Role Play Stories

168,392 results
Orientation
Length
Source
Infinite Scroll

Race Play Ch. 04

by Samuelx on Sep 16, 2017
Group Sex

My name is Patrick O'Shea and I'm a tall, red-haired and gray-eyed Irishman living in the city of Brockton, Massachusetts. I'm an accountant and I'm happily married to a tall, blonde-haired and green-eyed, deliciously curvy and big-bottomed Irishwoman named Leila Barnes O'Shea. She's a schoolteacher. My wife and I are swingers and we're very much into race p...

I'm Fucking Batman!

by MeganOckers on Jun 9, 2020
Humor & Satire

Those of you who've read this writer's 'Pirate Sex for Beginners,' 'Ticket to Ride' and 'Home Office Intercourse' will be delighted to find another piece of literature that's designed to develop your role-playing skills. They're being written because I recognise that the diversity of your sex life may be suffering during these Covidinous times. And I'm not h...

Thoughts On Size

by simpleup on Sep 16, 2017
Reviews & Essays

As a constant source of embarrassment that seemingly calls my masculinity into question, it's a hard thing to admit. But I guess there's really no other way to say it, so I might as well come right out with it. When it comes to the size of my penis, I come up short. Pun intended. In a strange way, it's liberating to admit. But it's also the cause of a great...

Vivian Ch. 04

by scienceguy950 on Nov 16, 2020
Fetish

(Suggest you read one of the earlier Chapter's first; the story will make more sense. Hope you enjoy). I was driving to get takeout Chinese food for three after my modeling show with Vivian and Li. When I returned from picking up our food, the two women sat on the couch in Vivian's living room, both clothed now, chatting and drinking chilled water. Ladies...

Role Play Again

by Thorre on Sep 15, 2017
BDSM

Daisy prepared herself for the new role play. She and Jack had confided their fantasies of bondage and torture with one another. Daisy had been unbelievably turned on, playing the part of a captured spy, bound and punished until she talked. Now it was Jack's turn. Daisy explored the basement as she awaited Jack's entrance. Jack had done a lot of work over t...

Christina's Contradictions Ch. 03

by Joe A Verage on Sep 14, 2017
Loving Wives

My wife, Christina, like many women, doesn't like to verbalize a lot about sex. Over the years, I've found it's pointless to ask her to talk about subjects she finds erotic. Role-Play, on the other hand is different. A friend's suggestion led to the first concrete proof that Christina had ideas about one of her younger colleagues that lay outside the boundar...

Three-Day Experiment

by songwriter503 on Aug 18, 2017
Fetish

Sachi and I are trying to get pregnant. Or at least she is, with my help. We've been together for over eight years now, and living together for the last three of them or so. Even after all this time, when I'm on the road for work, as I often am, Sachi is still the one I mainly fantasize about. It's not that I'd feel guilty about fantasizing about someone els...

Jenny Horny at Work

by JennyfromNJ on Jul 24, 2018
Loving Wives

Our office is professional, but casual. We have about twenty people that work at desk cubicles on the main floor. The staff is mostly men, but there are some women as well. I am the office manager. My desk is larger and open, facing the staff. Having my back to nothing and no one, just windows here on the second floor allows me to "play" online with a degree...

Interview with a Dominatrix

by HabitofArcane on Sep 17, 2017
BDSM

So I'm sitting on the couch late Saturday night when those annoying 1-900 commercials start to come on. This one's different. A beautiful woman is all decked out in a short mini skirt made of leather with a whip slapping against the inside of her hand. She catches my attention quick, "Ohhh...Hi there, baby," she begins with that soft sexy voice. "If you're i...

Scenes - Act 03

by grgy56 on Jun 5, 2019
Romance

Meredith woke the next morning. Her pussy still pulsed and throbbed and was still wet from her masturbating the last night. She struggled out of bed and made it to the shower. The warm water felt good as it rained over her dark hair, down over her shoulders and dripped form her plump breasts. One hand found her harden nipples while the other found her engorg...