Sissy Jail Stories

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Infinite Scroll

Snapped: Shemale

by Templar_Writer on Oct 13, 2017
Transsexuals & Crossdressers

This is the latest entry to my Snapped series in which a woman has been pushed to the limits and finally snaps to end the torment. I'm glad to be back to writing as I haven't been able to get much done in the past few months. A reminder to anyone who has an idea that would like me to turn into a story, I am enthusiastic about ideas. However if the subject is...

Casey's Submissive Journey Pt. 04

by corduroysissy on Dec 31, 2017
Transsexuals & Crossdressers

Angie & Debbie (Fag Night) Part Two After putting on the movie Angie walked to the side of the bed and carefully removed her hat, gloves and shoes. As she did she called Debbie over and told him to lie down and get comfy. He took a sip of his drink, put it on the nightstand, then laid down on his side and watched the video. Soon after he felt Angie's w...

Afro Stress Relief Ch. 05

by llts1970 on Aug 1, 2018
Transsexuals & Crossdressers

My alarm went off the next day, my mouth and asshole ached, it was going to be a long day I thought. I had put plenty of grease up my asshole just to ease the soreness but it still felt pretty stretched. I started to remember last night, I couldn't believe I'd taken Baba G's fat black penis in my mouth, or that I'd spoken to the police officer like that! I w...

The Vacation from Hell Pt. 03

by JamesMiehoff on Dec 11, 2018
Erotic Couplings

Copyright (c) 2018 James Miehoff, All Rights Reserved. This work may not be published whether for fee or free without this copyright. --------- This is one of a series of stories set in what I call Universe-J. Universe-J is very much like this universe with a few exceptions. First the people tend to be a little more sexual and less hung up on sex that...

Simone

by Sissyhalo1 on May 11, 2020
Transgender & Crossdressers

I'm so sick and tired of my life. It was like I'm cursed. I wasn't a great looking guy in high school with bad skin and bad grades because well... I was poor. My old man was a night watchman and mom was a stay at home mom because she was poor and had no real education past junior high when she started popping us out. So everything was tight and for the m...

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. "...

Crime Doesn't Pay

by Virgil_Assad on Sep 14, 2017
Transsexuals & Crossdressers

::A note for the readers. I came upon the idea for this story some time ago. Most forced feminization stories are told from the POV of the subject being forced. I decided to change the format a little and tell a story from the other side. Special thanks to Anelle for help in editing.:: I had originally intended to move straight from one apartment to the...

Waking Holly

by Sissyhalo on Sep 16, 2017
Transsexuals & Crossdressers

It's been about a month since I told Holt, Holly the truth and moved her into my house. I never expected the side effects of what I did to her to be her to be her becoming a whole other person. I know it sounded like that's the point but the point is that you changed them, bent them, broke them and made them worse. And I fucking hated Holt, I really fuckin...

Afro Stress Relief Ch. 02

by llts1970 on Apr 18, 2018
Transsexuals & Crossdressers

In the morning I was very nervous, what if my black co-workers had seen me in my outfit and also seen me doing those things with the other black studs, "Don't be worried Tina, it's unlikely they'd recognise you in the lighting of the club and your make-up. Even if they did I don't think you should be concerned, as I've said before it's not unusual for Afro-m...

PIXIE Sissy Stripper Ch. 04

by EROTICbearscribe on Jan 20, 2020
Transgender & Crossdressers

Author's Note: There is a category switch in this chapter. The beginning chapters can be found in GAY MALE. Seeing as what happens in this chapter, the new category is TRANSGENDER & CROSSDRESSERS. ***** THE PINK BOY was located in the warehouse district across town in an eclectic area known for its nightclubs and specialty bars. Within a six block radi...