brother/sister roleplay

Olive Wood – Mommy Leaves Sister in Charge

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Olive Wood - Mommy Leaves Sister in Charge

Olive Wood – Mommy Leaves Sister in Charge

You’ve always been Mommy’s little baby. When she heads out of town for a week, she leaves you in the care of your (slightly) older sister, Olive, and begs her to keep you safe. Mommy delivers Olive a brief lecture about responsibility, emphasizing that under no circumstances is she to invite any boys over.
The moment Mommy shuts the door behind her, Olive swoops in and suggests the two of you plan something reckless. You staunchly refuse to do anything dangerous, but Olive reminds you that she’s in charge, so you must obey her. She lights up and asks you to relay what the two of you did last time Mommy left you alone. You begin to blush and pretend you can’t remember, but she orders you to say it aloud. As you begin to nervously stutter about how the two of you had sex, Olive insists you unzip your pants and expose your cock. She demands that you stroke yourself to her and explains that since Mommy won’t let her have her boyfriend over, you’ll have to entertain her instead. Once she’s satisfied with your state of arousal, she instructs you to lie on the sofa and prepare to be used.
Olive climbs on top of you and begins to tease your cock with her hands and mouth. She rubs herself with the tip of your cock before sliding it all the way inside her, praising you for your ability to properly fill a woman and admitting that she may have a slight thing for sibling sex. Olive rides you until she climaxes several times, alternating between multiple positions to give you the best show imaginable. She reminds you that her own pleasure is paramount, and you’ll be in big trouble of you finish before she’s had her fill. Your mind begins to melt as you try to contain your orgasm, but somehow you manage to make it past the finish line. After what seems like an eternity, Olive comes one last time before rewarding you by letting you finish inside her. You doubt you would have made it another minute if she’d kept going, but you accept her high praise of your stamina and eagerly agree to prepare yourself for another round tomorrow.

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Olive Wood – Mommy, Sister, and the Love Potion

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Olive Wood - Mommy, Sister, and the Love Potion

Olive Wood – Mommy, Sister, and the Love Potion

It’s convenient to have a witch for a mother. When you come to her for help wooing a mystery girl, she knows just the right formula for a special love potion that will help you with your quest. All she needs is one last, special ingredient…semen. When the potion is complete, she sends you on your way, explaining that in order for the potion to work, your lover must consume it in the next 24 hours.
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The next morning, you whip up a hot chocolate and add a few drops of Mommy’s magic potion. The recipient? Your own sister! Do you think it will work?

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Olive Wood – Your Family Loves You

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Olive Wood - Your Family Loves You

Olive Wood – Your Family Loves You

Your sister catches you in the bathroom taking photos of your cock with the door wide open. Knowing that you don’t have a girlfriend, she teases you relentlessly and suggests that you must have been putting on a show so that you’d get caught. She calls your mother over to tattle, but Mommy takes your side. She explains that your sister is far too harsh on you and that perhaps, she bullies you because she has a secret crush on you. In order to gauge your sister’s true feelings, Mommy suggests that the two of you pretend that you’ve been seeing a new girl and is certain that when your sister finds out, she’ll confess her true feelings. You like the idea, but you know you’re a terrible liar and if you don’t REALLY lose your virginity, your sister is going to see right through you. Mommy wants her boy to be happy, so she offers her loving holes and the two of you climax on the sofa moments before your sister arrives. When Mommy announces that she overheard you having sex with a mystery woman, your sister can’t conceal her jealousy and demands that you prove it to her. She determines that the only way to know the truth is to examine your cock and check for signs that you’ve recently been inside a woman. Upon smelling your mother’s fluids on you, she breaks down and confesses that she’s always wanted you for herself. She delights in licking the “mystery woman” off your cock and begs you to bury yourself deep inside her. How can you resist?

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Molly Darling – Degrading Your Bitch Sister

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Molly Darling - Degrading Your Bitch Sister

Molly Darling – Degrading Your Bitch Sister

Self degrading/humiliating dirty talk // dehumanization // words used: slut, bimbo, whore, fleshlight, stupid bitch // Your mouthy little bitch sister has come in to whine at you again for taking her things… your mind starts to wander and you imagine what it would be like if things went differently and you were in charge. You rewind the scenario and it starts over… She would listen to you and degrade herself for you. Like the stupid little bimbo she really is. You could use and stuff her holes with your cock before filling her and showering her in your cum. It’s all in your head for now

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Phatassedangel69 – Brother Becomes Daddy

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Phatassedangel69 - Brother Becomes Daddy

Phatassedangel69 – Brother Becomes Daddy

Your sister gives you a call one afternoon asking if she can come over and talk to you, and that’s it’s important. You’ve always been close, so of course you say yes and she shows up pretty quickly. You see she has a backpack with her as she sits down on the couch, you can tell she needs something by the look on her face. She starts to explain about how hard it is living with Mom and her new boyfriend, and begs you to let her stay for the week. You think about it for a minute, but you don’t have anything going on next week so you agree. Plus she’s just so sweet and cute, it’s always been hard to tell your sister no. She is so excited when you agree, the two of you decide to stay in and watch a movie and order some food tonight so she goes to change into comfy clothes.
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After the movie, the two of you start to get ready for bed. Your sister is trying to be sincere and tell you how much it means that you’re letting her stay with you. She hates your mom’s new boyfriend, and she laments the fact that neither of you have ever had a good father figure in your lives. It’s so frustrating! You can see she really means it when she says thank you, but her hoodie has come a little unzipped and it’s majorly distracting. After a few minutes she realizes what you’re looking at and teases you about it. She even takes off the hoodie and is just in her bra, mocking you for acting weird about your sister’s body, as if the two of you don’t share everything anyways! She calms down and goes to get ready for bed. You catch a quick glimpse of her half naked in the bathroom, you linger just a few seconds too long. You know you shouldn’t but… it’s not your fault that your sister has her tits out and the door slightly cracked.
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The next morning you wake up and see your sister, she’s so sweet. You think she’s always been so pretty but this morning it just feels amplified. The moment just feels so tender, you can’t help but stare at her face. Since last night though, you also can’t stop thinking about what’s under her top. The tension rises between you, and you try to hide your hard on under the covers. She reads you like a book, she pretty easily convinces you to just let her see it. At first you think absolutely not, but once she throws in the offer to show you her tits in exchange, you can’t help but agree. Showing off never hurt, right? One thing leads to another, and she ends up underneath you while the two of you make out. You slip off her shorts, and her panties, and taste your sister’s pussy for the first time. You both like this so much more than you thought possible. Things keep escalating and she gives you head, begs you to fuck her, and rides you until she cums. She asks you to fuck her doggystyle while she begs for you to cum inside of her, you couldn’t resist if you tried.

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Phatassedangel69 – Dating Your Sisters Doppelganger

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Phatassedangel69 - Dating Your Sisters Doppelganger

Phatassedangel69 – Dating Your Sisters Doppelganger

You and your girlfriend have been together for just about a year, things are starting to get more serious and you’ve decided to bring her home to meet your family. The only thing is, you’ve been keeping a secret from her. A secret that you simply do not know how to deal with. Your girlfriend looks eerily similar to your sister, but it’s not just that-they dress the same, do their hair and make up almost the same way, they even have the same style tattoos!! You didn’t do it on purpose or anything, that’s just what you’re attracted to. It’s not like that’s something you can help. You have made sure to avoid ever showing your girlfriend any photos of your sister that would make her aware, and vice versa. You have only shown your family pictures of your girlfriend where she has her hair back, is covered up, generally where you can’t fully see what she looks like. You know that after this stay at your parents house, everyone is going to know. You are just hoping and praying that no one mentions it and everyone pretends like nothing is weird about your new girlfriend.
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So, the weekend is here and your girlfriend meets the family. It seems like everything is going well and you are doing an okay job acting like there’s nothing weird about this. Dinner goes great and you are pretty sure you’re in the clear. Maybe you were overthinkig it after all. But then, when you are alone with your girlfriend getting ready for bed, she starts grilling you. It’s clear she is simply not going to drop this. She confronts you telling you that if you are having sex with her, then the fact is that you are sexually attracted to your sister. There’s no if’s and’s or but’s about it. You are dating your sister’s doppelganger!! Lucky for you, your girlfriend is almost as perverted as you are. She starts teasing you and pretending she’s your sister. You try to get her to stop for fear of your family hearing you, but she’s relentless. You know she always gets her way when she gets this way. She insists on roleplaying as your sister, at least for tonight. She teases you and pleads with you for quite some time before she just reaches into your pants and starts stroking your cock… while she pretends she’s your sister. And dear god do they look so much alike.. it almost feels like you really are being touched by your sister. And oh lord do you like it. She crawls under the covers and starts to give you a blowjob. She absolutely worships your cock, painfully slowly at first. The pleasure is almost agonizing as she keeps her eyes devoted entirely to yours, fully locked in. You start to slip into a haze and for a moment you just aren’t quite sure if this is your sister or your girlfriend… She holds your gaze. You aren’t sure if you’ve ever held eye contact this intensely. God your sister’s mouth feels amazing. And then she climbs on top of you, straddling your face. She teasingly asks you how your sister tastes and all you can think is “like heaven” as you continue to pleasure her as best as you can while she grinds on your face and tongue. Next, she sits you on the edge of the bed and starts teasing your cock with her ass and pussy. You feel like you really are about to stick your cock inside of your sister for the very first time, you just hope to god no one in the house can hear what the two of you are saying. ESPECIALLY your sister, her room is right next door. After a while she climbs on top of you, determined to cum on her brother’s cock for the very first time. She insists you maintain eye contact with her as she orgasms, she wants to test you. She wants to test how attracted you really are to your sister. If you’re able to resist, then you can cum on your sister’s pretty face… but as she gets closer and closer to climax, so do you. You can feel her legs shaking around your body, her voice starts to tremble, you’ve never seen your girlfriend have such intense reactions during sex. Now you’re even more confused as to who this is, and as she starts to cum, you can’t hold back. You release yourself and cum for your sister, deep inside of her, as she moans and screams for her brother. It’s ecstasy. You have always wanted your sister, more than anyone else. You can’t believe how good she felt. And just as the two of you are coming down from the throes of your taboo entanglement, you realize someone is standing at the open bedroom door… Fuck.

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Olive Wood – Psycho Sister and the Pregnancy Scam

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Olive Wood - Psycho Sister and the Pregnancy Scam

Olive Wood – Psycho Sister and the Pregnancy Scam

In a desperate attempt to prevent her boyfriend from breaking up with her, your sister has decided to feign a pregnancy. Though initially pleased with her ingenuity, she soon comes to realize that she’s not going to be able to keep up the act for long…unless she finds someone to get her pregnant.

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Olive Wood – Your Sister Makes Porn

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Olive Wood - Your Sister Makes Porn

Olive Wood – Your Sister Makes Porn

After your sister unwittingly reveals the fact that she posts videos on a clip site for a living, you do what any good brother would do and offer your services as a stunt cock. On-screen roleplay quickly turns to off-camera debauchery as the two of you realize your lust for one another is far from make believe.

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Olive Wood – Your Sisters and the Pregnancy Pact

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Olive Wood - Your Sisters and the Pregnancy Pact

Olive Wood – Your Sisters and the Pregnancy Pact

There are no secrets between your two sisters, Olive and Olivia. When you start hooking up with Olivia behind Olive’s back, it’s only a matter of time before she tells her twin. The twins call you into their room and Olive confronts you about your “gross” activities, but your perversions aren’t the worst of it. The two of them share some very troubling news—Olivia is pregnant with your baby!
For the twins, a singular pregnancy is unacceptable. They’ve always done everything together and pregnancy should be no exception. In order to keep their bodies identical, Olive has no choice but to be impregnated by you as well. Although she’s mildly disgusted at first, she quickly takes a liking to sibling sex and a filthy familial threesome ensues.
CONTAINS TABOO TRIGGER WORDS AND TWO VERY VOLUPTUOUS BACKSIDES. VIEWER DISCRETION ADVISED

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Olive Wood – Brother and Sister, Public Infidelity

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Olive Wood - Brother and Sister, Public Infidelity

Olive Wood – Brother and Sister, Public Infidelity

You can only spare an hour away from your wife, and ask your sister to meet you in a dark public park so the two of you can play. Anywhere else, you might be seen. She’s elated to see you and wastes no time in shoving her hand down your pants to pull out your cock. After a passionate blowjob ending in a facial, your cum-covered sibling bends over for you and orgasms on your cock. You push her against a gate and eat her pussy before you slide inside her once more, coming for the second time as she begs you to give it all to her and not leave a drop for your wife. 4K.

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