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Thread: When did you first crossdress?

  1. #976
    ashleighfl
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    Jan 2007
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    NE florida
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    I would wear my sisters panties when I was about 5-6. I liked how hers looked better than mine, but I didn't start wearing other female clothes till I was about 10-11 and have been dressing ever since.

  2. #977
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    The first time I can remember is about 5 or 6. When I was growing up we were quite poor and I remember I had to wear a pair of girls bikini bottoms (kids) but frilly, so we could splash around in a little paddling pool one of my neighbors had set up in the garden. My mum never had the money to buy me some so my neighbour lent me her daughters and I still remember her saying it would be ok as I was so young.

  3. #978
    Junior Member
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    Mesa, Az
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    The first time was when I was really young. I know I was younger than 5. I tried on a pair of my babysitter's panties. Later on I started wearing my mom's clothes when I was home alone.

  4. #979
    Member boots's Avatar
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    Oct 2009
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    I was attracted to my aunts fur and suede coat when I was 4.I loved the feel and never quit dressing up since then

  5. #980
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    In started when I was 35...late starter. My first dressing session was in a festish place. The lady dressed me up..... It was out of world feeling. I felt like I am me but not exactly me. I can recognise my voice but not myself. Its an awesome feeling.

  6. #981
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    Personally I blame a Perfect Storm of the old Batman TV series and early 70s womens' fashion!

    It's about 1973 and I'm 6 years old. I was totally into Batman and decided I had to have a Batman costume. At the time brightly colored tights were a big thing in fashion and my 18 year old sister had a drawer full of them. I grab some black, gray and yellow tights, find myself some scissors and start snipping away. When I was done, I realized I made a huge mess I couldn't talk my way out of easily. I also realized the tights were making me feel really, REALLY good for some reason! Needless to say I got caught.

    I periodically wore tights and pantyhose in my room but that was it. I fully dressed up for the first time when I was 47. Sometimes I think I'm not so much a crossdresser as a hosiery fetishist who put up with all the other female clothes to get a chance to wear stockings in public in a (reasonably) acceptable way!

  7. #982
    Banned Read only
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    Oct 2014
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    When my wife found a pair of panties and a bra in my truck! JUST KIDDING, I don't have a truck! 😂 Just reading some serious threads and needed a laugh, sorry!

  8. #983
    Junior Member
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    Sep 2011
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    When I was in my teens one of my sisters and her girlfriends decided it would be fun to see me in a dress. Sometime later I started wearing my mothers clothes. For many years I was a secret crossdresser, wondering what was wrong with me and being ashamed of myself. More recently,thru the internet, I have come to enjoy myself and really make and effort to pass. So, maybe the first time I realy crossdressed was when I went into a bar and asked for a glass of wine, enjoying myself although the others present knew I was a guy in a dress.

  9. #984
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    When I was 6 or 7 I looked in my sisters underwear drawer and tried on silk panties. As a teenager, almost daily after school I would try on a pair of my sister's panties, she had lots of sexy undies. I didn't know what a thong was until I found one of hers and when I tried it on, that was a defining moment for me. For years I just loved panties and never really thought about dressing up more. It wasn't until my 20's that I was able to acquire and keep my own clothes. Now I dress head to toe, I like the way I look as a girl, and love the way I feel.

  10. #985
    Discovering the Gurl Xandra's Avatar
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    Dec 2005
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    Minneapolis
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    176
    Love it. Thanks!

  11. #986
    Silver Member Bobbi46's Avatar
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    May 2015
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    France, Villessot near St Christophe
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    Properly? about three years ago, knowing I could do it and not worry of getting found out by family etc.

  12. #987
    New Member VictoriaBabes's Avatar
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    Feb 2015
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    I was 11 and I first started with undies. Had an older sister and I always had a fem shape so it just seemed natural. I used to wear sexy type of undies and loved mini skirts. I stole a few mini skirts from here and hide them in my room lol

  13. #988
    Member Scarlett Viktoria's Avatar
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    It was about 5 or 6 years ago while my wife was away on business. I always loved womens clothes and became curious to know what they felt like on. So I siezed the opportunity and tried on every dress and pair of heels in the closet. I loved every bit of it from then on.

  14. #989
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    I started at eleven putting on my Nanas bloomers, in those days there were only two kinds of colored panties white and pink. While I could pass many years ago, if you were found out you ended up in jail if you were lucky, other wise you had the crap beat out of you by those others.I often wonder today what does and old lady do today with all you young lovely ladies present. OH MY PegyL

  15. #990
    Aspiring Member MissDanielle's Avatar
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    Nov 2015
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    Chicago!!!
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    8th or 9th grade. Off and on since but it's due to a woman being stuck in this body if I had to guess.

  16. #991
    Fantasy Dreamer Sarah.Jane's Avatar
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    Oct 2015
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    North Wales, UK
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    wow, i love this thread.
    I think I was about 9, I stole some of my little sisters clothes, a slip and skirt, luckily she was bigger than me so I could wear them, I used to steal clothes when we visited people.
    Now internet shopping doesn't help my bank balance.
    Sarah Jane : > I wish I was a house wife

  17. #992
    Member Jacqueline StGermain's Avatar
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    Oct 2015
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    Denver area
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    Before kindergarten ( like 5?). Tried on my cousins stuff , we remained the same size for the next 25+ years,
    We look almost like twins ( she doesn't know ), my sister and I don't look at all like siblings, plus her stuff was a little too small for me.

  18. #993
    Aspiring Member
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    Oct 2015
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    brewerton ny. north of syracuse ny
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    I was 10 , and had a dress and tights in that were my step mother's. Wow, 50 yrs ago. Been doing it ever since

  19. #994
    New Member
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    Nov 2015
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    I was 11 years old. Sneaked my mom's panties and a bra. Didn't know at the time this was a lifelong thing. My wife surprises me with new dresses at birthdays and holidays. She knows this is something that kind of defines who I am. I don't go out dressed up.. But I do often sleep in my panties and a nightie.. Always look forward to opportunities to get some dress time.

  20. #995
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    I was around 10 or 11. Growing up with older sisters always made it easy to try on different things.

  21. #996
    Junior Member AltairaMorbius's Avatar
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    Jan 2013
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    Around 7 here, we lived in a small house with one bathroom, where Mom would wash and dry her delicates as she called then. I remember on the weekends her soaking her panties in the sink then hanging them to dry, along with her heavy duty bras in the bathroom. One night before my bath I looked in the hamper and found a pile of her panties ready for the wash. I remember to this day that my heart was pounding as I stepped into them and pulled them up. After that it became an on and off again thing for the next 50 years, lately it is mostly on.
    Last edited by AltairaMorbius; 11-09-2015 at 02:19 AM.

  22. #997
    New Member shining-sera's Avatar
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    Aug 2015
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    I was around 11 or so when I first tried on a pair of my mom's underwear. My parents found out I took it and had a long conversation about how wrong it was for boys to wear girls clothing (my parents are pretty conservative). Needless to say, my family still doesn't know anything about my habit.

  23. #998
    Junior Member
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    Nov 2015
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    I was probably around 12. I always liked swimming or showering in clothes. One day when my parents weren't home, I got the idea to wear mom's bra and underwear under the clothes that I was showering in. That progressed to showering and bathing my mom and sister's clothes and bathing suits.

  24. #999
    Member Scarlett Viktoria's Avatar
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    Am I the only girl that started in her late 20's? Lol.

  25. #1000
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    Around age 13, my Mom wanted a girl, imagine growing up knowing that - conflicting thoughts. Started with a me and mom wearing the same size 12 pants, then it progressed to her painting my face with makeup then it went to white bikini undies that I tried on, it was a fetish for about 7 years, (got in trouble once, parents thought i was gay and grounded me, my Mom hasnt changed her idea of anything my Dad doesn't care one way or the other.

    I started buying my own stuff around age 16-17, the fetish disappeared after I went out in public a few times. I purged many times and then started hording certain things, went thru styles like a teenage girl changes clothing.

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