have a special big boy treat in your diaper before I am done playing with you.
joi, diaper, diaper discipline, diaper fetish, femdom pov
Download link ----> Babysitter Makes You Wank in Diapers - July 22, 2022 - 1.01 GB
I have been wondering where all my socks went to and it looks like you have been taking them all on a little trip to wank town. Don’t try to deny it. I just caught you with your pants down surrounded by a big pile of my socks.
I never knew my son was a little foot prevent but it is almost cute that your cock is so hard over Mom’s dirty socks. If you like MILF socks so much maybe I should slip on some of the dirtiest ones from your little collection for a sock footjob.
foot fetish, footjobs, sock smelling, sockjobs, socks
Download link ----> Footjob with Mom's Dirty Socks - December 25, 2019 - 1.77 GB
I lost my glasses while looking for clues to a mystery but in my search for those missing spectacles I stumbled upon something wet and squishy. What could it be? Luckily, I found my glasses in time to discover the source of the dampness was none other than the crotch of your jeans. You probably would have gotten away with wetting yourself if it had not been for me snooping around but since I am here now, I may as well help you out.
First we take off these jeans and then we put on this diaper. Of course you need a diaper, what else would a pants wetter wear? I mean, even if I had not found you sitting in your own pee, just the sight of your thingy makes me think it probably belongs in a diaper. I am no expert but yours looks pretty small and dinky. Still kind of fun to play with while I am diapering you though. I wonder what else might be fun to do with your little thingy before I tape it up in your diaper and get back to my very important case.
handjobs, sph, diaper discipline, femdom sex, jeans/pants wetting
Download link ----> Velma Solves Mystery Of Mister Pee Pants - May 18, 2019 - 707.17 MB
Just some good, old fashioned POV diaper sex! I have two diapers and I want us both to wear them while we fuck and play. You know you've fantasized about this: being in my room with me all hot and bothered and eager to diaper you, looking sexy in nothing but my cute, pink DC Amor diaper. Let's play
pov, diaper, diaper discipline, diaper fetish, pov sex
Download link ----> Diaper Girlfriend Experience - June 29, 2018 - 1.82 GB
You've started overflowing the pullups that I, your step-Mommy, put you into, soaking your sheets every night, despite being technically diapered. So I've come up with some new rules to hopefully embarrass you into keeping your sheets dry--or at least make sure that your diaper is absorbent enough! To start, I've rearranged your underwear a little bit. I got rid of all your boxers. Now it's pullups during the day and full, bulky, padded ABDL diapers (Tykables Overnights, to be specific) at night! But your regression punishment goes much further, I explain as I unbutton my sweater and expose my breasts. So...much...further.
Diaper handjob, ABDL, adult nursing, humiliation, regression, step-mom, mommy dom, POV
diaper, diaper discipline, diaper fetish, taboo, mommy roleplay
Download link ----> Mommy's New Diaper Rules - September 16, 2020 - 1.81 GB
You left your phone unattended last night and I found some pretty incriminating stuff on it, namely pictures of some red-headed, big-breasted slut named Andrea. Well, I think I know just what to do with her. I pretend to be you and lure her into sending me some slutty pictures so that I can break into her apartment and catch her redhanded! She’s shocked to see me and get pretty fussy, but I wrestle her out of her slutty little outfit, bind her hands and then make her pose for a bunch of humiliating pictures, which I send to your phone and mine. I’m going to have so much bl@ckmail evidence on her that she’s never going to want to be the side chick ever again
blackmail fantasy, diaper, diaper discipline, diaper fetish
Download link ----> Side Chick Diapered by Angry Girlfriend - January 20, 2017 - 1.41 GB
It’s your first day back at work after lockdown and you’re excited because that means no more diapers! Ever since you’ve been home, I’ve been keeping you in them 24/7, but nobody said anything about underpants to work—or ever again! You’re really fussy about it, but I manage to calm you down with a diaper-change handjob while you’re mesmerized by my big, warm boobies.
Everything seems to be going fine at the office and you think you may have gotten away with it, until you find me waiting in your office. You really should get a secretary to stop people from just wandering in like this, darling. I’ve brought you some snacks and a fresh, new diaper! You can act fussy all you want, but you can’t hide how excited all of this makes you. As I change your sopping wet diaper, I realize that I left the wipes at home and proceed to lick your pee-soaked cock clean. I get so excited that I strip down and fuck you right on the floor of your new office, making you suck your thumb and enjoy your bottle before letting you fill my hot wet pussy with your cum.
You know, I really should be here to change your diaper whenever you need it, and I noticed that you still don’t have a sexcretary--er, secretary.
pov, cum play, diaper, diaper discipline, diaper fetish
Download link ----> Diaper Sex at Work - September 09, 2022 - 4.52 GB
Available 10/21! Watch here on my ManyVids. XO
milf, older woman / younger man ., pov sex, taboo, mommy roleplay
Download link ----> Are You My Mommy? Extended Trailer - October 19, 2020 - 178.96 MB
Watch the full clip in my store. XO
feet, milf, stocking, pantyhose, mommy roleplay
Download link ----> FREE Cheating Mommy Takes Control - July 02, 2021 - 231.05 MB
I am so happy that my little man has found a great girl with a huge cock, just like mine. I always taught Sam that his place in the world is as a cocksucking servant to the superior futa females in his life and that is why I know Ella is just the perfect dickgirl for him.
Even the happiest families can experience a little holiday tension though so when Ella suggests that she has bigger cock than me, it almost turns into a full blown futanari family feud! The only way to settle this size matter peacefully is obviously a double blowjob from Sammy. He is going to take his futa facefucking like a good boy and then let Ella and I know which one has the biggest dick. Poor Sammy is going to end up with a very upset Mommy or a pissed off girlfriend but at least he will get to worship two giant futa cocks first!
sph, role play, futa, futanari, taboo
Download link ----> Futa Family Holidays With Ella Nova - January 20, 2019 - 1007.46 MB
Watch the full clip in my store! XOX Follow me on Twitter.com/pamperedpenny
cream pie, diaper, diaper fetish, pee, public flashing
Download link ----> FREE Diaper Date Cream Pie - July 22, 2021 - 176.87 MB
My new secretary, trans girl cutie Natalie Mars, is barely competent but very pretty so I tolerate her little mistakes like missing a meeting, forgetting an appointment or accidentally shipping a giant butt plug, diapers, and a whole box of other adult baby supplies to the office. As soon as I ask her why a box addressed to “Baby Natalie” has arrived on my desk, she clearly panics in desperation to avoid me seeing the contents of this mystery box. Of course I open it anyway and find so many naughty fetish outfits and accessories, including diapers that look like they would fit her perfectly. I laugh in her face but I am secretly thrilled at this opportunity to humiliate my cute little assistant and for a great excuse to get her naked.
I still want Natalie as my secretary but I think her new title will be Office Diaper Slut. From now on she will be sitting at her desk in frilly baby dresses, having to take out her pacifier to answer calls, and pretty much spending all working hours plugged in a wet diaper.
butt plug, diaper fetish, humiliation, office domination, trans
Download link ----> Natalie Mars Demoted Office Diaper Slut - April 26, 2019 - 727.33 MB
I wonder what you did that make your parents hire a sitter for a college boy. Is the embarrassment of being supervised by a pretty girl part of your punishment or are you just too innocent to be left alone? Judging by how easy it is for me to make you blush I am guessing it is a little of both. Let's play a game before you start to bore me too much, the game is called Naive College Boy Learns to Jerk Off. I am sure you're going to love playing this with me every time I babysit you.
femdom, old & young, fetish
Download link ----> Too Old For A Babysitter - March 29, 2016 - 1.28 GB
I hope you know that I am very proud of your recent success but don’t you think you might be getting a little carried with all the custom suits and always flashing your cash around. I am sure it is quite stressful to work such a high pressure job but I am not sure spending so much money on fancy watches is going to help. Of course I would love to hear your idea for better ways to spend your money and relieve your stress, honey. Wait what? One hundred dollars… for a blowjob… from me?
I thought you were joking but that big, hard cock tells me you’re serious. I guess a hundred bucks for one blowjob isn’t that bad of a deal. What if I strip naked and then you can decide if you really want Mom to suck your dick for money.
pov, financial domination, blow jobs, taboo, mommy roleplay
Download link ----> Bribing Mom For A Blowjob - September 29, 2019 - 742.67 MB
Honey, I have a very important meeting today and need you to pick up some black pantyhose for me. Can you do that? I don’t care where you get them, just hurry!
You come home to catch me engaging in some weird, pep talk masturbation. You watch for as long as you can, but it isn’t long before I see you spying. I’m absolutely embarrassed that my step-son would watch me do that, but I am running late, so I just grab the pantyhose and slip them on — as you continue watching me through a crack in the door.
But before I can put my suit on, some invisible energy suddenly takes control of my body! It bends me over my dresser—giving you an eyeful of my round, nylon-clad ass—and then makes me start gyrating my hips as some phantom pleasure begins to course through me, making my wet pussy contract in a way that feels even better than my vibrator! As you secretly watch, I come so hard that I need to catch my breath before truly regaining my senses.
I call for your help as I try (and fail) to remove the eerie undergarment. You attempt to read the instructions, but they are in some strange language that neither of us can understand. Even though my step-son is in the room, I can’t help but open my secret drawer full of sex toys. The diabolical hosiery makes me lay before you step-Mommy’s vibrator, butt plug, clothes pins, and a rose gold submissive collar. You watch me collar myself, then clip the clothes pins onto my fully erect nipples. I beg for help, but it’s just too much fun to watch! You’re even getting hard. Every time I finish doing something the pantyhose want me to do I receive a jolt of pleasure in my pussy and moan like a wanton slut right before your eyes.
Why aren’t you helping me, sweetie!? Oh! These pantyhose are going to make me masturbate in front of my own step-son! Instead of going to get help, you take off your clothes as I’m made to vibrate my sensitive clitoris to multiple screaming orgasms. It seems like these…things…are trying to pacify me with kinky sex.
Just as I start to recover and think the nightmare might be over, I grab my own hair and push my face onto your fully engorged cock. Whenever I try to chastise you for going along with the underwear, I interrupt myself by blowing you hard and fast. The more I please your hard cock, the better it makes my pussy and clit feel until I inevitably give up and agree to do whatever you and the hosiery want me to do.
You remove the clips from my nipples before plugging my ass and laying me down to give you a submissive footjob. My feet are soft against your stiff erection, and the more I use them to pleasure you, the better they begin to feel until they are as sensitive as my pussy and it feel like I’m fucking you. I come twice more before you ejaculate all over the crotch of my malicious pantyhose.
Do you think they’ll ever let me take them off?!
imposed orgasms, magic control, pantyhose footjobs, pantyhose, taboo
Download link ----> Penny Barber - Controlling Top Pantyhose - June 23, 2023 - 1.79 GB
You seem to have developed a big crush on Mommy. You can’t even watch me watering the lawn in my bikini without getting hard! You’re lucky that you have a Mommy that knows exactly what you need when this happens. I’ll use my big tits you love so much to make you as hard as possible before I give you a dreamy-eyed blowjob right in our back yard. Before you fuck me again, I want you to jerk off while you watch me masturbate until I squirt all over the lawn. Good boy! Now come here and fuck Mommy like she deserves for wearing her slutty bikinis in front of you all day. Do it all over my tits and face! Now put your cock away before the neighbors see it. We don’t want rumors to spread now, do we?
milf, outdoors, pov sex, taboo, cum on tits
Download link ----> Very Inappropriate Afternoon With Mommy - August 01, 2021 - 2.57 GB
It’s morning and my diaper is soaked, Daddy! I need you to change me and I know how to make it extra fun. I strip out of my Disney princess jammies, showing you just how soaked my Tykables overnight diaper is. See how much I need a change? I baby talk to you with my paci in my mouth, rubbing my diaper as I tell you just how to touch my wet diaper as you stroke your cock. I show you just where I want your sticky sweet cum to go on my diaper before scooping it off and playing with it. It’s so gooey, Daddy! I wonder what Daddy’s cum tastes like, so I dip my pacifier in it. Yummy! But I do still need that diaper change. You know, I bet Daddy’s cum would make good baby oil, too
daddys girl, diaper, diaper fetish, taboo, daddy roleplay
Download link ----> Wet Diaper JOI with Daddy - January 05, 2018 - 1.81 GB
This hot pink lingerie I’m wearing is a little embarrassing, but I want you to see what I’m willing to wear to get you excited… because I want to try something new. I want to put you in a diaper. You hesitantly agree, and I perform a sexy little showing of your options. You pick the biggest and fluffiest of the bunch and I tease you into it, playfully massaging my big tits and giving your penis lots of attention. I cover your cock and my breasts with oil before taping you up and mounting you. Rubbing my increasingly wet pussy all over your rock hard diapered dick, I beg you to pee in it. The warmth of your pee on my pussy makes me come harder than ever! I continue to stroke and ride you over the diaper until you’re ready to come, and the pulse of your ejaculation gives me another wild orgasm.
Thank you for being brave, sweetie. How about next time you call me… Mommy!
pov, milf, diaper, diaper discipline, diaper fetish
Download link ----> Seduced Into Diapers - September 03, 2021 - 4.52 GB
All the ladies in the neighborhood are into this kinky new trend and I really want to try it with you. I want to train you to become my submissive little adult baby boy. I want to put you in diapers, make you suck on baby bottles and even crawl on the floor. That way I get to look down at your big diapered bottom and you get to look up at my pussy in whatever lingerie I am wearing that day. Doesn't the idea of me covering your cock in baby powder and lotion sound at least a little bit exciting? I think embarrassing and controlling you with diapers sounds very exciting.
lace/lingerie, big tits, cock tease, diaper fetish, humiliation
Download link ----> Wife Regresses Hubby Into Adult Baby - August 29, 2020 - 464.56 MB
What would you do if you discovered your smoking hot mom was leading a double life as a world famous masked villain? I slipped up while slipping off my suit and now you know my secret identity. I know it is shocking but this has to stay between us. Even if that means I have to trade your silence for a super villain blowjob!
Wearing just my gloves and mask, I put on a little show for you by playing with my bare breasts and pussy so your cock is ready for what comes next. You will be thrilled at having a master criminal for a Mom once I’m done with your dick.
milf, blackmail fantasy, cosplay, taboo, mommy roleplay
Download link ----> Sexy Mom Is Secretly A Super Villain - July 28, 2019 - 489.06 MB
It was almost too easy tricking you into humiliating yourself just to keep your sad little lie going. I already knew you had been cheating but finding your little slut's panties in our bed was the final proof. I thought it would be funny to pretend I thought they were yours just to see what you would do. Which would you rather admit to: fucking someone else in our bed or being a little sissy who dresses up in frilly pink panties behind his wife's back?
femdom, fetish
Download link ----> Cheater Tricked Into Sissyhood - January 05, 2016 - 280.47 MB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
milf, diaper, diaper discipline, diaper fetish, mommy roleplay
Download link ----> FREE Still Mommy's Diaper Boy - March 13, 2023 - 201.46 MB
One conversation that I hoped I would never have is a discussion of my step-son’s unsolicited dick pics. I just talked to a girl who was pretty upset to see your cock on her phone. Oh, they were not really from you? Then take your dick out so I can snap some photos for comparison.
I know it was you but I understand that my little sweetheart is just oversexed. Step-Mom can certainly help give your adorable erection the attention it obviously craves. You can empty those balls right in my pussy... and then you’re going straight into chastity! That is right, little mister, and locking up your cock is just the first part of your dick pic punishment.
big tits, pov sex, taboo, mommy roleplay, chastity
Download link ----> Mom Fucks You & Locks You in Chastity - May 03, 2020 - 587.02 MB
Can you imagine how I felt when I realized your teacher was trying to tell me that you were LOOKING AT PORN IN SCHOOL! Not just some nude pics but kinky stuff about men being penetrated by strap-ons? I should not have been surprised to find this butt plug in your room after that conversation but I certainly was not pleased. Since you like strap-ons and taking things up your butt so much maybe you should find out what is really like to get fucked in the ass. Even if you are not too ashamed to be looking at strap-on porn during class maybe a punishment pegging from Mommy will embarrass some sense into you.
strap-on, role play, corporal punishment, pov strapon, taboo
Download link ----> Strap-On Punishment For Mommy's Perv - February 03, 2019 - 991.56 MB
I need you to hop up, get out of these jeans and into your Sunday suit before you make us late. I will give you your Easter present now if you promise to hurry. I know you are too old for an egg hunt but these say they are for adults. Oh wait, these aren't fun Easter eggs, these are sex toys! I guess you stick your thing inside the egg?
We should test this one out just to be sure but then we really need to run along to church. Oh that just slides right on there, doesn't it. So stretchy and slippery on your nice stiff cock. This toy is actually pretty fun for Mom and it looks you are definitely enjoying it too. We are running late though so I need you to enjoy it a little faster. Maybe the sight of my bare breasts and wet pussy will help you cream your egg a little quicker.
handjobs, milf, big tits, taboo, mommy roleplay
Download link ----> Special Easter Holiday Handjob From Mom - May 26, 2019 - 781.79 MB
Are you going to be a good baby for your nurse today? I plan to put a lot of fun stuff in your bottom (for medical reasons, of course) but first, I have to put on my shiny latex gloves. Then I can get you ready for your diaper, enema, and butt plug. If you want to be a fussy baby about any of my plans for you then I can just demonstrate some of my favorite punishments for naughty patients.
I find that few things make bratty boys feel more submissive and vulnerable than being fucked on their open diaper while trying to hold an enema.
diaper fetish, glove fetish, nurse play, taboo
Download link ----> Nurse Barber has Plans for Your Bottom - April 17, 2020 - 666.09 MB
My friend Lita thinks that we are a lame couple because we don't want to go out to a club so I think we should show her your diaper. I just want my friend to know I am your kinky Mommydomme, not your boring wifey. I bet she has never seen a grown man in embarrassing baby diapers or a tiny cock all locked up in chastity.
I told you she would think it was cool that I control your orgasms and make you wear diapers. Lita is only teasing you about having a small dick and being a diaper boy because I was doing it first. She just wants to be included in our fun. I bet if you ask really nicely she might even want to be included in helping you make a creamy after we change your wet diaper.
sph, blow jobs, diaper fetish, femdom pov, chastity
Download link ----> Diaper Blowjob from Penny and Lita - May 09, 2020 - 829.8 MB
I keep finding your socks and underwear all stiff in the laundry, sweetie. Step-Mommy’s panties are NEVER sticky! I take them off in front of you, bending over and showing you my creamy pussy as I do and — oh wow! Since Step-Mommy was wrong, I’ll do any one thing you want. You take out your dick and tell me to give you a blowjob. Fascinated by your beautiful cock, I tease it with my hands, mouth, tits, and dirty panties, but I don’t make you cum. We have to finish the laundry, silly! As I load the machine with your dirty laundry, I crawl into to check if anything is missing and teasingly wiggle my round ass at you. Fed up, you take your dick back out and fuck me right there on the floor, half buried in the machine. I come surrounded by the scent of your sweat and semen on the laundry as you pound my pussy from behind. You finish by giving me a big wet cream pie. Now Step-Mommy has to clean two of your loads! XOXO
pov, pov sex, taboo, creampie, pov blowjob
Download link ----> Mommy Takes Your Big Load - October 16, 2021 - 3.44 GB
You’re trying to study when you realize that your sister isn’t wearing any panties under her cheerleader uniform. You try to focus, but she’s teasing you on purpose. When she starts openly spreading her legs, dripping baby oil onto her little diamond clit, and playing with herself you decide to give her what she so clearly wants. Your hard cock in her warm mouth and up her tight pussy. Maybe you’re not so mad at her for distracting you after all
cheerleaders, cock tease, pov sex, sisters, taboo
Download link ----> Cheerleader Sister Teases You Until - December 03, 2017 - 1.75 GB
You’re nervous about your big date tonight, so you come into my room to find me touching up my pedicure and lotioning up my sexy feet. I ask you what’s wrong and it takes you a minute to tell me, but…you’re worried that you’ll get hard on your date. I ask you if you’ve jerked off and you admit that you’re just too nervous. I laugh and tell you that I would give you a hand job if I could, but I am your MOM. Although…maybe if I don’t touch it with my hands it’s okay. I strip out of my robe and nightie and play with your hard cock with my slippery feet, stroking your thick shaft with my soles, showing you my pussy and my toes at the same time, playing with my breasts and begging you to splatter my feet with your warm come. You can’t believe what a foot slut Mommy is and finally cum all over my gorgeous feet and sexy red pedicure just as the doorbell rings. Have fun tonight, sweetie!
feet, barefoot, foot play, footjobs, mommy roleplay
Download link ----> Footjob from Mommy - June 18, 2021 - 2.44 GB
I’ve had it with your messy habits in the bathroom—especially the pee all over the toilet seat and floor. So, I took to the Internet to find some very innovative solutions to dealing with a grown man who simply won’t use the toilet properly. It turns out that there are two amazing motivators: sex and…diapers. After all, men like you are really quite simple. You just want a strong, sexy woman to say what’s what and teach you to be a good little diaper boy. It’s all about reward and punishment, pleasure and humiliation. I’m going to take charge of you and your cute little cock for as long as we’re living together, Roomie!
Timestamps:
2:59 Teasing with my breasts
6:29 The new rules
6:51 SPH small penis humiliation
10:33 Showing you my panties
11:36 Diapering
13:58 Rewarding you with my panties and ass worship
16:22 Rewarding you with my big tits
17:49 Stroking you in your diaper
19:32 Blackmailing you with cell phone pictures
20:46 Baby powdering my big boobs
22:32 Vibrating my clit while you hump your diaper
24:50 Exposing my pussy, using the Hitachi
28:06 I cum with my vibrator while you cum in your diaper
diaper, diaper discipline, diaper fetish, femdom pov, humiliation
Download link ----> Roommate's Diaper Punishment - February 22, 2021 - 4.17 GB
I know you have been playing around in my room, little brother. Did you think I would not notice all those missing bras and panties? I definitely did, but I wonder if you have you noticed any personal changes of your own lately. Maybe certain parts of your body getting softer and certain other parts getting... smaller? HA!
I have been slipping a little special something into your system that will make all those stolen panties fit much better. Your butt is going to be getting fatter but that bulge is going to be getting even tiner. Do you still have a crush on your big sister even though I made your dick so little?
sph, feminization, panty fetish, taboo, transformation fantasies
Download link ----> Evil Sister Shrinks Your Dick - August 11, 2019 - 393.93 MB
Are you staring at Mommy’s tits again? God, you are so obsessed with my breasts. How about I let you fuck my tits just once, exactly the way that you want. You can cum anywhere that you like. Will that let you get it out of your system? The proviso is that I’m off the hook for buying you that expensive new video game that you wanted. A lot of guys would be ecstatic to titty fuck their own mom—at least, they would if she had tits like mine. Deal? Good! I strip out of my bra and lube up my breasts. They’re so slick and big that they just swallow your dick. I hump you with my tits and encourage you to fuck them until you have an explosive orgasm in my mouth. Oh my god…your cum is delicious. Maybe we’ll do this again after all
milf, titty fucking, taboo
Download link ----> Titty Fucking Mom - September 17, 2017 - 1.75 GB
I am not at all surprised to hear about these diaper dreams you have been having recently. I have been doing this a long time and I got a very specific feeling about you from our first session. I have been bringing diapers in your size ever since that first week, just waiting for you to bring it up. I think it would be very helpful if I put you in one right now so we can talk about how it makes you feel.
Please, there is no need to be embarrassed at all. This might be a bit unprofessional but I personally think you look very cute in just a diaper. Your thingy is obviously a bit on the small side but it becomes absolutely precious when wrapped up tight in a big puffy diaper. If you really think I am just humoring you then I suppose I will just have to prove to you that my pussy is indeed quite wet.
blackmail fantasy, blow jobs, taboo, mommy roleplay, pov blowjob
Download link ----> Therapist Cums After Diapering You - August 21, 2020 - 622.06 MB
I really don’t like these new late night habits of yours. We are not spending enough quality time together and I just don’t what you could be getting up to at all hours of the night. Does somebody need a reminder that Mom is in control, at least until you find a wife.
I am supposed to be in charge of what you wear, what you eat, what you do, and who you do it with. I used to control all your functions, even your breath. Maybe you need a reminder of what that level of control feels like. I think being smooshed by my big soft tits and firm round ass is just the attitude adjustment you need. We both know being squished by Mom’s breasts and bottom is so much nicer than partying all night with your loser friends.
ass smooshing, breast smothering, taboo, mommy roleplay
Download link ----> Squished by Mom's Tits and Ass - November 29, 2019 - 660.53 MB
We asked you to show up a little early because I need to get you ready to entertain everyone. You did not think my step-step-son and all his jock friends wanted you to actually party with them? No, sweetie, you are just here as a little femboy party favor. I am going to get you all pretty and sissified so those boys have a blowjob doll for the night.
I will do your make-up while you pick out some cute lingerie to wear. Then we need to get that cute little ass filled by this pretty pink plug. Go ahead and give it a little lick so I can slide it in easier for you. The butt plug might be a tight fit but some of the boys coming over are much bigger so you will be glad to have your hole warmed up beforehand, trust me.
pov, humiliation, sissy training, taboo, sissification
Download link ----> Making You Into My Son's Sissy Sex Toy - July 01, 2022 - 759.5 MB
Busty, brunette MILF Penny Barber talks about her breast implants, from funding them on MyFreeImplants.com to what it was like waking up during surgery to her future plans for her boobs.
Follow me on Twitter @pamperedpenny
https://twitter.com/pamperedpenny
xoxo,
Penny Barber
big boobs, milf, big tits, behind the scene, vlog
Download link ----> My Breast Implants - March 01, 2019 - 1.76 GB
Mommy is going to give herself a little spa-night, sweetie. I picked up this wonderful new “Hand Job” lotion at the store. What do you mean that’s dirty? It’s not for sex! Let’s make a bet, if you come while mommy rubs this all over your cock, then I’ll be your slave for a month. If you don’t, then you’ll be my slave. You agree and I cover your surprisingly big dick with the creamy white lotion. I use both my hands and my big full tits to try and get you off, but you can’t seem to come before the time runs out. Lucky for you, playing with my sons beautiful cock made Mommy REALLY horny. I lube it up properly and ride it to a wonderful orgasm before stroking it with my feet until you finally can’t take it anymore and cover Mommy’s face with your cum. Your next task as my slave is to get Mommy a towel…and then get hard again!
pov, handjobs, milf, footjobs, taboo
Download link ----> Handjob Bet With Mom - March 11, 2022 - 4.57 GB
I’m feeling lonely and bored, so I decide to see what you’re doing all alone in your room. You say that you’re watching a movie. When I snatch your laptop and discover that it’s porn, I’m shocked, but not appalled.
I did say I’d watch ANYTHING you wanted. Can we finish it together?
You sit next to me on the couch as I put the dirty movie on the big screen tv in the living room. You can hear my thoughts as I get more and more turned on watching this porno with you, thinking filthy things that a mother shouldn’t be thinking about her son, but I can see the outline of your huge erection in your pants and I want to see more! I convince you that it’s okay to take out your cock. Mommy wants you to stroke it while she plays with herself. I spread my legs and expose my big MILF tits while the moans of the woman getting fucked in the movie play in the background. After rubbing my hard clit to a screaming orgasm, I let you in on a little secret: Mommy really likes getting fucked after masturbating and that big, gorgeous cock of yours is quite a tease.
I take your beautiful cock in my mouth to get it as hard as possible for my pussy. Don’t come yet! Not even when I lovingly lick your long shaft. Not even when I deep throat as much of your enormous dick as I possibly can until my eyes cross. When you can’t take it anymore, I get naked and spread myself open for you. I play with my tits as you fuck me exactly how I like to be fucked. You ride me long and hard through multiple orgasms and, even though I tell you not to come in me, my inner thoughts are begging you to cream pie my hungry, wet pussy.
Did you like Mommy’s pussy, sweetie? Because if you keep this a secret, we can definitely do it again!
milf, masturbation encouragement, pov sex, taboo, mommy roleplay
Download link ----> Penny Barber - Watching Porn With Mommy - August 04, 2023 - 4.31 GB
I did not expect to find you out here in your old play fort, sweetheart. Don't you have any Valentine's Day plans? You have a crush on a mysterious older woman but you are not sure how to tell her? You can at least tell me who she is, you know I can keep a secret. So you will only tell me if I give you a special kiss somewhere below your tummy. A blowjob just to tell me who you want to be your Valentine seems like a pretty steep price but ok.
I stripped down to my pink bra and panties and sucked your cock but you still won't share your secret. You may have a nice cock but you are acting a little spoiled if you think I am going to let you fuck me just to find out the name of your crush. I am starting to think I have a pretty good idea who this older woman might be though. If my guess is correct then maybe you do deserve to put it in Mom's pussy this Valentine's Day.
milf, pov sex, taboo, mommy roleplay
Download link ----> Mom Fucks You in Your Fort - February 23, 2020 - 652.11 MB
You show up to my house late at night after a heated argument with your new wife, Alison. I’m surprised to see you, but manage to get the whole story out of you: She won’t fuck you without a condom! You’re so upset that I think you should spend the night—in my bed.
I quickly stash my vibrator and panties, slip off my robe, and let my hair down before inviting you in. We snuggle up as I wear nothing but a skimpy, silky nightgown that clings to my big, soft breasts. We try to rest, but I can’t stop thinking about how frustrated you must be and you’re finding me to be a little distracting, too.
You know, I thinks I have the perfect solution to your problem: you can fuck ME without a condom! I stroke your cock to attention under the covers, then take it out and give a long, leisurely blowjob, showing you the soles of my feet and jiggling my ass as I suck. Once it feels as hard as it can possibly get, I mount you cowgirl and proceed to ride you with passionate abandon. Two wet step-mom orgasms are all you can stand before you do what you so desperately want to: fill my tight, loving pussy with your warm semen.
I think you and Alison are going to be just fine. Step-Mom is ALWAYS happy to help if you need it again, sweetheart! XOX
pov, milf, taboo, creampie, family
Download link ----> Coming in Mommy's Pussy - August 19, 2022 - 3.1 GB
It’s been a while since MommyDom got good and properly fucked, not that I don’t enjoy your soft little mouth. But sometimes MommyDom just needs to get reamed, you know? You’re so eager to finally get what big boys get that you start tugging at your diaper, but not so fast! Your job is to just sit quietly and watch while MommyDom takes a real man. First I’m going to put a pretty, glass butt plug up your tush. You just make the cutest expressions when you have something in your butt! Then you need a pacifier to make sure that you’re nice and quiet and don’t start crying while I’m taking my bull’s fat dick. And I’m going to tie you up because…why not? This is happening, sweetie, so you might as well enjoy it! Was that the doorbell that I just heard? After I answer the door in my lingerie, I lead him back to the bedroom and show that big, hard stud how much I love a big, hard dick. I know you’re jealous, sweetie, but some dicks are just better than others: some need pussies and some need diapers. It isn’t all bad news, though. Since you were such a good little cuckybaby I’m going to let you lick a creamy treat out of my pussy!
Timestamps:
4:19 Diapering you
5:10 Bra out
7:58 Putting a butt plug in your cute little tush
10:44 Pacifier and bondage
16:58 Bull arrives
17:20 Stroking his big cock
17:53 Blowjob for my stud while you watch
22:11 Titty fucking
23:42 More blowjob
24:39 Playing with my tits
26:00 Even more blowjob! (MommyDom just loves to suck bull dick.)
28:26 Doggy style sex
32:28 MommyDom cums on her stud’s big cock
34:11 Missionary sex
37:19 MommyDom orgasms while being filled with bull jizz
38:18 Making you lick cum out of my pussy
cuckolding, diaper, diaper discipline, femdom pov, sissification
Download link ----> Mommy Diapers, Plugs, and Cucks You - February 04, 2021 - 4.53 GB
i get so many people asking me why i always bring this diaper bag to the gym. i’m not sure that they buy the story that i just like it. of course, you and i know about what’s really in her, i.e. not just my gym towel. gosh, i hope nobody peeks in here when i go to shower. i’m excited that you finally met your goal so that i can show you exactly what’s in here. is my little gym rat ready to be my little gym babie? you’ve worked so hard for this. just thinking about it is making me feel all tingly.
to start, you have to take off all of your clothes. are you embarrassed? that’s okay. i kind of like it when you blush—and when you get hard! it’s adorable that being naked in front of me gives you a stiffy. if you’re still so embarrassed about being naked i guess that i can take off my a shirt and show you my pink sports bra. now, let’s get down on the floor and get out your diaper changing pad, this bellissimo diaper, babie lotion, and this babie powder. i even have a babie bottle of water for you to rehydrate! i want this to be special, so i’m going to slip the nipple into my wet pussy before i give it to you.
i know that i’m not supposed to want to treat my big, strong boyfriend like a babie, but i can’t help myself. i pull down my leggings to expose my big, round ass, and start teasing my slit with the bottle nipple, coating it with pussy juice. then i turn around and use it to flick my perky little clit. i want you to taste my sex while you’re [***] from a bottle, to condition you to like it and get hard over diapers.
now that the babie boyfriend has his bottle, he needs his diaper, too. and i got you such a cute one! i slide the diaper under your well-toned ass and sprinkle you with babie powder. i rub it into your skin while babie talking to you, then tape you up, nice and secure so that you won’t leak when you pee. i’m enjoying myself so much that i strip out of my sports bra, too, telling you how much i’m going to love it when you wet your diaper for me.
to help you relax even more, i start giving you a massage with babie lotion. i get a little carried away and start rubbing it into my bare tits, too. i start rubbing my lotioned tits against your diaper, giving you a diaper tit job. i hope that i’m not making you too hard to wet. although…it actually feels a little warm down here. what is that? was i titty fucking a wet diaper?
i had better change you. you still want something to suck on, though, don’t you? i prepare you a pacifier to keep you happy while i change your diaper. i bury it deep in my pussy, getting it nice and wet. i ask you if you’re hard in your wet diaper to make my pussy juicier before i start rubbing the paci against my clit, too. do you like your pussy paci?
i strip out of my clothes entirely so that i can be naked while i change you. i make a little heart over my cleavage with babie lotion so that i can give you a breast job while i change you and your cock will just slide into my cleavage. i can smell how wet you are as i titty fuck you, my face inches from your wet diaper.
i can feel that you’re getting close to cumming, but before you do, i want to do something: i want to wet your diaper, too. i pull it forward a little, tease my clit out, and release all my golden pee onto your diaper and cock. it’s so warm! there. now you can cum on my tits, babie boyfriend. i know you want to get me back for wetting all over you, so i give you a countdown from 10 until you spurt your cum all over and make me just as dirty as i made you
diaper, diaper fetish, pee, pov sex, leggings
Download link ----> Diapered Titty Fuck After Workout - January 11, 2017 - 1.3 GB
Watch the full clip in my store! XO
big tits, older woman / younger man ., pov sex, taboo, mommy roleplay
Download link ----> FREE Mommy Knows You Fuck Your Sister - February 27, 2021 - 160.8 MB
I understand that you are a bit embarrassed to talk about why you made this appointment but, as your doctor, I will need to know if I am going to help you. Is it a sexual problem? Ok but it does have something to do with your genitals? Ah, I see. Well an overactive bladder would explain what you are describing. I know it can be very humiliating to wet yourself at your age but I am sure we can help you solve this little problem. Medications are available but I think what you really need is a prescription for diapers. Let me just call in the nurse and we can get you into one straight away.
The nurse is just here to observe and she will not be laughing at or teasing you, I promise. The nurse will be totally professional and I am sure she will take no pleasure in seeing an attractive young man stripped naked and taped into a diaper like a helpless baby. She will not think of seeing you getting diapered as different from any other medical procedure, even if you accidentally get a cute little erection while getting powdered.
cock tease, diaper discipline, imposed ejaculations, nurse play, adult babies
Download link ----> Diapered In Front Of Naughty Nurse - June 28, 2019 - 671.66 MB
I need to borrow some clothes after a little kitchen mishap ruins my dress but we seem to have very different ideas on what is appropriate for your own mom to wear in front of you. First, you refuse to turn around so I can have some privacy when I take off my dress (even after the embarrassing admission that I'm not wearing a bra) then all you give me to cover up with is a red babydoll that is completely transparent. I know you can see my nipples perfectly with this thing on.
When I ask for something different you just make me try on sluttier and more revealing items. For some reason the only clothes your ex-girlfriend left behind were her sexiest pieces of lingerie. I actually end up getting even more naked than I started out because some of the items are so skimpy I had to remove my stockings and panties to even get them on. It is almost like you want your mom's big tits, round ass and bare pussy to be on display for you.
milf, lace/lingerie, role play, embarrassed naked female, taboo
Download link ----> Making Mom Wear Sexy Lingerie - February 24, 2019 - 839.02 MB
I was so surprised to get a phone call from your teacher that was not a glowing compliment. What has gotten you off track this semester? Sweetheart, being horny is normal and not an excuse for poor academic performance. What do you mean are horny for something “weird”? You can tell me and I promise I will do whatever I can to help you get your grades back up.
Wait, you want me to wear what? Stick that thing where? Oh goodness. Well, if dressing up in this slutty anime costume and wiggling my ass in your face with this plug in my hole is the only way to get you back to straight A’s, then I guess that is what I have to do.
pov, milf, butt plug, school uniform, taboo
Download link ----> Mom's Slutty Dress Up Motivation - June 17, 2022 - 550.35 MB
A bad grade, a fumble that cost you the big game, and your girlfriend dumped you: can this week get any worse? But Mommy’s here for you, whether you need to stare at my tits, feel my warm mouth around your cock, or take it out on my slutty pussy. I first notice you getting hard as you stare at my cleavage in my satin robe and then it somehow escalates to my taking your virginity. I wouldn’t normally do this, but you have had a really rough week and Mommy pussy makes everything better—I promise. Just take your cock out and let Mommy show you exactly how to feel better.
milf, big tits, pov sex, taboo, mommy roleplay
Download link ----> Mommy Comforts Her Special Boy - March 19, 2021 - 4.53 GB
[spoiler=Exposing Mommy's Kinks | Penny Barber - December 17, 2021 / 3.63 GB]
You are the best step-son ever! You took Step-Mommy to her kinky street fair when no-one else would go. Did you have a good time? Do you think Step-Mommy looked sexy in her outfit? I got really… excited being there with you. I take off my robe and show you I’m wearing nothing but a special “STEP-MOMMY” collar I got at the fair. My big tits and wet pussy are sensually bound in soft bamboo silk rope. I show you what a masochistic slut Mommy is by putting clothes pins on my throbbing clit and perky nipples. Doing this in front of you makes me so horny that I beg you to be my master and let me suck your beautiful cock. Once I’ve used my mouth to get it as stiff as possible, you take your grateful slutty Mommy-slave from behind and fill me with your warm cum.
clothespins, pov sex, submissive sluts, taboo, collars / leashes
Download link ----> Exposing Mommy's Kinks | Penny Barber - December 17, 2021 - 3.63 GB
You’re home from college and ready to destress. Between earning your PhD in psychology and breaking off your engagement with your girlfriend, all you really want is to spend some time at home with Mommy.
But things have been rough for me, too, dearest. Your father hasn’t exactly been attentive and I’ve taken to sneaking some vin de table in the evenings just to have an escape. Speaking of which, would you like to have a glass while we play a little game?
As the evening progresses, our inhibitions erode until we’re having the most open, frank discussion about sex and relationships that we’ve ever had. It isn’t long before your cock is in my mouth, hard and beautiful, and I don’t just want you in my mouth either. You slide into my sex, feeling your own mother’s desire holding and squeezing you—and I only get tighter as I drizzle candle wax all over my large, soft breasts. With each drop of pain, my vagina tightens and moistens, urging you to come inside of me. Can you keep Mommy’s dark secret?
milf, pov sex, submissive sluts, taboo, mommy roleplay
Download link ----> Mommy's Dark Secret - February 18, 2021 - 4.47 GB
Follow me on twitter.com/pamperedpenny
Spoil me or just look at the weird stuff on my wishlist pamperpenny.com
XOXO,
Penny
feminization, sissy training, behind the scene, sissification, vlog
Download link ----> What I Like About Sissies - January 22, 2019 - 1.78 GB
I really like soft, shiny things. I suppose I have a material’s fetish. You finally manage to get me to take you back to my room where I’m wearing a smooth velvet dress and soft thigh high leggings. I tease you, running my hands over my shiny dress and telling you how soft it is and flashing my cleavage at you. Of course I have something nice and soft underneath my dress, too: my delicious, satin Victoria’s Secret bra and panties!
But there’s something else that I like to touch even more than my satin and velvet clothes. I’m a little embarrassed to tell you what it is. It’s so squishy, puffy, and soft, but… Can you guess what it is? No? Well, it’s a…diaper! But not just any diaper. It’s a really nice, high quality diaper specifically made for people with a diaper fetish. I kind of want to show it to you, even though it’s a little babyish.
Let’s work out a deal: you can touch my soft, velvet dress *wherever you want* and I get to show you my diaper. I continue running my hands all over my dress, showing you where you can touch me: my big breasts, my silky crotch. It’s like my whole body is made up of tactile pleasures: my soft dress, soft panties, and soft skin.
I get out my pink diaper bag and take out a thick Bellissimo Bambino diaper. I know it’s a little strange that a grown woman would like diapers so much, but I just can’t help myself. I play with it, making satisfying crinkling sounds and smelling it’s baby powder smell. I invite you to touch it with me, but you’re playing hardball and ask for something in return—for me to take off my dress and show you my bra and panties. I guess that sounds fair. It is a really cute bra-and-panty set after all. I don’t go shopping at Victoria’s Secret to not show off my lingerie!
I strip out of my dress and drop it on the floor before placing my diaper over my breasts and reminding you that you promised to touch it. I just want to feel you grope my big, soft tits through that thick, paddy diaper so badly. We feel the soft inside of the diaper, too. Can’t you imagine how delicious that would feel on your cock? The diaper feels amazing against my satin lingerie, but I bet it would feel even better against our bare skin.
You know, if we diapered each other, it would feel absolutely amazing. I know that it would make more sense for me to put you into your diaper first so that I could show you how to do it, but I can’t get over how hot it would be to put you in a diaper when I’m already wearing one.
I take off my lingerie, showing you how wet my panties got from playing with you and that diaper. Then I straddle my diaper, sprinkle myself with baby power, and tape up the sides. The baby powder really adds to the sensuality of the experience, making things even softer and filling my bedroom with that sweet, fetishy scent. I even let you watch me sprinkle it on my breasts and smooth it over my nipples. And I don’t forget my pussy and ass either. You watch eagerly as I massage it into my cute little butthole, gently teasing it.
Once I’m all taped up, wearing nothing but my diaper, it’s your turn. I have you take off all your clothes and lie down in front of me. The diaper really is super soft and inviting on your hard cock. It’s even better when I start powdering you and rubbing it into your erection. It feels so amazing that you’re not sure how long you can last. I make one last deal with you: I’ll watch you cum in your diaper and all over my soft breasts, but after you have to keep playing with me. I keep stroking you, making you promise to spend the day cuddling with me in our diapers—until you get hard again! I give you a countdown from 10, but you’re so excited that you shoot just before I get to 1. Baby talking to you, I tape you up in your cummy diaper to get ready for round 2
pov, diaper, diaper fetish, taboo
Download link ----> Penny's Super Soft Diaper Fetish - January 08, 2017 - 1.09 GB
I am sorry you had a fight with your girlfriend, I mean your fiance, but I am more than happy to have you spend the night, sweetheart. Why don’t you snuggle up and tell me what this big bad fight was about? Well, maybe it can wait till morning.
…
I cannot believe I just got woken up by my son beating off in my bed. No need to stop I already saw what you were doing. Oh I guess you want me to do it for you then. There is no point in arguing since we both know that Mom always knows best. It’s not like you have anywhere else to go even if I didn’t have a hold of your dick. I don’t think a young man with such a hard on for his Mom needs to worry about going back to his girlfriend anytime soon. This might be the most action you get for a while.
milf, big tits, embarrassment, taboo, mommy roleplay
Download link ----> Caught Beating Off In Mom's Bed - August 25, 2019 - 660.99 MB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
milf, female ejaculation, footjobs, humiliation, taboo
Download link ----> FREE Mom Sexually Humiliates You - May 26, 2023 - 195.49 MB
Have you been hiding from the rest of the group hoping I would come change you without anyone knowing that woke up in a wet diaper? I only brought all your baby supplies on this trip to embarrass you in front of my friends so that plan is definitely not going to work. If you are going to be so fussy about your diapers then maybe I will just take them away. I would love to see you keep your pants dry all day after the diaper training I have been putting you through.
You can either admit to the whole group how much you need and want to be diapered or you can pee all over yourself in front of the whole group. Either way, they will find out that you are just a little baby who can't control his tiny thingy.
cock tease, diaper discipline, diaper fetish, humiliation, taboo
Download link ----> Diaper Soaking Humiliation Camping Trip - August 14, 2020 - 577.25 MB
Watch the full clip in my store! XO
cuckolding, diaper discipline, diaper fetish, adult babies, psychiatrist
Download link ----> FREE Diaper Cuckold Therapy - June 04, 2021 - 184.9 MB
Get the full video in my store! XO
milf, squirt, cum swallowers, older woman / younger man ., pov blowjob
Download link ----> Cream for Mommy's Coffee Trailer - December 15, 2020 - 155.04 MB
I’ve noticed that you’ve been having a lot of nighttime accidents. Since I don’t like having to wash your sheets every single day, I got you some diapers. Now don’t be fussy! You can pick which ones you want: the thin, blue stripes or the thick, green stripes. Neither? Oh, you’re being so difficult! Fine. I’ll choose. I pick…the Disney princess ones! No, it’s no good trying to choose now. I’ve already decided. Now we’re going to get you diapered up in these cute, girly diapers and send you off to bed. Do you need Mommie to do the special thing so that you can relax? Okay, just let me take off my clothes
role play, diaper, diaper discipline, diaper fetish, taboo
Download link ----> Mommie Chooses Your Bedtime Diapers - May 12, 2017 - 1.0 GB
Watch the full video in my store. XO
pov, anal masturbation, anal play, mommy roleplay, pov blowjob
Download link ----> FREE Mom's Anal Diary - January 01, 2021 - 188.95 MB
You can’t go out with some girl tonight, you’re supposed to spend the evening with step-Mommy! Well, if you insist on seeing this…tart, then step-Mommy is going to insist that you keep it in your pants, or rather — in your diaper! Now, drop your pants and show step-Mommy what she’ll be padding this evening. Wow. That is small! You should be grateful that step-Mommy is doing you the favor of pampering your petite penis, because I’m sure this girl would lose interest if she saw it. She might even laugh, and of course you know you can’t count on some girl to keep a secret, not like step-Mommy will.
You know, it’s kind of appropriate that I have you in a diaper, because I just happen to be wearing a sexy, lacy, pink nursing bra. Do you know what diaper boys like to do? They like to suck on step-Mommy’s nipples, don’t they? Your mouth feels so good that step-Mommy has no choice but to masturbate while you nurse. Keep doing that until…step-Mommy…COMES! How much do you think you would have to do that before I start to make milk again?
You’re eager to make your date, but before I let you go, you are going to wet that diaper for step-Mommy. Stand and let me look up at you while I play with myself and encourage you to pee. Do it for step-Mommy, sweetie. I want to smell your squishy, embarrassingly wet diaper. Step-Mommy wants to smell your pee…good boy!
Now which one of us should answer the door when your little date arrives?
pov, diaper, diaper discipline, diaper fetish, taboo
Download link ----> Penny Barber - Still Mommy's Diaper Boy - March 10, 2023 - 4.43 GB
When I agreed to play your kinky diaper games, you promised you would change me as soon I needed it. You never said anything about making me humiliate myself to earn a dry diaper. Isn't admitting that I just wet myself embarrassing enough for you? I even called you the D word like a good girl.
I will try to pick the most humiliating diaper to wear from your collection but they are all pretty humiliating if you ask me. I will also put myself on display for you by rubbing baby oil over my tits and showing off my bare bottom while I powder myself. One thing I will never do though is admit that these embarrassing diaper games are making my pussy wet in more ways than one.
diaper fetish, humiliation, adult babies
Download link ----> You Make My Diaper Change Embarrassing - May 15, 2020 - 614.2 MB
My grandparents (you and my grandmother) are visiting for a while, which is just fine with me. You see me as being so innocent and pure and absolutely adore me. Then, when I go to do some laundry, I find that someone has masturbated into my underwear. As it dawns on me that this is my grandfather’s sperm in my panties, I hatch a plan.
That night, I get you alone after everyone has gone to bed. I start teasing you, calling you a dirty old man and telling you that I know something about you, something that you should have tried harder to keep hidden. Then I pull out that familiar little, white, satin thong. I inhale the scent of your cum and even taste it. Perhaps I’m not as innocent as you thought, Granddaddy!
That’s when I start to play hardball. You see, you’re going to play a game with me, a game which I will win. You’re going to spoil me rotten—a new roadster, money whenever I want it, my rent paid for, a credit card on your account—and I’m going to spoil you in return. Just imagine it: my tight, young pussy eagerly taking your mature cock, a fresh pair of my panties everyday, and the joy of being my personal sex toy.
It’s almost too much for you to take it. Then I start stripping out of my “good girl” clothes to reveal matching satin bra and panties, telling you how to touch your hard cock for me. You’ve longed to see me out of my conservative clothes, my big breasts that can’t be concealed by my prim little sweaters completely bare. It’s like one of your perverted dreams cum true! Just do what I tell you, grandpa, and you’ll never have to wake up
financial domination, blackmail fantasy, daddys girl, money fetish, taboo
Download link ----> Grandad's Sexy Sole Inheritor - August 13, 2017 - 1.73 GB
You’re really nervous about talking to me, but your girlfriend has been pressuring you to propose—with my ring, apparently. You know that you’re my special boy and I want to do have everything that you want, but there’s still a price! I want…cock. No, not one of your buddies’. Mommy wants YOUR COCK.
I strip out of my dress and get on my knees to suck your cock, oiling up my tits as I relish the taste of you. Soon you’re tasting me, too, my legs spread wide as I perch on the counter, pulling you to me, your warm tongue circling my hard clit. Mommy just needs this so bad! But what I need most of all is your manhood in my pussy and your hot cum splattered all over my naked body! Only then will I give you what you came here for.
Timestamps:
4:44 Mommy strips
6:51 Blowjob-handjob with oiled up tits
14:57 Mommy masturbates and begs for oral sex
16:29 POV pussy eating
19:08 Fucking Mommy
26:03 Cumming on Mommy’s tits and face
milf, blackmail fantasy, pov sex, taboo, mommy roleplay
Download link ----> Earning Mommy's Engagement Ring - February 07, 2021 - 3.89 GB
Natalie and I are hanging out in our school girl outfits but all I really want to do is trade in our cute panties for even cuter diapers. I got to diaper Natalie first but I get too distracted by her sweet ass and adorable girlcock so I just end up licking her for a while instead of taping her up. Lucky for me, Natalie is such a sweetheart that she returns the favor by licking me to an orgasm before diapering me, even though my pussy is already covered in baby powder.
Even after we are both fully diapered, we just want to stick our face in each other's padded butts and never come up for air.
diaper, diaper fetish, face sitting, oral sex, trans
Download link ----> Diaper Sex With Natalie Mars - August 17, 2019 - 898.59 MB
We asked you to show up a little early because I need to get you ready to entertain everyone. You did not think my son and all his jock friends wanted you to actually party with them? No, sweetie, you are just here as a little femboy party favor. I am going to get you all pretty and sissified so those boys have a blowjob doll for the night.
I will do your make-up while you pick out some cute lingerie to wear. Then we need to get that cute little ass filled by this pretty pink plug. Go ahead and give it a little lick so I can slide it in easier for you. The butt plug might be a tight fit but some of the boys coming over are much bigger so you will be glad to have your hole warmed up beforehand, trust me.
milf, feminization, imposed bi, taboo
Download link ----> Making You My Son's Sissy - December 24, 2019 - 759.5 MB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
milf, diaper, diaper discipline, diaper fetish, femdom pov
Download link ----> FREE Diaper Sex at Work - September 09, 2022 - 88.91 MB
I know you would do anything for me, especially when I'm in this lacy, pink bodysuit. You would happily suck your thumb for me and wear a diaper like a little baby just to get me to pay attention to your thingy. What if I want you to be my little baby girl though? A soft little sissy with plastic rhumba panties over her diaper and under her pink frilly dress is exactly what I want. The only way I will be your Mommy is if you are my sweet sissy baby but you can't be a good girl with your thingy all stiff and hard in your diaper. Luckily I have just the thing to keep you tiny and soft in your diaper and it even matches the rest of your outfit!
chastity devices, big tits, cock tease, diaper fetish, feminization
Download link ----> Sissy Baby For A Day - December 28, 2018 - 839.05 MB
Buy the full video in my store! XO
mistress, diaper, diaper discipline, female domination, femdom pov
Download link ----> Diaper Simp Extended Trailer - November 04, 2020 - 141.19 MB
It must be hard being unemployed and alone all day, sweetie. You’d think with all that free time that you might devote some of it to pleasing me when I’m home… but no. I have to do everything myself. So today, I’m going to use you for MY pleasure. To start, I’m putting you in a diaper whether you like it or not! I spit in it and pee in it before closing it up and rubbing my wet pussy against it. Then I put a strap-on over your diaper and tell you how much more satisfying it is than your pathetic little dick. I ride it hard and recount every time I’ve cheated on you as I build to a delicious orgasm. The doorbell rings just as I finish. I have company, darling, and you are going to let him in while I get ready to fuck his brains out! Oh, and keep the diaper on. XOX
pov, diaper, diaper discipline, diaper fetish, humiliation
Download link ----> Diapered and Cucked - September 17, 2021 - 3.59 GB
Seeing me trapped in a boring conversation across the room, you catch my attention and let me know that you are the type of guy that’s up for a little adventure. You follow me to the coat room where I pull not one, but two diapers. With these on we can party all night and never worry about the crazy bathroom lines. You get excited helping put mine on and—for further encouragement—I take your big hard dick out of your pants and blow you into a very agreeable state. Once we’re both pampered, we head back to the party to see which one of us will wet their diaper the most while hoping no-one else notices!
I keep you close and flash you my diaper and big soft tits whenever I get a chance. When I’m finally ready to pee, I call you over and give you a nice close look. Worried we’ll get caught, you escort me back to the coat room where we rub our wet diapers together, making me come. Desperately horny, I pry your stiff cock out of your wet diaper and pull mine aside enough for you to fuck me while we keep them on. You make me come again before finally giving me a nice wet creampie deep in my tight diapered pussy.
I knew you’d be the most interesting guy here. XOXO
pov, diaper, diaper fetish, pee, party game
Download link ----> Diaper Hook Up - June 03, 2022 - 4.56 GB
The full clip is available in my store! XO
big tits, bondage, older woman / younger man ., funny moments, mommy roleplay
Download link ----> FREE Mommy Gets Stuck and Fucked - January 29, 2021 - 147.61 MB
Honey, you can’t skip another day of work. I know my promotion is lucrative, but that’s not the point. You’re “sick,” huh? Okay, then take this and go lie down. Good boy. I want my widdle hubby to get better, so I’m going to tie you to the bed. You should be feeling pretty weak and horny right about now. Don’t worry about getting up to go pee — this diaper ought to cover that. If you don’t like it then why is your thingy so stiff? Now lets immortalize this with a picture and…oh! Hang on, sweetie, I have to take this. You sit there in diapered silence while I tell my boss that since you’re out of commission, I’ll be free after work tonight to tend to his every need. This was probably the best way for you to find out about us.
I swing back home after work to check on you and get changed for my date tonight. Your diaper is soaking with pee, but I won’t change you until after I’ve gotten ready. You watch me strip out of my work clothes before slipping into a slinky cocktail dress. Despite the humiliation, your cock is harder than it’s ever been. I tell you how things are going to be from now on and stoke your raging erection as I change you. Finally you can’t take it anymore and you blow your load all over my hand. You’re going to do whatever I want from now on, darling. XOXO
cuckolding, diaper, diaper discipline, diaper fetish, humiliation
Download link ----> Lazy Lying Husband Diapered & Cucked - March 18, 2022 - 4.07 GB
I love making women of all ages submit to my strap-on. From my step-daughters and all her slutty little friends to their stuck-up, MILFy teachers. I expect them to offer up all their holes for my pleasure but my favorite is definitely bending them over and fucking their asses. Nothing makes me feel more dominant than having some sweet fuck doll totally helpless because my big cock is filling up their tight little asshole.
milf, lesbian domination, pov strapon, taboo, mommy roleplay
Download link ----> Step-Mom Loves Fucking Girls in the Ass - May 24, 2020 - 460.71 MB
It is almost your turn to go on stage for the Sissy Baby Pageant but there is still time for a few wardrobe adjustments and some last second reminders not to suck your thumb when talking to the judges. The skirt and petticoats of your outfit were designed to show off that big puffy diaper so it has to look perfect. That means absolutely no little bulge from a sissy stiffy like the one you were hoping I would not notice. It may be tiny but you better believe the judges will take points off for such naughtiness. I knew I should have locked your little cocklette up but it is way too late for that now. Luckily, I brought the quiet vibrator so hopefully none of the other sissy babies or mommies can hear me get rid of that little stiffy in your diaper.
diaper, feminization, imposed ejaculations, taboo
Download link ----> Nervous Stiffy Before Sissy Baby Pageant - April 12, 2019 - 647.04 MB
After a night of dancing at the club, I wander into the kitchen for a snack. Nobody would take me home with them. Maybe because I forgot to put on deodorant? Asking you for a sniff check turns into some pretty nasty, smelly sex. You inhale my scent and can’t control the throbbing erection in your pants. Is it…is it weird if Mommy want to smell your cock?
We get the couch nice and dirty, sniffing each other all over. I ask you to smell my armpits, my feet, and my panties, giving you a worshipful, eager blowjob, sucking your pungent cock and cumming over and over again. Is it our fault if we come from a horny, sweaty, fragrant family?
milf, foot smelling, pov sex, smell fetish, taboo
Download link ----> Scent of a Mommy - July 09, 2022 - 4.56 GB
I’ve been in the neighborhood for a while now, but this is the first time you’ve ever actually come over. I see you all the time, so it’s nice to finally connect! Plus I’m home on my own most of the day. I guess I’m a housewife, but I’m not really into cooking or cleaning. I don’t shop much. Honestly I’m a little bored, so having you over is super exciting for me! Except—do you hear that noise? That sort of…crinkle? Oh my god. Are you wearing a diaper?! That’s so…hot! It looks a little wet, though. Do you think that I could change you? Is that weird? What if it makes me super horny and I just want to play with my pussy, then jerk you off into your wet diaper? Because that’s exactly what I’m doing!
Penny Barber is your hot neighbor. Sort of a bored housewife, she’s thrilled to have someone to talk to. When she hears the crinkle of your wet diaper, all propriety goes out the window and she can’t help but give you a sexual diaper change. She also talks about sissifying you, taking you shopping on her workaholic husband’s credit card. Hopefully you’re ready to be a diapered sex toy. Even though Penny’s shy, she’s so sexy in her tight little dress—and out of it!—that you can’t really say no to any of her dirty, kinky suggestions.
diaper, diaper fetish, lotion/oil fetish, cheating wife, mommy roleplay
Download link ----> Sexy Neighbor Diapers You - July 03, 2021 - 4.48 GB
Your mom hired me to babysit you, even though we’re basically the same age. And then she left this stupid boardgame for us to play. I don’t know about you, but I’d rather play something more fun. It feels really, really good. But if you want to play, you’re going to have to take all of your clothes off! Are you embarrassed to be naked in front of your hot babysitter? How cute! No wonder your mom thought that you still needed a sitter. You’re a virgin! Don’t try to deny it: I can tell. Now take off your clothes, virgin, so that you can wear this cute little onesie that I have in my babysitter bag.
Don’t pretend that you don’t want to. I can see your hard on, you know. No need to be embarrassed and cover it up. That’s part of the game. And I’m sure that you just love me looking at your erection. So, just slip into this cute little onesie… Hmm. Something’s wrong. It’s kinda baggy around your crotch. But it wouldn’t be so baggy if you were wearing a DIAPER, now would it?
Telling you that this is all just part of the game, I get you to lie down on the big, puffy ABU diaper. You’re so humiliated that your sexy babysitter is doing this to you, but you can’t help but being turned on as I tease you about how you jerk off and sprinkle baby powder all over your pretty virgin cock, giving you a good look down my skimpy shirt at my big, slutty tits. I can tell that you’re looking, but instead of getting upset, I take my top off! It’s just so much fun messing with you. I’d better be careful, though. I don’t want to to cum all over the place—not before you wet your diaper.
Because that’s the game: you have to wet your diaper in order to masturbate. And I’ll know that you’re wet because you’ll spit out your pacifier. Of course I’m going to make it as difficult as possible for you to wet. I’m going to tease you until you’re so hard that you can’t pee, even though you’re desperate to jerk off! Standing over you, I show you my cute, white panties and continue to verbally tease you. Isn’t that frustrating? Do you wish that we were still playing boardgames? Is looking at my panties too much for the little diaper babie to handle? Are you gonna ask your mom not to leave you with that mean girl, Penny?
I strip down to my panties and am just about to take those off, too, when I notice that you spit out your pacifier! I slide my fingers into your diaper and, sure enough, you’re all wet! I get down on the floor with you and give you a handful of babie oil, then start wiggling around, posing and encouraging you to masturbate in your diaper. Babie talking, I make you promise not to tell your mom about our special, secret game. You’re so on edge that I give you a countdown just from 5. I barely whisper the word, “One,” when you cum all over yourself
joi, diaper, diaper discipline, diaper fetish, joi games
Download link ----> Babysitter Penny's Secret Diaper Game - February 04, 2017 - 1.74 GB
Your prom date shows up before you're ready to go, so I sit her down in the family room to chat. Naturally the subject turns to just how often I catch you playing with yourself. I go on and on, telling her how no room in the house is safe, how your hamper is basically a DNA storehouse, how you'll even sneak off in public to go yank it when the urge hits! Then, for some reason, she says that she just remembered that she, uh, can't go out tonight. Oops. Sorry about that, honey. At least you have your trusty gym sock!
milf, humiliation, masturbation humiliation, taboo
Download link ----> Mom Tells Your Date How Much You Jerk It - February 02, 2019 - 1.79 GB
Ella and I had a little mix up with our underwear laundry so the obvious solution is to call in her little brother, Sam, to separate the clean and dirty panties by making him sniff every single pair. He gets all shy and cute when we shove our undies in his face and ask if he can smell pussy or not. Ella and I have so much fun teasing him that we decide the most accurate sniff test would be if we stripped down and tried on each pair so he can smell the panties while we are wearing them. Poor boy probably thought it couldn’t get any more embarrassing than his mom shoving his face into his sisters pantied ass but then I take all the clothes he is wearing to throw in the dirty laundry too.
We both burst out laughing as he tries to cover his throbbing little hard-on when it pops into view but we just knock his hands away so we can play with his cock a bit ourselves. I know it can be quite humiliating for a young man to be naked and erect in front of his mom and sister so I “let” Sammy put on a pair of Ella’s dirty panties before we continue the fun. By the time we finish up Sammy has become very familiar with the smell of his sister’s pussy and the sight of her butt from very close up. All the undies still have to go back in wash though because poor little Sammy ends up getting every single pair of panties quite sticky before we are done with him.
ass, handjobs, imposed fem, panty fetish, taboo
Download link ----> Panty Sniff Test For Ella Nova's Brother - March 10, 2019 - 876.2 MB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
latex, diaper discipline, diaper fetish, sissy training, mommy roleplay
Download link ----> FREE Chemical Regression - August 18, 2023 - 187.04 MB
Watch the full clip in my store! XOX Follow me on Twitter.com/PamperedPenny
cream pie, pov sex, taboo, mommy roleplay, funny
Download link ----> FREE Eat Your Vaggies - November 04, 2022 - 83.53 MB
I know the mini-bar is expensive but I say we kick this Mom and Son trip up a notch. Don't make me partake alone. Your father is so boring and these little getaways are my chance to have a little fun. Boring on vacation and boring in bed. Oops, did I say that aloud?
It is true though, we don't ever experiment or even try sex toys. I think I look pretty good, tits still perky and my ass is still tight. It would be so nice to get some real sexual attention again. Like a handsome young man watching me get off and actually appreciating my body for instance. I do have my favorite vibrator with me if any strapping studs would be interested in seeing what their Mom looks like when she cums.
milf, taboo, vibrator, mommy roleplay
Download link ----> Mini-Bar Makes Mom Too Horny - March 01, 2020 - 660.82 MB
Follow me on Twitter @pamperedpenny
Follow me on Instagram @pampered_penny
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_____________________
Order a custom video, starting at $150
https://www.manyvids.com/Custom-vid/147843
milf, lace/lingerie, bra & panties, panty fetish, behind the scene
Download link ----> Favorite Lingerie - October 01, 2017 - 1.74 GB
Just a good, old-fashioned wank-along with Mom Penny Barber! I strip out of my silk Victoria's Secret robe to reveal my gorgeous curves. Do you want to masturbate with me, honey? Take your cock out and start stroking. Mommy will play with herself, too! I spread my legs and let you see absolutely everything as I massage my dripping pussy and diamond-hard clit. Don't go too fast and do your best to cum when I do.
XOXO
milf, duel masturbation, taboo
Download link ----> Masturbating with Mom - April 22, 2018 - 1.77 GB
I’ve been cheating on your pathetic father for years and now I’ve finally divorced him. While you sit there, squirming and uncomfortable, I tell you every sordid detail. You can visualize every dirty little affair—the hot neighbor boy, your dad’s boss at a dinner party, the UPS delivery guy. You’re so embarrassed, but also so…turned on. Which brings me to my point, darling: you’re just as big a loser as your father with one, huge exception: your fat cock. Now you’re going to be Mommy’s sex toy, performing every perverted sex act that pops into my mind. So come over here, and put your fat cock in Mommy’s tight pussy. Actually, I think I still have another man’s cum inside of me. You don’t mind, do you, sweetie?
Four POV blowjob and sex vignettes while I wear pantyhose.
Scene 1 0:03 Outdoor blowjob and facial with neighbor boy.
Scene 2 6:51 Fucking your dad’s boss in the kitchen during a dinner party before he cums in my glass.
Scene 3 19:31 Fucking the delivery guy, then masturbating with his cum inside of me.
Scene 4 28:46 Sex with my son with another man’s cum inside of me.
Mommy Dom - pantyhose - feet - foot fetish - stockings - femdom - milf
milf, pov sex, taboo, cheating wife, cheating
Download link ----> Cheating Mommy Takes Control - July 01, 2021 - 4.52 GB
Mommie wants to put on a slutty little show for you today. If you are good I will teach you how to worship my heels... and maybe even my ass if you are very lucky.
ass, high heels, fetish
Download link ----> Mommie's Blue Heels - March 20, 2016 - 822.06 MB
I caught you looking up my skirt so don't even try to argue with me. Your stiffy is quite obvious. I can totally see that thick bulge straining against your jeans. Actually, come here for a second, I just want to...
I know it is so perverted that I just unzipped you and put it in my mouth but I couldn't help myself. I am only going to play with your cock and suck on it a little. Maybe a lot. Ok um, on second thought, let's move this to the bed. I should not let you fuck me but I just need that dick. No cumming in Step-Mom's pussy, though, and this time I really mean it!
milf, upskirt, blow jobs, pov sex, taboo
Download link ----> Upskirt Peeks Lead to Sex with Mom - July 05, 2020 - 623.76 MB
I caught naughty little Bambi trying to seduce you into giving her a very explicit sexual education. As soon as I realized what you and your sister were up to, I put the bare bottom she had just been wiggling in your face over my knee for a quick spanking. If Bambi wants to show off her adorably tiny tits and puffy pussy while she learns about the birds and bees, then she will do it under Mom's supervision.
I make her spread her legs to give her brother an anatomy lesson while I explain that she since thinks it is appropriate for her brother to see her in a thong then she will be allowed to wear nothing but panties in the house from now on. Bambi is not the only one who has to get naked though and it is only fair that she gets to take her time staring at your cock just like you did to her entire naked body. I even make Bambi describe your erection, since we are here to learn after all but she doesn't get much past "big" and "hard". Of course, this lesson will not be complete until you climb on the bed with that big, hard cock and fuck your sister with it.
milf, pov sex, sisters, spanking f/f, taboo
Download link ----> Mom Makes You Fuck Little Sis Bambi - April 07, 2019 - 664.13 MB
You have fun going out, sweetie. Mommy will just run errands and then find some way to relax by herself. You’re gone when I return from the grocery store and realize that I subconsciously purchased VERY phallic produce. Alone and desperately horny, I proceed to fellate and fuck the bounty of “cocks” I’ve brought home — until you show up and catch me completely naked with a carrot in my ass on the kitchen counter! I’m so embarrassed, honey. What will it take for you to keep this a secret? Oh… you want to help Mommy “relax.” I take your big beautiful dick out and play with it using my hands, my mouth, and my big tits. You bend me over the kitchen sink and give my pussy the pounding it’s been aching for. After a powerful orgasm, I get down and let you cum in my grateful little mouth.
Thank you for giving Mommy what she really needed, stud.
milf, food masturbation, pov sex, taboo, caught
Download link ----> Putting the Groceries Away HARD - November 26, 2021 - 4.58 GB
Watch the full clip in my store! XO
cuckolding, diaper, diaper discipline, diaper fetish, sissy training
Download link ----> FREE Mommy Diapers, Plugs, and Cucks You - February 04, 2021 - 187.01 MB
When I catch you spying on me as I get ready for my date, I decide to have a little fun with you. I start off just teasing you a little, asking if you like what I'm wearing, but when I notice that you're playing with yourself as you stare, things really get going! You want to jerk off while you look at me? Fine, then I'm going to look at you, too, and it's not good resisting!
ass worship, big butts, sisters, taboo, butts
Download link ----> Stroking to Your Sister's Ass - November 15, 2018 - 1.83 GB
It’s your last sleepover before you go away to college and you and your best friend have some big plans for the evening, but Mommy knows how you get when you don’t make time to stroke that massive cock of yours. I’ve never met a boy with such an overactive libido. You must get it from me. You think you’ll be fine, but I just know you’re going to wake up with the biggest, hardest erection ever.
I pull up my black, satin nightgown and slip into your napping bag with you, my warm pussy ready to take care of that morning wood for you, even though you didn’t listen to me. I’ll try not to moan and squirt all over your napping bag, but no promises! What’s more embarrassing: your friend seeing your stiffy or finding out that you fuck your mother?
pov, masturbation, squirting, taboo, mommy roleplay
Download link ----> Mom Fucks You at Your Sleepover - July 30, 2022 - 4.59 GB
Watch the full clip in my store! XOX Follow me on Twitter.com/pamperedpenny
diaper, diaper fetish, orgasms, pee, pov sex
Download link ----> FREE Diaper Sex - August 04, 2021 - 146.92 MB
You got hard in church again!? Go to your room while I pray on how to deal with your…libidinous urges.
I may be at my wits end, but I know if I just beg on my knees for long enough, the Lord will reveal himself to me. That’s it! The solution is almost too simple: I am going to take care of your erections every day before church. I mean, I can’t have you *ahem* masturbating like a heathen. As your loving Mother, I’m willing to do whatever it takes to get the devil out of you, even if it means clasping my hands around your cock instead of in prayer.
I stroke you like only a good, Christian woman can while showing you my gorgeous, MILF titties to help get you off, but, despite your huge load, you still manage to get hard in church! The devil sure is strong in you, but I’m not going to give up. I spread my legs and encourage you to fuck and fuck and fuck and fuck me until I’m positive that every last drop of your demon semen is in my saintly pussy.
milf, pov sex, taboo, mommy roleplay, prayer
Download link ----> Penny Barber - Sunday Morning Wood - January 27, 2023 - 4.24 GB
I said you could have a soda after your baseball game IF you won. You are going to have to do something else if you want to earn your this cold, refreshing treat. Why don't you unzip your pants and get your dick nice and hard for me. I will even take my tits out for inspiration. Now I want you to finish yourself off right here in the parking lot. Do you think you can make that cute cock of yours shoot before Step-Mom finishes your soda or somebody catches you stroking it in the car? Don't worry, you won't be the only one getting a little naked in here. I am going to give you plenty of peeks at my bare breasts, round ass, and wet pussy to help you cum before you get caught playing with yourself.
milf, joi, big tits, taboo, mommy roleplay
Download link ----> Step-Mom Makes You Jerk Off in the Car - September 13, 2020 - 355.55 MB
Watch the full clip in my store! XOX Follow me on Twitter.com/PamperedPenny
pov, diaper, diaper discipline, diaper fetish, humiliation
Download link ----> FREE Diapered and Cucked - September 16, 2021 - 200.59 MB
I've been texting you for hours without a reply, and at this point I have to assume that you’re just not coming over. Whatever. Your step-mom knows how to entertain herself! Unfortunately you finally come home right as that entertainment is coming to a climax—all over the kitchen counter! I’m coming and squirting like a complete slut just as you walk in the door and I can’t seem to stop. I’m sorry you had to see me coming, sweetie!
Ashamed, I put on a robe and sit with you to apologize. I have a … sex addiction. (It IS a real thing!) It seems to be triggered by boredom, which is why I wanted you to come over and keep me entertained. When I get bored I just can’t stop from touching myself, playing with my pussy until I come and come and come! But I’ll be better now that you’re here.
We settle down to play a boardgame, but I have a lot of trouble focusing and it isn’t long before you’re winning.
How about some new rules to help me out? I’ll just start doing things, and you let me know when you think I’ve earned some of that sweet Monopoly money. I strip out of my dress and play with my big tits. You get so hard watching that I just have to suck your fat cock. Remember: step-mom doesn’t have any control over her sex addiction, even with her own step-son!
You fork over Monopoly money as I ride you to orgasm after orgasm both cowgirl and doggy style, my fat MILF ass jiggling up and down. As a final treat, you glaze my face and tits with your hot semen. See? This game doesn’t have to be boring!
masturbation, milf, pov sex, squirting, taboo
Download link ----> Penny Barber - Mom's Sex Addiction - February 24, 2023 - 4.35 GB
You know the rules for my Book Club night is no hubbies allowed. I can't have you pretending to be a big boy when you will just end up distracting everyone by wetting yourself. I am keeping you in the bedroom in a diaper like last time but I think you need to be double diapered for extra protection this time.
I don't want you getting so soaked that you leak again and double diapers is just the best way. If you really need a change you can come ask me for a dry diaper in front of all my guests. I would rather you deal with a little embarrassment than leak on the furniture because you wet your diaper too many times. Now, if you will stop being fussy I might let you make sticky if you can do it before my friends show up.
cock tease, diaper, diaper discipline, humiliation, taboo
Download link ----> Double Diapered For Girl's Night - July 03, 2020 - 635.21 MB
I’m sick of doing laundry every single night, but I can’t just let you stay in those cummy sheets, can I? I was at a loss of what to do until I started to think outside the box: a thick, embarrassing Bambino Teddy diaper will deal with the mess and a layer of duct tape over your mouth will suppress any slutty moaning coming from your room! It would be nice if you could control your own libido, but until you can manage on your own, Mommy’s going to take things—your thing, to be specific—in hand. Not that I’m so cruel: I have a special surprise or you and I’ll tell you all about it while I pleasure your diapered cock with my very own vibrator and run my satin gloved hands over my fat Mommy tits. I just hope that I notice when you cum with your mouth all taped shut!
diaper, diaper discipline, diaper fetish, tape bondage, mommy roleplay
Download link ----> Mommy Diapers Your Overactive Cock - October 11, 2020 - 1.77 GB
I really think it is time we had a discussion about your attitude and your manners, young man. Would it really be so difficult to treat me with respect and maybe even say Please and Thank You sometimes? I would be so much more willing to help you out if you just asked nicely.
Will I please show you my tits? Very funny, mister. If that's how you want to play it then fine by me. Please take off my panties? How far are you willing to take this? I did promise I would be willing to help you more if you said please but I did not expect you to use the magic word to make me into a sex toy.
handjobs, milf, big tits, taboo, mommy roleplay
Download link ----> Magic Word Gets You Step-Mom's Tits - April 12, 2020 - 753.41 MB
Well look who finally decided to show up! You’ve had me worried sick all night and you come home smelling like beer and… some slut! People are starting to spreading rumors about you - some of which are hard to believe. Oh, I can’t stay mad at you, darling. I just don’t like being home alone in the evenings and I get so anxious the longer you’re out. Is there any way you could make Step-Mommy feel better? Let’s start with a kiss. That was nice. It looks like you really enjoy being this close to Step-Mommy. My goodness! Apparently the rumors are true, you are HUGE! Please let Step-Mommy play with that big dick of yours. I’ll rub it all over my big tits and then take as much of it as I can in my mouth and pussy. I really want to see how much cum you can make, sweetie. Show Step-Mommy you don’t need a curfew anymore.
milf, pov sex, taboo, huge dildo, cum on tits
Download link ----> Cum home to Mommy - May 06, 2022 - 3.33 GB
Watch the full video in my store!
milf, big tits, wax play, mommy roleplay, pov blowjob
Download link ----> FREE Mommy's Dark Secret - February 19, 2021 - 179.28 MB
Watch the full clip in my store. XO
milf, older woman / younger man ., taboo, mommy roleplay
Download link ----> FREE Mommy's Getting Divorced - May 24, 2021 - 170.66 MB
Ever since we met—me looking for my birth son, you looking for your birth mother—we knew that we might actually be related, but that didn't stop us from fucking! Now that I have the actual DNA test results on my kitchen counter, it's a little different. Things might change forever. Do you think that maybe, before we do find out for sure if I'm your mom, we could fuck one more time?
pov, milf, pov sex, taboo, mommy roleplay
Download link ----> Are You My Mommy - October 21, 2020 - 1.78 GB
We need to talk, Sweetie. Lately you’ve been spending a lot of time either playing video games or tinkering in the garage and I’m starting to worry about—you made me a present? Oh, look at this beautiful…is it a necklace? I love it, it says “step-mommy” on it and everything. Let me put it on right now and… … …suddenly the world turns pink and fuzzy. A bolt of pleasure shoots through my body. You know what, sexy? I don’t think you’ve been playing enough video games. Let me go change and set up the living room for you. It’s the least I can do after you made me, like, the BEST present ever!
I bring out your snacks wearing nothing but a pink frilly apron. Well, I didn’t want to get dirty, but if you don’t like it than I do have some other outfits to try on. You watch me strip and try on similarly slutty and servile sets before I tell you to clothes your eyes for the finale: lacy, white, crotchless panties with a lacy, white, cupless top. I can’t help but play with myself while telling you how sorry I am for interrupting you earlier. Step-Mom is gonna to make it up to you EVERY way she knows how!
Your cock practically springs out of your jeans as I start showering it with affection and adoration. It really is a perfect dick. All I can think about right now is how to keep it as hard as possible. It’s like, the more I pleasure you, the better I feel. My eyes cross again and again as I suck you, stroke you, and take your engorges phallus between my big, soft, pillowy titties. You fill my mouth with your cum and I play with your huge load before reminding you this is not where cum goes. You quickly get hard again and fuck me to several mind melting orgasms before filling my pussy with a nice wet creampie.
Do you have any more collars, sweetie? I think our sexy neighbor would really appreciate one. XOXO
mesmerize, pov sex, taboo, collars / leashes, mommy roleplay
Download link ----> Melting Mommy's Mind - August 12, 2022 - 4.14 GB
You finally get to go on a date with me and things are…not going well. I show up in a gorgeous, slutty cocktail dress, but instead of taking me to a nice restaurant, we go to some burger joint. You can tell that I’m trying, but I’m just not impressed. I’m about to send you home when you get so nervous that you wet yourself!
It’s just the cherry on top of a disastrous date. I freak out, but I’m also pretty sure that an Uber isn’t going to want to take you home in pee-soaked jeans. That’s when I get an idea. I just happen to have something lying around the house that might help you: A DIAPER.
I gently tease you about needing one, but I’m also not too surprised. You argue with me that you don’t need one when you wet yourself again! That’s when I decide that I’m just going to put you in a diaper whether you like it or not. Hmm. I wonder if I could make you wet yourself again and it certainly seems to work! Then I get a truly evil idea and you’re too humiliated to do anything other than go along with it
diaper, diaper discipline, diaper fetish, humiliation, jeans/pants wetting
Download link ----> Diapered for Wetting in Front of Date - June 15, 2018 - 1.82 GB
Lately I’ve been hearing a wet, telltale, fapping sound outside the bathroom door whenever I take a shower. I know you’ve been spying on me for a while now—your own step-mom! I’m finally going to do something about it. Let’s see how you like it!
I make you take your cock out and am blown away by how big and beautiful it is, but just because I’m enjoying myself doesn’t mean that this isn’t still a punishment, Mister! While you like the attention, you’re still chagrined when I roughly squeeze and spank your embarrassingly hard dick. I make you to lie on the floor, your fear boner pointing straight at the ceiling, and slowly, tantalizingly step on your cock with my sexy, red stiletto heels and kick you in your swollen balls. It hurts, but nothing seems to make that hard on subside! OMG, is my stepson a pervert?!
Maybe you need a taste of your own medicine. You’re going to sit there and watch while I masturbate to you for a change. With my vibrator pressed against my eager, little clit, you watch me come, my fat, luscious tits exposed to your hungry gaze. You wish that you could stroke to this show, but I order you to keep your hands off of your own aching erection. Does that feel more like a punishment, you dirty boy?
But I'm not a monster. You’ve been so thoroughly punished that I decide you can come. We drive out to a secluded parking spot. I know how much you love my breasts, so I pull my dress down as I reach between your legs and start to stroke your aching cock. You’ve been teased so much that only a few minutes into the handjob, you cover my face and tits with your hot, voluminous cum. Cleaning myself up with your clothes, I tell you to get out. That’s right: your wicked step-Mommy is leaving you out here NAKED! I’m sure someone will give you a ride home eventually, but you may have to earn it.
milf, footjobs, humiliation, pov sex, taboo
Download link ----> Mom Sexually Humiliates You - May 26, 2023 - 3.31 GB
What's Mommy to do when she's ready to experiment with anal sex? Watch the full clip in my store!
big boobs, milf, big butts, big tits, big ass
Download link ----> Mom's Anal Diary Teaser - January 02, 2021 - 192.59 MB
Mommie Bella and I use our big, beautiful breasts to compel you to wear diapers and act like a widdle babie boy! We’re both naked except for some sexy little hostess aprons, just like your fantasy Mommie would be. We have so many fun and humiliating toys packed away for you in that big, pink diaper bag and you can see even more hidden around our adult babie nursery.
Gently stroking our big, soft breasts and nipples, we give you a bottle, make you wear a humiliating “Crybaby” bib, and even put you into a thick diaper with lots of babie powder. We sprinkle some of that wonderful powder all over our breasts and rub it into each other, inviting you to watch and telling you about all the wonderful things that happen to boys who do everything that they can to make their Mommies happy.
To give you just a taste, we both put their hands inside of your diaper and rub you, making delicious crinkling noises until you have an accident and cum all over yourself and your Mommies. What a lucky widdle boy you are! Even if you were being really fussy at first. We’re so happy that you’ve come around and realized how sexy your diapers can be
diaper, diaper fetish, taboo, adult babies
Download link ----> ABDL Breastnosis by Mommies Penny and Be - January 08, 2017 - 1.35 GB
Every single time I take you around my friends, you completely humiliate me! Even when I tell you what to say, how to act, what to do, you still find a way to embarrass me. My friends are sophisticated people, okay? You can’t keep babbling about your “job” testing video games or get caught staring at my best friend’s tits! But I hate to give up on you. And, hey, maybe I’m the problem, right? Maybe instead of holding you up to my expectations, I should just let you play video games all day. In fact, why don’t you go fire up the console and I’ll bring you a soda. A weird blue soda that tastes kind of funny. Did everything just get blurry? And why are your limbs so heavy all of a sudden?
The next thing you know, you wake up in our bedroom. I’ve placed a lot of strange things around: babypowder, a pacifier, and a thick pile of diapers! Not to mention the sexy little apron-lingerie-thingie that I’m wearing. I keep pitching crazy things: You should use a pacifier and not speak while it’s in your mouth. You should pee in your diaper. You should get hard in your diaper. You should love your diaper. You can’t seem to say no to me. Everything I say just seems like a great idea and you find yourself powerless to resist!
femdom, diaper, diaper discipline, diaper fetish, femdom pov
Download link ----> Conditioning You to Love Diapers - May 10, 2021 - 3.58 GB
I can’t believe you want to watch another superhero movie! Can’t we watch something that Mommy wants to watch? What would it take for you to give me the remote for once? Let’s make a deal: I’ll give your big, hard cock a nice blowjob and tittle fuck if you give it to me! No? Okay, I’ll let you fuck Mommy’s tight, wet, cummy pussy for as long as you can last…AND I’ll let you put your cum wherever you want, if I can have the remote for the rest of the evening. Do we have a deal, sweetie?
pov, milf, older woman / younger man ., pov sex, mommy roleplay
Download link ----> Mom Fucks You for the Remote - July 16, 2021 - 4.59 GB
I hope you are as excited as I am for our little vocabulary study session. I am sure you will get plenty excited once we start and it will be easy to see it in those pants you are wearing. Remember the rule is that for every word you get right Step-Mom will flash you or take something off. Was the thought of seeing these big tits and round ass enough motivation?
If you do well enough to get me all naked then I might just do something to your dick that is so stiff from all this learning. A good job on your test equals a blowjob in my bed so you better be studying hard.
blow jobs, joi games, strip tease, taboo, mommy roleplay
Download link ----> Flash Cards and Fellatio with Mom - July 12, 2020 - 635.61 MB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
pov, facials, big tits, taboo, mommy roleplay
Download link ----> FREE Cum Home to Mommy - August 22, 2022 - 163.43 MB
I understand that you had a bad dream, sweetheart, but you need to be rested for work tomorrow. Your imaginary friend is back and he wants to do dirty stuff to me? I thought you grew out of that little game decades ago. I suppose I could indulge you, just this once.
Of course, he wants me naked because he loves my breasts. Now he is very hard and wants me to stroke him off. I did not realize your imaginary friends had such a huge cock, let me just adjust my grip to fit his big thingy in my little hands. I guess I better suck him off too. You are such a naughty boy. Sorry, I mean Mr. Bing Bong is so naughty. He wants to stick his fingers where exactly? Oh, both my pussy and my ass, I should have known. Playtime with your imaginary friend is getting very real so I think it is time you tell me how he wants me to make him cum.
erotic magic, pov sex, taboo, ghost fucking, mommy roleplay
Download link ----> Mom Fucks Your Imaginary Friend - January 19, 2020 - 653.5 MB
I knew the little blonde baby doll named Ella that my husband had left me for was a clueless tramp but I did not realize she was an immature little brat as well. First, she couldn't even be bothered to put her phone down to answer the doorbell and then I find out she has been touching my stuff. Right as I am really starting to give the empty-headed hussy a piece of my mind, she proves she does not belong in the same discussion as a grown women such as myself, by wetting her little panties in fright. Apparently I am more intimidating and she is even less mature than I realized.
I am not going to waste this amazing opportunity for some humiliating revenge so I quickly tie Ella up and leave her to squirm in pee soaked short shorts while I gather some supplies. What would be more embarrassing than wetting yourself in front of your boyfriend's sophisticated ex-wife? What if that ex-wife swapped out your wet big girl panties for a nice puffy diaper? I wonder if my ex-husband will still be so excited for Ella when he finds her sweet little pussy all padded up and covered in baby powder.
diaper discipline, humiliation, jeans/pants wetting, lesbian domination, older woman / younger woman
Download link ----> Diaper Humiliation For Home Wrecker Ella - May 24, 2019 - 899.19 MB
It seems Dr. Barber referred you to me for a diaper prescription and none too soon, since you appear to have wet your pants. You are already diapered and in plastic pants? You must be quite the little wetter to have soaked through to your clothes. I can change you right now with one of your new diapers.
I was clearly correct about you being a "little" wetter. I would have never thought a penis that small was erect if I did not feel the stiffness myself. I am not sure I should fill this prescription till I know more about your diaper fetish. Don't try to deny it with your little diaper boner sticking straight at me. I am going to diaper you then I am going to strip naked and diaper myself. I think the reaction of that cute little stiffy of yours will tell me everything I need to know.
milf, diaper discipline, diaper fetish, jerk off instruction, doctor
Download link ----> Doctor Tests Your Diaper Fetish - May 29, 2020 - 519.38 MB
How is my widdle latex sissy doll doing? Is she so excited to see Mistress in her latex gloves, panties, and garter belt? Do my fully fashioned stockings make your little sissy heart go pitter patter? I hope so, and I hope that you’re responding to arousal by wetting your latex panties like you’re supposed to. I tease and humiliate you over what a horny little fetish doll you’ve become. I especially tease you with my gorgeous, latex ass, shining it right in front of your eager eyes and demanding that you stroke yourself to me, making you have a creamy orgasm before I inform you of a change to your latex training: from now on you’ll be wearing a diaper! Why did you think that I was encouraging you to wet your panties when you get excited? Look how embarrassed you are! I love it when you blush
latex, joi, diaper fetish
Download link ----> Latex Mistress Diapers Her Fetish Doll - February 14, 2017 - 1.76 GB
I must say that you’re just as attractive in person as you were in your application. But do you really think you’re ready to be Penny Barber’s submissive? Strip for me and let’s find out! I pull out a pink trial collar and you immediately begin to fuss. But we’re just getting started and I know exactly what to do with a fussy widdle sissy. Out comes the diaper you’ll be wearing for my amusement. I tease your tiny prick with my voluptuous body as I slide the diaper beneath you. You watch me rub oil all over my big, beautiful breasts before I lock your diaper onto you and make you crawl around in front of me. You watch me masturbate to a delicious orgasm before I check your diaper. Still no pee? Maybe you’ll have an easier time going if you have some of Mommy’s! I fill a bottle up with my golden nectar and make you drain the whole thing before vibrating your widdle stiffy through your diaper. Now you’re going to cum for Mommy, and then you’re going to agree to do anything Mommy wants like an obedient, diapered sissy girl. XOX
diaper, diaper discipline, diaper fetish, sissy training, sissification
Download link ----> Sissy Trained to Cum in Diapers - November 25, 2022 - 4.58 GB
Good morning, sweetheart, I think you might be having a naughty dream about me again. That would explain why I am wearing this sexy lingerie and your dick is twice its usual size. If I am your wet dream version of myself then I guess I should suck that fat cock of yours right now.
Do you think my big, soft breasts would even feel this good sliding up and down your dick in real life? You will probably never find out so I better make this time count. Between my tits isn't the only place I want to stick that cock during this dream, though. I don't plan to let this fantasy of yours end until well after I feel you in my pussy.
milf, erotic magic, pov sex, taboo, mommy roleplay
Download link ----> Dream Mom Fucks You - June 21, 2020 - 551.71 MB
I really do enjoy tutoring but some little troublemakers need discipline to help them focus. I find diaper discipline to be very effective and my students find it to be very embarrassing. If your girlfriend, Kiki, can't stop flirting and flashing then maybe being powdered and diapered in front of each other will get your minds off your hormones and back on your studies.
Kiki seems suitably humiliated at being treated like a baby but when I start to strip you down for your diapering we see that you are sporting a stiffy. I don't know if watching Kiki get diapered made you hard or maybe you are just that excited to lose your big boy pants. Either way, Kiki does not seem to mind that you are a kinky little pervert. I could just tape your little boner down but I want your focus on homework, not how good your hard dick feels in a soft diaper. I have a way to make Kiki even more embarrassed and hopefully clear your mind for a while. Even if it doesn't work perfectly, at least we won't need to stop for any more bathroom breaks.
cum play, diaper discipline, diaper fetish, embarrassment, lesbian domination
Download link ----> Diaper Punishment for Kiki and You - February 21, 2020 - 479.87 MB
Watch the full clip in my store! XOXO
feet, barefoot, foot fetish, footjobs, mommy roleplay
Download link ----> FREE Footjob from Mommy - June 18, 2021 - 150.84 MB
I called you in here when Mom and Dad were out to tell you something. I’ve been waiting your whole life to tell you. You see…I’m not really your sister. I’m your mother. At first you can’t believe it, but then the whole story just comes pouring out. I really loved your Dad—and you look so much like him. Confessing this to you has made me feel so much closer to you. It’s this special secret that we share. I mean, you’re still my brother, but you’re also my son and you look just like my first love. It’s like you’re everything for me. … And I want to be everything to you, too
mother’s day, sisters, taboo
Download link ----> Sister Confesses: I'm Actually Your Mom - October 20, 2017 - 1.74 GB
I am so excited to show you these lacy white panties I wore just for you, Daddy. I can't wait for you to keep training me to be a good girl for you. You even brought me a present! Wait, why is there a diaper in here? That was one time and only a little! This is so embarrassing, please don't make me wear a diaper.
What do you mean you are going to make me do a lot more than wear it? Yes Sir, I will do whatever I am told like a good little girl for Daddy.
daddys girl, diaper fetish, squirting, daddy roleplay
Download link ----> Daddy Decides I Deserve Diapers - November 10, 2019 - 686.53 MB
In an alternate version of earth, female empowerment has been moving backwards in the last few decades. We are now to the point where sexual harassment is not only no longer illegal, it is a right protected by law. Penny works in HR for a large corporation. She has been instructed to make a training video for female employees with Penny explaining and demonstrating the procedures. She is very gung-ho and totally a company girl. She is very no-nonsense and wants to make a very instructive video. She is not embarrassed by nudity at all and in fact is always worried that the she is not exposing herself enough on the video. Now, ladies, pay attention and learn how to behave in the workplace!
masturbation, big tits, eye glasses, female training
Download link ----> Human Resources Training for Sluts - December 01, 2018 - 1.83 GB
When I show up at Sam’s place for a “meeting” he’s a little thrown off. Before I’m even in the door, I lay into him, listing all the things that he does that annoy me, telling him how he doesn’t even compare to my other employees. I rant and belittle him until I notice that there’s a baby bottle on his end table. When I ask what it is, he immediately pops it into my mouth and I can’t help but swallow the mysterious contents. I start to black out and my mind seems…fuzzy. Suddenly from a baby bottle doesn’t seem to weird. When I finish it, I even start sucking my thumb!
Now that I’m all docile, Sam reveals that he’s been worried about my stress levels for a while and that instead of being fired, he’s going to be my new Daddy! He’s arranged for me to spend a week de-adulting at a local regression nursery where I’ll learn to be the sweet little girl that he knows I want to be. I can only nod and suck my thumb in reply.
When I do get back from the regression nursery, I’m just as Sam had hoped I would be, though there is still a tinge of naughtiness to me. Best of all, he can finally take care of me like he always wanted to, changing my wet diaper and even playing with my adorable, creamy tits
diaper, diaper discipline, diaper fetish, taboo
Download link ----> Bitchy Boss Gets Regressed - April 20, 2018 - 1.84 GB
Follow me on Twitter @pamperedpenny
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brunette, milf, eye glasses, behind the scene
Download link ----> Trying to Explain My Fetishes - August 06, 2017 - 1.73 GB
Our whole family is on vacation together in a rustic mountain cabin. Mom and Dad have decided to visit the little town down the road, but you and I just want to chill in the hot tub--but you seem to have forgotten your swim trunks. I say it doesn't matter if you come in naked, but I'm also wearing an incredibly slutty little micro bikini. You don't want to say anything, but you're worried that you'll get hard. I start teasing you saying that I probably wouldn't even notice. You assure me that I would.
Finally, I propose a bet: if you are, indeed, poorly endowed, I get to choose the next family vacation and you foot the bill. If you do have a huge dick, I'll pay for the family vacation that you want. You agree and drop your pants. ... I can't believe it. No wonder you're always slouching! Your dick is gigantic! I start encouraging you to get hard, stripping out of my already tiny bikini and fingering my ass. I don't care if you are my brother, I want to see how much cum that enormous cock can make
joi, hot tub, sisters, taboo, micro bikini
Download link ----> Family Vacation Bet with Sis - March 31, 2018 - 1.79 GB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
taboo, micro bikini, rope bunny, mommy roleplay, cowbell
Download link ----> FREE Mommy Milkers - October 21, 2022 - 122.66 MB
Watch the full clip in my store! XOX Follow me on Twitter.com/PamperedPenny
diaper, diaper discipline, diaper fetish, erotic magic, fairy tales
Download link ----> FREE Diaper Fairy Sissy Potion - October 28, 2022 - 125.22 MB
What do a string of vicious attacks in a small town have to do with a lonely, busty single mom and her deadbeat, well-hung son? Plenty.
You can’t tell your mom why you’ve been so lazy lately, missing both class and work to nap on the couch all day. You’re not sure how long you can resist her. She looks absolutely delicious.
TEACHING MOMMY A LESSON - BDSM puts your slutty mom in her place — and your cock between her punished tits.
Your mom awakens in your evil lair (i.e. the garage), dressed in some slutty red lingerie and a mysterious, jeweled choker. You inform her that you’ve had time to do a little research of your own and that she won’t be taking control of you again. You have a number of tasks for her to complete, including bringing you a gorgeous young woman to feed on, but first she needs to be punished. It doesn’t matter if she’s your mother, she’s still your servant! You hand her a jeweled butt plug and tell her to insert in while you watch. Then you make her do a humiliating little dance for you. She obeys, but pouts the whole time. No matter. She still looks hot! And, to be honest, you rather enjoy seeing her humiliated.
But it isn’t enough. You want to really drive the message home. You order to her stick out her tongue and expose her perfect nipples and—SNAP, SNAP, SNAP!—you place a clothes pin on each. She squirms in pain, but she’s also turned on. Her nipples are rock hard as she drools all over her nice, soft tits. How can you resist thrusting your cock up between her breasts now that they’re also slippery? The evening only escalates from there, with your mother riding your cock while she dribbles hot wax onto her breasts. The plug in her ass massages your cock as she bounces up and down, coming and moaning like your personal whore. The pleasure builds until you finally release your cum into her wanton pussy and make her yours FOREVER.
bdsm, pov, butt plug, taboo, vampire
Download link ----> Penny Barber - My Son is a Vampire! Final Night - November 01, 2023 - 4.31 GB
I come out of my bedroom for some water to find you on the couch. Did you have a fight with Mom again? You know, I really hate to see you out here on the couch. Do you want to come bunk down...with me? We crawl into my bed, but I'm awfully squirmy. You see, I'm not used to wearing a nightgown and panties. Will it bother you if I take them off?
big tits, daddys girl, pov sex, taboo, daddy roleplay
Download link ----> Don't Stay on the Couch, Daddy - October 21, 2018 - 1.8 GB
You are the worst roommate! But you know what? I’m not going to stand for it anymore. While we play some video games you “accidentally” consume a diuretic or two in your (my) orange juice. Imagine your surprise when you start wetting your pants uncontrollably. Luckily I have something that will help you get through this: DIAPERS.
You say you’re embarrassed, but you’re rock-hard as I lay you down on that puffy, white diaper. It isn’t so bad when I lick and tit-fuck your HUGE erection, but you still want to get me back—and you do. You pee all over me, soaking my tits and face. Is that enough to get even, though? Of course not! That’s why that diuretic “accidentally” found its way into my coffee. It kicks in faster than you expect and I pee all over the floor, thoroughly humiliating myself and thoroughly arousing you.
Since we both need to be in diapers for the next few hours, lets make the most of it! I rub my diapered pussy against your diapered cock, moaning and twitching with pleasure. We fill our diapers with pee and cum for the rest of the afternoon. Maybe you aren’t such a bad roommate after all—or maybe now you’re just going to start swiping my diapers, too.
pov, diaper, diaper discipline, diaper fetish, water sports
Download link ----> Soaking Each Other's Diapers - November 11, 2022 - 4.58 GB
I agreed to do some diaper play with you and be your Mommie, but I wasn’t really expecting to like it. However, the sight of your huge cock in diapers certainly got my interest. It looks so inappropriate for you to have such a gargantuan dick in a diaper. I wet it with babie oil and start stroking it in your diaper, talking about how big and hard it is in your diaper—it almost makes me want to diaper fuck you! I ask to take you in my mouth for a sensual diaper blowjob, but sensing my eagerness you have me take off my dress first so that you can see my big tits while I do it. I get down on my knees and suck you until I can’t take it anymore and need to ride you.
I straddle your diaper and take you in my pussy telling you that, “Mommie’s going to ride that big, diapered cock!” I talk dirty to you while a bounce up and down, my tits jiggling and glistening with excess babie oil. As I pull off and see your cock dirty with my pussy juice, I can’t help but suck it again before putting it back in my pussy. I reach down and rub your crinkly diaper all over my ass, enjoying the plastic sound so much that it makes me squirt all over your hard cock. Good thing we had that diaper!
Do you want me to make you cum in your diaper, too? I give you a really sloppy, mouth-stretching blow job, sucking your cum into my mouth, then spitting it back out into the diaper and licking some of it back up again
big dicks, diaper, diaper fetish, pov sex
Download link ----> Friend Loves Your Big Diapered Cock - February 03, 2017 - 1.72 GB
I am so happy your girlfriend is supportive of your chastity regime. She wants a doctor for a husband almost as much as I want one for a son and she understands that wanking is just a distraction from your studies. She doesn't mind that your Mom keeps your rather small penis locked up almost all the time. It is actually very sweet that she lets you rub your caged little thingy against her leg when the frustration gets too bad.
Are you excited that she is going to watch you get unlocked for strokies today and see your cute little erection for the first time?
sph, joi, taboo, key holding & chastity, mommy roleplay
Download link ----> Mom Unlocks You in Front of Ella Nova - September 22, 2019 - 733.54 MB
I can barely believe my ears when my darling boy says he wants to break off our special relationship. After I just bought these sexy new panties for you too! You should know by now that Mommy does not accept “No” as an answer from her little man. You need to be tied up and taught a lesson about who is really in charge of that dick. You can get mad all you want (pouty look is even kinda cute on you) but can you stay mad while I rub your hard cock all over my soft tits and ass?
milf, blow jobs, bondage, cock tease, taboo
Download link ----> Defiant Son Becomes Mommy's Sex Slave - December 17, 2018 - 897.61 MB
Follow me!
twitter.com/pamperedpenny
instagram @miss.penny.barber
milf, big tits, fantasies, fantasy, behind the scene
Download link ----> My Fantasy Shoots - April 02, 2019 - 1.59 GB
I thought it was embarrassing enough that your Mom thinks you still need a babysitter at your age but then she explained that you need to be DIAPERED at night because you still wet the bed. It was so hard to keep a straight face while I promised to make sure the little boy would be nice and snug in his diaper by bedtime. Do you realize how pathetic you look lying there in your undies waiting for me to tape you into a thick, crinkly diaper?
This situation is pretty hilarious but I think it would be even funnier if you had to spend the whole night in a wet diaper. Maybe I will just pee on it myself before I tape you up. I see that being laughed at and covered in my pee isn’t enough to stop you from getting a stiffy. I bet I can think of something embarrassing to do to your little diaper bulge.
diaper discipline, diaper fetish, embarrassment, imposed ejaculations, taboo
Download link ----> Babysitter Teases & Humiliates Bedwetter - February 14, 2020 - 632.08 MB
As an agent for writers, you have to know when your clients need to be coddled and when they need a firm hand. As a rising young star, Ella Nova badly needs both. Luckily, I have the humiliating diapers and spanking skills to make sure she gets whatever she needs to get her scripts out on time.
Ella may have been fussy when I put her over my knee and pulled up her skirt but it was not long before I got positive results. It is amazing how many pages a precocious young writer can finish once her red bottom has been taped into a puffy adult diaper.
diaper discipline, lesbian domination, pee, spanking f/f, taboo
Download link ----> Diaper Punishment Motivates Ella Nova - September 20, 2019 - 541.02 MB
It is so cute that you think you need me to give you "the talk". I mean, sweetie, just look at you. You are grown up but you aren't really grown up, if you know what I mean. Have you ever even kissed a girl? I really don't think getting laid is something you will need to worry about for a long, long time. Just because you have been getting boners from watching me around the house does not mean that you are ready for the gritty details of sex. Kind of points to the opposite, actually.
I will make you a deal though. Show me that you can even jerk off properly and I will consider answering some of your horny little questions. I might even take my out nice round tits to inspire you. Apparently you have been staring at them all the time anyway.
milf, joi, big tits, sexual rejection, taboo
Download link ----> Mom Teases You About Being a Virgin - November 10, 2019 - 673.09 MB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
diaper, diaper discipline, diaper fetish, femdom pov, humiliation
Download link ----> FREE - Neighbor Makes You Her Diaper Stud - July 14, 2023 - 82.2 MB
I have big plans for our date and they mostly revolve around slipping some serum in your glass while you are not looking. I want to make you into my extremely horny, diaper loving adult baby for a night but nothing turns out quite like I planned. I should have known something was wrong when I start to feel very warm and giggly after a few sips from my own glass.
I suddenly realize that my big girl dress is so silly and I just want to be nakie but it is so hard to take off my own clothes. I start to plead with you in babytalk to put a puffy diaper on my bare bottom but then I refuse to sit still when you try to powder my holes. After you finally overcome my squirming and finish diapering me, you dress me up in the pink diaper cover and fuzzy princess top that I had brought to make you wear. The serum doesn't just make someone want to wear diapers and act like a baby though. It also makes me so incredibly horny that I am totally unashamed to wet and cream my diaper right in front of you.
diaper, diaper fetish, erotic magic, taboo, transformation fantasies
Download link ----> Plan Backfires On Penny - March 01, 2019 - 955.54 MB
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Didn’t I teach you to knock before barging in on people’s privacy? Don’t worry about what I was looking at in this box. Ok well actually Mom might need your help with this box full of anal sex toys. I am sorry but your generation knows a lot more about this kind of thing. I was feeling curious but I really don’t know where to start with all these toys. Butt plugs, anal beads, insertable tails?
Maybe if you can help me with some tips and tricks then I can try out some of the toys right now. If you help Mom learn to take toys up the butt then I might be ready to take your real dick in my ass next.
anal, milf, anal masturbation, taboo, mommy roleplay
Download link ----> Mom Wants Anal Sex Tips - May 05, 2019 - 733.91 MB
I know where my missing panties have been disappearing to and don't bother to deny it. Have you been wanking with them, wearing them, or just sniffing them? You don't deserve a whiff of my pussy even from a pair of my dirty panties. However, you may sniff my ass as punishment for being such a little perv.
I am going to make you into my personal ass worshipping butt boy. The only thing you will be allowed to jerk-off to from now on is my ass in a thong. When I am done with you, you will be more turned on by the sight of my asshole than the feel of pussy. Not that a little butt kisser like you should have to be worrying about pussy anyway.
ass fetish, femdom pov, panty fetish, sisters, taboo
Download link ----> Sister's Panty Obsessed Ass Sniffer - June 26, 2020 - 402.7 MB
I should have guessed what was wrong when I saw you staring at a ruler and crying but maybe your little thing isn’t as little as you think. Maybe Mommy should take a look for herself, just in case. Don’t be shy, I’m just going to take it out for a quick peek. Oh no... well let me see if I can make it a grow a little if you get more excited.
Does not seem like anything I show off or do makes it any bigger but I am not out of ideas just yet. Maybe instead of trying be a strong man with a big cock, you can get girls interested by being cute and little instead. Nothing says cute and little like a “big boy” in diapers! Instead of seeing a disappointing cock when she pulls down your boxers, your first girlfriend will already know you have a precious little winkie as soon as she feels the padded crotch of your diaper.
sph, diaper discipline, imposed ejaculations, taboo, mommy roleplay
Download link ----> Solving Small Penis Problem With Diapers - July 06, 2019 - 310.76 MB
I am really glad you came to visit me at the office today but I am also so tired after this long day, especially my feet. It feels so good to finally slip off these high heels.Well thank you very much, I think I look pretty good in these fishnets as well. I would love a foot rub, you are such a sweetheart.
What would really feel great would be to get out of all these office clothes off so I can feel your fingers on my bare feet. Even with my tits and ass out, I can tell it is my toes and soles that are turning you on. I am sure you thought you were being sly but go ahead and pull out that cock. I want to see how hard you get from looking at my feet and I may even let my special little footboy do more than look.
fishnets, foot fetish, footjobs, taboo, mommy roleplay
Download link ----> Mom Indulges Your Foot Fetish - October 17, 2019 - 755.74 MB
I thought I had the house to myself this evening, but instead I look up from my very private phone call to see my son standing there staring at me, demanding that I make dinner no less! We get into an argument and I order you to your room, but later, after that glass of wine (Or three? Four? Gosh, I can’t remember…), I’m feeling much calmer and nicer and…hornier. I slink into your room, changed from my work clothes into a black satin robe and matching nightgown. Do you want to really make up with Mommy? Then let me put my hand down your pants and start stroking that hard cock while you stare at my huge, soft Mommy tits and perky, suckable nipples.
pov, handjobs, milf, taboo, mommy roleplay
Download link ----> Makeup Handjob from Tipsy Mom - November 29, 2020 - 1.78 GB
I just got off of the phone with your teacher, sweetie, and she says you’re grades are slipping. She also told Mommy that you’ll need to have all of your distractions minimized from now on. I’m going to set up your widdle work station with a sippy cup and some crackers, and then I’m going to put you in a diaper so you don’t have to worry about interrupting your workflow to pee! You steal some upstkirt glances at Mommy’s bare pussy while I prepare you, and then I leave you to your paper.
Are you ready to be changed yet, snookums? Oh, you are, but Mommy is going to check your work first. Oh, no! Time to get out the red pen. You sit in your wet diaper and steal more looks up my skirt as I correct your work. Mommy’s going to give you a little more time to fix this, and you are NOT going to be changed until it’s perfect.
Oh, darling, this paper IS perfect! Let’s get you changed into a fresh diaper and…wow! Look at your widdle stiffy poking up there. I think your hard work deserves a reward, don’t you? I lick and suck your tiny little cock before stripping down and taking it between my big pillowy tits. I play little games with it before letting you slide it into Mommy’s tight wet pussy. I ride you until you give Mommy as much cum as your tiny dick possibly can.
Now, how are you doing in your other classes? XOXO
sph, diaper discipline, diaper fetish, femdom pov, taboo
Download link ----> Mommy's Little Diaper Nerd - February 04, 2022 - 4.54 GB
When you walk in on my shopping for a gift for your brother—a brand new car—you can’t take it anymore. You finally erupt, but I do everything I can to reassure you that you, in fact, are Mommy’s favorite. Of course I love your brother, but we have a special connection. And Mommy will go to any length to prove it to you. You want to see my breasts? Sure! You want to feel my mouth on your hard cock? Right away, honey! You want to thrust yourself inside of Mommy’s pussy until you cum? Please do. Mommy loves you so much, sweetie!
pov, milf, cougar, older woman / younger man ., pov sex
Download link ----> Mommy's Favorite - June 10, 2021 - 3.77 GB
I know Alice in Wonderland is your absolute favorite movie and I even enjoy dressing up for movie night but I am starting to have suspicions about your obsession with the scenes where Alice grows into a giant woman. Does somebody get excited at the idea of a big girl making him feel all small? I can't make myself into a giant like Alice but I can still make you feel very little.
Let's play a game where I stroke your cute little cock and every time you start to feel really good it makes you shrink. I want to play with your adorable stiffy until you are tiny enough to get lost in my fluffy petticoats.
handjobs, cosplay, shrinking fetish, taboo, mommy roleplay
Download link ----> Alice Cosplay leads to Magical Shrinking - March 29, 2020 - 663.34 MB
Sometimes actors can get a little too invested in bringing their character to life. When I asked for some help with an audition for a science fiction movie, you were not expecting me to transform into some kind of Nannybot/ sex doll hybrid. I start acting like a robot programmed with the personality of a sweet step-mommy but my only goal seems to be to get you to jerk-off. I flash you my big round tits and talk dirty to your cock but all in my strange RoboMommy style. I know this may not be how you were imagining seeing my naked body but I am not breaking character until somebody cums.
milf, joi, robots, taboo, mommy roleplay
Download link ----> RoboMommy Serves Your Cock - July 19, 2020 - 353.1 MB
I am very excited to begin training you as my new sissy maid. So many wannabe sissies are too lazy and undisciplined to make their fantasy of feminized servitude come true. I can tell you aren't like the other girlie boys, though. We are going to start off by getting you dressed in your precious but very slutty uniform then we can go over all your sissy maid rules. I can see that you are wondering why your uniform does not include panties but I have something much cuter for you to wear under that little skirt. Some soft, pink training panties!
You actually like to be diapered? Well, then that is even better. We can skip the training pants and go straight to a big puffy and crinkly diaper for my new sissy baby maid. I can't wait to see you toddling around on your high heels with your white diaper butt peeking out under your little black skirt. I bet you can't wait either. I do hope you can control your excitement over your new diapered sissy life because I would just hate to have to punish you on your first day.
corporal punishment, diaper fetish, femdom pov, sissy training
Download link ----> Making You My Diapered Sissy Maid - January 03, 2020 - 720.46 MB
Cream for Mommy’s Coffee
Recently you’ve been fighting against the impulse to fuck me, but I can tell that you want to, strutting around in your revealing sweatpants every morning, hard as hard can be. Mommy wants you and I’ll find a way to convince you eventually, whether it’s with my big tits, my squirting pussy, or my bizarre sexual requests. Because I need you all the time. Everything makes me think of your hard cock and your thick come. Speaking of which, this coffee could use a little cream. Why don’t you just stand there, let me get on my knees, and tease out the cream you have for me in your fat balls? Trust me: you’ll love every minute of it!
Timestamps
1:07 Breast and nipple play
4:11 Blowjob and more nipple play
8:01 Doggy style sex
10:59 First squirt
11:29 Second squirt
11:49 Third squirt
12:32 Blowjob-handjob combo
13:27 Titty fuck
13:43 Handjob
14:37 Cum in my coffee!
14:46 Cum eating
pov sex, squirting, taboo, mommy roleplay, pov blowjob
Download link ----> Cream for Mommy's Coffee - December 16, 2020 - 2.14 GB
I am so lucky to have such a darling son who brings me breakfast in bed on Mother’s Day so I don’t have to put on clothes for brunch. The gift you got me is also lovely even if I am not sure what to do with this little, um, sculpture? These Mimosas must be going straight to my head because I am really feeling flushed and I don’t think I can wear this robe another second.
What did you put in this beverage, sweetie? I am starting to feel a really strong need to take off this last bit of clothes I am wearing and I also feel much bolder about admitting that I know your “gift” is a butt plug. Does my special boy want to see me being naughty? Is that why you made your Mom’s bubbly extra special this morning? I have a feeling if I agree to put this plug in my ass then you are going to want put something in my pussy too. They do say a nice hard fuck always makes the best Mother’s Day present.
milf, butt plug, magic control, taboo, mommy roleplay
Download link ----> Special Mimosa Gets You Mother's Day Sex - June 16, 2019 - 745.55 MB
It’s Friday night and you’re going out with your girlfriend again?! Can’t you just tell her that I grounded you or something? Isn’t there anything I can do to convince you to stay in? It’s been weeks since we had sex and I’m absolutely desperate for your cock. … What do you mean it’s over? You can’t dump me! I’m your mom! You know what? I’m still your mother, and if I say you’re going to stay home and fuck me, then you’re going to stay home and fuck me, young man! In no time at all, my big, soft Mommy Milkers have you nice and hard, unable to resist. I hold you down and use your hard cock, clamping your hands against your sides. Wouldn’t this be better if you got to feel my soft tits and warm skin? When you admit that you’re Mommy’s special boy, I give you a special kiss, taking your gorgeous cock into my mouth—and when you admit how desperate you are to cum inside of me, I let you do that, too.
Timestamps:
2:55 Dry humping and dirty talk while Mommy holds you down
5:18 Tits out
10:42 Blowjob
16:29 Ass tease / panties off
17:37 Cowgirl sex
21:19 Simultaneous orgasm
milf, big tits, pov sex, mommy roleplay, pov blowjob
Download link ----> You Can't Break Up with Mommy - March 30, 2021 - 3.3 GB
I know I should let you study but it is just so much fun to tease you. It must be impossible to focus on your class with my big beautiful tits bouncing in your face. I wonder if any of the girls from your class recognize the facial expression of a boy with a raging hard-on. I bet they wouldn't guess it is because your Step-Mom is massaging your cock over your jeans. Or maybe it was watching me play with my fat wet pussy that got you so excited.
I will make you a deal, sweetie. You do your best to focus on your online lecture and I will do my best to take care of that big stiff dick without your class finding out you're getting a blowjob.
blowjob, milf, big tits, cock tease, taboo
Download link ----> Mom Sucks Your Cock During Online Class - June 28, 2020 - 669.86 MB
I’m sooo excited to play today! You get to see ALL of the different types of diapers in my extensive collection. I pick an adorable teddybear diaper for you that matches an equally adorable glass teddybear butt plug! After getting you all pampered up, a heart shaped plug goes into my own tight tushy. I put on my pretty pink unicorn diaper and then rub my incredibly wet diapered pussy against your achingly stiff diapered cock. We both wet our diapers and I’m so turned on that I make you watch me masturbate with my vibrator before I change you. I take your beautiful cock deep into my mouth and pee a little more every time it hits the back of my throat! When my diaper is as full as it can get, I lube up your cock and we fuck nine way from Sunday until you cum all over my pussy. This is exactly the diapered fuck-fest I was hoping for! XOXO
butt plug, diaper, diaper fetish, pee, pov sex
Download link ----> Diapered Fuck-Fest - October 08, 2021 - 4.6 GB
I am excited about all the fun we can have tonight but I do have a question about all this baby stuff I found. I don't see why your Step-Mommy would leave all these diaper changing supplies right here if she didn't want me to find them. A bedwetting problem would explain why she hired a babysitter for a boy your age.
Honestly, I think these diapers are totally cute and it is really precious how shy you are about needing them. Maybe we should put you in one right now, just to get the embarrassment out of the way. Lie down and take off all your clothes like a polite and obedient little bedwetter. If you do everything that your babysitter says then I might even let you have a special big boy treat in your diaper before I am done playing with you.
sph, diaper discipline, diaper fetish, masturbation games, taboo
Download link ----> Babysitter makes You Wank in Your Diaper - July 17, 2020 - 1.01 GB
It’s here! Today is the day you wear your diaper in public. Mommy-Dom is going to take you to the Kinky Fair. Before we go, I dress you up in the girliest diaper and the girliest outfit in my collection. I love the way your little thingy bounces when it gets attention. You seem a little nervous outdoors, but you get to hold hands with the hottest Mommy-Dom at the fair. You wet yourself like a good little sissy and I take you home to reward you with a change and your very own pretty pink collar!
diaper, diaper discipline, diaper fetish, femdom pov, public outdoor
Download link ----> Earning Mommy's Collar - June 10, 2022 - 4.12 GB
I think it is so sweet that you guys are having one last rest over before college starts but your mom did send over some special supplies and instructions for you. Now don't be too embarrassed but I am going to need to diaper you so please strip and lie down. What did you just call me?!?
Okay mister bedwetting potty mouth, you just made this a lot harderfor yourself. If you think wearing a plain white diaper under your pajamas was the most embarrassing thing your mom gave me permission to make you do tonight then you are sorely mistaken. Also, if you hate the idea of being diapered by me so much, why do you suddenly have a little stiffy?
milf, diaper discipline, imposed ejaculations, humiliation, taboo
Download link ----> Diapered at the Sleepover - October 18, 2019 - 741.5 MB
I am so annoyed that Chad, one of the hottest guys in school, just cancelled our date! My bad mood is not improved by my stupid brother, Sam, sticking his nose in to my business to ask why I am so upset. Since he is so eager to make me feel better I have a great idea where he can stick his nose: up my ass instead of in my business. I do feel a little more cheerful after I throw him down and squish my butt on his face so that he can't even talk. Sitting on a dork and playing with his little dick is not half as fun as getting railed by a stud with a huge hard on but it is better than nothing. Maybe my spazz of a brother isn't so useless after all.
Sam might have a smaller cock than Chad but it certainly gets very stiff when his sister puts it in her mouth. Plus, there is the added bonus of knowing he can't stop me from using it, even if he tried. I make sure to rub his helplessness in his face while I ride his dick to a pretty decent orgasm. Sucking and fucking my brother might just be my new favorite way to masturbate, whether he likes it or not.
role play, face sitting, femdom sex, sisters, taboo
Download link ----> Mean Sister Uses Brother' Cock - May 12, 2019 - 657.45 MB
I’ve been feeling very feminine lately, which means that I want to dress you up in the girliest, cutest little diapers I could find! Since I control your cute little cock, we both know that I can dress it up in whatever hyper girlie, soft, adorable things I want. I’ve also decided that it’s gross and boyish when that cock comes, but of course I can still come whenever and wherever I want. For example, right now…and in your blushing face! If you do a very good job, I might let you have one, tiny little orgasm after all—with some stipulations.
Timestamps
2:22 Diapering you
4:08 Babypowder
10:10 Dressing you up
12:38 Penny masturbates
14:00 Worship Penny’s panties
15:15 Tits out
16:53 Panties off
17:10 Pussy worship
21:35 Penny rides you
26:14 Penny cums on your diaper
diaper, diaper discipline, diaper fetish, face sitting, femdom pov
Download link ----> Mommy Dom's Diapered Pussy-Licker - December 30, 2020 - 3.95 GB
Watch the full clip in my store! XO
pov, nerdy girls, school girl, creampie, nerd
Download link ----> FREE Mom Fucks You in Her School Uniform - July 06, 2021 - 169.98 MB
Your new breasts I made you get look absolutely wonderful, darling! Almost as nice as mine. You are looking more and more like my girly little sex toy every day. I lick and such your gorgeous new titties, smearing my red lipstick all over them, claiming them as my own. Your sissy cock swells in your feminine, pink diaper as I describe all of the humiliating things I’ll be making you do with your perky, new tits.
I take your diaper off and stroke your embarrassingly stiff cocklette while I prepare your tight, little asshole for a thorough fucking with MY big cock! But I’m not a mean Mistress: I use lots of slippery lube first, working my way from finger to fist as you lose your mind with pleasure. Of course, you’re not allowed to cum, no matter how much sissy wet leaks out as I milk your prostate.
I tease you with a sexy little dance as I don my massive strap-on. You’re not sure if you can take it, but I am! I bend you over on your diaper for the fuck of your life and reach under you to stroke your erection. My hand sliding up and down your shaft coaxes you to take my fat dick deeper than you imagined you could. I tease you, spank you, and ride you until you prove to me what a good girl you are.
And WHAT a good girl! I think you’ve earned being in diapers for the rest of the week, little sissy.
latex, strap-on, diaper fetish, femdom pov, anal play
Download link ----> Penny Barber - Be My Diaper Fetish Doll - June 09, 2023 - 4.36 GB
I understand that you wish your little chastity cage could come off sometimes but we both know that is not really what is best for you. If your adorable little thingy could get all hard and stiff then you might start having certain boyish expectations that just are not very realistic. You are so much better off being soft and sweet in short skirts and pretty panties.
That does not mean you never get to have little cummies as a treat. You just need to get your orgasms in a way that is appropriate for a sissy. Why don't you lift up that little skirt and let Mom show you how good a vibrator can feel, even on a locked up little clitty.
sph, chastity devices, taboo, sissification, mommy roleplay
Download link ----> Mom Wants You Sissified and in Chastity - March 22, 2020 - 707.22 MB
Letting little sissies and pathetic pantyboys out of chastity is not something Mistress does without good reason. If you want to play with your little sissy stick you need to convince me by showing just how willing you are to humiliate yourself. I know you would wear these embarrassing frilly panties for me but what are you willing to do once you have them on?
chastity devices, fetish
Download link ----> Chastity Humiliation Tasks - December 30, 2015 - 1.14 GB
I know I seem like the perfect little Stepford wife, but I have a kinky side, too. Between chores and block parties, I still manage to find time to make a margarita, pull out my secret stash of diapers, and pee and vibe myself to a deviant, padded orgasm—and my husband doesn’t have to know! Everything’s fine, that is, until YOU creep into my backyard and catch me. But you are kinda sexy, not to mention hung. So long as you can keep a secret and aren’t too weirded out by my ABDL fetish, maybe we can come to an arrangement, stud.
Noticing the impressive size of the bulge in your pants, I offer to let you join in my perversion, sliding a fresh diaper under you before stroking and sucking your beautiful cock to my heart’s content. I get so aroused that I start rubbing my pee-soaked diaper against your big dick while riding my vibrator to another naughty orgasm. I tape up your diaper and we rub my diapered pussy against your diapered cock until you ejaculate so hard that your cum escapes its pampered prison. Licking it up off the plastic, I decide that you have definitely become my new favorite neighbor. Come over anytime! XOXO
milf, diaper, diaper fetish, cheating wife, pov blowjob
Download link ----> Cheating Diapered Housewife - September 23, 2022 - 4.51 GB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
milf, diaper discipline, diaper fetish, femdom pov, humiliation
Download link ----> FREE Click, Click, Piss - August 05, 2022 - 99.4 MB
I’ve got a special night planned for you, sweetheart! I’m going to pamper your pretty little sissy bottom over an adorable diaper. You just lie back while Step-Mommy teases you with powder and special bottle before preparing your cute tushy — one finger at a time — for a sensual sissy pegging. Watch my big beautiful tits bounce in your face as I make your little butt mine and rub my hard clit against the mattress to a delicious orgasm. After diapering you up, I give you the privilege of licking Step-Mommy’s pussy to another juicy orgasm in your pretty sissy mouth. I think you should wear that diaper for the rest of the night, darling. XOXO
pov, milf, diaper, diaper discipline, pegging
Download link ----> Pegged & Pampered - August 26, 2022 - 4.0 GB
It’s your game night, but Mommy wants a little attention. Your friends will be here soon, but when I come prancing out in a chainmail bikini, you agree to put aside your dice and graph paper for a moment. Looking like a Frank Frazetta pinup, I get down on my knees and start blowing you. Hopefully I finish sucking all the cum out of you before that doorbell rings!
pov, milf, nerdy girls, mommy roleplay, pov blowjob
Download link ----> Barbarian Babe Mommy Wants Attention - January 20, 2021 - 1.8 GB
When you walk in on me with your best friend from high school, you see that not much has changed. He's even wearing his old football jersey. I may have asked him to try it on for me. What can I say? It's a fantasy! And one that looks like it might come true. You watch me caressing his body, sliding my hands over his six pack, down to his hard, long cock. You want to look away--you try to look away, but there's something entrancing about watching your own mother doing something so dirty. I tell you not to watch as I stroke his big dick, teasing him closer and closer to blowing his cum all over my big, soft tits. You're such a little pervert. Even as I humiliate and denigrate you, you still watch, mesmerized as I, your usually loving mother, show you what a cum-loving slut I really am
handjobs, milf, cuckolding, humiliation, taboo
Download link ----> Mom Cucks You with a Football Player - June 24, 2018 - 1.76 GB
Hey little buddy, I think you partied way too hard to drive yourself home. You are welcome to crash here with me but only if we take some precautions. Ella kind of told everybody about how you wet her bed so I’m not risking it. Don’t worry, I happen to have a cute diaper in your size left over from an old sorority hazing.
You sure are fussy but your dick is definitely getting hard while I put it in a diaper. Maybe it’s just from the view of my nice round tits. Well I am certainly enjoying teasing you with baby talk so I might be willing to let that little cock get a lot closer to my big breasts. Only if you promise to be a good diaper boy for me though.
big tits, cock tease, diaper, diaper fetish, embarrassment
Download link ----> Invited to Spend the Night in a Diaper - November 22, 2019 - 520.55 MB
Watch the full clip in my store! XO
diaper, diaper discipline, diaper fetish, femdom pov, tease & denial
Download link ----> FREE Mommy's Little Monster - October 19, 2021 - 223.83 MB
I can see you adjusting your semi-hard penis over and over again, sweetie. Mom can take a hint, you're feeling a little itchy for an orgasm. I just want to relax after a long day so maybe you can wait to deal with your erection alone in your room later. Don't give me that look.
Fine, fine, fine. I will stroke you off real quick but you better shoot fast and not drag this out. I guess that is a good point, you horny little beggar. You probably will cum faster from a handjob if Mom gets naked while I touch your cock.
ass, handjobs, taboo, mommy roleplay
Download link ----> Begging Mom for a Handjob - March 15, 2020 - 584.12 MB
Are you wondering about the big bulge in Mommy’s short shorts? Maybe feeling a little jealous of the size of it? I am happy to show you mine, if you show me yours...BUT whoever has the smaller dick has to give the other person a blowjob!
I hope you are not too shy to compare your cute little erection to Mommy’s huge cock. We can even stroke together for a while to give you a chance to make yours get bigger. Mommy enjoys watching you play with your cock almost as much as I’ll enjoy getting mine sucked!
sph, cock tease, futa, futanari, taboo
Download link ----> Futa Mommy Cock Size Comparison - December 02, 2018 - 276.67 MB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
pov, diaper, diaper discipline, diaper fetish, pee
Download link ----> FREE Soaking Each Other's Diapers - November 11, 2022 - 126.4 MB
I really want you to play baseball this summer so can you please just do it for me? I might be willing to show you an old trick I used to do with my bat if you promise to go to tryouts today with a good attitude. Let's just say it is the kind of trick that requires me to take my panties off and put a condom on this slugger.
I need a minute to get warmed up before I can fit something this size in my pussy so you just sit back and enjoy the show. I will make sure to give you lots of good angles to watch Step-Mom fuck herself with a baseball bat but you better get your butt straight into the mini-van as soon as I finish cumming all over this thing.
masturbation, milf, odd insertions, taboo, mommy roleplay
Download link ----> Mom Fucks Herself with a Baseball Bat - May 10, 2020 - 441.86 MB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
diaper, diaper discipline, diaper fetish, mesmerize, mind fuck
Download link ----> FREE Fucking With the Principal - January 13, 2023 - 131.6 MB
I knew it was risky to fool around with my employer's son and absolutely foolish to try anything when she is home. If she did not want me to tease you then your mom probably should not make me wear this slutty french maid outfit. I can barely move in this thing without showing you my ass, so I can hardly be blamed here.
I was mortified to have your mom walk in on us but I never thought she would bend me over, lift up my skirt and spank me. I thought smacking my poor bottom was more than enough pain and humiliation but then she made me strip so she could poor hot wax all over my bare tits right in front of you. As she lectured me during my punishment I realized she was not just mad, she was jealous. So you got to see me get spanked and I had to watch your mom suck your dick to prove it still belongs to her.
french maid fetish, lesbian domination, spanking f/f, taboo, mommy roleplay
Download link ----> Mom Spanks Maid Then Sucks You Off - June 30, 2019 - 631.64 MB
Buy the whole thing in my store!
diaper, diaper fetish, taboo, adult babies
Download link ----> Diapered w/Girlfriend Trailer - November 06, 2020 - 206.06 MB
I’m here to see your mother, Rain, to discuss your declining performance in school. I want to share with her a secret that many moms have been discovering about how oral sex leads to good grades and better attitudes. I explain to Rain that if your education is important to her she needs to be sucking your cock regularly! Your mom is willing to do whatever it takes to get her son back on track so I help the two of you sort out some agreements about what behavior merits reward head. Of course, in order to really motivate you, it is important you know exactly what you can look forward to once you bring back that stellar report card. I help guide Rain as we take out your cock for the first of many good boy blowjobs.
milf, role play, blow jobs, taboo, teacher fetish
Download link ----> Miss Barber Convinces Mom To Blow You - February 10, 2019 - 842.18 MB
The adoption papers have finally been unsealed and it appears that you have…an aunt! Well, a half aunt. Apparently Grandma had a baby before me who was put up for adoption in Germany. When I invite her to come to America to meet us, it turns out that she has a very different idea of what does and doesn’t count as “family”. Apparently, as her half-nephew you’re free game—and same for me as her half-sister! And it isn’t long before she convinces me that what I really need is some of my son’s fat cock. It turns out that all we needed to live out our taboo fantasies was a little encouragement—and now we have all week to fuck before she’s back to Germany and we have one more family secret!
milf, threesome, kissing, taboo, mommy roleplay
Download link ----> Sharing My Sister with My Son - December 08, 2020 - 3.22 GB
I am glad you are so excited for our date but I am a little surprised you ignored my request about the dress code for this evening. We must have very different ideas about "cute clothes" because I was thinking of something a little puffier than skinny jeans on that cute bottom. I will show you what I mean but first we have to get all these boring clothes off you.
You do look kinda cute in nothing but your little knee socks but don't worry, my favorite part of your new outfit will cover up that precious little stiffy. If you want to go out to dinner with me in this skimpy little dress that my tits are practically falling out of then you have to wear a big, fluffy diaper all night. You also get to wear this adorable "Crybaby" hat, a shirt that says "Bedwetter" across this chest, and more fun accessories to show everyone that you are my widdle baby. I know you think wearing all this will be very embarrassing but with all the baby oil I am going to pour down the front of your diaper, I think you will be too distracted by your little boner to even feel the public humiliation.
handjobs, diaper, diaper fetish, embarrassment, taboo
Download link ----> Penny Wants A Diaper Boy Not A Date - July 19, 2019 - 410.07 MB
If you had known that the punishment for being caught with no less than THREE PAIRS of my panties would be diapering, being dressed like a sissy girl, and humping your pillow to orgasm while worshipping my feet, you would have done it ages ago! And you might just get a chance to do it all over again. After all, I am going to have to tell your sister to keep an eye on her panties with a little perv like you in the house. Have you bitten off more than you can chew, or are you going to be secretly enjoying your time as my foot-kissing, diaper-wearing, pillow-humping sissy daughter?
diaper, diaper discipline, foot fetish, sissy training, mommy roleplay
Download link ----> Sissy Diaper Discipline - April 27, 2021 - 1.7 GB
Watch the full clip in my store! XO
oil, diaper, diaper fetish, lotion/oil fetish, adult babies
Download link ----> FREE Sexy Neighbor Diapers You - July 04, 2021 - 165.82 MB
I'm a lonely housewife, annoyed that my loser, small-dicked husband is never around to take care of me. Can you really blame me for screwing the delivery guy? And so what if I don't want him to wear a condom! It's been so long since I was filled with warm, thick, white cum. I need it so bad that once he does shoot inside of me, I just can't keep myself from furiously masturbating as I order him out of my house.
pov, cream pie, milf, creampie, cheating wife
Download link ----> Fucking the Delivery Guy - April 10, 2021 - 1.27 GB
Hey there, couch potato. Think you can beat stepMommy at a game of basketball? If you win, I’ll buy you that expensive new gym bag, but if I win, you have to do whatever I say for a whole week. Game on!
I guess you’re out of practice, because Mommy creams you! Now you’re going to be my widdle diaper sub for the week. What does that mean? Oh, nothing. Just embarrassing diapers, humiliating little outfits, and granting Mommy unrestrained access to your cock! I tease and humiliate you while I put you in diapers, a onesie, and an adorable bonnet. When you start to fuss, I shove a pacifier in your mouth and spank you—because that’s what you do to sore losers!
When it’s time for a change I open your soggy diaper and reveal your embarrassingly hard cock. I just can’t resist playing with it! I take my top off and show you my big MILF tits while I stroke your aching hard-on with oil. I tell you about all the extra humiliating things I’m going to buy for you to wear this week as you get harder and harder in my hand. You try to resist coming from something so embarrassing, but Mommy knows just how to stroke you and you cum all over my breasts, your warm cream dripping off my hard nipples, into your diaper.
Six more days to go.
milf, diaper, diaper discipline, diaper fetish, femdom pov
Download link ----> Diaper Bet With Mom - February 09, 2023 - 4.22 GB
When Sam forgets to finish his chores it usually just means he wants to end up naked over my lap. Or at least that is the result he most often gets. First I pull down his jeans for the warm up and then his bigboy undies come down for a nice humiliating bare bottom spanking. As Sam's cute little butt his heating up I make him apologize for being naughty and promise to be a good boy for Mommie from now on. Good boys get rewards instead of punishments like having their prostates milked after a spanking. Maybe I will make Sammy go fetch the babyoil so I can give him his reward right now
prostate massage, spanking f/m, taboo
Download link ----> Spanked And Milked By Mommie - October 20, 2016 - 1.35 GB
We’ve just been at each other’s throats ever since I married your father. Yes, I am a lot younger than he is and yes, I have noticed you constantly staring at my breasts and I’m reasonably certain that you’ve been pawing through my bras as well. However, I’ve been doing some research online and I found something that I think might really help us form a bond—not exactly a mother-son bond, but something that leaves room for your libido and for my nurturing tendencies at the same time: Diaper Therapy. It’s rather unorthodox, but I’m ready to give it a try if you are. First, we just need to get you undressed on my bed, a thick, crinkly diaper covering your erection as much as possible, and then it’s time for a little mutual masturbation while you “nurse” on my full, soft breasts. So while it’s a little odd, I really hope that you’ll fully participate. Oh, and maybe we don’t mention this to your father, hmm? Having our own little secret will help us bond even more, after all!
diaper, diaper discipline, diaper fetish, femdom pov, mommy roleplay
Download link ----> Bonding With Mommy - July 07, 2021 - 3.9 GB
Dear Diary, I want to try more things this year, even if my husband is sort of a prude. But where can I find someone who respects my marriage, but will also do all the filthy things that I’m curious about? Maybe…just down the hall! But will my son help me fulfill all my dirty fantasies, starting with sticking his beautiful, hard cock up my ass? I may be a mother, but I’m also a horny little slut! XOXO, Penny
Timestamps
2:56 Mom propositions you for anal sex
5:37 Mom in lingerie
8:08 Butt plug and anal masturbation
14:43 Blowjob-handjob-titty fucking combo while butt plug is in
20:53 Remove butt plug
21:28 Your cock in Mommy’s ass
26:06 Mom has an anal orgasm while you cum in her ass
26:30 Cum play, showing off your anal cream pie
anal, butt plug, pov sex, taboo, mommy roleplay
Download link ----> Mom's Anal Diary - January 01, 2021 - 3.98 GB
My gorgeous stepdaughter needs new photos for her portfolio, but the photographer informed me that the creepy neighbor boy—YOU—photobombed ALL her latest pictures. They’re ruined!
Hell hath no fury like an angry stagemom. I hold you down and strip you out of your clothes. Your stupid little crush on my stepdaughter has got to stop, and I know exactly how to make sure that you know, in your heart of hearts, that you will never, ever get with her.
I cruelly diaper you and dress you up in a humiliating ABDL outfit before I whip out my own camera and click! click! start photographing your embarrassing diaper predicament. Unfortunately for you, your out-of-control libido responds to all the attention and you get a pathetic little erection in your diaper. What’s an angry MILF to do but open up that diaper, stroke you off, and continue photographing your humiliating diaper handjob? If only you could control your orgasms, but it’s no use: I jerk you off in your diaper, and now I have some nice, juicy, CUMMY pictures of you to show my sexy stepdaughter.
milf, diaper, diaper discipline, diaper fetish, femdom pov
Download link ----> Click, Click, Piss - August 05, 2022 - 4.4 GB
What is the perfect present for a submissive little diaper boy? An even more submissive little diaper girl, of course! Isn’t she a pretty little baby? Her name is Alani and she wears diapers and sucks on pacifiers just like you but hers is still dry, unlike yours. I guess somebody was so excited about his new diaper doll that he wet himself.
Good thing Alani can help Mommy with diaper changes. Won’t it feel so naughty to have your little winky powdered by another adult baby? If you are a very good boy then I might even make Alani put your little thingy in her mouth while we change your diaper.
sph, diaper, diaper fetish, femdom pov, taboo
Download link ----> A Diaper Doll for the Diaper Boy - November 27, 2019 - 664.28 MB
After finding taboo porn on your laptop, everything clicks into place as to why you’re always staring at my ass. You just really want to stick your little face in Mommy’s ass, don’t you? Well, we might as well get it out of your system! I let you sniff, kiss, tongue-fuck, and otherwise worship my big, MILFy ass, winking my butthole around your curious tongue. You do such an amazing job, that I even decide to make you feel good, too, first taking your hard cock in my mouth, then allowing you into my pussy as you continue to grope and feel my asshole. You’re so overwhelmed by finally being able to experience your fantasy, that you will Mommy’s tight pussy with your warm jizz!
Timestamps:
2:18 Ass tease
2:36 Shorts off
3:45 Panties (thong) off
5:28 Orally worshipping Mommy’s asshole
9:20 Blowjob
9:35 Tits out blowjob
15:26 Face-to-face POV sex
18:15 Doggy style POV sex
20:52 Creampie
pov, milf, ass worship, taboo, asshole
Download link ----> Worshipping Mommy's Asshole - May 21, 2021 - 3.04 GB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
masturbation, outdoors, pov sex, taboo, mommy roleplay
Download link ----> FREE Mom Flashes & Fucks You Outside - September 02, 2022 - 70.86 MB
You’re adapting to your new ABDL lifestyle so well! You’re meeting all your milestones, like calling me Mommy, I even have something special planned for you. Sex is a reward now, but like all big boy things, Nurse Mommy controls the sex. And I love teasing you with my curvy ass and full tits almost as much as I love embarrassing you with your own diapered erections and orgasms! You can try to resist, but your diapered cock betrays you. You’ll come anywhere I say, no matter how embarrassing or dirty.
diaper, diaper discipline, diaper fetish, femdom pov, taboo
Download link ----> Rx: Mommy Domme - October 24, 2020 - 1.78 GB
Watch the full clip in my store! XO
big boobs, pov, older woman / younger man ., pov blowjob, romantic
Download link ----> FREE Mommy Comforts Her Special Boy - March 19, 2021 - 140.61 MB
Sometimes little diaper sluts just need to parade around the streets in bondage while gagged and padded. I strip out of my big girl outfit of sexy latex right out in the open before taping myself into a big pink diaper for anyone to see. I diaper myself but after I have my hands tied behind my bag and big pacifier stuffed in my mouth, I will not be able to change myself without permission.Of course, that leads to me being fed a bottle of water so I will have no choice about wetting my diaper in public.
public nudity, diaper fetish, humiliation
Download link ----> Pampered Penny On Public Display - August 30, 2019 - 1.4 GB
Your girlfriend, Penny, would definitely laugh at you for starting the morning with sticky pajamas at your age. What would she say if she knew the reason you were moaning and humping the bed all night was a dream about her putting you in a big, crinkly diaper? In the dream she speaks to you in baby talk, drizzles your cock with baby oil, and sprinkles your little bottom with baby powder.
After she gets you all taped up Dream Penny rides your diapered hard-on while she teases you about what real-life Penny would say if she could see how your little thingy reacts to being treated like a baby. Maybe you will have to tell her the truth since she is going to start the morning in a puddle. This diaper dream won't end until your bed is sticky and soaked.
ass, diaper discipline, diaper fetish, erotic magic, imposed male orgasm
Download link ----> Diapered Wet Dream - May 22, 2020 - 491.63 MB
Follow me on Twitter @pamperedpenny
Follow me on Instagram @miss.penny.barber
milf, eye glasses, behind the scene, vlog, mommy roleplay
Download link ----> My Mommy Dom Philosophy - May 01, 2019 - 1.79 GB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
arrogant woman, diaper discipline, diaper fetish, powerful woman, boss
Download link ----> FREE Mean Boss Becomes Diapered Sub - August 01, 2022 - 282.72 MB
I have been so happy with all the improvements you have been making ever since I put on a lock on that cute little cock of yours. It has been hard to make time to check or tease you as often as I would like with all these visitors in town for the holidays though. How embarrassing would it be if one of your cousins walked in on your Mom inspecting your chastity device?
I think everyone has gone to bed so it is safe to take pull your pants down and have some fun with your soft little thingy. Well I guess it isn’t completely soft after seeing me in this lingerie but it certainly isn’t going to get hard either. I know a few minutes with your frustrated but adorable dick squished between my big, soft breasts will have you determined to earn that Christmas orgasm next month.
milf, big tits, taboo, tease & denial, key holding & chastity
Download link ----> Mom Gives You a Holiday Chastity Check - November 18, 2019 - 637.73 MB
Well, look at you all dressed up! Big plans today? You’re going to ask a girl out… okay. That’s fine. This is fine, but get yourself to school today.
I’m waiting for you when you come home. Apparently she said yes, which is… just great. Mommy recognizes that you’re all grown up and have new needs and desires. Why don’t you let Mommy help you indulge in those desires. We’ll start by smoking to calm your nerves. Isn’t that better? Now watch Mommy strip for you. I play with my big juicy tits and rub my pussy over my white lacy panties just to get you nice and hard.
Oh my god, you’re HUGE! That’s the most beautiful cock Mommy has ever seen. I’m going to make you feel so good, sweetheart. I kiss and worship your cock, taking as much of it as I can in my eager salivating mouth. I can’t wait to get it into my aching jealous pussy. Mommy will show you that she can take care of your needs better than any silly girl you meet. I ride you cowgirl to a to a long squirting orgasm before getting on my back and letting you take me as hard as you can. You fill Mommy’s pussy full of your cum. Now go get cleaned up, sweetie, before we take another “smoke break.” XOXO
cream pie, milf, smoking, pov sex, taboo
Download link ----> Mommy's BIG Boy - February 13, 2022 - 4.6 GB
I consider myself to be a very good therapist but I may have picked up a few bad habits over the years. Like using my hypotherapy skills to turn my hottest female patients into sex slaves. I thought I could get away with programming these women to strip naked and sexually service me on command but never thought what might happen if someone else accidentally used a trigger word near one of my hypnosluts.
My dirty secret is finally exposed to the son of one of my clients when she goes into a trance and takes off all her clothes right in front of him. When the son comes to my office to confront me, I assume he wants justice and a cure for his mom, but I am in for an even bigger surprise than I thought. This little delinquent just wants to know how he can control her to satisfy his own Oedipal fantasies. Of course, he also demands that I strip and give him a blowjob if I want to keep my career. I am definitely mad at first but I have to admit this young man is an ingenious pervert after my own heart.
blowjob, milf, role play, blackmail fantasy, taboo
Download link ----> Blackmail Blowjobs From Mom's Therapist - March 03, 2019 - 881.03 MB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
diaper, humiliation, pee, sissy training, collars / leashes
Download link ----> FREE Sissy Trained to Cum in Diapers - November 25, 2022 - 204.25 MB
Hello there, sweetheart, and please say hello to my special guest as well. I know he used to pick on you a lot but he has really grown up into quite the handsome young man. It was his idea to do a video chat so you could learn about our new relationship. We both want you to see your mom unzipping your bully's pants to play with his nice, stiff cock. How does it feel to watch the guy who used to give you wedgies sliding his dick between my big tits?
You can tell us both how it makes you feel when the three of us have dinner together next weekend. Try not to get offended when he makes some "your mom' jokes about all the things he has been doing to my holes. In the mean time, just relax and enjoy watching your Mom give your worst enemy the blowjob of his life.
milf, blow jobs, cuckolding, taboo, mommy roleplay
Download link ----> Mom Blows Your Bully And Makes You Watch - March 24, 2019 - 727.69 MB
I honestly can't believe you came here to hook up when you are wearing a cute little diaper under your pants. No wonder you started acting so shy after I took my big, beautiful tits out. There is something delightfully perverted about that big, hard cock sticking up inside a soft, babyish diaper, though. Definitely not what I was expecting but I think I can still get off on this weird situation.
Does the little diaper boy still want a big boy blowjob? I usually swallow but in your case, I think there is a much more appropriate place to put that nice hot load I plan to suck out of you.
blowjob, big tits, diaper, diaper fetish
Download link ----> Turned On by Your Diapered Cock - March 20, 2020 - 592.53 MB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
pov, milf, blow jobs, female ejaculation, taboo
Download link ----> FREE Penny Barber - Sugar Cookies - January 01, 2023 - 111.54 MB
You’re soooo good to Step-Mommy, sweetie! You let me vent about my creepy boss, you make me something to help me relax, and you bring me my favorite robe. It makes it so easy to get comfortable around you. As you sit with me while I read my naughty book, I get excited and start to touch myself. You get hard in front of me, and I can’t help but tease you with my big tits and ask you to take that nice dick out of your pants and masturbate with Step-Mommy. You follow all of my jerk off instructions while I tell you how good it makes my pussy feel to watch you masturbate. I count down to our mutual orgasms and let you cum all over Step-Mommy’s pink blazer. Maybe my creepy boss will back off if I leave your cum on there and wear it to work tomorrow. What do you think, darling?
pov, milf, dirty talking, masturbation encouragement, taboo
Download link ----> Masturbating With Mommy - April 29, 2022 - 4.24 GB
Watch the full clip in my store! XOX Follow me on Twitter.com/PamperedPenny
pov, milf, orgasms, pov sex, taboo
Download link ----> FREE Vacation Masturbation Frustration - September 09, 2021 - 170.35 MB
I am so flattered you wanted to spend your birthday with your Mom but I think you are pushing the birthday boy thing a little too far. Just because I have had a few glasses of wine does not mean I am going to flash my tits at you in this restaurant right now. You really are a very dirty boy. Maybe a little naughty game of public truth or dare as a birthday treat will be ok.
I can't believe I am showing my bare ass and breasts in public like this but I have to admit I am definitely getting turned on. Do you think Mom can get herself off before the waiter comes back? I know you want to watch me try at least.
masturbation, big tits, public flashing, taboo, mommy roleplay
Download link ----> Mom Gets Naked In Public For You - June 02, 2019 - 717.36 MB
I don't think it is any of your business what I was discussing with the repairman and there is certainly no need to mention it to my husband. Even if you try to make up some silly story about me blowing a stranger in the living room, I am sure your step-dad won't believe it for a second. Ok fine, please just don't tell him. I'll do anything! No, that does not include a blowjob!
I can't believe you talked me into sucking my step-son's dick right in the kitchen just so you will keep quiet about the other dick I sucked. I guess you do have a pretty nice cock, though. One blowjob and you can even cum all over my bare tits but then you better keep this secret forever.
pov, milf, blow jobs, taboo, mommy roleplay
Download link ----> Making Step-Mom Suck Dick for Silence - August 23, 2020 - 2.49 GB
Watch the full clip in my store! XOX Follow me on Twitter.com/PamperedPenny
pov, diaper, diaper discipline, diaper fetish, pee
Download link ----> FREE Seduced Into Diapers - September 02, 2021 - 156.86 MB
This is a very simple panty seduction clip that will have any sissy creaming her frillies. I take out different pairs of panties and explain why I like them on you. More importantly I let you know how I would use your little sissy body in each pair of pretty panties.
femdom, fetish
Download link ----> Pantyboy Heaven - March 20, 2016 - 832.26 MB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
pov sex, taboo, micro bikini, mommy roleplay, pov blowjob
Download link ----> FREE Mommy's Pussy is for Athletes - November 18, 2022 - 103.51 MB
I finally caught you! You wake up helpless in a strange room. It looks like…a nursery? You’re horrified to find yourself bound and at the mercy of your archenemy, Wonder Woman! I’ve neutralized your powers and dosed you with a regression serum.
Get ready for some extreme humiliation as I diaper your evil, criminal bottom and tell you how your life is going to go from now on. I’m going to regress you and raise you to be…my sidekick! You’re furious, but you can’t resist me. The serum is already taking effect and all you can do is protest in babytalk. “Mommy, no!” But I don’t listen. Instead, I gag you with a pacifier gag and dress you like a babie.
But I’m not going to be a cruel Mommy. To help you relax, I decide to fulfill one of your fantasies. I know that you’ve been curious about my big tits. How could I not notice the way that you stare at them? Now just enjoy your bottle so that you can wet your diaper like a good little ward!
But when you turn defiant as I check your sopping diaper and find a hard cock, I decide that you need more discipline and regression. I think that I won’t change you until that erection goes down. After all, you are very tricky. I want to be sure that you’re completely regressed before I touch your little stiffy
diaper, diaper discipline, diaper fetish, supervillain, superheroines
Download link ----> Wonder Woman Captures and Regresses You - May 30, 2017 - 1.75 GB
you know that i’m relaxing outside, taking in a little sun, but you just can’t wait for a diaper change. after teasing you a little bit i agree to come in and take care of you. however, i get to thinking as i do. maybe i want a little diapered pool boy who can bring me [***] and run suntan lotion on my back while he wears only a diaper. thinking about being so humiliated is too much for your little, diapered cock and you cum all over your fresh diaper. mommy tastes your yummy, cummy diaper creamy. you’re such a naughty boy
diaper, diaper discipline, diaper fetish, taboo
Download link ----> Mommie's Diapered Pool Boy - May 12, 2017 - 1.01 GB
Don’t you think I look sexy wearing nothing but my cute, purple diaper and my cute, purple hairbow? In the garden, I oil myself up and rub all over, humping my diaper and massaging my big, soft tits until I have a delicious, padded orgasm.
diaper, diaper fetish, taboo, adult babies
Download link ----> Sexy Diapered Sunbathing - December 12, 2020 - 1.76 GB
Follow me on Twitter @pamperedpenny
femdom, eye glasses, femdom pov, behind the scene, vlog
Download link ----> Do You Want to Be a Submissive in 2019 - December 07, 2018 - 1.82 GB
[spoiler=You Belong in Diapers | Penny Barber - December 10, 2021 / 4.43 GB]
Guess who got ahold of your browser history, darling? Someone has been sitting around playing video games all day — and masturbating to diaper porn — while I’m at work! So I’ve decided that you belong in diapers. I bend you over my knee and give you the spanking you’ve had coming while telling you how things are gonna be from now on. I strip down, oil us both up, and laugh as your stiff little prick jumps every time I tell you to call me…Mommy! You finally put your mouth to good use and go down on me as you hump your diaper, coming in it right as you make me come.
Now, I’ll only change you AFTER you’ve finished all your chores.
pov, diaper, diaper discipline, diaper fetish, femdom pov
Download link ----> You Belong in Diapers | Penny Barber - December 10, 2021 - 4.43 GB[/spoiler]
Mommy's not so sure that she likes you having a girlfriend. And I don't see why you need one anyway. I'm willing to do all the things that she can do for you--and I'll do them better! Housework, cooking, sex. Does she offer you daily wake-up blow jobs like Mommy does? No? Well, I'm going to call her right now and you're going to have to decide whether to ask her if you can move in...or break up with her! Of course, I know my son pretty well and I have an idea of just how to elicit the action that I want. I'll just open up your pants and start stroking your hard, gorgeous dick.
Note: There may be some slight pixelation here and there, hence the decrease in price. I am currently looking into troubleshooting the issue and perhaps purchasing a new camera. I watched it myself and had Sam Solo quality check it and I don't believe that the glitches here and there are that bad. Sorry and I hope you enjoy it anyway
handjobs, milf, cougar, home wrecker, taboo
Download link ----> Mom Jerks You to Dump Your Girlfriend - July 22, 2018 - 1.81 GB
I love showing off my toys to my friends, especially submissive little sex toys with adorable cocklettes for us to decorate! Ella Nova and I want to make your stiff little winkie even more precious before we put it in a diaper so we get out our craft supplies while we have you all naked and helpless. We add cute tickers on the tiny balls, tie some pretty bows with ribbon that has a very special message written on it, and even attach some bells so we can hear you tinkle with every step or stroke.
Most cocks would shrivel up with humiliation after all that but this naughty thingy stays hard no matter how how silly it looks. Once we are ready to diaper you up we remove most of the decorations from our toy but Ella and I make sure your cute little winkie is still covered in something embarrassing before it gets diapered.
sph, diaper, humiliation, pee, taboo
Download link ----> Winkie Humiliation During Diaper Change - February 15, 2019 - 841.71 MB
Have you ever wanted to cuddle up with me in front of a fire and just enjoy the sensuality being diapered together? No? Well, what if I make you hot cocoa with tiny marshmallows, too? Yay! Come snuggle up with me for some indulgent, diapered mutual masturbation. Trust me: nothing feels better than coming in a freshly wet diaper while youʼre cuddled up against my big, soft tits, but youʼre welcome to compare it to my eager mouth and skilled hands!
Time Stamps
Diaper upskirt 1:17
Breast fondling over sweater 3:58
Nipples out 4:53
Diaper rubbing 5:51
Penny strips down to her diaper 6:35
Penny diapers you 7:12
Open diaper hand job with babyoil 7:30
Open diaper blowjob 8:30
Combination handjob-blowjob with diaper 9:04
Babyoil on tits 10:00
More combination handjob-blowjob with diaper 10:24
Handjob against Pennyʼs diaper 11:05
Open diaper titty fuck 11:30
Blowjob-handjob dirty talk 11:56
Babypowder handjob 13:21
Side-by-side diaper humping 13:43
Penny wets her diaper 15:44
Penny encourages you to wet your diaper 16:01
Wet diaper masturbation and nipple play 16:06
Diapered pillow humping 16:53
Penny gropes your wet diaper while masturbating 17:15
Diaper humping with nipple licking 18:04
Diapered orgasm 18:21
Afterglow 18:42
pov, diaper, diaper fetish, pillow humping, adult babies
Download link ----> Diaper Sex in Front of the Fire - December 22, 2020 - 2.86 GB
Your date got tired of waiting and finally left. What is wrong, honey? You were so excited about your first date. Oh. That is just silly. It can’t be so little that you are scared to even go on a date. I am just going to take a look because I am sure your dick is not nearly as small as you think.
Ok, well, even Mom is wrong sometimes. You really do have a tiny cock. It’s cute though and it sure does get very stiff. I think I know how I can cheer up my little man and his very little man. You penis is a little small for a handjob but I can give you a nice two finger job though. I bet you would also really love to find out easily Mom can fit your entire tiny thingy in her mouth.
sph, small penis encouragement, taboo, mommy roleplay
Download link ----> Mom Takes Pity On Your Tiny Cock - September 01, 2019 - 612.13 MB
It's laundry day and I'm picking up the clothes scattered around--mostly panties. I can't help but tease you, wearing nothing but a low-cut top and panties. You just get so excited! I have you start stroking your cock for me, but I also want you to sniff my dirty panties while you do it. Your panty fetish is so strong that you'd do just about anything that I ask you to. From licking up your precum to shoving a toy deep into your sissy ass, I tell you all the dirty, kinky things you need to do as I masturbate along with you until we both cum hard in my wet panties
joi, bra & panties, jerk off instruction, panty fetish, satin panties
Download link ----> Laundry Day Panty JOI - July 01, 2018 - 1.81 GB
There’s just so much to do! I wish I could wind down, but instead it’s a glass and these new pills my doctor prescribed. Oh…you’re not supposed to mix them with booze. Oops. *** You know, for some reason I feel like my inhibitions are way down and I can think of one thing that will really relieve my stress: that huge, candy cane bulge in your pants! Maybe it’s weird that I’m your mom, but who cares, right? It’s the holidays! And I just need to get fucked so that I can come super hard like the little slut I am!
Timestamps
3:25 Christmas lingerie and dirty talk
6:43 Panty removal
8:12 Masturbation
10:19 Squirt
10:54 Blowjob
13:12 Naked
13:42 Handjob
14:17 More blowjob
16:47 Missionary sex
22:07 Creampie and cum play
pov, milf, christmas, pov sex, mommy roleplay
Download link ----> Relieving Mom's Holiday Stress - December 24, 2020 - 3.29 GB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
strap-on, butt plug, diaper discipline, diaper fetish, femdom pov
Download link ----> FREE Invaded & Degraded - August 17, 2022 - 228.09 MB
You were supposed to be here in 30 minutes or LESS, pizza boy. Looks like your next delivery is going to be late by a whole diapering! I drag you into my home, throw you on the floor, and strip you down to your birthday suit, except for that stupid hat they make you wear! Between taking bites of my lukewarm pizza and toying with your cute little thingy, I pull out a big soft diaper and slide it under your late ass.
You probably feel like being diapered is punishment enough, but we need to make sure you take your job seriously from now on, meaning I’m in charge of you, whether you like it or not. Time to roll you over and spank your adorably pampered bottom until you wet yourself. Which you actually do! Oh my god, you really do belong in diapers!
Let’s see how long it takes for your soaked diaper to get as cold as this pizza you brought me. I make you sit in your own piss and watch me slowly eat a slice. But how rude of me! I bet you want a bite, too and you can have it, after I make your cock spurt special sauce all over it! I’ll bet the cum is warmer than the pizza. Now you’d better hustle to your next customer, little diaper boy. God only knows what SHE’LL do to you.
diaper discipline, diaper fetish, femdom pov, humiliation, cum on tits
Download link ----> Diapering the Pizza Boy - April 01, 2022 - 2.87 GB
Watch the full clip in my store! XO
diaper, diaper fetish, duel masturbation, lotion/oil fetish, adult babies
Download link ----> Free Diaper Sex in Front of the Fire - December 22, 2020 - 174.86 MB
What’s that bulge in your diaper, sweetie? Is that morning wood or are you just excited to be diapered? I’m always teasing you with my big, soft breasts. Nothing makes your little thingie hard like my boobies and I love titty fucking you in your diaper, even before I’ve cleaned you up, getting your pee all over and making a huge mess. But…what if we make a deal? You lick Mommy’s tits clean and I’ll lick your pee pee all clean in return. Sound good, cuddle bear? I mean, who wouldn’t want to wake up to a diapered blowjob—even if Mommy doesn’t let you cum like a big boy? Perhaps if you’re a good boy and play by Mommy’s rules I’ll let you hump your diaper until you do cum. I really shouldn’t let you, but you’re just so cute!
Big tits, orgasms, blowjobs, and DIAPERS! Mommy Dom Penny Barber is going to take such good care of your little thingie and give you a sexxxy diapering.
sph, diaper, diaper discipline, diaper fetish, femdom pov
Download link ----> Diapered Morning Wood and Mommy's Tits - February 01, 2021 - 4.45 GB
Your dad wasn't able to come on our vacation, but I'm glad that you were able to change your plans and come with me. You're such a good son! We're rinsing off after a trip to the pool at the outdoor shower when I start to tease you, flashing my big, tanned breasts and giggling when you blush. You're just so cute! But if a glimpse of Mommy's tits is going to make you blush, I wonder what you would do if I took off my tiny little bikini entirely, got down on my knees, pulled your big, hard erection out of your swim shorts, and started sucking it. Admit it: you love my MILFy body and you're thrilled that your father isn't here so that you can enjoy everything he's missing
milf, cougar, outdoor public blowjobs, taboo, micro bikini
Download link ----> Outdoor Blowjob from Mom - July 29, 2018 - 1.48 GB
Ella Nova is very excited to meet with her new modeling agent for some test photos but there is a lot about the agency run by Penny Barber that Ella does not know. Her first clue that something is not quite right is the schoolgirl outfit with a micro skirt that Penny makes her change into for the first round of photos. When Penny tells her that the next round of photos will be taken with Ella in a diaper, she decides this is not the job for her. Penny has a lot of experience spanking reluctant models into submission, though.
Once her white round bottom has been smacked into a nice glowing shade of pink, Ella goes from demanding her dignity back to promising to be a good girl for "Mommy". As the outfits and accessories get more babyish and humiliating. Ella has to decide just how much embarrassment she is willing to take to avoid another punishment.
diaper discipline, diaper fetish, humiliation, spanking f/f, taboo
Download link ----> Diapered Photo Shoot with Ella Nova - March 13, 2020 - 721.74 MB
Follow me on Twitter @pamperedpenny XOX
milf, eye glasses, nerdy girls, behind the scene
Download link ----> Making Cinematic Porn - November 10, 2018 - 1.79 GB
Watch the full clip in my store!
pov, big tits, pov sex, taboo, mommy roleplay
Download link ----> FREE Fuck Me or I Send You to - May 28, 2021 - 144.31 MB
Watch the full clip in my store! XOX Follow me on Twitter.com/PamperedPenny
pov, diaper, diaper fetish, pov sex, taboo
Download link ----> FREE Favor for Mommy - October 26, 2021 - 220.04 MB
I’m so glad you agreed to come to my house! I get so many applications from guys eager to be regressed, but so few ever work up the courage to actually become my adult-bby. Now, take this special formula and, when you wake, you’ll be in a world free of responsibility, but full of embarrassment, discipline, and diapers!
I’m just finishing oiling my tight, pink, latex dress as you open your eyes. Your world has become a pretty, pink nursery. In fact, it looks a little psychedelic. (What was in that regression serum?!) While you were out, I went through your things and found some contraband: a credit card! You don’t need things like this any more, honey pie. I destroy it right in front of you and then take you to get diapered like the sweet little AB you are now.
Your first diaper will be plain and white. I fluff it thoroughly and slide it beneath you. Before we close it, I have a special toy to determine whether you’re a boy or girl: a beautiful glass butt plug with a teddy bear on top. I get it wet in my mouth, then slide it into your tight, little tushy. Your thingie becomes painfully erect as I play with you, but that doesn’t mean you’re a boy. As I tease your rear and tell you about your new life, you get closer and closer to orgasm until you finally release and come all over my latex-covered breasts. This tells me you’re the best of both worlds: an adorable widdle sissy who gets dressed like a girl and punished like a boy!
I close your diaper and dress you in frilliest, pinkest outfit I have. I’m really good at dressing sissies. I can’t wait to parade you before all the other MommyDoms. That’s right, a life free of responsibility is also a life free of choice and I can show you off whenever, however, and to whomever I desire. Now let’s get you tucked in and I’ll read you a very special story that will help solidify your submissive sissy thoughts before you drift off to Dreamland.
Keywords
-Latex
-Oiling latex
-Cum on latex
-Diapering
-Buttplug
-Humiliation
-Teasing
-Dirty talk
-Femdom
-Femme domme
-MommyDom
-Mistress
-Sissification
-POV
Timestamps
02:09:00 Oiling Latex Dress
03:47:00 Financial domination
05:31:10 Diaper chest reveal and teasing
07:12:00 POV diapering
10:59:22 Licking butt plug & POV plug play
16:21:20 Cumming on breasts
17:44:02 POV sissy dress-up
25:11:15 POV sissy bed time story
latex, diaper, diaper discipline, diaper fetish, mommy roleplay
Download link ----> Penny Barber - Chemical Regression - August 18, 2023 - 4.49 GB
You may have entered my life as a creepy prowler, but now you’re Step-Mommy’s sweet little captive diaper boy! You spend your days tied up, tape gagged, and diapered, hoping that I’ll be in a good mood today and not humiliate you too much. It’s been soooo loooong since you came! When I decide to clean your cock with my tongue, it’s another level of torment. Step-Mommy’s loving kisses and warm tongue tease you to the brink and I even employ your soft diaper to tease your super hard, deprived cock. But it’s been a long time since Step-Mommy’s gotten to enjoy you as well. I can’t help but get more and more sexual with your diapering, stripping out of my apron to expose my big, Step-Mommy titties, jiggling my plump ass in your face, and skating your dick head around my dripping pussy lips. But just as I’m about to allow you into my sex and make you feel like you’re more than just a big diaper boy, like you’re a real man again—I find some contraband in your crib! Well, I guess it’s back to the soft, cold embrace of a diaper for your cock, at least until Step-Mommy decides to forgive you for trying to escape. But don’t worry, sweetie: that cold diaper will warm up as soon as you have a nice, humiliating accident.
Tease and denial orgasm control orgasm denial diaper discipline humiliation diapers bondage big tits femdom pov blow job blowjob handjob
Time Stamps:
0:54 Step-Mommy checks your diaper
1:25 Ripping off your tape gag
2:24 Pumpkin juice sippy cup
3:23 Releasing you from bondage
4:29 Diaper change and hand job
5:25 Step-Mommy show you her tits through her mesh bodysuit
7:45 Step-Mommy sucks your cock in your wet diaper
13:15 Hand job through your diaper
14:23 Removing your wet diaper
14:42 Showing you which diaper Step-Mommy chose for you
16:00 Step-Mommy strips out of her skirt and shows you her legs
16:53 Showing you Step-Mommy’s wet pussy
18:21 Step-Mommy fully takes out her big, soft Step-Mommy titties and plays with them
20:15 Teasing your cock by skating your glans around Step-Mommy’s pussy
21:20 Step-Mommy finds your secret toy—looks like your cock is going into diapers instead of into Step-Mommy’s pussy!
femdom, diaper, diaper discipline, diaper fetish, femdom pov
Download link ----> Mommy's Little Monster - October 23, 2021 - 3.21 GB
You’ve accomplished so much, darling, and Mommy is sooo proud of you! I just can’t help but notice you’re lacking in one department … Sex, sweetie. Mommy is disappointed that you’re still a virgin, so I’m taking this matter into my own hands (and mouth, and pussy). I’m going to teach you everything you need to know about pleasuring a woman. I’ll start by giving your handsome dick a teasing hand job. We’re building your stamina, so you aren’t allowed to come, no matter how good it feels or how much you love staring at my big tits. You have to fuck Mommy in her tight, wet pussy first and make me orgasm all over your amazing cock! Oh, honey, you did such a good job that you get to come in my mouth and watch me swallow it. Now, go hydrate and get ready for round two. Mommy’s going to make you a total stud!
pov, milf, cum in mouth, pov sex, taboo
Download link ----> Sex Lessons With Mommy - August 27, 2021 - 4.59 GB
Extended trailer for My Son is a Vampire! The debauchery takes place over three nights, and each night will be released as an individual clip every Tuesday leading up to Halloween.
10/17/2023 First Night: Claiming your mother with your fangs and your huge cock!
10/24/2023 Second Night: Mom sucks your dick, then turns you into her vampiric pussy-eating sex toy.
10/31/2023 Final Night: Taking back control, putting your mommy slave in her place, and your big cock between her punished tits.
If you enjoy my Halloween specials, then check out the trailer for my latest and greatest feature "My Mother's Body" and learn how you can get access to the full video.
(www.manyvids.com/Video/5104313/My-Mothers-Body-Trailer)
bdsm, pov, mind fuck, taboo, vampire
Download link ----> FREE My Son is a Vampire - October 18, 2023 - 125.4 MB
Watch the full clip in my store. XO
pov, games, older woman / younger man ., big ass, games
Download link ----> FREE Rainy Day Fuck Fest with Mom - March 09, 2021 - 134.44 MB
After all that noise last night I’m not surprised to find you out on the lawn. Sounded like quite the rager!
You know, you’re lucky your stepmom and I are such good friends that I promised I’d take care of you while she’s out of town. You’re feeling so hungover that you don’t struggle as I take you inside to clean you up. After all, isn’t it more fun when the busty MILF next door gives you a sponge bath?
It is. After stripping you out of your adorable underwear, I gently clean and admire your massive cock while teasing you with my big, juicy tits. You wish you could do something about it, but you’re still a little hazy.
After a rest, you come to the kitchen to find me tidying up in nothing but a frilly, pink apron. But I’m not the only one dressed kinda weird. I tell you to look down and you’re shocked to see that I’ve diapered you in a thick, embarrassing diaper! I also took the key to your house, so you better be a good boy for me this week! It’s an absolute delight watching you squirm as I take my top off and let you stare at my soft pillowy breasts while I feed you. You’re unable to resist when I demand that you wet your diaper. What can you do other than absolutely flood it? I’m holding all the cards.
You get so embarrassingly hard—and you’re being such a good boy—that I think you’ve earned a reward. I lovingly pleasure you with my soft hands, warm mouth, and huge tits, coaxing your diapered cock to orgasm until you absolutely cover me with your cum. We’re going to have a lot of fun this week, my widdle stud.
milf, diaper, diaper discipline, diaper fetish, femdom pov
Download link ----> Penny Barber - Neighbor Makes You Her Diaper Stud - July 14, 2023 - 4.53 GB
Look who is home from class and so eager to play with Mommy. I know you want to be my sweet little baby but there is one last big boy chore to finish first. No diapers until after your blowjob, that's the rule. Just drop your pants and we can do it right here in the kitchen.
Your cock looks so much cuter in a nice crinkly diaper after it is all soft from being drained by Mommy's mouth. I want you to cum on my face and then I will powder your bottom.
blowjob, milf, diaper fetish, mommy roleplay
Download link ----> Dreaming of Diapers and Blowjobs - March 27, 2020 - 824.42 MB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
pov, diaper, diaper fetish, vibrator, cheating wife
Download link ----> FREE Cheating Diapered Housewife - September 23, 2022 - 90.77 MB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
diaper, diaper discipline, diaper fetish, pegging, real doll
Download link ----> FREE - You're My Diaper Fetish Doll - June 09, 2023 - 150.03 MB
Someone has been such a naughty ABDL prince lately that the Queen herself has asked me, your fairy godmother, to magic some sense into that spoiled mind of yours. With a wave of my hand I conjure a beautiful bottle of the sweetest nectar for you to indulge while we speak of your behavior. It doesn’t take long for the room to spin as my magic takes hold and transforms you from a naughty little prince into a pretty little princess.
As I change your diaper I find the last widdle stiffy you’ll ever have. Let your fairy godmother show you how to masturbate with a pillow like a proper princess. I grind and pleasure myself on a pink silk cushion as you watch and learn to do the same. We climax together as my magic takes a deeper hold on you, removing any last resistance you may have. As I change you into your new pink diaper and onesie, the changes become permanent. The Queen will henceforth have the obedient well behaved princess she has always deserved.
diaper, diaper discipline, diaper fetish, adult babies, sissification
Download link ----> Diaper Fairy Sissy Potion - October 28, 2022 - 3.73 GB
Shy and squirming on your front porch, I admit that two glasses of champagne may have been a little much, but that I had a wonderful time on our date anyway. You had a good time, too—despite being able to smell my wet diaper the whole time! I’m incredibly embarrassed, but eventually admit that, yes, my butt has gotten a little puffier over the course of the evening as my diaper swells with accident after accident. But rather than discuss this outside, could I maybe come in?
I squirm around on your bed, showing off my full diaper (a Dry 24/7) from all angles. You have one condition for agreeing to change me, though: I have to suck your cock! I can’t believe that you’d want a blowjob from a girl in a diaper, but I eagerly agree and take you in my mouth, all the while begging you to change me. Once I’m freshly diapered, we just sort of pass out in your bed, but you’re still all hot and bothered. After all, I’ve definitely peed again. When I finally wake up it’s to a shaking bed—and your hot cum splattering all over my warm tits!
Timestamps:
4:05 Showing off my diaper
10:21 Diapered blowjob
18:21 Diaper change
26:44 Cumming on my breasts
diaper, diaper discipline, diaper fetish, embarrassment, pov blowjob
Download link ----> Come In and Change My Diaper - February 10, 2021 - 4.03 GB
I thought that you had enough when I told you to jerk off in the kitchen, but apparently you?re insatiable for Mommy?s curvy body. But I?m not mad when I catch you peeking on me in the bathroom, watching me wash my massive tits with what almost seems to be too much slippery soap. In fact, I think it would be kinda fun to give you a little sex show. Did you know that Mommy had so many fun bath toys? Or that they fit so deeply into my hungry pussy and ass?
pov, milf, anal masturbation, wet & messy, mommy roleplay
Download link ----> Bathtub Sex Show with Mom - September 29, 2020 - 1.76 GB
Is everyone ready to begin this meeting of the Anime Club? Ok I know it is just you and I here but we should still act like a real club. Yes, I did watch that weird Omutsu video you sent me but the whole diapers and mind control thing was too much for me. It also kept having this strange glitch and… ACHOO!
Excuse me, anyway, what was I saying? Oh right, I was flashing you peeks of my panties under my skirt. These panties are pretty boring though. I wish I had something kinky like a diaper to tease you with during all our Anime Club meetings. You have a fetish style adult diaper and a slutty anime gym costume with you right now? Weird coincidence but I definitely want to try on both. Judging by that stiffy in your pants, I’m not the only one getting super turned on by this skimpy outfit and my diaper.
exhibitionism, cosplay, diaper fetish, magic control, transformation fantasies
Download link ----> Anime Nerd Transformed Into Diaper Slut - May 10, 2019 - 882.91 MB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
milf, diaper, diaper fetish, humiliation, pov sex
Download link ----> FREE Best Sleepover EVER - April 28, 2023 - 101.21 MB
Just a sneak peek at some of Mommy Penny Barber's favorite fetishes. Video by Victor Von. XO
femdom, diaper, diaper discipline, diaper fetish, sissification
Download link ----> FREE Penny Barber ABDL Fetish Sex Clip - January 10, 2021 - 386.96 MB
I am so excited to see what you picked out to play for Mommy-son game night. What do you mean you have a date? Why would you want to hang out with some girl on our special night? I think you need a reminder who you belong to and I bet that little slut friend of yours needs to get the message as well. Give me your shirt, Mr. Too-good-for-game-night-with-Mom.
You sit right there and watch as I take off all my clothes and use your shirt as cover for this pillow I’m going to rub off on. You think about what you did as you stare at my big soft tits while I soak your shirt in pussy juice. I want your date to smell it as soon as she walks in the door. Good luck getting the image of my naked body humping your t-shirt to multiple orgasms out of your head when all you will be able to smell on your entire date will be Mom cum.
milf, embarrassment, masturbation games, taboo, mommy roleplay
Download link ----> Covered In Mom Cum Before Your Date - July 07, 2019 - 260.29 MB
Watch the full clip in my store! XO
diaper, diaper fetish, jeans/pants wetting, pee, pov blowjob
Download link ----> FREE Come In and Change My Diaper - February 10, 2021 - 180.56 MB
At a dinner party, I manage to get you alone in the kitchen. I'm so fed up with my loser husband. I bet you could just lean me over this counter and fuck me to hell and he wouldn't even do anything. After you enjoy my pussy, I jerk you off into my glass so that I can sip your semen in front of everyone.
pov, milf, pov sex, cheating wife, cheating
Download link ----> Let's Cuck My Husband - April 29, 2021 - 1.73 GB
I told you that you would have to be quiet if I brought you to work with me. If you can't understand that I need silence when I am on the phone then I will put it in terms any boy your age would understand. Sealed lips means you get to see Step-Mom's tits. I will take off my bra and stroke that nice fat cock of yours while you drool over my big, soft breasts. After that I don't want to hear another sound out of you, except maybe a little moan when I make you cum.
handjobs, milf, taboo, mommy roleplay
Download link ----> Step-Mom Jerks You Off to Shut You Up - May 17, 2020 - 607.15 MB
Watch the full clip in my store! XOX Follow me on Twitter.com/PamperedPenny
pov, garter & stockings, pov sex, taboo, pov blowjob
Download link ----> FREE Mommy Knows Best - September 23, 2021 - 193.61 MB
Your sister and I are so sorry that your big date turned out to be a prank, sweetie. I guess you will just have to stay in with us tonight and we will do our best to make you feel better. Looks like you were expecting to get laid tonight because we can definitely see the little tent in your pants still. Or is that from Mom and sister wearing lingerie around you?
It might be for the best that the mean girl did not go out with you since I can't imagine she would be very kind to boy with such a small package. We can't even ask one of Ella's friends to take you on a pity date with a dick like that. Think how embarrassing that would be for your sister if everyone at school knew her brother has a tiny penis. I think the best your little cock can hope for is some playtime with Mom and sister because we feel sorry for you.
handjobs, sph, sisters, taboo, mommy roleplay
Download link ----> Mom And Ella Nova Tease Your Tiny Dick - July 14, 2019 - 372.41 MB
You’ve been selected for a medical device trial! Sure, it comes with a few risks—you didn’t know so many waivers existed—but, hey, it pays well and you’ll be contributing to society, right? After watching the intake video, you sit down with the head scientist, Dr. Penny Barber. Is…is she flirting with you? She is kinda hot with those glasses and 34DD tits, her perky nipples at full attention under the thin fabric of her dress. You’re so distracted by her boobs that, before you know it, she’s started the experiment!
The next thing you know, you’re in a strange room with Dr. Barber hovering over you, wearing nothing but lingerie and a satin apron. She seems to know all about your most private fantasies, things you’ve never told anyone, like how you get a raging erection over diapers and being treated like a b@by. Like magic, she starts diapering you, sucking your cock, and fulfilling every kinky fantasy you’ve ever had, lifting her apron to show off her pussy, helping you wet your diaper, and even fucking you. Dr. Barber rides you in your twice wet diaper, her orgasming sex squeezing your hard on until you cum deep inside her warm, wet pussy.
Suddenly you’re back in the testing facility, face-to-face with the real Dr. Barber. She saw the whole thing—and now she has some questions.
pov, diaper, diaper discipline, diaper fetish, pov sex
Download link ----> The BBY Device - March 04, 2022 - 4.38 GB
I half thought your wife was joking when she hired me to watch you while she went out to fuck another man. But here you are, sitting all by your lonesome on that big bed. You barely put up any resistance as I diaper and dress you, which is good because your wife was very specific in her instructions. Not only are you to be diapered up like the tiny-dicked ABDL that you are, but you’re to have a very special bedtime story. I’m going to tell you every single depraved thing your sweet little wife is doing, and, to make it even better, you’re going to act it all out with this rather large strap-on, including taking every last inch up your tight, virginal ass! You can try to resist, but what’s the point, cuckie? Just lie back, let me open up your diaper, and spread those legs for your babysitter!
SPH diaper discipline cuckysitter cuckold withal cheating hot wife big tits strapon pegging femdom POV Penny Barber
strap-on, diaper, diaper discipline, diaper fetish, humiliation
Download link ----> Babysitter Fucks the Diaper Cuck - January 21, 2022 - 3.11 GB
Watch the whole thing at https://www.manyvids.com/Video/2291773/finally-fucking-mom/
pov, milf, pov sex, taboo, mommy roleplay
Download link ----> Finally Fucking Mom Extended Trailer - October 16, 2020 - 148.97 MB
My plan is to stay home reading a book alone on Halloween but my cool older brother surprises me with a costume and an invitation to a party! I am a little nervous but he convinces me to try on the slutty school girl uniform and even to wear it with no panties on under the tiny skirt.
Once I am dressed up to go out big brother tells me that he just needs to check one last thing under my skirt before we leave. I guess I don't know much about parties because I am not sure why he needed to check both my holes... with his tongue!
role play, face sitting, school uniform, sisters, taboo
Download link ----> Tricking Nerdy Sister Into Face Sitting - December 09, 2018 - 978.62 MB
I don't know if this was meant as a weird joke or what but I have no idea how to react when Mom opens her present from you to see an odd chair with a huge dildo attached. Who ever even heard of a fucking machine? Mom is less shocked than I am and seems to think a sex toy from her son is just harmless fun. It's so big that it is more a sexual appliance than a sex toy anyway.
Then the real shock comes when Mom agrees to lift up her skirt and let the machine fuck her right there in the living room. Then she cums so hard that she actually convinces me to try it too! I can't believe I owe my best holiday orgasm ever to my brother.
milf, fucking machines, sisters, taboo, mommy roleplay
Download link ----> Gifting Mom A Fucking Machine - December 15, 2019 - 787.2 MB
Oh sweetie, thank goodness you’re home! Mommy’s date took a weird turn and I really need your help. Please get Mommy out of these uncomfortable and humiliating restraints and don’t pay attention to the…fucking machine. Why are you picking up the controller? Don’t you dare turn it on! Oh my god! What’s it going to take for you to stop?!
You slowly turn up the intensity as I promise you more and more filthy things if you make it stop. After offering to let you play with my tits, my mouth, and my pussy, you finally let me know that you will only stop if Mommy promises to be your sex slave! I relent after you use the fucking machine to bring me to a screaming orgasm. Then you put a leash on my collar and make me suck your big cock until you cum in your Mommy slave’s obedient mouth. Thanks for the help, darling!
toys, female training, fucking machines, submissive sluts, mommy roleplay
Download link ----> Fucking Machine Makes Mommy Your Sex Toy - July 16, 2021 - 2.46 GB
Poor little Mia looks so confused when she finds herself all tied up and naked except for a pretty pink diaper on her bottom. I have decided that she will make an adorable adult baby girl and Mia has absolutely no say in the matter, not that I can understand her through the pacifier gag filling her mouth!
I play with her cute bare boobs and rub her diapered butt while I explain that she is just a little baby now. Mia is a very fussy little diaper girl at first so I pop out her pacifier and slip a nipple between her lips. Mia will have a very hard time convincing anyone she is a big girl while in her pink diapers with a mouth full of Mommy’s breasts!
bondage, breast smothering, diaper discipline, diaper fetish, lesbian domination
Download link ----> Captive Diaper Girl Mia Little Breastfed - December 14, 2018 - 1.82 GB
Hi, Daddy. Watch me try on lots of ABDL diapers and outfits, trying to decide what I'm going to wear for a private party in San Francisco this Halloween. Should I go for more slutty? Cute? Should I wear a diaper with two tapes or only one? If my bib doesn't cover my nipples, I'll need to wear pasties. Is my all-plastic adultbaby dress too see-through? I get excited trying on all of my ABDL fetish wear, so I put my favorite butt plug in and wet my diaper. There's nothing like the feeling of wetting with an anal plug in! XOX
diaper, diaper fetish, taboo
Download link ----> Pick Penny's ABDL Halloween Costume - October 06, 2017 - 1.72 GB
Watch the full clip in my store! XOX Follow me on Twitter.com/PamperedPenny
milf, food masturbation, pov sex, taboo, caught
Download link ----> FREE Putting the Groceries Away HARD - November 25, 2021 - 210.28 MB
Today’s couples therapy session is going to be a little different. For one, your wife is going to be in the next room. Getting fucked. By a real man with a huge dick who can actually satisfy her. You, on the other hand, will be in here with me, your therapist, getting plugged, diapered, and locked in chastity, as befits your tiny cock. However, just because you’re soooo pathetic, I guess I’ll give you a pity hand job. Then it’s right back into the chastity device—until your wife can buy you a smaller one anyway! Just lie back and listen to her getting reamed while I stroke your little thingie for all of a minute and a half before your neglected little penis pops its tiny load into your diaper. Then you can waddle next door and knock to let your wife know that your time for the week is up and it’s time to leave her therapy stud. Speaking of which, I wouldn’t be surprised if she wanted to start coming in a lot more often!
cuckolding, diaper, diaper discipline, diaper fetish, humiliation
Download link ----> Diaper Cuckold Therapy - June 04, 2021 - 2.91 GB
When I catch you messing around with your little girlfriend, I know that extreme measures are in order. First of all, yes, I will admit that I'm a little jealous. I like being the only woman in your life! However, I also know that you're grown now and have needs. How can I get that little slut to stop putting her hands down your pants while still giving you the satisfaction that you need. Maybe a little diaper discipline? After all, Mommy doesn't mind at all if you're in a diaper, but I bet your girlfriend will! I put you in a thick disposable diaper and start stroking your cock. Is this why you like her so much? You're so overwhelmed by how unexpectedly erotic the experience is that you cum all over yourself when I'm not even touching you. Oops
diaper, diaper discipline, diaper fetish, taboo
Download link ----> Mommy Diapers and Drains Your Cock - July 06, 2018 - 1.82 GB
I am just putting together some final details for your upcoming business trip and I wanted to show you the diaper changing schedule that your wife approved. Of course you will be need to be diapered at the conference, why would you think your wife would let you have big boy underwear just because you are going out of town. That is just silly.
Now there is one thing your wife forgot to consider about your cloth diapers and that is the pins could be troublesome going through airport security. If you just lie down, I will get it switched for a nice puffy disposable diaper with tapes. Your wife has mentioned that you have the self-control of a baby in more ways than one but I hope we can avoid any little accidents while I change your diaper in the office.
diaper discipline, imposed ejaculations, office domination
Download link ----> Secretary Becomes Your Babysitter - September 13, 2019 - 617.34 MB
A Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
lace/lingerie, joi, cock tease, taboo, story telling
Download link ----> FREE - Naughty JOI Stories from Mommy - April 16, 2023 - 90.86 MB
Coming soon! Lots of oral sex, rimming, cunnilingus, latex, panty worship, pegging, wedgies, humiliation, and revenge! XOX
latex, strap-on, femdom sex, pegging, mommy roleplay
Download link ----> Mommy Butt Fucks Your Bully Trailer - November 13, 2020 - 148.97 MB
Full video coming soon! Follow me here or on Twitter.com/pamperedpenny for updates. XXX
futa, futanari, silly sluts, sissy training, sissification
Download link ----> May Cause Ditziness Trailer - December 10, 2020 - 191.73 MB
If you really did finish all your chores then you will get your reward but I would hate to have to punish you if something got missed. If you are sure that everything is all done then I guess you earned an orgasm. Come here so you can stare at my big, full breasts while I stroke your cock.
I might as well strip all the way naked for your handjob. I always say if something is worth doing, it's worth doing right. Do you think if I let you stare at my ass and slide your cock between my tits that we can get all the cum out of you? You worked hard on your chores so Step-Mom is going to work just as hard on your hard-on.
milf, big tits, taboo, mommy roleplay, cum on tits
Download link ----> Mom Drains Your Cock After Chores - June 07, 2020 - 607.78 MB
You’ve been adjusting so well to live as my diapered little girl! But now that I’ve diapered and subjugated your cute little cock, I need to train it to perform: to come in diapers, to get stiff when you sniff my panties, to squirt on command—to amuse and enchant not only me, but any Mistress friend of mine who might want a little show!
diaper, diaper discipline, diaper fetish, sissy training, sissification
Download link ----> Mistress Trains Her Diaper Girl's Cock - November 28, 2020 - 1.76 GB
The full video is available in my store at https://www.manyvids.com/Video/2256997/mom-jerks-you-off-after-you-punch-a-wall/ XO
handjobs, milf, assisted masturbation, masturbation encouragement, mommy roleplay
Download link ----> Mom Jerks You After You Punch a Wall Tra - November 02, 2020 - 148.16 MB
I know you want to play my game but what is in it for me? You can have a turn...if you wear nothing but a pair of my panties the whole time you play! You can wear the ones I have on right now. I will be naked and you will be pantied but I think only one of us is gonna be embarrassed.
femdom pov, feminization, humiliation, sissy training, taboo
Download link ----> Sissy Video Games With Sis - February 10, 2016 - 609.65 MB
I’m getting dressed when you walk in on me. (Don’t you know how to knock?!) You can’t believe how tight my jeans are and aren’t sure that your Mom should be wearing something so slutty. They’re just painted on. You decide to make a bet with me: if you can see a butt plug through the jeans, I have to suck your dick. If not, you have to clean the kitchen for a month! I’m feeling a little flirty and flattered that my own son apparently thinks I’m so sexy, so, after a little hemming and hawing, I agree. You watch me slide down my tight mom jeans and stick the plug up my ass. Of course, I can’t really see, so I’m just going to have to trust you when you say that it’s totally visible! And since I’m already sucking your cock, why not fuck me in the ass as well? After all, what’s one more secret from Dad?
Timestamps:
0:04 Walk in on Mommy getting dressed
1:43 You proposition me
4:42 Stripping
5:32 Inserting the butt plug
9:28 Ball worship
10:53 Blowjob / handjob combo
11:50 Tits out
14:05 Titty fucking
16:09 Reverse cowgirl dry humping
18:15 Anal fingering
19:07 Butt sex
26:01 Anal cream pie
anal, milf, pov sex, butts, mommy roleplay
Download link ----> Mom Jeans POV Anal Sex - January 24, 2021 - 3.77 GB
Even dirty girls have to get clean sometimes but soaping up and scrubbing down my bare skin is always more fun with an audience. Which is why I invite you to come watch me strip to my pretty pink diaper for some pre-shower play time. My diaper is still dry so I guess I will just have to wet myself right in front of you before I can take it off. Once I am all warm and squishy in my diaper though I decide that I would rather see just how wet I can get instead of getting all the way naked.
I have fun teasing you by soaping up my big, round breasts and wiggling my completely soaked diaper butt in your face. The squishy warm feeling between legs is even nicer than the feeling of giving my pervy brother a boner though. I get so excited playing around during my little diapered shower cock tease that I just have to make you watch me do one last naughty thing in my diaper to make it even wetter.
masturbation, shower, diaper fetish, sisters, taboo
Download link ----> Diapered Shower Show From Your Sister - March 15, 2019 - 711.46 MB
[spoiler=Cucking Your Father | Penny Barber - January 07, 2022 / 4.62 GB]
Please don’t run away! I’m sorry your father won’t let you have a girlfriend, honey, but you can’t leave me here with him. Mommy loves you and will do anything to get you to stay. I notice you get hard as I beg you not to leave, so I slowly expose my big soft tits. My nipples stiffen with excitement as you let me take your thick beautiful cock out of your pants and stroke it and suck it. It has been so long since your father satisfied me that I pant like a desperate slut as you fuck my tits. Please stick that perfect cock in Mommy’s hungry pussy! This is what we both need. You make me come over and over as we fuck in three different positions and I tell you how much better you are than your father and how much that asshole deserves to be cucked by his superior son. You give Mommy a nice wet cream pie before I masturbate to one more in front of you with your cum dripping out of my deeply satisfied pussy.
I’ll tell your father that we’ve resolved this issue but that he shouldn’t rush to get home, stud.
pov, milf, cuckolding, taboo, drama
Download link ----> Cucking Your Father | Penny Barber - January 07, 2022 - 4.62 GB[/spoiler]
