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Thread: When did you first crossdress?

  1. #226
    A happy, mature lady! Joy3's Avatar
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    When i was 5 or 6 a neighbor girl liked to dress me as her "girlfriend" at her aunts house and we would play with her dolls, etc. I absolutely loved being her girlfriend. Loved the clothes the feel the look!

  2. #227
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    Under my aunts bed when I was a kid looking for toys, found her box of underwear and hide under the bed all day trying them on

  3. #228
    Junior Member AnnabelleBethanie's Avatar
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    In reality mine was probably longer ago than I can remember since my memory is pretty awful... But the first time I was remember was about 4 years ago when I was 15... I saw my sisters bra is the washing hamper and it caught my eye and I wondered what it was like to wear it... This is exactly what I tried to do, it unfortunately didn't fit and that was actually quite upsetting... So I carried on with my evening as normal, and then suddenly remember my mum is a bigger bra size than my sister so I went and tried that on - as much as it didn't feel right (due to the thoughts in my head that bras are for girls), I was in heaven while wearing it!

    This progressed further into wearing panties, tights and dresses as well... But now I happily have my own bras and underwear.

    Annabelle-Bethanie

  4. #229
    New Member bruce's Avatar
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    I was dressed in little girl clothes by my sister as a todler( or so i was told),she continued til i started school.i never questioned my gender i always just became me.she moved out and i had nothing that fit, as i got older i got caught wearing my friends moms terrycloth sundress. my parent sent me to military school.for 2years there was nothing i could do about it. i started surfing at 12 and the bikini was replaceing the one piece and my oldest niece (3 months younger than me )had a talk and sne stared helping me. we were about the same size cause i really a skinny kid and she gave me her undies and bras and other girlie stuff.parents caught me again and sent me to a shrink.didn't matter the shrink heard what he needed to here and see,and it was just a phase.then came viet nam, well not much going on there but blood,guts,bullets,getting hurt and dope.for the next three years(23yrs old)it was all dope.too doped up to even relate to reality.i had an epiphany and fiured out that if i didn't change my lifestyle i was either going to wind up dead or in prison.no help,just dissapeared and cold turkeyed myself straight,not fun but it worked and has for40 years.at that time i started with just panties(i was a commecial fisherman,5-10 days at sea with 5 other guys)got married had three boys and continued to hide.14 yrs later i caugh ther with a friend of mine. she couldn't give it up so i had to walk away from my kids.i started going more femm and enjoyed it alot. found a girl i new in highschool and wound up getting married again,seven years later i told her that i liked to wear womens clothes,she said;what you like to play dressup?; iwas hurt,scared and for the first time in my life confused! we never spoke of it again.15 years later i drive a tractor trailer for an over the road company and am only home for 34hrs and go rignt back on the road. i now have my own panties,bras,cammis,tops,skirts,shorts etc:. would dearly love to have breast forms but have settled for water balloons. i have to pack up all my girl every weekend and hide it under a bunch of stuff in the bottom of the closet in the truck and hope no one looks too closely while i'm off( sometimes someone will drive my truck while i'm off). i'm happiest while i'm at work but will always come home to my wife .i love her and she loves me but don't ask don't tell.i'm 63 now and have had a pretty good and interesting life and it's getting to the point that i just don't give a shit anymore.
    life's up,life's down life goes on
    metaphisically,we are who we are because we are.

  5. #230
    Member Meg East's Avatar
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    I was probably about six when I started dressing up in mom's dresses. I had the whole basement to myself and more than enough time to experiment. I remember putting on the bra, girdle and lacy half slip and then the dress and heels. Back then both women and men wore hats so once I was dressed up I would put out her hat boxes and work my way through her collection.

  6. #231
    New Member lucidique's Avatar
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    i started when i was 8 years old my best friends sister was a full
    time catholic student all the way from elementary school to high school
    and she was the same size as me all the way hehe so i lucked out
    when she found out that i was ((borrowing)) her uniforms and
    to my surprise she was ok with it and we had a blast playing dress up!!!!!

  7. #232
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    Around 13, I had half a day alone at home every week. I started looking around the house, found wool tights I used to wear for skiing as a kid, found they were very arousing when put with nothing else. Next, I found a stash of my mom's old pantyhose, and I started discovering the wonderful world of tights.

    Once I wanted to try one of my mom's bras, but I was nearly caught that night. I stopped for a while but eventually wearing tights got the better of me and I started buying my own tights. Wearing anything else than tights is a really recent discovery.

  8. #233
    Discovering the Gurl Xandra's Avatar
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    Working your way through the hat boxes sounds delightful.

    Quote Originally Posted by Meg East View Post
    I was probably about six when I started dressing up in mom's dresses. I had the whole basement to myself and more than enough time to experiment. I remember putting on the bra, girdle and lacy half slip and then the dress and heels. Back then both women and men wore hats so once I was dressed up I would put out her hat boxes and work my way through her collection.

  9. #234
    Member marlenesexton's Avatar
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    I used to live a block from my school. Back when things like this were still acceptable, I would walk home from kindergarten and I'd have maybe 20 minutes before my mom would come home for lunch from work. I remember stripping nude and slipping into her pantyhose, even encasing myself in them. I still love pantyhose to this day but I couldn't tell you if that experience drives my love of hosiery or I did because I loved nylons from the get go.

  10. #235
    Senior Member dawnmarrie1961's Avatar
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    Memories can be a very difficult thing to track. Believe me.I've been working on them for years. I can remember my mother painting the nursery walls blue as I laid in the crib looking up at her. Every time I smell fresh paint it brings up that image.So clearly. Like it was yesterday. I remember a lot of bits and pieces of my early childhood. Some memories are good. Others are bad. Uncertain times of difficulty for my parents. My first recollection of wearing girls cloths was at the age of 6 or 7. I was in the first grade. It was a night gown that I would wear when I slept at night. I kept it hidden inside an old wooden radio box beneath a layer of comic books. I'd wait until my three brothers that shared a room with me were fast asleep and then I would slowly lower myself to the floor behind my bed and put the nightgown on. Wearing it helped me to sleep in the dark. I was always deathly afraid of being in the dark. I had sometimes decided to put the nightgown on when I first went to bed and then keep myself tightly covered with a blanket to conceal it. But sometimes my oldest brothers hippie friends would stop in and I'd have to carefully slip the top of the gown off my shoulders. They always came and wanted to read my comics and call me "Faggot." I didn't know what that word meant so it didn't hurt much hearing it until my big brother used it. That hurt. A lot. Especially coming from him. He always apologized for it later when his friends weren't around. The sixties made for some strange times.
    CANCER IS A BITCH SO YOU HAVE TO BE MORE OF A BITCH TO BEAT IT.

  11. #236
    Junior Member Andromeda's Avatar
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    I starter crossdressing when I was about 11 or 12. The first thing I tried was a leotard. Not too long after that I started to wonder what it would feel like to be a woman and I tried first swimsuits and lingerie. While I failed to avevie my goal the experence was interesting enough that I have keeped on dressing.

  12. #237
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    HI Luvs: My first real experience was when I was 14yo , and very embarrassed by the fact that I had tits . An older woman (very sexy 35yo) told me by whispering in my ear that I should wear a

    brassiere , she said "your tits are bigger than mine honey" and she touched my arma nd rubbedit softly right next to my tit . About a week later I saw my older sisters black lacecup underwire

    bra on the floor in her bedroom , it was a 36B and it fit me like I was measured for it and Lo I had tits when I got it on , I have been erect every day since then when I get on a brassiere .

    Two weeks later my mom caught me in her bra girdle stockings and slip . She asked and was told I would not stop so she bought me my first bra pantie girdle and slip a week later.

  13. #238
    Junior Member ErinP's Avatar
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    Easy enough for me to remember. We lived in a few different houses when I was growing up. They got bigger as my parents had more success. So, when I was eight I had a walk-in closet. The former house all the neighbors were girls. And I envied them in their dresses and tights. Loved playing with the toys they had. Barbie and the old tea set thing. But, I wanted to be just like them. So, of course, if you are in the closet no one will know your hiding inside, right? Well I could not believe how beautiful those pantyhose felt! By the time I was twelve I had panties, bras, night gowns and even shoes collected. I remember because that is when the next house came along. That would be the first time I purged!
    "Few are those who see with their own eyes and feel with their own hearts."

    -- Albert Einstein

  14. #239
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    I was about twelve and we were on vacation in Canada. For some reason, my aunt thought it would be a good idea to make me wear a bra. (I still remember it was a padded bra) I was held down and my cousins put the bra on me. Years later my late aunt actually sent me a picture of me wearing the bra. I was crying and look quite upset. Shortly after we returned home, I found myself drawn to my sister's clothing. I started with my sister's one-piece swim suit. Of course, my mom caught me and started yelling at me and asking me if I wanted to be a girl. Surprisingly, I didn't crossdress for another ten years. I still remember getting out of the shower (ten years later) and my mother-in-law's pantyhose were hanging on a towel rack. I couldn't believe the feeling of well-being as I slipped on the pantyhose. I sometimes wonder if they hadn't forced me to wear the bra, I wouldn't be wearing a bra, panties and slip as I write this?
    Last edited by Susan Thomas; 05-14-2013 at 11:36 PM.

  15. #240
    Aspiring Member Nicola2876's Avatar
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    I was 5 or 6 when I gave into curiosity. I found some stuffed toys my auntie had made whilst at her house. They were stuffed with old underwear and tights. I had to wear them so I put on some cotton panties and tights. My heart was pumping so hard and the feeling was better than any drug. Years later when I was about 10 I started to wear mum's tights regularly and a pair of stockings became my daily treat that I used to wear.

  16. #241
    Transgender Member Dianne S's Avatar
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    I used to fantasize about wearing a girl's bathing suit when I was about 6 years old. Tried on some of my cousin's panties and dresses when I was about 9. Seriously got into cross-dressing as a teenager, first with my mom's stuff and then eventually I bought my own female clothes.

  17. #242
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    I started as early as i can remember was 5 years old i used to wear my moms pantyhose (she thought it was cute at the time)* i believe i may have started out younger but any yonger then 5 doesnt really count as CD more just being a child to me lol

  18. #243
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    i agree with you Nicola when i would get dressed up every time i just felt great i couldnt explain it was like a drug i continued to explore myself and what it meant for me growing up at 1st i though it was a fetish cause i couldnt explain it now as im older its not a fetish i feel good and dressing as a woman just makes me happy i love the way i feel and look, and i actually feel attractive for even just a brief moment i LOVE pantyhose and heels always have now i know why hehe

  19. #244
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    my first crossdress

    It happened just fter 7 days of my marriage at around 22 years ago. My wife made me crossdressed. But now ssshe don't like that I. Wear her outfits and it makes me uncomfortble.

  20. #245
    Member Anneliese's Avatar
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    I've always been fascinated with bras and panties. That's why I like the whole "feeling out" process when in a relationship. It is more interesting to me to unclip a bra than to have a girlfriend strip down and get into bed. I liked high heels as a kid also. I still have a good soprano singing voice, and have done female impersonations as long as I can remember (not dressed). I've always thought women's clothes were more interesting and exciting than men's boring stuff. Never actually wore anything from about seven or eight until after my divorce, and then only a couple of times, until about eleven years ago when the pink fog first hit. It only lasted a few months, and then I stashed what I bought until about four years ago. Have spent thousands, all on thrift store clothes, so needless to say, I'm completely addicted.

  21. #246
    Connie Connie D50's Avatar
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    It started when I was in a play for the boy scouts (2nd gread) and dressed at a screaming girl fan for the beatles. I had one older sister and of course my mom both had a ton of great cloths. I would stay home sick in th great and spend the day dressing. the only bad thing was my 2 little sisters would get yelled at for being in my older sisters stuff.

  22. #247
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    I started at about 5 years trying on my aunts girdle a stockings, I progressed to wearing my mothers girdle stockings and nylon knickers with a full slip over the top by the time I was 8.
    It was the 60's and I was a latchkey child ,my sister left home at the age of 16 , so from the age of 8 I had access to the clothes that were left behind by her ,I was able to spend most of my school holidays dressed in my mum's or sisters clothes , doing housework for extra pocket money in a dress pantyhose and my mums pink fluffy slippers.

  23. #248
    Discovering the Gurl Xandra's Avatar
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    I couldn't agree more about male clothes being boring in comparison to women's clothes. No comparison.
    Quote Originally Posted by Anneliese View Post
    I've always been fascinated with bras and panties. That's why I like the whole "feeling out" process when in a relationship. It is more interesting to me to unclip a bra than to have a girlfriend strip down and get into bed. I liked high heels as a kid also. I still have a good soprano singing voice, and have done female impersonations as long as I can remember (not dressed). I've always thought women's clothes were more interesting and exciting than men's boring stuff. Never actually wore anything from about seven or eight until after my divorce, and then only a couple of times, until about eleven years ago when the pink fog first hit. It only lasted a few months, and then I stashed what I bought until about four years ago. Have spent thousands, all on thrift store clothes, so needless to say, I'm completely addicted.

  24. #249
    Pretty jockette LoriFlores's Avatar
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    I've answered so many of these threads I'm starting to confuse myself on dates. Somewhere around age 9, and it was my sister's pink satin tutu. Awesome experience (we've all been there) and I've never looked back!!
    Lori

  25. #250
    New Member Sindy Lovelace's Avatar
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    Ina, I too started young with my Mom's pantie girdle. Strangly a neighbour saw me looking at a lingerie ad in a ladies magazine and brought around a trainer bra which her daughter no longer needed. Mom said I could wear it under my skool uniform it is was not sports day. I grew from there
    luv Sindy X X X

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