Sissy Jail Stories

17,389 results
Orientation
Length
Source
Infinite Scroll

Was He Guilty? Ch. 04

by DG Hear on Sep 14, 2017
Loving Wives

Please read the previous chapters to make it easier to follow the story. Also a big thank you to Estragon for editing this story. Chapter 4 As I have mentioned before, I'm a writer, Joe Baker. I got permission to write Jeff Johnson's side of the brutal murder of three men. I will be telling excerpts from the prosecutor's side, and Jeff will tell me where...

Fuzzy Flight Pt. 04

by MarcusWoolf on Sep 14, 2017
Fetish

My room was bright and spacious and in addition to my bed and a cupboard also contained a writing desk that I could use for my studies. I lived in great comfort compared to most of my fellow students. My mature landlady was very supportive and encouraged me to take my studies seriously. It was a bit strange to share a flat with mature woman who in many ways...

A Visit Home

by ZukoBaratheon on Sep 14, 2017
Erotic Couplings

The engine of his brother's old 1970 Chevelle cut off as Raymond removed the keys from the ignition. The silence took him by surprise, as it always did when he'd ride in it with Danny when they were younger. He got out of the car, taking note of the stares he got from passers-by in the parking lot as he shut and locked the door. No doubt they were curious as...

The Vicar of St. Dunstan's Ep. 01

by Nigel Debonnaire on Sep 19, 2017
Novels and Novellas

The first of three episodes a new series about Fr. Alfred, Vicar of St. Dunstan's. Categorizing these episodes is tough, since there isn't a "Dramedy" category on this site. Suggestions for future episodes are welcome, if you'd like to see more of Fr. Alfred and his flock. The Quilting Ladies The tri-weekly run ended with a sprint across the high street to...

Hellsgate Prison

by Julie20 on Aug 18, 2017
Fetish

I have referred to some of these events in a previous tale but there is so much more to the Hellsgate Myth that I wanted to revisit it in greater detail. The Hellsgate is a deep fantasy and, being a fantasy, it does not have to be rational or even consistent. Perhaps it is a cipher for that part of me which is normally kept down but whenever I am consumed b...

Janie Learns to Fuck

by LeCoach on Sep 13, 2017
First Time

Janie Walsh was frustrated! She'd been hot for her childhood friend Jeff ever since...forever! But he just treated her like a pal and never quite understood her feeling for him. She needed help. So Janie asked her Mom one day after school about this. "Mom, how do I get a boy to, you know, notice me?" she asked. "Now, who might this be?" Her mother replied....

A Class of Her Own

by LizInTrouble on Sep 17, 2017
Fetish

Rachel knew that her carelessness would be her undoing - it always was, and had been at several previous schools; her inability to keep her legs closed and dress conservatively. And why should she after all? She was 27 and gorgeous; slim, full-figured, with beautiful round breasts and a firm backside, her eyes blue and her hair naturally blonde and accented...

FireBlood Ch. 03

by Duzzel on Sep 15, 2017
Illustrated

* He was having that dream again... the memories of his past flooded through his mind. He was falling, falling fast through the sky, his Dragon form was in tethers, dripping his own blood as he fell. He forced his eyes open to try and get his barring straight on his location. He knew the green hills immediately and he groaned. As if he wasn't screwed enough...

Two Dreams Ch. 04-05

by victoriawhita on Sep 15, 2017
Romance

Chapter Four ***Shasta felt like a giddy middle schooler with her first guy. David was so much better looking, and a better kisser than...what was his name...oh yes, Shwartz. Back then she thought it didn't get any better than shy, sweet Shwartz. She was glad she hadn't held onto that belief too long. She floated back to her desk, all smiles. If she kept th...

Unexpected Guest Ch. 10

by Ada Stuart on Sep 26, 2017
Romance

Jared watched as Ann did her best to ignore him after their dinner conversation. She was being so causal about the whole thing that it was clear that she hadn't any deeper feelings for him. He felt as if the walls of the cabin were closing in on him, smothering him. He needed some fresh air, he thought and he jumped up so quickly that his chair scraped along...