Crossdressing Brother Stories

45,080 results
Orientation
Length
Source
Infinite Scroll

Cindy's Panties

by secretanon on Sep 13, 2017
Fetish

I am around 24 years old and I have always enjoyed wearing panties. I think the feminine feeling of it all really turns me on. At a young age, I discovered masturbation from cumming on my mothers panties after deciding to be bold and try one out from curiosity. I was never able to fufil my love for panties, being in a house full of males, so I never had a si...

Prom Night with a twist

by MissAshleyJ on Apr 1, 2019
Humor & Satire

BUZZ BUZZ BUZZ… “Ugh…” Sam groaned as he pulled himself out of bed. “SAM! Breakfast!” He heard his father calling up as he rubbed the sand from his eyes “Coming” he yelled down as he slumped his way out of his room. He entered the kitchen and plopped himself on a chair. His father dropped a stack of pancakes on the table as his mother looked up from the news...

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Forced Crossdressing Stories

by Dayeandknight on Feb 1, 2018
Transsexual

All of these stories share a central theme of Crossdressing. Rather than add yet another story for one of my ideas, new ones will now go here. I'm making the call, out loud, for additional authors to add their own threads and work with me. I would love anyone interested in any of these stories or my previous ones to add their own threads. If writing isn't yo...

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From a Husband to a Dutiful Sissy Ch. 02

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Two: My reveal, a true reveal for the sissy in me. I reach to the bottom of the stairs and at the front doorway entrance, Helen and Jenny are standing and looking at me in my black maids dress, white tights, black velvet 5 inch spike heel pumps, wig and makeup. The look on their faces seeing me dressed as such is priceless. This is the first time He...

From a Husband to a Dutiful Sissy Ch. 01

by Sissy_Chantel on Sep 25, 2017
Transsexuals & Crossdressers

Preface: Welcome to my next sissy story. This one is based around the exciting ideal of a married sissy, crossdresser. It will have many ideas based on my thoughts about how life could be for me as a married, crossdressing sissy maid. I hope you all enjoy it. ***** Chapter One: Sometimes one's most unique secrets do come out. My name is Phil and I've alwa...

Jolene's Momma Pt. 01

by ValoryG on Jul 27, 2020
Transgender & Crossdressers

(The names and locations in this story are completely fictional and have no connection with any person living or dead.) My name's Chris. Wife Jolene and I have been married six years now. Live in the small city of Centertown, Ohio. It probably got that name because it's about half way between Columbus and Cincinnati. Being from a midwestern small town, the...

The Fairer Sex

by PrinceCai on Aug 13, 2020
Fetish

What might the world look like if women were usually stronger and more aggressive than men? Perhaps a society existing very much like the one we know, but with almost every gender role reversed. Not only that, but what if the ideas about the sexes that evolved in such a world were far stricter, enforced through every aspect of society and any deviation looke...

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Pokeslut

by AzorAhai on Apr 6, 2019
Fantasy

Introduction to Pokeslut: Pokeslut is an alternate universe to the Pokemon games we all know and love but with a twist, the women in this Pokemon universe are not seen as equals to their male counter parts and often if a female trainer loses in battle they must pay the trainer in either sex or cash. It varies from person to person, some guys will just let yo...

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Serving the Dark Lady Ch. 07

by Certeis on May 27, 2019
Sci-Fi & Fantasy

"Twenty gold for the engagement ring." Karee looked up with a start at the Tiefling who ran the jewelry stand. "You were staring at it, cutie pie. Hoping to get one from a special someone?" She smirked at him coyly. Karee laughed nervously, and then blushed when that didn't work. "No... just daydreaming." "About your future..." She paused, letting the word...

Kissing Crossdressers Pt. 02

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

I awoke the next morning still dressed in Carla's purple panties, stockings and matching bra. The rampant rabbit and the dildo were beside me on the bed. There were traces of the lip-gloss on the duvet and the heady, pungent smell of cum. Carla's panties were stained with the stuff. I figured I had a lot of cleaning and clearing up to do. I felt a sense of...