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Thread: What is your crossdressing past?

  1. #1
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    What is your crossdressing past?

    I would like to hear of your crossdressing past, when and how you started and any near misses you may have had.

  2. #2
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    Read the link in my sig. It gives a pretty comprehensive tale of how I wound up becoming a crossdresser, as well as the TG/TS influences in my life.

  3. #3
    Rachel Rachelakld's Avatar
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    my story and potos are on my blog
    See all my photos, read many stories of my outings and my early days at
    http://rachelsauckland.blogspot.co.nz

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    Weirdest woman ever! docrobbysherry's Avatar
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    Here's a unique story for u, Tracy:

    When I was married, my ex and I went to a big Halloween party. Her as a tough little guy in a suit. And, me as a cheezy looking female. Beard, balloon boobs, $3 wig, etc. But, I was wearing nylons, low heels, and a cute skirt!

    The crazy, drunken evening made such an impression on me that I didn't remember it again until 10 years after I began CDing!
    U can't keep doing the same things over and over and expect to enjoy life to the max. When u try new things, even if they r out of your comfort zone, u may experience new excitement and growth that u never expected.

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  5. #5
    Gold Member Helen_Highwater's Avatar
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    Quote Originally Posted by TracyUK View Post
    I would like to hear of your crossdressing past, when and how you started and any near misses you may have had.
    Tracy,
    Welcome to the forum.

    It started with a fascination with my mom's girdles and stockings, moved on to wearing my GF's dresses, started my stash with items rescued from the jumble sale sack. Bought a few things from shops pretending they were presents. First trips out were night time drives and quick walks in a car park. The internet gave me access to sites like this and online shopping. Having a job that meant I worked at home alone on a regular basis gave me plenty of dressing time. One or 2 close calls when my SO came home early. Progressed to going out in daylight before attending a support group one evening who gave me the confidence to go dressed into my first shop and it's continued from there. Still in the closet. And that as they say is 5 decades of my CD'ing life in a nut shell.

    Not a criticism but I noticed your posts so far have all been titled TracyUK. Can I suggest you title them to reflect what it is you're posting about or it will all get very confusing.

    I hope you get as much out of being here as I have.

    Helen
    Who dares wears Get in, get out without being noticed

  6. #6
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    Tracy - Welcome. I hope you enjoy the site. How did you start crossdressing?

  7. #7
    Silver Member Tina_gm's Avatar
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    Making it short- the desire was there since high school, but next to no actual dressing until nearly 30 years later.
    Chickens should be allowed to cross the road without having their motives questioned

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    Hi Tracy, I'm 73 and I've been in this program for 69yrs. it's pretty much a lifelong thing for me. ~~......
    Having my ears triple pierced is AWESOME, ~~......

    I can explain it to you, But I can't comprehend it for you !

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  9. #9
    Junior Member Chancey289's Avatar
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    When I was a little kid, I use to try on female clothes in secret, however that stopped when I was almost caught. It wasn't until about last year I got back in to it and I went all out. I started buying female clothes and make up. Started practicing it, and now I'm here. I think I've gotten quite good at it, and plan on making my first crossdressing public appearance at an anime convention coming up.

  10. #10
    Ice queen Lorileah's Avatar
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    that is a pretty broad question. You can search replies to questions similar, or narrow your focus to something more specific
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  11. #11
    Member Sister Rachel's Avatar
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    Dammit I just spent half an hour writing a full-on history of my crossdressing then managed to lose it while trying to preview it and simultaneously read your original post

    In short ;

    Started at three years old back in 1960 or '61, nearly got caught fully dressed ( bra, panties, tights, petticoat and two-piece skirt-suit ) in my mid-teens, then on and off, purge and splurge, deny and embrace, then, much too late, coming out to wife and family who have all been wonderfully accepting. I wish I'd had more fun before I became a UK size 20 ! Thin as a rail in my early twenties, could have worn all kinds of pretty girl-stuff then
    It's complicated, then again it's simple ... where did I put that skirt?

  12. #12
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    I dont know when I started, I know its not going to stop.
    Last edited by Bruce64; 01-22-2016 at 08:42 PM.
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  13. #13
    KIM SHY KIM's Avatar
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    To be honest I can't tell my story to many times
    It's still so clear of a memory which means it was right even that long ago.
    Around 5yrs playing on the floor with my mom and another youngster I tried on her little nylon footies. I just remember liking the feel. As time went on I grew interested in watching my mom dress and would try her things on. I remember locking her out of flat once while I tried on her stockings and panty girdle. In preteen years I discovered her pantyhose and made a routine of wearing those along with a black bra and beautiful lacey black full slip. In teen years I outgrew her things and actually "lifted" a few things from neighbors clotheslines late at night on my way home from work.
    In late teens I introduced my desires to my girlfriend (now wife of 29 yrs). We grew into things and by mid twenties I started leaving the house totally en fem. After a while I went to a few CD meetings in Chicago bit was still to quiet and shy to enjoy the experiences. Then I had to close things up for along time (at least 12yrs) And thank goodness, after a nice chat with my wife December 2015 Kim came back life FULL BORE!!!
    That's my story
    Kim

    (in secrete -

  14. #14
    Junior Member CallmeAlice's Avatar
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    I cant remember how I started but I was 12ish

    I did it on and off til I was 15, now I do it as often as I can.

    I've never been caught.
    You have to be odd to be number one. ~ Dr. Seuss

  15. #15
    Junior Member Nadine Robles's Avatar
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    Briefly speaking, it all started with a fascination for panties. How much variety of colors, shapes and fabric! early on I fantasized about how would it feel like to wear them on.Needless to say, once I had the chance to try it, there stayed in that special drawer for good...

  16. #16
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    Quote Originally Posted by Nadine Robles View Post
    Briefly speaking, it all started with a fascination for panties. How much variety of colors, shapes and fabric! early on I fantasized about how would it feel like to wear them on.Needless to say, once I had the chance to try it, there stayed in that special drawer for good...
    Me too. Started when I was 10 and been going for 30 years since.

  17. #17
    Aspiring Member Maryesther M.'s Avatar
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    In my early 40s I had to work abroad for a time and the isolation drove me to try a skirt I picked up in an 'offer' bin. I shaved my legs, donned the short skirt and saw that my bottom half looked like my spouse's. What a turn on! At that time things were acquired mail-order only, so 'progress' was gradual. I only ventured out at night, but the risk was half the fun.
    That was 30 years ago now.

    M.

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    I dressed when I was young, before leaving high school. Then I stopped for many years, 25? I just did not think of it.

    One time, during the summer, I was home alone. I was about 17 maybe. I got dressed in my mother's skirt, hose, top, heels (open sandals and my toes stuck out). I did not have a wig so I used a scarf, like a Muslim woman. I decided to go out and walk a few blocks and come back. On my way back I saw some type of repair truck pull up to my house. I ran. I barely got inside before the guy got out of the truck. He saw me go in. Then I had to endure the multiple knocks and bell ringing before he went away. My parents never said anything.

  19. #19
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    Quote Originally Posted by heatherdress View Post
    Tracy - Welcome. I hope you enjoy the site. How did you start crossdressing?
    I started aged about 7 with my mothers clothes, as I got older and had girlfriends I would when possible dress in hers or even her mothers if I found any in laundry pile. I am sure they must have wondered why I took so long in the bathroom.

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

    Quote Originally Posted by Sister Rachel View Post
    Dammit I just spent half an hour writing a full-on history of my crossdressing then managed to lose it while trying to preview it and simultaneously read your original post

    In short ;

    Started at three years old back in 1960 or '61, nearly got caught fully dressed ( bra, panties, tights, petticoat and two-piece skirt-suit ) in my mid-teens, then on and off, purge and splurge, deny and embrace, then, much too late, coming out to wife and family who have all been wonderfully accepting. I wish I'd had more fun before I became a UK size 20 ! Thin as a rail in my early twenties, could have worn all kinds of pretty girl-stuff then
    Rachel, it was the for me, when I was much younger although tall I had a slim waist and wide hips giving a good female shape. Now I need some help.

  20. #20
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    I was 7 at the time and had tried on my grandmothers slip and some of her stockings, got caught 3 times then she decide I had to go see a doctor. Finally at age 14 or 15 found out I was trans. This leads to a whole different outlook on myself which is another story later on. Never stopped dressing but always wanted more. Finally I knew what was missing and now 53 years later am very happy living full time as female.

  21. #21
    Senior Member Abbey11's Avatar
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    I've had an interest in ladies shoes since my early years and my mother would wear her stilettos which I just had to try on. My actual crossdressing and going beyond just admiring women's clothes didn't happen until my 30s when I decided I wanted to try stilettos and went and bought a pair and for a while I just stuck with shoes. I started looking at this site and decided it was time that I went further and bought a dress. Since then it's progressed to to full blown wigs, makeup, skirts, tops, blouses, jewellery, bras, panties, suspenders, more shoes/boots, more dresses. I have purged along the way and until recently had not done any dressing for about a year, however now the desire has flamed again and I'm loving it.
    If your interested I posted some very recent purchases on the 'I went shopping and guess what I bought' sticky, in the clothing and shopping forum, if anyone is interested
    Hugs Abbey x
    Just to add... All you ladies are a huge inspiration to me and for that I thank you x
    Last edited by Abbey11; 01-23-2016 at 05:23 AM.
    OMG!! Owning my femininity .... and I LOVE it!

  22. #22
    Member Andrea Renea's Avatar
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    I've been doing this for going on 52 years in some form or another. Even before I knew what the word "crossdresser" was. Started with mom's things. Now I have two full wardrobes, both male and female.

    I'm my wife's best shopping buddy.

    I wanted to wear girl clothes even before I every did, probably 4-5 years old.

    I married we had three kids and now I have the title grandpa.

    Finally fessed up and told my wife after 18 yrs of marriage. Surprisingly she was really accepting and fussed at me for not telling her sooner. Yes! I'm very lucky.

    Next month will be our 36 anniversary
    Last edited by Andrea Renea; 01-23-2016 at 06:42 AM.

  23. #23
    Member Jennifer0874's Avatar
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    My start was thanks to my older sister who would dress me up when I was 1-2 years old. I have no memory of it, just the stories my family would tell about how cute it was. Then one day I guess my dad put a stop to it. Although I do recall really wanting to be Wonder Woman around age 5 and stealing my younger sister's underoos. I also remember staring at my moms closet around that age.

    Then at 13 it all came back and I've been dressing ever since. Within the past two years I mostly wear women's clothing.

  24. #24
    New Member Cd_scarlett's Avatar
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    My past is not much different. Started very early for me wearing panties and pantyhose. I secretly dressed all through my teens but slowed down in college. Not sure why. By the end of college the desire had returned and increased. I dressed a ton and began going out and meeting people. I had some very interesting encounters with other gurls while en femme during those years... Now I don't get to dress as much as I like due to living arrangement. I have a full wardrobe and make-up now but in just sits in the closet.

  25. #25
    There's that smile! CarlaWestin's Avatar
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    Quote Originally Posted by Lorileah View Post
    that is a pretty broad question. You can search replies to questions similar, or narrow your focus to something more specific
    Youngest w/sisters watched makeup curlers then mom's bra excited about forbidden fantasy connected to BD interest shame denial but continued then revelation acceptance still ridiculed divorced tweener insane but thought boobs were cool meltdown single again full reign to CD met wife cool about alternative lifestyle but not CD so now DADT senior heading for retirement hoping to soften situation but still can CD 12 hours every day/night and wanting more currently dressed like naughty teacher gray wig frumpy dress with fabulous sexy lingerie underneath.

    I've waited so long for this time. Makeup is so frustrating. Shaking hands and I look so old. This was a mistake.
    My new maid's outfit is cute. Sure fits tight.
    And then I step into the bedroom and in the mirror, I see a beautiful woman looking back at me.
    Smile, Honey! You look fabulous!

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