Gay Jail Bitch Stories

576 results
Orientation
Length
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Infinite Scroll

Taken by My Boy

by Coxswain on Sep 14, 2017
Gay Male

Man attacked by thugs finds his son one of them * This is a true story, as told to me by a friend. Names have been changed to protect identities. I was about to retire. A couple more years. I was looking forward to it. I was getting tired of teaching. I coached the sports teams and taught physical training at Obaledi College. I had a favorable rating--los...

Jail Bite Ch. 03

by silverangel621 on Sep 25, 2017
Gay Male

Hello again. I'm slowly updating so be assured I will finish at least Golded in Gold (for those of you that came over from that story to here) one more chapter for this story to go. Percy woke to the chipper tweets of birds heralding in a new day. Something was tickling his nose and there was something scratchy and warm along his cheek. He was laying on to...

Jail Bite Ch. 02

by silverangel621 on Sep 25, 2017
Gay Male

Hello, all. I know it's been a long time but I'm getting to all my promises lol. I'm not going to lie, I'm mainly updating on another site that I can't name here or this story will never get updated. But this story is on another site under the same title name only with different character names. Anywho, enjoy :). Beta'd by Adrianabelen, whose been with me...

Prison Bitch

by mainsjoseph7 on Sep 5, 2017
Gay Male

How did I end up here? A few hours ago I was in the local gay bar socializing and getting drinks from just about every guy there. Having never been to a gay bar before, I was surprised by all the attention I was getting. My name is Joe, I'm 26 but I look ten years younger than I am. Which trust me can be annoying sometimes. The last thing I remember clearly...

Jail Time Ch. 01

by oralguy82 on Aug 18, 2017
Gay Male

I was spending a couple of weeks in the county jail waiting for trial for a little misunderstanding over the ownership of a car. The first couple of days weren't too bad. There were 16 cells on my floor, and 5 guys serving short time. I was starting to get pretty horny, and that was it easy to take care of, but still not really all that satisfying. I wante...

Jail Time Ch. 02

by oralguy82 on Aug 18, 2017
Gay Male

Before, I had spent 2 weeks in the county jail and, I thought that was all done and gone, and would be forgotten. But about 4 months later, I was almost thinking how can I sign up for another 2 weeks. I felt humiliated about the experience, but so turned on too. More than once I had jerked off to the memory of that humiliation. A 25-year-old man thinking ab...

Bitch

by Frogsoup on Aug 18, 2017
Gay Male

Be careful what you bet. Cody had me; we both knew he did. If I was in his place I'd be merciless. The bet was high stakes; whoever lost had to give the winner whatever he wanted. I thought I'd win. I'd already planned on my winnings: I'd trade cars with him for a week. Cody was in his element in his SUV and I grinned whenever I imagined him in a beat-up Ki...

A Bad Day At The Jail

by sexygirl76 on Sep 19, 2017
Gay Male

This story actually has two different versions: a gay version between two men and a lesbian version between two women. Since there are categories for each, I thought I would write a version for each. This is the gay version. Mark Jenkins lay back on his bunk staring up at the bunk above him. He was working on the second half of a 25-year sentence for killi...

The MP Bitch

by Coxswain on Sep 19, 2017
Gay Male

The MP Bitch Big military cop learns the Army way to protect and serve It all started with Kowalski in 1968, a year before I retired from the Army. One of the men in Sergeant First-Class Kowalski's platoon sent an anonymous note to the Military Police (the MPs) that he was a drug user, and as the senior MP detective, I got the order to shadow SFC Kowalsk...

Becoming His Prison Bitch Pt. 04

by LittleKay on Dec 12, 2018
Gay Male

Love love love feedback, leave comments, leave your love, leave suggestions, leave constructive criticism. Anything unnecessary, nit-picky or rude will be deleted however. ***** Darian looked down at Lexus as he slept and sighed. He probably should have told him. Well, he didn't exactly hide it but... He left the cell when he saw the crowds start to disp...