Gay Jail Stories

582 results
Orientation
Length
Source
Infinite Scroll

My Angry Tenants Ch. 03

by rae121452 on Sep 25, 2017
Gay Male

After Ron and Gary had been living downstairs and fucking the snot out of me at every occasion for several months, they came to me one day to ask a favor. Apparently, they had run into difficulties with their parole officer and wanted me to meet with him and try to smooth things over. The alternative was, they both go back to prison and I get no more cock, s...

The Botany Professor Ch. 04

by Coxswain on Aug 30, 2017
Gay Male

In revenge for my son, I regain my top-hood * Coach Kaugman pounded on the door (interrupting my first foursome with my wife, her father, and my father) to warn me about my son Bobby. "He's at a football team party, and it's getting wild." He drove me over to the motel room site of the student whoopee, and indeed it had become a "drunken debauch." Naked c...

Jason's Trip to Mexico Ch. 05

by beefylatn on Sep 25, 2017
Gay Male

Jason's revenge Jason eventually heard keys jangling and the cell door opening as he sat up to see El Capitán opening the door and Juan standing there with a concerned look on his face. "Dios Mio, Señor Jason are you all right?!" exclaimed Juan as he rushed over to help Jason stand from the cot. Jason was never so happy to see anyone in his life as he follo...

Of Mice and Men Ch. 01

by Gweall on Sep 14, 2017
Gay Male

Alright Ladies and Gents.... we (well, mostly me... because I love this story! Lol!) wanted to post another infected story!!! It is a continuation, but can stand alone if you've never read 'Wing of Grey' or 'Things Change'. Hope you all love it as much as I do! We had so much fun working on this one :) Also, just because people seem to be getting confused,...

Al's One Night

by JimBob44 on Sep 14, 2017
Gay Male

*Author's Note: Any and all persons engaging in any sexual activity are at least eighteen years of age. **Author's Note: This is a flash story; not meant to be taken too seriously. *.*.* Ronnie Valpo entered Tommy's Po-Boys and sauntered up to the counter. "Help you?" the young man behind the counter smiled. "Regular roast beef, just gravy," Ronnie smil...

I Saw Daddy Blowing Santa Claus

by andtheend on Aug 18, 2017
Gay Male

Son sees his father having gay sex with Santa Claus. Because of what I saw Christmas morning, now every time I hear, I Saw Mommy Kissing Santa Claus, I substitute Daddy for Mommy and kissing with blowing. That song has new meaning for me, after I saw my Dad blowing Santa Claus. A true vindication, it was shocking, revealing, and comical. Let me start from t...

The Way You Say My Name Ch. 10

by wavyscribe on Sep 25, 2017
Gay Male

“Jamie, the guy’s a drunk on his way to the pen for God knows how long. He’s bound to be lying to save his own ass.” “Why now, though? He’s already taken the deal. He’s just waiting for the judge to impose sentence. What could he possibly have to gain by making up this story?” Dillon waited until the doors closed and then pressed the button for the sixth f...

Letting Him Down Easy Pt. 01

by vikkihawe000 on Nov 18, 2019
Gay Male

Hello, dear readers. This is part 1 of a likely 3 volume story. Working on part 2, though not sure if the precise direction yet. If anyone has ideas, let me know in comments! xx Vi ~~~ Jessy laid in the arms of her lover and smiled as she always did after sex. Even though she was only in her late 20s, she thought her days of wild, passionate sex were over...

Aquata Cove Ch. 87

by Feare909 on Sep 14, 2017
Gay Male

Chapter 87: Putting Things Right Merrick loving kisses Adam's lips, before he sits back up. The spoon clinks in the small bowl he holds, before he turns to set it next to the ceramic deep dish containing the rest of the soup. He gets up, and turns around, smiling as he sees the paper fish cards taped up on the wall. He puts his hand onto one of them, openin...

A Miserable Pile of Secrets Ch. 09

by DreamerByTheDiamonds on Apr 10, 2019
Gay Male

Arthur's mother was a wild but gentle woman named Brenda. He called her Mama. She lifted weights and ran on a treadmill when she had the time, but she was still a gently plump woman. She had glossy French manicures, cute summer dresses, curly blonde hair, and the ability to weld. Her husband, Arthur's father, was Dustin, also known as Daddy. He was very prac...