Jail Stories

11,167 results
Orientation
Length
Source
Infinite Scroll

Cuff Me Leland

by touche on Sep 12, 2017
Celebrities & Fan Fiction

This story was written without the knowledge or consent of Leland Chapman, no offense or harm is meant to him. That said, please enjoy! -------------------------------------------------- "Hey baby! How's it?" I called out from the kitchen as I heard Leland come through the front door. "You thirsty?" "Fine. Yeah, toss me a water will ya?" He replied gruffl...

Lindsay Lohan's Arrest

by Gudzinya on Sep 13, 2017
Celebrities & Fan Fiction

Officer Mike Miller pulled his police car to the curb and parked in the street in front of the jewelry store in West L.A. Several reporters and photographers were already crowded in front of the store. He turned off the car and stepped out and made his way to the door of the store. He was barraged with questions from reporters and photographers were busy sna...

Grey Sky Ch. 01

by Sonic_the_fox on Sep 14, 2017
NonHuman

Shaking her head groggily, Lily fought to hold onto the darkness. She was having a nice dream; Strong, firm legs pressing open her thighs; The overwhelming smell of masculinity and pine trees; Teeth lightly grazing the tender flesh of her neck then tracing a trail down towards her pert nipple. This was pleasant enough, but Lily wanted more. She wanted this...

The Soldier's Wife

by TRYTSTYN on Dec 31, 2018
Loving Wives

The Soldier's Wife. Just a quick flash story for fun. This is a new attempt at writing for me in a different style told from the point of view of the wife. A poor, defenseless, soldier's wife who is being blackmailed into sex at the office. All the usual restrictions apply. Copyright 2018 all rights reserved to me. No sex in this one as usual I don't do sex...

Jailed Cuckold & Bullied BETA Son

by I_Love_MILF on Jan 16, 2019
Loving Wives

Editor's note: this story contains scenes of incest or incest content. ***** There's something quite humbling about being humiliated by your best friend and his younger brother while getting laughed at by your MILF stepmom. Laryssa is my stepmom. She's only a few years older than me, as my dad loves younger women. With dad in jail for tax evasion, she and...

Imprisoned by My Fantasy Ch. 02

by Jemina004 on Sep 14, 2017
Transsexuals & Crossdressers

Two years ago, if you told me that I would be standing on a darkened street corner in stiletto pumps, fishnet stockings, a black miniskirt, a see-through mesh top, with a black bra and neon pink panties on, I would have laughed at the image. Of course, back then it would have looked ridiculous on me. But on my new 131 pound hairless body, the outrageously s...

Jail Bait

by bigcarl796 on Sep 1, 2017
Erotic Couplings

Patty and Bobby felt like intruders and out of place with all these teenagers. Everywhere they looked, all they could see were high school kids making out and sneaking feels of each other. Finally Bobby said," Patty I've had enough of all this kid stuff; I'm going home," then he asked her," Do you want to have dinner with me tomorrow night?" Patty replied,...

Two By Four Marriage Therapy

by Skippy47 on Dec 14, 2020
Loving Wives

Author's note: Many stories published in Literotica require a good bit of suspension of disbelief in order to be enjoyed. It is incumbent on the author to provide enough 'true' elements so that the plot can has enough plausibility to keep the reader from giving up on it. This is one such story. As always, I hope you enjoy. "Archer, get me another drink and...

When We Were Married Ch. 06C

by DanielQSteele1 on Sep 18, 2017
Loving Wives

© Daniel Quentin Steele 2011 #################### THE CLEAN UP CREW -- SECRETS Here's the latest chapter of WWWM. My thanks once again to Curiousss for his hard work on editing, which I definitely think has improved the story. Believe it or not, the next chapter will not be long in coming. It's already written and Curiousss is laboring on it as this is p...

Twisted Sister

by WantonWench on Sep 16, 2017
BDSM

He walked into my dungeon and knelt. His eyes looked through my boots, but didn't see the polished leather. I hate it when they came to me like this, filled with defeat instead of submission. I used the pointed toe of one boot to lift his chin. It was a moment longer before his eyes also lifted. Whatever it was, this boy had it bad. He'd spill it to me soon...