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I Remember My First Crossdressing Experience

First Crossdressing Experience

By: aquarius3
Written on October 29th, 2011
It was a dare to wear a bra to school (I was 13) I wore a bra to school under my shirt. The guy that dared me said thought he'd chicken out. Someone else said he must be gay. When I was 15 I wore both a bra and dress in a Zellers cafe. Nobody said anything but there were a few looks and my youngest sister was there wearing a jean skirt. She pretended not to notice. I didn't have the nerve the walk through the mall with the dress on I changed in to my pants and shirt in the washroom marked handicapped.
By: aquarius3
Age: 61-65 , Male
2,553 people have read this story

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4 responses
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    tghubby
    tghubby

    That is great, Aquarius. Obviously your youngest sister now knows you crossdress and no doubt it makes it easier for her to buy you gifts on those special occassions.

    Jan 6
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      aquarius3
      aquarius3

      It was my young sister and she never thinks of buying anyone anything! She just thinks of herself! Wants everything and bosses people around and she wonders why she has no friends.

      Jan 6
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      tghubby
      tghubby

      What a bummer ... it seems like every family as some one like your sister, totally and completely self-centered seeming to think that the world revolves around them.

      Jan 6
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    spunkyblue
    spunkyblue

    That sounded like fun and an adventure for you.

    Jan 6
    1 like