Sissy Academy Stories

10,735 results
Orientation
Length
Source
Infinite Scroll

Lexi's Interview

by Jemina004 on Mar 17, 2020
Transgender & Crossdressers

October 5th, 2063 Lexi reached for his purse and took out his compact mirror. Mostly out of nervousness, he had to check his appearance again. Alexandra St. Claire was sitting in the waiting room for Carter Logistics on the 56th floor of the MacArthur Building in Chicago, trying to get one of the most coveted jobs available for white bois these days. Being...

My New Daddy Ch. 04

by sissytoy20 on Mar 6, 2018
Transsexuals & Crossdressers

I got out of the shower Saturday morning, my cock hard as a rock in its cage. I loved how it bobbled on my crotch like a piece of jewelry. That was all my cock was now - a decoration. My asspussy was my real sex organ and I hoped it would get a hard workout today. I dried my cage and put my butt plug back into my freshly washed ass. It slipped in easily thi...

The academy Ch. 01: Setting the tone

by wood_elf on Apr 28, 2020
Transgender & Crossdressers

Synopsis: -A young elf femboy with an unhealthy ego is dominated by his orc roommate. A Lot of sexual adventures involving magic ensues. Notes: -This chapter contains domination, reluctance, subtle foot feteshism, as well as excessive descriptions of jewelry and magic. * Chapter 1: Setting the tone. Ellian leaned over the deck of the ship as he watch...

The TGirl Academy

by noodneighbor on Sep 16, 2017
Transsexuals & Crossdressers

To see where this all started read This Thing Called Life ***** There were twelve of us men in the bus on the way to the TGirl Academy, Tree's Girl Academy officially. It was named after Tree, the enormous black man with the largest cock I had ever seen in my life including pornos. Tree had identified something special in each of us and had managed to turn...

A Sissy Saga Ch. 02

by Snurge on Sep 15, 2017
Novels and Novellas

When Jennifer went out onto the terrace William was nervous but relieved to be with someone his own age and gender, even if that person had been sissified just like himself. The two eighteen-year-olds regarded each other and their feminine attire silently for a moment before Archie at last broke the tongue-tied awkwardness. "Better make a start," he said,...

Mistress de Sade's Sissy School

by spitzharder on Sep 16, 2017
Transsexuals & Crossdressers

My whole body hurt, everything, both inside and out, the pain had brought me agonisingly awake. I could feel the bars of the cold cage I had been thrown into, it had been my home for several months but the beating was new. The other sissies had turned on me, they might be 'girly' but they were cruel, Mistress Kayne had warned me that to disobey one last ord...

Nikki Goes to College Ch. 03

by Latexsissy69 on Sep 25, 2017
Transsexuals & Crossdressers

Sorry it has been so long for a new update to this story, I have been 'tied up' with life, you know how it goes. ***** Quite a few months have passed since I have been enrolled at Primpington Academy, almost a year. I seemed to be taking to this new lifestyle quite well. I was the top of all 8 of my classes that were required of the girls that matriculated...

The Secret of the Island Pt. 04

by neoview on Oct 30, 2018
Sci-Fi & Fantasy

You thought the story had died but it was just my lazy ass refusing to continue. Also I was busy with my girlfriend so I couldn't really focus. Yes, I have a girlfriend now. Well "she" prefers to be called a girl even if she isn't. Without her I would finish this story much faster, but... she gave me some interesting ideas which were too good to ignore. ***...

Futanari Academy Ch. 08

by TheOrcKing on Jun 5, 2019
Transgender & Crossdressers

(All characters participating in sexual activity are age 18 or over.) This chapter is a repost, it has been edited and has undergone very minor rewrites for style and flow. Nothing in the story has been changed. ***** "Pull the lead out of your ass Surbrina!" Miss Angeli barked, blowing her whistle. "You're a Nazi, coach!" Surbrina whined as she moved th...

Nikki Goes to College

by Latexsissy69 on Sep 25, 2017
Transsexuals & Crossdressers

When I was younger I used to be a complete bully. I used to make fun of the poor people that couldn't afford to buy new clothes every school year. There were also times that I would make fun of girls that didn't want to participate in gym class because they were wearing a dress. I used to agitate so many people that I would get into fights almost daily. One...