Roleplay Stories

1,017 results
Orientation
Length
Source
Infinite Scroll

Mindy's Ordinary Life Ch. 01

by goldenstarburst on Sep 19, 2017
Erotic Couplings

Alright, this is something a little different. Mindy's Ordinary Life began as a CYOA-style roleplay with a user. She provided the scenario and central character, I wrote 95% of the content and gave her choices to make at various junctures to lead the story down different paths. My philosophy with this design was a little bit of regular CYOA (a la Goosebumps)...

Diary of Passion

by Lizette on Sep 13, 2017
Group Sex

February 18th Today was a good day. Spent time with Laura shopping, bought the cutest outfit. Must remind myself to go back to that little bakery...the man working there was...ummmm, so yummy!! Well diary, I'm exhausted...until next time... February 24th Wow!!! That's all I can say diary...went back to that little bakery and met "the man." His name is...

Phone call interrupted Pt. 01

by ambise on Mar 2, 2020
Toys & Masturbation

Steve had enjoyed a rather extended evening pub crawl after work, and was relieved that Jill was not home when he staggered in. Rather than wait-up and watch some late night talking-heads debate on TV, he thought it more prudent, if not diplomatic, to retire to the spare bedroom. After undressing, he retrieved his laptop from the study and lay down, or rat...

His Cheating Slut

by Slutygirl199 on Dec 9, 2019
Erotic Couplings

I liked him. I really liked him. My boyfriend Matt was really amazing. He loved me so much. We met in high school. It was like a typical romance book, captain of the football team falling for some nerd girl. Yeah, I was that nerd girl. Though I'm kind of good looking. I have an average height and C-cup breasts. My brunette hair fall down till my lower wa...

Daddy Daughter... Roleplay 01

by Indianaboy6555 on Mar 11, 2019
Mature

Everyone is over 18. *** I used to work in the media. Specifically, I was what they called an "on air personality". I called it what it was when I started; I was a DJ in a radio station. That kind of work led to a lonely and nomadic life. Sure, I got to travel the country. But I did it alone. The only good thing about it was there were always groupies tha...

Me And My Online Master

by ftpmike1980 on Sep 16, 2017
Letters & Transcripts

This was a chat with my master. Online Master: Hello, lad. Hope you are being a good boy, Michael. Michael: I am doing well. Hope you are doing well. Online Master: Glad to hear you are doing well, Michael. I am also. Let me know when you are ready to play again on cam, lad Michael: ok. sorry we haven't been able to meet up online. i've been busy with...

It's Not What You Think

by AnonymousPerv on Sep 14, 2017
Group Sex

I wrote this in two days, in between other work. It's about a loving couple who try role-playing a rape fantasy. Cute ending. I didn't bother editing it, though. Better stuff coming soon. _____________ This Isn't What It Looks Like Michelle and I had been drunk and laughing it up in the hotel lobby. Having only just arrived in Memphis earlier that afte...

Roleplay Chat

by youngneighbor on Sep 16, 2017
Letters & Transcripts

The following is a fictional chat between Kim (22) and Bob (late 20s). The chat involves roleplay and FFM (and to a lesser degree, FFMMM). All the characters and situations are fictional and written for erotic entertainment only. ************************* Bob: whats the wildest sexual thing you've done? Kim: in cyber, I have done lots... lol... in life it...

House Rules Pt. 02

by GavinNuisance on Mar 16, 2020
Transgender & Crossdressers

Terry laid naked on Lana's couch, face down with his ass sticking up. Her cum had dried. Drowsy, and still a bit tired, Terry began to move, and stretched as he adjusted his eyes to light. He noticed the sun was setting and he was clearly there for at least a few hours. He rubbed his eyes, but noticed a peculiar feeling in his backside. "What the fuck?" He...

Demonic Stricture

by Rambling_Chantrix on May 6, 2019
NonHuman

For the third time this week I woke up sweaty, nipples stiff, heart racing, vagina brimming with ejaculate. I flung the sheets aside and ran my hands over my naked body, trying to transfer the impressions into a sensation that could satisfy me. My pussy was soft, hot, and incredibly wet. Wasting no time on tenderness, I put both hands to work, fingering my...