Jail Stories

11,167 results
Orientation
Length
Source
Infinite Scroll

Dare To Be Different

by Bill Smith on Oct 15, 2017
Exhibitionist & Voyeur

I can't believe I'm doing this. I know we are both going to end up in jail. Why did I take this dare? God I feel so stupid and scared. Oh God don't let me end up in a jail cell with someone with the name of Bubba! You look so cool just sitting next to me. I know that you have nothing on underneath your trench coat. You see me looking at you and you smile th...

Female Criminals

by Samuelx on Sep 1, 2017
Erotic Couplings

Lily Stone stood in her cell. Inside the largest women's prison of the state of Massachusetts, she was known as the Butch Brawler. All the other female inmates feared her, and with reason. This six-foot-two, 250-pound black woman was once a member of a ferocious gang from Dorchester. In the streets, she had a reputation as a fierce fighter and a deadly hustl...

The Predator Ch. 25

by D.C. Roi on Sep 26, 2017
Novels and Novellas

"That Ott guy you busted the other day wants to talk to you," a sheriff's deputy from the jail detail told Tim Jackman on the phone. "He says he knows stuff about some other crimes and wants to make a deal." It was almost end of shift, and Tim had been looking forward to going home and spending a quiet evening with his wife, Lynn. It didn't look like that w...

Game Night

by Ravlicious on Sep 14, 2017
First Time

David rolled the dice and snake-eyes came up. He moved his race car token to St. James Place and put $180 into the bank for the deed. He and his best friend, Samantha, hadn't had a game night with just the two of them in over a year. In high school, it had been a weekly tradition, either on Friday or Saturday night. Ever since college started, though they sa...

Sex on the Roof

by Middleagepoet on Sep 16, 2017
Letters & Transcripts

December 29, 2009 Manager The Roof Bar 2654 Richmond Dallas, Texas 75205 Re: Your Advertisement in the Dallas Digest Magazine To Whom It May Concern: I am currently writing from the county jail to lodge my formal complaint regarding your advertisement in the most recent edition of Dallas Digest Magazine. The ad I am referring to is the one titled "The...

Wino

by Boxlicker101 on Sep 16, 2017
Non-Erotic

"Brothers and sisters, Hell is growing. Hell is growing by leaps and bounds..." the preacher's voice droned on. Paul sat as far back as he could, wishing the asshole would shut up so he could get the bowl of soup that he had come there for and he could join his buddies drinking wine in the park a few blocks away. "I wish I didn't need to eat so I wouldn't h...

Jail

by cinnamon_kitten on Sep 13, 2017
Erotic Couplings

The door closes behind me and I walk over to the bars. You are sat in the Jail room and look up at me. I smile and reach my hands out to you through the bars. You take them into your hands and I can feel how cold they are. "What an ending to a fantastic evening," I say. You look down and mumble something that sounds like sorry. I let my hand go up to your...

Lady In The House Ch. 01

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

How had it come to this? I was dressed as a woman and standing in the far corner of a darkened cell on E Block of Chelmsford Correction Facility for Men, and waiting for the most dangerous inmate in the jail. How had a mild mannered, and diminutive but highly successful accountant in his 30s ended up in one the States high security prison? Well it had a lo...

Winona Does Her Duty Ch. 01

by Kettle Corn on Sep 17, 2017
Celebrities & Fan Fiction

Why did I do it…? Winona thought in her sad state, what was so special about those shoes? Winona was morbidly depressed. She was not allowed to leave her house just in case she might flee. I would do anything to not go to jail, anything. "Why me?" Winona interrupted her train of thought with a simple statement of anguish and sorrow. It was about 9:00...

I Shouldn't Have Done That

by Nelsonnn on Sep 12, 2017
Erotic Couplings

Disclaimer: This is a fairly long story, with bouts of descriptive sex. If you're looking for a quick read, look elsewhere. Otherwise, enjoy the story. ***** I awoke to the sweet familiar scent of my husband. Only my husband has been in jail for a few months now. As I woke up more fully and rubbed my eyes, I looked around my dark room. Light was starti...