Gay Jail Stories

582 results
Orientation
Length
Source
Infinite Scroll

Jason's Trip to Mexico Ch. 04

by beefylatn on Sep 25, 2017
Gay Male

Jason was pushed into the jail cell by the two officers causing him to stumble and fall, landing on top of a large snoring drunk inmate as the cell door clanged shut. "OOOOFFFFF!" the large hairy sweaty inmate exclaimed as his eyes flew open and he glared at the naked blond stud that landed on his belly. "I'm so sorry, the cops threw me in here and I trippe...

Falling Off the Wagon onto Cocks

by Magda_Sorensen on Sep 24, 2018
Gay Male

I've been controlling my urges to drive around town naked while stroking my cock for months. It's been a year since I've stripped naked in my car, sitting on a hand towel, and lubed up my cock and drove through the busiest parts of the city naked and hard and masturbating. It's been just as long since I've had strangers cumming on my face, or sucked a cock o...

The Traffic Stop

by Orgone5 on Aug 17, 2017
Gay Male

Trevor knew his goose was cooked when he saw the flashing red and blue lights in his mirror. "Damn, I'm screwed!" he swore. He stepped on his brakes but it was too late. The cruiser had already pulled up behind Trevor's black Celica while the cars around him were moving discreetly into other lanes and going around. State troopers are so damned sneaky, tho...

Idiots Ch. 02

by lessthanperfect on Sep 14, 2017
Gay Male

I got bored again. This is the unplanned addition to what was supposed to be a one off. There is one more chapter after this one, which will contain a sex scene for all you horny people. Enjoy. Comments are appreciated. **** "So..." "Martin, don't start this early in the morning." "It's 01:00. We've been on shift for seven hours." "It's technically tomo...

Prison Life Ch. 01

by Alwaysdebating on Sep 14, 2017
Gay Male

The following is my first story it is all fiction. I might put a part 2 if there's interest in it. Sorry in advance for the grammar mistakes. I'm not the best at writing. Please give me constructive criticism if you have any. Enjoy * Steven was your average college kid. He went to parties did good at school and was super involved on campus. He had always d...

Rough Riding to BARUF Ch. 03

by sr71plt on Aug 18, 2017
Gay Male

Exhausted and trying to escape the pain and this filthy cell, I forced myself into sleep. I was wedged in a sitting position on the bench, handcuffed to the jail cage bars and propped on one butt cheek to relieve the pressure on my ass. It had been a truly rough ride, but it had really hit the spot. I was aroused and satisfied as I never had been before, and...

Swift Sword of Justice

by KeithD on Aug 18, 2017
Gay Male

Judge Thomas Oakley slowed the car as he crossed Martin Luther Key Street on St. Catherine where it turned into Jefferson. He often slowed down here, in passing the King's Tavern Lounge—although he'd never gotten up the gumption to go in there. It was too close to home and he was too well known. When he wanted that scene, he didn't go anywhere here in Natche...

Clayton's Available Ass

by Boxlicker101 on Sep 14, 2017
Gay Male

Clayton Smithers sat in his jail cell wishing to God he had never tried the scam. At first it had worked fine; the diploma mill had sold him the diploma and arranged what looked like good references, even responding with glowing letters of praise if anybody ever asked about the qualifications of Doctor Clayton Smithers. It had been a sweet deal with money co...

Pineapples & Chocolate

by emlynley on Aug 18, 2017
Gay Male

Ben sighed impatiently as he wheeled his shopping cart around the small grocery store around the corner from his apartment. He tossed a few random items into his cart, eyes constantly scanning, taking in everything--and everyone--around him. He needed something to satisfy his craving. Nothing in his cart. He was hungry, but it wasn't for food. Instead, he w...

Bio of a Bully Ch. 7 Pt. 2

by ozeboi69 on Sep 25, 2017
Gay Male

With additional editing and ideas by The Pecman The fat fuck was all over me, holding me to the bed and running his tongue up and down my torso, his stinking fuckin’ breath choking me every time he came near my face. I tried calling out, but he knew it was coming and slapped a hand over my mouth. “Now you listen good, punk,” he hissed in my ear. “You ma...