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I Remember The First Time I Was Taken Out Dressed As A Girl

Going Out Dressed Like A Girl Wasn't Necessarily What I Was Planning,

By: kayleew2000
Written on March 25th, 2012
Age: 18-21
2,256 people have read this story

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27 responses
  • angiecan

    I can imagine some mental anguish of being a boy dressing as a girl. Then secretly enjoy the Loving attention you are receiving your mother and wanting her approval. ;-)

    6 days ago
    1 like
    • kayleew2000

      That's a good comment, Angie. I think that pretty well sums up my life from 8 to 14 or so.

      6 days ago
      1 like
  • Aiyana77

    I imagine that first trip out must have been a bit nerve wracking. i know I would not have been happy about it.

    May 8
    1 like
    • kayleew2000

      Nerve wracking? ...yes. Was I unhappy at first? ...probably. Embarrassing? ...certainly. But it did not take long to discover the excitement of strolling through the malls shopping with my sister and mother. Through the years we looked forward to our little shopping excursions almost every weekend.

      May 9
      1 like
    • Aiyana77

      That is awesome. I never got along with my parents and sisters enough to even consider the idea of knowing I like more feminine stuff let alone be completely open about it. Still don't and have no intention of letting them in on it as they are some of the most judgmental people I know

      May 9
      1 like
  • leona1976

    Do you ever wear jeans or trousers kayleew x

    Sep 22, 2012
    1 like
    • kayleew2000

      Almost never growing up but I did get a pair or two to wear in the winter and I still have a couple pair now. They are cute with plenty of bling on the pockets.

      Sep 22, 2012
      1 like
  • AnnaliseB

    What a lucky girl you are!

    Sep 21, 2012
    1 like
  • betty3100

    Did you get a pair of heels that first day out shopping?

    Aug 13, 2012
    1 like
    • kayleew2000

      Funny... I don't exactly remember what kind of shoes we bought during those first few shopping trips. I remember wearing small heels some of the time in the early years but mostly they were wedgies or low heel shoes with colorful designs and bows. The first pair of actual "high heels" that I remember were a birthday present when I was about 12. I had to dress up to go to a wedding for a friend of my mother's. They were red open-toe pumps with a cute bow over the toes. I felt so grown up. Before that I just played around in my mom's heels, and of course, now I have at least 25 or 30 pairs of heels in my closet. If I could afford it, I would probably have twice that many ... :-)

      Aug 14, 2012
      1 like
    • betty3100

      What did you wear to the wedding you spoke of? How high were your heels then?

      Aug 15, 2012
      1 like
    • kayleew2000

      The heels were black sandals with a pink trimmed black bow. They were only about 2 1/2 inches or so ...but not wedgies. They were my first thin heels and I felt like I was walking on my toes all day. I wore a simple short black sequin dress with a black thin string bow in back. It also had a handful of pink heart-shaped sequins scattered all over and a thin pink high-waist belt. I loved that dress and talked my mom into letting me wear it on special occasions. I so miss those innocent days of dressing up in pretty clothes.

      Aug 16, 2012
      1 like
    • betty3100

      OMG that sounds simply beautiful, Kaylee! I assume that you also wore stockings. Did your mom help you get dressed for the wedding? Since I am physically challenged my mother had to help me most of the time to get dressed. She was a stickler about my appearance and my femininity. Guess that's why I ask so many questions about stupid stuff. I, too attended weddings and other events as a girl. First wedding I attended as a girl was when I was 9. Mother and I wore matching pale yellow long dresses with matching pumps. That was the first time that I wore a two inch heel and did fairly well walking. Did your mom dress you often? Mine did only because she knew I was a girl really inside. Would love to hear more about your experiences as a girl..

      Aug 17, 2012
      1 like
    1 More Reply
  • Brandie1960

    I really do believe if more parents did this theirs sons would love and cherish the experiences for the rest of their lives.

    Aug 13, 2012
    1 like
  • theBillyandBudBear

    I am sorry that I missed this wonderful story of your first venture out into the world with silky panties cradling your widdle dragon and a sissy slip and dress swishing around your bare legs sending sensations up to the brain and every nerve ending in your body tingled with fear and excitement. Gad!

    Jul 31, 2012
    1 like
    • kayleew2000

      Even now, after a dozen or so years in girlish clothes, I wonder why fear and embarrassment are still a secret part of my feminine enjoyment. I guess only those of us who have walked both sides of the path can truly appreciate these feelings.

      Aug 1, 2012
      1 like
  • Gauchito

    Lucky you being in such good family!

    Jul 22, 2012
    1 like
    • kayleew2000

      It took me a few years, but I finally did learn to appreciate how wonderful they were to me.

      Jul 22, 2012
      1 like
  • SaraDoes

    Being embarrassed is part of the reason it is so remember-able!!

    Jul 2, 2012
    2 likes
  • kayleew2000

    I look back on those first trips out in public with a sense of humor although, I remember them being very traumatic andembarrassng.

    May 19, 2012
    2 likes
  • angiecan

    Thats the experience all wish we had. To be our mothers little girl.

    May 19, 2012
    1 like
  • sammi11

    Wonderful Kay

    I've always found sales ladies to be very helpful - especially with bra fitting

    Hugs

    Sammi

    Mar 29, 2012
    1 like
  • LadyBeverly

    at that age never fear the sales people selling you girls clothing and such, unless you are alone, I find when I accompany the sales people relax and enjoy it.

    Mar 26, 2012
    2 likes
    • kayleew2000

      Of course, those fears were some years ago. I think i learned like most girls how wonderful shopping for clothes can be.

      Mar 26, 2012
      1 like
  • ashdowd

    my mother allways take me out as girl

    Mar 26, 2012
    1 like
  • Melodie13

    Like I've said numerous times OUR MOMs know us so well, she sees the little girl in all of us boys, unfortunately only a few are brave enough to assist us in bringing her all the way forward.

    Mar 25, 2012
    1 like
    • kayleew2000

      I went from resenting my Mother to learning to how wonderful life could be. I suspect i was most fortunate to be home-schooled and not have to deal with the cruelty of narrow-minded highschool boys. Although I had not purposely sought a feminine lifestyle, I learned to love being part of the secret inner circle living only with my sister and mother.

      Mar 26, 2012
      1 like