Crossdress Brother Stories

44,291 results
Orientation
Length
Source
Infinite Scroll
SmutMD: The World's Biggest Erotic Literature Search Engine.
© 2025 SmutMD.com

A Sissy Story

by PinkRebecca on Feb 21, 2020
Fetish

You always were a normal boy growing up, weren't you? Played some sports, although not to an extent where you stood out anywhere or made any teams. You had a normal friend group, as far as you knew atleast. You liked girls, like most of the boys around you, although you lacked the curage to talk to them. Well not to talk to girls in general but in a romantic...

Open in Reader

Taste of Temptations

by satoshy12 on Sep 29, 2020
Fan Fiction

The Sinful Tastes This is the tale of Prince Arlan Baratheon. Arlan Baratheon is the Son of Cersei Lannister and Robert Baratheon, with the classical Baratheon bright blue eyes and the Lannister Golden Hair. He was a normal person who had landed in Westeros and with defective magic he had just enough control about his magic to increase his reflexes, strengt...

Open in Reader

Wet Dreams

by TheNextGamer on Jul 15, 2018
Fetish

For two entire weeks, you, John Doe, have researched tirelessly on a place that historians and philosophers have secretly called... The Labyrinth. A special location that links the psyche of every living being on Earth. The place where you can traverse in people's dreams and do whatever you've wished. Out of sheer luck, you've managed to find a way to enter...

Open in Reader

Confiding in My Hairdresser

by Leighharding on Dec 19, 2018
Transgender & Crossdressers

I've always had a great relationship with my hairdresser, Mary. She'd been cutting my hair for years and we probably shared a few more details than we should about sex, she made me laugh at some of the naughty stuff she'd been up to! On occasion around a year ago, she came to the new house that I'd just moved into with my girlfriend to cut my hair. The cha...

All Inclusive Resort

by Dayeandknight on Sep 26, 2015
Transsexual

Tracy fell back onto the bed, finally able to rest after his ordeal. He worked in an office and he dearly needed a break from the monotony of it all. Cancun, Mexico would be his escape from his life. He worked with a travel agent and got a travel package to his liking and saved what he could for the trip. The airport was a nightmare he thought would never en...

Open in Reader

Witches of Westfield Mall

by Vestiphile on Apr 22, 2019
Fantasy

I was in the Westfield Mall to return a couple shirts that didn't fit me. I knew I should've tried them on, but dress shirts are a massive pain in the ass when you're in a fitting room. All those pins and clips, the cardboard holding the collars and cuffs in place...way too much work. So imagine my surprise when I saw people running or briskly walking out of...

Open in Reader

Forbidden Codex

by TheCanadian on Aug 30, 2018
BDSM

You’ve got a freind named Denise, with a strong interest in the supernatural--something you have in common. At times, it seems she has a crush on you, but you’ve been friends for years. Besides, Denise was just older than you by enough that you figured she didn’t think of you that way. One afternoon, you knocked on Denise’s front door. When the door opened,...

Open in Reader

Disgruntled Curves

by TheCanadian on Aug 26, 2018
Miscellaneous

I'm not a big enough creep to stare and drool or follow a nice booty around...but if it happens to be in front of me, of course I'm going to look. But on this fateful day, I happened to be on an elliptical behind the wrong booty (or, I suppose, the right one, depending on your penchant for being objectified by objects). I watch her in her black leggings, ste...

Open in Reader

Sissy Truth or Dare

by BimboBarbie on Dec 23, 2017
Transsexual

You wait nervously outside the front door of Samantha's house, your heart pumping as you still can't quite believe your luck. Just a small, nerdy guy like you being invited over to the most popular girl at school's house! Finally gathering up the courage as you tentatively press the doorbell, hearing the sing song chime through the door. A whole minute passi...

Open in Reader

Dreambox

by Hanna on Aug 11, 2020
Transsexual

“Boring dreams? Fragmented dreams? No more, try Dreambox, where your inner dreams come alive”. The radio had boomed this for a long time, and my curiosity was intrigued. What is Dreambox? I walked down to the mall and after some shopping did I find that my favourite restaurant was closing, with a sign “Dreambox is coming”. Two months later Dreambox had opene...

Open in Reader