Sissy Academy Stories

10,735 results
Orientation
Length
Source
Infinite Scroll

Lace and Love Ch. 03

by vaultdweller111 on Sep 19, 2017
Transsexuals & Crossdressers

Jake Orlov grabbed his duffle bag and rifle case out of the cab of his F-250. He had some other gear in the truck, but he decided to get the rest later. He was exhausted from driving back from Kentucky, training the Blackwell county sheriff's department's SWAT team for the past week. Jake was disgusted at how these guys managed to graduate the police academ...

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...

Beta Male Slave Academy Ch. 01

by Tazokm on Jul 13, 2020
Fetish

My head was still spinning. I kind of heard what was going on, but not really. "Right, Patrick?" my girlfriend asked me. I had completely zoned out. After an hour long car ride to a large compound in the middle of nowhere, I had time to contemplate what was going on. Still, my girlfriend telling me she wanted to have me trained to become a slave was very pu...

Lucian Ch. 10

by angiquesophie on Sep 14, 2017
Transsexuals & Crossdressers

How to win a fight if all you know is to be charming, sweet and graceful? The room was large and stately. It was a drawing room, really, with paneled walls and high, shuttered windows. The scent of polishing wax reminded Lucian of Bobs working hard to clean it. Maybe the place served as a conference room; or even a boardroom with its huge, shining table...

The Bevington Academy Ch. 02

by Sarahk100 on Sep 13, 2017
Transsexuals & Crossdressers

The following story is based on the Bevington Academy captions written by ;) The Bevington Academy Files: Danielle Grant: Chapter 2 Day 3 We all woke at 7 AM again. I rubbed my eyes and scanned the room. Yesterday all the guys were wearing the uniform I was now putting on myself. But Andrew was now wearing what the boys like Jenny was wearing. He looked a...

Beta Male Slave Academy Ch. 02

by Tazokm on Jul 13, 2020
BDSM

After being blown and locked, Miss Carly explained to me that the compound we were at had over a hundred rooms and approximately 50 current residents. She began walking me to a room where I was to keep myself preoccupied until they had prepared my sleeping arrangement. I walked butt naked behind Miss Carly down a high-ceilinged hallway. Her ass was absolutel...

Letter from Annapolis

by justincbenedict on Sep 26, 2017
BDSM

Dear Shoeblossom: I've always known I was a bad boy. My Mother used to get so mad at me...she'd want me to spend time with my sisters, and help polish the silverware...she'd shake her head because I didn't want to play with paper dolls...I wanted to be like my macho father. Mother had strawberry blonde hair in a bouffant hairdo, and what they used to call...

Separation Trial (Trial Separation)

by fetisha_44 on Sep 2, 2017
Fetish

We had been married about three years, when my wife and I decided that it just wasn't working. We agreed to a "Trial Separation" with the proviso that we could see others if we wished to, but somehow I didn't think that Gayle would do anything about it in a physical sense. I had always been a gentle lover, and she seemed like the quintessential "ice queen."...

Futanari Academy Ch. 14

by TheOrcKing on Jun 10, 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. Halloween Special, 2018 Danielle walked up the steps to her friend Maddie's house, still wearing her Westbrook school uniform which now consisted...

Black on Black Pegging is Okay

by Samuelx on Sep 11, 2017
Erotic Couplings

Romulus Stephen sat in his bedroom in the small apartment overlooking The Park in Vanier, around the eastern bend of metropolitan Ottawa, Province of Ontario. The big and tall young Black man sat at the computer with his pants down, and furiously stroked his dick. On screen, a sexy Black woman was banging a slim White guy in the ass with her strap-on dildo....