Sissy Roommate Stories

20,331 results
Orientation
Length
Source
Infinite Scroll

Lust During Quarantine

by ClosetSissy2020 on Apr 13, 2020
Transgender & Crossdressers

I've been stuck in the house under quarantine for a couple of weeks now and saw a gif online recently that gave me my first story idea. I've been writing for a few days and have got enough to trickle out the first few parts. Some bits are from personal experience, and some are things I've fantasized over. Let me know what you think, I hope you enjoy reading...

Aunt Pamela and Leslie Ch. 02

by fantaseeboy on Jun 25, 2019
Fetish

Editor's note: this story contains scenes of incest or incest content. ***** The days passed incredibly slowly after my meeting with Aunt Pamela. She dominated my dreams and fantasies. She often crossed my mind while in class and I would wind up with an erection and squirming in my seat with the memory of the spanking she'd given me and the reward I'd earn...

Size Matters

by HerLittlePiggy on Sep 13, 2017
Loving Wives

His long hard cock slapped against my cheek. It was humiliating, degrading and embarrassing. I loved it. I have always had a submissive side and being cuckolded by my beautiful wife was an incredible turn on. His rod was over 7 inches long and proportionately thick. It glistened with the juices from my wife's just fucked pussy and a stream of precum flowed...

Steph and Giulia Ch. 01: The Betrayal

by BigHand32 on Sep 16, 2017
Fetish

Giulia was going to be at the party. Stephen still wanted to see her, even if she had betrayed him. Every day, he had given her a ride to school. Every day, he had been there for her. She laughed at his jokes. She smoked his weed. Now she had betrayed him, but when she invited him to the party, he couldn't help but go. A week ago, he had finally got her to...

Why I’ll Never Go Sharking Again

by tsfan84 on Sep 13, 2017
Transsexuals & Crossdressers

Have you ever heard of "Sharking?" Until recently, I never had either, not until my roommate Jason told me about it. Jason and I go to the University of Maryland together, and share an off campus apartment about 15 minutes off campus. A typical Saturday for us is sitting around drinking, maybe having a few friends over, but this day was unusually slow, unu...

Delving into Femdom Ch. 01

by readytokneel2907 on Jun 1, 2020
BDSM

**Chapter 1. Growing up Oh my where to begin, I imagine it is best to start at the beginning (or as close to it as I can remember). I grew up in a relatively medium sized east coast city living what some may call a normal life with two sisters and both my parents. Growing up I was always into sports and when I entered middle school I had begun to focus on b...

A Jamaican Vacation Ch. 04

by sissyashley4bbc on Dec 24, 2019
Transgender & Crossdressers

Rebecca studied me up and down. "What happened to you?" She asked. "I...uh...I..." Ty cut me off, "you look like you are in shock Rebecca. Let's fix you a drink and I'll explain everything to you." "Make it a double," she said as Ty started to make her a screwdriver. He handed her the drink, grabbed a joint, and ushered us outside. Rebecca sat down...

Your Roommate Can Finish Me Off

by lefthandfantasy on Sep 12, 2017
First Time

"Please baby, don't stop! I'm so close!" she moaned, "You're fucking me so good!" Julia writhed beneath her boyfriend. She lay in the bed at his dorm, her shoulder length black hair strewn wildly about her face. Her mouth open, gasping for breath as her chest heaved; accentuating her medium sized breasts. Her slim and toned body, glistening with sweat, was...

Watching Chrissy

by jx88 on Sep 16, 2017
Transsexuals & Crossdressers

I was Chrissy's roommate for a year or so. I was more or less stuck in "the friend's zone" with her as they say. She trusted me though, and I was always happy to keep her company. She had a few dates now and then, though usually they didn't lead to anything serious, and most guys were kind of turned off by her having a male roommate in the first place. But...

Topped from the Bottom Ch. 04

by cutebabysadie on Sep 14, 2017
Fetish

Summary of previous chapters: Chapter 1: Todd, college football quarterback and alpha jock make a bet with his short nerdy vocal music roommate, Mark. The bet was that Mark could fuck Samantha, Todd's girlfriend, better than Todd. To be specific in just 10 minutes she would be orgasming and screaming his name. It ends with Todd humiliated on his knees eatin...