Sissy Roommate Stories

20,331 results
Orientation
Length
Source
Infinite Scroll

Beautiful Days Ch. 03

by mrpawide on Jul 14, 2020
Group Sex

Over the next few weeks, we weren't able to get together as a group of eight or even as a group of six, but we continued to see each other when possible. Carly (tutoring) and Jen (running store) both picked up part-time jobs for extra income or a "side hustle" as they called it. Jen and I felt great chemistry with Matt and Naomi, who invited us to their ho...

Mike & Karen Ch. 01

by BiscuitHammer on Jan 13, 2018
Erotic Couplings

Disclaimer: All characters are 18 years of age or older while actively engaging in sexual activity. This story is a prequel/sequel (sprequel?) to my other work, Alex & Alexa. Reviews are welcome; flames will be snickered at and deleted with extreme prejudice. Enjoy! Just a note -- there is an incest romance happening between an important secondary coupl...

Mike & Karen Ch. 12

by BiscuitHammer on Dec 18, 2018
Romance

Disclaimer: All characters are 18 years of age or older while actively engaging in sexual activity. This story is a prequel/sequel (sprequel?) to my other work, Alex & Alexa. As always, many thanks and gratuitous panty shots from Freja and Jeanie to my long-suffering editor and beta-reader for their assistance in polishing up and improving this work. Rev...

Sexual Education 101

by CV on Sep 13, 2017
Group Sex

My girlfriend and I are both students at a large Southern University. We recently took sexual education together as an elective, as we heard it was a great class. It was a great class, and it led us into the most sexual experience of our lives! Stacey and I have been together since High School, and are currently in our Junior year in college. We enjoy a gre...

Beating Around the Bush Ch. 01

by Sucker4Boobies on Sep 14, 2017
Erotic Couplings

"Sex, sex, sex; that's all he can think about." Janine Tyler stuffed another French fry into her mouth and washed it down with raspberry lemonade. The petite brown-haired girl sitting next to her watched her with rapt silence as her friend continued to rant about her recently ex-boyfriend. Like a good friend, Amanda would only sit and nod her head, occasion...

The Party Ch. 04

by tghlawyer03 on Sep 14, 2017
Exhibitionist & Voyeur

Chapter IV Annie Is Stripped And Humiliated While the host and I had awaited Annie's return with the driver, I was commanded to stack my clothing neatly on the floor in front of me; to crawl over to the host and kneel in front of him. His exact words were that my dick "was never to be above the floor and I was to crawl like the white snake I undoubtedly wa...

Coming For Carla

by c_a_m313 on Sep 14, 2017
Group Sex

I was in my dorm room reading some primary source material for my Advanced Political Theory class. It was late when the phone rang. My girlfriend, Carla, was on the other line. She is a brunette who usually highlights her hair so it appears blondish sometimes. She has great tits, soft but not saggy. Carla is nineteen and a freshman. I'm a junior but I met he...

Behind the Story Ch. 02

by Goldeniangel on Sep 11, 2017
BDSM

Author's Note: Again, this follows the line of having some trouble which category to place this in... but I decided that because of the direction it's heading that's the category to choose. Enjoy! ***************************************** Three days after Dru masturbated herself to orgasm at the behest of a fan, she finally got up the nerve to get back ont...

Christi Goes to a Frat Party

by Maresy_Dotes on Sep 25, 2017
Group Sex

Christi had spent 48 minutes and 23 seconds perfecting her look in the tiny, poorly lit dorm room mirror. And that was just her makeup. She batted her falsies flirtatiously at her reflection, admiring her perfectly winged eyeliner that had taken her more than a few tries to get right. She scrunched her wavy hair and tossed a seductive, over the shoulder glan...

A First Experience with Foot Boys

by SluttyMallory on Sep 19, 2017
Fetish

Shelby slowly wandered into the dorm hallway, feeling her legs shaking with fatigue as she wrapped her fingers around the door handle and let herself into the room. Walking into her dark room, Shelby extended her arm and switched on the dim light. She walked across the room and sat down on her soft bed, laying down and running her fingers across her long, sl...