Gay Jail Sissy Stories

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Jail Time Ch. 02

by oralguy82 on Aug 18, 2017
Gay Male

Before, I had spent 2 weeks in the county jail and, I thought that was all done and gone, and would be forgotten. But about 4 months later, I was almost thinking how can I sign up for another 2 weeks. I felt humiliated about the experience, but so turned on too. More than once I had jerked off to the memory of that humiliation. A 25-year-old man thinking ab...

PIXIE Sissy Stripper Ch. 01

by EROTICbearscribe on Dec 24, 2019
Gay Male

The imposing shadow loomed over Benji blocking out the lights from the stage. "I asked you a question," a deep voice said. There were no other sounds in the club. The loud dance music had been turned off a while ago. There was only the clinking of dishes coming from the kitchen. 20 year old college student Benji knew someone was speaking to him, but the...

PIXIE Sissy Stripper Ch. 03

by EROTICbearscribe on Jan 6, 2020
Gay Male

Darryl Powers was on his way to one of the two popular nightclubs he owned. His new sissyboi, Benji, was beside him. The boi looked pensive and vulnerable, especially sitting next to Darryl. At 6'5 and a muscled but well-sculpted 230 pounds Darryl dwarfed the, for lack of a better word, 'petite' college boy sitting next to him. Anyone seeing the two pass b...

Loosing It To a Guy

by sissyboi on Sep 14, 2017
Gay Male

I'm John and from about my early teens I knew I was bisexual. I had crushes on guys and girls at school and fantasised about having sex with both all the time. If I'm honest I have to admit to lusting after guys a bit more than girls. I kept my virginity until I was 18, as I didn't want to rush into anything, also I wanted to loose it to another guy. I had,...

A Bad Day At The Jail

by sexygirl76 on Sep 19, 2017
Gay Male

This story actually has two different versions: a gay version between two men and a lesbian version between two women. Since there are categories for each, I thought I would write a version for each. This is the gay version. Mark Jenkins lay back on his bunk staring up at the bunk above him. He was working on the second half of a 25-year sentence for killi...

Friends...

by lovejackn on Jul 11, 2018
Gay Male

Have fantasies of me succumbing to my secret homo desire to become a sissy cock whore. My plan for my first gay experience starts innocent enough. I invite the guys over to watch movies, chill. My plan is that we binge watch a couple of Marvel series but what the guys don't know is I am also downloading some porn movies using the jail broken fire stick that...

Boxers and Panties Ch. 01

by tjryder on Aug 18, 2017
Gay Male

Boxers and Panties! Chapter 1 Vol 6 of the Omega Fraternity Series! TJ Ryder SISSYTRAIN (author's preface: In the old gay magazine Blueboy from the 70's was an account of a white student at a black athletic powerhouse college, (which I will call Bolus but you football fans will know what it is), and of its accepting white pledges! One of whom wrote an a...

On No He Didn't

by felicia_rene on Sep 21, 2020
Gay Male

Description This is fiction so literary license allows for the omission of condoms, but our reality doesn't. Enjoy safely. Rick a tall well-built handsome entertainer catches the eye of his boss as he works at his night club. The man's lust consumes him and he conspires to twist him and make Rick his bottom. Despite the fact that Rick insists that he was a...

Stefan

by perihelion on Sep 25, 2017
Gay Male

I always preferred the company of boys and never liked to play with girls, even as a child. I have two older brothers and everything in my home was all about three boys. It was a life of sports and typical guy stuff like hunting and fishing, climbing trees, and the things that make a macho father's chest swell with pride. I never really thought much about it...

The Harrington Hotel

by bjmichaels on Aug 31, 2017
Gay Male

It happened again last night. I was sitting at the bar minding my own business at the Harrington Hotel, the one near the airport, enjoying an after work glass of draft beer when a middle-aged man sat next me. There were plenty of open bar stools so he'd made a conscious decision to sit directly beside me. I didn't mind. One of the the reasons I come to the...