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Thread: When you first started to crossdress.. ?

  1. #51
    Gold Member erickka's Avatar
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    First it was the GF, then off to Goodwill to get my own stuff.

  2. #52
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    I started very young wearing Mom's lipsticks then graduating to bras and panties. I had two sisters who became D cups so large bras were available. I dressed fully when I was 15 and the next 45 years have been full of dressing even though I married.

  3. #53
    Senior Member Farrah's Avatar
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    Whatever girl in the house that was my size at the time.....As a kid, of course, I borrowed my sister's clothes..As I got older, my mom's....

  4. #54
    Aspiring Member kellyanne's Avatar
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    Same as above

    My mother's then my sister's then my own..

  5. #55
    Aspiring Member Jaclyn NM's Avatar
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    Well, at first I wore my mom's, when I was very young, but once I came of age I only wore clothes that I bought for myself. I don't want to wear anyone else's clothes, because it seems to cheapen what I am doing. I only feel comfortable in female clothing that is totally mine.

  6. #56
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    4 or 5 yrs old, found a box of little girls dresses in a closet, One little blue cotton dress was my favorite and I would slip it on and sneak outside to our swingset. Oh what fun swinging and going down the slide. Went from there to Moms, sisters, aunts, cousins etc. started buying my own as soon as I could afford them. Still love cotton sundresses and wear them every chance I get.Which is very often.

  7. #57
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    On the farm where I grew up, there were some old dresses that we used as play clothes. I may have been 6 or 7 at that time. Years later, maybe at 15 or 16, I did try on some of my mom's clothes from her dresser.
    It wasn't until much later, in fact, after being married for almost 20 years, that I passionately began to cd. I bought my first articles at Shopko and Walmart. Since then Target, garage sales and thrift stores. Sometimes shopping is as much fun as dressing.

  8. #58
    Senior Member StacyCD's Avatar
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    At first I wore my mom's clothing--it was what attracted me to crossdressing in the first place. I ended up with a stash of clothes that I 'liberated' before they went to Goodwill or the trash. Since my mom was a real clothes horese, I had a lot of stuff to choose from. Now, I just by my own. They aren't women's clothes--they're mine!

  9. #59
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    Like a lot of folks here I started with my mum's... found a one-piece swimsuit on the line as a young teen, tried it and haven't looked back since....

  10. #60
    New Member Carol Elizabeth's Avatar
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    When did I first start to cross-dress? After marriage. We were both students without a lot of disposable income. One luxury that we "splurged" on was an Atari 2600 - I'm letting my age out here - and she wasn't very good at it. If I beat her at a particular game, she would have to dress in one of her short dresses. As I said, she wasn't very good and we were poor, low stakes games. Eventually, she started beating me and I ended up in the short dress. The thing is, I found losing was more fun than winning and soon was in the short outfits more often than her.


    That means that she found out that I liked crossdressing the same time that I found out. There have been many threads about telling your "significant other" early in the relationship about crossdressing. There are those of us who didn't start crossdressing until after marriage.

    Was she concerned. Of course! All the usual questions that we have read and heard so many times. But after 38 years of marriage, she has pretty much figured out that I'm not going to change (sexual preference or sex) nor am I about to leave her for someone else - it's just part of the package she got when we married.

    But again, when did I start? After marriage as part of a silly wager with my wife on the outcome of an Atari 2600 "Pong" game. Go figure!

  11. #61
    Junior Member Andromeda's Avatar
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    I started at about age 13. I took the usual route and used my mothers clothing.

  12. #62
    Full-Time Duality NathalieX66's Avatar
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    My cousins gave my sister a box full of hand-me-downs, and I just went at it and started putting ensembles together when no one was home.

  13. #63
    Apollo apollogod's Avatar
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    I started at church it was Halloween and my church was doing this big party where everyone had to go as the opposite gender. Go figure that church made me feel like myself.

  14. #64
    Platinum Member Charleen's Avatar
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    My mom's things.
    Comfortable in my own skin.

    "Never underestimate the power of human stupidity, and never cease to be amazed by it!" Lazarus Long

  15. #65
    Aspiring Member Nicola2876's Avatar
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    I started with my Mum's tights and bras then started to buy my own clothes when I had £s to do so.

  16. #66
    Member Suzi Q's Avatar
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    I started with my mom's clothes. Many years later I put on some of my wife's clothes and make-up as a single curiosity. Again many years later I started again and wore my wife's things until I bought some clothes from thrift shops. Now I go into retail stores and try on women's clothes and shoes in drab. I enjoy clerks asking how they can help me and am amazed that I hardly ever see any negative reaction.

  17. #67
    Member carrie-ann's Avatar
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    I was 12/13 I wanted the same dresses as the girls in my school. I had to wait a long time before i had my own dresses. I have them now and I love it.

  18. #68
    Member Pattie O's Avatar
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    I would borrow from my mother's wardrobe and love to use her hairspray and make up when I had the time.Then in my early teens I purchased my first womens clothing from a costume shop - a tutu with leotard and ballet shoes....and they were the first items I ever purged.The first of many purges.Those days are gone - I think I'll just spring clean my wardrobe from time to time now!!

  19. #69
    Member Helen 2's Avatar
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    I had it easy. When I was 9, Mom dressed me in my deceased sister's clothing. When she first suggested it, I immediately rebelled and rejected it, acquiescing only after considerable prodding. The clothes included a training bra, panties, nylon slip, dress & shoes -and I absolutely loved it.
    A week later, she suggested that I dress again, and that time I did not fight it. A week after that I asked her if I could dress, and from that day forward I had open access to my sister's clothing, later Mom's.
    Mom died in '91 and aided, abetted, encouraged and supported my crossdressing until she passed.

  20. #70
    Member Karen43's Avatar
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    I was 5 years old and my family were visiting friends who
    had a daughter the same age. She
    wanted to play dressup and clothed
    me in one of her very pretty party
    dresses. All of the adults thought I
    looked very pretty and the rest is
    history.

  21. #71
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    Quote Originally Posted by tommi View Post
    Girls locker room sneek in after school
    Oh wow. Adventurous spirit, are we?

    For me, cross-dressing was never important (still isn't). It was just how the fabric looked and felt (still is). My very first attraction was to a male polyester shirt in my parents closet when I was a little child. I eventually moved to female clothing as I grew up and entered into puberty (and the hormones screamed). The hormones are in control.

    ... but the interest in smooth things happened first.
    [SIZE="1"]For reference: I do not crossdress to explore my feminine side. I wouldn't call what I do crossdressing. I do not want to be associated with that kind of crossdressing. Female things are very boring to me.[/SIZE]

  22. #72
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    Quote Originally Posted by Helen 2 View Post
    I had it easy. When I was 9, Mom dressed me in my deceased sister's clothing. When she first suggested it, I immediately rebelled and rejected it, acquiescing only after considerable prodding. The clothes included a training bra, panties, nylon slip, dress & shoes -and I absolutely loved it.
    A week later, she suggested that I dress again, and that time I did not fight it. A week after that I asked her if I could dress, and from that day forward I had open access to my sister's clothing, later Mom's.
    Mom died in '91 and aided, abetted, encouraged and supported my crossdressing until she passed.
    Oh wow. Another surprise.

    I can see jesus crying. Your mother must have had a lot of faith in you.
    [SIZE="1"]For reference: I do not crossdress to explore my feminine side. I wouldn't call what I do crossdressing. I do not want to be associated with that kind of crossdressing. Female things are very boring to me.[/SIZE]

  23. #73
    Little Ms Witch Hermione Simpson's Avatar
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    When I was 7, & the first item of clothing I tried on was my youngest sisters school uniform
    Although i'm a witch, I can be nice as well (honestly)

    http://www.facebook.com/people/Hermi...son/1527490088


    Also check out my flickr page http://www.flickr.com/photos/hermionesimpson

  24. #74
    Member Carla4Guage's Avatar
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    Oh the advantages of starting young. I didn't have any sisters and ne3ver thought to think of Mom's stuff. The desire never occured to me until after I turned 57 (my middle life crisis?) Anyway, being 8 bra sizes and 5 dress sizes larger than my wife I had no choice but to buy my own. Probably better in the long run, but boy did I go thru a lot trial & error with mail order.
    I bet I took $200 worth of wrong sizes to the Goodwill store before I finally got a complete outfit that I could wear.
    Now it's straight to Lane Bryant, JCP or wherever; hold it up in front of me, in front of a mirror, and then try it on. It's been a long transition to build the confidence, but I think I've finally made it.
    [SIZE="3"][/SIZE]Hugs,

    Carla

    http://flickr.com/photos/carla4guage/

  25. #75
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    Quote Originally Posted by apollogod View Post
    I started at church it was Halloween and my church was doing this big party where everyone had to go as the opposite gender. Go figure that church made me feel like myself.
    Interesting church! What denomination was that?

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