Gay Jail Stories

582 results
Orientation
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Infinite Scroll

Old-School Mayor Of Bi-Cameral Town

by Coxswain on Sep 19, 2017
Gay Male

for thegreatmuppetcaper, sweaty_briefs, Sneu, & mt1rosie When I retired from the Army, I was taken care of--medical care, a little income--but I would have to get a civilian job. After 20 years in Special Forces, I was ready to lay down my sword. I'd been in firefights, wounded a couple of times, chased through jungles, attacked in the desert. I was ready t...

A Rape in the Belfry Ch. 09

by Decayed Angel on Sep 16, 2017
Gay Male

After getting cleaned up and dressed, Rocco and I took a ride in the police cruisers back to the police station. Once we were fingerprinted, photographed and booked, they moved us to the back into some holding cells. Since it was already early evening on a Friday, it looked like these holding cells would be home for the weekend. Fortunately, although we were...

An Odd Sound Thru a Paper Thin Wall

by Decayed Angel on Aug 18, 2017
Gay Male

It was an odd sound coming through the paper thin walls, a strange metallic whir and then a loud, distinct click. It was a sound that seemed to repeat several times during the day and then simply stop. If anyone cared, they might wonder if it was perhaps a ceiling fan about to break down, or maybe a refrigerator about to expire, but nobody cared. Jay lived...

Shocked Into My Place Ch. 08

by pat_7223 on Sep 14, 2017
Gay Male

After shutting down the website, Derek shifted his plans for me to ultimately make even more money off me and eventually get me out of his life. I cleaned up after all the porn shoots and have to admit, I looked damn hot with my piercings, fake tits and tattoos. Derek had a brother in prison who lead a powerful gang, and decided that I should be a gang mem...

Drill Sargent Ch. 01

by siktici on Oct 15, 2017
Gay Male

WARNING: This story contains words that may be offensive to some readers. As they are not the author's point of view, such words were used liberally in basic training, especially back in the seventies. And I assure you, oh savvy reader, the story is fictional. All characters are over 18. This is basic military training of a very different kind. "How's the...

Punishment or Pleasure

by Ewriter111 on Dec 10, 2018
Gay Male

I walked out of the county jail where I was in a holding cell for two and a half days very slowly and slightly bow legged. I had just turned 18 and made the mistake of mouthing off to a police officer during a traffic stop. It was early Friday evening and I didn't have a court hearing until Monday morning. I was put in a remote holding cell with three older,...

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...

My Best Friend Mark Pt. 05

by koksocker333 on Nov 4, 2019
Gay Male

When we got to work Mark's car was destroyed, there was nothing left of it, the windows had been smashed out, the headlights destroyed, damage to every square inch of the car, she had even set the car on fire. The fire department and the police were looking for Mark, but he was no where to be found, they feared he may be hurt, or worse, the video footage sho...

Sissies love big black cock

by Yelawolf on Nov 16, 2017
Gay

Welcome to the story you crazy sissies and you strong aphla black males. This is from edithis and I want to bring here so you guys can write or read or for the real reason you're here to masturbate. Get your hand, dildos, lube, and whatever else you need to jerk it off. Time to begin the story up. (Thanks for all of the likes and support on this story. I jus...

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His Debut

by estragon on Aug 18, 2017
Gay Male

As told to my shrink. I made sure he was eighteen. I was at the birthday reception his mother had for him at Church. I remember when his mother and her husband went to Russia to fetch him and his sister over here to adopt them, and I was present when they were baptized. When Father Bert addressed them in Russian, their faces lifted up to him. The Russians...