Jail Stories

11,167 results
Orientation
Length
Source
Infinite Scroll

A Peek from the Hedgerow

by Decayed Angel on Sep 15, 2017
Illustrated

Yes it was the hearty mead that set me out that night chasing the ladies that should not be chased, but yea I drank too much and decided to peek beyond the bargirls and whores here in the bar. So I left my friends behind and walked the cobbled streets into the neighborhoods where the women weren't bought by the hour and the gentlemen were just that, gentleme...

Those Who Cuckold Get Paid Back Ch. 02

by Winterfrog on Sep 15, 2017
Loving Wives

Many thanks to ReneeandKent for their editing of this story. * As you might remember, the first part of this story ended with me having only one-day left of my time as a 'jailbird'. It had been a very interesting and useful experience that I never would regret. But today was the great day to be a free man again. My wife had told me that she was too busy i...

Island Adventure

by zack_w on Sep 13, 2017
BDSM

Carol Simony, CEO of the Choplet-LaSalle Corporation and the richest woman in the USA, strode out of the Manila office building and across the sidewalk inside a wedge formed by her bodyguards; she ignored the cries of protest from the pedestrians who were jostled out of the way by her phalanx of thugs. So sure was she that her limo would be waiting that she...

Brian's Sleepwalking Adventure Pt. 07

by SirBosk1 on Sep 15, 2017
Novels and Novellas

This story is based on what may be an urban myth from my college days. A fraternity brother told me about the incident after my own adventure, described in my story "Pledge Class Payback" so I believe it to be true. When I asked about it, no one could remember the actual names or years or the fraternity. However, it fed my imagination and inspired me to writ...

Monopoly with a Twist

by Slydawg on Sep 14, 2017
Loving Wives

What started out as a normal night hanging with friends turned into one of the most memorable nights ever. We had all been drinking as usual, wine coolers, Jell-O shooters, mudslides whatever was in the house that had alcohol in it we drank. About 9pm everyone was feeling pretty good and that is when the fun started to happen. we had been playing cards and m...

The Ring of Ultimate Evil

by Robopoop on Jul 28, 2019
Fantasy

Ethan J. Morrison was a 40 year old loser with an ugly mug, stocky build and an obnoxious self entitled attitude. Everywhere he went and everything he did was an insult to normal society, leaving him with no friends, plenty of enemies and a lot of angry faces wherever he decides to go. He lies, steals, cheats and molests his way to shameless self gratificati...

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Cloudy Waters Mansion Pt. 06

by ddffdd on Oct 20, 2020
NonHuman

| Chapter 16 -- Colorblind & Camouflaged | Meanwhile, somewhere else in the building, Roc had also woken up. The chameleon wandered through his jail room before also opening his closet. The first thing he noticed was the metronome, standing in the center of the closet obviously waiting to be found. He grabbed it out of the closet and stared at it for a...

Adventures of the Silver Wolves

by theblueblue on Jul 4, 2004
Fantasy

Lance stared at the ceiling above him. He was once again in the Forestgrove jail. He had been in and out so often that he had his own cell that they reserved especially for him. He never did anything over the edge like murder or steal. He just got a little unruly when he had a little too much to drink and they would take him to the jail until he sobered up....

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Cock Sucking Jail Whore

by RobinTVDaniels on Sep 15, 2017
Transsexuals & Crossdressers

I've always known that I was not meant to be a guy. Being sexual curious I would look at porn mags like any one does. At first it was just magazines with pictures of naked woment. It was when I ran across my first Hustler magazine that my life was changed forever. Seeing pictures of studly guys with big hard dicks and women on their knees about to suck or be...

Nice Guy Pt. 02

by Katmai on Sep 13, 2017
Loving Wives

Chapter 6: Waiting The next two months were routine. The weather shifted into fall, and we had our first hard frost. I was transferring dead plants to the compost pile one evening, and our female border collie, Star, escaped the yard. She ran into the road, and she was hit and killed by a car. Star died instantly. The driver was apologetic; it wasn't his fa...