Crossdressing Buddy Sex Stories Stories

245,069 results
Orientation
Length
Source
Infinite Scroll

CD Quickie

by AtlantaCDslut on Sep 12, 2017
Transsexuals & Crossdressers

**All my stories are true** My name is Rebecca. I am 22 years old and have been cross-dressing now for about 10 yrs. At first, dressing consisted of putting on a pair of panties or just a bra. Now it consists of shopping on line for different outfits, silicone breast forms, wig, etc. When I moved down to Georgia I got a roommmate who never gave me time to...

The Many Tales of Crossdressing.

by Whiteskorpion on Apr 22, 2025

This story is open to anyone who wants to write a crossdressing story, it doesn't matter if it's an original story or a fanfiction. Please respect Chyoa's rules, so ****, underage sex (younger than 18 years old) and **** **** are not allowed. I would like to keep this story as organized as possible. For example, if you're writing a fanfiction, before you rea...

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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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The Naked Bleached Blonde "Sissy Barbie Bimbo"

by Crissy on Apr 22, 2025

Did You Know? According to a study conducted on 293 female college students at the State University of New York in Albany, exposure to semen can lower symptoms of depression. And it’s mighty healthy: One teaspoon of semen contains over 200 proteins and several helpful vitamins and minerals including vitamin C, calcium, chlorine, citric acid, fructose, lacti...

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Crossdressing Stories

by Dayeandknight on Apr 29, 2025

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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Masculinity Lost

by Cdslavejessie on Apr 29, 2025

Introduction: Hi yall! This is my first attempt at a story so I would love and appreciate any feedback! I’m making this up on the fly so I’d love thoughts and ideas on how we can really humiliate young Danny Stewart! I prefer my stories be based in reality (crossdressing, padding for breasts and hips, hormones and surgery vs magic or scientific machines) and...

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In For a Penny...

by TheHellWasIThinking on Sep 15, 2017
Fetish

To the reader: After I'd finished this story, I didn't know where to put it. It contains elements of several Lit categories, and I probably could have put it in any one of them. In the end, I decided to put it in Fetish, although it's very much a Loving Wives tale, as you'll soon see. NOTE: Every word of this is true. (Except for "Every word of this is true...

The Transition Ch. 01

by Quantarx on Jun 8, 2020
Transgender & Crossdressers

Greetings and thank you so much for choosing to read my story. This is intended to be a multi part series so bare with me as I try to develop the characters and lay down the backstories. As always, Your feedback is always essential in the development of the story going forward. Please leave a comment down below * I Had been Married for about eight years w...

Sissy Chantel, New Reality Ch. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

A new story of a sissy's fantasy becoming her reality. But a reality, much more than she ever thought. This will be a multi chapter sissy maid and sissy slut story around Sissy Chantel finding reality of sissy maid and slut life can be more than she bargained for, enjoy. ***** Chapter One: The Journey Starts. Well another night and here I sit dressed in m...

The Agreement

by komrad1156 on Sep 18, 2017
Transsexuals & Crossdressers

Author's note: I prefer to write in the third person as it gives the writer so much more flexibility. However, I've written this story in the first person for one reason—it is my own personal story with love, marriage, crossdressing, and the ups and downs it invariably brings to a relationship. My name is David Calvin Peterson. My friends call me Cal. A smal...