Sissy Contract Stories

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You Got the Part! Ch. 03

by Checkmate215 on Sep 26, 2017
Transsexuals & Crossdressers

I would like to thank Mr_Owlow for all his assistance with editing this story. In typical Riley fashion I was in a bit of a situation. GiGi's T.V. show was a complete success and we were picked up for a second season. America was in love with the cast especially GiGi and myself. We were making the rounds on talk shows and late night. We were doing endorse...

A Downtown Moment

by Sheermistress on Sep 12, 2017
Transsexuals & Crossdressers

I had reason to head downtown for a meeting with some industry colleagues and after my meeting I dropped in to see a friend of mine who I used to work with. Loretta and I worked together for about a year on similar project as contract workers, I moved on to other things and she stayed with the company. While I never went out with Loretta, we did have the od...

The Prostate Exam Pt. 04

by His_fag_wife on Sep 18, 2017
Transsexuals & Crossdressers

It had all started with a routine visit to his Doc for a simple prostate exam. After he'd given away his naturally submissive tendencies by not being able to resist pushing back against her finger, forcing her finger deeper into asshole. At that point his female doctor had decided to test just how submissive he was. She gave him the option to back out if he...

Breaking with Traditions

by Canadagander on Sep 17, 2017
Loving Wives

Copyright © 2005. All characters, events, and text in this story are purely fictional, and are created by and the sole property of the author. All rights reserved. - - - - - - - - - - - - - - - - - - - - - - - Writer's Note: It's time for Canadagander to make a public disclosure, to come out of the writer's den, so to speak. 'Gander is not a real person....

J*Kohle Punishes Her Man

by LiliesLaughing on Sep 14, 2017
BDSM

Her breath caught slightly as she looked up into the face of inarguably the most beautiful man she'd ever laid eyes on. This was a man of dreams and stars. His hazel-green eyes, glittering with firelight were framed by endless lashes and wisely arched brows. His wide, flat nose and big soft lips were set in a square-jawed face the precise shade of light brow...

The Millers Ch. 04

by CiaraSwallows on Sep 15, 2017
BDSM

It's been forever since I had a weekend off from the restaurant but I was happy to have it so I was really looking forward to my free time. Unfortunately, when you are in a contract which you have signed your freedom away for six months you don't really have free time. I was reminded of this when I walked in the door Thursday night and saw my bag packed wait...

The Gynecomastia Kid Ch. 02

by Johnboy9 on Sep 16, 2017
Transsexuals & Crossdressers

It's been two weeks since I got out of the hospital and I was feeling better and better as each day passed. Having no income and no real money of my own, to speak of, I was forced to continue wearing the clothes that Crystal left me since I couldn't afford to go out and buy clothes of my own. I must say though I'm getting to like the soft, airy feeling of t...

Humiliation Journey Never Ends

by Subkoksukr4u on Jun 25, 2019
Transgender & Crossdressers

Here I am once again looking up into the eyes of my tormentor, my superior in every way, especially his cock, 10 1/2 inches to be exact. I know because when I first met him he made me measure it with a ruler. He made me measure mine too. I was embarrassed, humiliated and shamed for being so small. It hasn't been called a penis or anything remotely masculin...

Poker Night Substitute

by JustATale on Sep 13, 2017
Transsexuals & Crossdressers

I was an entry level accountant at a bank. The pay wasn't great but it was what I had studied at college and it was a start. To help with expenses I shared the house I rented with Todd, and Trish. Todd was an architect working as a draftsman until he could get something else. Trish was working as a cashier at a local store. We all got along great and the arr...

Seven Lessons Ch. 02

by Vertex on Sep 16, 2017
Transsexuals & Crossdressers

Previously... Bryan is an arrogant biggot. This Halloween season, someone has decided to teach him a series of 7 lessons. Yesterday the lesson was acceptance, but as he chose not to accept the lesson, he ended up with no body hair, wearing a bodystocking and being fitted with a chastity device. Will he learn his remaining lessons? That night he had many...