Crossdresser Lover Stories

78,804 results
Orientation
Length
Source
Infinite Scroll

Trixie's Adventure

by spandexman on Aug 18, 2017
Fetish

Trixie, the 19-year-old, 5'5", adorable, assistant-manager, with big baby-blue eyes, high cheekbones, a cute dimpled chin just like her gorgeous aunt, thick long curly platinum-blonde hair, and an incredible 36GG-28-33 hourglass figure that her too small red knit turtleneck sweater, skintight white riding breeches, and shiny brown riding boots hugged like a...

Crossdresser's Private Gloryhole

by kccrossdresserleslie on Sep 16, 2017
Transsexuals & Crossdressers

This is a true story, I am a crossdresser and this is the story of a wild wild night! HI. My name is Leslie, I am a very dedicated crossdresser. I have to live as a male by day because of work. At night I usually get home pop open a beer and pop a buttplug in my juicy hole, get on the computer and watching some dirty naughty things until I just have to dres...

Mary Becomes a Whore

by Juggerhead on Jul 30, 2019
Transgender & Crossdressers

Mark was like any other ordinary 25 year old guy with a regular 9-5 job as an office executive in an finance company. He was fair, around 5 feet five inch tall and had a slender frame. Often his friends and colleagues would ridicule him for his height and thing body. He had a boring life and didn't indulge in partying or clubbing. After his divorce he went o...

Crossdresser Evolution Ch. 05

by pantyhigh on Aug 7, 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...

Life and Time of Lady Vargos Ch. 01

by rik581 on Oct 3, 2018
Transsexuals & Crossdressers

I am in the process of reposting my stories. *** "The Life and Times of Lady Vargos" is the second book of the Martin Hastings adventures into a life of forced feminization. This story follows the feminization and marriage of a reluctant young man as he is forced to accept his fate as a male/bride, in a same sex marriage, arranged by his family. This stor...

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...

Sarah was a Bad Girl

by SarahCD on Jan 8, 2019
Transgender & Crossdressers

I first published this experience a few years ago. I prefer to call them 'experiences' since the term 'story' implies fiction to me. My experiences are based upon my real life. Since I started posting my experiences my writing skills have improved a little. While, I cannot change what actually happened to me, I have added some more details and corrected some...

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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Going Gurly Ch. 01: Cara's Clitty

by anna_subCD on Sep 16, 2017
Transsexuals & Crossdressers

My stories are all true recollections of events from my life, as accurately as I can remember them, with two exceptions: 1. The names of my partners have been changed for their privacy; and 2. I have omitted any references to safe sex, because reading about people fiddling about with condoms is not to my mind very sexy, and in stories you don't need to be...

Ugly Duckling to Sissy Princess

by JHouston on Sep 18, 2017
Transsexuals & Crossdressers

All names have been changed to protect the guilty. ***** Being a very short guy (5'3") with a small frame has been a major handicap in my quest for female companionship. Having a micro penis was the nail in my coffin. Throughout my youth, I was ignored or rejected by girls. I had my first girlfriend in college, Caroline Fletcher. She was smart, beautiful,...