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Thread: When did you first crossdress?

  1. #101
    Junior Member kathy chelan's Avatar
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    Apr 2012
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    The first time I know of for sure is that I remember I would put on my sister's sandals when she took them off while we were playing outside...this was probably about when I was 5. She is 21 months younger than I, and I could wear most of her things until about high school age when my growth spurts started---girls have them earlier, you know. At age 6 in first grade, I had a short walk to where she was babysat all day, along with another girl her same age named Betty Ruth H. They had a habit of taking their shoes off and putting them under the edge of a table. When I got there I would wear Betty Ruth's shoes---black patent leather (ballet) flats. Mrs. K kept all 3 of us until my mom picked us 2 up after her work, about 6 pm.
    Once we were invited to go swimming with the family of the girl next door to us who was my sister's same age. Sis didn't have a suit. so they loaned her what was then called a two-piece "sun-suit." That evening when we were at home and this was hanging to dry in the bathroom, I put it on and walked around like I did Betty's shoes at Mrs. K's. When my dad saw me, he bellowed at the top of his lungs for me to take that off and never to let him catch me doing something like that again. I sure didn't. From then I dressed in secret only, apart from a few times I talked mom into "dressing (me)up like a girl" to go trick-or-treating. Mom still had a matador costume from her high school years and both of us used that a time or two.
    Once at Mrs. K's, she had twin granddaughters visit her (they were at least 5 years older than us 3), and they played with us while their mom was inside with Mrs. K, her mom. Since I again was wearing Betty's shoes, they suddenly decided they wanted to dress me up like a girl. I was thrilled inwardly, but dare not show it outwardly. But suddenly they were called to get ready to leave. I didn't let on to my sister or Betty but I was inwardly very disappointed. From 2nd grade on, I always wore my sister's things when no one else was home, and I was a sickly kid anyway.

  2. #102
    New Member jeni's Avatar
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    Dec 2015
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    NJ
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    My first time was when I was 16. It was in my neighbors Apartment she was dressing her self at the time. Wearing my first dress I felt at home with my self.

  3. #103
    Member laura.lapinski's Avatar
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    May 2007
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    I had some thoughts at a very young age, and I put on a one piece stretchy, skin tight bathing suit when I was 13. Loved it.

  4. #104
    Banned Read only
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    Sep 2009
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    "Upstate" NY USA.... Site of the first crash of the "Vin Fiz"
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    OK....
    I was born in '47 and had a sister 4 years older than me, and another sister that was 4 yeas younger then me.
    Yeah, I am the middle child.

    So early on, I had access to all that great 1950 lingerie and other female clothes from my mother as well as from my older sister... I was attached to their clothes... even before puberty.

    When was almost 9 years old and my older sister was 13, she had made the transition to adult lingerie and clothes.
    I kept wondering how wearing those clothes felt....
    I cold not fight it anymore. At about 9 years old, I had to find out,
    So, when I got the chance in private, I started with panties bra, slip Eventually I often added gaiter belt and stockings, a dress or skirt / blouse .
    My sister's (and mothere's) clothes were just a bit big on me but, I absolutely love the way they felt.... they felt so right and pleasant .
    I loved feeling feminine/girly.
    Last edited by Barbara Jo; 06-21-2018 at 07:52 PM.

  5. #105
    🙊🙈🙉 Patience's Avatar
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    5 or 6, from what I remember.

    It felt right the moment I put it on.

    Xox,

    Tina

  6. #106
    My BF and Style Guru Millisense's Avatar
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    Jun 2018
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    NE USA
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    I was fortunate enough to have a much older sister so there were always clothes of hers from various ages to be found in the attic or her bedroom after she left for college -- skirts, panties, pantyhose, everything. Just recalling those lovely afternoon dress-ups 50 years ago sends nice shivers, so thanks for the thread!

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