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Crossdressers Talk About the First Time They were caught Crossdressing

caught crossdressing

Getting caught crossdressing is certainly not a fun experience. It can be a feeling of embarrassment or humiliation for most crossdressers. Since most crossdressers dress in private or secretly, there is a good chance of getting caught if they are not careful enough. Crossdressers can get caught red handed or from their feminine stuffs they forgot to hide properly.

In this article, we have compiled a list where Crossdressers talk about the first Time they were caught Crossdressing.


“In my early childhood, I began to develop quite a fascination in girl’s undergarments. I also became quite curious about stockings and pantyhose. My older sister wore pretty nylon panties and stockings which really had my keen interest.  I was having increasing thoughts about wearing her undergarments & outfits and even started experiencing restless nights trying to sleep.

I could feel the urge to get dressed as a girl increasing very rapidly and it was getting impossible to resist. So I decided during one day to sneak into my sister’s room and try whatever I could find to wear.

I picked the right time when no one was around in the house and went into my sister’s bedroom. I could feel my heart beating so faster and I was very excited. I opened her dressing cabinet and saw many panties and bra neatly folded in one corner of the cabinet. I gently touched them and I could feel how soft and silky they felt.

I picked one pink pantie and held it for a short time in my hands feeling it. I undressed my pants and the under wear that I was wearing and then stepped into the pantie and pulled it up my legs. It was amazing how great it felt. I posed infront of the mirror and couldn’t stop looking at myself.

Then, my attention went to her bra collection. I picked one of her padded bra and tried it on too. It took me quite a while to put in on since I had no experience wearing a bra before. After I finally got it on, I was so excited with the anticipation of wearing girl’s undergarments.

It felt really good and I couldn’t stop admiring myself in the mirror. Then after sometime, I took them off and put them back neatly to their former position in the drawer like it was before. It was my first experience of crossdressing. Since then, I would sneak into my sister’s room and try on her outfits whenever I had the chance.

Few months later, I was home alone one day and decided to dress up. Unknown to me , my sister was coming home earlier this particular day from university. I got myself dressed in her undergarments and also put on one of her floral dress. I was enjoying myself infront of the mirror when suddenly I heard the back door open and that gave me a big fright. I was completely taken by surprise and I didn’t know what to do. I was about to take the dress off when suddenly the door opened and my sister saw me and she was completely shocked.

I was incredibly embarrassed and I couldn’t look at my sister’s face. My sister after a while of trying to understand what was going on, came closer to me and asked me to explain myself. I was so shocked that I couldn’t really say a word. I could noticed that she was angry that I went through her stuffs. I was almost about to cry when my sister told me to sit down on the bed and talk to her.

Eventually I opened up and told her I was very sorry for going through her stuffs and I said I did it because I was really curious about wearing girl’s clothes. I apologized many times to her and she said it was okay. She then started to ask question about when the urges started and how long have I been dressing in her clothes.  I told her couple of times and finally told the truth to her.

She was very supportive and told me it was okay and she wouldn’t tell our parents. I was a bit relieved but still quite distressed after being caught by my sister. After some talking, I went to my room and took off all the clothes that I was wearing and got back into my own clothes. Then I went to my sister and handed her clothes back. She was quite surprised that I was wearing her bra and under wear too.

After that incident, my sister made me promise not to go through her stuffs again and if I really wanted to dress up, I should first ask for permission first.  She explained that it was not uncommon for boys to develop interest in girl’s undergarments and clothes. She told me that if I ever needed to talk about it she would be there to support me. After that, I got a bit relaxed and felt really grateful to have such an understanding sister.”

– Rachel Garner

2 Comments

  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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