Sissy Brother Stories

1,000 results
Orientation
Length
Category
Source
Infinite Scroll

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,...

Kyle, The Party Dog

by Mixedwritings1993 on Sep 17, 2017
BDSM

After calling his little brother by his name, Brandon got a little pissed off when no one responded, "Damn, that boy is sleeping once again, man, can't he even stay awake for few hours at a stress?" He stomped on the floor hard on entering his little brother's room and was amazed to see even the loud stomping noise didn't wake up his brother, Kyle. Brandon...

The Bimbug

by Testytesterton on Jun 17, 2020
Science Fiction

The world changed overnight with the first cases of the Sexually Infected Subjects Spreading Infections Exponentially Syndrome, or SISSIES, became known. At first it sounded like some urban legend, men turning into hot, horny, hung shemales and spreading the infection to any man that came in them...or any man they came in. It was only after you saw video evi...

Ladybug corruption

by fnuriia90 on Apr 22, 2025

The world changed overnight with the first cases of the Sexually Infected Subjects Spreading Infections Exponentially Syndrome, or SISSIES, became known. At first it sounded like some urban legend, men turning into hot, horny, hung shemales and spreading the infection to any man that came in them...or any man they came in. It was only after you saw video evi...

Merry ChristmASS, Bitch Boy!

by humbleslave on Sep 16, 2017
Celebrities & Fan Fiction

The holidays were upon us. I had spent the last three months of my life as the personal sex slave of Brittany Andrews and Chantz Fortune. By now I was used to the chores, and the beatings, and constantly servicing and being fucked by their various strapon dildos. However, I never got used to the humiliating situations that they placed me in on a daily basis....

The Choices of Evelyn Ch. 13-15

by angiquesophie on Oct 30, 2018
BDSM

Chapter Thirteen – Sandro. Did she remember? Did she remember what remembering was? Time was irrelevant; there was no past, no future. Just this one moment – stretching tighter, winding up to a point of breaking, but never breaking. Her skin rippled as her spine arched. Hunger consumed her, but it wasn't for food. The gasping throats of her flesh needed...

Hot sister's sick fetishes

by 91timhard on Apr 22, 2025

Since your little sister hit puberty, she got incredibly hot. Her boobs grew to a perfect size and shape, her has is round and spankable. Her skin is incredibly smooth and her legs are long for her short stature. You feel ashamed every time you fantasize about her. But you just cant help it. One day your horniness gets the better of you, and while she is in...

Jonny Wall

by TheBigEd on Sep 17, 2017
Loving Wives

I work in a small office where we manage commercial real-estate. I have a total of over twenty-two million square feet of warehouse space and over a million square feet of office space. I stay away from retail; the turnover is too great and they require a lot of time and maintenance. I just love Fridays, it's the slowest day of the week. I generally take th...

My brother made me a sissy

by cutiepie183 on Apr 22, 2025

I had just turned 21 a few weeks ago when it all began, my brother, not long turned 20. We both had jobs and had moved out of home and into a fairly nice 2 bedroom apartment thanks to a little bit of help from our parents, but it was mostly us. We had been living together for a couple of months and had settled into a routine finally finding our feet with liv...

Blackbone Crossing

by DonSwami on Dec 4, 2020
Fantasy

AUTHORS NOTE: This story is still a work in progress, I’ve got a lot of idea’s on where I want to take it and what different chapters are going to be. I decided to publish Blackbone Crossing because I really wanted some feedback/ideas. The story is open to other writers, so feel free to submit your addition! Some chapters I’m still working on and I haven’t p...