Gay Jail Stories

582 results
Orientation
Length
Source
Infinite Scroll

Hotel - Room 617

by perihelion on Sep 1, 2017
Gay Male

I was playing around and cooling off in the surf from an intense pickup beach volleyball game. It was hot as hell and there seemed to be a thousand people on the beach and in the water. In the holiday spirit most people are nice and fun to be around so I enjoy the time I spend in the Gulf waters. I swim almost every day of the year in balmy Florida, even the...

Road Side Assistance Pt. 02

by rimaday on Nov 25, 2017
Gay Male

Still, dazed and confused decided it would be best to head back home. By the time I would get to the nursing home to see my mother, I would have to turn right around and head back. I would need to stop somewhere and clean myself up. I can't remember the last time I shot a load with that much force. It was hard to tell where it all landed using a rear view mi...

Sentenced to the Church Youth Group

by timmywells on Aug 18, 2017
Gay Male

A tale about Jimmy, a teenager in West Albany, New York circa 1977... **** After barely graduating high school in 1977, I was finally beginning to learn why paying attention in school might have been a good idea, because I had been unable to gain admittance to either of the 2 local community colleges because of my poor grades. That was embarrassing, espec...

Dreams Sometimes Do Come True

by oral454younger on Aug 18, 2017
Gay Male

Shawn strapped on his gear and prepared himself for another patrol in one of the most dangerous cities in the United States. Standing a whopping 6'5" and weighing a chiseled 275 pounds, citizens and hoodlums alike all new Shawn very well. On the mean streets, his nickname was "Big Jack." Even his fellow officers looked up to him as well. When they got a roug...

Coming Home: Davis Brothers Ch. 06

by robcub32 on Sep 25, 2017
Gay Male

Ben flexed his right arm at the elbow, glad to finally have the cast gone. He was over the moon at being able to use both of his hands now. He was finally back to work, driving a truck at Ace. Even though he was temporarily off the rotation for long hauls, that was fine with Ben. He could do the local transports just fine, and it kept him home with Benji. Al...

Between the Bars Pt. 02

by carsonshepherd on Sep 25, 2017
Gay Male

Chapter 6 You've got to be fucking kidding me. I stared at Daniel in disbelief. "Uh, I don't think so." "I wish I didn't have to get you involved in this, but it's the only feasible way for me to get to Birmingham right now. I had to leave my Jeep in Tallahassee. I couldn't go home to get it. An airplane is totally out and I can't risk being recognized on...

A Boy Who Came In from the Cold Ch. 17

by SadieRose on Apr 3, 2019
Gay Male

Chapter 17: When All Else Fails... © Sadie Rose Bermingham 2006 "Apologies for the delay to this chapter. My internet connection and my husband have both been sick and it's taken me a little while to get around to posting. Anyway, I hope you enjoy the penultimate chapter of Rayne's French adventure." The usual terms apply. Copyright belongs to Sadie Rose...

Underwear Ch. 04

by SadieRose on Apr 3, 2019
Gay Male

PART FOUR -- UNDENIABLE "It's been a while since I added to this Vampire story arc. A Boy Who... kind of took me away from it but rest assured Rayne and Kevan have not been forgotten. This is quite a difficult storyline to work with as it will tackle Rayne's own personal issues with abuse head on but he is an older and stronger character than he was during...

You Get What You Paid For Ch. 03

by ruetheben on Aug 21, 2019
Gay Male

Adam holds the die in his hands, shaking them repeatedly as he closes his eyes. "C'mon, baby, gimme a five," he begs before tossing them on the board. He looks distraught, and I just laugh at the snake eye's he just rolled. "Are you fucking kidding?" "Maybe this just isn't your game," I tease, scooping up the dice to take my turn. "This is rigged," he sugg...

Sporting Chance

by perihelion on Aug 30, 2017
Gay Male

Two hours after the school board hired me, I sat with my new principal in his office. "Jeremy, I'm glad you decided to call me. I just wish you'd done it sooner so we could talk." "It's like I said, no point in bothering you until I completed the courses I needed to teach in Georgia. I still don't understand why I had to take those extra classes if I didn'...