Feminized Sissy Stories

6,870 results
Orientation
Length
Source
Infinite Scroll

The Society Ch. 05

by Barno on Sep 19, 2017
Transsexuals & Crossdressers

"I don't think that I'm the right person for this. You need someone more experienced. What if I fuck this up? I'll get my balls snatched right out from under my cock!" I was more than a little nervous watching Serena and Corinna rifle through my closet. "Your balls were snipped off quite a while ago my dear and the woman who owns them has given you her orde...

Humiliation Journey Never Ends

by Subkoksukr4u on Jun 25, 2019
Transgender & Crossdressers

Here I am once again looking up into the eyes of my tormentor, my superior in every way, especially his cock, 10 1/2 inches to be exact. I know because when I first met him he made me measure it with a ruler. He made me measure mine too. I was embarrassed, humiliated and shamed for being so small. It hasn't been called a penis or anything remotely masculin...

The Feminisation Initiative Ch. 02

by Slipperylock on Oct 30, 2018
Transgender & Crossdressers

The room was quiet and dark - the only illumination spilled from the Observation Room window over the eight beds and their occupants. The only sound in the room was the whirring of the machines, and the occasional muffled moan. In the Observation Room booth, the Director of the F-center fiddled with the control panel nervously and jogged her leg. The Presid...

New Gurl in Town Pt. 01

by GavinIsaNuisance on Jul 6, 2020
Transgender & Crossdressers

This work is entirely fictitious. Any similarities to actual persons living or dead is purely coincidental and entirely unintentional. All characters portrayed in a naked/sexual nature are 18 and up. *** The city of Los Angeles, California. A place once regarded as the focal point for entertainment and movie stardom now reduced to an over-taxed, grimy, dru...

My Therapist's Chinese Doll

by naoko17 on Dec 18, 2018
Transgender & Crossdressers

Disclaimer: The content below has many degrading comments on certain race and sexual orientation, so please don't read it if you are looking for "political correctness". ***** I still re-lived the night Eunsun left me. I remember her blank stare, followed by a cold grin. She wasn't the lovely woman I once loved. She said she didn't love me anymore, and wa...

Mistress Chronicles Ch. 01

by MistressMtoyou on Sep 25, 2017
Fetish

Subject and background. This is a recap of my first in-person session with a submissive. The subject passed the various pre-session requirements described in my second story "A few good subs" and after an extensive interview and evaluation process I offered him the opportunity to do an in-person session. I'll admit upfront that I was a novice at this point...

Cross Dressing: A Hypothesis

by Da_Vida on Sep 16, 2017
Reviews & Essays

First as a young adult and then as a psychologist, I read extensively in an attempt to find an explanation for my cross dressing behavior. Several psychological hypotheses have been proposed in the literature but I did not find any of them to be compelling. While I don't think it is an explanation for cross-dressing, one hypothesis that resonated somewhat...

'Cumshift' World Rules

by AlexRaymond22 on Apr 1, 2020
Reviews & Essays

So far as I can tell, I invented this world. It draws inspiration from a few other ideas, most of them based around the 'sissy' fetish and subculture, but I've never seen it anywhere else, so please accept my apology if the idea isn't as novel as I mistook it to be. The name is likewise made-up, if anything already has the name, I mean no offense by appropri...

Wesworld: Candy's Interview

by gaildaniels84 on Dec 25, 2019
Transgender & Crossdressers

This story is inspired by a series of captions done by Wes Mantooth over on his blog. Wes has been gone for several years and I'm a huge fan of his work so my intent is to use several of his stories and characters as jumping off places to create a larger world. *** Cameron once again ran his hands down the front of his pants, trying surreptitiously to wipe...

Girls Club Ch. 01

by ValerieMay on Mar 7, 2018
Transsexuals & Crossdressers

I stood by the bedroom window, letting the morning sun shine bright lines across my face. I closed my eyes and inhaled deep through my nose as the hazelnut flavored steam from my coffee reminded me of when everything was so ordinary. Ken was still in the shower and I wondered how he would like seeing me in my new XL knit sweater without any pants or underwea...