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Thread: When did you first crossdress?

  1. #26
    Junior Member Eddie's Avatar
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    I was 7 years old. I was always fascinated with nylons and girdles. My mom would have her friends over for coffee during the day and they would sit around the table,smoking cigarettes and gossiping, often wearing nylons and I wanted to be just like them. One day when she was out, I snuck into her underwear drawer and put on her girdle and nylons. It was an incredibly exciting feeling. I loved the tight feeling. It was sexually stimulating, and I didn't even know what sexual stimulation was yet.

  2. #27
    Jessica Gibson Sylvermane's Avatar
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    I tried on a pair of pantyhose when I was 7 or 8 years old. That electric feeling that surged through me is still with me and I remember it fondly. The first time I really went all out was when I was 10 or 11 years old. I had a day to myself, mom and brother were gone all day. I dressed up in a nice business style black skirt that was 2-3 inches below the knee. A blue sleeveless blouse... of course the bra and panties as well as off black pantyhose, girdle. And the cutest pair of velvet 3 inch heels. I spent almost my entire day dressed in that and was in heaven all day. That was probably the single best day of my life in regards to cding and I regret not having more days like that... even though I did have the opportunity.
    How often do you daydream about finding a genie's lamp...

  3. #28
    Not an Active Member Alisa's Avatar
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    Here is an earlier post on this subject.

    http://www.crossdressers.com/forums/...t=#post2409283

  4. #29
    Junior Member kellylynn_31's Avatar
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    9 or 10 years old, moms panties

  5. #30
    Butterfly Princess Andinera's Avatar
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    I was about 6. I was about to hop in the shower when, surprise, my sisters panties are laying on the bathroom floor. I got them above my knees when, no knock or anything, my sister comes in the bathroom and sees me. I don't remember if I pulled them up after she left but needless to say I denied it when she brought it up at dinner later that night.

  6. #31
    Aspiring Member TeresaL's Avatar
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    1950. I was about three or four, and got caught wearing mom's nylons. She really put the shame and guilt trip on me. LOL

  7. #32
    Aspiring Member Georgina's Avatar
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    I must have been about five or six, I can't remember exactly. I remember discovering my mother's nylon slip and for some reason wearing it. I am so glad I did.

  8. #33
    member stacycoral's Avatar
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    I would have to say it was my sister junior girl scout dress, it was short for me, but felt great to be a girl, around 12, hugs.
    [SIZE="3"][/SIZE][SIZE="3"]Stacy Lynn Coral[/SIZE]

  9. #34
    Member Luna Nyx's Avatar
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    my own accord I didnt get into it hardcore till about a year ago. My mom dressed me up when i was a baby or so im told.

  10. #35
    Aspiring Member outhiking's Avatar
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    I was 12 and tried on a pair of knee highs while my mom was sewing up my jeans. Next came the bra, but it was when I discovered and wore her babydoll with sissy panties that I was truly hooked.

  11. #36
    Cat's Eye Siren ArleneRaquel's Avatar
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    Between the ages of 6-8, that was ages ago. The urge has waned, at times, but since 2004 it's been also always 24/7. There is no heading back for this old bag.
    Fulfilling a Lifetime Dream of Living as a Woman in My Adult Years. Ten Years Living 24/7 as a Mature Lady

    My Love of Cat's Eye Frames, Bangles, Red Lipstick, Nails, & Cheeks, Comes From My Mother - An Irish Beauty

    I'm Always Rainbow Proud

  12. #37
    Member MeganHenry's Avatar
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    Between the ages of 8-10...

  13. #38
    Aspiring Member Teddie's Avatar
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    I think it was around 7 or 8, and what started it was my mom's Platex rubber girdle (open bottom), plus the nylons needed to hold it down. I'd love to have one of those girdles today.
    Hugs,

    Teddie

  14. #39
    Super Moderator Raychel's Avatar
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    For me the underdressing started back when I wss just a boy. Probably sometime in the late 60's
    and the full dressing started somewhere around 2005-2006
    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"

  15. #40
    Aspiring Member
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    When I was six years old. I put on my mothers clothing. It began there and never stopped, just a pause now and then. 46 years and counting.

  16. #41
    Junior Member JuLo's Avatar
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    I think that I was 11 or 12. My mom did custom sewing & alterations. She was sewing bridesmaid dresses for a wedding. She needed to check a hem on a dress and I was just the right height! Screamed & hollered on the outside against it, but loved every moment of it on the inside! I was hooked for ever!

  17. #42
    Aspiring Member Ms. Laura's Avatar
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    In my room at my Grandmother's was a closet full of her stuff. The earliest recollection I had was for some reason, I wanted to try on this pair of funky, high heel, beaded sandals that fit me at the time. I was maybe 9 or so. I remember how it arched my foot and looked like the ladies in the catalogs etc. From there, it just built on top of that until voila, you see what you get in the avatar.
    "I want you all to call me Loretta." - The Life of Brian

  18. #43
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    I was probably about five years old. I was in the bedroom of my "youngest" sister and my other sisters decided that they would dress me in a corset belonging to my aunt, who was visiting at the time. The memory is so electrically clear to me; the feel of the corset, the soft material on the panels and the sunlight shimmering off the silvery satin. From that time on I dressed as much as I could. The sister, who was just a few years older than me, used to put makeup on me and make me sit outside by the street. I had three sisters, all older. What is interesting is not just the particulars of that first time but the way in which it shaped my sexuality. Dressing and underdressing in feminine clothing became more and more frequent. I also found that I enjoyed being a "bottom" sexually. I don't regret that day and neither do I blame my sisters for doing what they did. I believed that they unlocked something inside me and that set a course in my life.
    I have friends whose son began dressing and using his mother's makeup at an early age. His mother just let him do it and never admonished him. He would borrow his mothers clothes and use her makeup quite openly and often in her presence. We talked about it a little and I told her that her tolerant treatment of her son was admirable. Don't we all wish that we had had mothers like that.

  19. #44
    Member Dena's Avatar
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    When I was around 7, my mom had me wear a pair of my sister's tights when my long johns were in the wash. I was going ice skating with my sister, I made a fuss, but found that I enjoyed wearing them!

  20. #45
    New Member Ninotchka's Avatar
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    My mother wanted a girl. And after her third son was born, she made me her little girl for a while. ( I was @2).
    My earliest memory is being dolled up in a yellow satin dress and having a ball. Later she stopped dressing me, but I had the taste for it by then, and would sneak her slip into bed with me like a security blanket.
    I was in the closet until I married my accepting wife. The next 38 years were peaceful private dressing with a loving partner who dressed with style.

  21. #46
    Silver Member Jilmac's Avatar
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    When I was the ripe old age of seven, I took a dare from an older male cousin to wear panties and a dress. I was hooked from that time on. I am now a 60 plus senior citizen with a full feminine wardrobe, wigs, and accessories. If my cousin was still of this earth I would thank him for the dare because it helped me discover who I truly am.
    Luv and Jill


    Straight, into Fantasy Land

  22. #47
    Keep Looking Up ...... Jolene's Avatar
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    I was maybe around 11 or 12 years of age and was about the same size as my older sister. Went into her room one day and some of her school clothes were laying there. After working up my nerve I went all the way.. bra, undies, pantyhose, and her skirt and blouse. It all fit me perfectly.
    In my mind I was ready for school, but oh well, maybe in another life .....

  23. #48
    New Member VikkiDave's Avatar
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    After many years looking and imagining it was me in those clothes, I snuck into my parents bedroom, tried on a pair of mums tan tights and slipped on a pair of 2 inch heels which felt so right. I was 10 at the time.
    Last edited by VikkiDave; 01-09-2013 at 02:55 AM.
    Every morning we wake up, healthy or not, given the opportunity to remake ourselves. We do not have to let the person we were yesterday define who we are today. The promise of each new dawn can be squandered by repeating patterns and habits that have always held us back, or we can decide that today we will finally treat ourselves with kindness. -Wheelchair Kamakaze

  24. #49
    Platinum Member Beverley Sims's Avatar
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    About 5 I played mothers and fathers when staying over with relatives.
    I was the baby dressed in a frilly pinafore dress with puffy sleeves.
    I wore frilly panties over my nappy and a dummy to finish it off.
    That night at the dinner table the high chair was retrieved from the garage and I was sat in it.
    I spent that night in a cot.
    I can't say I did not enjoy it. I played the baby a few more times and then grew up to be an aunt with bra and high heels.
    Work on your elegance,
    and beauty will follow.

  25. #50
    Gold Member Diane Smith's Avatar
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    My first thoughts about dressing are among my very oldest memories, at 2-1/2 or 3 years old. By that time, I had figured out that men and women dressed differently, that my mom and grandmother were very attractive when they dressed to go out, and that I wanted to look like them. But at that age, I had neither the clarity of mind nor the physical ability to do anything about it in practice. What gratification I got came from my mom occasionally putting lipstick, nail polish or jewelry on me, which both of us enjoyed for our own reasons, I think. My first memories of actually trying on women's clothes and shoes on my own start at around 5 years, and continued more or less without a break (although mostly in private) after that. As I've mentioned in another thread, at age 40 I had a kind of epiphany that resulted in an urge to get out and about and take it to the next level, so I have been much more adventurous and social in my activities these last 15 years or so.

    - Diane

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