Shemale School Stories

106,125 results
Orientation
Length
Source
Infinite Scroll

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...

The Devil's Harem Outfit

by Miles63 on Sep 18, 2017
Transsexuals & Crossdressers

Author's Note: Hey guys, when I was finishing my last story I found a file with this story half finished and I thought, what the hell lets finish it. Now this is a very very dark story with strong erotic horror themes that some may not find pleasing. There is some strong incest thrown in too. If you are not into that this may not be the story for you. Other...

Transwood High Pt. 01

by BoobVillian on Sep 16, 2017
Transsexuals & Crossdressers

The Shemale Bully Authors note: All the characters in this series are over 18, this is my first ever story so be nice :-) The story has a few main characters, which will be introduced over the course of the stories. ***** WAH WAH WAH WAH WAH!! Lauren groaned as she rolled out of bed and turned of her alarm clock. The day she knew she was coming all summe...

I Meet a Well Endowed Shemale Milf Online

by Jamesw324 on Sep 13, 2018
Transsexual

I let out a long sigh as my computer began to boot up, "Well I guess I will check my messages again." Hello there my name is Alex and I am a high school graduate living at my moms house to take a break year. This year I need to find work and hopefully a girlfriend. It was at the start of this break when I stumbled upon this sight called: Shemale me...

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Connie at an Adult Bookstore Ch. 01

by cmorehead on Sep 13, 2017
Transsexuals & Crossdressers

Disclaimer: The following story is not intended for minors. If you are offended by sexually explicit material or it is not legal in your place of residence, please close the document now. If not, I hope you enjoy my attempt at entertaining you with stories of my adventures. * Let me start by introducing myself. My name is Connie and I am a 40-something tr...

Finding My Shemale Goddess Ch. 01

by TheGuyInBlack on Sep 11, 2017
Transsexuals & Crossdressers

Hi, and thanks for reading my first ever submission on this site. I want this to be a multi-part series, so if you have any suggestions I'll be happy to read them. Also, I'd be grateful for any constructive criticism you may have. Thanks again for reading and enjoy! -TheGuyInBlack ********** My hand was trembling as I knocked on her door, I've never been...

First Time with a Shemale

by BigAndy922 on Sep 13, 2017
Transsexuals & Crossdressers

I was living in LA and pretty fresh out of school, not to mention pretty naive in the peripherals of human sexuality. I'd been with a few girls growing up, but nothing ridiculous. I liked going out with my buddies, and we'd drink and there was the occasional recreational use of ummm, how should we say... party favours. I liked my share of porn, and as I had...

Shemale Beauty: 1st Female Conquest

by silkstockingslover on Sep 13, 2017
Transsexuals & Crossdressers

Summary: 18-year-old discovers her powerful sexual persona. Note 1: This is the first of potentially many shemale stories starring the beautiful seductress Kara... Note 2: Thanks to... Tex Beethoven, Robert, and David for editing this story. Shemale Beauty: 1st Female Conquest Everyone has hobbies. For most people, hobbies can be activities like trav...

Neighborhood Good Boy

by Kami107 on Feb 13, 2020
Transsexual

Brian had recently turned eighteen, he was finally a man. Although he didn't quite feel it. He was much smaller than the other boys around his age being only 5'4" and weighing in at a measly 120 lbs. With black hair, pale smooth complexion, skinny but proportionate limbs and wide hips that contoured his firm bubbly butt, his effeminate features didn't q...

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Sister's Shemale Friend

by silkstockingslover on Sep 12, 2018
Illustrated

Sister's Shemale Friend Summary: Family seduced and dominated by an irresistible shemale. Note 1: This is a Summer 2018 Contest Story so please vote. Note 2: Thanks to DarkBreezly for creating the pictures in this story. Note 3: Thanks to Tex Beethoven, Robert and Wayne for editing this story. I came home from work a couple hours early, as our manager...