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Crossdressers Talk About the First Time They were caught Crossdressing

“I was 15 years old and I was the middle child between two sisters. My older sister had just moved out and had left behind few of her things. I was shifted into my new room which belonged to her. My parents told me to move my stuffs into the new room. That day, my little sister had a dance recital so my parents went out and left me behind to clean up my new room.

I was quite excited to have my own room  As I was cleaning the closet, I found my old sister’s clothes and few of her bra and panties collection. There was also some makeup in the top drawer. Her old prom dress caught my eye and I don’t know why but I really got curious to try it on.

I had been curious of how it would feel to wear a dress before. This was a good opportunity to experience that. So, I undressed myself and then slipped it on and zipped it up. It was quite exciting and different. It was something I had never felt before. I walked around the room in the dress and really liked how it felt on my body even though the dress was a little big for my body.

All of a sudden I heard the front door of the house open and footsteps quickly running through the house. My younger sister had forgotten her ballet shoes and she was there to get them. She kept calling my name to know what I was doing. I was too scared to answer back and that made her yell my name out even more.

I panicked and tried to unzip the dress. Somehow the zip got stuck and I couldn’t take off the dress. Then suddenly, the door opened and my mother saw me. Instant Panic and I was so embarrassed. She was shocked too and screamed at me why I was dressed in my sister’s prom dress.

My mom cried out  “I can’t handle this right now, take that dress off and we will have a talk when I come back from the recital. We are already too late”.  My heart was beating out of my chest and I was super scared. I knew I was in a lot of trouble. My mom rushed out of the house after getting my sister’s shoes and I sat there alone for few moments wondering what just happened. Then after a lot of trying, I finally got the dress off. Somehow, even though mom caught me, I really liked wearing that dress.

After my parents were back. We had a long discussion and I got out of it by simply saying I was just fooling around. My mom was angry and she took all of my sister’s outfit & stuffs from the closet afterwards.”

– Emily Fisher


  1. My parents divorced when I was 12. I started to dress up to and feel like the “woman” of the house, not the “man”. One night my mom was out on a date, so I dressed in my mom’s bra, panties, pantyhose, dress, heels, pearls and full makeup! It was so freeing. But, when she came home early, I was caught red handed. My mom was shocked and asked how long had I been doing this? I panicked and said this was my only time. A total lie. The next morning we had a very brief talk and she wrote the event off to the divorce as a one off. I’ve been dressing ever since!

  2. All sounds o so familiar….

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