Sissy Stories

Pretty simple, I asked AI for a few prompts where a man finds himself wearing a diaper and girl clothes: It spit out a few prompts, then I asked it to write a story. At...

Timothy was a homeless guy until he was offered to live with a rich couple with spare bedrooms. He's hired to work with Mitchell, a violent son of the billionaire and...

This is the story of a 19-year-old boy who had to accompany his aunt and cousin on a vacation to their summer home. The boy in question is named Sander. He had hoped to...

Tom is blackmailed by his roommate to pose as his girlfriend. This helps Tom discover he was born to be a sissy slut.

(HEAVY SUBMISSION THEMES, 18+!!) Oliver, a sophomore at Westbridge University is a bit of a creep and finds himself irresistibly drawn to the girls' volleyball team at h...

this is the story of how Tim became Kim and found her true sissy calling: as a slutty college cheerleader! ** 18+ ADULT CONTENT WITH THEMES OF HUMILIATION, DOMINATION, A...

Scott, an 18-year-old boy from Ontario, Canada, is excited to participate in an exchange program and experience life in England. However, upon his arrival, he discovers...

When mischievous younger brother, Danny, steals from his older sister, Katie, she decides to teach him a lesson. However his response to the lesson takes an unexpected t...

Eric comes home to find a delightful surprise where he gets to meet his 'mother' in a new avatar and role!!! A delightful crossdressing tale of a amab daughter and moth...

Adam is in desperate need of money and finds out about The Sissy App, an app where you can play games and do challenges for rewards. However, Adam doesn't know the app h...

jake is a normal 15 year old boy who is staying at his aunts elizabith she has a daughter named hannah and a son named luke

the latest installment of a sissy trip down the free use rabbit hole

jack has to move university due to problems at his old one, as he moves into his new accommodation, some changes happen

Dana, who despite the name, is all boy. Finds himself an unhappy fifteen year-old camper at an Girls' Summer Camp. And there he must remain till summer's end, with his m...

VICTORY OF KILLSTREXK. B short story collection. Released: September 2, 2023

questo ragazzo di nome Leonardo/Leo viene bullizo per 3/4 anni dopo l'ultima goccia decide di porre fine alle sue sofferenze prima di farlo incontra una donna che cambia...

Jonah will do anything to get away from grandma's photo albums and at least his cousins have imagination!

Andrew is an 11-year-old boy who is part of a superhero family. However, he is not allowed to join them when they save the world. This is so frustrating that he becomes...

Florian (Ian) Flint has agreed to his Aunt to be her flower boy for the wedding. Ian spends his time helping his Aunt and having wild dreams about what his life is like...