Shemale Fucks Boy Stories

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Infinite Scroll

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...

Pam's Shemale Experience Ch. 08

by majicman21 on Mar 11, 2019
Transgender & Crossdressers

Content warning: one scene with a golden shower... Pam woke with a start. It took her a few seconds to hear her alarm ringing. Next to her, Tanya was still asleep, and further down on the bed, Alex was as well, her head resting on Tanya's thigh. Pam reached over to the bedside table and quickly turned off the alarm. Neither of the other women stirred....

Journey to Trans Submission Ch. 01

by bluev on Jul 15, 2020
Transgender & Crossdressers

It has been at least thirteen years since I first discovered my kink and one year since I started to think about making it come true. This is a kink I have not shared a word with anyone for a fear of being judged and a fear of being told that it was not right to indulge in such objectification. Finally I came to the point where I said "screw the world, it's...

Bdsm adventures

by Sgtwolf on Dec 7, 2017
BDSM

This story is for a compilation of many different bdsm adventures. It was formerly known as latex adventures, but as chapters developed they dealt more and more with different aspects of bdsm, and less consistently with latex. Latex still exists as a strong element in many of the chapters, namely because I like to write about characters wearing it. I created...

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Pizza Boy Sissy Pt. 01

by BluntSlut on Sep 14, 2017
Transsexuals & Crossdressers

A fantasy fiction. ***** My name was Sam and I was a 18 year old pizza delivery driver. I just finished high school graduating early and started the summer working for Papa Pizzas. I had never really been a ladies man due to my non masculine body and long girl like hair. I was also really nervous to try to get with woman because I had a small penis. Becaus...

Craving Shemale Cock Ch. 01

by jeritza on Oct 22, 2019
Transgender & Crossdressers

I stood nervously on the dark cobblestone alley street, in front of the unmarked door, running through the possibilities in my head, speaking under my breath. I was thinking of all the events that led me to this moment - the perverted path I had gone down. This is it. This is finally happening. No turning back now. Dear god, no turning back now. *** I was...

Sexy Hung Red Head

by mrstanley on Sep 13, 2017
Transsexuals & Crossdressers

This story is written from the Shemale's point of view. "Francine" is based on a real Transgender woman from California. She gave me the outline of a meeting she had with "Jonathan." ***** My name is Francine and I am a natural red head blue eyed 34 year old Transsexual. My skin has a very light complexion with numerous freckles. I have been on hormones fo...

Shemale Devil in Disguise Pt. 02

by Chomedey on Mar 2, 2020
Transgender & Crossdressers

Mid-June 2018: About a month has passed since I went back to my parents for work and about 2 weeks went by since I went to that party where I first met Rebecca. Since then, not much has happened because I wanted to distance myself from the group. Although I try to see them as least as I possibly can, I still want to get the gossip from my girlfriend in order...

My Stepmother's Surprise

by sissybr on Sep 12, 2017
Transsexuals & Crossdressers

This is my first story, so I would appreciate some tips and comments. Please enjoy ^^ * My name is Robert, I'm 18, skinny and not too tall. I've never had much luck with girls, in fact I never dated one and I used to spent my days playing games on my computer and watching porn. Shemale porn. Dominant shemales fucking men. I wish i could be one of those men...

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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