Male On Shemale Stories

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Orientation
Length
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Infinite Scroll

Futanari Wife

by Lake_Nine on Jun 29, 2019
Fantasy

You signed as the train hit another bump, it was late and the train car was almost completely empty. Normally you wouldn't be out this late, but it was your anniversary and you were on your way to get your wife her favorite flowers. You looked around for a moment before pulling out your phone and pulling up some porn. You were married, you had been for a few...

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Brazillian Punsihment

by Ravenarioch on Feb 7, 2018
Transsexuals & Crossdressers

Frank Shepard a private detective who is trying to find his luck in Rio de Janeiro awakes in his bed during the day of Carnival, the sun's rays hitting his eyelids he turns himself over in bed and looks at the sky on this lovely day. His sky blue eyes thinking about what a horrible day to be a private investigator, his case was to find the little brother of...

Locked down in a lockdown

by MrTwister5 on Oct 19, 2020
Fetish

Being a junior software developer, you were one of the first to be sent home when the first signs of the pandemic came up. While you thought that it’d be fun to hang out at the house while everyone else was at work, it soon became evident that everyone else would follow suite. By the end of the next two weeks, all five of you were working from home. At first...

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Shemale Fun

by orangemaestro on Sep 26, 2017
Transsexual

You are a good-looking man in your mid-twenties. You are 5'10, 170 lbs., and in good shape, with some muscle definition. You have always considered yourself a man's man, but lately you have developed a curiosity about women with...something more. When you fantasize, you sometimes find yourself imagining a cock between the girl's legs. Pretty soon, that's the...

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Sheena's New Girlfriend

by Writer345 on Sep 16, 2017
Transsexuals & Crossdressers

Okay, here's my second attempt at a story for this site: it starts slowly, so if you are after instant gratification: look elsewhere. Thank you to the people who advised me about story classification after "Plaything": I'm pretty sure that I have got this one right, though! Please let my have your constructive comments as they will help me to improve. Please...

A Symphony in Dee

by spitzharder on Sep 16, 2017
Transsexuals & Crossdressers

It was a hot day in August, the wooded hills were covered in tress which made my hike cooler but the 6 miles I had walked had heated me anyway. I was following animal trails through dense trees when I came upon the clearing. No more than 15 feet on a side it was open to the blazing sun, which perversely was what just what I needed right now. With just under...

Specimens of Gender

by darkheathyr on Sep 14, 2017
Sci-Fi & Fantasy

"Hmm. One more chapter?" I rested the thick, hardcover book on my chest and turned my head to check the clock. It was only 11:47 - late, but not as late as some of the nights I'd put in lately. Still, I did have to be up at 5:00 in the morning. "Better not," I decided with a sigh. Since it was too big for the nightstand, I reluctantly dropped the book on fl...

Blossoming Shemale Ch. 02

by TheTitLover on Sep 25, 2017
Transsexuals & Crossdressers

This is inspired by:http://www.literotica.com/s/reluctant-shemale tawnysuede's Reluctant Shemale if you enjoyed it, I hope you'll enjoy this series. * * * My name was James. It was, before everything that happened, anyway. I'd come from pretty good stock, as the snooty, upper class would likely say. I guess I still did, although it would take a DNA test to...

Mommy's Special Boy

by Shelly7 on Aug 25, 2018
Transsexual

Ever since I can remember my mom loved me very much, she was always saying its so much more of a worry having boys than girls. When my father died of a heart attack when I was ten years old, mom was there even more in my life, I believe it was then that she directed me on a specific path in life, of course I could not see that all through my childhood, but n...

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Laboratory Fun

by Hypnoticus on Sep 26, 2017
Science Fiction

You stand on a street-corner in your home town. The sky is overcast and there's a rumble of thunder in the distance that reverberates off the buildings. You reach in your pocket and pull out enough cash to cover the cost of lunch, shove it into the hands of the street vendor, and begin to make your way back to the office. You would hate to be caught in yet a...

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