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Thread: When did you first crossdress?

  1. #51
    Aspiring Member Chiana's Avatar
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    Like many here. Very early 3 or 4 yo at the latest. I had no idea there was anything wrong with it. I clearly remember the first time I realized that being a "girl" really wasn't OK. When I was 5, I told my Mom "When I grow up, I want to be just like Beverly". Beverly was an older girl that lived across the street. The look my Mom gave me set off alarms.
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  2. #52
    Member Aylineira's Avatar
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    Earliest memory of myself crossdressing was putting on high heels and boots when I was extremely young. Definitely around age 5 or 6.

  3. #53
    Junior Member kimberlybates's Avatar
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    I believe I was about 11-12 when I first slipped into a lovely blue long nightgown that belonged to my Aunt. I was hooked at that point.

  4. #54
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    I never had any sisters, but I remember a day that one of my mum's friends' daughters was over, and she was a similar age to me. We must have been about 4 or 5 and she had on these black patent Mary Jane shoes. I could hardly take my eyes off them and really wanted a pair, although I had no idea why. I also remember when my beautiful Aunt Steph used to come over and, although very young, I was quite taken with how beautiful her legs looked with her nude tights and shoes. Then I remember getting out of the bath once when I was about 6 and my parents were both downstairs. There was a pair of tights and a skirt on the floor of their bedroom. As I was only wearing a towel, it was easy for me to try on the tights and then the skirt - I was genuinely curious as to how they felt. Of course, I was hooked.

  5. #55
    Member jackie_p's Avatar
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    Around 8 years old. I tried on my sisters Cheerleader outfit. Been hooked even since.

  6. #56
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    Hi Alexs, Some where around age five 65 years ago .
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  7. #57
    Neanderthal in nylons Julie Denier's Avatar
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    Clomped around in Mom's shoes when I was very young, maybe age 5 or earlier. Explored other parts of Mom's wardrobe periodically through high school. Never dressed fully until about 2 years ago.

  8. #58
    Junior Member lynnmcarthur's Avatar
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    I was 3 or 4 when I first remember being sure that I knew that being a girl would have been better for me

  9. #59
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    I didn't have a sister or brother. Girls were of no interest to me until, aged around 12 or 13 (1957) I began to notice some girls about my age who waited on the same station platform. One or two of them had started wearing nylon stockings - as did the older girls. All the schools were single-sex so I had only a few minutes each day to observe the girls and was fascinated by their legs, wondering what it must be like to wear stockings. I also wondered how they held them up. I knew my mother wore girdles but I had no idea if these younger girls did likewise. I didn't know any girls well enough to ask. After a while I decided to borrow a pair of my mother's stockings and try them. It was a pleasant experience but, with nothing to hold them, it clearly wasn't exactly how the girls wore them. So, I managed to find an old girdle which I don't think my mother wore any more and put it on. It wasn't a very tight fit and I remember wearing a leather belt round my waist to keep the girdle from slipping down. At that stage I wasn't interested in bras or slips but I did try on one of my mother's summer skirts and loved the way it felt to have my legs in nylons held up by suspenders and shrouded by a loose, swinging skirt.

  10. #60
    New Member dyane's Avatar
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    Must have been when I was about 13, Got interested in girls and what they were like under their clothes, so I 'borrowed' my sisters day of the week panties. Each day was printed on them. Mom's bras, girdles, nylons and dresses soon followed. Been dressing ever since

  11. #61
    Member Vanessa Amber420's Avatar
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    When I was 8 I tried on my cousins panties. I remember liking how the felt on me and the way they looked on me.

  12. #62
    Comedian Emma Beth's Avatar
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    I think the first time I tried on women's clothing is when I was a preteen going through my mothers drawer. The most significant memory was when I was in the military. It was a bachelor party gag for one of my best friends. My girl friend got with her boss at the strip club and we put together something I could do on stage. The other dancers worked with me for weeks to put together the most convincing performance. When all was said and done, it is a very fond memory; and I think I made about six hundred dollars in tips that night and my friend had the shock of his life.

  13. #63
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    I was 6 years old playing mums & dads with my sister when she suggested I be the mum. She helped me into one of her skirts & I knew right away I was different. It felt so right to me & the feeling of being feminine was overwhelming. I'd lay awake at night wishing I was a girl & it became my deepest secret. I didn't think anybody would understand.
    So I grew up the normal little boy my parents expected me to be, but in secret I'd dress whenever I could. I was fascinated by clothes & makeup & I adored the way it made me feel, just getting to be like a girl even for the shortest period of time.
    It just snowballed from there, I'm 38 years old now & just a 'normal' guy to those who know me but I still love to do this, I feel like I need to.

  14. #64
    Silver Member Angela Campbell's Avatar
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    I can remember way back when I was no older than 4, trying on my mothers things. I also remember when in the bath I would take washcloths and lay down and use them as clothes, laying one across my bottom as if they were panties, and one across my top as a bra, then one over these as a slip, then another as a shirt and then a skirt, Somehow even then I knew that women dressed in layers that boys just didn't do, and I wanted to do that. For the rest of my life whenever I saw any female I always noticed how they dressed and carried themselves. So jealous that they got to look like that and I didn't.
    All I ever wanted was to be a girl. Is that really asking too much?

  15. #65
    Seasoned Member Rhonda Darling's Avatar
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    I remember somewhere before age 6 stuffing a couple of small towels into my shirt as mock boobs. Shortly thereafter I discovered the dirty clothes bin, and all of mom's silky underwear, bras, girdles, slips, etc. I'd raid the bin while supposedly going to the bathroom and try everything on. It was heaven. I played dress up with the neighborhood girls in a playhouse one of them had. As I grew up, I found many times when I could secretly dress for short periods of time. That was done more for the sensation of wearing frilly things -- a great sensation for a pre-pubescent boy. In jr. and sr. high I gravitated to the school theater department and the world of dress up clothing expanded exponentially. It was on to the "second star to the right and straight on 'til morning" after that.

  16. #66
    Member Adrienna's Avatar
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    I first got the taste of dressing when I was apprx. 4 or 5 years old. Just out of curiosity I suppose I got into my mother's stuff, can't remember where, and tried a few things on. Been hooked off and on ever since. I always thought it a strange thing too until I realized that I'm in good company here. Funny what one remembers over the years. I also developed a heavy boot fetish along with leather and pvc clothing as well. Dipped into the world of femdom off and on dressed as a dominatrix which was/is a total thrill to me. Go figure the tangents to all this but all good and fun!

  17. #67
    Silver Member Angela Campbell's Avatar
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    I am not sure but I think it was when I was 3 days old and my mom washed one of my diapers with one of her red shirts and I ended up in a pink diaper......
    All I ever wanted was to be a girl. Is that really asking too much?

  18. #68
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    I was about 6 or 7, tried on one of my mom's dresses when she wasn't home, felt perfect!

  19. #69
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    I was 4 or 5 when my mom dressed me in a pink party dress. It seemed like a natural thing to do at the time for me. I started dressing myself at 10 years old and never stopped...

  20. #70
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    started when I was about 19 yrs old.

  21. #71
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    Wink Woo Hoo!

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  22. #72
    Discovering the Gurl Xandra's Avatar
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    Thanks everyone for sharing your memories. A common thread running through most of our posts is the similarity of the experience of dressing at an early age and knowing at once that we had opened the door to another world.

  23. #73
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    I was five and wore a dress of my mother's to play outside with a neighborhood girl. I know there were other times through childhood where I tried other clothes, heels, makeup and my mother's wig. I mostly left it behind in my teen years. After I was married, there was a handful of times I tried on my wife's things. I'm really now just thinking about it seriously and starting to experient a bit. It great to have all of these resources online!

  24. #74
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    Quote Originally Posted by Rhonda Darling View Post
    Shortly thereafter I discovered the dirty clothes bin, and all of mom's silky underwear, bras, girdles, slips, etc. I'd raid the bin while supposedly going to the bathroom and try everything on. It was heaven.
    Definitely been there,at age 9 or 10 i think

  25. #75
    If only you could see me sarahcsc's Avatar
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    Hm... around the same age of 7. I couldn't remember what I loved wearing at that time but I remember my mother dressing me up as a joke and I enjoyed it. ^_^
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