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Thread: When did you first crossdress?

  1. #1
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    When did you first crossdress?

    Looking back, I can remember putting on my mum’s coats when she wasn’t around and admiring myself in the mirror when I was 7 or 8.

  2. #2
    Somewhere in-between. Krea's Avatar
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    I think many here have childhood origins to their CDing, so i'm probably in the minority coz i only began crossdressing a few years ago. (i am forty-something)
    Looking back tho i have always had much insecurity about myself, without actually knowing what caused it and i feel much happier about who i am now i can crossdress with the support of my wife.
    "Welcome to my scene.
    A place that's in-between.
    Where the squares fit the rounds."
    (Lyrics by Queensryche)

  3. #3
    Stand-up Comedian En Fem❤ Alice_2014_B's Avatar
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    Completely from wig to heels was around January 2014.
    Melissa: "... and why are you dressed as a woman?"
    Coach McGuirk: "Because it's freeing."

    -Home Movies
    (cartoon series)

    Shoe size: 9 US women's.
    Dress size: M to L; 8-10.
    Height: 5' 6".

  4. #4
    AKA Lexi sometimes_miss's Avatar
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    The first time I wore girl clothes was as a toddler when mom dressed me in my older sister's hand me down clothes, ostensibly to keep my from ruining my 'good boy' clothes. She also kept my hair long, I remember her giving excuses like running out of money, or time and needing to catch the bus when at the end of a day shopping when she had planned to get my hair cut. This went on until I was just past three, when my dad came home for lunch early and found me in a dress and blew a gasket. So that stopped, as well as him deciding to take me to his barber regularly from then on. The first time I dressed myself in my sister's clothes was when I was four, she, getting ready for school and mom getting her prettied up and doing her hair, I went and put on a dress and then went and told them that I was ready to go to school, too; basically probably a maneuver to get mom's attention to me. Mom simply changed me back, and we took my sister to school. When we came home, she asked me if I'd really like to wear the dress, but said it in such a way as to imply that my answer should be NO (as in, "you don't really want to wear a dress like your sister, do you?"). So that's how I answered, even though my feelings were actually 'YES'. But it wasn't a statement of wanting to be a girl, just not wanting to be dressed in my worn out ugly boy clothes, and of course, wanting her to be nicer to me. Mom was a first born, as was my older sister, and so mom sympathized with sis whenever sis complained about me, because mom resented her younger sisters when mom was young, and still did throughout her life, often complaining that she had her life limited because of her own mother's insistance that mom watch over her sisters, and that her sisters always were shown preference instead of her. So I suppose my mom's behavior showing preference to my sister might well have made me feel that it would have been better to be a girl, instead of a boy. Still, this didn't make me feel any more female at all. That would change a few years later, when I was molested, and told that god had made a mistake, and that I was really supposed to be a girl. He presented his reasons, which at that age, I wasn't able to debate. So, thinking that I was supposed to be a girl, I developed a desire to dress as one and behave as one, in order to be good and hope that god would eventually fix my body, too. My abuser dressed me in his younger sister's clothes regularly, and over the next seven years, made me into his own personal girlfriend. By the time high school rolled around, the notion that I was supposed to be a girl, and wear girl clothes, was firmly set into my mind, and even though all evidence that exists tells me that it isn't true, the feeling has never gone away; I still feel like I'm supposed to dress and behave like girls do. The problem is, I'm not attracted to boys, only girls. And I don't see and experience the world as girls do, nor communicate like they do, or behave as they do. Whenever I got the chance, I would scrounge up some of my sister's old clothes to dress up in, always hiding it from the rest of the world. So I'm in an odd position, feeling like I'm TS while retaining my male desires and thought processes. I'm neither all girl, nor all boy. And for the past almost 50 years, have felt like an adolescent girl, forever waiting to become a woman. Needless to say, despite praying endlessly throughout my childhood, god never got around to answering my prayers or fixing my body. The whole story is in my bio, link is in my sig at the bottom of thiis post.
    Last edited by sometimes_miss; 04-07-2018 at 09:48 AM.
    Some causes of crossdressing you've probably never even considered: My TG biography at:http://www.crossdressers.com/forums/...=1#post1490560
    There's an addendum at post # 82 on that thread, too. It's about a ten minute read.
    Why don't we understand our desire to dress, behave and feel like a girl? Because from childhood, boys are told that the worst possible thing we can be, is a sissy. This feeling is so ingrained into our psyche, that we will suppress any thoughts that connect us to being or wanting to be feminine, even to the point of creating separate personalities to assign those female feelings into.

  5. #5
    Senior Member NancySue's Avatar
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    When I was 5 or 6, I found a pair of mom’s sheer nylon stockings. Don’t remember “why”, but felt a strong urge to try on...and did. That was the kickoff and the game continues.

  6. #6
    Yeah Ok like whatever Tracii G's Avatar
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    1968 I was 15 went to the prom.
    Head Executive Chief of the Dept of Redundancy Dept.
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  7. #7
    Platinum Member Beverley Sims's Avatar
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    I think about four or five when playing mothers and fathers with older girls.

    I was the little baby as I could be put in a large pram and wheeled about.

    I thought this was good fun as I was given a bottle with warm cocoa in it.

    That I did enjoy, I liked cocoa.

    After that I think it all got imprinted on me like a chicken to the mother hen.
    Work on your elegance,
    and beauty will follow.

  8. #8
    Member wanda66's Avatar
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    In the beginning.......

  9. #9
    Crossdresser Taylor186's Avatar
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    I was six when I fashioned a dress out of a towel. (Is that crossdressing?) I was seven or eight when I discovered stockings that were hanging on the towel rod to dry. It progressed quickly from there.
    Last edited by Taylor186; 04-07-2018 at 01:58 PM.

  10. #10
    Carole carhill2mn's Avatar
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    About age 8 when I put on one of my mother's silk blouses. It fit me like a dress and I loved it! Soon I was wearing her wedding dress as often as possible.
    Hugs, Carole

  11. #11
    Junior Member Paula2's Avatar
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    Nice question..I cannot tell you when I started..1976??
    I have done it all my life..I cannot tell you when I started..I have done it since my very first memories..And yes Taylor I too remember making skirts out of towels..LOL..now they are called "Wrap Skirts"
    Last edited by Paula2; 04-07-2018 at 12:09 PM.
    Best Wishes, Paula

  12. #12
    Stop that, it's silly.... DIANEF's Avatar
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    I first wore a dress when aged 15, that was in 1979. Many years before that all I had worn was underwear and swimming suits, after that I only ever wanted to fully dress.
    Last edited by DIANEF; 04-07-2018 at 12:22 PM.
    Here today, gone tomorrow....

  13. #13
    Junior Member jaerina96's Avatar
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    I don’t really know, literally it’s been as long as I can remember. I don’t remember trying on my first dress. By the time I was 10 I was already “wig to heels” in the hours between getting home from school and when my parents got home from work, a mix of old dresses my mom kept in the trunk with the Halloween costumes and things I snuck out of the bags of stuff that was supposed to go to Goodwill. I’d pad bras with polyester filler, and had a cheap old costume wig. Things fell apart after getting found out a few times and lectured / screamed at about it being a sickness and going to hell, that sort of stuff. Body hair was the real killer for it, I couldn’t get rid of it without being noticed and it grossed me out so bad that I couldn’t continue. Then I ended up in one of those church youth cults, went through a very very long self-hating religious phase, and after an extremely bad prolonged depression stopped fighting it and started again around when I turned 30. First time out in public was less than a month later. With the exception of a year and a half pause when I had a serious relationship, it’s been a regular part of my life ever since.

  14. #14
    New Member Jenny Brogai's Avatar
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    I started around 12 or 13 with my mum and my aunts stuff, never forget the thrill of it! The first time I dressed up in a wig and heels, I was 25.

  15. #15
    mini kilted chick t-girlxsophie's Avatar
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    When i was 10 in my Gran's house,first wore my aunties clothes that she had left there,still can't explain what drove me to do it
    We look to Scotland,for all our Ideas of Civilisation-Voltaire

    ========================================

    A woman who loves to wear beautiful clothes is like a flower.
    A man who loves to emulate these women is a special flower-a rose
    Facebook:Sophie Johnson

  16. #16
    Yeah Ok like whatever Tracii G's Avatar
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    Sophie I don't think any of us could answer the question why and trying to pinpoint an answer is a fruitless venture that just causes more questions.
    Head Executive Chief of the Dept of Redundancy Dept.
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  17. #17
    18 yo Girl <3 Chloe Triss's Avatar
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    Around like 11 years old when I was alone in my house for the first time, I went on and wear my aunt favorite victoria secret undergarment set and her big red black spotted dress.

  18. #18
    Gold Member Lana Mae's Avatar
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    Mom's undies in elementry school! Mom's nylons, long leg pantygirdle, bra and full length slip in my teens! Fully; wig, forms and make up going on 3 years! All started when Lana(my namesake) flipped her dress over her head and I wanted a dress to flip over my head! LOL Hugs Lana Mae
    Life is worth living!
    "Foxy lady! You look so good!!" Jimi Hendrix

  19. #19
    Gold Member Diane Smith's Avatar
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    Among my first clear memories are my mom letting me try out her lipstick and earrings at about age 2-1/2. Nail polish followed soon after. No clothes at that point, but by 5 I was playing with her shoes, stockings and girdles.

    - Diane

  20. #20
    New Member Esther Latour's Avatar
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    When I was in the first year of art school, at a fancy dress party. It was supposed to be ironic but of course it really wasn't. I had been having fantasies about it for years.

  21. #21
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    7 or 8 when I was left home alone for a little while

  22. #22
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    I was around 5. I found one of mom's bras. By the time was a teenager my mom's and sister closets were my playground.
    Sara

  23. #23
    Silver Member Jodi's Avatar
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    Eight years old. Discovered my moms high heels

    Jodi

  24. #24
    Super Moderator Raychel's Avatar
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    i was probably 7 or 8 when I first started with the underwear and pantyhose.
    that progressed over the year to full dressing when I was 43. It has been almost 15 years now.
    Everyone has there thing, all that matters is that you are happy, love what you do and who you do it with

  25. #25
    Member Jenn_8B's Avatar
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    I don't know when I first cross-dressed. I can vaguely recall trying on some of my mothers clothes, probably as a teenager. I have been overweight most of my adult life. About 10 years ago, I lost a lot of weight and started trying on some of my wife's things. Several years later as I gained the weight back, I had a desire for "softer / sexier" clothes than men's clothes. Somewhere about then I started wearing panties with my wife's permission and things grew from there.

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