Sissy Academy Stories

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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."...

Black Sissy For White Queen

by Samuelx on Sep 16, 2017
Interracial Love

I feel so damn great as I slide my strap-on dildo deep inside Ramon Jones. The six-foot-tall, skinny Black guy looks absolutely gorgeous in a bright pink dress, white pantyhose and high-heeled red shoes. His face is perfectly made up, rouged and his makeup and lipstick are applied nicely. The fuzzy black wig he's wearing only adds to his decidedly not so mas...

Naruto: Sissy Shinobi

by CuriouslyWatching on Apr 22, 2025

Naruto wasn't sure what he expected from the being a ninja. But being forcibly turned into a sissy or being sexually taken advantage of wasn't anything he had planned for. ㅤ ㅤ ㅤ ㅤ ㅤ ㅤ ㅤ *Please feel free to add your own chapters, unless they break the TOS or have major grammar issues they're fine* *All characters in this story are at least 18 years old*What'...

The Vassal Academy Ch. 22

by SavannahMann on Sep 12, 2017
BDSM

Andre merged into the proper lane and exited the highway near Middleton New York and followed the GPS prompts to the Medical Center. Parking the expensive car in a safe spot, they headed inside. Geneva took the lead, having spent far more time in Hospitals than Andre had, she oriented herself quickly, and after getting the room number from the information...

A Sissy Saga Ch. 01

by Snurge on Sep 13, 2017
Novels and Novellas

The schoolgirl is wearing a gymslip of such a dark shade of blue it appears almost black. She is bending forward and stretching across a small table that boasts a cover of purple chenille, resting the flattened palms of her hands on the hard surface and pressing one side of her flushed face between them. The back of her skirt as been folded up to her waist a...

A Sissy Saga Ch. 16

by Snurge on Sep 15, 2017
Novels and Novellas

It was after supper, but the evening sun still shone through the lofty windows of the gymnasium to catch dust particles floated weightlessly in its slanting streams of light. A naked young man who promoted the delicate aura of a fragile girl stood fumbling over his words before the seated figure of Miss Twist, groping helplessly for an excuse to explain the...

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,...

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...

Welcome to Sanctuary Academy

by ChaosMage on Apr 22, 2025

Welcome to Sanctuary Academy a special school within the Futadom Empire that trains young men and women to be the perfect submissives to the superior Futa Race. Within the Futa Empire the third gender of Futa are superior to regular men and women who exist almost solely to be cock sleeves and sex toys. Futa's love to have specially caught males as their toys...

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...