Sissy Jail Stories

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Orientation
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Infinite Scroll

Sissy for Satan!

by nancyvasquez on Jan 14, 2018
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...

I Admit I Was Speeding

by Cute Little Thing on Sep 16, 2017
Transsexuals & Crossdressers

I admit that I was speeding, when the cop pulled me over. What can I say, I was rushing to get home. I get that way when I have panties and a bra on. But let me start at the beginning, because this is a long story. It was a Friday night and I had been saving up all my courage for a month, since my girlfriend had told me she would be going out of town for the...

Ultimate Sissy Weekend Ch. 05

by SissyTwinkleToes on Jan 21, 2020
Transgender & Crossdressers

Susie can feel her diaper getting warm as she fills it with more pansy pee. 24 hours ago, she posted an envelope containing five keys, and still has another 48 hours until they arrive at her house. Those keys are for the lock that keeps her in her dress, the handcuffs that keep her right hand locked to this sissy on her left, and the tiny pinching chastity c...

Prison Woman

by nancyvasquez on Sep 19, 2017
Transsexuals & Crossdressers

I get a lot of questions from men that I meet. Not all of them want to have sex with me; some just are curious about what I'm all about. A lot of people who know me know that I am an extremely feminized male who became a Queen when I went to prison due to alcohol related offenses. I always say that I became a woman in prison - and that is true. But I guess...

Uncovering the Sissy Beneath Pt. 03

by jefferyscott745 on Jun 25, 2019
Transgender & Crossdressers

Disclaimer: This story contains extreme fetishes including BDSM and forced seduction. It is also purely fictional. This is part three of my previous work. Be sure to read parts one and two if you wish to understand the background of this section. *** I hesitate to follow him out of the bedroom, as my anxiety is out of control. "Have I just been kidnapped...

Quenching Thirst Ch. 04

by PutItInMyMouth420 on Sep 25, 2018
Transsexuals & Crossdressers

This chapter includes semi-forced sexual situations and will be very graphic. If you are not into the idea of interracial gay sex turn back now. *** As I sat in the back of the police car, I thought about the situation I had gotten myself into that night. Generally, I would have been a scared little bitch of being raped in jail, but now that I had been fu...

Happy Endings

by desireethtttv on Sep 14, 2017
Transsexuals & Crossdressers

As I sat in Julie's bedroom, my high school's self appointed sleazy easy slut, whom I'd so long held discreetly in my deviant mind as an idol and often dreamed of having the same reputation; she appeared dumbfounded as if her brain were stuffed with cock. Innocence was always in her mind while with me. Her thoughts of me were nothing more than a boy who like...

Superstars Rise and Superstars Fall Ch. 01

by felicia_rene on Oct 6, 2020
Transgender & Crossdressers

Superstars rise and superstars fall 1 Part 1 of 4 By Felicia Rene This is fiction so literary license allows for the omission of condoms, but our reality doesn't. Enjoy the story Synopsis: The underlying theme is transformation and sexual punishment of the main character for his anti-gay womanizing feelings. For his heinous actions initially making h...

Afro Stress Relief Ch. 09

by llts1970 on Feb 3, 2020
Transgender & Crossdressers

After a hectic and traumatic weekend, it was Monday again, I was still in a state of shock after what had happened. I spent most of the day at my desk doing very little, and wondering if any of the loading bay crew had seen the photos of me kissing Drake's ass, but I thought they wouldn't recognize me, as I was fully made-up as a sissy in the picture, but I...

Cosplay Gone Bad

by CassidyCaine on Sep 13, 2017
Transsexuals & Crossdressers

The night had gone perfectly except for the small fact that I was going home after dropping off my girlfriend at her place. I'd agreed to cosplay with her for the local convention in part to further our connection and enjoy a little play together. When she'd suggested dressing up since her best friend couldn't come and it was a passion for her, I figured wha...