Shemale Wrestling Stories

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Alpha Gamma's Secret Ch. 2

by Wannabe Chick on Sep 11, 2017
Transsexuals & Crossdressers

-4- Molly awoke to the annoying sound of her alarm beeping. Groggily, she reached over to her night table and turned it off. It was 7:00 AM, way too early for a 19-year-old college girl to be awake, in her opinion. As she stirred, her girlfriend wiggled up against her, eager for body heat. Molly smiled and looked over at Gina – her girlfriend, lesbian lover...

A Strong Man at Work

by Samuelx on Sep 16, 2017
Transsexuals & Crossdressers

In life, some people seem to get pleasure out of pissing others off. I think you know what I mean. We've all been there. The first time I laid eyes upon Joan, I thought she was a low-class, boring and obnoxious person. Where I come from, people like that are pretty common. Who am I? Stefan. A tall and fairly good-looking Black man in his early twenties. My e...

Realization vs. Reality

by Throckmorton on Dec 24, 2019
Transgender & Crossdressers

This story is one hundred percent true to the best of my recollection. I wanted to tell someone for so long, but never have, until now. Feed back is appreciated, and applications are being accepted. Read the story, you’ll understand. To get to the story… So…here I sit. 40 years old and revisiting the confusion of my youth. I am, and always have been, a fir...

Bisexual Black Man's Paradise

by Samuelx on Sep 12, 2017
Transsexuals & Crossdressers

The name is T.J. Brown. I'm an engineer working at Walpole, the toughest correctional facility in the state of Massachusetts. My days are spent reading books, exercising and occasionally tussling with other workers. The facility is undergoing some expansion and I'm the lead engineer on this gig, working closely with the architect. Such is my life these days....

BEA 2016

by devoutmalesub on Sep 25, 2017
Transsexuals & Crossdressers

Book Expo America. Here we go, again. Will it be the same thing again? Fly in, get the baggage, take a smelly cab to the hotel. Meet my Sales Director, Victoria (who goes by V), in the bar. "We've got to set up the booth, Jack. But first, let's have a drink or two!" She winked. V has been my boss for five years. She rode the team hard for sales numbers, bu...

All the Way

by NearMiss on Sep 18, 2017
Transsexuals & Crossdressers

A different spin on the typical 'I got caught dressing up' story. I've always been fond of large women, not obese necessarily but you know, big. Like Amazonian big. Tall, big curvy hips and a chest to match with broad shoulders, but not in a masculine way mind you, but kind of proportionate for a girl. Let me tell you they aren't really that easy to come...

Birth of a New Sissy Ch. 01

by AltErik on Sep 18, 2017
Transsexuals & Crossdressers

Usual disclaimers, though if you are already browsing stories on this site, you must have an idea what you're getting into by now. ;-) This story contains male to male sex, Crossdressing and Dominant/Submissive themes, so if this is a problem . . . wave off! This story is fictional story based on a fantasy of mine. While it is fiction, I did use myself an...

How I Met Alyssa

by thatlonewolf on Sep 11, 2017
Transsexuals & Crossdressers

Author's notes: This is my first story. Any feedback would be greatly appreciated, since I'm still learning the ropes. This story is about a romance between a man and a shemale, if you do not like this, you should click 'back' on your browser. If this story is well received, I might bring up a sequel, I already have some ideas, but feel free to bring up any...

Crossdresser's Rassling Dreams

by footqueen99 on Sep 17, 2017
Fetish

The following is an email chain between two crossdresser's who enjoy wrestling. All persons depicted in this writing are well over 18 years old. ***** I wish i could have been there! I would love to see a few pics if u can share. I love pro style fantasy matches. I love all the holds, drama, trash talking and victory poses where u pose with your stocking...

Pam's Shemale Experience Ch. 10

by majicman21 on Dec 2, 2019
Transgender & Crossdressers

Pam woke up, and as she remembered what day it was, a smile crept across her lips. Earlier in the week, her owner had decreed that she would not fuck Pam until Wednesday. That had been Sunday night, and now, with Monday and Tuesday past, today would be the first time in a long time she would feel that magnificent cock opening her up. It's been too long.....