Gay Jail Stories

582 results
Orientation
Length
Source
Infinite Scroll

Success is a Little Thing

by literaryvergin on May 15, 2019
Gay Male

I got a scholarship to a small private school to further my education after I finished high school; my family made a big deal of going to Daymare because we were poor, and no one else had gone beyond a high school diploma. Most of the kids there were pretty snobby, at least towards me, so I mainly stayed off to myself. I only had a couple of dates in high sc...

The BBB of Alcatraz

by JJEroticas on Dec 30, 2019
Gay Male

At this moment, Mike shakes like a corned rattler and, his hysterical conscious screams in his skull: I will get through this. You will get one more chance to be a great artist. Cool sweat pools above Mike's ass. His mind buzzes like the dim light over the dumpster. Beige spitball bugs swarm it in figure eights. His leg burns as 'fight or flight' blood poo...

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...

The Gentleman's Agreement Ch. 02

by BenjiBright on Aug 18, 2017
Gay Male

"Officer Hawthorne, can you read that back to me?" Warren looked up, eyes bleary and thoughts elsewhere. He glanced down at the dictation. He had taken it with only a portion of his concentration, but he was fairly sure it was competently done. David Brown, his commanding officer, regarded him with a look of patient disappointment that a governess might re...

Chain Gangbanged Ch. 02

by sr71plt on Sep 14, 2017
Gay Male

After Bobby Joe had fucked me up against a tree, he and Maurice went over to a picnic table then, and I just watched as Maurice rolled another condom on Bobby Joe's rising cock and they slowly aroused each other to the point where Bobby Joe laid Maurice on his back on the picnic table and held his legs up and out from his body, as he pumped away inside the g...

Lessons Taught

by Ky049 on Aug 18, 2017
Gay Male

I'm your typical punk scene guy. You can find me out with my boys or at shows slamming on the floor. This is about an experience after a show a few months ago. I was walking home from the bar, it was after midnight sometime. I was already done coming down off of some dope, and just wanted to get to my place and fall out. Walking down the main road, bad nei...

Quenching the Thirst

by HerLittlePiggy on Sep 14, 2017
Gay Male

"I want you to fuck me," I said softly as I pressed my body against his. I slid my hand down the front of his pants and grabbed his already stiff dick. My heart raced and adrenalin coursed through my veins. I couldn't believe what I was doing but it felt good and freeing. I had never been with a man sexually before but I had often fantasized about it. My lip...

A Cop's Night

by yokaichan on Sep 14, 2017
Gay Male

I'd like to thank DeadlyNyghtshayde for betaing and editing, even though I know she wanted to go off and beat the crap out of someone after reading it. Please note, this is a gay male story, and is extremely reluctant and borders closely with rape. If you don't like stories like that, then don't read this, please. ================ ::Three shots. My entir...

Miami Ch. 02

by bominog on Sep 14, 2017
Gay Male

Chapter 2: "Lil' Joe Cartwright" In the first part of this story, I'd just met Miami, and his beautiful cock, which he'd given the affectionate name of "lil' Joe Cartright", "lil' Joe" for short, though I was soon to find there was nothing short about him! But before I begin telling of my many adventures with him, I feel I must backtrack again, and talk a l...

90 Days In Heaven

by bominog on Aug 28, 2017
Gay Male

While this is mostly a tale of sexual fantasy, it is in some ways based on true events. I'm a great lover of big black cock, and have truly had many wonderful experiences with them. All names have been changed, but I did actually spend 90 days with 5 beautiful black thugs, and did get a taste of some of the delicious dark meat, and at least got to see some o...