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Thread: What was the first item you wore?

  1. #76
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    One of my mums skirts and tights. No other girls in the home when I was growing up but I'm told that when I was 4 or 5 there was a girl similar age lived 2 doors away and we would often swap cloths and toys......her my Action Men, me her dolls.

  2. #77
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    My mothers pantyhose and her winter knee high boots. I would get very aroused.
    Last edited by char GG; 07-29-2024 at 03:23 PM. Reason: TMI

  3. #78
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    Jackie, a bit complicated but I remember being dressed up as a young girl for a Halloween party (8 yrs old?) at the church but the first time I did it for myself was a few years later (11 or 12). I was occasionally sleeping in the extra bedroom and for whatever reason, looked into the closet and found a bag of older pantyhose and the black go-go boots I wore to that party, put them on and the rest is history.

    Within a few months, I was using any chance I had to try on everything I could, even occasionally faking that I was sick to stay home. Starting the moment I was home alone I would shower and start in nightgowns, etc., working up to business type outfits and dresses as the day wore on.

    I clearly remember every "first" from that day on, first makeup or nails or stockings or stepping out the back door and finally stepping out the front door and driving away.

  4. #79
    Member Misty_cder's Avatar
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    The first item of woman's clothing I wore was my mother's light blue one piece leotard and white tights. She would wear this outfit when she went to aerobics class and then after washing it, hang it up to dry in the bathroom I used.
    I am just a guy who enjoys wearing women's clothing and there is nothing wrong with that.

  5. #80
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    I very clearly remember at the age of 5, I had just had a bath and my mother was getting me ready for bed. She realized that I did not have clean pajamas or underwear as the wash hadn?t been done that week. She asked my aunt, who lived with us, if she had any small panties to put on me. I remember they stood me up and put the panties on me and they giggled and remarked how cute I looked. To have never forgotten this episode of the first time I wore panties surely had an impact on my life long desire to crossdress

  6. #81
    Senior Member Traci H's Avatar
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    Somewhere around age 8, I was at a friends house with my family. My friend and his older sister were pushing me to try on his sisters shoes, some low heeled flats. I did slip them on and they tried to drag me into the room with the adults thinking it was funny I was wearing girls shoes. I got them off, but the incident always stuck with me. I enjoyed wearing them and still do!

  7. #82
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    Hi. My first was from my mom, a black lace bikini panty when I was 11. Memories.

  8. #83
    Aspiring Member krissy's Avatar
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    i wore my sisters pink panty slip it was short and lace accents around the bottom i loved that slip i felt so pretty when i wore it

  9. #84
    Silver Member CynthiaD's Avatar
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    I really don?t remember, but it was either my mother?s panties or one of her slips. Or both. I started with red nail polish at the age of three. I was 12 the first time I dressed fully en femme. Bra filled with socks, panties, slip, and a discarded dress of my mother?s. No wig though. My short hair made my appearance somewhat disappointing. I sometimes would wrap a towel around my head and pretend I was a nun. That solved the hair problem.
    What do I do on days when I don't crossdress? I have no idea.

  10. #85
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    My first outfit was a gymnastics leotard, i now have 35

  11. #86
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    For me it was aged probably about 5/6 so the early 80s, mother always wore tights, grey, barley black or tan, loved them, she never stopped me either, obviously the older I got the more it was frowned upon and soon became a secret.
    Now latter in life still love dressing, wife knows but I have to do it when she's not around, wish she would let me do it with her but that's life....

  12. #87
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    A pair of my sister's panties. They looked like ones worn by a topless model in the newspaper. So I tried them on and my crossdressing started from there,

  13. #88
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    I don't and never will be able to look like them. But the lingerie that they wore always made me want to wear and look like them!
    Last edited by DAVIDA; 08-08-2024 at 05:13 PM. Reason: There is no need to quote the post right before yours, rues.

  14. #89
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    Quote Originally Posted by BrendaPDX View Post
    I am with Jennifer, "L'eggs Sheer Energy Sheer To Waist, Suntan, from an egg!". Loved the way they made my legs look then and love them now!
    So true the early commercials enticed you to slip into their pantyhose

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

    Quote Originally Posted by Misty_cder View Post
    The first item of woman's clothing I wore was my mother's light blue one piece leotard and white tights. She would wear this outfit when she went to aerobics class and then after washing it, hang it up to dry in the bathroom I used.
    Yes same except it was a black leotard and white pantyhose that were like tights soo amazing

  15. #90
    Member BaliGirl's Avatar
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    The first thing I tried was one of my mom's bras when I was 12 or 13. I went into her lingerie drawer when no one was in the house.

  16. #91
    New Member tmannref's Avatar
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    When i was about 12-13 i would slip into my moms panties and bra and stockings when everybody was out of house on a saturday. Loved the feeling of the stockings and i would stuff the bra as
    mom wqas about the same size i was but well endowed in the chest area . Occasionally i would add a dress and heels

  17. #92
    Soccer Mom in Training MsEva's Avatar
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    I think the first thing that I can say was totally fem was a Merry Widow corsolette that the former owners of our hose left behind in a hope chest. The corsolette was left I guess for hopes of a wedding event that never happened for the former occupant. I love the satin feel of the fabric. I was over the moon with the feeling.

  18. #93
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    I am a total Boomer.... first time I tried on was my 1950's Mom's rubberized girdle, the ones with the built in hold ups for stockings. I tried the stockings on as well and (probably) one of her pointy bras, but I don't remember that quite so vividly Pretty sure it must have said "PLaytex" on it somewhere.

  19. #94
    New Member crissy7's Avatar
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    My sisters red bra and panties.She had great clothes that i wore till she moved out.

  20. #95
    Senior Member SaraLin's Avatar
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    It was so long ago that I'm not sure, really, but was probably one of my sister's dresses.

    I was really young (6 or 7, maybe) and to me it was about trying to look like a girl, not so much about the feel.

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