Shemales Stories

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Orientation
Length
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Infinite Scroll

The Society Ch. 03

by Barno on Sep 13, 2017
Transsexuals & Crossdressers

Heidi's erect penis was sliding in and out more easily now. When she first mounted me being gentle wasn't her first priority. It was my first match and I had almost beaten her according to the wrestling judge. In fact many in the crowd of 60 or so spectators had disagreed and showed it by booing the decision, it had been that close a contest. This didn't sit...

Of Two Minds

by Cyanlot on Sep 12, 2017
Transsexuals & Crossdressers

The middle portion of this story was intended to be conveyed in two separate columns, providing parallel presentations of different perspectives on the same events. Literotica's software does not permit such formatting. Accordingly, I have interwoven the material that was to be displayed side-by-side, formatting one portion normally and the other in ALL CAPS...

Lindsay Gets a Special Gift

by Cartman94 on Sep 11, 2017
Sci-Fi & Fantasy

I was sitting at my laptop chatting with Lucy, my best friend, as the warm summer sun shone through my bedroom window. I hadn't been this excited in a long time. College started in 2 weeks and I couldn't wait. And the best part was, Lucy was going to the same college. Lucy had been my best friend since first grade. We've had our ups and downs, just like ever...

Code Name Tequila Ch. 01

by Travel_by_day on Sep 13, 2017
Transsexuals & Crossdressers

It was a beautiful day in San Diego. The sun was shining, and Ria Ortega was enjoying sea breeze on her face as she stood in Embarcadero Marina Park watching the sea. Out on the water sail boats tacked and jibed as they headed into San Diego Bay. Ria smiled and thought how far she was from the drug dens and slums of Oaxaca. She had seen so much killing ove...

My Hot Wife Katie Ch. 31

by Freddyj881 on Sep 25, 2017
Erotic Couplings

Katie Visits Wichita Mrs. Jackson felt her cotton panties bunched up against her clit as she drove down Interstate-70 towards Wichita Kansas. Any movements caused a shiver to be sent up her spine. The sexy woman's pussy was hot and wet. She hated long car rides, especially alone, but this was different. The naughty wife had spent a bit more time in front of...

Muscle Mature Fucks Rough Pt. 04

by razmatazz17 on Jan 30, 2018
Transsexuals & Crossdressers

Hey Everyone! Sorry that this took a while, I just wanted to try other projects. Speaking of which, this is going to be the last one in the series, just because I want to put a period on it for a while. Maybe I'll work on it again someday, but no time soon. So since this is the last one, I'm gonna try and go ham on this one. Sorry if this news is disappointi...

Introducing Virginia Holton

by JonathanStone on Sep 16, 2017
Transsexuals & Crossdressers

A warm spring south Florida sun poured through the darkened windows of Marla Holton's corner office, brightening the firm surface of the sky blue carpet and even revealing "fribbles," her description of the tiny bits of whatever that a good vacuuming by the cleaning crew would clear away tonight. Marla Holton had a PowerPoint slide presentation that she need...

My First Shemale Experience

by EZ_CUM_EZ_GO on Sep 12, 2017
Transsexuals & Crossdressers

My husband Dan and I have always had a great sex-life, but with the day-to-day pressures of working and trying to make ends meet, we weren't always up for it or in the mood. Because of that, we had made a promise to one another early on, that at least once a month we'd have what we called a "special evening". It was something the two of us looked forward t...

Sweet Julie Birth of a Shemale

by tawnysuede on Sep 16, 2017
Transsexuals & Crossdressers

Chapter One Is It Just a Role? The dress rehearsal for the drama club's latest production was over. The curtain fell, the audience of excited parents applauded enthusiastically. The curtain rose and the performers stepped forward to take their bows. The curtain fell again and still the crowd applauded. The two stars, Troy and Julie, took their positions ce...

Simone

by Sissyhalo1 on May 11, 2020
Transgender & Crossdressers

I'm so sick and tired of my life. It was like I'm cursed. I wasn't a great looking guy in high school with bad skin and bad grades because well... I was poor. My old man was a night watchman and mom was a stay at home mom because she was poor and had no real education past junior high when she started popping us out. So everything was tight and for the m...