Gay Jail Stories

582 results
Orientation
Length
Source
Infinite Scroll

Runaway

by timmywells on Sep 14, 2017
Gay Male

Plattsburgh, New York, in the summer of 1970... It had been a rough couple of months for Dustin Wood, and his life seemed to fall apart in every way imaginable. First, his mother passed away in the spring, and with her gone, Dustin's father seemed to change into someone unrecognizable, drinking heavily and taking all of his frustration out on his only son....

Turning the Table

by hiddenhuntress on Aug 18, 2017
Gay Male

Disclaimer: This is all fiction, based on my own imagination. They have no relation to the real world. Any similarities of real people or places are purely coincidental. I hope you'll enjoy it. Keegan Richards was one of the fastest swimmers at Montel College. He was not the largest of his team-mates nor was he the tallest at five foot six, but he didn't...

I Sucked The Sheriff

by Web Dazell on Aug 18, 2017
Gay Male

"ADVENTURE (noun): an unusual and exciting, often hazardous, experience or activity." The New Oxford Dictionary of English Welcome to the second story in my new "Adventure" series. (The first is "Devil With A Blue Dress On" in the transgendered section.) My two previous stories "The Arrangement" and "Breaking The Arrangement" were autobiographical. Everythi...

Turnabout

by LetsHaveFun on Aug 18, 2017
Gay Male

It had been a long night and I was exhausted. Even so, I had had a hard on all day long that I was hoping to get polished off this evening. My thoughts of having some romantic time with my wife were dashed when I saw that not only was my son home, but also his jock friend David. There was a relationship that I just didn't understand. My son Mark was a little...

My Little Rose Ch. 03

by UndertakerKiryu on Aug 18, 2017
Gay Male

It was an overstatement to say Garland could tolerate my friends. My camp friends he loved, my more intelligent friends not so much. He detested one friend in particular, a gay guy of twenty four named Gideon. It wasn't the fact that Gideon was exactly like me that bothered him, nor the fact that Gideon's appearance cleverly matched mine, with black hair to...

My Hometown Boy

by wazer on Aug 18, 2017
Gay Male

This is the story of my sometimes partner Rikki. We both went to school together and were good friend for most of that time. We would spend the weekends together just hanging out playing sports and video games together. When we were younger Rikki would stay the night at my place. We would talk into the night eventual coming to the topic of sex. I was a virgi...

The Cycle Ride Pt. 02

by ScotishGuy on Sep 16, 2017
Gay Male

This follows on from another story called 'The Cycle Ride'. I hope you enjoy it. ************************* After the charity cycle ride to Pitlochry and back, the memory of my sexual encounter with Graham was not far from my mind. He had awakened long-buried thoughts and desires. I got really turned on thinking about him and what we did that night. I had h...

Becoming a Star

by perihelion on Sep 25, 2017
Gay Male

I turned the corner and saw the motel. There it was, as he'd said it would be, and my life was about to change irrevocably. I could never go back after I entered room sixteen. I paused and stood on the curb, swallowing hard, my emotions a crazed mixture of fear, anger, strange excitement, and I was fighting tears. Finally I steeled myself to move forward. I'...

A Naughty Moon

by Handymanblues on Jan 28, 2020
Gay Male

(Some long awaited sexcapades are always sure to bring about some major changes in once boring lives. This story has non-human components, gay components, erotic coupling components, interracial components and romance components. Two gay friends of mine, Trevor and Ashton, sought to become first time lovers, to become irrevocably "changed for the better." No...

Eyes Like Winona Ch. 04

by Cruel2BKind on Sep 14, 2017
Gay Male

*And here is chapter four! I just want to quickly announce that my nude day submission will be out in just a few short weeks, so keep your eyes peeled for 'The Goats'. As for the question in the last chapter, I am half finished with my new story, 'File 66: The Aftermath' Stay tuned ^_^ All characters are 18+* I felt dead on my feet by the time I got...