Roleplay Stories

1,017 results
Orientation
Length
Source
Infinite Scroll

Detention Ch. 02

by mrpeachesva on Jan 13, 2018
Exhibitionist & Voyeur

Daryl smiled at the text he had just gotten from his sweetie Sevyn as sat on his couch sipping on some Capt Morgan and Diet Dr. Pepper. It was a late Saturday morning and when he had gotten up, Sevyn wasn't there. He looked outside and didn't see her car so he was curious as to where she was. He wasn't worried though. Sevyn was pretty adventurous and liked t...

Roleplaying Another Cock

by CasualPosterWoo on Sep 2, 2017
Erotic Couplings

This is something that just happened today. I've been feeling a bit adventurous lately, in a sexual sense, and my girlfriend has been pretty accepting and open, not to mention turned on by a majority of the things I've suggested. This is one of the kinkier things we've done. Two years ago, when we first met, I would have never been comfortable with this, but...

Accounting Solutions Beatdown

by cody234 on Aug 31, 2017
Fetish

Disclaimer. This story is based on two of my female friends, their names have been changed, as has the business that they work for, they are good friends in reality. I am a 31 year old male, my name has also been changed. Arion Lucas walks into the kitchen of the Accounting Solutions building, he is there for a meeting, but he doesn't see anyone around,...

Lisa - Home Invasion

by TrazO on Jun 2, 2020
BDSM

I came home from work, and the front room was dark. Last time that happened she'd recreated our first date, with our roles reversed. She'd been quite sweet that time and I felt some relief. She'd warned me to prepare for her being less gentle today, but it seemed she might not be so rough with me. There was someone standing behind the front door when I clos...

Cheating Young Girlfriend

by cuckedbymygirlfriend on Apr 14, 2020
Interracial Love

Ever since we met in college, I was wary of what other people would say about my girlfriend. As a nineteen-year-old sophomore, Annabelle was the girl that seemed innocent until you got to know her. I had known her since late freshman year of high school and had watched her blossom from awkward young petite blonde with absolutely no sexual experience to extre...

A Letter To My (Online) Lover...

by Titaniaswhim on Sep 13, 2017
Toys & Masturbation

I have known my online lover for several years now. He is a very erotic, very dirty, very attractive older man. We 'play' under the cover of popular MMORPG's (massive multiplayer online role-playing games). We are both happily married - to other people - and wouldn't have it any other way. But he is the pink-icing-roses on my cake, and he never fails to make...

Writer's Fantasy

by SassyAnonymous on Oct 6, 2020
Sci-Fi & Fantasy

Dedicated to my roleplay partner and a wonderful human being, Sarah. -------- You sighed as you finally dropped down on the bed after a long and grueling day at work. Waking up at 5 am was taking its toll on you. There was little you could do now but unwind before you started all over again tomorrow. Hurray, You picked up your laptop and checked to see if...

What Now, Sir? Ch. 02

by brahmin on Aug 30, 2017
Mature

Yes, I know. I've been the silent partner so far in this escapade. An ex-girlfriend used to call me Mr. T, because she said I was such a tease, so let that be my moniker for now. I'm in my early thirties, an average guy in looks, with perhaps a bit of a baby face, or so some have said. I stay in shape and women generally find me attractive, particularly the...

A Day in the Lifestyle: Pee Play

by secondsamuel on Mar 12, 2019
Fetish

Author's Note: My wife and I have been together for five years. We have been in the swinging community four years. In the time we have indulged in many fantasies. I am incredibly fortunate to have such an open-minded and sexual adventurous partner. With her permission, this series will share some of more memorable times together, to the best of my recollecti...

Paige Ch. 02: Birthday Girl

by SZENSEI on Oct 30, 2018
Exhibitionist & Voyeur

As the sunlight pierced her curtains Paige Turner stirred in her bed. Snuggling up with her new Down comforter and a teddy bear that she always napped with her first coherent thought was..."Donnie." Laying there warm and cozy her memory of last night made her smile. While never expecting the event to actually happen she was excitably happy it did. Her Dad wa...