Jail Stories

11,235 results
Orientation
Length
Source
Infinite Scroll

Alice is Arrested and Goes to Jail

by sissymaidallyson on Sep 14, 2017
Fetish

Alice was a straight A student and was a total goody two shoes. She wasn't ugly but she certainly wasn't cheerleader material but was generally liked and respected by her peers and teachers at her high school. She lived in a relatively small town on the outskirts of Jackson Mississippi and was a happy child. She wanted to experience everything life had to of...

A Family Coerced Together

by Gulliver on Sep 16, 2017
Loving Wives

This is the beginning of what I anticipate will be a long series. This first chapter is just a teaser. Please feel free to e-mail me with any suggestions you may have with regard to activities etc you would like to see in future episodes. Don Bunt's hands shook as he once again read the memo he had received from his boss, Bill Trigg, a few minutes earlier....

Bitch Cop Traffic Stop

by dannythebaltimoron on Sep 17, 2017
BDSM

I Fought The Law, and We Both Won...Sort Of... (c)2012 Daniel deLaire It's about 8:30 on a Thursday morning, and I am driving along the back roads, away from the highway with the others making their way to wherever it is they're off to. Most of them are headed to work. I am not. I work long, hard nights at the Kwik Mart near my house so my day, thankfully,...

The First Encounter

by techsan on Sep 13, 2017
Erotic Couplings

Authors' Note: The following is a narrative of a purely fictitious encounter ... we think. The authors have used their user ID's for the Literotica site but there is no proof that the events of this narrative actually occurred ... or not. Use your imagination, dear reader, and decide for yourself what's real. Techsan: We had met online at an adult website...

Balls and Penis Jail

by diana_phlp on Sep 17, 2017
BDSM

Author's Notes: This is the first time I am publishing a story. It is a fully imaginary story and all characters engaging in sexual relationships or activities are 18 years old or older. As a reader, you also should be 18 or more and if you are not hard or wet after reading this story, something may be wrong. ******************************** Balls and P...

The Happiest Anniversary

by dannythebaltimoron on Aug 31, 2017
Fetish

It's 7:30 on Friday night, in one of the last of the Golden Days of the 1990's, and I'm sitting at an upscale lounge. The lounge is in a shopping center that I hate going to. Just ten years ago, the whole area was a field that my friends and me used to play in, and there wasn't much in the area. Today, it is an over-glamorized bastion of overpriced plastic m...

The Fallen Elitist

by dannythebaltimoron on Mar 21, 2018
BDSM

The Fallen Elitist Or It Never Happened © 2018 Daniel de Laire It had been a long day already. She was a 33-year-old urban professional; what they called a "yuppie" in her parent's generation. The daughter of blue collar parents who wanted a white collar for their little girl. But she wore a black collar under her frilly white one and it, like her, belon...

Jailhouse Faggot

by nancyvasquez on Oct 14, 2017
Anal

Before I got sent to the joint I spent over 6 months in county jail. The jail was old and they had old fashioned cells with bars. The cells were small, 4 bunks in each cell. I had never been in jail before and I was scared and it showed. I was young, slightly built, and timid as hell. The cellblock I was housed in was on the 4th floor. There were two sides...

Staying Out Of Jail

by JackStark on Sep 12, 2017
BDSM

"I told you last time if I saw you around here again, I would take you in. Now up against the car, spread your legs and put your hands behind your back. Looks like you have done this a few times. I need to cuff you and frisk you, understood?...Understood?" "Yes Sir." "Good girl, that's more like it." I cuff you and proceed to pat you down making sure to ru...

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...