Gay Crossdressing Stories

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Orientation
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Infinite Scroll

Crossdresser Evolution Ch. 03

by pantyhigh on Jun 12, 2019
Transgender & Crossdressers

Recap - Crossdresser Evolution - Ch 01 - How I got started crossdressing I was becoming addicted to masturbating while wearing panties, though there was still a feeling of shame surrounding it. I saw myself in these cum soaked pink panties. I could feel some sense of arousal but at the same time was ashamed that I was standing there wearing my wife's pantie...

Men and Women Cannot Be Friends

by chloevargas on Jul 15, 2020
Transgender & Crossdressers

"If this is what you want," she said, her tone even and controlled. I could tell she was disappointed. Perhaps she'd dreamed of a relationship or she'd fantasized of an emotional connection with me. She'd never hinted or remotely seemed interested. I thought she was happy with being friends. My few fumbling attempts to offer something more were rebuffed po...

A Transvestite Odyssey

by lynntg0444 on Mar 18, 2020
Transgender & Crossdressers

I like playing a girl, but it's complicated. I have always been more attracted to women than men, and had many relationships with women including two marriages. As a young man I had several sexual experiences where I played a feminine role. Wearing girly things was a real turn-on for me, and it seemed to make it less queer for us both. I would later learn th...

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...

Mistress Chantel, Tranny Dominatrix Ch. 12-13

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Twelve: Another Play Day Work Day at Our Studio. I arrive at my studio dressed for another day of fun and exciting dominatrix work. I park my "Plum Crazy Girl." step out in my red leather thigh high boots over my black sheer pantyhose. On my feminine looking body is a red leather form fitted mini dress with loose pleated, A-line skirt barely coverin...

Special Girls

by chloevargas on Jul 15, 2020
Transgender & Crossdressers

We get together every Thursday at lunch. Our friend Emilio loves having us, tells us we add some glamour to the place. His little restaurant is popular enough that we're lucky to have a standing reservation for luncheon late in the week. Should one of us be absent, we buy her meal and wine anyway else Emilio glare at the empty seat. Ricki is our waitress, a...

The Glass Door

by JackOLantern on Oct 16, 2018
Fantasy

((Author's note: I have made this story open to the public. I encourage people to post their own chapters and threads. If you are a potential writer want an idea of how the mirror works, read the first handful of chapters in my main thread to get an idea. You are under no obligation to make it function in the same way unless you want to, however. Have fun wi...

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Slave Tail

by Cyberweasel89 on Jul 11, 2020
Fantasy

In the kingdom of Pendragon, slavery is a burgeoning industry. Anyone can end up as one if they aren't strong or lucky enough. Slaves can be purchased, sold, and traded legally by anyone with the right business sense and magic. Slaves cannot be freed and are at the mercy of their current owner. Often kept naked to denote their sub-human status, some are cher...

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Barrack Room Betty Ch. 10

by MicheleNylons on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Ten -- Sea Daddies and Sea Mommies Seaman Michael Nyland graduated from Recruit School in March 1974 and was immediately posted to HMS Raleigh to commence training as a Writer; a sailor specialising in pay, personnel matters and administration. He was glad to see the back of HMS Chelmsford; Spike and the three other Leading Recruits had passed out...