Gay Jail Stories

582 results
Orientation
Length
Source
Infinite Scroll

Don't Look Back Ch. 05

by ShelleyRunyon on Sep 14, 2017
Gay Male

Burnham, Texas wasn't much to look at, at least not from an outsider's perspective. It wasn't exactly located on the road to anywhere, and it held no locations of cultural or other kind of interest that might draw a tourist's attention. No gourmet restaurants, no museums. Not even a single famous grave. The entire population of the community hovered somewhe...

Pheonix Shadow

by BixbiteQueen97 on Dec 24, 2019
Gay Male

(AN: This story is a little slow building. This chapter has some sex in it, don't worry, but a little bit of world-building is due before that.) I plaster a convincing grin on my face as I walk around to wait tables. I hate bright days like this. So many shadows around me whispering into my mind... some louder than others. It's the loud ones that scare me....

Dishonourable Member

by TheDarkCloud on Aug 18, 2017
Gay Male

Colin Young was the future of British politics. Or so he thought, but with some justification as it was the description given to him by one of the leading broadsheet newspapers less than a year ago. He had been an elected member of parliament for six years and was into his second term with a healthy majority and still only 31 years old. He was starting to de...

Colorado and Tim Pt. 02

by zephyer on Aug 18, 2017
Gay Male

I met Allen on line and we chatted almost every evening on line, he lived in Denver and I lived in the mountains in Winter Park. We were talking about gay websites and he mentioned a gay web site and how it listed men on the hunt and places where gays hung out. I looked it up and under cruzeing and found various gay bars, clubs, groups, bath houses, etc. On...

Chronicles of an Academic Predator Pt. 02

by MarkArbour on Aug 17, 2017
Gay Male

Before you read this story, there are a few things you should consider: 1 It contains graphic descriptions of sex between men. In some cases, these depictions may get kinky, and include borderline S&M. 2 It is set in the early 1960s, an era before the Civil Rights Act of 1964 when segregation and discrimination were the norm. African Americans were referre...

South Beach Cop

by HerLittlePiggy on Aug 30, 2017
Gay Male

I sat naked on the bed and watched as my beautiful naked wife took the cop's uniform off revealing his taught muscular body and his enormous semi hard cock. Janice and I were on vacation in southern Florida and we had gotten carried away on the second floor balcony of our hotel. It was a warm night and we had been sitting outside in our bathing suits lookin...

Cell Mates

by Brett315 on Aug 18, 2017
Gay Male

It's been three years, six months, and forty-seven days since I've been laid. A jail with no women is hell within itself. I'm in here because of attempted robbery, but the stuff was rightfully mine! The bitch of a girlfriend at the time stole my things and when I went to get the stuff back, she called the fucking cops on me; and so I ended up here. I guess t...

The Way You Say My Name Ch. 09

by wavyscribe on Sep 25, 2017
Gay Male

"Maybe I'd better do this alone." Dillon paused, his key poised in the Lumina's ignition. "No way, Jamie. Ash more or less tried to ram his cock down your throat the last time. What's he gonna do for an encore, strip you down and rape you?" "Yeah, well, he was drunk last time, too." "Who's to say he won't be drinking this time?" Dillon had a point, but J...

The Way You Say My Name Ch. 13

by wavyscribe on Sep 25, 2017
Gay Male

The narrow, white frame-house was nice enough, Dillon supposed, but there was something about this whole thing that just didn’t feel right. Ben had a sister? If that was true, then why hadn’t Ben ever mentioned her to Jamie before? And where did Mitchell Harding fit into all this? Jamie seemed to be having his own reservations, if his hesitancy to open the...

The Three Day Pass Ch. 46

by JoyStick56 on Sep 14, 2017
Gay Male

This is a work of fiction. Names, characters, places, and incidents are either the product of the author's imagination or are used fictitiously, and any resemblance to actual persons, living or dead, events, or locales is entirely coincidental. As fiction, the characters are not bound by the usual dictates of modern society. Unsafe sexual practices can be un...