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Thread: When did you first crossdress?

  1. #901
    Junior Member suzzi's Avatar
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    All I remember is anytime I was home alone I put on my sisters panties bras nylons shoes and nite gowns! It was so much fun and exciting ! I was 10 or 11 and still enjoy dressing up when I'm alone.

  2. #902
    A happy, mature lady! Joy3's Avatar
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    I was about 5 yrs old when a girl neighbor dressed me up in her clothes so she could have a girlfriend to play with. I loved it very much she and I played many times and i was hooked!

  3. #903
    New Member Sophie Hogletta's Avatar
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    About 12 years old I think. It emerged at exactly the same time as normal sexuality. Kind of in tandem. Then through my teenage years I remained bewildered by it, trying female clothes on every so often. It never really goes away does it. It seems to be very hard coded.

  4. #904
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    I was 12 or 13 - and I never understood it. It still makes no sense to me, as I am not passable at all. If I were pretty, I could almost understand it...

    Good luck. I think this is a good group.

    Cindy

  5. #905
    New Member Sophie Hogletta's Avatar
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    Ballerina outfits. Nice.

    Quote Originally Posted by Joy3 View Post
    I was about 5 yrs old when a girl neighbor dressed me up in her clothes so she could have a girlfriend to play with. I loved it very much she and I played many times and i was hooked!
    My best friend when I was five or six was a girl, but we never did that. You are very lucky! Innocent times . . .
    Last edited by Lorileah; 05-19-2015 at 12:37 AM. Reason: merged several responses. You can add to your reply using the edit

  6. #906
    Member ErikaS's Avatar
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    About three/four years ago have been wanting to wear a black dress and the opportunity presented it self and wow what an fun night.

  7. #907
    Painted toes n panties Cassandra*'s Avatar
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    My first event was in the 1990's. My first wife had this beautiful floral sun dress that just felt like it was calling me. I slipped it on and applied a little makeup and looked in the mirror. Everything just felt right. After this event there was a teddy she once wore and put aside in a bag under the bed. One day we decided to escape for a day trip and the strap was peeking from under the bed( cats must have been playing with it) so I tried it on. felt so goood! She never suspected not to this day. Started wearing VS panties a few years ago and my current wife thinks its weird. My theory is whats the different's between men's UW and women's UW? who's wearing it at the time. Now I've been venturing out and buying my wardrobe.
    cassandra*:cheers

  8. #908
    eyah! Mink's Avatar
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    Quote Originally Posted by susancheerleader View Post
    Does wearing my sisters one piece swimsuit and gymnastics leotard count?
    nope!

    sorry it does not...


  9. #909
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    Tried on pantyhose and heels at age 5. Liked it. The rest is history.

  10. #910
    New Member xXxTina's Avatar
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    At around 18 years of age I discovered a pair of leopard-skin victoria's secret panties in a drawer in my dad's closet. It seemed strange to me for something so sexy and exciting to be in a closet belonging to such an unsexy and conservative dad. Maybe it was his? Or a partner's? Either way, they had a hypnotic power over me.. Mesmerized, I completely undressed myself and put them on in my father's closet -- Oh, they fit perfectly! and they felt incredibly silky!

    What started as a closet lingerie fetish evolved over 9 years into a full-fledged women's clothing lifestyle choice, in which I now love publicly expressing my femininity while wearing women's clothing!

  11. #911
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    I was 5. I tried on my mothers pantyhose. Ever since then I loved pantyhose. In my twenties I started wearing dresses, heels, wedges, and such.

  12. #912
    Aspiring Member Alex!'s Avatar
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    Though I dabbled in crossdressing since my teen years, I didn't go "full up" until April 2006. At the time, I was 36.
    Alex Forbes
    Faux Femme
    Flickr Page

  13. #913
    Junior Member AlexaK's Avatar
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    I tried my mom's panties on a few times, I was probably around 12. At the time, thought I was being weird and such, put it pretty well out of my mind. Little things would popup in the very back of my mind then go away again, forgotten. It stayed that way until after a friend came out as trans and started her transition. Learning more about transgender in general had me thinking about dressing. Was a few more years before denial was finally conquered. That takes me to October, been slowly progressing since then. Came out to a few female friends recently, they are helping when they got time.

  14. #914
    Betsy
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    In our high school, the seniors had at that time, what was called a "Senior Slave day" and There was an auction of sorts in the gym and the underclassmen would bid for the services of the seniors for that day. I was dressed up as a woman for that auction. (Many many years ago)

    I don't have any negative feelings at that time. It was later I tried on some female clothing articles.

    Found it quite exciting!

  15. #915
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    when i was born,mom wanted a girl and went and bought girl clothes,when i was born a boy i had to wear them til i was 2 when my middle sis was born and that was when i started getting boy haircuts which i hate to this day. i experimented on and off from 9 to 22 when i quit for 11 yrs which almost destroyed me and my marriage. ive always been enfeminate but bullys found out quick i was mean and left me alone for the most part.

  16. #916
    Gail gailbridges's Avatar
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    14. It was 1978. About to be 15. Getting ready for sophomore year of HS, and really starting to notice girls.

    (clearly I was a late bloomer compared to a lot of you girls. Story of my life)

    I'll never forget that day. I even remember thinking that day, "This is one of those impactful, life moments." (though more in teen language, I'm sure.)
    I was on my way to the shower in the master bath (attached to mom and dad's bedroom), and saw mom's used, work pantyhose on the floor. I already knew that she had a drawer FULL of her old (runs), laundered hose, (Mom was all about making crafts and did a lot with yarn and nylon) and went poking in there for a pair to try on. Found some, put them on and just laid on their bed.
    Nothing much happened at first besides my erection. Didn't know what to do. Just laid there. But eventually started squeezing my (what I later found out was) prostate, and soon climaxed.

    I've been chasing the dragon ever since.

    While that was the first time involving actually putting something on, and involving masturbation, I remember inklings of things:

    When I was 7 or 8, I was in a kid's bowling league. I remember mom and I were car-pooling with some other teammate's in their car, and mom and I were in the back seat. Well, being that age I slunk down on to the floor (remember when using seat-belts was optional) and I was just hanging out down there, and then just hugged mom's leg for some reason. She was wearing a skirt and nylons (real nylons, not pantyhose. This was probably 1970.) I just hugged her leg and my face was touching her knee. I remember then feeling that was something special to touch.

    When I was 9-ish, a buddy and I were wandering around in some empty fields near our neighborhood and we found a bunch of junk that somebody had likely just dumped there. We were sort of poking through the stuff, and we found these low heels. I was fascinated with them. For some reason, I said to my buddy, "Maybe we should try them on." I don't remember what he said, but I'm sure he looked at me like I was nuts.

    6th grade. 11 years old. (before the obligatory health (sex education) class)
    I remember standing on the basketball court, and wondering if it was possible that as we grow older that maybe we change genders, and it was a secret and no one wanted to let me in on the secret yet. My parents never had the "talk" with me. (I'm still waiting, and they've been dead 10 years. C'mon, that's funny.) My closest sibling was 14 years older than I, and she already had a family of her own. I had NO idea what girls had down there. I thought maybe they had really tiny penises, and they had to have surgery to give birth. I thought maybe boys penises and girl penises touched and pee'd on each other somehow and that's how the girl would get pregnant.

    Anyway, it seems the bullets were already loaded in the gun well before I pulled the trigger.
    it's dumb to be racist.
    Can't we just all agree to hate stupid people instead? There are stupid people in all races, creeds, and faiths. It's a veritable rainbow of stupid out there, AND they don't know they are stupid. What could be more fair?

  17. #917
    Member Heather_Shirly's Avatar
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    I cant remember clearly but the first time i realized i wanted to put something one was finding this blue satin and lae bra, garter belt and panty in the laundry closet of the first house we lived in. I had to be around five or so.

    The first time i remember putting on female clothes was a purple satin full slip. I still remember the chills i got from being so thrilled looking at myself and feeling the satin all over me. I was at least 11 then.

    Lots of cross dressing ups and downs since then...

  18. #918
    New Member Natasha 22's Avatar
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    Bra n thong around 12. Dressing fully at 14

  19. #919
    If only dreams came true. susancheerleader's Avatar
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    I was about 12 or 13.
    I kept taking and wearing my sisters onepiece swim suit and or her gymnastics leotard.
    My mom and sister kept catching me with it on. Or just finding it "hiding" under my mattress and would scold me. I kept taking it anyway but eventually stopped because I was sick of being caught and bitched at.
    It was nearly 40 years later when I bought a skirt on eBay. I have been hoarding other types of clothes since then.

  20. #920
    love to hear from u missynicole's Avatar
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    I was probably about 12 or 13 and would be home alone and would put on my mother's bra and panties. Just now accepting myself.......

  21. #921
    New Member
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    There are more girls in my family and want to dress me as a girl @ 8 yrs

  22. #922
    Gold Member Dana44's Avatar
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    I was about 6 or 7 as I remember playing housewife with my sisters.
    Part Time Girl

  23. #923
    Junior Member Maxie's Avatar
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    I was 11. Took some of my favorite cousins bra and panties.

  24. #924
    Discovering the Gurl Xandra's Avatar
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    I am not passable either, Cindy, and I still don't understand the urge to crossdress. But I love doing it!
    Quote Originally Posted by Cynthia99 View Post
    I was 12 or 13 - and I never understood it. It still makes no sense to me, as I am not passable at all. If I were pretty, I could almost understand it...

    Good luck. I think this is a good group.

    Cindy

  25. #925
    Member LisaKarenAZ's Avatar
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    I was around 9 or 10 and I had gone over to visit my best friend who lived next door, and he wasn't home. It was just his mom and sister home, who told me to wait if I wanted. His sister was playing dress up/house, and told me to join her tea party. What I didn't know was that it was a "girls only" party, and she proceeded to have me dress up in a pretty dress, underwear, training bra, and makeup. Although she was 2 years younger, I was small for my age and we were the same size.

    After playing dolls for a bit, she and her mom thought this was cute, and walked me to see my mom and her friends with at were visiting. They all giggled, said what a cute girl I was, and my mom telling me I shouldn't wear someone else's clothes, and to go change.

    Through the years, I was caught plenty of times by both my parents dressed up.

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