Sissy Jail Stories

1,000 results
Orientation
Length
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Infinite Scroll

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...

A Sissy Saga Ch. 10

by Snurge on Sep 15, 2017
Novels and Novellas

"Disgusting!" exclaimed Miriam Hancock lightly as she examined the photographs Emma Twist handed her. It had taken Hardwick most of the day to produce the prints, but they were well worth waiting for. The headmistress went through them as if shuffling cards, and having glimpsed each one viewed them a second time, more slowly and with greater concentration. "...

Sissy

by TxRad on Sep 14, 2017
Mature

I came in from work about noon on Friday. I had been gone for a little over two weeks. Pulling in the driveway, I noticed that my daughter's car was gone but her best friend's car was parked in front of the boat on the far side of the carport. You talk about a pair to draw to; those two were it. My daughter is tall, dark, and slender, Sissy is even taller, b...

Sissy School

by zeta515 on Jun 19, 2018
Novels and Novellas

Copyright 2018 by Zeta All rights reserved This story may be freely distributed in electronic form but must include this copyright. Sissy School is a work for pure fiction and all locales, names, characters, places, and incidents are the products of the author's imagination. Any resemblance to actual events, locales, or living persons is entirely coincide...

Sissy and Missy

by ChristopherDB on Feb 12, 2019
BDSM

Copyright 2019 Christopher D.B. * The central vacuum system made barely a sound as I made my way through the apartment. It was spacious and occupied the entire third floor. Although fully furnished and containing some of Countess Tori's personal items, she only stayed here a few nights a week. My feet were hurting, as the toe box on my pumps fit a little...

A Sissy Saga Ch. 05

by Snurge on Sep 15, 2017
Novels and Novellas

Miriam opened the door and poked her head through the gap into her daughters bedroom. "Sorry to call on you at such short notice darling, but the water boiler's buggered and I have no other choice but to ask Hardwick to go and have a look at it. I've no idea how long he's going to be, so could you take his first session?" Jennifer roused herself from the bo...

My Girlfriend's Sissy Roommate Ch. 05

by SEVERUSMAX on Nov 24, 2017
Group Sex

I awoke from my half-drunken sleep to the sound of sex, and God, it was a fantastic noise! I could feel the vibrations on the bed as Larissa rode Rain, plus I could hear her moans as she took him balls deep inside her cunt. She looked at me as she saw me rise, gesturing for something, and sure enough, she wanted it in her ass. It was a dream come true, and I...

Big Black Cock: A Sissy Surprise

by silkstockingslover on Feb 13, 2018
Illustrated

Summary: A wife joins her husband as a slut for a teen BBC. Note: This is a 2018 Valentine's Day story so please vote. Note 2: Thanks to Tex Beethoven, thor_p, Robert and Wayne for editing this story. WARNING: If you hate gay stories, interracial submission, sissification (not a word I know) or cuckolding please don't read. If you do like those themes.....

Teacher Wife Goes Black

by easyballs on Nov 25, 2017
First Time

This story is about a married wife who makes her small dick husband a sissy slave, and eventually finds some real cock to fill what she has been missing but it comes from an unexpected source. If this type of story offends you fuck off and read the beano or something negativity I get daily, so it won't be new to me. ***** As I sit here writing this I am na...

Snowbunnification

on Apr 22, 2025

This is the story of two untalented white rappers who discover that despite their lack of musical ability they have other marketable talents. The rap duo- Romeo Tha Playa- 5'10" thin but with a big ass. Brown hair. He is incredibly insecure about his soft features and tries very hard to act tough. Brandan Guns-Out 5'5" still thin but with a little...