Stories About Sissyboi Academy Stories

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Sam's Story Pt. 09

by Shadykingcolor on Jul 6, 2020
Fetish

As I sat in the basement...the dungeon, contemplating my new life as "Trisha." Mel's anger. She knows about Cassie. How my life is forever changed, I ask myself "was it worth it?" The door creaks open. Someone begins to descend down the stairs. It's Cassie, holding a cup and saucer. "Tut tut tut, Pet. Who's been a naughty little sissyboi." She purrs while...

Sissy Cuckold & The Old Bull Ch. 01

by DirtyDaddyHunter on Sep 19, 2017
Loving Wives

He waited on the bed as instructed. He had dressed exactly as he was asked: A pair of lavender lace trimmed panties stretched tightly over the young man's small cock; a matching bra covered his hard brown nipples too. He also had on a garter belt and some high heels. Too top in off he had on some coral lipstick and he had painted his nails perfectly. There...

Review: The Academy

by lindiana on Sep 16, 2017
Reviews & Essays

The fourth book in The Marketplace Series by author Laura Antoniou is titled The Academy: Tales of the Marketplace. It is a marked departure from the rest of the series as this is a compilation of short stories by a variety of authors, including Ms. Antoniou and her wife, Karen Taylor. As well, the stories are joined together with narratives supplied by Ms....

Sissy for the Family

by sissyboi4daddy on Aug 21, 2018
Transsexuals & Crossdressers

Hi, my name is Isaac. I'm 21 years old, Asian and a child of divorce. My father decided he wanted nothing to do with me the moment I was born, and my mother held 2 jobs to raise me. When I was 18, she decided she had enough of the hard life and remarried. She remarried Jack. Jack was a white, bordering on obese man, who was 12 years older than my 42-year-o...

The Uniform-Snatchers.

by DMozarella on Oct 9, 2020
Fetish

Clothworth Academy has been around since the 1910s, and was home to some of the brightest and hardest-working students in the country. in order to be accepted, each student had to prove that they were worthy by going through a series of exams, each proving that the applicants were smart enough to join the academy. through the 110 years of the school's existe...

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Sam's Story Pt. 08

by Shadykingcolor on Jan 29, 2020
Fetish

As Mel and Steph leave the room only my caged cock is on my mind. It's burning like mad and balls are in agony from the cage. I try to massage my balls where the base ring is applying the most pressure. But having no joy. I get off of the bed, maybe a shower will help. I think to myself. As I start to leave the room I noticed a dildo on the floor. It mus...

Lusty Magical Academy

by Zingiber on Jan 10, 2016
Fantasy

Open for contributions. See the Chyoa Forums Discussion Thread for details and Q&A: http://forum.chyoa.com/threads/lusty-magic-academy-rpg.452/ There comes a time when young people of special gifts come together under the guidance of dedicated teachers to advance their skills, learning, and character so they can use their powers for maximum benefit. Th...

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Student Bodies

on Nov 18, 2016
Fetish

Once upon a time, there was a special school. Let's call it Sheetwood High. It was special because, for a lack of explanation, the town of Sheetwood and even it's surrounding county was a queer place. Many said Sheetwood girls were just different than other girls, and they were right. Because Sheetwood high schools and colleges, should the statistics have be...

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Object-Oriented

by ucakeordeath on Apr 22, 2025

(Cover image credit Undressing by mikehunt2911) Inspired by the works of wandrer, fan no hitori, Leticia Latex, Ice Bear, CarltheCarl, and others, I'll be posting a few very literal objectification stories I've been kicking around for a while, with room for more as time goes on. Feel free to post threads of your own if you feel so inclined. I intend to moder...

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Saints Academy

by dick88 on Jan 6, 2015
Fantasy

Saints Cross Academy is the premiere college preparatory boarding school for the residents of Saint Miller's Crossing for ages (18-20). This schools primary focus is to preparer the newly of age for the rigors of young adulthood. Located a few miles out of Saint Miller's Crossing adjacent to the Federally protected forest lands in the west of town atop of Cr...

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