Gay Jail Stories

582 results
Orientation
Length
Source
Infinite Scroll

A Rape in the Belfry Ch. 05

by Decayed Angel on Sep 16, 2017
Gay Male

I have to admit, my lawyer was very apologetic and accompanied me while I was transported from the jail to the state penitentiary. I'm not sure how he was able to do it, but he went as far as the main entry gate, where I climbed out of the van and was walked though a gate. My lawyer talked for nearly the entire ride, either apologizing or laying out his str...

A Rape in the Belfry Ch. 08

by Decayed Angel on Sep 16, 2017
Gay Male

Surprisingly, it wasn't too long before Rocco and I did get out. Somehow our lawyer pulled it all together and got a court date set for me as well as one for Rocco about a week later. Rocco had threatened to twist our lawyer's tiny little head off if he engaged in cyber sex with anyone, much less the judge's wife, in the days before our court dates. The law...

Pile of Mattresses

by Boxlicker101 on Aug 18, 2017
Gay Male

It was the summer of 1975 and Curtis Holt was not happy to be doing a sixty-day sentence in the county jail for possession of marijuana, although he knew things could be worse. For one thing, he was aware there were plenty of men doing far longer stretches, and they would have gotten extremely horny, which should have greatly interested him. For another, he...

Technical Difficulties Episode 08

by LucyH on Sep 14, 2017
Gay Male

Fall 2005 Zach held the door for Ryan as they stepped out of the bail bondsman's dingy office. "I like the Bikers for Boobs breast cancer poster." "Sorry, I know this probably isn't how you wanted to spend your reading break." It was just like his sister Amy to call and ask him to bail her out when he was in the middle of having his own crisis. They'd been...

The Effects of Drunken Driving

by bi_indiana_chub on Aug 18, 2017
Gay Male

"Ma'am, can you step out of the vehicle." My wife looked at him with what I'm sure was the most drunken look he had ever seen, but I might be wrong. We hadn't been going that fast and I was pretty sure that we had been staying between the lines, but being half drunk myself, I didn't help. She turned to me and even with the drunken stupor, anger was written a...

Nephlim World Saga: Wigging Out

by Nephlim14 on Aug 30, 2017
Gay Male

Setting: Prison P.S. This story is meant to inspire stories of a similar setting. If anyone decides to write stories like this, please reply on my page. Thank you. ***** Yo dogs! My name is Victor, but my homies call me Viking. HaHA! But seriously, my name is Victor and before you get the wrong idea, I am NOT a black gangster. I'm Caucasian and I come fro...

Tricked

by HuckPilgrim on Sep 14, 2017
Gay Male

Jimmy Manley shares the cramped backseat of a Volkswagen with two men that he does not know. Roger Bones sits up front, in the passenger seat. The man sitting next to Jimmy slips his hand onto Jimmy's thigh. Jimmy's body goes tense, but he tries his best to act natural. Jesus, not here, he thinks. Not now. He twists his lean frame, trying to protect his mi...

He-wolf Ch. 06

by lonleylucas on Sep 14, 2017
Gay Male

Disclaimer: All characters involved in sexual relationships are over 18 years of age, and no minors are sexually exploited in this content. In no way are actual events or persons depicted. This is my own fictional story and my characters mine and my own if you want to get to know me add me on skype always happy to have more friends allen9980) Alex-18 werewo...

Bus Stop Blowjob

by kneelsoften on Apr 3, 2019
Gay Male

I was returning home from spring break. Some friends hurriedly dropped me off at the bus station in the middle of northern New Jersey, anxious to get back to the party they just left. I was a little drunk and stoned, and realized, after checking the posted bus schedule in the semi-darkness, that I really screwed up. The bus wasn't due for another two hours....

Yellow Ch. 05

by ElonaHunter on Aug 18, 2017
Gay Male

"I will kill you." The unmistakable sound of a shot gun being cocked rang through the small room. "You don't have it in you." I shot up in bed, breathing hard. I glanced around, still dazed from sleep and my eyes landed on Reed. Resting peacefully, he had a small smile on his perfect face, right next to me. Something about seeing that, a thing I usually...