Crossdresser Sex Stories On Tape Stories

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Crossdresser Evolution Ch. 04

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. I could feel the arousal but at the same time was ashamed that I was wearing my wife's panties knowing that I would soon be cumming in them. There was this part of me that was telling me, "I CAN'T like this," but there was...

It Started As A First Date

by spandexman on Aug 30, 2017
Fetish

As far as first dates were concerned, Roxy Fox, the 23-year-old, 5'11", Barbie doll faced gorgeous, secretary, with a strong dimpled chin, high cheekbones, big almond shaped hazel eyes, thick wavy shoulder length fiery-red hair, and a very firm, but extremely curvaceous 38FF-26-38 hourglass figure that her skintight white spandex pants, tight red spandex top...

From Dom To Sub

by ScarlettCD on Sep 14, 2017
Transsexuals & Crossdressers

Twenty minutes to go. A few days ago I had posted an ad online looking for someone to come to my place so that I could, to quote my ad, "get treated like a tranny slut by a true Dom of a man." I kept the ad low-key and photo-less to ensure none of my colleagues from work saw it of course, but more importantly, I was a Domme in my own spare time and did not w...

Eric's Dreams Pt. 03

by Genevieve_Ohara on Jul 14, 2020
Transgender & Crossdressers

Eric kept thinking about his sex problem. He was a crossdresser. But most gay men didn't like that. The sex, yes, but not the crossdressing. Gay men, at least most gay men, had no interest in lipstick and lingerie, and the thrill of passing as a woman. They wanted to fuck and be fucked by men. They wanted to have their cocks sucked by men. And they wanted to...

Crossdresser In Picnic Area

by Lovinhose on Sep 13, 2017
Transsexuals & Crossdressers

This is my first attempt at a fictional/fantasy story. All my stories thus far have been true, honest, and accurate, as much so as I can recall. But I kind of ran out of true stories that were worth sharing (for now, but I've got some 'irons in the fire' and hopefully I'll have another true story to share fairly soon). The story I will tell here is something...

Sissy and Wimp

by 1Gratiano on Jul 14, 2020
Transgender & Crossdressers

1 Now the common belief is that any man who wants to wear women's clothes is gay, and that the heterosexual crossdressers who claim to be straight but "just like the feel" of silk panties and so forth, are being, well, less than candid. Be that as it may, heterosexual and homosexual crossdressers are in fact distinct psychological types. To be sure, ther...

Vendetta's Diary

by thrillerauthor on Sep 14, 2017
BDSM

Detective Frank Sturgess scratched his thick gray hair as he studied the report in his hand. He shook his head several times as he read it through. When he was finished, he added it to the mountain of papers strewn across his desktop and fished around until he found a small black cassette. Sturgess thought he had seen everything in his eighteen years with t...

Parking Area 2 Miles

by Lovinhose on Sep 15, 2017
Transsexuals & Crossdressers

Prior to writing this next installment in my awesome sex life as a bisexual crossdresser, I thought I had already written about all of my worth while, true life experiences, but I had actually forgotten about this one. It happened in, I believe, 2008, during the end of the summer. I was driving my truck. I am a truck driver by trade. Three hours and a co...

Michele Nylons' True Stories

by MicheleNylons on Jul 14, 2020
Transgender & Crossdressers

Introduction For those of you who only read fiction I suggest that you go directly to my autobiographical sex stories contained later on in this essay; but what I thought I would like to do is to take a break form my usual 'physically forced' and 'caught with consequences' Transvestite sex stories and write some of my musings about Transvestism and share wi...

The Writer's Secret Ch. 01-02

by AnnMichelle on Sep 13, 2017
Transsexuals & Crossdressers

Hi everybody! This is one of the many stories I've written over the years. I've decided to clean them up (read: edit the heck out of them) and start sharing them. This one has some light-femdom, a pretty willing husband, and a few fun surprises. Enjoy! * Loren had no idea what he was getting into when his agent suggested he write transvestite fiction. Nor...