Surprise Shemale Stories

136,276 results
Orientation
Length
Source
Infinite Scroll

Growth-XX

by FlatCap90210 on May 20, 2019
Science Fiction

James felt as if he was going insane. It was summer, the sun was shining and he was at the beach ogling girls. Tits of all shapes and sizes surrounded him, wrapped in bikini tops, one pieces and other pieces of fabric of varying coverage. James' heartbeat pounded in his ears and throbbed in his crotch, digging a furrow in the sand beneath him. He was lying o...

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Pam's Shemale Experience Ch. 03

by majicman21 on Sep 12, 2017
Transsexuals & Crossdressers

It was late morning on Saturday. Tanya was sitting at the kitchen table, wearing a satin robe that she had brought from home, left open to reveal her nakedness. The daily newspaper was in her hands, Tanya leisurely reading it as Pam knelt before her, slurping greedily along her balls. They were slick with saliva, gleaming like polished ebony. Her fingers wer...

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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Job Interview

by britneyfan on Sep 11, 2017
Transsexuals & Crossdressers

I was interviewing for a new secretary and it had nearly reached the end of the day with no likely successful candidates. There was just one to go, a Tracy Class, whose CV certainly looked impressive and seemed as if she would do pretty well for the job, but I had to wait and see. The company's receptionist, Paula, put her head around the office door to tell...

The Virgin Tranny & the Bride Ch. 07

by yano on Sep 25, 2017
Transsexuals & Crossdressers

Firstly, on behalf of Roberta and myself may I thank you all very much for your very generous votes. We now continue Roberta's story and it is the morning after and tranny Roberta views the video of her big wedding day before a shopping trip and an exciting public photo call. * * * * * Next morning, I was awoken by a very excited John. "Come and see this...

Joel Gets Caught by His Wife

by Downforeverything on Sep 18, 2017
Transsexuals & Crossdressers

This is a fictional story written for a fan about their sex life. If anyone else has a story they'd like written for them about fact or fictional events feel free to message me. As always please leave comments or constructive criticism so I can make your pleasure better! * It was Monday afternoon. Joel had taken the day as an opportunity to work from home...

Mikes First Transgendered

by SamanthaMeyers on Nov 16, 2020
Transgender & Crossdressers

This is an absolute true story. Mike loves transgendered I had just turned 30 and was about 1 year out of my divorce. I was dating a Filipina lady named Mika who was not the best person for a relationship, for many reasons. During our relationship Mika used to take me to this Filipino dinner restaurant which had food and late night live musical shows. Duri...

SheMale Sirens Ch. 04

by WhiskeyIsGood on Sep 25, 2017
Transsexuals & Crossdressers

I never thought I would wind up in what many would have thought was just some fantasy world. I would have considered myself one of those people who thought it was just someone's fantasy. I happened to stumble upon Anthemusa by total accident, which I would later learn was really how the majority of the men on the Island came across it. I had been heading t...

Celebrity Shemales!

by Thorsten007 on Feb 6, 2018
Transsexual

Here, you can fuck the shemale version of your favorite celebrities! Feel free to add new celebrities! IMPORTANT: Leave a like for whichever celebrity you want me to write a shemale story for first!What's next? Scarlett Johansson Nicki Minaj Natalie Portman Britney Spears Jennifer Lawrence Margot Robbie Kate Winslet Kate Upton Keira Knightley Emma Watson Ka...

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The Shemale Possession

by SexyKate69 on Dec 12, 2018
Transgender & Crossdressers

I was in another day in the laboratory, arranging the experimental machines. It would be an ordinary day if it were not for one of the machines that went into overload and exploded, after the explosion I opened my eyes and I was scared to see myself stretched out on the floor. How could that be? There was only one explanation, I was dead, that's when I notic...