Crossdresser Caught Stories Stories

187,637 results
Orientation
Length
Source
Infinite Scroll

Finally a Princess Pt. 02

by fireandlace0533 on Sep 14, 2020
Transgender & Crossdressers

Part two of a crossdresser who loves Disney who has come out to his wife while on a Disney Cruise. New experiences and adventures are ahead. Finally a Princess (Part Two) I woke the next morning around six thirty which was a little late for me. I laid in bed and thought about what had happened yesterday. I had actually spent time in front of my wife Sarah...

My Name is Raquel Ch. 05

by Raquels_Panties on Mar 2, 2020
Transgender & Crossdressers

You may have noticed an error in the originally published episode. It was a distraction that I have fixed in this version. Enjoy. ******* My name is Raquel and I'm a crossdresser. My nearly lifelong panty fetish, that I had kept from my wife of 15 years, was discovered by my stepdaughter, Jessica, while I was lying on top of my collection spread out all o...

Sarah's First Time Out Dressed as a Girl

by SarahCD on Sep 16, 2017
Transsexuals & Crossdressers

During my collage days, my girlfriend and I were at different universities but they were only an hour apart by direct train. Normally I went to visit her for weekends. I loved her place, Oxford. They did great lunches on Sunday's. Full roast dinner with wonderful roast potatoes and all you can eat. For a broke, starving student this was a wonderful treat....

Man in the Mask

by MiOtroYo on Sep 16, 2017
Transsexuals & Crossdressers

Mel was sitting on the corner of the cheap hotel king-size bed. Aroused, nervous, simply scared by the whole story, he still wanted it to happen. Once a lifetime dream, now a striking reality -- it was all here, from the remote sound of the cars passing by to that filthy, nasty smell of the motel building... "Hi, my name is Melinda. I am a young closet cros...

Adventure on CL

by Pantyhoseheels on Apr 14, 2020
Transgender & Crossdressers

This is a mostly true story of the first time I revealed my secret side to another person. My name is Colleen, secretly. I have crossdressed most of my life. It has always been my little secret. But as with most people, I have had the desire to try being with someone else, and to share my secret. I began to occasionally check Craigslist, looking for that...

Sex and 666 Lifestyles

by MoteDog on Nov 1, 2019
Fetish

Who is the main character? And what is the lifestyle they have or are thinking of registering to live the rest of their lives as? What is their motivation?What's next? Casandra Dell What's next? Casandra Dell...

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Online to Real Time

by sandraCD on Aug 30, 2017
Fetish

We first met on line in a chat room called crossdressers for males. I first met and was chatting with Bob, one half of Bob and Ann. We chatted about anything and everything under the sun. We talked about everything from life’s experiences to politics. That first day we chatted for at least five hours. But what we were really getting at the whole time was, wh...

Special Girls

by chloevargas on Jul 15, 2020
Transgender & Crossdressers

We get together every Thursday at lunch. Our friend Emilio loves having us, tells us we add some glamour to the place. His little restaurant is popular enough that we're lucky to have a standing reservation for luncheon late in the week. Should one of us be absent, we buy her meal and wine anyway else Emilio glare at the empty seat. Ricki is our waitress, a...

Cindy Lou Gets a Happy Surprise

by Boxlicker101 on Sep 16, 2017
Transsexuals & Crossdressers

One night, Cindy Lou left work and, instead of going home after getting off the subway, went to a nice restaurant that she and her roommate sometimes patronized. Amanda, the roommate, had called and asked her to stay away until after eleven o'clock because she would be entertaining a new boy friend in their apartment. On another occasion, they might decide t...

My Name is Raquel Ch. 03

by Raquels_Panties on Mar 2, 2020
Transgender & Crossdressers

My name is Raquel and I'm a crossdresser. I started out as a thirty-something guy with a fetish for masturbating with and in panties. I was caught and eventually transformed into a girl, Raquel, by my 18-year old stepdaughter, Jessica. Jessica unlocked my inner desires and expanded my horizons. I was now into fully dressing in all varieties of lingerie. And...