Shemale School Stories

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Futanari World

by styxmaster on Apr 16, 2016
Fetish

You wake up this morning to the sight of your younger sister Sarah pulling your covers off of you. "Get up Doug, you don't want to be late for school." You get dressed for school after Sarah leaves your room. you never mind school that much, you mostly get B's and A's in your classes but given the opportunity you would like to just stay home and wa...

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How Dicks ended up in My Mouth Ch. 01

by ret123 on Sep 19, 2017
Transsexuals & Crossdressers

My name is Joe. I am a married, successful business man with a pretty wife. I lead the life of an upper middle class guy. I grew up in a small Texas city and had a great childhood. I was a football star in high school and college and dated lots of attractive women. Most people would say my life is ideal. However, I have some secrets. The story begins when m...

Transwood High Pt. 04

by BoobVillian on Sep 12, 2017
Transsexuals & Crossdressers

Christmas is Cumming... Authors note: All the characters in this series are over 18, this is the fourth part of the serious so be nice :-) Sorry for keeping you horny for so long, hopefully this satisfies. The story focuses on our main heroine, and some new/ old faces appear. Enjoy and leave comments! ******************************* 10/12/2016... 'Open u...

The Third Gender

by thbwcm on Apr 22, 2025

In this story, you are allowed to play as a lot of different characters who live in this world (or outside it), like: Arthur, an 18 years old boy who is trying to have a comfortable life, while sharing a house with his futanari mother and sisters, also survives the end of high school, a place with dozens of horny futa teachers and bullies. Lilith, an 18 year...

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Mistress Coco School Wayward Boys

by tawnysuede on Sep 14, 2017
Transsexuals & Crossdressers

Where Boys Become Girls, Whether They Like it or Not by Mistress Tawny Suede assisted by slave Holly Introduction In Which We Meet Rich Bitch Kimberly and Domineering Mistress Coco Kimberly Caldwell's head thrashed about on the silk pillows; a cry of ecstatic pain escaped her luscious lips as she cupped her heavy breasts, her crimson fingernails ra...

Wendy Wallin

by Musictaker on Apr 22, 2025

My name is Wendy Wallin and I am a Shemale. I've always been a bit on the heavier side and not just my ass and titties. Calling me chubby in high-school would have been generous, and oh boy were the girls of an all girls high school not kind to the only Shemale and person with a penis in the school. After everyone saw me pop a stiffy during gym class being c...

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The Arms Of A Woman

by Samuelx on Sep 13, 2017
Transsexuals & Crossdressers

San Francisco. Mariah walked out of the Bordello. She was getting sick and tired of that place. Sick and tired of working endlessly to satisfy the depraved desires of those people. How she loathed them. Since she began working at the Bordello, she had seen a side of humanity she had never thought was possible. The worst imaginable side. She was just anoth...

Shemale Surprise

by silkstockingslover on Oct 21, 2019
Transgender & Crossdressers

SUMMARY: A married man is seduced and taken by a friend of his wife's. EDITING THANKS: Thanks to Robert, goamz86 and MAB7991. NOTE: This story is dedicated to Robert who requested the fantasy...sorry but the story ended up a lot longer than originally planned. ***** "You can stay with Robert if you wish," Mary said on the phone. I looked up from my lapt...

Male or Shemale, Still a Slut

by yeaimbored on Sep 11, 2017
Transsexuals & Crossdressers

So this is a 2 part story. Part 2 is strictly shemale and takes place a few years after Part 1. Part 1 is how Brandon became Brenda, although without the "I took bath and did my nails and shaved" stuff because that's not my thing. It's more tranny sex than anything, so if you're only looking for full on shemale skip to Part 2, they're pretty much standalone...

Shrunken at home with Futanari Sisters

by starwarsalpha1 on Jan 22, 2021
Transsexual

With the blessing of Mr.z I am transferring his story "Shrunken at home with Shemale Sisters" to this site. First thing you may have noticed is I changed the name slightly. I just like Futanari better than Shemale personally. If you know the original then you know the ages where lower then what this site allows, so I've gone to the liberty of uppin...

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