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I Remember My First Crossdressing Experience

Debbie Did It To Me!

By: jackson87
Written on February 21st, 2013
My first time crossdressing was when I was 12 and my cousin Debbie did it to me. I was staying over at her house when our parents were gone for the weekend. Debbie was 16 and a very pretty blonde. It started with her being bored and wanting to go out, but she had to be with me. I was a small boy and at the time I had fairly long hair. Debbie thought it would be fun to put makeup on me. I couldn't really stop her as she was bigger and stronger. She made up my face, curled, and styled my hair like a girl's. We both were shocked because I looked pretty. Next thing I know, she is stripping me and soon I was dressed in stockings, heels, a tight corset and panties. Debbie spent the whole afternoon dressing me in her and my aunt's clothes. I remember loving the feel of the silky, frilly bras and panties she dressed me in. Finally she took me out to the movies with me dressed like a teenage girl. The boys at the show paid a lot of attention to me...as a girl. In my heart I will never forget and continue to dress up in my wife's clothes when she is away. I buy very sexy lingerie for her, not so she can wear it, but so I can dress up in secret.
By: jackson87
Age: 31-35
1,002 people have read this story

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6 responses
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    LilChrissy
    LilChrissy

    Wonderful real life experience! And glad it was such a positive one, with both your cousin and being out in public (the first of many times I hope). But seems that today you are keeping your cross-expression a secret from your wife, so have to do your dressing up in secret. Unless she is extremely conservative and insecure why don't you try sharing this secret with her? And likely she will either be neutral, support you doing so without her around, or maybe even allow you to fully dress around her. If you have a solid and supportive relationship, most times the long-term positives will outweigh any initial negative reactions.

    But I understand the initial fears and possible drawbacks given I was once in a similar position myself, and kept this desire/activity from my (past) spouse, which I feel hurt our relationship since this side of me was so strong to my inner being. The trick is to share one aspect at a time, and not let her imagination run wild with what it means (you need to tell her what it means) or that you will turn into a woman and leave her. Or that she is not "enough woman" for you and your marriage. Just alleviate such fears on her part will help a lot towards tolerance and acceptance. The future rewards can be very fulfilling for you and your relationship.

    I well remember the first time I wore a dress around the house and helping to fix dinner that night with her. Such a relief to share this side of me and made for such a wonderful time. Good luck with being more open about your "secret." with her. And once again, a great story!

    Mar 8
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    boyjaybee
    boyjaybee

    OMG thats almost exactly what happened with me. My cousin (girl) was the one that first dressed me up too and I loved it OMG what a great feeling

    Mar 7
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    HighheelWendy
    HighheelWendy

    I started crossdressing at a young age & i am 41 yrs old & still crossdress. When i was married i would use Halloween as an excuse to dress up. I have my own wardrobe & live alone, so i dress whenever i feel like be feminine.

    Feb 21
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    GrandestMother
    GrandestMother

    no offense Jackson, I just wonder why all you guys claim the girl that crossed you
    is bigger and or stronger- I wish just once to read- I could have stopped her easily, but
    for some reason didn't

    Feb 21
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    Kim1girl
    Kim1girl

    Your settings don't allow anyone to add you or send you messages. That will make things boring. If you like, send me a message (see menu on left side of your profile page) and I'll tell you how to change these. Or add me by clicking below my Avatar.

    Feb 21
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    Kim1girl
    Kim1girl

    That had to be so much fun. I always wanted a girl near my age to dress me when I wa young. Did you ever spend another afternoon session with Debbie?

    Feb 21
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