Sissy Castration X Stories

19,754 results
Orientation
Length
Source
Infinite Scroll

An Obsession

by Marcus_Cicero on Jul 30, 2019
Transgender & Crossdressers

It would have been after that documentary. The one with a feature on online dominance-submission relationships on Fetlife. Because before that moment in time life had been so vanilla. Marcus had been queer and had had a boyfriend or two... or three since turning 18. Well, hell, he'd been to the bathhouses since turning 20. He'd even gone as far as to create...

Hot sister's sick fetishes

by 91timhard on Apr 22, 2025

Since your little sister hit puberty, she got incredibly hot. Her boobs grew to a perfect size and shape, her has is round and spankable. Her skin is incredibly smooth and her legs are long for her short stature. You feel ashamed every time you fantasize about her. But you just cant help it. One day your horniness gets the better of you, and while she is in...

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Miss A's New Play Thing Pt. 04

by Pornenthusiest on Mar 2, 2020
BDSM

Recap: Miss A had just finished a luxurious bubble bath and was returning to her slave who was chastised and gagged with her pantie hose and a ball gag, with Miss A's wetted panties draped over his nose. Locked away in her dungeon, after an arduous breath control play session, her slave was spread wide at the ankles with a spreader bar, bent at the waist wi...

The Black Doctor & My Wife

by GeraldG on Sep 26, 2017
Interracial Love

The Doctor - Or How My Wife Became a Black Cock Slut I was in the kitchen preparing some goodies for everyone to snack on. People do get hungry from fucking so much. I was naked except for the lacy, frilly apron that kept my little dick from getting splashed on. The apron was embroidered. My wife, Lorna, at the prompting of one of her black lovers, Doc, m...

Virgil's Adventures

by SilasCrowley on Nov 6, 2019
Fantasy

The furnaces of Baddock billow with smoke ahead of you, downhill. It is not a pretty place to look at: although most buildings are masonry and concrete, you can see even from almost two miles away how they're held together by huge bands of steel and joined by metal bolts, all of which are rusted to varying extremes. The weathered frontier town looks slumly b...

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Aztec Art - The Path to Submission Ch. 07

by Sputnik57 on Mar 20, 2018
BDSM

Lloyd had been treated to a gratuitous and well received whipping by Joyce, watched by Patti, Kay, and Maria, who noted the pleasing sign of a boning erection as his wife confirmed her new status as his owner, then was bundled into a walk-in wardrobe at Patti's house, trussed with his head down to await their further pleasure. He was not alone in the wardrob...

Demi-Monde Barber of Fleet Street

by skriblur on Sep 14, 2017
Transsexuals & Crossdressers

Episode Three: Mrs. Henderson & the Demi-Monde Barber of Fleet Street The story picks up from the end of "Mrs. Henderson Plays Matchmaker". A sissygurl and a tomboy are together on the couch, the sissygurl's face in the tomboy's lap. Or maybe it's the tomboy's face in the sissygurl's lap. It works either way. There's also a third and fourth little pretty;...

XChange Seminar, X-change, X Change Ch. 02

by Grabenork on Feb 6, 2018
Transsexuals & Crossdressers

"Good morning, everyone! I am Dr. Welcott, and I am very happy to welcome you to X-Change Technologies, Inc. You are all here because you attended one of our X-Change Seminars run by Dr. Brewer at the Comstock Institute. He reports that you all participated in the seminar enthusiastically and then signed a list to volunteer to become future demonstrators at...

A Dream Come True Ch. 01

by severomi on Sep 18, 2017
Transsexuals & Crossdressers

This is a two part story. Part I is reality and true while part II is my Dom's dream. PART I - The truth I'm an American abroad, been in Europe most of my life, now 58 years old and have been married twice with little success. I decided to change what I'm looking for, after having reflected on my previous relationships, where I had also two TG/TS relatio...

Twist

by Seurat on Sep 12, 2017
BDSM

Once, long ago, I got fed up with the way femdom, forced transgender, and loving wife stories with BDSM basis ended; they had grown very predictable. In fact, a few authors had posted short lists of vignettes which, unintentionally, encompassed all of the common endings which I had grown to abhor. My own list, a response to the predictability of those storie...