Crossdresser Caught Stories Stories

187,637 results
Orientation
Length
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Infinite Scroll

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...

Mistress Chantel, Tranny Dominatrix Ch. 02

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Two: A Day in the Life of Tranny Dominatrix Chantel Waking up into another morning where this transvestite dominatrix gets to dress up and enjoy her life of toying with sub men and sissies/crossdressers. Working hard to get my femme look down over the last couple of years prior to operating this Dominatrix business, I enter my very lady-like powder...

Sarah Shared the Hot Tub and Sauna

by SarahCD on Feb 26, 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 detail and corrected some...

Kissing Crossdressers Pt. 01

by Candyboi on Sep 13, 2017
Transsexuals & Crossdressers

It started when Carla, my hot sexy wife went away on a spa break a few days with some of her girlfriends. Carla is 40 (I'm 48), has blonde hair, blue eyes, 34DD tits and a curvaceous ass. She works long hours in a busy office as a manager, I work in a local library and my job is far less stressful than hers. And her job has definitely taken its toll on our s...

Crossdresser Jerks Off in Library

by iwant2suckabig1 on Oct 12, 2020
Transgender & Crossdressers

So have been really busy with life and career so haven't posted any of my adventures in quite awhile. I've been continuing to have them as often as possible just haven't made the time to share. For those of you who haven't seen my previous postings, I am a slightly built 5'7" male who is passable when fully made up and dressed. Although I am slight of build...

My First Time Dressing Ch. 01

by ChrissyCD on Sep 16, 2017
Transsexuals & Crossdressers

This is the first of hopefully many stories to come. This one may be a bit boring and lacking the hardcore fucking and sucking so many of you are used to. I feel the need to tell it because it will give some background to the rest of my stories. For the most part I will send them in chronologically from my younger days to present day as a undercover crossdre...

CD Asst. Secy. Ch. 05: 1 yr. Later

by cdtycoon on Jun 2, 2020
Transgender & Crossdressers

On 9th December 2020; as now my daily routine, I woke up and went to the hospital, took the CEO's car, and brought Mam and secy. from their homes, then went to park the car and went to the CEO's office. Well, it was like any other day and was pretty normal even though it was raining outside as it was a winter monsoon season. But still, I notice that somethi...

Crossdresser Visits ABS

by iwant2suckabig1 on Oct 12, 2020
Transgender & Crossdressers

Thought I would post another one of my true adventures. Those of you who may have read my other adventures know that I enjoy dressing super slutty and being shocking in public. Nothing gets me more worked up than people watching me enjoy myself. With that in mind many of my adventures are dressing up and flashing my hard cock to people. While I enjoy both...

My First Crossdresser

by Jay876 on Jul 31, 2019
Transgender & Crossdressers

Monday A year ago. I was sitting in my flat, as a university student just browsing the men on grindr. I was inexperienced at the time and I had only been with one man, and that was just for oral. So, I was intrigued when I saw someone on my page, just nine meters away. A crossdresser, stocky, but wearing a maid costume, with his ass bent towards the camera....

A Sissy in the 22nd Century

by JerkGently on Jul 1, 2020
Transsexual

In a future not too far flung, humanity has progressed to a stage where almost all production and provision of society’s needs is automated. With no need to work, all citizens are instead driven to find lifestyles that fulfil their own and each other’s fundamental desires. This is achieved by the medium of an overruling system of artificial intelligences and...

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