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I Remember My First Crossdressing Experience

The Party

By: RobinLeade
Written on August 19th, 2011
Age: 22-25
8,154 people have read this story

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22 responses
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    angiecan

    I would love to have a Mother like yours...;-)

    Dec 20, 2012
    1 like
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    bethanngirl

    Great story. I would really enjoy that.

    Dec 20, 2012
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    amytheinvalid

    A great story. As much fun to read, as to dream of such a life.

    Oct 14, 2012
    1 like
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    special225

    I agree that is some fantasy. Please write more on your journey.

    Oct 12, 2012
    1 like
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    majellastgerard2

    (boing) *****.

    Oct 5, 2012
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    Ddsmen

    The fact that they bought you all those outfits, I hope they kept you using them. How wonderful to have someone to support and enhance your feminine desires.

    Sep 28, 2012
    1 like
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    golfer10

    What a great story! To have that experience and support to dress and then go out in public in an accepting environment is a dream.

    Aug 13, 2012
    1 like
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    tghubby

    What a wonderful story and WOW to have the help of two women, one being your mom and the other her friend, to help you perfect your feminine presentation before the party. And what a neat time you must have had ... I've been with my wife to some lesbian gatherings and it has been great, being accepted as a woman, even those who knew I had a little secret in my panties.

    Jun 15, 2012
    2 likes
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    KatyPerryLover2012

    I love this story sooo much!

    Jun 15, 2012
    1 like
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    ashleyfield

    I grew up in womens' world - mom, her mother and my 2 older sisters. With all of these ladies about, it was easy to purloin a few articles of clothing. What I could NOT steal, however, was the loving support you got as a young one. Hurray for you!

    Nov 2, 2011
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    NikkiNorris

    That's some fantasy.

    Sep 11, 2011
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    Brandie1960

    My first crossdressing experience was also for halloween when i was 13. My mother suggested it and i only got to wear everything for that night but it planted the seeds of a life long passion.

    Sep 8, 2011
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    roxanna105

    lucky girl the perfect introduction to womanhood

    Sep 7, 2011
    2 likes
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    happilymarriedguy

    Great story.. You were very lucky

    Sep 4, 2011
    1 like
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    Babylon55552000

    You are so lucky.

    Aug 30, 2011
    1 like
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    SaraDoes

    What a wonderful party!!

    Aug 29, 2011
    2 likes
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    nbg56

    Gosh Robin, What a wonderful fairytale story this is. What a wonderful mom you have. I wish I could have talked to my wother when I was younger about my feelings as a girl.

    Aug 20, 2011
    2 likes
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    Rowena68

    Sounds like you had some very caring and understanding ladies in your life. So what did you figure out after your experience at the party?

    Aug 19, 2011
    3 likes
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      RobinLeade

      I figured out who my Mom and Cheryl were. And that I wanted to be just like them.

      Aug 19, 2011
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    Melodie13

    Other then school, did your mom further encourage you to stay dressed as a girl. Mine did. I actually like wearing the dresses, I felt better then when I had to wear boy clothing..

    Aug 19, 2011
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      RobinLeade

      No they never encourage me. But when I did dress they made sure I was the girl my age. As I got older I had more girls clothes then boys.

      Aug 19, 2011
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    skedish

    It's wonderful that you had people around you that took the time to help you from beginning to end. In my case I had to learn on the fly, a little at a time, how to dress well. I don't know if there was any intent on Cheryl or your mother's part beyond having an exceptional Halloween costume, but it's so nice that this experience opened the door for an important part of your life. Thanks for sharing.

    Aug 19, 2011
    4 likes