Crossdressing Brother Stories

45,080 results
Orientation
Length
Source
Infinite Scroll

Dress up change

by Fionna on Aug 17, 2020
Fetish

You've always loved to cross dress and try on other peoples clothes. The thrill of wearing other peoples clothing makes your heart flutter and your skin feel tingly. On your 18th birthday, while your friends and family are gathered around singing to you, you blow out your candles and wish. You wish to be able to swap your body parts with whomever owns the cl...

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My Neighbour's Party Pt. 01

by Manndee on May 8, 2018
Transsexuals & Crossdressers

Part 1 Sometimes in your life you meet someone and just know they are amazing. Annie is the most energetic, enthusiastic person I have ever known - she has none stop energy. When Annie came into my life, I had no idea just how much my life would change. According to Annie, everyone knew Greg was different. He was a really nice guy, from a nice family, very...

Kasey's Legs Ch. 02

by KaseyLegs on Sep 19, 2017
Transsexuals & Crossdressers

My girlfriend Darcy and I were having breakfast and talking about my first experience going down on a man. I had been dressed up in my sexiest girl clothes with my makeup and hair giving me an almost passable look. Darcy had brought me out to a club that hosted a "drag night" and I had been a hit. I kept explaining to men I was straight and I crossdressed f...

Fetishville (Adding Encouraged)

by VioletWinters on Sep 26, 2017
Fetish

Welcome to Fetishville! I am Violet, the mayor here. I know you're eager to start so let's get to it. To begin with your adventure, press the "Start Game" button on the right and find your fetish. It is pretty straight forward. If your fetish involves dominating, select [Dominant]. If it involves being dominated or being submissive, select [Submiss...

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A Crack in Reality

by Mr Nice Guy on Aug 20, 2018
Miscellaneous

Something is wrong. There is a crack in reality! Things are changing! Is it human made? Has it always been there? Is someone controlling it? Is there any way to stop it?!What's next? Average Office Worker Alex William Borgman, Mad Scientist Rachel Davis, College Lesbian Goth Girl Daniel, average thief Jason Willows, struggling middle class family member. M...

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Tales of Feminization

by AnonWriter on Jun 11, 2014
Fetish

In a seemingly normal town, a new social movement is taking place. White boys are encouraged to act, dress, and be feminine. You are a student at this school, and this is story of how you become a dirty sissy slut. Choose a boy to play as and be feminized. (All characters in this story are of legal age) (I'm only working on Mark's story right now, but feel f...

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Internship

by nimt on Jul 12, 2018
Transsexual

An internship was compulsory as you approach the final year of your high school. The school believes in providing students with the opportunity to gain valuable practical experience by learning from the industry of tomorrow directly. You went for several interviews and only successful candidates get notified. In the events that the none of the companies pick...

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Second life of Emily

by Alexia Wright on Jun 3, 2015
Fetish

I have always wanted to get fucked by another man. Being 5'6" and weighing little over 60 kilos, my effeminite and near hairless body bore no signs of an able bodied alpha male, so i decided to explore my inner girl since my mother and sister are the only people i live with. It started with simple things, like my sister's school clothes, then her under...

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Dutiful Assistant

by Jagvillhem on Sep 28, 2019
Transsexual

((There might be some changes throughout the chapters. This is because I am finding out the way I like to write. I'm learning different styles and quirks. Because of this, chapters might differ in style from time to time. This is definitely a trail and error kind of thing, chapters might have changed once you re-read them, this is because I might have gone b...

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Life's What You Make It

by HYjaCK on Jun 7, 2020
Amateur

The first thing I see as I wake up is the blinding light coming through my curtains. Sadly, I couldn't afford blackout curtains due to my poorly-paying job that barely covered the bills, but I've slowly gotten used to it. I sit up and get off the sofa, stretching my back and neck. I also couldn't afford a large flat, so I had to make do with a single-room wi...

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