Gay Sissy Roommate Stories

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You are a Sissy Pt. 03: Body

by Roland15Rollin on Dec 24, 2019
Gay Male

Hello. Hello, sissy. You have come back. You have come back again for another session. Welcome back, faggot. My sexy sissy faggot bitch. I am so glad you have come back. But you have no choice, do you, sissy? You have to come back. You need to come back. You need to hear my voice. It is the voice of truth. The voice that tells you what you are. What you tr...

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...

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...

Submitting To My Roommate...

by chriscili on Aug 18, 2017
Gay Male

Submitting To My Roommate: My New Gay Life I was 18 years old when I had my first gay experience. I was at a private all male college (yes, a few do still exist), it was my freshman year and I shared a room with another freshman named Chris. It seemed that other guys could tell right away the Chris was gay but it didn't cross my mind – I was too concerned w...

Seduction by Shaving

by magmacdowel on Sep 5, 2018
Gay Male

It all started in Women's Studies. I was chatting with some half-closeted freshman who couldn't be bothered to come out and say what he wanted - to fuck my little sissy ass - when the professor started calling around the room for answers to a question I hadn't even heard. I turned to my roommate, Dylan. He was 6'4" and built like Superman, and I'd have let...

Fraternity Slut

by oskarwild on Sep 14, 2017
Gay Male

College was great! High school sucked. And Sam was glad to leave it behind. He had been an awkward boy in high school. Short and skinny - only five-six and a hundred ten pounds - and pimply-faced, he had never been able to attract the hot girls that the jocks were able to get. But things began to change when he hit his eighteenth birthday shortly after gradu...

An English Boy Gets Turned Out Ch. 02

by RustyRover on Sep 14, 2017
Gay Male

Sam woke up the next morning with his usual morning hard on. As he put his hand on his erection yesterday's events suddenly leapt to the forefront of his mind. He felt himself blushing as he was submerged with a wave of humiliation. He remembered he was going to be working in a gay porn shop for the foreseeable future, he remembered picking up an enormous di...

Earning Wally an A

by mklit74 on Aug 18, 2017
Gay Male

I realized in college that I was that I was gay, submissive, and that I worshipped my roommate Wally's amazing dick. My relationship with Wally grew over the course of our college career. I would rush home after class to meet him, trying to get home quick enough to change into lingerie, especially a French maid outfit he was particularly fond of, and meet h...

The Exploits of Cockslut Kelly 01

by CSK on Aug 29, 2017
Gay Male

Hello my fellow perverts and welcome to my very first story on Literotica (but certainly not my last. My little perverted mind has so many lovely stories and fantasies to share with you). I love this site because we can share our deepest, darkest and most depraved fantasies (and past experiences) with other likeminded individuals. My stories will most likely...

Improper Advances Ch. 04

by bjmichaels on Sep 19, 2017
Gay Male

I became lost in the sucking. Every time I went faster, he would slow down the pace. I gently stroked his shaft and caressed his balls. My own balls were so painful I knew I wouldn't last much longer. This time when I furiously bobbed my head faster-and-faster he didn't slow me down. I was so consumed with the rigid pole of flesh inside my mouth I though...