Sissy Stories

537 Stories

I let AI write my story about a man becoming a sissy by LittleBabyPrinceS
#1
I let AI write my story about a ma...by PamperMe_Literally
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...
Hobo to Dancer  by SissySecretary
#2
Hobo to Dancer by Andrea Green
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...
Sander on a summer vacation  by Shadow_sub83
#3
Sander on a summer vacation by Shadow83
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...
Becoming A Sissy by roundtheoutside
#4
Becoming A Sissyby roundtheoutside
Tom is blackmailed by his roommate to pose as his girlfriend. This helps Tom discover he was born to be a sissy slut.
Oliver/Olivia: Blackmailed Sissy by lilywritesMTF
#5
Oliver/Olivia: Blackmailed Sissyby lilywritesMTF
(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...
Cheer Sissy! by sissy_noel
#6
Cheer Sissy!by 🎀Sissy Noel🎀
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...
The Unexpected Exchange - Forced Fem Fantasy by ameliamaebarnes
#7
The Unexpected Exchange - Forced F...by Amelia Barnes
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...
Becoming Her Little Sister by Carlycurls
#8
Becoming Her Little Sisterby SheWrites
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...
Like Mother Like Daughter  by aishaa2204
#9
Like Mother Like Daughter by Aisha
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...
Completed
The Sissy App by Carlycurls
#10
The Sissy Appby SheWrites
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...
Completed
from teen to a diaper wearing babay by Kevinjones2029
#11
from teen to a diaper wearing babayby Kevinjones2029
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
Completed
SAUNA STORY 5 - proud beta  by tattedthing
#12
SAUNA STORY 5 - proud beta by tattedthing
the latest installment of a sissy trip down the free use rabbit hole
new university by jasonw420e
#13
new universityby jasonw420e
jack has to move university due to problems at his old one, as he moves into his new accommodation, some changes happen
Completed
We're All Girls, Right? by amberwalker365
#15
We're All Girls, Right?by Amber Lynn Walker
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...
B: Short Story Collection by LonelinessRegret
#16
B: Short Story Collectionby ❤️ ⓁⓄⓃⒺⓁⒾⒸⓄⓇⒺ ❤️
VICTORY OF KILLSTREXK. B short story collection. Released: September 2, 2023
l'onnipotente by gachaleo777
#17
l'onnipotenteby Leopardi 123
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...
Playing Princess by AndlatFox
#18
Playing Princessby
Jonah will do anything to get away from grandma's photo albums and at least his cousins have imagination!
Lumina by VictoriaTemple7
#19
Luminaby Victoria Temple
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...
Dreams of a Flower Boy by HallowsEveWrite
#20
Dreams of a Flower Boyby Hallows Eve
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...