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Thread: When did you first crossdress?

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  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
    Non-Binary Member 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.
    "The only way is onward. There is no turning back."

  3. #3
    Platinum Member alwayshave's Avatar
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    I know I was about 4 or 5, my mom kept stuff on the stairs to the attic which was in my room.
    Please call me Jamie, I always_have crossdressed, I always will, "alwayshave".

  4. #4
    Member Diane Taylor's Avatar
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    I was a late bloomer if you mean fully dressed. I didn't fully dress until I was in my 40's. if you mean a few items of underdressing, I was in my 30's, but when I was 8 my mother made a Halloween costume for me that included one of her short dresses and some lipstick.

  5. #5
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    Not so young

    I seem to be in the minority, like Diane. I can't remember really ever having a strong compulsion to cross dress until the past few years, and I just turned 60. I don't think I had been purposefully suppressing something, but maybe I was. Who knows. But I certainly enjoy it now.

  6. #6
    Member elliemoss's Avatar
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    I was about 13/14. Out of nowhere I started to notice what ladies were wearing on TV and at night time in bed I was bombarded with thoughts of femme clothes. I finally gave in to an over bearing urge to try on some of my sisters dresses and skirts. It felt amazing and ever since then been hooked. Wassn't until about 10/12 years later until I fully dressed up with wig/full make up/heels. My GF at the time was away for the weekend so I had a girly Satruday watching girlie movies, TV then got dressed up and walked around the block late at night. It was such a unique thrill feeling the cold November wind blowing my dress against my legs and the clipping sound of my heels on the pavement.

  7. #7
    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".

  8. #8
    Senior Member Tracy Irving's Avatar
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    My best guess is somewhere in the six year old range when I discovered how wonderful it felt to wear my mothers panties.

  9. #9
    Senior Member kayegirl's Avatar
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    It seems so long ago now that it's hard to be precise. I had been playing dress up since the age of 5 or 6. Somewhere I even have a photo of me wearing my sister's bathing costume. But I was 13 when I first consciously dressed full girl. Home alone and again with my sister's clothes. For me it was a true epiphany, and I knew that I wanted to be that girl forever afterwards. Sadly it took many years before I could be as open as I am now, but that's another story, and too long for now.

  10. #10
    Member Sandra_Dodds's Avatar
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    Somewhere around the age of 7 or 8, when I first tried on mum's tights. I have a distinct memory of being in primary school and seeing a girl in tan colored tights with white knee-high socks and being totally fascinated with how those tights looked and felt.

  11. #11
    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.

  12. #12
    Silver 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.

  13. #13
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    1968 I was 15 went to the prom.

  14. #14
    Resident Polymath MarinaTwelve200's Avatar
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    I started with Mom's lipstick at age 12------Since I was 8 In the late 1950's,I remember the (joking) threats by Mom other women and older girls at our consolidated School, to put that red 1950's lipstick on me. The idea horrified me. especially since I thought it would not come off. The worry was for naught, none of them ever followed through with their threats----Although I came pretty close when, at a whim, Mom had dad hold me down, one time, to actually do just that, but "chickened out" at the last second "I don't know, it might give him a complex" was her excuse.-----But the prospect fascinated and horrified me for years later---at about age 12, I was left alone at home for some hours, and decided "what the heck, GO for it!" I first tried a touch on my wrist---and behold! it wiped OFF!---Then on my lips it went.----at age 13 I tried on a girdle, some panties and nylons from the laundry---THEN, (why not) a bra (stuffed with my underwear) and a slip and finally a housedress to top it off---Then Lipstick (of course) and a scarf to cover my head.---I was Completely Dressed! ----And continued (with some breaks) when I could, to this day.

    I still have some "holdovers" from my roots--I need the darker shades of red Lipstick to really feel "dressed". Yes, I have tried other shades, and I really look good (if not better) in them, but I just cant get my "rush" in anything without the red lipstick. (the 50's influence is still there, I suppose) Perhaps it is a "fetish"
    Last edited by MarinaTwelve200; 04-08-2018 at 02:14 PM.

  15. #15
    Member Anna Stouf's Avatar
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    The year was 1954. I was 10 years old. On Halloween that year, Mom sent me to school completely dressed as a girl. Panties, slip, and pretty dress. I loved it soooo much.

    Been doing it ever since.
    My favorite dress is a Dirndl.

  16. #16
    Member Heather Anne's Avatar
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    As a teenager in the early to Mid-1960s I was constantly getting into my sister's things. Unfortunately I was also getting caught by my parents. One time I wore her GoGo boots, busted the zipper and had to take my allowance and buy her a new pair.

  17. #17
    My BF and Style Guru Millisense's Avatar
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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!

  18. #18
    Member Megan b's Avatar
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    I was 12/13 when I tried on a pair of my moms pantyhose for the first time. I was hooked from that moment on. Shortly after the hose came panties, then girdles, slips, bras and finally a dress. No wig or makeup till years later. But now I can't really imagine not being a crossdresser, it's just part of me.

  19. #19
    Member StefaniLara's Avatar
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    Gosh, I can't remember that far back! I would have to say around 12 years old, right around puberty.
    stefanilara.wordpress.com
    A Girl in disguise

  20. #20
    formerly: aBoyNamedSue IamWren's Avatar
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    I have worn items intended for women, once or twice here and there, as far back as 30 years but it wasn’t but just three years ago at age 48 that I wore women’s clothing for the deliberate purpose of trying to look like a woman.

    I’ve learned a lot on how to to do that better and have even, with the help of members from this site who live in my area have found the nerve to go out while dressed.
    I am not a woman nor am I a man... I am an enby. Hi, I am Wren.

  21. #21
    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.

  22. #22
    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.

  23. #23
    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

  24. #24
    Casey
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    OMG. I do remember doing this too!!

    [SIZE=1]- - - Updated - - -[/SIZE]

    Quote Originally Posted by Taylor186 View Post
    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.
    OMG. I do remember doing this too!!

  25. #25
    Member wanda66's Avatar
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    In the beginning.......

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