Crossdresser Caught Stories

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My First Crossdresser Pt. 01

by Princess_Rebecca1991 on Nov 26, 2017
Transsexuals & Crossdressers

Tempting, isn't it? Being in a room or just being aware of there are drawers filled with lovely, feminine underwear. The kind of feminine garments you have dreamed of wearing for sometime, your fantasy you've longed to make a reality. How could a pair be noticed missing? There are so many and they wouldn't suspect you, not the straight going masculine male t...

Sarah was Naughty in the Hot Tub

by SarahCD on Sep 14, 2017
Transsexuals & Crossdressers

Late last night I went down to the hot tub in our complex. I wore girl's bikini panties under my cutoff shorts. I always pick out my brightest sissy girl's panties. They were bright red with yellow roses on them. Over them I put on a pair of worn-out white shorts. If I were seen walking down there no one would suspect what I had on underneath. However, the c...

Neighbor to Lover Pt. 01

by sarahchica96 on Oct 2, 2018
Transsexuals & Crossdressers

Introduction It was the summer I (Alex) and my twin sister Gina graduated from Business school, ironically Gina and I joined our family real estate business. This was a way of our parents keeping us busy and stop our procrastination about searching for jobs elsewhere. It was also the time my crossdressing persona met our neighbour Mr Parker. Backstory......

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...

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...

Female Erotic Police Squad Pt. 03

by mattpantyhose on Sep 14, 2017
Fetish

Most of the officers of Female Erotic Police Squad enlist in the service to catch criminals. But there are also some who do it for sex. Physical love is the modern way to fight crime, but it does not necessarily mean that sex should be considered merely a tool. As long as an officer fulfilled her duties properly there was no reason for her not to take additi...

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...

I Accidentally Sucked Dick! Pt. 01

by CDJulie on Aug 18, 2017
First Time

I've never given anyone head before although I thought about it for years. I'm a lifelong crossdresser but closeted. I was never brave enough to approach anyone and I shied away from any offers that were made. Mostly, because when I fantasized about sucking dick it was always as crossdresser, more specifically, in the role of a girl. So when I was 33 I vis...

Dreams

by DrLuverotica on Sep 25, 2017
Transsexuals & Crossdressers

"Hey! Hey! Wake up, wake up!" "What? Jo, what is it? What's going on?" "I think you should be telling me that!" "I don't understand." I was slowly coming round now, But I was still mystified as to why my wife had woken me at 2 a.m on a Saturday morning. "Erm your cock is as hard as nails and you were waving your ass in the air," Jo said, starting to laug...

From a Husband to a Dutiful Sissy Ch. 07

by Sissy_Chantel on Sep 18, 2017
Transsexuals & Crossdressers

Chapter Seven will also advance the time of my story here a bit. To move my story along into a lifestyle changing story I will have this chapter set seven months after Phil was outed as crossdressing sissy named Chantel. Over the last seven months, life for Chantel has become entrenched as a sissy maid and slut. The sex video productions put up online have...