Jail Stories

11,167 results
Orientation
Length
Source
Infinite Scroll

Prison Gang Bang

by TwistMyVanilla on Sep 15, 2017
BDSM

PART ONE: In an alternate universe, Nate's charges weren't dropped. His lawyer advised him to stop fighting and take the plea. In that alternate universe, Nate reported to prison to serve out his two-year term (carefully negotiated, the sentence was much lower than it could have been and his taking it avoided the risk of a jury proving him guilty and send...

One Special Spring Day Pt. 04

by Connie_Ann on Sep 16, 2017
BDSM

Ratman39 provided proofreading and editing of this story. Thank you, Ratman39 - you totally rock! ***** Bonnie begins to awaken with her legs still resting in the stirrups, and she feels something soft rubbing on her inner right thigh. "Bonnie, wake up, can you hear me Bonnie?" She hears a voice talking to her, and realizes it is her hand that Bonnie feel...

First Day Out of Jail

by badblackbluegrassbbw on Sep 11, 2017
Interracial Love

A few weeks after I turned 37, I was at a weed party in a rural part of southern Indiana. I was the only non-white person there. The party got busted and but I didn't worry about it. I had been arrested for weed three times before, all in Louisville, and each time got just a fine and probation. And since hubby is rich and I'll never have to work again, that'...

To Tease a Perv Ch. 04

by Neverlander on Oct 12, 2020
Fetish

"Look," said Rachel. "This one is close!" It was the next day, Saturday. Celine had gone over to Rachel's house and together they were going through the sexual registry, looking for men who might live near them. "He looks kind of weird," Celine said. "And look, it says he was convicted of assault, lots of times." "Yeah, I suppose," Rachel agreed. "Most...

A Ticket to Lust Ch. 01

by rgjohn on Sep 15, 2017
Illustrated

Note: This is an interracial/slut wife story. For those that do not care for that genre, I would suggest you pass on this one. Just trying to avoid the flames from those that do not enjoy that type of story line. * It was after two in the morning and Vicki Larson was feeling no pain as she flew down the highway at over eighty miles an hour. She ignored the...

Brian's Sleepwalking Adventure Pt. 08

by SirBosk1 on Sep 15, 2017
Novels and Novellas

This story contains scenes of spanking, forced homosexuality and oral sex as well as other erotic themes involving adult men of college age or older. If such subjects are offensive, uninteresting or if you are a minor (i.e., child) please leave now. All persons, names, places, events, and descriptions, are purely fictional. Any resemblance to actual persons,...

Jailed

by amyyum on Sep 24, 2019
Loving Wives

The story of my life – I'll call myself "Alicia Moore," not my real name – since I turned 19 is proof that truth is stranger than fiction. Undoubtedly part of the bad things that happened to me were due to the fact that at 19 I was a completely confrontation-averse person who had led a sheltered life, and maybe could even be described as a milquetoast; but m...

Hard Time

by Dr. Bull on Sep 17, 2017
Erotic Couplings

I was doing thirty days on a bogus DWUI charge at the local county jail. I was there about a week when they moved me back to the trustee section. No big deal washing dishes, laundry, mopping some floors and what ever else the guards needed. I'd been there before and they like me, so I get moved back to work. The guys had all been there a few years, but since...

Hard Action

by Winterfrog on Sep 17, 2017
Loving Wives

Many Thanks to Dennis for editing this story. * It was a sad day for me when my best friend in our area of a small Scandinavian town, Jerry Bergman and his wife Christine hosted a goodbye party in his house. Both Jerry and his wife had got new and better paid jobs in a larger town about 350 kilometers away. Of course we were happy for them and knew that w...

The Craigslist Killer Pt. 04

by thrillerauthor on Sep 14, 2017
Transsexuals & Crossdressers

© 2014 by Thrillerauthor * That night was like something out of a horror movie - the most horrendous experience of my life, and that includes Gregg's attempt to murder me. It began with the cops whisking me out of Morton's through the kitchen door, so I didn't even have a chance to tell Ron what was happening. I was worried sick about what he must be thin...