Caught Crossdressing Stories

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How Gerry Caught Me Crossdressing!

by CarrieQ on Sep 16, 2017
Transsexuals & Crossdressers

When we're young, we can be extremely naïve! This applies to almost everyone, and it's my only excuse as to how Gerry caught me crossdressing so easily. I had paid for a room in the hostel where he worked as a caretaker, and expected privacy. It simply never occurred to me that he, or anyone else for that matter, would feel at liberty to intrude upon me on t...

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...

Just a Girl

by katie_risita on Sep 18, 2017
Loving Wives

My name is Frank. OK, it WAS Frank, until recently, when things...changed. Now, more often than not, I answer to Katie. I know, I know. Yes, I am a guy, technically, but, well...to explain, it's gonna take a story, a loooong story...but not a boring one, I promise! I am a 33-year-old guy from Long Island. I have always been overweight, not great-looking, s...

TV Beginnings - Caught by Neighbour

by Nylontease on Sep 16, 2017
Transsexuals & Crossdressers

I started crossdressing at quite an early age, 'borrowing' items of my mum's underwear and furtively dressing in them when she was at work. As I was an only child, and mum and dad had separated, I had quite a lot of time to indulge my little hobby! I used to love wearing her tights, the sexy feel of them encasing my legs and cock, and the way they made me fe...

Caught in Her Panties Ch. 02

by Knightofround on Sep 16, 2017
Transsexuals & Crossdressers

This is a fictional story as was part one. The content of this story may not appeal to everyone. It includes female domination, crossdressing, strapon, lesbian, gay, and such. Just keep in mind that it is fictional and should not be taken seriously. Otherwise just enjoy the read. ***** It has been almost a month since my wife Mary discovered my secret. She...

Caught For the Last Time Ch. 05

by TGJamie on Sep 12, 2017
Transsexuals & Crossdressers

In the morning I woke up in a much better state of mind. Less confusion and perhaps a better outlook on what had happened the prior night with Sally. Still, I was not all that comfortable with someone else knowing about my crossdressing, but at the same time, having someone for my wife to talk to was better than the way it was before, way better. We had a...

Initial Crossdressing Adventures

by vjak19 on Sep 19, 2017
Transsexuals & Crossdressers

Since the first article I wrote described the last time that I dressed as a woman was generally well received, I have decided to share some more of my story. To do that I will start the journey at the beginning and travel through to some of the first times that I ventured out into public dressed as a woman. For those that did not read my initial offering le...

Caught Ch. 01

by Love2BeALady on Sep 11, 2017
Transsexuals & Crossdressers

This is my first story and I apologize about any errors. My girlfriend and I had been living together for over a year. She moved into my house that I had custom built about three years ago. I had always been into crossdressing since I was a kid. So when I had my house built, I had a secret room created for my crazy kinky side. None of my girlfriends had ev...

Caught Relaxing Pt. 01

by StephaniePlayland on Aug 6, 2019
Transgender & Crossdressers

This is going to be a short series of stories. This one really starts the journey out, they won't all be in exact order or have a proper linear flow to them. Just depends on what's has caught my interest that day, and needs to flow out of me. It's Friday night, no plans or anything to do a perfect night to dress up. Hangout have a drink and relax being Ste...

Caught Out at Work

by alexis19901 on May 12, 2020
Fetish

For those of you who have read the stories that I've already put on, you will already know a bit of my back story, but for those of you who are reading a story of mine for the first time, I will give a bit of background in the intro. WARNING - This story contains m/f, pegging and some crossdressing. So, for those of you who aren't aware, I've taken to wr...