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Thread: When did you first crossdress?

  1. #51
    Aspiring Member dana digs sweaters's Avatar
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    Kind of like this

    halloween.jpg

  2. #52
    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.

  3. #53
    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.

  4. #54
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    Love that.

  5. #55
    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.
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  6. #56
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    This thread repeats a very common topic. While it is always interesting to see how others first began to dress in female clothing the question I always have is rather different. I'm sure that many young boys experimented with trying on female clothing at some stage in their young lives. But how many found it thrilling and incorporated it into their lives from then on?
    A young women told me of how she used to dress her younger brother as a princess for her games. He would play along with it but he never became a cross dresser. I wonder why?
    What is the cause of the trigger that turns a single dressing occurrence into a life time need/

  7. #57
    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.

  8. #58
    Junior Member lynnmcarthur's Avatar
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    I was 4 or 5 and had thought about being a girl around that time. Going on 66 yrs of feminine thoughts

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

    And in reply to Consuelo, I was thrilled form the beginning

  9. #59
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    I started with tights and underwear when I was about 14. Progressed to skirts and dresses in my 20,s.

  10. #60
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    My dressing began years ago,probably 15-20 years ago,as I began experimenting secretly,wearing mothers clothes.I would wait for her to leave for work,and lock the house&close windows and blinds,and each morning I would spend mornings trying on her dresses,
    and skirts,and her soft,silky blouses&her dress slacks&regular shoes.Over time,I got bold&lifted a fresh pkg of beige pantyhose,put them on&added a short dress,or skirt and a blouse&began trying on her heels&learning to walk around the house in heels.As I became better balanced,I began trying on all of mothers good outfits,all of her pantsuits&I would dress in one of her expensive skirtsuits&sit at her makeup table&try on one of her wigs&spend mornings dressed.My favorite outfits were one of her mini skirts,a soft
    silky blouse&her double breasted blazer,a pair of off black pantyhose&heels
    "Love&Kisses"
    Michelle

  11. #61
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    I've always taken the position that donning a singular article of women's clothing does not make a cross dresser. Does a guy who dons female attire as a joke on Halloween make him a cross dresser? I think not. to me there has to be some feeling or motivation coming from the inner self to do it. A cousin forcing a young boy to wear girl clothing is not cross dressing.

    That being said the first time and subsequently I wore my mother's nylon full slips. I had zero desire to be a girl. It was nothing more than the feel of the fabric. Nylon was like no fabric I had in my boy clothing. First it was fondling the nylon as the slips dried in the hallway of our apartment. Finally, I had the desire to put one on to see how it felt on my body. The slips felt wonderful. I still had no desires to proceed further....until puberty....when hormones started to rage. Then came the panty, bra, slip, hosiery, and, the one dress I was able to fit into. Then came the confusion in sexual identity. What caused the compulsion to wear women's clothing? That was when I feel I became a cross dresser, a confused young teenager wearing his mother's clothes.

  12. #62
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    I thoroughly enjoyed wearing mothers clothes,we were the same size&height&I never worried about stretching anything,like a skirt,or a blouse& I would shower,so the scent of perfume would not be on me.I always ordered frilly undies&pantyhose online&had it
    delivered to a UPS mailbox,and soon all of my wardrobe was ordered online.I still have a key to mothers house,to keep an eye on animals when she travels,but I still enjoy dressing in her good wardrobe,especially her good skirtsuits
    "Love&Kisses"
    Michelle

  13. #63
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    I tried on a pink frilly dress when I was 15.

    It put a spell on me that still hasn't been lifted.

  14. #64
    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!!

  15. #65
    Member Jessica S's Avatar
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    I was helping my mom sorting socks and a pair of my mom's Knee-hi's were in the pile, I was around 4 or 5. Something clicked and I had to try them on. Then came pantyhose then panties and everything else

  16. #66
    Member Rhandi Spencer's Avatar
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    My sisters used to dress me in little girl clothes when I was very young, they thought it was just wonderful having a baby sister.
    I was 15 and house sitting for some friends and I would go into the daughters room and try her stuff on but it was all to small so I ventured into the moms room, tried on panties, bra's girdle and panty house. For whatever reason I never tried my mom or sisters clothes on. I tried my wofes bra and panties on once and determined then that I needed my own garments.

    Game over
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    Rhandi

  17. #67
    Aspiring Member Desiree2bababe's Avatar
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    I've been walking in heels since the age of five, started wearing sister's slips at age of 8, went full drag age 15. It's been a lifelong affair.

  18. #68
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    Xanten , Probably around day two or three when Mom dressed me in that pretty little White receiving Gown,
    when I came home from the Hospital, I was hooked for life

    Around age four I would play with Mom's heels & Hose and the rest is History.

    I've been in this program for 71yers now.

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  19. #69
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    I was 6 or 7, found one of my mother's half slips in a closet, and tried it on. Shortly after that, I added her panties.

    By age 10 or 11, I'd started wearing her bras and dresses as well.

    I like to think I was never caught, but that's likely wishful thinking.

    By age 13-14, I had started building my own wardrobe.

  20. #70
    Silver Member Rhonda Jean's Avatar
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    I was 5 or 6. My dad and brother were painting the house and my mom and sister went to the grocery store. I was alone inside the house and decided to play with my mom's makeup. When I heard them come home I hurriedly tried to take it off and found out it didn't come off that easily. My mother came in and called for me and I was in the bathroom with the door locked. I was petrified. She made me unlock the door and, of course, saw me with the smeared remnants of makeup all over my face. She said, "It doesn't come off very easy, does it!" She took it off and told me not to play with her makeup, that if I wanted to play with makeup to ask her. I don't remember ever asking.

    I had long hair even back then, and at about that same age I remember her rolling my hair for a family reunion dinner at a restaurant. I've been told that wasn't the first time, but that's the first (of many) I remember. Also at about that same age, maybe a little younger, I remember being out in the garage where the washer was and getting one of my sister's skirts out of the dirty clothes and putting it on and twirling around the garage. My dad opened the door to call me for dinner. Nothing was ever said about the skirt.

  21. #71
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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.

  22. #72
    Junior Member stephaniestilley's Avatar
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    I remember trying on one of my sister's dresses when I was 8 or 9, but the first time I fully cross dressed was when I was in 10th grade and I managed to get a hold of a dress, a bra, a pair of panties, and a wig and went for a walk around my neighborhood really late at night so no one would see me. It felt really interesting until a police officer drove by and stopped me and I got really scared. I made up some story that I was doing this as a dare and he just let me go home. I was so scared that my parents would find out that I immediately ran home and was shaking like a leaf for the rest of the night. I never talked to anyone about because it was a really terrifying experience. Until recently, that was the last time I cross dressed and now I wear dresses and skirts more than I wear men's clothing

  23. #73
    Member Ashley090's Avatar
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    Being dressed in costume of Forest Fairy by my mom for kids party counts as start? Then its about when I was 4. Dressed on my own was when I was 7. But it has been only two years since I ventured out to world.
    "Do not care what others think, do what you must" - Javik, ME3

  24. #74
    Member Amymonroe's Avatar
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    i'd say somewhere around age 13. it started with under wear and bathing suits and casually went on from there.

  25. #75
    Member Heather Anne's Avatar
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    The first time I was dressed completely from head to toe en femme was during a makeover with Phoebe Cross, near Atlanta. She gave me the phone number Sigma Epsilon Atlanta. My first meeting was on a Friday. Saturday I came back. Changed clothes applied makeup and went to Ruby Tuesday for lunch April 2004. The first time out in public completely dressed en femme. Prior to that was when I was a teenager always getting into my sister's things (mid 1960s) and getting caught by my parents.

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