Sissy Jail Stories

17,389 results
Orientation
Length
Source
Infinite Scroll

Pierced Desperation

by justincbenedict on Sep 25, 2019
BDSM

Ervin felt his cock, bouncing on the leaden testicles, as he got out of his car. It was such a funny old house that Isely lived in... She charged by the hour, claiming on her taxes that she appraised antiques. But her credit card "charger" was next to her bed... It had been quite a week, Ervin reflected as he climbed the steps onto Isely's porch. The Pr...

Making Francesca Ch. 01

by Spango on Sep 12, 2017
Transsexuals & Crossdressers

Author's note: I originally posted this story on another site under the title "Kidnapped and Sissified" a few years ago. I have decided to pull it out, dust it off, do a little editing, slap on a new title that I like better and share it with you fine folks here. Enjoy. Frank was an ordinary guy in his mid-twenties; of average height and build, loved col...

CFNM Adventures in India Ch. 02

by cfnmlover64 on Jul 14, 2020
Exhibitionist & Voyeur

Ramesh had gotten used to being naked around Nanda. It was so freeing, and he liked how he could show off his muscles at any time. It was no longer as exhilarating to show off his body to his sister; it was normal now, even though it had only been a week. His father had died ten years ago, so his mother had been alone for a while. His mother, Dhanya, was 4...

Who Killed Jenny Schecter? Ch. Adden. 1

by OGSalli on Jul 15, 2020
Humor & Satire

DJ La Pica (Carmen Morales) broadcast her first Top 10 Lesbian Country and Western Tunes list near the end of Chapter 34 of Who Killed Jenny Schecter (see below in case you missed them). Without further ado: "Good afternoooooon, San Francisco! This is your besty former convict galpal, Alice Pieszecki, broadcasting live from the Tower of Power here at Stati...

The Cabin Ch. 07

by MaddieKim on Sep 14, 2017
BDSM

This is the final chapter of The Cabin. The story would not have been posted without Kirk2004's editing abilities. Once again, thank you, Kirk. ~*~*~ The Kitten is curious "Admit it, Kit. You're curious. You wonder what it would be like to be tied up and fucked." "I don't..." Kit's fingers went to the scar. Oh hell, Michael thought. She had been tied u...

Owning The Girl Next Door

by Frognut on Sep 11, 2018
Sci-Fi & Fantasy

Chapter 1 The Beginning It started one afternoon after I had gotten off work with my Dad, I was tinkering with my car in the driveway when I hear my name being called. I looked down the street and a friend of mines girlfriend was walking to me, I said hey Sherry what's up? she asked what I was doing tonight? I said going to cruse the beach for a couple...

A Night at Home with Mistress

by Georgie27 on Sep 19, 2017
BDSM

Saturday evening found me in my usual position. I was handcuffed to the radiator in our bedroom, on my hands and knees. My upper body was tightly laced into my red corset, my false boobs filling the bodice. My freshly shaved legs were encased in fishnet stockings. Black spike heeled boots came up to my knees. i was wearing a blonde wig and tarty make-up, inc...

Hate Crimes Inc. Ch. 01

by NOIRTRASH on Sep 16, 2017
Loving Wives

All characters are adults. ***** The first time I collided with Janet Douglas I was in my car parked in a space beside the Come & Go store, with a cup of coffee and a Crispy Cream Donut for supper. Janet strolled over, leaned on the door, and kinda stuck her head and tits in the window. I put down the file I was reading. "Gotta light?" She asked. It was e...

Robin and Jimmy Olsen - Sissies Ch. 05

by tawnysuede on Sep 15, 2017
Celebrities & Fan Fiction

Jamie Olsen hated Mondays, because on Monday morning she had to go back to being boring Jimmy Olsen after having spent all of the weekend as Jamie! Sunday evening had been disappointing. As usual she had been out on her street corner on the stroll. Last night she had chosen to look extra trampy, wearing torn stockings, her five inch heels, and her black lea...

The Dragon Ring Ch. 05

by Beatnic_jazzman on Sep 25, 2017
Sci-Fi & Fantasy

Councillor Cadwill was there already, having arrived minutes in front of us. "The talk is all of Prince Hallit being wrong footed. There are some that want to press forward, take him down a peg, but there are some that worry about reprisals; sabotage of their place men. It's turning into a kerfuffle large enough to attract the vultures of the café commentat...