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Thread: What's Your Earliest Crossdressing Memory?

  1. #26
    Aspiring Member Deanna B's Avatar
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    hi honey . oyes i was 3 or 4 i think . i got my mum sexy panties and put them on and love it so i hide them and wear them . then i wanted to be a girl .much better clothes and a lot more colour and softer. love deanna b xx

  2. #27
    Aspiring Member EllieOPKS's Avatar
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    Earliest I can remember was when I was about 4 or 5. My best friend was a girl 2 doors down from us. We would play together all the time. She invited me to tea parties with her dolls and we would role play as mom and dad. She suggested one day that she be the dad and I be the mom so we swapped clothes (except for undies). I can still remember how unusually good her leotards felt.

  3. #28
    sissy maid
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    When I was young, I would sneak into my parents friends bedrooms and look at the females lingerie. As I got older I began to steal a pair of panties here, a slip or a teddy there. My desire was always lingerie and panties, and still is. It started by my account by the time I was about 8. I also stole a french maid lingerie set from a friends mom in junior high. (blush) That was when I realized that the whole french maid thing was what turned my crank. It was not till I got my first computer and internet connection that I even knew any male was into the whole sissy maid thing.

    If nothing else your post has given me a chance to think about what a wild and crazy ride it has all been.

  4. #29
    Senior Member dawnmarrie1961's Avatar
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    Quote Originally Posted by alexs View Post
    I wonder how many of us can pinpoint a time we first crossdressed? Or a time we first wanted to?

    I can remember my mum, dad, and brother being out of the house--likely I was around 7 or 8--and I took one of mum's fake fur coats from her wardrobe and paraded down the hallway like a catwalk model as I looked at myself in the mirror.

    I don't think I had a clue at the time why I was doing what I was doing, though I do recall the thrill.

    Alex
    In the womb. I had was wearing my mother.
    CANCER IS A BITCH SO YOU HAVE TO BE MORE OF A BITCH TO BEAT IT.

  5. #30
    Gold Member NicoleScott's Avatar
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    My earliest memory of different desires began around age 4 or so. Looking at magazines and catalogs, my eyes were drawn to pretty women, especially their high heels and red lipstick, and to a lesser extent, their dresses, lingerie, and hair. In public, my eyes were always looking at high heels and lipstick. Around age 8-10, I started experimenting with lipstick behind a locked bathroom door, and high heels when I was alone. I have an older sister who wore very high heels, and her clothes fit me throughout several teen years. It wasn't until my late teens and into my twenties that I began dressing up and applying makeup for a complete transformation. It took years of trial and error and accumulation of makeup, clothes, wigs, and shoes before getting pretty good at it. All in private, the advantage of which is NO RULES, able to go for the look I love - overdone.

  6. #31
    Senior Member joannemarie barker's Avatar
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    I remember my first time being my sisters swim suit at 11 but the memory that really stays In my mind was the day I first went to school wearing panties.I chose the day carefully,making sure I wasn't doing pe or anything too physical and picked a pair of satin peach panties from my sisters drawer.I remember having mixed emotions that day.I felt so good wearing something all of the girls in my class had on but looking at the boys and thinking I'll never be the same as you.

  7. #32
    Mina minalost's Avatar
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    Sixth grade I think... sneaking out of bed and getting one of my moms bras out of the laundry basket. I put it on, stuffed it with socks, and went back to bed. Had a wonderful nights sleep...
    Mina Lost aka Lynda

  8. #33
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    I remember I was around 4 wearing my mothers panties and putting a towel around my waist making believe it was a dress.

  9. #34
    In the closet - for now. Shadeauxmarie's Avatar
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    I think I was 6 when I tried on a pair of my mother's stockings from the trash. I loved the feel, even though they were ripped, and I can remember them smelling like my mother's perfume. They were too big, but i was completely hooked. I have loved stockings ever since. The old fitted style like Hanes with the great sheerness and dark RHTs.
    May you live long and prosper.
    Infinite diversity in infinite combinations.
    "Smiling makes my face ache." F. N. Furter

  10. #35
    Carole carhill2mn's Avatar
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    I was either 7 or 8 and I put on one of my mother's silk blouses. It fit me like a dress and I was hooked!
    Hugs, Carole

  11. #36
    Donna June Donna June's Avatar
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    I was about 7 and desperately wanted to try on one of my older sisters party dresses. When I did it was heaven. My 2nd time was a full slip. ooh la la, been hooked ever since.

  12. #37
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    I can't remember what was first. I have clear images of me wearing my mother's underwear at a very early age.
    But one thing that most likely was my first try was a pillow case that I wore like a strapless dress. Although, technically, it wasn't crossdressing...

  13. #38
    Complex Lolita...
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    Quote Originally Posted by alexs
    What's Your Earliest Crossdressing Memory?
    [SIZE="2"]When I was 3 or 4 I put on my aunt’s lipstick and makeup – does that constitute crossdressing? [/SIZE]

  14. #39
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    I was somewhere around 6-8 when my family was visiting another fam$ily with girls around my age. I snuck aroumnd and found some blue panties. I wore them under my clothes.Mom then insisted I get undressed for a shower and I was caught! Undettered, I wore some yellow ones the next day and well, we all knopw the rest of the story!

  15. #40
    Addicted To Lipstick donnatracey's Avatar
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    Didn't realize I was such a "late bloomer"! I first tried on 1 of my mom's dresses when I was in my early teens.....

  16. #41
    Discovering the Gurl Xandra's Avatar
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    Quote Originally Posted by Frédérique View Post
    [SIZE="2"]When I was 3 or 4 I put on my aunt’s lipstick and makeup – does that constitute crossdressing? [/SIZE]
    Yes, I would count it

  17. #42
    Discovering the Gurl Xandra's Avatar
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    It's great to read of everyone's early memories. It's interesting how we can recall not just the moment but the feelings associated with that moment.

  18. #43
    Addicted To Lipstick donnatracey's Avatar
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    Like the feelings of fear/helplessness I had when the zipper got stuck on my mom's dress and she was due home soon........

  19. #44
    Member stellatoo's Avatar
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    Hi, I was 11ish and remember being "aroused" in my sisters school knickers (bottle green colour!!! Ugh) After that there was no stopping me! Even when my stash was found (again & again)
    "Slipping into stockings, stepping into shoes"
    The shortness of life prevents us from entertaining far-off hopes. From Horace’s Odes, Book 1,4

  20. #45
    Member Susan_Xdress's Avatar
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    My earliest memories of wearing anything female would be around 7 or 8; the first items were my mother’s slips. Not sure if that qualifies as a conscious ‘crossdressing’ experience or simple curiousity. I know they always felt wonderful.

    I was 11, it was very wet day and our parents were going to be gone until very late that evening. As they couldn’t play outside, my older sister 14 and her best friend 15, decided to have fun with me.

    Their intent was more to be mean and tease, than for any pleasure for me. Ah little did they know that from the first minute when they put me in my sister’s skirts and panties, I was totally hooked.

    I never showed any pleasure. I acted upset and the more upset they thought I was, the more they dressed me. The ‘made me’ wear her school skirts, casual skirts, dresses, panties, bras, and slips and they fiddled around fixing my hair, putting some make-up on me and having me walk around the house. OMG ! To walk around openly in the house feeling those skirts and dresses around my legs ! I clearly remember making myself cry at times so they would keep on dressing me.

    They dressed me up a few times after that, but that was the first time I wore female clothing and knew that I loved feeling girly.

  21. #46
    Gold Member NicoleScott's Avatar
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    Quote Originally Posted by Frédérique View Post
    [SIZE="2"]When I was 3 or 4 I put on my aunt’s lipstick and makeup – does that constitute crossdressing? [/SIZE]
    Let's pose that question to unaccepting wives. On second thought, let's not. Let's get some psychology academic with lots of letters after his/her name to declare it's not.

  22. #47
    Member NikiMichelle's Avatar
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    I was 4 or 5 when I started wearing my sister leotards (leggings)...all iI remember is how neat they felt...I have no idea what motivated me to try them on the first time though???

  23. #48
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    I was 10 years old, if memory serves. My friend dressed me up as a girl because she thought I'd look cute as one. It was a very different feeling in girls clothes, then, my regular boys clothes. My hair was longer at the time, so no wig, but I wore a skirt, training bra and some girly top.

  24. #49
    Member Dealight's Avatar
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    Had to think about this one....still not positive...but I am SURE pantyhose played a role ! I can remember being fascinated with the feel of nylon...and trying on pantyhose on various occasions from various sources.....later on in my late teens it became an obsession which stayed with me...I still feel more relaxed and comfortable wearing a pair of pantyhose. Hmmmm...think I'll go put some on now.........

  25. #50
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    Also 4 - 5, i remember sitting on the stoop in front of my neighbors house with the neighbor girl, she was painting her nails, I asked her if she could do mine, she did. when she was done, wanting to be like mum, I went running into the house to show my mum that i was just like her, she promptly scrubbed it off.

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