Shemale Stories

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Orientation
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Infinite Scroll

Mary Sue's Big Ride Ch. 01

by Cilantra on Aug 1, 2018
Transsexuals & Crossdressers

At eighteen years old, I'd made my fair share of mistakes, but this one was by far the worst. I'd asked my last ride to drop me off at a highway crossroads, God knows how many miles back. Told him I had enough food and water, and brains, to make it on my own. He had warned me how dangerous it was, but I had been so cocksure. So certain in my ability to surv...

My First Time Out Ch. 03

by Shayna on Sep 16, 2017
Transsexuals & Crossdressers

Angelo was still working on Shayna's blonde wig. He fussed with it, combed it, and teased it. Angelo knew a romantic style was very important to Sir Dominique. Shayna was escorted to a tremendous makeup table. Saki placed a headband on her that stretched her scalp and raised her non-existent eyebrows into a feminine position. Shayna could tell Saki was an e...

Bayonetta's Abuse Ch. 09

by ChainedToAKeyboard on Dec 16, 2019
BDSM

The past catches up with us all, eventually... And we must all decide if we're bound by it. Bayonetta's Abuse IX -- The Ties That Bind *knock knock knock* James awoke to three courtesy taps on the door followed by a key-card lock releasing. The door opened and two men entered. James pulled himself up into a sitting position, leaning against the upright p...

Jay's Sex Club Adventures Ch. 02

by WhiskeyIsGood on Sep 11, 2017
Transsexuals & Crossdressers

The next day, I woke feeling refreshed, like it was the start of a new life...I cannot explain it but it felt like a great weight had been lifted' from my chest. Some would consider that to be the typical feeling you get after being laid for the first time in months. Ordinarily, I would agree, but in this instance I felt as though it were something completel...

Amanda and Me Ch. 07

by Tallnhard1 on Sep 25, 2017
Transsexuals & Crossdressers

This story contains sex between a transsexual top and a male bottom. If you do not like stories where a man gets fucked by a transsexual please stop reading. ____________________________________ I was naked and alone in Amanda's bed when I awoke. Soft morning light filtered through the blinds as I slowly sat up and rubbed the sleep from my eyes. Wincing fr...

Trapped and Trained Ch. 11

by SissyIndy on Sep 25, 2017
Transsexuals & Crossdressers

It took me hours to fall asleep that night. It was hard to narrow it down to just one reason why... Maybe it was the tingling feeling of my fishnet stockings sliding around on my pink silk sheets each time I moved. Or perhaps it was trying to get used to the feeling of these D-cup breasts flailing around as I tossed and turned, the glue holding them on pull...

Life With Miss Ida Ch. 02

by Sheermistress on Sep 12, 2017
Transsexuals & Crossdressers

When I woke the next day, Saturday – late as it was due to the long evening earlier – I started playing everything over in my mind again and kept coming up with the same result – there was nothing that suggested to me that Ida would not welcome Georgia into this relationship – she never once turned me off, nor seemed turned off by how I was dressed. She didn...

A Sissy Saga Ch. 24

by Snurge on Sep 13, 2017
Novels and Novellas

The early morning sun made the windows of the great house sparkle, and the ancient, dappled walls of Fairyfield Grange looked like they'd been daubed with gold. Abigail swept across the back patio and admired the recent changes. The large windows facing onto the terrace had been taken out and replaced with French doors. It was a facet of his mother's ultima...

The Big Mature Shemale Next Door

by SugarandSalt on Mar 13, 2019
Transgender & Crossdressers

"Please can I just wear my old swimming trunks?" Warren begged. "No!" his mom yelled back from the other room. "Barbara purchased that for you. It was expensive so you better remember to thank her." Warren looked at himself in the full length mirror. At eighteen, he had hoped to be taller. His body looked puny. Why hadn't his shoulders broadened like the o...

The English Professor

by ShemaleCumDump on Sep 18, 2018
Transsexuals & Crossdressers

As I sat in yet another dull English class I asked myself again, seriously, why do I need to read Chaucer? Is that necessary for anything I will do in my life? And as much as I try to convince myself the answer to those questions are yes, I still can't get interested in what he talked about in 1400 ad. However, there were two things jiggling at the front of...