Videos Tagged with Roleplay

SashaCurves – You're Not Quitting StepMommy

Sat 18 Apr 2026 20:37:00 +0200

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Stepmommy comes home tired from work and wanting a fuck to let off some steam. Not the perfect moment to confront her with your decision to quit having sex with your stepmother, but it'll have to do. When she realises you're actually serious and arguing her case won't work, she shrugs it off and tells you you'll change your mind. Days later, she sneaks out of bed with your stepdad and comes to see if you've changed your mind. You stand strong but she tempts you into letting her suck your cock, worried that you'll get blue balls if she doesn't. Now that she's got you hard, your resistance is weakening and when she slides you between her legs to give you a thigh job, you're seconds away from letting it all go. But she stops and leaves you. You didn't want this, right? If you're gonna play games with stepmommy, she's going to play them too. The next week, she approaches you dressed in the skimpiest outfit and holding a bottle of oil. She's decided to sack off her exhausting job and take up a career as a masseuse: she'll be home more often and able to spend more time with her boy, but she does need someone to practice on. You reluctantly lay back as she starts massaging those tight muscles, her huge ass in your face and her pussy grinding against your hardening cock. When she turns around and takes off her dressing gown (what? it's getting hot), she "accidentally" sits right down on your erection and you slide into her wet pussy. She rides you until she orgasms, then apologises: your stepdad's going to be home any minute so we'll have to stop there. You didn't get to cum, but you're trying to stop all this so it's for the best, right? Another night, she shows up in your room horny and practically begging you to fuck her it's been so long, but you stay strong. You think she's given up when she comes back in dressed in slutty lingerie and dripping with oil. She takes out your cock and begins sucking you, keeping you on the edge, stopping each time you're about to cum. You're controlling yourself so well, why not just slide it in for a bit? She rides you and tells you to fuck her in all positions and you can't resist. You make her cum multiple times but just as you're close, she calls it a night. The next week she sits down with you as you're checking your calendar. You might not have successfully quit her cold turkey, but you're proud that you haven't cum inside your stepmother for weeks now! When she realises you've been keeping track, she decides enough is enough. This is all just silly. She takes your cock out and sliding it between her big tits, convinces you to just give in. It's what you both want isn't it? Why deny yourself. Your resolve finally broken, you take her upstairs and fuck her, unloading the biggest load all over her chest. Your cock stays hard, your balls full from weeks of denying your urges and she rides you, your cum dripping off her tits as she begs you to breed her. She knew you couldn't stay away, now she wants to make up for lost time and get impregnated by her stepson...

Miss Malorie Switch – Playing Hookie With StepDaughter

Sat 18 Apr 2026 18:28:00 +0200

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You are on a step-family reunion with your new step-daughter, and she doesn't want to go to the events happening today. She wants to stay home at this nice big cabin with you, so she begs to stay home, pretending she is sick so she can "rest". When she goes back to rest, she cracks the door, so if you passed by, you wouldn't be able to miss seeing her start to touch herself, rubbing her clit and fingering her cunt in the chair for you to watch. She ushers you inside with her finger, seducing you and telling you no one will find out, that this is exactly what she wanted this whole time. Getting down on her knees, she sucks your cock, showing you how much of a dirty slut she can be. Laying back on the bed, you fuck her in missionary and doggy, filling her possibly fertile pussy up with Step-Daddy's cum... Now, tonight, remember to sneak in bed with her... She can't get enough of you.

Bettie Bondage – Crazy for Stepson's Cloned Cocks

Mon 13 Apr 2026 07:18:12 +0200

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You've been away from home for a while, but your new job has brought you to the area, so you figure you'll stay at home for a few days, visit. Maybe not talk too much about your new job... It's not that you're ashamed, but its embarrassing to talk about with *her*. Especially because the reason you're in the area isn't just to do a content swap with another creator or something, but because you're having a sex toy made of your cock.

I mean,you can't believe your career as a porn performer took off, let alone that people would want to use your dick as a toy, but hey, you're not complaining! Of course, she wants to hear everything about this "career pivot." You're hesitant at first, but you two have always been open books with one another, so you tell her. You can tell she's a little shocked but as always, she's supportive and happy for you, that you're happy and successful! You tell her about the toy thing, and that some prototypes will be delivered to the house, if she wouldn't mind singing for the package? Err, your package...

What you didn't expect was to come home early from seeing your old high school buddies to find her directly testing out the two prototypes...at the same time! You stay quiet to watch her finish--rude to interrupt, and besides, she looks so fucking hot with your "cocks" sliding into her mouth and pussy...its not until her shuddering orgasm subsides that she realizes you're standing there. Thankfully, she doesn't clock the huge erection you've got for her.

She stammers an apology and runs away, leaving you to relieve the aching real article in the guest bathroom. But you can't stop thinking about her. You go to her, later in the afternoon, to talk. You want her to know you're not upset. And in fact, that you'd value her input. Market research, you joke, hoping to lighten her mood. Hoping to get her thoughts. And maybe a little more demonstration? You can tell she hasn't had a cock in a while, and that maybe yours have awoken something in her. You're willing to push it, to see how far you can get her to go. Because you want it all, and she deserves the real thing.

Miss Malorie Switch - Stripper’s Taboo Fiasco

Mon 13 Apr 2026 00:55:07 +0200

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Malorie is hosting a corporate party, working as a stripper to entertain the business men. She knows that if her dad or brother ever found out about what she did for work, she would be in deep trouble. Luckily, she hasn’t had any issues.. Yet. Tonight, she works alone, and she wears a mask to make herself seem more mysterious. However, when she dances, she is grateful she wore the mask, because the company she’s dancing for happens to be the same company her Dad and brother work for! She tries to not act surprised or anxious, and they seem not to notice it is her. However, after a bit of dancing, dad comes up to grab her ass. She says no touching, but tonight is full service. She now realizes she may have to fuck her dad and brother, too! She gives them both a lapdance, seeing how hard they get for her, grinding against them. She enjoys every second, even though it is fucked up. When she starts sucking them both off, she gets even more turned on. She knows it is fucked up, and she knows they can never find out, but the fact she knows what is happening is all the more exciting. She blows them both, and then Daddy asks to fuck her asshole. She lets him, as brother watches her tight ass get stretched. She sucks him some, offering bro some of her ass as well. She slips up, calling them Daddy and Bro, but she brushes it off as a taboo kink that she has, and they don’t bat an eye. She eventually lets them double penetrate her, fucking her ass and her pussy. Her brother fills her ass up with his cum, and she loves it. Daddy says he wants to cum in her pussy, though. She doesn’t protest, getting pushed down on the couch and filled up again. Daddy fucks her until he fills her up with his cum. She can’t believe she’s doing this, but she can’t get enough. She wants more and more and more. She even squirts all over her Dad’s cock, so turned on from the taboo nature of it all. Thank God Daddy and brother doesn’t know it is really her…

Jane Cane - Testing My Mom’s Self Defense Skills

Sun 12 Apr 2026 18:39:07 +0200

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Testing My Mom’s Self Defense Skills – 8:37 The last time I gave self defense training to my mom, things got a little wild and crazy. This time, I plan to give her a surprise training session to see if I can make it happen again! I text her to let her know that sometime within the next 7 days I would be giving her another son, and she wouldn’t see it coming. She was all for it and gave me the green light to ambush her. Two days later I go to my mom’s house and wait inside her closet just before I know she will be coming home. I wait patiently for her to get in the room and feel comfortable. Just as she is going to walk out of the room, I grab her around her throat from behind and press my already excited cock into her thigh. I whisper into her ear in a raspy voice, ‘I am going to take you’. I push her head down until she wraps her mouth around my cock. Once I’ve had enough of her mouth, I throw her onto the bed and lift her dress up to gain access to her nicely shaved pussy. I jump onto the bed and grab both of her hands to hold them behind her head as I plunged my throbbing rod into her moist pussy. As I slide inside my mother, I tell her she belongs to me, then I begin to pound her pretty pussy. I roll her over on her stomach and slide my dick back in while holding one of her arms behind her back. Once I can’t hold my cum back any longer, I dump my load inside her pussy.

Lalunalewd - step-Sister Caught and Cums with You

Wed 08 Apr 2026 14:43:07 +0200

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I caught you, my step-brother, peeking through my door. You caught me playing with myself. Turns out that I caught you being excited too. I am flattered that you are turned on by me and you assure me there is nothing to be embarrassed about. So I take off my towel and play with myself. I also encourage you to stroke your cock too. I get turned on by you getting so wet that I am starting to crave your hard cock. I crave it so much I tell you how much I want you to fuck me and cum in me. I want us to cum together and I get so into it that I start talking about you breeding me and getting me pregnant. Once we cum together, I hear our parent got home and try to kick you out!

Olive Wood - The Best step-Sister *NOMINATED BEST VID OTY

Tue 07 Apr 2026 19:06:06 +0200

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You can no longer ignore the sexual tension you experience around your step-sister. When she starts to feel you up under the table at a family reunion and begs you to sneak into the bathroom with her, your body and your cock blindly follow. You can’t believe how good her mouth feels around you. Something about how forbidden this is, something about how your entire extended family is only a room away sends you to a place you’ve never been before.

After your cousins have all gone home, you sit down with your parents for movie night, but you can’t concentrate on anything but your step-sister’s seductive glances and skimpy pajamas. As soon as your parents head to bed, she can’t keep her hands off you and pleads for raw, unprotected sex. The two of you try your hardest to conceal your moans as you drive yourself inside her and cum together, both confessing that sibling sex is an unparalleled pleasure you may quickly grow addicted to.

FionaDagger - Luke And Leia

Tue 07 Apr 2026 07:36:06 +0200

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In an alternate timeline, in a galaxy far, far away... Princess Leia confesses to Luke that she loves him and desperately wants him, and when he tells her about how he's recently learned that they're step-***ther and step-***ter.... The two of them decide that they don't care, it's too late, they need to be together...! The two star-crossed step-siblings fuck passionately and swear to each other that they'll travel the galaxy together until they find a planet that will let them live freely and explore their love for each other!

Heatherbby - Using Step-Bro As My New Toy

Tue 07 Apr 2026 07:29:05 +0200

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FionaDagger - Strip Poker With Your step-Sister

Tue 07 Apr 2026 07:01:05 +0200

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The internet has gone down in your house, so you wander into your step-***ter's room to see if it's the same for her. The two of you discuss what to do while you can't get online, and you settle on playing a card game! You jokingly suggest strip poker, and your step-***ter scoffs and says that's a crazy idea. You imply that she's just a chicken, knowing that this is bound to get her on board with playing! Your step-***ter argues with you that she's not a chicken, in fact she's confident that she can beat you! The two of you begin to play, giggling and teasing each other as you awkwardly lose more and more clothing, until you're both left in your underwear! Your step-***ter loses the final round and reluctantly gets fully naked, shyly hiding herself as you tease her for losing. You tell your step-***ter to sit normally and not hide herself, and she tells you she'll only do this if you also get completely naked! You strip off your boxers, and your step-***ter immediately realises that you've gotten hard during the game. She's shocked but can't look away, and mentions how surprisingly big it is. You ask her if she likes it, and she in***ts she doesn't - but you inform her that you can tell she's lying! She tries to change the subject, and asks what the two of you should do now. You convince her to play truth or dare next, and begin using the game to ramp things up... When you step-***ter goes for a truth, you ask her if she's getting turned on seeing your cock, and she reluctantly admits she is... The two of you gradually confess more and more as your step-***ter relaxes, until finally you dare her to touch your dick. She touches it for only a few seconds, but you can tell she's excited by it. She dares you to touch her pussy, and you discover how very wet she is as you finger her for a few seconds. Soon you're daring her to suck you off, and she even gets carried away, going back for more! Your step-***ter seems to be completely swept up in the game now, looking desperately flushed and aroused, and you're thrilled when she dares you to actually fuck her! She says it only has to be for a few seconds, but of course, once you're inside her the two of you get completely carried away, and you keep pounding her until the two of you cum together! Your step-***ter seems stunned for a few moments afterwards as the reality of what just happened sinks in, and she begins to in***t that that can never happen again... But quickly changes her mind to, well maybe just one more time....

SexSweetBlonde - HOROSCOPE

Tue 07 Apr 2026 05:11:05 +0200

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I think every stepmom reads and believes in horoscopes. But not every stepmom is so impressionable that she is willing to have sex with her stepson just because the horoscope “predicted” it.

But you're lucky. You got exactly the kind of stepmom who is capable of interpreting predictions in such a way that you get a sudden and passionate blowjob. From her. And if only it were just a blowjob. After all, she doesn't mind an impressive cumshot on her face. Now you too will believe in the stars.

**This video contains only blowjob and facial cumshot scenes, no sex**

Olive Wood - Sleepover With Your Sister

Tue 07 Apr 2026 02:11:06 +0200

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You’ve paid your family a surprise visit only to find your step-mother in the midst of post-divorce, midlife crisis. According to your little step-sister, step-Mom has turned your old bedroom into a makeshift dungeon and has been entertaining a never-ending slew of eccentric visitors. Knowing you have nowhere else to stay, your sympathetic step-sister offers you her bed and the two of you doze off, commiserating about your step-mother’s raucous new sex life.

You awaken to find your step-sister sneakily touching herself under a blanket. Although she attempts to conceal her late night fondling, she ultimately confesses, and adds that masturbation is perfectly natural and you have no right to shame her. In fact, it’s so very natural that maybe you should do it too. As the two of you shyly start to touch yourselves, you can’t seem to stifle your lust for each other. One thing swiftly leads to another and…

Can you guess what happens next?