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Thread: What made you crossdress for the first time?

  1. #1
    Junior Member Dani Alana Taylor's Avatar
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    What made you crossdress for the first time?

    I know this has probably been asked before but I am to lazy to go looking through the threads lol. I bet a lot of people are probably the same as me when I say i don't know why but I'm wondering if for anyone there were any specific reasons? Just asking!
    Taylor Swift rocks my world! What I would do for just for one date with her....

  2. #2
    The Journey Begins AmberDay's Avatar
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    It just seemed natural to slip on my sister's satin gown when I was five years old..... thought wearing satin was normal. My sub-conscience?
    “But you can only lie about who you are for so long without going crazy.”
    ― Ellen Wittlinger,


    "we could mix all three, the two gendered and the one non-gendered, "she", "he", and "it", to make "shi...". No, nevermind, that won't work either... "
    Alimarx SDMB 2004

  3. #3
    Carla Heracane Missy's Avatar
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    roll playing games at age five with next door neighbor boy I was nurse he was hurt and I had my sisters panties and bra
    I kissed places where he said it hurt and so it started for my acting and wearing girl cloths and pleasing boys lol
    WHEN IN STRESS WEAR A DRESS
    BE HAPPY WITH YOURSELF IT ALL YOU GOT

  4. #4
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    I had 4 sisters I think I was just curiouse.... And they loved to dress me up,i was a human barbie lol

  5. #5
    Silver Member Mollyanne's Avatar
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    curious, VERY CURIOUS!!!!! From the first moment that I wore stockings, a garterbelt and panties I was hooked!!!!! Haven't stopped since then, and have become much more comfortable dressing, in fact I was helped by my mom.

    Mollyanne
    "To thine own self be true"

  6. #6
    Member annecwesley's Avatar
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    I admired the way girls looked in the 6th and 7th grades, maybe even before that. I think though it was my music teacher in the seventh grade that finally made me want to see if I could look like a girl - she was real pretty and I wanted to look like her. So one day when I ws home sick from school, on when the stockings and slip borrowed from my mom... and I was hooked.

  7. #7
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    I had wanted to for at least a few years, then when I was around 6 or 7 I was able to sneak one of my mom's dresses on

  8. #8
    Junior Member JillyNylonz's Avatar
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    Purple: that was an absolutely lovely story! Entertaining as well as heart warming. Thank you so much for posting it !
    I did not have such a poetic introduction to the joys of dressing enfemme. I just took notice of my mother and all her friends that came to our house, wearing smooth shiny nylon stockings with very pretty heels. My curiosity got the best of me when I spied some laddered hose in my mothers waste basket. Before long I had some thirty stockings, all Hanes 415's, many only slightly snagged, stashed away to wear when Mom went on an errand, and I was home from school sick! I had many pleasing hours dressed in heels, hose and a garter belt walking around on an Oak floor, hearing both the sounds of those sexy heels, and the swish and zip of her(my) stockings as I walked ! I was at home, and sick a lot, after developing my newfound interest in crossdressing ! LOL !

  9. #9
    Shoe addict Talldrinkofwater's Avatar
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    I guess what opened this world for me was the first time i wore a dress. I was about four and at daycare playing dressup/house with the girls and a couple of the boys. The woman who ran the daycare had a bunch of old satiny gowns, slips, costume jewelry, and dresses she put out for the kids. I put on one along with a raggetty wig(i think i was supposed to be the crazy aunt or something) i loved the way the material fell so softly around meand and I guess that's when i was hooked.
    The meaning of life is to win the human race, or maybe, it's just finding the perfect shoes.

  10. #10
    Trouble.. Yep thats me Beth Mays's Avatar
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    At age 9 Mom would dress me up.... still have a couple pictures stash away someplace.
    Maximus Decimus Meridius (Gladiator):
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    You can fine me here on Facebook!

  11. #11
    Aspiring Member ronda's Avatar
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    i don't know i did not need a reason at 3 years old panties night gown and heels mom said he will grow out of that and siad i don't think so
    hugs
    Ronda

  12. #12
    Senior Member Fallen Angel's Avatar
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    I beeing a 70's baby all the clothes at that time were unisex and i guess the rest is history

  13. #13
    CD inori's Avatar
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    Because I want to feel pretty and cute :P And also I was always jealous when I saw a good looking GG wearing something that I was never gonna be able to wear.

  14. #14
    Member Regan's Avatar
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    I just remember always being fascinated in my mom's pantyhose and bras so when I had the opportunity go be alone I tried them on and have lived the feeling ever sense. This is also when I really started fantasizing about being a girl and always felt do comfortable with it. Unfortunately had to stuff those feelings for 40 years.

    Regan

  15. #15
    Gold Member ~Joanne~'s Avatar
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    I believe being a teen in the 80's drove me to where I am today. The women always wore pantyhose with almost everything and I loved the look. still do At one point I had to know what they felt like on, then came the heels, then it is where it is today. Spent a lot of years denying the whole thing but within the last couple I have come to terms. Pantyhose are what still brings it all together for me
    Flip Flops were made for Beaches & Bath Houses, We have neither in 2017. Lose the flip flops!

  16. #16
    Junior Member LeeBe's Avatar
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    I really don't remember when my first thoughts of CDing were, but I do remember that I was always wondering what it would be like to wear girls clothes. I would see girls wearing some neat looking outfits in school and just be so curious as to what it would be like to wear that.... it must feel so different from what I had on (you know regular guy clothes). I followed that same line of thinking when I would see fancy ball gowns in the movies.... I thought it was strange none of my buddies never shared my thoughts about girls/women's clothes, so I kept those thoughts pretty close to myself. Then one day I just came to the conclusion that all these thoughts about wearing women's clothes was just plain stupid and I had enough of that, so no more, done finished with that, period! I guess you can tell that really worked out well! LOL Anyway, from there it has just been a series a little steps, a few more items, just a little here and there and so on. I guess it always has been and always will be a large part of who I am.

  17. #17
    Junior Member NitaCD's Avatar
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    The first time I crossdressed I was 6years old. I was in the hospital for a tonsillectomy and had to wear one of those flimsy hospital gowns with no under pants. I complained enough to my mother about it until the nurse finally found a pair of pretty girls panties with blue flowers for me to wear. And as they say "the rest is history". I have been crossdressing in some form or another sense that day and love every minute of it.

  18. #18
    Miss Conception Karren H's Avatar
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    Don't know why except possible my mother used to remind me I was supposed to have been a girl a lot growing up... But one evening when I was 7. My parents were out on the town and we had a baby sitter for me and my younger brother..... they were both in the living room watching TV and I went off and explored my mothers walk in closet. I tried on girdles and bras and ruffled panties and a baby doll nightie.... Nylons.. High heels... After that I was hooked and would sneak into her closet when ever they were out...
    Current Obsession - Breasts and Lingerie!

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  19. #19
    Gold Member Marleena's Avatar
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    I don't know why either. I had an older sister that just got her first party dress with nylons, girdle etc. I found it in her room and had to put it on. Of course I got caught in it. My sister made my life miserable about it with her teasing. I had no idea what I did wrong.

  20. #20
    Adventuress Kate Simmons's Avatar
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    Nothing made me really. It just seemed like the thing to do at the time.
    Second star to the right and straight on till morning

  21. #21
    The Art of Heels Kristyn Hill's Avatar
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    My experience is real similar to Karens from the start. I was wearing my moms patent go-go boots in '73-'74 era when I was 3. From 3 on I snuck into her closet wearing her heels any chance I could. I did this until I didn't fit into her size 7 1/2" foot anymore. At 18, I bought my first 2 pair of heels at Payless then a 3rd.....purged later. Bought more....purged. Now my wife is completely GREAT with it and we were the same size so no more purging.
    I am an Artist working in all Mediums including Sexy

  22. #22
    Senior Member Jacqueline Winona's Avatar
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    Just the thoguht of Chrissie Evert in a tennis skirt got me interested, then my mother started wearing pantyhose for a new job and I just had to try the hose on- simply fascinated me at the time.

  23. #23
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    very common question, but there are always new people here. for me, the desire was innate. I recall thinking about women's clothing in some of my very earliest recollections - even dreaming about them. And as I preschooler first tried on one of my sister's slips.

  24. #24
    Member HannahF6's Avatar
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    I remember my first time in a dress very clearly. My mother used to make dresses for weddings. She'd typically have a couple of wedding dresses and many bridesmaid dresses in the house at any one time. When I was a young teen she'd use me to model them. I loved the feeling of being officially "pretty".

    I do remember hamming it up one time with my father pretending to lead me down the aisle, mother thought it was a tragedy I'd not been born a girl, especially one time when she announced I looked better in the wedding dress than the girl who was supposed to wear it.

    Hannah

  25. #25
    Neanderthal in nylons Julie Denier's Avatar
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    [QUOTE=Miss Joanne;2784552]... being a teen in the 80's ... The women always wore pantyhose with almost everything and I loved the look. still do [QUOTE]

    That's a big part of it for me, too. I started clomping around in Mom's heels as a tot, explored her closet on very rare occasions through my early teens, finally dressed full-on in my late 30s.

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