Sissy Jail Stories

17,389 results
Orientation
Length
Source
Infinite Scroll

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.....

Daisy finds Mr. Right Now

by JonThomas_ on Sep 16, 2017
Transsexuals & Crossdressers

I was sitting at the bar drowning my sorrow with a glass of lemon and water that I dumped several packets of artificial sweetener into. Lemonade comforts me. My beloved team had just blown the biggest game of the year. Normally I would have watched the game at home, but this was the big game, so here I am sitting at this bar instead of lying in the fetal pos...

Afro Stress Relief Ch. 07

by llts1970 on Sep 23, 2019
Transgender & Crossdressers

Author's Note: - there was a character in the previous chapter called Jane who was working in Tina's company, I realized this was too confusing because of the main character Dr Jane and so I've changed the name from Jane to Monica. I apologize for the delay in getting this chapter out and hope to have more chapters completed sooner. ***** Staci rang and sa...

A Slut's Triangle Pt. 23

by Kantarii on Nov 7, 2017
Group Sex

Downstairs, all the chaos and mayhem that Kryss is causing at Brenda's all-girls party is stealing the life from it. Despite the wind and pouring rain, some of the women make a break for their cars to avoid the drama. Most of them decide to stick around and keep partying, thanks to Sheila. However, the women fleeing the kitchen warn the ones on the back porc...

Sissy Slut Ch. 01

by Scribler on Sep 13, 2017
Transsexuals & Crossdressers

It had been quite some time since I had stopped in the club. Not that I didn't crave the pain I could infect on one of the sweet young things that came to the club. I craved it more now then I ever did a few years ago. But due to relocation of my job I had to leave the city and I couldn't find a club that catered to my needs. Now I was back and I was chompin...

Bitch Maker Ch. 03

by YANKEE DAN on Sep 12, 2017
Transsexuals & Crossdressers

Author's Note: A lot of people have requested that I continue this series, and finally I have gotten around to it. Enjoy! * "Alex bring me some juice." Sammie said, rolling over in bed and hugging her pillow. "Yes mistress!" I replied, with enthusiasm. I crawled out of bed and walked down the hall, on the way past Tim's room I looked in on him. He lay t...

Siss the Bride Ch. 02

by theonewhowas on Sep 19, 2017
Transsexuals & Crossdressers

Anyone who tells you that married life is hard must be part of a straight couple that survives on vanilla sex once every two months or so. I love being married, I get to live out all my wildest fantasies and adventures with the man I love; just over a year ago I married my brother (I could explain why right now but that's a whole other story), but because I...

Fetish & Fantasy Pt. 01

by GavinIsaNuisance on Jul 13, 2020
Transgender & Crossdressers

This work is completely fictitious, any similarities to any persons living or dead is purely coincidental and entirely unintentional. All persons depicted in naked/sexual acts are 18 and up. Down and out aspiring model Taran Kilkenny becomes the hottest commodity in an escort service for trannies! But first he's gotta get trained by his new and domineering b...

My "Uncle" Caught Me in Pantyhose! Pt. 06

by JHouston on Sep 16, 2017
Transsexuals & Crossdressers

"You will make a hot little sissy in those heels and dress." said a man's deep voice behind me. I was startled. I was shopping alone in a boutique and adult novelty store near my new rented apartment. I had just moved in two weeks ago to be closer to my new college, and, I was picking out a few sexy outfits for crossdressing fun. I turned around to see a t...

My Accidental Orgy

by usmclass on Sep 16, 2017
Transsexuals & Crossdressers

If you don't enjoy stories about oral sex, transwomen, sissy sex, or orgy situations, then you need to check out the Reader's Digest website, because that's all here, and a bit more. ***** Hi! I'm Cassandra. Growing up in the 60s and 70s (in an Alaskan logging camp no less) I became very familiar with men's magazines and Penthouse Letters. Before I move...