Videos Tagged with #roleplay

GoAskAlex - Deserving of your Load: POV Taboo Roleplay Fantasy

Wed 08 Apr 2026 21:54:03 +0200

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Your elven step-daughter, has been waiting patiently for you to return from your quest, and wants nothing more than to assist you in shedding the stress of your journey.

Your devoted princess begs for the honour of worshipping you - her King - with her hands and mouth… and very little convincing is required.

Your sweet girl uses her soft warm tongue to caress your dripping cock while telling you how desperately she wants to please you. She wants you to feel good… and she wants to be deserving of your load.

This video includes: POV taboo roleplay, fantasy elf princess, cosplay, costume, begging for cum, cum play, cum in mouth, simulated cumshot, drool, sloppy BJ, hand job, taboo fantasy, POV taboo, elven, dirty talking, step-dad, step-daughter, princess, king, royalty, magic

Too Twisted Taboo – Help Step Mommy Pick Out A Bikini

Wed 08 Apr 2026 21:21:03 +0200

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Melodyradford - Rainy day in bed with voluptuous stepmommy

Mon 30 Mar 2026 21:16:03 +0200

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Step milf standing at the window watching the rain as he awakens. Step milf looks back with a smile and says "good morning." Step milf is in just panties and a baggy jumper. He gets excited to see her. She flirts a little before touching herself and showing her ass. They make love and kiss showing every inch of her voluptuous body. He finished and she asks with a smirk do you mind if I finish myself in front of you? He smiles and says of course not! She says you like to watch me don't you. She turns flush as she finished and they lie together with the rain and warm bed.

Sorry about the strange description MV doesn't allow certain words.

Melodyradford - Step-Milf sex-ed first time

Mon 30 Mar 2026 21:16:03 +0200

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Spend the day with your milf. You are a little down after a bully was being mean at school. Step Milfs here to make you feel good.

On the bed we chat, play tickles and have a little rest. My jacket is a little loose and you keep seeing my big breasts. You get horny and touch yourself over me. Don't worry let me help! I give you a little sex education before your first hand job, you cum fast!

I decide to teach you more and ride you taking your virginity. You really enjoy it. You love my big tits.

SashaCurves - With StepMommy, At Last

Mon 30 Mar 2026 21:05:03 +0200

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Your step-dad's business has always taken priority in the family, with everyone else following suit and doing their duty. Today's the day you agreed to a long time ago. The day your new wife and her step-family arrive for your wedding weekend. The wife you've never met and didn't chose. A marriage for the step-family business, not for love. Step-mom puts on a brave face and tells you it will all work out as she watches out the window for their car to arrive. But you can't go through with this, can you? If you don't do something, say something now, that will be it. She needs to know, but how on earth are you meant to tell your step-mother the real reason you can't marry this woman. Could she ever understand?

You catch yourself fantasising vividly about what could be, in the middle of a meeting with the in laws and decide enough is enough. When you finally confess your feelings, she's surprisingly understanding and even lets you try kissing her to "get it out of your system". It's obvious she feels something too, but she can't let this go any further. Hurt that she would reject your love, you cosy up with your bride to be at the pre-wedding party, watching with satisfaction as step-mom visibly gets jealous. She pulls you aside and begs you to stop punishing her, but you've got the opposite in mind. You tease her to the brink of orgasm as she tries to resist, even when your new bride comes knocking, to ask where you are. Sneaking around right under the noses of your new in-laws-to-be only escalates the forbidden passion between you and step-mom's resolve finally breaks...

Anna Scot - Bad Auntie Meets her Match

Thu 26 Mar 2026 20:58:03 +0200

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Auntie Anna is back but not as you know her. Themes of reluctance taboo.

Your Aunt Anna has been roped in at the last minute to house sit for the weekend as your parents are away. You have not seen her in over ten years. She has been outcast from the family due to her involvement in criminal enterprises. You don’t know the details but found articles online that she used to break into peoples homes and steal heirlooms. She turns up, and you're blow away. She is horrible to you, bitchy and completely uninterested in anything you have to say. BUT, omg she is fucking stunning. A MILF you have only ever dreamed of being with, but considering you are a virgin, you are attracted to anything that moves.

She helps herself to the fridge, offering you one. When you refuse explaining you are training tomorrow because you desperately want to get into the police academy, she scoffs. Telling you what a tragic little life you will lead as a cop. During the night, you hear footsteps and rummaging around the house. You go to investigate and find her, red handed, clearly looking for loot. You shout FREEZE and she turns startled. Instead of being worried, she mocks you further. Who's is going to believe a looser like you, a wannabe cop trying to arrest someone with no proof. She manages to get the handcuffs off you and cuffs you to the desk. She phones her partner, explaining she run into a last minute problem but she will sort it. Facing you, staring intently, a smile spreads across her mouth. She offers to take your virginity. HOW THE HELL DOES SHE KNOW? Teasing you relentlessly with her body, she is certain she has gotten you onside when she see’s a boner. Little does she know, you had the key up your sleeve, you break free and push her onto the bed. Cuffing her arms behind her back. You see her trousers already half down from teasing you and you rip them down. She struggles and you thrust your cock inside her, deep, long. You cannot believe how good this feels. She protests but it just makes you hornier and lustful. She was offering this to you 10 seconds ago so you know she wants it. Pulling out, because you dont want to embarass yourself by summing quickly. You flip her over to face you. Grabbing her head, you thrust your cock into her throat. Her beautiful face looks so great with your big cock stretching your mouth. Tears running down her face, this whore is trying to manipulate you. You wont fall for her lies, you have been warned about her. Pushing her back, thrusting in again. Panting on top, you tell her to cum, you want to feel her juices running down your cock. This deceitful criminal will submit to the law once and for all. Covering her face in the biggest load you have ever made, the sirens screech to a halt outside and the boys come running in. Cuffed and covered in cum, you have finally brought her to justice. Aunty Anna will be behind bars for a long time, and you can’t wait to tell the boys at the academy how you did it.

SashaCurves – Disconnected

Thu 26 Mar 2026 20:49:04 +0200

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After the tragic loss of your stepdad, you and stepmom take comfort in one another. But in the persuit of connection, you both become ensnared in a web of your own making. It starts out as a moment of desperation, both of you knowing it's wrong yet finding solace in the intimacy. As the days and weeks pass, that forbidden sexual connection becomes the only thing holding your disintegrating relationship together. You struggle to hide your distaste when stepmom turns to promiscuity, sneaking out to fuck random men she just met. That perfect motherly image you always held of her begins to shatter as the reality of her humanness sets in. But you keep going back to each other because it feels comfortable, it's the only thing that feels like home. That is until you meet a girl. While you start to move on with your life, you watch as stepmom continues to spiral. She can see you slipping away from her and becomes desperate to keep you the only way she knows how...

Harley Taboo – Spoilt

Mon 23 Mar 2026 22:15:04 +0200

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You’ve successfully chased away every man your stepmom has ever brought home. You can’t stand the thought of sharing her. Tonight, after you make her latest "coworker" flee in terror, you hear her sobbing as she collapses on the stairs. You feel a pang of guilt, but mostly, you feel victorious. She’s yours.

But then something changes. Over the next few days, your stepmom starts to act... different. Her clothes get tighter, her necklines lower. She catches you staring and holds your gaze a second too long. The air in the house becomes thick with a tension you don’t understand. Until one day, she corners you. “You want me all to yourself, don't you?” she purrs, slowly taking off her robe to reveal sheer lingerie that accentuates her incredible body. You’re frozen, and turned on beyond belief. You don’t pull back as she takes your hesitant hand and places it on her soft, warm breast. A moan escapes your lips, and you’re lost.

She leads you to her bed and shows you exactly why you never needed anyone else. This immersive taboo POV movie puts you in the stepson’s shoes, featuring a intense psychological build-up, a claiming first kiss, a sensual blowjob where she takes you deep, and passionate sex where she rides you before you finally take her in missionary, claiming your stepmother as your own.

** This video is custom made and tailored to the customers specification. If you would like your own custom video tailored to your personal preferences, please DM me or leave a comment. **

SashaCurves – A New Start

Mon 23 Mar 2026 21:12:07 +0200

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Stepmom confided in her best friend about your taboo relationship and everything came crashing down. You became pariahs, everyone found out, and you had to up and leave to a whole new country to get away from it all. Now you're getting a new start, and you've both agreed it's too risky to continue what you had before. You try to stay away from one another but old habits die hard. Each time you tell youselves it's got to be the last, but you just can't stop. Then you meet the neighbours and everything changes...

For fans of: breeding, impregnation, taboo dirty talk, stepmom and stepson, creampies, outdoors

Olive Wood – StepMommy and the HIPAA Infraction

Mon 23 Mar 2026 21:12:07 +0200

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Your "step-mommy" has never made a great therapist, especially when her patients' problems hit uncomfortably close to home. Though she really shouldn't let you sit in on her sessions, her special guy ALWAYS comes first, even if it means pretending her camera is broken so she can play with you while she works... *TABOO MATERIAL. VIEWER DISCRETION ADVISED*

Adria Nite - You Deserve Better

Sat 21 Mar 2026 20:42:03 +0200

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Your stepmom enters your room when you’re video chatting with your girlfriend. They exchange a few pleasantries and your girlfriend hangs up uncomfortable. Your stepmom strikes up a conversation about your relationship asking you how sure you are that your girlfriend is the one for you. When you say you’re planning on proposing, she starts listing all the positives of being single leading to her trying to convince you that you shouldn’t settle so quickly. She wants you to explore all the possibilities before you make your final decision. She teases you and you end up giving in and taking your pants off. She gives you a blowjob constantly checking how it compares to what your girlfriend does. You don’t know how to feel about it - it’s cheating. Your stepmom explains that this is for your own good and makes you cum. She’s not done with you though. She gets on top of you whispering how this is benefiting everyone, well, except for your girlfriend. She confesses how she hasn’t properly cum with a cock inside her for the longest time. She makes you cum and cums on your cock twice. Now’s your time to do the thinking.

FantasticMsFoxy - You, Mommy and Her Demon

Tue 17 Mar 2026 19:59:04 +0200

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Stepmommy has been struggling lately. She is single stepmother and has a stepson who is becoming quite a man. But there are these... needs she has. URGES. Getting too strong to ignore. Something is about to break and make it's way into her soul. Giving her what she desires most.