Sissy Sanatorium Stories

6,613 results
Orientation
Length
Source
Infinite Scroll

The Tenth One

by thechangedone on Sep 14, 2017
Transsexuals & Crossdressers

Chapter One: Business as Usual Waverly Hills Sanatorium. Present Day. "I told you to be careful!" a guard exclaims. "This isn't your private presidential suite, for God's sake!" "Hey!" the second guard retorts. "It's the first time I spilled my coffee!" "Clean it up before the shrinks see us," the first guard continues. "Nobody's gonna come here!" repl...

The Sanatorium Pt. 01

by clemencejones on Sep 19, 2017
BDSM

My wife, Julia, and I have been married for three years. Lately she mentioned me more and more that I look at hot girls on the street and she became furious when she's heard rumors about me and a single colleague of mine. I always replied with that my eyes did not take a vow of loyalty, but it only made her angrier. One time she came up with this: – My frie...

Saint Michael

by miedsal on Sep 17, 2017
Non-Erotic

This story is told from the point of view of two people, Michel and Sally. Each section is prefixed by name. It is written for my enjoyment and hopefully yours as well. ----- Michael: They call me Saint Michael behind my back, some with reverence, some with disdain and others with suspicion. All have a theory about my past but no-one knows the full story...

Hotbeds Ch. 11

by NormaJane on Sep 14, 2017
Erotic Couplings

CHAPTER 11: MATRON Introduction: The sexual adventures of a prep school teacher in the 1950s and 1960s. Chapter 11 finds him back at his school after an intense month of sex, reported in Chapters 9 and 10. The latter records the consummation with Denise of their activities in Chapter 1. ***** As soon as Denise left I packed my few belongings into the sad...

Minerva Ch. 09 of 10

by Denham_Forrest on Sep 17, 2017
Non-Erotic

For the rest of that day, nothing happened, well nothing of significance anyway. Except maybe, that I had apparently become, Lady Tanya's close companion. Or rather, being the only... non-professionals around, we seemed to spend all of our time together. Lady T insisted that I escorted her almost everywhere. Walking stick in one hand, she hung onto my arm li...

Avenging Mother-in-Law

by dass4450 on Sep 12, 2017
Mature

Mary Jane had been pleasantly plump when he married her. She had been a joyful, bubbly soul with a generous smile and a non-stop urge to fuck and suck. Ten years on, frustrated by her inability to have children, she suddenly turned on herself. He watched, helpless, as she drove herself on diet regimens that reduced both her bubbly body and personality to a s...

Sexual Education

by shambles on Aug 31, 2017
First Time

My early education was supervised at home by a tutor. I had qualified for university entrance by the time I was fifteen, so I suppose they would call me a nerd nowadays. Anyway. when I was seventeen my father decided that I should enter a seminary to finish off my education. Saint Nicholas was renowned for a high academic standard and firm discipline, and mo...

The Doctor is In Pt. 03

by limeybato1 on Apr 9, 2019
First Time

I apologize to my readers. I incorrectly referred to a cervix as a hymen in my last missive. My mind doesn't work so good these days that's why I'm writing this down. When I have an erection I have even more trouble... So please forgive me. Anyway, I hope no one is reading this as prep for their medical exams! Talking about hymens reminds me of this story...

Night of Many firsts Ch. 01

by DonAbdul on Sep 1, 2017
Group Sex

She was engaged to be married, but a couple of weeks to the wedding, her whole world came crashing down around her, when she received an anonymous tip that took her to a motel on the edge of town. At the motel, she caught her man, and her would-be maid of honour, stepping out from a raunchy fuck fest..... The trauma of that incident and the heartbreak it ca...

Superheroines Bk. 09

by drsnip on Sep 19, 2017
Sci-Fi & Fantasy

WARNING... This is an "Erotic" Science Fantasy story. If you are offended by commonly used sexual words and graphic descriptions of various sexual acts then stop reading this now. There are countless Alternative Universes, ranging from ones that are almost indistinguishable from our own, to ones that are totally unrecognisable from our own. Somewhere/time...