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Thread: At What Age Did You Start To Crossdress? / What age did you start cross dressing? Why

  1. #76
    Member Annemarie's Avatar
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    12 or 13 I think.When dressing was a midnight or 5 am activity.

  2. #77
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    I guess it was about 6-7 for me.
    Although I do remember playing at "Star Treck" with my best mate, and insisting that we landed on a planet where the aliens turned us into girls! He always said "yeah, they do that to you" and I have to save you. Would you believe it? I'm still intouch with him after nearly 40 years. I haven't the guts to ask if he remembers that. But then that was as far as it went. I didn't even get to dress up. I just had to pretend.

    Ha' if only I knew then what I know now.......

  3. #78
    Patchwork Material sparks's Avatar
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    Somewhere around age four and still counting. I don't think I ever really stopped dressing after that.
    [SIGPIC][/SIGPIC]

    [SIZE="3"]And I was thinkin' how the world shoulda cried
    On the day Jack Kirby died
    [/SIZE]

  4. #79
    Junior Member Jeanine's Avatar
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    I have Glaucomas and my breasts started to develop at 11. All the other kids, including my 3 older sisters, and a lot of adults made fum of me and said I needed a bra.

    I started out by "trying on" my sisters' bras when I was 13 ...My boobs completely filled the cups of my oldest sister Patti's B underwire bra like it was custom made for me ... After finding out how good the bras felt against my skin, it wasn't long before I graduated into panties, stockings high heel shoes, dresses, slips, shirts, tops, bikini bathing suits, wigs and a little makeup as well.

    All 3 of my sisters caught me wearing their clothes several time and always snitched to my Mom. I think Mom secretly wished I had been born a girl as much as I did but she always yelled and screamed at me and ordered me to leave my sister's clothing alone.

    It wasn't until Mom came home unexpectedly and caught me wearing a thong, fishnet stockings, a micro-mini skirt, a tune top, 4 inch spiked heels,
    a wig and full makeup that she decided to take me to a Gender Councilor

    After several months of private sessions, the councilor asked Mom and all of my sisters to attend the sessions as well. She was a forward thinking woman and she explained that it would be best for everyone if I was allowed to dress as a female as often as I wanted to at home only because the general public in the 1950s frowned upon crossdressing.

    After that, I was allowed to dress as as girl, at home, as often as I wanted to ... Me and Mom, and all of my sisters borrowed and wore each other's clothes all the tim.e

    Mom and and the girls always took me along on shopping trips to the malls
    on so I woul have a full wardrobe of feminine clothes, makeup and shoes as well.

    Hugs-N-Kisses,
    Jeanine

  5. #80
    Silver Member LilSissyStevie's Avatar
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    My first experience with crossdressing was when I was about 5 years old. We lived outside of town and I only had my sisters to play with. The only other kids living near us were girls, also. My sisters and their friends would have me wear their dresses so that I could play dolls with them. It was all very innocent, but I really liked being one of the girls.

    My grandmother watched us kids while our parents worked. She would buy dresses and sun suits for my sisters but I would get nothing. “Boys don't need a lot of clothes,” she said. It was obvious she didn't like boys much. That made me want to be a girl even more. I played “dress-up” with my sisters until I was 11 when our family split up and I moved to California to live with my dad.

    When I was 6 or 7 my mom enrolled me in ballet classes because my sisters were taking lessons and she didn't want me just hanging around while the girls were dancing. I had to wear my tights and leotard to school under my clothes because class was right after school. It wasn't exactly crossdressing, since boys and girls wore the same practice outfit, but it was still considered very girlie. Boys just didn't take ballet lessons in the early 60's. So, I was the only boy in the class. I learned real quick to hide the tights and leotard real well because when the other kids found out I got teased mercilessly. Those are my earliest memories.

  6. #81
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    ="Comi[COLOR="RoyalBlue"][I]As a young boy I use to crawl under the dining room table at my grandmothers house and rub the legs that had hose on.Sounds weird but I knew then that I loved nylons.So when I grew a little I would sneek into my grandmas room and take a pair of her stockings (the ones with the lines on the back ) and put them on.So Im guessing 10 or so. Take care Girls... Gerri Paul

  7. #82
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    I started when I was 12 :-)

  8. #83
    Dreaming of Satin & Lace Jasmina Lace's Avatar
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    It was sometime during those years just before puberty when a young boy starts to pay attention to girls, but not quite in a post-puberty sexual way. I remember during those years spending vacations at my grandmother’s house and she had this bedroom with all her many shoes, clothes, and perfumes (she loved to collect perfumes). It was where I slept and for some reason, unconscious at the time, that room made me feel so warm and secure. I guess at some point I decided to see what it was like to play dress up like girls did and got into some of her things. From that point forward I have always dreamed about having a very feminine bedroom to spend time and dress up in. Warm memories, thanks!!

  9. #84
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    i started about age ten,my sister and another was playing in an old car with boxes of clothes in the back seat when we all started trying them on and someone threw a full ship at me and dared me to try it on, it felt so silky and coool against my skin and been hooked ever since off and on for over 30 years

  10. #85
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    I don't remember myself. By that I mean, I don't remember much of my childhood through til the past few years. I accept that though, and really it's probably for my own good. My earliest glimpses, however, are probably in the roughly 10 year old time-frame. I remember trying shoes first (something which I absolutely love to this day!). I was an only child, so I had to make do with what I could find, but I do know it progressed from there. I had my parents buy me Keds before I could (dunno how I pulled that off) and then my own clothes when I had a job. By college it was full on I suppose, and between the start and now it's come and gone due to my own suppressings... but I can't see as how I can ignore me any longer.

  11. #86
    New Member miss laureux's Avatar
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    .It started with puberty. I always loved those foreign erotic soft-core porn movies on Showtime. I found myself always getting turned on by garterbelts, stockings, etc... Around early teens, I saw the film, SID & NANCY.... where there was a dominatrix and a man slave chained to the ceiling.

    I never put 2 and 2 together until I started stealing clothes from the women I knew. (early teenage years) At first, I was ashamed and couldn't believe it. In privacy, I began to dress up more and more.

    With the women I dated, I made them wear lingerie and corsets, etc...

    Then... the late 90's... the Internet truly made my fetish bloom. I discovered Forced Feminization, french maids, sissy maids, and ebay!!! This way, I could purchase all the kinky lingerie I wanted in secret!!! With the internet, I found out what I liked and what I didn't like....

  12. #87
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    A bit later for me, mid 30's. My facination with high heels, stockings, and panties led me to try them for myself.

    Miss Laureux, nice photo. Is it you?

  13. #88
    Junior Member Brenda_fish's Avatar
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    Late too

    44 here. I have always been infatuated with women - figured most guys are. In my late 30s I started to pay more attention to what they wore and what particular things I liked - heels are a big one. I then became "aware" that I wanted to know how it felt. I'd done nothing yet but dropped the bomb on my wife of 10 years. She was shocked but fairly understanding. Still in the closet but love when I get to be pretty!

    Brenda

  14. #89
    Member Michelle_NY's Avatar
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    I first started about 5 or 6 yrs old. I was trying on my Mother'sstockings, girdle and slip. It grew from there.

  15. #90
    New Member cdsissy12's Avatar
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    i started crossdressing when i was 13.first i was wearing my sister's pantyhose.then my girlfriend's skirt, pantyhose,high heel,stocking.when im 16 i started make-up.

  16. #91
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    Well, since I can remeeber. About 3or 4 . Was a pair of tights and the rest was history. Ever since then I have been going to town. I love all girls stuff. Just can't accept fully yet. oh well

  17. #92
    Content and Happy
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    I've been who I am since around 5. I was made fun of because I sat to pee. I didn't know any term for how I felt, I just knew it was ok for me. I've always dressed more female than male and the cloths I wear at home I wear in the world. Since I was raised without labels, they don't mean that anything to me now.

    Lanore

  18. #93
    mom's "daughter" KarenNY's Avatar
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    I started around 7 or 8, maybe even earlier, in my mother's "overflow" closet in the guest room... my mother and I were on our own, the sperm donor having split when I was about 5. I think I looked up to my mother and wanted to be like her when I grew up, never mind that I was a boy... She had a lot of pretty clothes (okay, nice for the late '70s anyway) and always dressed femininely -- she worked as the office manager for a financial planner and thus had a lot of nice clothes. When I was about 9 or 10 and in fourth grade, I started being a "latchkey" kid, arriving home from school before my mother got home from work... so that gave me even more time to "explore" my mother's closets, as I checked out her bedroom closet and dresser drawers. By the time I was 11, I was not only trying on her clothes, but her lingerie, pantyhose and high heels. In those years, I also stayed at a familiy friend's house when my mother was working, watched by dear Mrs. Holmes. I even explored hers and her daughter Nancy's closets when I had the chance.

    Mother discovered my interest when I was 12, coming home early one day and almost catching me red-handed in her pink ruffled blouse and light gray skirt suit and heels... I was fast enough to change, but she found her clothes on the floor of her closet, confronted me about them, and as I cried about it, she encouraged me to talk about my dressing interest... and I discovered that she was actually okay with it -- concerned, of course, but not angry and only upset that I was sneaking around behind her back. So that all led to my mother's wonderful acceptance and support of my dressing, and her buying me girls clothes, makeup and everything else. Hey, it was just the two of us, who the heck was I hurting? Turned out also that Mrs. Holmes knew about my "explorations" as well, and she was also one of my biggest supporters -- she absolutely doted on me as Karen, and I had not one but two places I could go and dress up and be a girl, my house and Mrs. Holmes'. I even inherited Nancy's hand-me-downs -- all those delicious ruffled blouses and Gunne Sax dresses from the early '80s!

    So that's part of my life's story.
    "Behind every great man is a woman rolling her eyes..."

  19. #94
    Member Karen Johnson's Avatar
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    The first time I recall was when I was 5 or 6. My big sisters white cotton panties and sun dress. I can still remember how nice it felt to put it on, how natural it felt. Later in my teens I would sneak her or my mom's stuff when I got the chance, then later on my first wife's.
    When I was in my late forties I came out to my second wife and she bought me a pink nightie and then put it on me so I wouldn't feel so awkward about dressing in front of her. That was the first girlie thing that belonged to me.

  20. #95
    Member CD Tammy's Avatar
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    I was SIX. I remember it clearly. My step-mother had far too many clothes for her closets so she used mine to hold the extra. One day she changed quickly and left a pair of pantyhose on the closet floor. I loved the way the felt and wore them under my clothing for weeks.

    How could they stretch to fit her long sexy legs and still fit me too? Size "B" I still remember.

  21. #96
    Senior Member Sarah V's Avatar
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    At What Age Did You Start To Crossdress

    I started at about the age of 9 -10 when I noticed a pair of my mom's stockings (or were they pantyhose?--that was a long,long time ago ) hanging over one of the towel bars in the bathroom when I was taking a bath one day. That was the start of it all right! I have never really stopped since, except while I was in college, but even then I certainly kept up my interest in things.

    Like most I imagine, my dressing progressed from the very simple to the full dressing I do at home and when I go out today. I too started out trying on and wearing my sisters' things. I could never wear my mothers things as she was much larger than I. As my sister got older (we have always been about the same size) when she would throw stuff out or get ready to donate things she did not want anymore, well, somehow I would intercept them and make them my own. It was not until I was out of college and on my own that I began to buy things for me. Used to go to a lot of second hand and charity shops, and found some wonderful things (many of which I still have).....and on the 'el cheap too! Today I buy almost anything I want mostly new from regular stores. I know my sizes pretty well and that makes things easier. I have also incorporated a lot of ladies wear appropriate for some of the activities I lake to participate in (exercise, dance, ectc.)

    The only thing that I didn't get into till much later on in life was the use of make-up and using a wig, but even that has been over 12 years now.

    LIke one of the others ladies posting has said, this is only a small part of the story of the development of Sarah over the last 30+ years. .


    Sarah[SIZE="3"][/SIZE]

    "Sport is for men.......But Ballet is for women" ---- George Balenchine

  22. #97
    Member Rebecca C's Avatar
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    Smile

    i believe i started around 7 years old , wow thats 30 years ago . crossdressing has become a very big part of my life and it just gets better and better as time goes on .

  23. #98
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    I have been dressing up in females clothing ever since I was a young boy and was stealing panties and various other clothes from my older sisters room and then going back to my room and trying the clothes on and I realized that I enjoyed wearing female clothes better because they felt better and also I had a type of sexual arousal from the clothes as well. So from like 7 or 8 til now.

  24. #99
    Super Moderator Raychel's Avatar
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    It was right around the age of puberty for me. I guess somewhere around 10
    my sister's reply when I told her how I prefer to dress

    "Everyone has there thing, all that matters is that you are happy, love what you do and who you do it with"

  25. #100
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    I was in 13 or 14 when I first started experimenting with make-up. I would put it on every chance I got (I only got caught once.....). Soon after that I raided my mom's boxes of old clothes she had stored in the basement and I was on my way. It is something I have done ever since. I don't dress often now, just a few times a year.

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