Shemale Stories

1,331 results
Orientation
Length
Source
Infinite Scroll

Twenty-Two More Questions

by silkstockingslover on Jan 20, 2020
Reviews & Essays

Twenty-Two More Questions Summary: 22 questions asked by readers answered. NOTE: Thanks to Tex Beethoven and Robert for editing. I wrote the essay Twenty Questions in December 2017 and Twenty-one More Questions in 2018. I answered the following questions, in case you want to read them. 1. Are you really a teacher? 2. How often do you wear nylons? 3. Wh...

The Law of Attraction Ch. 08

by hottchic on Sep 17, 2017
Transsexuals & Crossdressers

This story is a transsexual fantasy. Before reading this chapter I highly recommend that you read chapters 1 to 7. The first four chapters of this tale were told from the prospective of James/Jamie who started out as a shy cross dresser. This is the forth chapter to be told by Ashley a hard core lesbian who becomes attracted and eventually falls in love w...

The Law of Attraction Ch. 07

by hottchic on Sep 14, 2017
Transsexuals & Crossdressers

This story is a transsexual fantasy. Before reading this chapter I highly recommend that you read chapters 1 to 6. The first four chapters of this tale were told from the prospective of James/Jamie who started out as a shy cross dresser. This is the third chapter to be told by Ashley a hard core lesbian who becomes attracted and eventually falls in love w...

Vegas: The Dirty Dozen Ch. 09

by Benny024 on Sep 14, 2017
Transsexuals & Crossdressers

I had a couple of days off over Thanksgiving weekend last year and, since, I had no relatives to chauffeur around; I had lots of free time. I hit the couch and watched the prerequisite football games, some movies, and got plenty of rest. By the third day, I had to get out. Being horny, I elected to go an adult theater. I chose one that I had never visited....

My First Boyfriend

by DailyReader on Sep 13, 2017
Transsexuals & Crossdressers

I groaned as I rubbed myself through my black lacy panties. As my hand moved, I began to grind up against it, my hard cock pressing against the soft material. Whimpering, I began to squirm, unable to help myself as I came, soaking my panties and leaving me a sticky, cummy mess. It had become my daily routine -- get up, go to class, walk back to my dorm room...

Ladies Night at the Leather Bar Ch. 02

by latecomer91364 on Sep 15, 2017
Transsexuals & Crossdressers

Now that you've met Chloe in Part One: Today I want to remind myself of how much I owe her for luring me into the circumstances wherein I met a beautiful man, a man who would change not only my life, but my basic conception of myself. I found him in the most unexpected of places. A place where Chloe brought me. SUMMER 2011. THE SAN FERNANDO VALLEY. I had...

Toy Stories Pt. 01

by 1077ad on Sep 16, 2017
Novels and Novellas

Chapter 1: Urinal Gag This one is dedicated to M.S. It was during an email exchange that I sketched out the fantasy I'd had when I first came across the Urinal Gag online, and that gave me the impetus to write this out. That shows how valuable that feedback (especially emails and private messages) can be. It makes it feel worthwhile to know that these stori...

My New Girl? Ch. 02

by oralfriend on Sep 12, 2017
Transsexuals & Crossdressers

This story is a departure from my usual subject matter, at least to a certain extent. I hope you enjoy it. This story is also a *romance* so if you are not interested in that aspect of a relationship please do not read it or comment as those comments will be cheerfully ignored since you have been warned. ***** Our dates took on a new dimension now that the...

Young, Bound and Captured in HD

by spitzharder on Sep 14, 2017
Transsexuals & Crossdressers

Brie stepped down from the bus outside the airport terminal, looking radiant in a short blue dress, this could be the gateway to a new life for her. Her, the very word set her apart from the details on her passport, born a boy, she had been living as a girl for some years. She had 'C' cup breasts and a well rounded ass, though, when naked, she felt she lacke...

The Wonderful Adventrues of Miss K: The Tower...

by BrettLynn on Sep 16, 2017
Transsexuals & Crossdressers

The Wonderful Adventures Of Miss K: The Tower Of Power Welcome to yet another wild sex romp of mine. If it illegal in your jurisdiction to read erotic materials such as this, please don't read this. I reserve all non-electronic and all commercial rights to this work. If you wish to read some of my other work, please check out my profile. The name 'Brett L...