JackieSynn

JackieSynn-Amateur-Taboo, JOI, BBW, Mommy Roleplay, Big Tits

Full HD-239,5 MB-jackiesynn mom makes you cum before bed

AVC, 3885 Kbps, 29.970 fps
AAC, 192 Kbps (CBR), 48 KHz, 2 channels
duration 00:08:12
::This was a custom video for a fan, no names were used::



“You’re my mom you come to check on me in my bed but I’m restless. My girlfriend and I just broke up and I’m upset and can’t settle so you comfort me. The first 3-4 minutes I want you talking about how everything will be ok, I can do better, her tits were small anyway etc. Then I want you to kiss me goodnight and notice I’m hard. I want you to simulate jacking my dick (no toys please, just simulated) and telling me to cum for mom, taking off your top and teasing me with your huge mommy boobs.”

Download link jackiesynn mom makes you cum before bed.mp4 - 239.5 MB

JackieSynn-Amateur-Mommy Roleplay, BBW, PAWG, Big Tits, Vibrator

Full HD-164,1 MB-jackiesynn come home to mommy college boy

AVC, 3004 Kbps, 29.970 fps
AAC, 192 Kbps (CBR), 48 KHz, 2 channels

Mom really misses you, you've barely called since moving off to college. She's left you loads of messages, but hasn't heard a word so she thought sending a video would help. Don't you miss your loving mommy? Don't you know how much she craves your sweet young cock? Mom becomes overwhelmed making this video for you and loses control, cumming hard on her favourite toy. Stroke along and reminisce about your naughty days back home with mommy. You'll come home soon to visit, right son?

Download link jackiesynn come home to mommy college boy.mp4 - 164.1 MB

JackieSynn-Amateur-Mommy Roleplay, Humiliation, Femdom, Big Tits, Jerk Off Instruction

Full HD-252,1 MB-jackiesynn mean mommy makes you expose yourself

AVC, 3367 Kbps, 29.970 fps
AAC, 192 Kbps (CBR), 48 KHz, 2 channels

Mom's just gotten a message from some random girl that goes to your school. The message includes screen shots of your conversation with her along with pictures of your hard dick, even though the girls asked you not to. mother is appalled her son would do something like this and decides to teach you a lesson. You want to send unsolicited dick pics? FINE - mommy will record you and post you jerking off in front of her to your whole school! Everyone on your contact list is going to see you jerking off while mommy mocks you for being such a pervert. She knows you like big tits so she pulls hers out to further humiliate you. You're going to cum for your mom's big tits in front of everyone you know! That's what you get, pervert!

Download link jackiesynn mean mommy makes you expose yourself.mp4 - 252.1 MB

JackieSynn-Amateur-Small Penis Encouragement, Small Dicks, SPH, BBW, Big Tits

Full HD-199,6 MB-jackiesynn small penis baby talk joi

AVC, 4099 Kbps, 29.970 fps
AAC, 192 Kbps (CBR), 48 KHz, 2 channels

Aww, is your wittle dicky hard? Let Jackie help make your tiny cock cum with her expert JOI and intense cum encouragement.

Download link jackiesynn small penis baby talk joi.mp4 - 199.6 MB

JackieSynn-Amateur-Mommy Roleplay, BBW, PAWG, Cock Tease, Leather

Full HD-231 MB-jackiesynn slut mom in leather makes you cum

AVC, 2895 Kbps, 29.970 fps
AAC, 192 Kbps (CBR), 48 KHz, 2 channels

Mom's getting ready for another wild night out with her friends. She's dressed like a slut in a leather jacket, tight leather look leggings and high heels. Ever since the divorce she's been acting like a filthy whore! Late nights partying with strange men, coming home at all hours... you have to admit, she looks amazing though. When you confront her about it she ends up mocking you, telling you to loosen up as she teases you. You get hard and can't hide your erection, mom decides she's going to make you pull out your cock and pump for her big tits & her leather clad ass. you try to resist, but you know you can't. You cum stroking to mom's hot body as she describes all the cock she's going to get tonight - your mom loves being a dirty cock slut!

Download link jackiesynn slut mom in leather makes you cum.mp4 - 231.0 MB

JackieSynn-Amateur-Daddy Roleplay, Daddys Girl, Gagging, BBW, Blow Jobs

Full HD-497,5 MB-jackiesynn bitchy goth goth daughter gets punished

AVC, 7013 Kbps, 29.970 fps
AAC, 192 Kbps (CBR), 48 KHz, 2 channels

Your goth slut daughter comes home messed up from the club again and you catch her catch her masturbating to BBC porn on the couch! She's embarrassed but belligerent and starts acting like a real bitch, mocking you and calling you names. She thinks it's funny to call you a pervert and tell you what a slut she is just to break your heart. Your daughter even goes as far as showing you her asshole while confessing she loves fucking strange black men! You've had enough and decide it's time she was punished for her filthy ways, if she wants to act like a slut, you're going to treat her like one. You c * your daughter down on your big daddy dick and make her gag hard until she begs for mercy, of which you show her none. Open wide for daddy, whore!

Download link jackiesynn bitchy goth goth daughter gets punished.mp4 - 497.5 MB

JackieSynn-Amateur-Financial Domination, Mommy Roleplay, BBW, Big Tits, BBW Female Domination

Full HD-228,2 MB-jackiesynn greedy mom findom

AVC, 2201 Kbps, 29.970 fps
AAC, 192 Kbps (CBR), 48 KHz, 2 channels
duration 00:13:17
You just nailed the big job interview of your dreams, you’re going to be making half a million a year! You come home excited to tell your mother, but she is busy on the phone talking to your little sister. After she gets off the phone she acts so excited for you she is so proud of her young son having such a prestigious job! Mum make sure to remind you all of the sacrifices she’s had to make over the years to get you to where you are, she had to work three jobs to pay for your education. Mum tells you that tonight you’re going out for dinner with her and your little sister to celebrate, and you notice mum has on a very sexy new blue dress. Mum sees that you like her cleavage, so she teases you as she tells you that you need to start contributing. Mummy is so efficient, she’s already set it up with the bank to have part of your paycheque funnelled into her account every month. You start to protest, especially when you hear the exorbitant amount that she wants, but mum starts pulling out her big boobs and encouraging you to pump for them. You are so weak for your mum’s boobs, you’ve been jacking after her tits for years. Mum reminds you that she knows that you’ve been sneaking into your little sisters room at night to jerk off to her little panties as well. You don’t want all of your friends and your new boss to know that you’re a dirty pervert do you? Well then you better comply with mums demands, mum has you stroke until your broke. You’ll do anything for the chance to come on your mothers big boobs, but will mummy let you have what you want? Not until she gets what she wants, mummy is such a greedy bitch!

Download link jackiesynn greedy mom findom.mp4 - 228.2 MB

JackieSynn-Amateur-Taboo, Mommy Roleplay, Jerk Off Instruction, BBW, Big Boobs

Full HD-326,3 MB-jackiesynn make cummies for mommy

AVC, 4307 Kbps, 29.970 fps
AAC, 192 Kbps (CBR), 48 KHz, 2 channels
duration 00:10:07
Mommy knows how horny her wittle man gets mommy baby talks, mommy loves making you rub yourself in front of her. Do you want to see mommy's big boobies and make cummies? Yes you do, you naughty little man, show mommy what happens when your pp gets hard. Mommy is so loving and encouraging, you're going to make big cummies like a good boy, aren't you, son?

Download link jackiesynn make cummies for mommy.mp4 - 326.3 MB

JackieSynn-Amateur-Home Wrecker, Gothic, Taboo, PAWG, BBW

Full HD-495,1 MB-jackiesynn slutty goth sisterinlaw is a homewrecker

AVC, 4329 Kbps, 29.970 fps
AAC, 192 Kbps (CBR), 48 KHz, 2 channels

You come home to find your conservative wife's sister talking on the phone. Your sister in law is nothing like your wife, she's a curvy goth party girl slut - everything your wife is not. She asks to borrow money to go out clubbing but you're reluctant, after all, you're a good Christian family man who doesn't approve of your sister in laws promiscuous ways. Jackie always gets her way though, soon you find yourself slipping into her dirty trap (in more ways than one) and find that you can't resist her...

Download link jackiesynn slutty goth sisterinlaw is a homewrecker.mp4 - 495.1 MB

JackieSynn-Amateur-BBW, Confessions, Mommy Roleplay, Pantyhose, Pantyhose Footjobs

Full HD-411,6 MB-jackiesynn mother and son therapy

AVC, 1607 Kbps, 29.970 fps
AAC, 192 Kbps (CBR), 48 KHz, 2 channels

::this was a custom video for fan Michael::

“My mom moved in with me about a year ago and started wearing pantyhose daily about three months in. After a few of my girlfriends were talking about how I had a nine inch cock. My mom casually said I can confirm. I was simultaneously aroused and ashamed. We were going to watch a movie and I wanted to rub my mom's feet because I thought it would give me "masturbation material" later. Just asking lol. She actually said yes because the movie was Cleopatra (over 5 hours!), After an hour she let me off and simply rested her ethereal pantyhose clad feet on my inner left thigh. The side I hang my cock. In slow motion I saw her feet come closer and my cock expanded to feel her feet come to rest on it. After about another 15 minutes my mom was so into the movie she started rubbing her feet together on my thigh more precisely my throbbing cock. I got a world class view of her pantyhose covered legs and ass. Even some up-skirt of her gusset. I was staring at her feet the mostly her feet seemed to be caressing my cock. She caught me looking and said "NO!!! my feet stay there for the entire movie!" Her toes twitched and pinched the head of my cock and I came one of the hardest times I ever had. I came at least five times by the end of the movie. I felt a lot of shame when her feet moved away and I saw a string of cum from the cock head in my jeans going to the bottom of her pantyhose encased foot.


I kinda want to watch Cleopatra again lol. I wanted to get a custom where I can basically get a little --- during the movie and after “cast” said custom to the screen and have you tell my mom about that and say I masturbate with her worn panties and pantyhose. Confessional and that I want footjobs from my mommy and for her to suck me off as she does the footjob. Also that I want to go balls deep and hit the back of her uterus and paint it white with steamy jizz ropes.*



I want you in pantyhose and wear them throughout even if it ends with you just in pantyhose lol. Maybe therapist like clothes to start.



I just imagine you starting seriously slowly revealing the fucked up nature of my feelings and what happened (5 minutes or so.) revealing how bad I want to get a footjob from my mommies pantyhose clad feet while she simultaneously leans over and sucks my cock. How I jerk off in her pantyhose and panties. Sometimes sucking her cum/discharge out of the pantyhose and panties first after I massaged her pantyhose covered feet for multiple hours. Presumably making her wet or actually coming. What happened watching Cleopatra... and why I wanted to watch it again. How fucking her through her pantyhose would be a great bonding experience! Nothing better than going balls deep in your own mother hitting the back of her uterus and eventually erupting a massive load of millions of sperm frantic to impregnate mommy... if she can even get pregnant. According to our deal I have to get her pregnant and if she can’t well... I have to keep trying a few times a day anyway.”

Download link jackiesynn mother and son therapy.mp4 - 411.6 MB

JackieSynn-Amateur-Taboo, CEI, BBW, Mommy Roleplay, Big Tits

Full HD-236,2 MB-jackiesynn moms cei punishment

AVC, 3131 Kbps, 29.970 fps
AAC, 192 Kbps (CBR), 48 KHz, 2 channels
duration 00:09:55
Mom is so tired of you not being able to control yourself, all you do is masturbate! You've gotten in trouble for it at school, the gym, and you're always blowing your load all over the house & never cleaning it up. Mom calls the doctor for his recommendation, she's willing to try ANYTHING to help you with your condition.; After mom's off the phone, she realizes you've been wanking under the covers while sitting across from her the whole time. Mom decides to put the doctors recommendation in play - you're going to cum in front of your mother, but you're damn sure going to clean it up! Mom makes you eat your load several times, even teasing you with her big tits to aid you along. I hope you're hungry son!

Download link jackiesynn moms cei punishment.mp4 - 236.2 MB

JackieSynn-Amateur-BBW, Mommy Roleplay, Taboo, Phone Sex, JOI

Full HD-284,4 MB-jackiesynn mom is a phone sex operator

AVC, 4144 Kbps, 29.970 fps
AAC, 192 Kbps (CBR), 48 KHz, 2 channels

You come downstairs to find your mom on the couch talking on the phone, but she's not just talking, she's got her tits out and she's talking filthy! You spy on her and realize she's having phone sex and getting very horny. She pays with her tits and starts grinding on her vibrating wand. Suddenly her call ends but she's still getting herself off - that's when she notices you standing there! Mom has no choice but to confess to you that she's a phone sex operator, and that hearing men get off to her really turns her on. You ask mom to keep going with her vibe, but she tells you it's wrong, you're her son after all! But it's only fair, if she gets all those strange men off, why not you? Mom dirty talks and encourages you to stroke while she uses her wand, you can't believe how filthy mom talks! Mom cums hard and you do too, this is a whole new side of mommy, and you're loving it!

Download link jackiesynn mom is a phone sex operator.mp4 - 284.4 MB