Gay Sissy Roommate Stories

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My Sissy Roommate

by Kent100 on Sep 14, 2017
Gay Male

Disclaimer: I enjoy writing these stories, both for your entertainment and mine. This story involves, gay sex, non-consensual sex and bi-racial sex. If this offends you, read no further. Like most writers, I do appreciate your comments and votes. Thank you. * It was 1996, my first year at college and my first time so far away from my home, my family and my...

My Sissy Roommate Ch. 02

by Kent100 on Sep 14, 2017
Gay Male

Disclaimer: I enjoy writing these stories, both for your entertainment and mine. This story involves, gay sex, non-consensual sex and bi-racial sex. If this offends you, read no further. Like most writers, I do appreciate your comments and votes. Thank you. Mark glared at me angrily while I tried to scramble away from him. As I cowered to the back of my clo...

My Sissy Roommate Pt. 01

by wolf_hunt on Dec 3, 2019
Gay Male

All characters who partake in sex are over the age of 18. I hope you enjoy! "Relax, Andrew. It's just a party. Yeah, sure there will be girls there, but it's not like they're serial killers or something," I tell my best friend as we make our way to the party. I swear he's always like this. So worried about everything. I don't know how the kid has survived...

The Exploits of Cockslut Kelly 05

by CSK on Aug 29, 2017
Gay Male

WARNING!! THIS IS A GAY MALE STORY, BUT IT IS ALSO AN EXTREME BDSM STORY AS WELL. THIS STORY COULD EASILY BE PLACED INTO ANY OF THE FOLLOWING CATEGORIES DUE TO THE CONTENT: GAY MALE, BDSM or FETISH. I HAVE REQUESTED THIS FOR THE GAY MALE SECTION, BUT IT MAY END UP IN THE BDSM SECTION OR ANY OF THE OTHERS IF THE EDITORS OF LITEROTICA DECIDE TO RE-CATEGO...

My Roommate's Bitch Ch. 03

by marsorian on Sep 19, 2017
Gay Male

It was easy to keep myself busy at work – too busy to have time to think about recent events. I made it all the way to five o'clock without once feeling the need to reexamine my sexuality or my relationship with my roommate but as soon as I walked into the door of the apartment, as soon as I laid eyes on that couch – the one that John had stretched back in j...

Chubby Sissy Meets His Daddy

by vulpinechub on Sep 19, 2017
Gay Male

The following story is a work of gay fiction. It contains sexual acts between males. This story focuses on: Humiliation, diapers, sissy play, domination. Copyright 2014 -- Feedback is appreciated. * My university decided to cancel classes for the day, but it was too late: I was stuck in the worst traffic of the decade. Mainly due to the incompetence of b...

The Birth of a Sissy Pt. 02

by sissymedic1426 on Sep 14, 2017
Gay Male

Upon my return from Orlando I was tasked with making a decision of where I would go to school in the fall. At first I was intrigued by the possibility that I could go the University of Central Florida, but quickly remembered that I had never stepped foot on the campus while in Florida. So it was a decision between the schools in little old North Carolina, at...

Roommate Turned Me Out

by ralphcollant on Nov 2, 2020
Gay Male

It was a typical Tuesday afternoon after my last class for the day. I walked into my dorm room and found my roommate, Mike, watching porn on his laptop. This was not unusual for either one of us. Some of this junk could be quite entertaining. He nodded and said "Hey Tim" as I walked in and then waved me over so I could see what he was viewing. It was some pr...

Wife and I Get a Roommate Ch. 01

by tonyl65 on Sep 25, 2017
Gay Male

It was the early 80s; I was taking a full load in college and working full time. At nineteen I was making good money, going to school, and just married my high school sweetheart. I know it was too young, but it was 80's and I thought the only way out of my parent's house was to get married. We were married for a year now and, at twenty, we had a nice two bed...

Turned into a Sissy

by drogon01 on Sep 14, 2017
Gay Male

I was 20 years old and had been going out with my girlfriend for about 9 months. Everyone thought I was straight, and although I had never really acted on it, I had often had gay thoughts and wanked over other men. So when my girlfriend told me that she wanted to fuck my arse with a strap on, I was interested. I was at university at the time but was home...