Gay Jail Stories

582 results
Orientation
Length
Source
Infinite Scroll

Coach Made My Mouth Water

by psiloveyou on Aug 30, 2017
Gay Male

I sat there in the quiet locker room in just a towel which was wrapped around my sexy six pack waist. I stood up and flushed my hand through my short blond hair. Only about an inch long, still damp from the sweat of practice. My whole body was glistening with shiny sweat as I walked over to the shower hall. The shower hall was open, no booths. There were j...

"Gasoline" Special

by Decayed Angel on Sep 25, 2017
Gay Male

It's a scam, but with the gas prices as high as they are, it's a scam that's worked great for me. It's a simple scam, with simple math and the best part about it is that I only have to do it when I want to. The toughest part was getting the word out without too many people finding out. While it has some wonderful benefits, they aren't worth going to jail for...

The Customer (Dexter's Saga) Ch. 38

by JoyStick56 on Sep 14, 2017
Gay Male

This story is dedicated to all the real Super Heroes of our time - The Service men and women of our Armed Forces and First Responders. This story is a work of pure 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 l...

Barber Brad

by sr71plt on Sep 14, 2017
Gay Male

"What's up with this, Nick?" I asked as I entered the barber shop at one end of the college town's most established shopping strip. "Last time I was here you were lamenting that all of your customers were dying out or retiring away and you'd probably have to close." I looked around the seats lining the wall opposite the barber's chairs and saw that there wer...

Skaterboi Ch. 03

by dourdan on Mar 24, 2020
Gay Male

I pulled on a sweatshirt and opened my phone looking for a certain app. Even in the middle of nowhere, California, there had to be Ubers and Lyfts around somewhere. I'd moved out of the Napa home, into a motel. And by that I mean, I started walking and didn't stop until I felt tired. And then I did it again, and again. Until I made it to somewhere near San F...

Collateral Ch. 20

by laurasfox on Oct 3, 2018
Gay Male

"Is that you, little bro?" he heard his brother calling for him. "Yeah, it's me," Jake spoke. "I'll make you something to eat." "With your cooking, I might be dead by next week," Diaz joked. Jake helped his brother up on to his good foot and then guided him to the kitchen table. At least he knew how to make scrambled eggs. "How come you didn't go running...

Getting . . . Educated Ch. 05

by sr71plt on Sep 14, 2017
Gay Male

After delivering me from jail and imprisoning me again in his web, Coach Seeman delivered me to Nate's door, ravished and still in handcuffs, which had been moved so that my arms were in front of me, and with my jeans barely covering me. When Nate answered the door, he was wearing only his briefs. As the dorm counselor, he had an actual one-bedroom apartme...

Caught in the Open

by GrimDeal on Aug 18, 2017
Gay Male

On a whim I decided to drive up to the adult “novelties” shop down the road, it just happens to be open twenty-four hours. I got there and browsed around for a while, finally deciding on a couple DVD’s and as I was walking up to the counter I noticed some dildos and butt plugs staged prominently near the register. I glanced at them for a minute and grabbed a...

Clayton Gives Head

by Boxlicker101 on Sep 14, 2017
Gay Male

In the wee, small hours of the morning, Clayton Smithers woke up with an urgent need to urinate, so he slipped out of his lower bunk and used the urinal in the back of the cell. After flushing it and washing his hands, he started to return to his bunk. His ass was still a little bit sore, but very pleasantly so, because it reminded him of the great fucking h...

Sex Slave on Death Row

by erectus123 on Feb 6, 2018
Gay Male

[Ever been to the slammer? Not a fun place. But one thing is true, there are no minors in state prison, all sex in prison goes on between adults whether they consent or not. Sometimes it gets pretty hot in the pen and the air conditioning is usually broken.] SEX SLAVE ON DEATH ROW-MY PRISON BLUE BALLS Just my luck to end up in the state pen with a cell mat...