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
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Diaper Change Chastity Tease - June 02, 2017 - 1.75 GBA 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
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FREE You Belong in Diapers - December 09, 2021 - 222.45 MBI 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
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Tiny Diapers for Your Tiny Cock - June 19, 2020 - 547.85 MBI 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
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Stripper ABDL Babysitter - February 27, 2017 - 1.72 GBMom 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
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Sweet JOI With Mom's Breasts - April 22, 2019 - 716.55 MBWatch the full clip in my store. XOX
feet, milf, barefoot, pov sex, mommy roleplay
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FREE Before You Go to College - March 05, 2021 - 144.74 MBI 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
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Mom Gives You Sexual Rewards - January 12, 2020 - 604.3 MBYou’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
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Rx: Diaper, Enema, Blowjob - October 18, 2020 - 1.76 GBIt 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
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BatMommy Takes Your Costumed Cock - October 20, 2021 - 3.31 GBSmells 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
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Wanking In The Woods With Mom - July 21, 2019 - 541.54 MBWhy 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
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Cuckysitter Loves Teasing Diaper Boy - June 21, 2019 - 464.9 MBYour 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
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Mommy's Getting Divorced - May 24, 2021 - 4.49 GBThis 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
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Mommy's Sweet Rewards - January 28, 2022 - 4.52 GBI 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
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Spankings & Diapers For Sneaky Step-Son - December 07, 2018 - 924.21 MBSeems 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
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Mommy Gets Stuck and Fucked - January 29, 2021 - 3.02 GBI 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
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Begging Daddy for a Diaper Change - January 31, 2020 - 638.99 MBGood 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
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Secretary Loves Playing Mommy for You - December 27, 2019 - 634.16 MBI 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
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Mommy Cleans You Up And Sucks You Off - January 27, 2019 - 1.76 GBI 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
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Becoming Batgirl to Fuck Batman - January 05, 2020 - 657.68 MBOh, 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
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Earning Your Allowance - January 14, 2022 - 4.61 GBGood 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
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Very Inappropriate Breakfast With Mommy - July 28, 2021 - 2.85 GBWatch the full clip in my store! XOX Follow me on Twitter.com/PamperedPenny
pov, milf, big tits, taboo, caught
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FREE Mommy Catches You, and Helps - December 02, 2021 - 224.46 MBIt’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
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Aunt's Sexy Summer Footjob - September 16, 2022 - 4.23 GBI 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
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Step-Mommy Diapers Herself and then You - September 04, 2020 - 561.03 MBI 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
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Mom Motivates You with Blowjobs - November 24, 2019 - 684.33 MBOkay, 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
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Sick Mother Fucker - May 13, 2022 - 4.43 GBAnother 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
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Making Mom His Reluctant Fucktoy - December 23, 2018 - 997.69 MBI 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
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Diapered After Sex - February 18, 2022 - 4.58 GBWe 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
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Bedwetter Teased By Busty MILFs - October 11, 2019 - 678.54 MBI 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
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Dick Pics With Mom - June 09, 2019 - 605.23 MBYou 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
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Kinky Sex with Goth Mom - May 30, 2020 - 464.6 MBI 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
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Mom Plays Dress Up To Get Your Grades Up - August 04, 2019 - 550.35 MBGood 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
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Collared Mommy Sex Slave - August 12, 2021 - 3.13 GBThe 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
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Mom's Cum Slave - June 10, 2018 - 1.82 GBI 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
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Mommie's Cock Tax - April 04, 2016 - 597.53 MBYou’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
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Penny Barber - Mom Catches You Stealing - March 24, 2023 - 3.79 GBMommy 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
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Mommy Knows Best - September 24, 2021 - 4.54 GBWhen 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
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Penny's Diapered Road Trip with Daddy - June 25, 2021 - 3.21 GBAre 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
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Sissy Panty Sniffer - January 21, 2016 - 776.15 MBMy 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
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Mommie Diapers Stepdaughter in front of - February 14, 2017 - 1.73 GBA 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
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FREE Coming in Mommy's Pussy - August 19, 2022 - 95.16 MBYour 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
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French Mom Squirts as You Stroke - December 02, 2020 - 2.51 GBLook, 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
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Fucking a PS5 Out of Mommy - January 05, 2021 - 4.17 GBHave 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
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May Cause Ditziness - December 13, 2020 - 4.53 GBSweetie, 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
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Mesmerized Into Diapers - November 19, 2021 - 4.61 GBFind the full clip in my store! XO
pov, femdom, diaper, diaper discipline, diaper fetish
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FREE Bonding With Mommy - July 08, 2021 - 154.79 MBI 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
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Wanking in the Woods to Step-Mom - August 30, 2020 - 374.39 MBThis 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
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Valentines' Day Diaper Punishment - February 13, 2021 - 4.57 GBWatch the full clip in my store. XO
pov, milf, pov sex, taboo, pov blowjob
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FREE Spying on Auntie - May 06, 2021 - 180.99 MBFollow me on Twitter @pamperedpenny
Follow me on Instagram @pampered_penny
Order a custom video
[email protected]XOXO
femdom, femdom pov, behind the scene
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Get Your Wife into Femdom - September 10, 2017 - 1.75 GBA 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
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FREE Earning Mommy's Collar - August 04, 2022 - 179.89 MBI 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
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MILF Sex Trance Ends In Spanking - April 28, 2019 - 654.57 MBI 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
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Diaper Fetish Exposed On First Date - March 29, 2019 - 762.84 MBLook 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
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Mommy Fucks You in Her School Uniform - July 05, 2021 - 3.93 GBWhen 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
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Mom Is Your Cock-Sucking Secretary - November 22, 2018 - 1.82 GBknow 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
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Bedwetter Diapered By His Crush - February 22, 2019 - 844.13 MBDid 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
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Diaper Sex - August 05, 2021 - 3.65 GBYou 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
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Creaming Your Diaper in the Car - September 25, 2020 - 539.43 MBWere 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
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Diapers are for Cum - February 28, 2017 - 1.74 GBI'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
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Therapist & Wife Sissify and Diaper You - June 22, 2018 - 1.82 GBThis 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
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Diapered for Your Big Date - June 11, 2018 - 1.84 GBI 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
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Strip Board Games with Step-Mom - April 26, 2020 - 720.58 MBA 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
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FREE Pegged & Pampered - August 26, 2022 - 201.39 MBNone 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
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Mom Flashes & Fucks You Outside - September 02, 2022 - 4.45 GBElla 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
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Sissy Baby Cheater with Ella Nova - June 25, 2020 - 581.94 MBtimer 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
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Diaper Challenge for PrematureEjaculator - February 28, 2020 - 661.79 MBI 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
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First Date Diaper Change - March 06, 2020 - 460.02 MBAfter 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
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Mommy Knows You Fuck Your Sister - March 01, 2021 - 3.6 GBI got stood up yesterday, but I still had a pretty amazing time
milf, yoga pants, adult babies
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Stood Up, but Still Fucked & Spoiled - February 06, 2017 - 1.74 GBNow 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
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Ella Nova Is Your New Sissy Sitter - June 14, 2019 - 795.89 MBI 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
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Breasts Compel You to Wear Diapers - February 28, 2017 - 1.73 GBA 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
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FREE Diaper Hookup - August 15, 2022 - 98.28 MBWould 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
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Rubber Pussy Handjob from Mommie - February 05, 2017 - 372.2 MBYour 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
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Efficiency Exert Diapers You - October 05, 2018 - 1.82 GBPeople 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
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Prim Sister Admits Her Lust - March 11, 2018 - 1.77 GBA 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
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FREE Mommy's Sex Addiction - February 24, 2023 - 88.46 MBI 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
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Bambi Belle's Regression Punishment - July 12, 2019 - 538.15 MBYour 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
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Slutty Mommy Study Buddy - April 08, 2022 - 4.23 GBWhile 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
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Slut Sister Strips for $100 - July 16, 2017 - 1.75 GBWe’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
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Grounded by Mom's Futa Cock - October 01, 2017 - 1.74 GBI 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
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Wife's Ultimatum - April 05, 2019 - 659.13 MBNo 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
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Solo Diapered Spank and Fuck - April 10, 2020 - 771.23 MBOwen 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
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Appreciating My Panties - January 26, 2015 - 839.26 MBA 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
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FREE Babysitter Fucks the Diapered Cuck - August 24, 2022 - 173.59 MBReady 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
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FREE - JOI to Mom's Yoga Body - July 28, 2023 - 183.22 MBI’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
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Diaper Date Cream Pie - July 24, 2021 - 4.59 GBDo 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
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Diaper Cheerleader's Teasing JOI - February 08, 2019 - 1.94 GBI 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
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Scientist Regressed into Diaper Brat - June 05, 2020 - 518.71 MBFollow me on Twitter @pamperedpenny
Follow me on Instagram @pampered_penny
XOXOX
latex, mistress, female domination, glove fetish, behind the scene
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Uncollaring My Submissive - October 15, 2017 - 1.74 GBIf 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
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Family Fuck Night with Lola Fae - April 19, 2020 - 709.64 MBA 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
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FREE Melting Mommy's Mind - August 12, 2022 - 121.24 MBBambi 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
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Bedwetter's Diaper Sex Reward With Bambi - January 04, 2019 - 1.47 GBNaI 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
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Girlfriend Encourages Your Diaper Fetish - May 26, 2020 - 945.14 MBI’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
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Very Inappropriate Ride Home With Mommy - July 30, 2021 - 2.96 GBYour 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
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Fucking Step-Mom in Your New Room - September 07, 2020 - 565.51 MBHow 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
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Supernatural Futa Mom Needs To Cum - June 23, 2019 - 735.79 MBA 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
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FREE - Watching Porn With Mommy - August 04, 2023 - 153.56 MBA 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
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FREE Scent of a Mommy - August 03, 2022 - 94.41 MBYou 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
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Mom's Tits Are Your Halloween Treat - October 20, 2019 - 634.23 MBI 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
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Chastity Devices & Dick Pills from Mom - February 09, 2020 - 642.26 MBI 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
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Mother-in-Law Sex Initiation - June 14, 2020 - 722.25 MBA 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
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FREE Wifey Discovers ABDL Search History - September 05, 2022 - 227.71 MBIn 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
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Lois Griffin Diapers Peter and Herself - August 07, 2020 - 516.83 MBIt 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
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Covered In Panties - February 09, 2016 - 1.24 GBIt 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
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Mommy's Punishment for Diaper Boy - January 24, 2020 - 628.24 MBWhat 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
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Mommy's Your GF for Christmas - December 17, 2021 - 3.29 GBI 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
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Pee Freak Caught Spying on Step-Mom - September 20, 2020 - 1.28 GBWatch the full clip in my store!
diaper, diaper discipline, diaper fetish, femdom pov
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FREE Conditioning You to Love Diapers - May 10, 2021 - 157.76 MBI 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
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Strict Discipline for a Boring Husband - May 25, 2017 - 1.75 GBCan 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
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Mom Takes Care Of Your Over Wanked Cock - December 08, 2019 - 684.72 MBAfter 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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Diapered by Your Crush - July 10, 2021 - 4.52 GBI 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
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Penny Barber - Sugar Cookies - January 01, 2023 - 3.93 GBYou 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
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Rival Coworker Diaper Punishment - August 20, 2021 - 3.87 GBEven 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!
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Finally Fucking Mom - October 16, 2020 - 1.82 GBI 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.
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Therapist Makes You Her Diapered Sex Toy - April 24, 2020 - 709.26 MBWatch the full ABDL clip TOMORROW in my ManyVids store! XO
diaper, diaper discipline, diaper fetish, taboo, nurse
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Rx: Mommy Domme Extended Trailer - October 23, 2020 - 152.24 MBI 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
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Diaper Slut Is Desperate For Your Cock - October 04, 2019 - 737.55 MBOur 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
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Family Vacation Masturbation Frustration - September 10, 2021 - 4.62 GBWhat 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
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Mom Convinces You to Stay - March 25, 2022 - 3.98 GBA Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
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FREE Controlling Top Pantyhose - June 23, 2023 - 239.73 MBBarely 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?
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Mommy Catches You & Helps You Finish - December 03, 2021 - 1.34 GBThis 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
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Diapers or Chastity: You Have to Choose - March 20, 2017 - 1.75 GBThat 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!
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Mommy Butt Fucks Your Bully - November 15, 2020 - 4.61 GBWatch the full clip in my store! XOX
Follow me on Twitter.com/pamperedpenny
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FREE Fucking Machine Makes Mommy Your - July 17, 2021 - 156.03 MBThere 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
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Messy Punishment for Stubborn Sissy - September 27, 2019 - 803.52 MBI 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.
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Diaper Bimbo Wants A Pet Sissy - August 02, 2019 - 841.21 MBI 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
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Obsessed With Mom's Jean Covered Ass - March 17, 2019 - 724.5 MBI 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!
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Mom Shows Off Her Tits On New Year's Eve - February 17, 2019 - 763.33 MBWatch the full clip in my store! XOX Follow me on Twitter.com/pamperedpenny
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FREE Collared Mommy Sex Slave - August 11, 2021 - 150.99 MBI 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.
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Diaper Punishment at School - May 26, 2019 - 777.58 MBA Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
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FREE Sunday Morning Wood - January 27, 2023 - 80.12 MBA Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
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FREE Diaper Bet With Mom - February 10, 2023 - 107.14 MBSubmitting 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.
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Mistress Decides You Should be Her Baby - November 15, 2019 - 593.75 MBWatch the full clip in my store! XOX Follow me on Twitter.com/PamperedPenny
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FREE Mommy Can't Find Her Glasses - November 05, 2021 - 209.11 MBItʼs 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.
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Family Movie Night - October 08, 2020 - 1.8 GBI'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
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Diaper Girl POV Suck and Fuck - July 27, 2018 - 1.82 GBWhy 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
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MILF Drips - April 02, 2022 - 3.09 GBWatch the full video in my store! XO
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FREE Mommy Makes You Miss the Bus - June 14, 2021 - 193.15 MBI 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.
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Mom Gives You A Girly Make Over - May 18, 2019 - 701.92 MBA Penny Barber Fantasy. Watch the full video in my store and follow me on Twitter.com/PamperedPenny! XOX
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FREE Mommy's Little Diaper Nerd - September 07, 2022 - 213.88 MBWatch the full clip in my store. XO
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My Son's a Werewolf! Preview - October 29, 2021 - 149.52 MBA Penny Barber Fantasy. Watch the full clip in my store! XOX Follow me on Twitter.com/PamperedPenny
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FREE Exposing Mommy's Kinks - December 16, 2021 - 181.62 MBI 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
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Making Bro Try Mom's Vibe On His Cock - September 15, 2019 - 829.7 MBWatch the full clip in my store! XO
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Free Relieving Mom's Holiday Stress - December 24, 2020 - 159.0 MBDo 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
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Jerk Off Into My Diaper, Daddy - January 01, 2018 - 1.75 GBWhen 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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Blowjob from the MILF Next Door - April 03, 2021 - 844.32 MBMom 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
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Little Sister Controls Your Orgasms - June 30, 2017 - 1.75 GBYour 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
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Spying on Auntie - May 06, 2021 - 3.16 GBWatch the full clip in my store! XOX Follow me on Twitter.com/PamperedPenny
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FREE Mesmerized into Diapers - November 19, 2021 - 216.56 MBYou 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
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Embarrassing Diaper Change During Class - June 12, 2020 - 552.93 MBDinner 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?
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Eat Your Vaggies - October 21, 2022 - 4.11 GBOn 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!
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Lois Griffin Fucks Chris POV - August 09, 2020 - 593.01 MBWhere 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?
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Mommy Makes You Miss the Bus - June 14, 2021 - 3.88 GBThe full video is available in my store! XO
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Sharing My Sister with My Son Trailer - December 08, 2020 - 204.38 MBYou’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
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Girlfriend Diapers You for Movie Night - January 10, 2021 - 2.52 GBIt 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
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Diapered & Sissified For Wetting Himself - March 05, 2019 - 1.43 GBI 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
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Mom Tells Date About Your Jerk Off Habit - April 14, 2019 - 647.88 MBAnother 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.
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Fuck Me or I Send You to Live with Dad - May 28, 2021 - 3.24 GBI 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
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Made Into A Baby Bunny - May 03, 2019 - 716.37 MBThere 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.
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Hot Hotel Sex with My Son - February 02, 2020 - 549.55 MBI 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
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Babydick Diapered At School - March 22, 2019 - 818.26 MBWhen 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
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Diapered Blowjob On Date Night - June 07, 2019 - 681.5 MBLooks 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
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Wife Discovers Your ABDL Browser History - December 31, 2021 - 4.57 GBI 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
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Mommy Fucks You to Borrow Your Car - February 25, 2022 - 3.43 GBI’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
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Personal Training with Sis - January 07, 2018 - 1.72 GBMasturbating, 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
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Mommy Milkers - October 21, 2022 - 4.02 GBI 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
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Cock Locked Up After Bad Report Card - August 18, 2019 - 813.1 MBYou 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
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Put On Diaper Probation at Work - November 02, 2019 - 723.89 MBI 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
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Tantric Sex Practice with Mom - November 03, 2019 - 672.67 MBWatch the full clip in my store or on my OF. XO
anal, milf, jeans fetish, pov sex, mommy roleplay
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FREE Mom Jeans POV Anal Sex - January 21, 2021 - 152.87 MBYou’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
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Penny Barber - F-ing With the Principal - January 13, 2023 - 3.79 GBWhat 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
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Penny Barber - My Son is a Vampire! Night 2 - October 25, 2023 - 2.58 GBSo 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
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Mommy's Pussy is for Athletes - November 18, 2022 - 3.51 GBYou 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
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Penny Barber - Maid to be My Mommy - May 12, 2023 - 3.37 GBWatch the full clip in my store! XO
pov, blackmail fantasy, pov sex, taboo, mommy roleplay
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FREE Earning Mommy's Engagement Ring - February 07, 2021 - 155.65 MBYou 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
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Outdoor Blowjob from Mommy - February 14, 2021 - 2.87 GBI 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
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Wet Diaper Face Sitting for Peeping Perv - February 08, 2020 - 689.25 MBA 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
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FREE Sick Mother Fucker - August 03, 2022 - 94.57 MBThis 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
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Diaper Changing Role Swap with Ella Nova - December 13, 2019 - 1.0 GBI 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
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Business Man is Wife's Sissy Baby - April 04, 2020 - 720.03 MBI 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
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Favor for Mommy - October 27, 2021 - 4.6 GBYou 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
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Penny Dominates Your Parents - June 17, 2018 - 1.81 GBA 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
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FREE Mom Catches You Stealing - March 24, 2023 - 96.74 MBOf 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
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Sex Ed With Mommy - October 01, 2021 - 4.58 GBFirst 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
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Mean Boss Becomes Diapered Submissive - April 22, 2022 - 4.54 GBYou'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
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Mom Knows About Your Satin Panty Fetish - April 15, 2018 - 1.82 GBI 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
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Partying With Your Hot Sister - August 12, 2018 - 1.82 GBAw, 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
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Penny Barber - Best Sleepover EVER - April 28, 2023 - 4.43 GBWatch the full clip in my store! XOX
diaper, humiliation, toilet humiliation, daddy roleplay, car
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FREE Penny's Diapered Road Trip - June 26, 2021 - 148.74 MBReady 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
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Penny Barber - JOI to Mom's Yoga Body - July 28, 2023 - 4.45 GBFollow me on Twitter @pamperedpenny
Follow me on Instagram @pampered_penny
Visit my wishlist pamperpenny.com
milf, big tits, cougar, behind the scene
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Getting Older in Porn - June 02, 2018 - 1.83 GBWearing 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
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Naughty Nurse Catches You Stealing Diape - February 06, 2017 - 1.96 GBI 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
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Smart Sis Transformed Into Diaper Ditz - January 18, 2019 - 1.45 GBWhen 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
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Tricked Into Diaper By MILF Landlady - September 06, 2019 - 734.04 MBFind 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
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French Mom Squirts as You Stroke Trailer - December 02, 2020 - 122.36 MBWhat 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
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Pool Perv Diapered by Penny and Ella - July 24, 2020 - 645.06 MBA 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
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FREE - Maid to be My Mommy - May 12, 2023 - 140.64 MBA Penny Barber Fantasy. Watch the full clip in my store! XOX Follow me on Twitter.com/PamperedPenny
cream pie, milf, squirt, pov sex, taboo
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FREE Mom Fucks You at Your Sleepover - July 30, 2022 - 1.56 GBFind the full clip in my store! XO
pov, diaper, diaper discipline, diaper fetish, femdom pov
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FREE Diapered by Your Crush - July 10, 2021 - 144.44 MBI 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
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Soft Glove Handjob from Step-Mom - August 02, 2020 - 768.17 MBI 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
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MILF Teacher Transformed Into Slutty Mom - March 31, 2019 - 735.48 MBAlmost 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
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Tricked into Wetting Yourself - May 01, 2020 - 722.03 MBI 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
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Mommy's ABDL Plans for You and Ella Nova - September 18, 2020 - 569.09 MBI 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
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Diapered w/Girlfrien for Costume Contest - November 05, 2020 - 1.76 GBI 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
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Camping Blowjob From Mom - September 27, 2020 - 570.64 MBI 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
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Nurse Penny Decides You're A Diaper Girl - July 26, 2019 - 332.92 MBOn 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
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Mommie Exploits Your Panty Fetish - March 21, 2017 - 1.78 GBI 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
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Babysitter Makes You Wank in Diapers - July 22, 2022 - 1.01 GBI 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
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Footjob with Mom's Dirty Socks - December 25, 2019 - 1.77 GBI 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
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Velma Solves Mystery Of Mister Pee Pants - May 18, 2019 - 707.17 MBJust 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
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Diaper Girlfriend Experience - June 29, 2018 - 1.82 GBYou'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
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Mommy's New Diaper Rules - September 16, 2020 - 1.81 GBYou 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
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Side Chick Diapered by Angry Girlfriend - January 20, 2017 - 1.41 GBIt’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
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Diaper Sex at Work - September 09, 2022 - 4.52 GBAvailable 10/21! Watch here on my ManyVids. XO
milf, older woman / younger man ., pov sex, taboo, mommy roleplay
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Are You My Mommy? Extended Trailer - October 19, 2020 - 178.96 MBWatch the full clip in my store. XO
feet, milf, stocking, pantyhose, mommy roleplay
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FREE Cheating Mommy Takes Control - July 02, 2021 - 231.05 MBI 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
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Futa Family Holidays With Ella Nova - January 20, 2019 - 1007.46 MBWatch the full clip in my store! XOX Follow me on Twitter.com/pamperedpenny
cream pie, diaper, diaper fetish, pee, public flashing
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FREE Diaper Date Cream Pie - July 22, 2021 - 176.87 MBMy 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
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Natalie Mars Demoted Office Diaper Slut - April 26, 2019 - 727.33 MBI 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
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Too Old For A Babysitter - March 29, 2016 - 1.28 GBI 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
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Bribing Mom For A Blowjob - September 29, 2019 - 742.67 MBHoney, 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
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Penny Barber - Controlling Top Pantyhose - June 23, 2023 - 1.79 GBYou 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
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Very Inappropriate Afternoon With Mommy - August 01, 2021 - 2.57 GBIt’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
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Wet Diaper JOI with Daddy - January 05, 2018 - 1.81 GBThis 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
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Seduced Into Diapers - September 03, 2021 - 4.52 GBAll 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
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Wife Regresses Hubby Into Adult Baby - August 29, 2020 - 464.56 MBWhat 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
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Sexy Mom Is Secretly A Super Villain - July 28, 2019 - 489.06 MBIt 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
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Cheater Tricked Into Sissyhood - January 05, 2016 - 280.47 MBA 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
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FREE Still Mommy's Diaper Boy - March 13, 2023 - 201.46 MBOne 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
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Mom Fucks You & Locks You in Chastity - May 03, 2020 - 587.02 MBCan 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
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Strap-On Punishment For Mommy's Perv - February 03, 2019 - 991.56 MBI 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
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Special Easter Holiday Handjob From Mom - May 26, 2019 - 781.79 MBAre 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
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Nurse Barber has Plans for Your Bottom - April 17, 2020 - 666.09 MBMy 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
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Diaper Blowjob from Penny and Lita - May 09, 2020 - 829.8 MBI 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
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Mommy Takes Your Big Load - October 16, 2021 - 3.44 GBYou’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
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Cheerleader Sister Teases You Until - December 03, 2017 - 1.75 GBYou’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
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Footjob from Mommy - June 18, 2021 - 2.44 GBI’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
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Roommate's Diaper Punishment - February 22, 2021 - 4.17 GBI 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
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Evil Sister Shrinks Your Dick - August 11, 2019 - 393.93 MBAre 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
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Titty Fucking Mom - September 17, 2017 - 1.75 GBI 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
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Therapist Cums After Diapering You - August 21, 2020 - 622.06 MBI 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
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Squished by Mom's Tits and Ass - November 29, 2019 - 660.53 MBWe 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
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Making You Into My Son's Sissy Sex Toy - July 01, 2022 - 759.5 MBBusty, 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
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My Breast Implants - March 01, 2019 - 1.76 GBMommy 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
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Handjob Bet With Mom - March 11, 2022 - 4.57 GBI’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
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Penny Barber - Watching Porn With Mommy - August 04, 2023 - 4.31 GBI 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
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Mom Fucks You in Your Fort - February 23, 2020 - 652.11 MBYou 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
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Coming in Mommy's Pussy - August 19, 2022 - 3.1 GBIt’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
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Mommy Diapers, Plugs, and Cucks You - February 04, 2021 - 4.53 GBi 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
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Diapered Titty Fuck After Workout - January 11, 2017 - 1.3 GBWatch the full clip in my store! XO
big tits, older woman / younger man ., pov sex, taboo, mommy roleplay
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FREE Mommy Knows You Fuck Your Sister - February 27, 2021 - 160.8 MBI 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
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Diapered In Front Of Naughty Nurse - June 28, 2019 - 671.66 MBI 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
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Making Mom Wear Sexy Lingerie - February 24, 2019 - 839.02 MBI 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
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Mom's Slutty Dress Up Motivation - June 17, 2022 - 550.35 MBA 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
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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
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Exposing Mommy's Kinks | Penny Barber - December 17, 2021 - 3.63 GBGuess 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.
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.