Gay Jail Stories

582 results
Orientation
Length
Source
Infinite Scroll

Jail Time Ch. 01

by oralguy82 on Aug 18, 2017
Gay Male

I was spending a couple of weeks in the county jail waiting for trial for a little misunderstanding over the ownership of a car. The first couple of days weren't too bad. There were 16 cells on my floor, and 5 guys serving short time. I was starting to get pretty horny, and that was it easy to take care of, but still not really all that satisfying. I wante...

Not in Kenya

by sr71plt on Aug 18, 2017
Gay Male

"Is the prisoner here, in the examination room?" The doctor for the central jail in Nairobi and I were standing in a white-walled narrow corridor outside a door with a plastic folder attached to it to hold medical records. "Yes, Inspector. His name is John. He's barely nineteen." "How sure are you?" "Very sure. I thought of calling you in immediately. He'...

Caught by a Cop

by boyganymede on Apr 3, 2019
Gay Male

Editor's note: this story contains scenes of non-consensual or reluctant sex. ***** I was back home for the summer from my sophomore year in college. It was a beautiful summer day, sunny but not too hot. I decided to take a drive along a state primary road through a rural area not far from my home town to the riverfront. Traffic was light, so I figured th...

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...

Tasting Trevor

by Pan2 on Jun 9, 2020
Gay Male

We were halfway through a workout when he said the words that would change our relationship forever. My brother Trevor and I been working out together for about a year and a half. Honestly, it was pretty much the only time we spent time together - we were both too busy to hang out much outside of the gym. He's bi, which once upon a time, would have reall...

Prison Tale With 13"

by nnjnyclookingforfun on Sep 14, 2017
Gay Male

Unpaid parking tickets, I'm in the back of a police car on the way to the County Jail because of unpaid parking tickets. How the fuck could this happen to me? A few hours before I was driving minding my own business, when a County Sheriff pulled me over after doing a random license plate check and told me I was pulled over for unpaid parking tickets. My damn...

Fresh Out

by Great_Pharaoh on Sep 14, 2017
Gay Male

Derrick raised his hand to knock on the door to the apartment of his best friend. Well, at least the man who used to be his best friend. He hadn't been able to maintain many deep relationships since he'd landed himself in the Pennsylvania State Penitentiary five years ago. Even his own mother had shunned him, instead choosing to tell her church friends that...

Stallion Station Ch. 03

by sr71plt on Aug 28, 2017
Gay Male

Tucker Singleton stopped in mid stride toward the back of the courtroom, making the man who was following him run into him. "Uh, sorry," the man said. Tucker just nodded a distant recognition. Tucker always floated a bit above the normal press of the "little" people. In this instance, though, his attention had gone to the new line of defendants shuffling i...

Groomed To Be Gay

by Mike Tauron on Sep 4, 2017
Gay Male

Never in my wildest dreams did I ever expect Bill Withers to ask me what he asked me that Tuesday morning. We had worked in the same stockbroker's office for a couple of years and we were sort of friends. Often we'd have lunch together, and his girlfriend Debbie and my wife Linda went out shopping together sometimes. But that morning he had a concerned look...

Arrested!

by Universal_Thirst on Sep 16, 2017
Gay Male

I'd never been arrested before. I was the goodiest of goodie-two-shoes. But when I found texts from my boyfriend of three years to my old roommate that included dick pics and plans to run off to Ohio together (really? Ohio?) I lost my mind for a brief moment. A half dozen margaritas, three cans of spray paint and slashed tire later and an officer was at my...