Shemale School Stories

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Infinite Scroll

Stepdaughter vs. Babysitter

by Derek on Jun 7, 2005
Interracial

Rodney Cox is not happy to hear that he is going to have to stay late working at his shitty job tonight, especially since his wife is out of town on business and that means finding a babysitter for the kids. Of course his first thought is his stepdaughter Lindsay, but as was more and more common these days she is entirely unhelpful. "Hell no, Rod, I've...

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Laura and the Masseuse

by LadyDust on Jul 25, 2004
Erotic Couplings

Laura threw her keys and mail on the hallway table. It was another rough day at work. Nothing like deadlines and the boss breathing down your neck. Upon taking her shoes off she glanced in the mirror, her long strawberry blond hair was out of place and messy, not to mention that her eyeliner was smudged around her gray/blue eyes, she never had the time at wo...

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Movie World

by kaylaiswicked on Dec 4, 2003
Erotic Couplings

Tami and Brad couldn't believe their luck. Just before the new 24-screen multi-plex entertainment center outside Apple Ridge opened, the owner, Mr. Mullins called them and offered them special jobs. Tami and Brad, like half the other kids at Apple Ridge High, had applied for jobs months earlier when construction had begun, but this was too good to be true. M...

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That's not what I heard

by Se7en_Sins on Sep 16, 2020
Fetish

That morning was like any other. A bunch of drunken assholes staying over at my house. Not that I invited any of them to come over and drink. That would be my obnoxious older brother. I'm Mark and I'm an 18 year old high school senior. My brother Jake is also 18, but he came about 3 minutes before I did. Anywho when your parents are gone all the time you pre...

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Big Booty Goth BF

by Furry-god69 on Dec 7, 2020
Transsexual

You are Damien Smith a 18 year old high school senior who's really into goth culture, your parents say it's just a phase, but you don't think so. you look like a regular teen save for you're dark hair, and very feminine figure. For as long as you could remember you always a very girly frame, which many people made fun of, except for, Avery, the love of your...

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College Cuckold

by LennyVanBeethoven on Dec 18, 2020
Miscellaneous

My parents dropped me off during move-in weekend right before classes started. I decided to go to a state school several states away, just to put some distance between me and my hometown. Not that I had a bad time growing up, but I needed a fresh start. I wanted to go where nobody knew my name. Now here I am: all alone in my college dorm room. My roommate St...

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Stormfeather Ch. 11

by TaLtos6 on Sep 18, 2017
NonHuman

Along with Elsbeth, Amy spent the evening and the next morning in preparation for Judge Blake's arrival. With the measurements that she'd taken, Arn had a decent shirt and a pair of pants which fit -- more or less - to begin with, but Elsbeth had proven to be a very handy and knowledgeable seamstress in her way, so Amy was pleased with how he looked. Elsbeth...

Problems Shared

by Cromagnonman on Sep 16, 2017
Romance

This is basically a rewrite of a previous story, 'A New Beginning' It has been fleshed out and a different ending added, to please those who told me that the previous ending was rushed. I'll probably be criticised now for drawing it out too long. Ah well, you can't please them all. CM * She was a pharmaceutical blonde, of that I was almost certain, she was...

Teacher, Teacher Ch. 02

by Malomar on Sep 11, 2017
First Time

It is assumed that you have read Part I before reading this but just in case, this fictional account takes place in the late 1960s. * I awoke Sunday morning to bright sunlight streaming through the open window and stretched my tired and surprisingly sore body, my morning wood quickly bringing back memories of yesterday. I stroked it a few times, my hard-on...

Dana's Side Ch. 04

by JayDavid on Sep 14, 2017
Erotic Couplings

Wednesday I had a test that morning, so I got up early. I ate breakfast, then went upstairs to shower. Before I did, I put on some shiny red lip gloss and took a closeup of my lips. At exactly 8 am, I texted the picture to Jack, with the message, "7 hours." In the shower, I shaved off my pubic hair, as a little extra surprise. After my shower, I dressed f...