Jail Stories

9,626 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...

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21st Century Slave Ch. 01

by Ciceri on Sep 11, 2017
NonConsent/Reluctance

Three years ago I was to join my wife, Mari for a week on her business trip to Yemen. She owns an antique store here in Portland and often travels in order to procure items of antiquity from afar. My work prevents me from being gone for weeks at a time but I agreed to fly to Yemen once Mari was done visiting Turkey. After several transfers and many hours i...

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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...

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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...

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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...

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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...

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Revenge Can Be Very Sweet

by Fred1177 on Sep 16, 2017
NonConsent/Reluctance

Janet and Charlotte never got along together. They worked at the same company and even lived across the street from each other. They avoided each other because they'd already had a couple of public confrontations and neither one wanted a repeat. All of that made it a very unusual thing for Janet to receive a phone call from her hated rival. "Why are you cal...

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Plea Bargain

by Gaius8666 on Sep 15, 2017
NonConsent/Reluctance

I still can't believe I had been so stupid. As part of my fraternity initiation, my task was to break into the Alpha Omega Psi sorority house, take some pictures of the girls naked in the shower and then return to the frat house by morning. Sadly, not only did I not get any pictures, and therefore was not allowed to join the frat, but I was caught and charge...

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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...

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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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