Sissy Boarding School Fiction Stories

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Infinite Scroll

Welcome to Sanctuary Academy

by ChaosMage on Apr 22, 2025

Welcome to Sanctuary Academy a special school within the Futadom Empire that trains young men and women to be the perfect submissives to the superior Futa Race. Within the Futa Empire the third gender of Futa are superior to regular men and women who exist almost solely to be cock sleeves and sex toys. Futa's love to have specially caught males as their toys...

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The Office Sissy XX Ch. 02

by pennyjonestv on Sep 15, 2017
Transsexuals & Crossdressers

CHAPTER 3 The smell of Dannie's pheromones was making me giddy. It had been so long since I had last tastes sissy clitty; too long. My mind flashes back to boarding school, Gloucestershire. I was young, under age by English law. It was just after the summer play, and James had decided we should change costumes; boys wear the Shakespearean dresses of the gir...

A Sissy Saga Ch. 10

by Snurge on Sep 15, 2017
Novels and Novellas

"Disgusting!" exclaimed Miriam Hancock lightly as she examined the photographs Emma Twist handed her. It had taken Hardwick most of the day to produce the prints, but they were well worth waiting for. The headmistress went through them as if shuffling cards, and having glimpsed each one viewed them a second time, more slowly and with greater concentration. "...

Letter from Carker's Rents

by justincbenedict on Sep 24, 2019
BDSM

Dear Shoeblossom-- Since I taped this, I also have enslaved my brother-in-law Santiago and his basketball team. So I have real progress going on here in Carker's Rents! Love, Sugar Perez "Sugar, I am having a devil of a time getting these thorns out of my, um--" "Your diaper. Say it, Esteban." "Don't--don't you think it was punishment enough for me to...

The Vacation from Hell Pt. 02

by JamesMiehoff on Dec 11, 2018
Erotic Couplings

Copyright (c) 2018 James Miehoff, All Rights Reserved. This work may not be published whether for fee or free without this copyright. --------- This is one of a series of stories set in what I call Universe-J. Universe-J is very much like this universe with a few exceptions. First the people tend to be a little more sexual and less hung up on sex that...

Ikuji Nashi

by SissyCockWorship on Jan 21, 2018
Science Fiction

As you sat staring off into another world, you could hear your stepmother arguing with your high school principal. You took a deep sigh. This could not be happening. You had a legitimate shot at making the high school lacrosse team your freshmen year. Now it looked like more and more that it was going to be that weird boarding school. Ikuji Nashi. Ikuji Nash...

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The Journey Ch. 02

by born2srvtv on Sep 19, 2017
Transsexuals & Crossdressers

(You may want to read The Journey before reading this so you will know the background of Tom/Tonya and Jason. These stories are a combination of real life and fiction. Thanks for sharing your comments.) Tonya was content as she stretched across Jason's lap. She had given Jason a long slow blow job and now Jason was rubbing his sissy slut's smooth ass a...

Sissy Maid Son Pt. 01

by Robyn228 on Jul 16, 2018
Transsexuals & Crossdressers

Editor's note: this story contains scenes of incest or incest content. ***** Note: This story is entirely a work of fiction, and should only be viewed as a fantasy. Any similarities to actual events or people are entirely coincidental. All characters are over 18. ***** Peter walked into his house, feeling excitement clenching in his stomach. He's been pa...

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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Pearl Ch. 02

by allourdesires on Oct 22, 2019
Transgender & Crossdressers

The fact that Her boyfriend would be coming over to my flat, on the evening of my birthday, to bring Lori out was enough, of itself, to overshadow my whole week but, add in the fact that she had told him all about my crossdressing and our relationship and I would have spent the entire week cowering in my room! I think Lori realised that her actions had inst...