Caught Crossdressing Stories

164,111 results
Orientation
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Infinite Scroll

Girlboy Diary Day 01

by Hartford on Sep 16, 2017
Transsexuals & Crossdressers

Day 1 It might never have happened if my aunt hadn't caught me wearing girl clothes at the mall, clothes plus a wig and make up. How she knew it was me is a mystery because I can pass like nobody's business. Hate to brag but it's a fact. Anyway, my aunt followed me, got some still photos and video on her blackberry, and showed it to Mother. I found out six...

Rm 209: First Sex as a Crossdresser

by MelissaMwaz on Sep 16, 2017
Transsexuals & Crossdressers

This is a TRUE STORY. I've been crossdressing for much of my life, as far back as I can remember. I would even go to sleep as a kid and pray that I would wake up in a girl's body. In the last few years, now that I live by myself, I spent about $1,000 on a whole wardrobe of women's clothes for myself - bras, thongs, dresses, tops, stockings, lingerie, make-...

Sissy Chantel, New Reality Ch. 01

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

A new story of a sissy's fantasy becoming her reality. But a reality, much more than she ever thought. This will be a multi chapter sissy maid and sissy slut story around Sissy Chantel finding reality of sissy maid and slut life can be more than she bargained for, enjoy. ***** Chapter One: The Journey Starts. Well another night and here I sit dressed in m...

Adventures after Dark Ch. 01

by classmate1119 on Sep 16, 2017
Transsexuals & Crossdressers

-Author's note- I started crossdressing in my teens, but coming from conservative South-east Asia, it was definitely my darkest secret for many years. I would often dress in my mother's dresses, and put on her makeup when I was home alone, but I stopped crossdressing when I moved away to start college. When I won a scholarship to study in the UK, I did no...

Erika's Story Ch. 03

by Quantarx on Jan 22, 2020
Transgender & Crossdressers

This is the third part in Erika and Mary's widening exploration of crossdressing, if you have not read the first couple chapters I encourage you to go back and read those first. also, thanks for the feedback I have received and please continue to rate and leave feedback and comments so I can continue to evolve as a writer. *** I lay in bed with my loving...

Ultimate Sissy Fail

by cdbrittany4bbc on Feb 12, 2019
Transgender & Crossdressers

This is the story of the perfect sissy getaway. This story contains subjects of crossdressing and interracial male sex acts if this offends you please don't read. Everything except one or two events happened, Now, there is some embellishment. I had to tell someone. I decided to tell everyone. A little bit about myself. I am in my late 50s. My adventures in...

A Night of Surprises

by StephaniePlayland on Oct 16, 2018
Transgender & Crossdressers

Back story. I've been crossdressing for many years. The reasons for it are not really important however, I know I enjoy escaping being me, and getting to be softer, submissive and docile. My friend, Sir caught me crossdressing a long time ago, he has never really cared what I do as he has lots of women. We both enjoy the friendship and no judgements about a...

Crossdresser Evolution Ch. 02

by pantyhigh on Apr 8, 2019
Transgender & Crossdressers

Recap - Crossdresser Evolution - Ch 01 - How I got started crossdressing I was becoming addicted to this new way of masturbating very quickly, though there was still this feeling of shame surrounding it. I made sure I deleted the browsing history and then went to the bathroom to clean up. There I saw myself in these cum soaked pink panties. I could feel som...

Tammy Truth and Fiction

by TammyPanty on May 9, 2018
Transsexuals & Crossdressers

One of the elements of erotic stories is they are based in most cases in fiction. But most fiction is grounded in fact. I get several pieces of feedback about my stories asking me about certain experiences I have described. Not everything in each story has actually happened, but I have personally experienced more of what I describe than what is fiction. Fir...

Kasey's Legs

by KaseyLegs on Sep 19, 2017
Transsexuals & Crossdressers

I had been crossdressing for close to ten years. It started as a Halloween costume gag where I shaved my legs, put on a cheerleader outfit and wore a scary mask. After I kept getting compliments on how good my legs looked I continued shaving them and experimenting with dressing in a variety of women's outfits, skirts, high heeled shoes, panties and bras. It...