Sissy Jail Stories

17,389 results
Orientation
Length
Source
Infinite Scroll

Graduate Studies to Gay Pt. 02

by jamtby on Apr 9, 2019
Transgender & Crossdressers

After the night at James' apartment the previous quarter, I had tried to put all that out of my mind and concentrate on school and be normal. I did see James once on campus and he asked how I was doing. He hoped I had gotten a good grade on that paper I was writing when I met him at Jimmie's that fateful Friday night. He also said that if I wanted to earn so...

The Cuckold's Babysitter

by yumacd on Sep 26, 2017
Loving Wives

Hi, I haven't written in a while. The set-up for the sex is probably too long. I'm thinking of continuing the story. Hope you enjoy it. YumaCD === My wife, Tami, has been cucking me for a couple of years now. Most of you Literotica readers have heard the story before... - It started when I revealed my fantasy of watching her with another man one night...

AliExpress and Sissy Downfall Pt. 08

by His_fag_wife on Jul 10, 2018
Transsexuals & Crossdressers

Emma's gaze swung around the room taking in as much of the contents of the room as she could. So many of the items being completely unrecognizable to her. "Close your mouth my dear little slut or I may have to put something in it." "Yes Master, sorry Master, it is just an amazing collection." "It is, isn't it and we'll get Charlie to choose your new plug...

Playing the Part

by Sissysdream on Jan 20, 2020
Transgender & Crossdressers

All people in this story are above 18 or older. This is just a fast story I wrote and don't know if I will do any more on this story. *** My name is Tommy, but these days I go by Tammy. A few weeks ago, I was turned out by my high school bully during summer break and now I am a happy cum drinking sissy. I know I'm getting a bit ahead of myself here so let...

A Model for CC's

by Fibaro on Oct 5, 2020
Transgender & Crossdressers

(This story was requested by one of my readers. This is a stand alone story, but reading "Neighbourhood Terror to Sissy" first is advised as this story takes place in the same universe.) Intro Victor was just a regular guy down on his luck. A month ago he still had it all, a beautiful girlfriend, a nice apartment and a decent paying job working for an acco...

Adult Arcade Sissy

by nancyvasquez on Sep 19, 2017
Transsexuals & Crossdressers

Dwayne started hanging out with us when I was 18. He was older than us - 28 - but he came across as someone our age. Because he was older a lot of us guys sort of hero- worshipped him - me included. So naturally I was flattered when he began to spend a lot of attention on me in particular. The guys I hung out with were a little wary of Dwayne, because he w...

Neighbourhood Terror to Sissy Pt. 17

by Fibaro on Feb 3, 2020
Transgender & Crossdressers

Chapter 19 The drive back home was pretty uneventful, Lisa just sat behind the wheel smiling ear to ear. She had had an awesome day so far, making out with two gorgeous women and now she would spend some quality time with her sissy boyfriend. Marcy was very worried about that quality time. She hoped for sure that it wouldn't involve that dildo going up her...

Sin of Vanity Ch. 01

by Belongs2Beth on Sep 12, 2017
BDSM

Author's Note: This story continues the story of Vance, Marcia's friend introduced in "Marcia Goes Back to School". I have made an effort to make sure that this chaptered story can be read as a stand-alone or as an episode in a continuing series of stories set in the fictional town of Torquay, Connecticut. Readers of my earlier works will be familiar with Mi...

Call Me Katie Pt. 01

by KrierWitz on Sep 18, 2017
Transsexuals & Crossdressers

This is the first part of a story following Kent Wiltshire and his journey from an independent man to a submissive slave girl. Please let me know what you think, and if there is any themes you would like to see incorporated in the future. ***** My name is Kent, I'm 22 years old and live in a two-room apartment in Stanley, Idaho. It's a small city, with ju...

Humiliated

by SissyJane on Sep 16, 2017
Transsexuals & Crossdressers

Mandy is Satan. That's all there is to it. She's made my life hell ever since I met her in Psych 135 class in September. She is one cruel, cruel bitch. I don't know what I'd do without her. They say people secrets want to get caught. They make stupid mistakes or leave evidence around to their secret. Psychologically, they need to break their silence. I su...