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Thread: When did you first crossdress?

  1. #76
    Member AllieBellema's Avatar
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    I was 17, if I recall correctly... it was a wig and a sock hop costume I bought at the local K-Mart. Not sure how I got the courage to take it up to the register to pay for it, but left it in the trunk of my car when I got home until I knew the coast was clear to get it into my room.

  2. #77
    Aspiring Member Karmen's Avatar
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    I was secretly trying on mom's shoes since I was a little boy, but my real first crossdressing attempts came in my teens when I fully dressed in mom's clothes while home alone. At that time I also started wearing panties and pantyhose under my male clothes as much as possible while still living at home. I started fully dress, with wig and makeup and going out like that at night only in my 20s.

  3. #78
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    I was probably 8-9 and was in my parents bathroom which had the shower. Mom's nylons were hanging in there and I could not resist trying them on.

    It laid dormant for a number of years after those years of nylons, but about 20 years ago (I'm almost 60) it came raging back. First was the wife panties, then my own panties, then nylons, then outer wear.

    Just loving the adventure.

  4. #79
    Member Rollermiss's Avatar
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    I think I was 10-11 I bought (second hand) and wore one of my skating partners old costumes. Kind of kept snowballing from their.

    Kelsey

  5. #80
    Ah-May-Lee
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    When I was 15 I was sort of androgynous in dressing, sort of like Bowie or a cast member from a Warhol film, kinda like a glam rocker. Think of the band "The Sweet". I knew I was a girl but didn't start to fully dress as a girl till late teens, then I became a punk girl.
    In solitude where we are least alone. Byron

  6. #81
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    I remember exactly. I could even figure out the day if I worked at it.
    An evening in May, when I was in 7th grade. Home alone, supposed to be doing homework but wasting time reading a paperback. One line in the book described the character getting stepped on by a woman in high heels. Bang!?!? I went back to my sister's room and put on a pair of her heels. Starting borrowing, scavenging, and buying my own after that.

  7. #82
    Member Victoria_Winters's Avatar
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    well I was always curious growning up. It wasn’t untill high school that I actually really wanted to. I saw Sherley Manson from garbage, my favorite band, in a pokedot dress and I wanted to wear it. I got my first clothes that belonged to me durring high school. My mother helped me at the store find something. Super awkward. And after I graduated and moved into my first place I actually started dressing up. That was years ago. I still have most of my original wardrobe including the first dress I ever bought. Can’t fit any of that stuff anymore but I can’t bring myself to get rid of them. I keep deluding myself into thinking I’m going to loose enough weight to don’t my old cheongsam.

    Love that dress. I fell head over heels for it when I saw it and bought it on the spot!
    “Hatred only breeds more hatred.” -The Invid Regis

    “We are star stuff. We are the universe made manifest... trying to figure itself out”. - Delenn

  8. #83
    Gold Member Maria in heels's Avatar
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    I just love this thread every time it comes back up.....

    My first time was when I was about 7 years old and I discovered the world of my grandmothers bra in the bathroom on the drying rack. From there, it jumped to her black patent kitten heel pointy shoes (those killer ones from the late 40's to early 50's). Then behold.....my stepmothers closet with those fabulous pair of round toe black patent platform pumps with those 4 inch block heels from the late 60's to early 70's....i'm still looking for a pair that is just like those....

  9. #84
    Junior Member --Nina--'s Avatar
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    I was 10 my room was in the basement so was the laundry room.

  10. #85
    Member Shayla's Avatar
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    That is the best Mom ever Satellite!

  11. #86
    love to hear from u missynicole's Avatar
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    i remember putting on my mom's bra and panties when i was about 11 or 12.....no one was home at the time.....i did it many times

  12. #87
    Senior Member Angela Marie's Avatar
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    I was about 8 or 9 when I tried on a pair of my mothers black tights. I was immediately hooked. I will be 64 next month so, as many of you probably know, I grew up in a much more repressive area as far as cross dressing was concerned. I’m a runner so when running tights were introduced you can imagine my exhilaration lol. I did not start fully dressing until about 54. I often wonder how things would have turned out if I were in my 20’s today.

  13. #88
    formerly: aBoyNamedSue IamWren's Avatar
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    I have worn items intended for women, once or twice here and there, as far back as 30 years but it wasn’t but just three years ago at age 48 that I wore women’s clothing for the deliberate purpose of trying to look like a woman.

    I’ve learned a lot on how to to do that better and have even, with the help of members from this site who live in my area have found the nerve to go out while dressed.
    I am not a woman nor am I a man... I am an enby. Hi, I am Wren.

  14. #89
    Silver Member darla_g's Avatar
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    i was a young teen in middle school. I put on my mom's stuff while she was away. I somehow decided that my brows were too thick and i proceeded to shave half of them off.

    It was torture in middle school! I wouldn't cross dress again for another 15 years. below was my next attempt.
    Attached Images Attached Images

  15. #90
    Senior Member Robin777's Avatar
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    I was around 12 or 13 and tried on my mothers panties. Then it went on from there.

  16. #91
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    I was 8yr old and it was my mums panties, I have no idea why I felt the need to try them but I do remember feeling good about it even back then and here I am 50 years on and crossdressing me still feels good

  17. #92
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    In my middle teens I explored my mother's drawers, including the one that held her drawers. I tried on her girdles and hose. Loved the look and feel of the tight Spandex and the nylons secured by garters. Still do, but now it's leggings or jeggings. My sister was younger and smaller than me, so no opportunity there. As a 30-something, I would sometimes wear my SO's pantyhose under my suit to the office, and her bodysuits around the apartment.

  18. #93
    Crossdressing Pilgrim KellyGCD's Avatar
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    I remember as a kid, trying on some clip on costume jewelry, so I guess that was the "first" time. As a kid in middle school, I definitely tried on some of my mom's clothes. I guess the rest is history from there.

  19. #94
    Member Sashauk's Avatar
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    I was in my early teens when I discovered my older sister's knickers and bras. I got such a wonderful feeling when wearing them that 50+ years later I'm still wearing knickers and bras.
    Sasha

  20. #95
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    It was so long ago, before I went to school. I can not remember a time when I didn't want to wear girls' clothes. The first time I remember was one summer, I just wanted to wear one of my sister's summer dresses. I asked my mum, (possibly I pestered my mum) and was allowed to wear one for an afternoon. Then, there was a time when we were on holiday, we were on the coast and took at boat trip to a nearby island. The crossing was rough and I got quite wet and had to change. I didn't have any spare clothes and so my mother put me in a pair of my sister's shorts. They were just red shorts, but, even aged 5, it meant so much to me that they were girl's shorts. Then, another time, around about the same age, we were visiting our cousins and for some reason it was decided that we would play doctors and nurses and I was able to wear the nurses dress. Then, as has been mentioned before here, I discovered towels and for a while I enjoyed what I called my 'Fashion Shows'. Then, I discovered where my mother kept her underwear and, after a short period of overdressing, I started wearing them properly, and then I wore them as often as I could. And the rest, as they say, is history.

  21. #96
    Member elliemoss's Avatar
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    I was about 13/14. Out of nowhere I started to notice what ladies were wearing on TV and at night time in bed I was bombarded with thoughts of femme clothes. I finally gave in to an over bearing urge to try on some of my sisters dresses and skirts. It felt amazing and ever since then been hooked. Wassn't until about 10/12 years later until I fully dressed up with wig/full make up/heels. My GF at the time was away for the weekend so I had a girly Satruday watching girlie movies, TV then got dressed up and walked around the block late at night. It was such a unique thrill feeling the cold November wind blowing my dress against my legs and the clipping sound of my heels on the pavement.

  22. #97
    Senior Member faltenrock's Avatar
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    Can'r remember exactly when, but I think I was around 12-13

  23. #98
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    For me it started around 8 years old. I tried my mother's bra on. I was hooked ever since. 40 years later I have never looked back. I have enjoyed the progression, I look forward to another 40. Marie

  24. #99
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    I have dim memories of being a 5-6 yr old, following my mother as she shopped in a nearby department store. Many of those visits entailed walking through the lingerie department in order to get somewhere else. When surrounding by all the bras, panties, girdles and slips that were on display, I covertly looked at them. To this day, I still don't know why the looks were "covert" and not "with longing" or simply neutral. Regardless, when in that surround, everything felt surreptitious to the point of giving me an odd sensation in my belly and embarrassed me. With the hormones that came with adolescence, I again felt the same pit-of-the-stomach fluttery sensation when around my mother's panties, bras and girdles, but the feeling was also accompanied by an overwhelming urge to try everything on, particularly the panties and girdles. That continued, in secret, through high school. I was married soon after college and my wife's panties (girdles were out by that time) fit nicely! Only after our first child was born and I was in my thirties, did I dress completely in my wife's clothes. There was no wig or shoes yet, but after that full dress event, I long for more opportunities to repeat it, but now in my own skirts, wig, slacks, bras, panties, slips, jewelry, makeup and, yes, shoes that fit me. But, I don't yet have a decent pair of boots.

  25. #100
    Junior Member Melanie Vee's Avatar
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    I was in 4th grade and I saw a clip of Jimmy James transforming himself into Marilyn Monroe on Entertainment Tonight. Later that night, I put on some of my mother's lipstick and blush as well as a tank top and bra.

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