Sissy Jail Stories

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Jailhouse Faggot

by nancyvasquez on Oct 14, 2017
Anal

Before I got sent to the joint I spent over 6 months in county jail. The jail was old and they had old fashioned cells with bars. The cells were small, 4 bunks in each cell. I had never been in jail before and I was scared and it showed. I was young, slightly built, and timid as hell. The cellblock I was housed in was on the 4th floor. There were two sides...

Allyson the Sissy Whore Ch. 01

by sissymaidallyson on Sep 12, 2017
Transsexuals & Crossdressers

Kevin was your prototypical mid 20s guy. He had a decent job and lived on his own. He had good friends and whilst he was single he didn't find any problems getting what -- or who -- he wanted in the bedroom. However he had long been fascinated by glory holes and by being serviced in them but by being the one servicing. He was convinced he was straight and l...

Cock Sucking Jail Whore

by RobinTVDaniels on Sep 15, 2017
Transsexuals & Crossdressers

I've always known that I was not meant to be a guy. Being sexual curious I would look at porn mags like any one does. At first it was just magazines with pictures of naked woment. It was when I ran across my first Hustler magazine that my life was changed forever. Seeing pictures of studly guys with big hard dicks and women on their knees about to suck or be...

Allyson the Sissy Whore Ch. 02

by sissymaidallyson on Sep 13, 2017
Transsexuals & Crossdressers

Kevin woke up with his head swimming. Kevin...or was he Kevin any more? Was he just Allyson? He looked down at himself and saw his name badge and decided that for now he should just think of himself as Allyson. Think of herself as Allyson. Oh it was just too confusing. As he started to come to terms with what was happening he saw the door of the jail buildin...

Sissy Lauren Pt. 02

by CdJade on Sep 14, 2017
Transsexuals & Crossdressers

Chapter Two: A New Girl It was the first day of February and almost six months into Freddie's jail sentence. Or at least it would be if Freddie still existed. On his second week inside, Freddie had been transformed into sissy Lauren, the girlfriend of E wing boss, Ronnie. Lauren had now learnt how to apply her make up to the style of most of the instructio...

Sissy and Missy

by ChristopherDB on Feb 12, 2019
BDSM

Copyright 2019 Christopher D.B. * The central vacuum system made barely a sound as I made my way through the apartment. It was spacious and occupied the entire third floor. Although fully furnished and containing some of Countess Tori's personal items, she only stayed here a few nights a week. My feet were hurting, as the toe box on my pumps fit a little...

The New Neighbors (Black Femdom)

by Dunn81 on Aug 12, 2019
BDSM

Hi my name is Julia i'm 42 years old and i'm with my daughter Sofia who's 20. I'm a pretty fit girl who are vegan. I Lost my husband 5 years ago and since that i never dated anyone. I'm a 5'2 brunette with medium size boobs and a medium sized ass too. I weighted around 130 pounds. My Daughter is 5'5 big boobs and small ass. She trained at the gym a lot since...

Arabian Nights Ch. 01

by kayla_femboi on Sep 14, 2017
Transsexuals & Crossdressers

I was in Dubai for business. I was essentially a salesman for a company that specialized in medical equipment for hospitals. Nothing terribly exciting, but the pay was decent and I got to travel quite a bit. I wasn't cruising around the world in first class by any means, but the companies would put me up in hotels for the trip. I loved this since it gave the...

Satan's Sissy

by nancyvasquez on Oct 15, 2017
Transsexuals & Crossdressers

Oh you stupid little faggot! You just had to go and get married to a woman! Why?? Why fuck up some poor girl's life like that? Was it because you crave humiliation, and subconsciously you knew it would be just a matter of time before you got caught, and you would be outed publicly? Outed as a pole smoking homosexual who was more at home in frilly skirts and...

Ultimate Sissy Weekend Ch. 04

by SissyTwinkleToes on Jan 13, 2020
Transgender & Crossdressers

Susie is lying in the store supply closet next to Tinkerbell. It's six in the morning, and they've only just finished cleaning the entire supermarket. After changing each other into fresh diapers, and using the few left over to make pillows for them both, the two exhausted sissies lie side by side in the cramped supply closet. Tinkerbell's right hand, handcu...