Sissy Jail Stories

17,389 results
Orientation
Length
Source
Infinite Scroll

Reawakening

by magmaman on Aug 19, 2017
Exhibitionist & Voyeur

I married Lee because she was naughty, simple as that. I dated a lot prior to meeting her, never settling solidly on anyone. I don't even know what happened there for sure, I had no plans or even any inclination to hook up with any woman full time. Besides, she wasn't my type. Not my type at all. The first time I saw her she was up on a stage wearing nothi...

Lesser of Two Evils

by Andi_Lembke on Sep 25, 2017
Transsexuals & Crossdressers

[So to update you all. I'm sorry I haven't completed any more chapters of NWTBYG or Porn Princess. They're in the works, but creation, and good storytelling takes time, something I have less of now. I left my receptionist job to take a writing gig, and all my writing energy is going into that, but my passion for hot stories smolders intensely under the surfa...

The Landlady Pt. 01

by Manndee on Apr 3, 2018
Transsexuals & Crossdressers

I had been lodging at the address for 7 months now. When I first saw the advert, it made me smile because the lady advertising the room seemed to be so eager to have a lodger. You could see it in her photo. It was not my first choice when I looked through the properties that were available online, but it was the cheapest, and funnily enough, it looked the ni...

Cam Slut Pt. 01

by GavinIsaNuisance on Oct 26, 2020
Transgender & Crossdressers

This story is entirely fictitious. Any similarities to persons or things living or dead is purely coincidental and entirely unintentional. All persons depicted in a naked/sexual nature are 18 and up. Eighteen year old Jeremy Briarstein is forced to remain home while his parents go on an extended twenty year anniversary vacation. He is further dismayed to dis...

Quenching Thirst Ch. 03

by PutItInMyMouth420 on Sep 25, 2018
Transsexuals & Crossdressers

Warning. This story is extremely dirty and graphic. Please read chapters 1 and 2 first. *** I went back to the shower after mr. Warden had owned me. I knew that at this point I would be changed forever. For sure I no longer identified as straight. I knew no matter what happened I love cock too now. That was the most humiliating, embarrassing experience of...

Sissy PRIDE!

by nancyvasquez on Aug 27, 2018
Transsexuals & Crossdressers

I'm just sitting around, painting my toenails, and thinking how blessed I am to have been born a sissy. Of course, it wasn't always that way – I wasted so much of my life trying to fight my reality. It wasn't until I went through puberty and I saw that I was not developing physically like the other guys my age that it really began to concern me. I saw them,...

My Submission to a Real Man

by gbr2004 on Dec 28, 2017
BDSM

This is total fantasy and would never do many of the things I discuss. If not into really kinky play, humiliation, verbal abuse, and forced fem and strong discipline, please pass on this story. For all you other submissive boy and dominant men hope you like my fantasies. ***** MY SUBMISSION TO A REAL MAN It was our first actual meeting. We had emailed bac...

Turned So Totally

by gbr2004 on Oct 8, 2019
BDSM

It was our first actual meeting. We had emailed back and forth about what we were both looking for and found we had similar interests. He wanted to take a straight acting guy, take his masculinity away and turn him into his submissive sissy bitch. That is what I had been thinking and fantasizing about continually but could I actually do it? From our email ex...

Sissy

by TxRad on Sep 14, 2017
Mature

I came in from work about noon on Friday. I had been gone for a little over two weeks. Pulling in the driveway, I noticed that my daughter's car was gone but her best friend's car was parked in front of the boat on the far side of the carport. You talk about a pair to draw to; those two were it. My daughter is tall, dark, and slender, Sissy is even taller, b...

It?s Either Break Up Or Make Up

by felicia_rene on Sep 12, 2017
Transsexuals & Crossdressers

PART 1 Synopsis: I always was put off by the unsuspecting stupid love sick, pussy whipped guy is transformed against his will because the will wants to run off and have an affair, I never understood why they don't just pack and leave. The underlying theme is transformation and sexual punishment of the main character with anti gay womanizing feeling for hi...