High School Sissy Stories

209,604 results
Orientation
Length
Source
Infinite Scroll

Made Over Ch. 03

by gbr2004 on Sep 15, 2017
Fetish

This story involves forced cross dressing, gay sex and bdsm scenes. Don't read if not into these scenes. * I had met a man in my apartment building and he had invited me to join him at a club he goes to in LA. I was a naive boy from Kansas attending USC and I had no idea what I was getting into. The club ended up being a gay leather bar and before the nigh...

Our Conquerors, Our Concubines

by Shendude on Dec 20, 2010
Science Fiction

Millenia ago, an alien race created the Ghirabo, telepathic shapeshifters intended to serve as sexual playthings, able to read their owners' minds and assume a form and personality that will fulfill their owners' desires. But the Ghirabo's Creators were wiped out, leaving them to fend for themselves. In time, the Ghirabo have become a powerful race, creating...

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Jamie Becomes Herself Ch. 01

by heavyandhorny on Sep 14, 2020
Transgender & Crossdressers

It was almost midnight and my computer was flashing bright images in front of my eyes. The screen showed cocks, and porn stars and suggestive words overlaid together to make me fall into a sort of trance. The hypno continued to play and my little cock grew in my hand, my balls were contained by the panties I had pushed down. I rubbed my 4 inch cock harder an...

Lace and Love Ch. 03

by vaultdweller111 on Sep 19, 2017
Transsexuals & Crossdressers

Jake Orlov grabbed his duffle bag and rifle case out of the cab of his F-250. He had some other gear in the truck, but he decided to get the rest later. He was exhausted from driving back from Kentucky, training the Blackwell county sheriff's department's SWAT team for the past week. Jake was disgusted at how these guys managed to graduate the police academ...

The Wedding Ch. 04

by betamale08 on Mar 30, 2020
Transgender & Crossdressers

The Wedding (Patti Cake part 3) Chapter 4 -- Teaching, Teasing and Testimonials... I was a little stunned and leery after reading my version of this contract which wasn't all that different from Patti's... From changing my name to rescinding my rights to wear male clothing while in the employment of Darren and Carol -- or Ma'am and Sir, and also, not to f...

Clara Bow's Academy for Ladies

by Sputnik57 on Sep 15, 2017
Transsexuals & Crossdressers

Peter had had no choice in the matter from an early age. As he car drew up to the huge ivy clad castle-like building, having entered through electronic gates in a ten foot wall, he felt doomed yet excited. His cock was erect in the tight panties his Stepmother has chosen for his introduction, his anus tingled and gripped the soft rubber plug she'd also chose...

A Tale of Two Sissies Ch. 01

by SatinSlip on Mar 26, 2019
Transgender & Crossdressers

Author's Note- this story is a work of fiction. All the characters are eighteen or older unless noted otherwise. This story contains scenes of non-consensual sex, incest, interracial sex, gay sex, forced feminization, abuse, and rough sex. I hope you enjoy reading it as much as I enjoyed writing it. - ***** SMACK! My cheek stings from the big black te...

A New Way Of Life

by blackdog27 on Sep 14, 2017
Transsexuals & Crossdressers

This story begins as many do. I stared to dress at an early age in my mom's things. Then I started to buy my own things as I got older; panties, bras and high heels. I was always small for my age taking after my mom, she was a small woman with a nice figure and so was I. I was only 5'4 and 110lb, blue eyes and jaw length blond hair. They loved me in high sch...

A Prom Queen Fantasy

by bluesbirds on Jul 15, 2020
Transgender & Crossdressers

"Aww, isn't this little blue number cute?" Tanya squealed from the other side of the rack. I flinched hearing her voice; we had been shopping for almost 3 hours without a break. This was the first time I had gone shopping with Tanya since she found out about my crossdressing fetish. "Come to this side - let me hold it up to you," she demanded. I meekly co...

A Letter to Our Pantyhose-Sissy

by Sheermistress on Sep 19, 2017
Transsexuals & Crossdressers

I'm on my bed on my knees, my skirt pulled tight and just a little high, exposing my control-top pantyhose to your eager eye. My feet are dangling over the edge of the bed and you, my little pantyhose-slut, are standing behind me, dressed in your sexy schoolie outfit and mary-janes. Your face is made up in a prissy, sissy, teen-girl way and your hair is fini...