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Thread: What is your fondest memory of your early crossdressing?

  1. #51
    Kris islandgirl's Avatar
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    Going to visit my best friend ( a guy) who had a sister my age and size. He would sneak a dress or skirt and sweater from her closet and watch me try the outfits on. He would even tell me how cute and pretty he thought I looked...Game over...I was hooked at 8 years old...Half a century later...it's still a "kick" like no other.
    Kris
    Kris

  2. #52
    Aspiring Member Jenniferpl's Avatar
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    The more I think about it, the part of when I was young was having alone time to dress up.

  3. #53
    Aspiring Member krissy's Avatar
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    my first time out

    when i was ten my mom would leave me and my sister and brother at the movies all day in the summer .well this one time my sister wanted to change clothes with me i told her no but after awhile we went into the womens bathroom and we changed clothes i put on her pink pantyslip her training bra her socks and her pretty pink party dress with bows i felt so beautiful she wanted to go sit and watch the movie i was scared to go down stairs to sit down she kept saying she would tell mom if i didnt so after awhile i went ill never forget the way it felt to walk down those stairs i felt like a queen i felt so pretty i walked down went and sat down and watched the movie right then i remember telling myself this is what i want when i grow up .that i was going to dress like this every day it was so easy back then .any way after awhile she wanted to change back i didnt want to .she started crying and saying she was going to tell mom so i had to change but that was the day i knew this was who i was and wanted in my life .that was before life came along and wives how cant stand me

  4. #54
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    I remember sneaking into moms room when she was out, looking in her underwear drawer and going through her stockings, i found a pair of seamed stockings put them on with her garter belt, wow was so nice, its all ive wanted to do since then, dress up everyday, sadly at moment i dont have any seamed stockings,must get some thinking about it, i feel so sexy and feminine in them with my tight black skirt on

  5. #55
    Addicted To Lipstick donnatracey's Avatar
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    Remember after school (when the house was empty) about 13-14 going into my parents' bedroom and grabbing a dress out of my mom's closet to try on. Then, carefully going into her top dresser drawer (where she kept her lipstick!) and carefully checking each 1 until I found a dark red one to put on.... I was so afraid she would notice that each lipstick was not where she left it.....

    1 time she did comment that my lips looked a bit "red"....always had a problem with chapped lips so used that excuse and nothing else was said..... Must be why I have a fetish for lipstick to this day.....love wearing it as much as possible ...don't buy as much chapstick anymore...

  6. #56
    Keep Looking Up ...... Jolene's Avatar
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    Smile

    Must have been around 12 years old that day after school when I found my sister's school clothes on her bed. Wanted to put her things on so much but I had to work myself up to it. Panties, pantyhose, bra, skirt. and blouse. I feel nice even now thinking about it. Was about the same size as her at the time so everything fit me well. That feeling was like nothing I had ever felt before. The bra around me and the feeling of soft panties around my hips. After that I would wear her things when I could and sometimes my mother's things as well. Got caught and after the Talk, that was it till many years later and here I am.

  7. #57
    Straight Edge Katie1234's Avatar
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    When I was at my friends house (there were 5 others for a sleepover) his sis and mom went chasing us all around the house and I accidentally(before I CDed) got caught and was put in a strapless dress and full makeup (why they did that I don't know why). I think I was 8

  8. #58
    Aspiring Member Nicola2876's Avatar
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    My mum bought a pair of blck stockings by mistake thinking they were tights. I found them and put them in my bedroom drawer. Every night after school I would slip into the stockings and a pair of my mum's heels and walk around the house. Heaven for a 12 year old cder

  9. #59
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    Quote Originally Posted by Joanie_Shakti View Post
    Bikini panties from the 1970s. Specifically, J.C. Penney's "Days of the Week" bikini panties. But the bikinis and hip huggers in general had a cut that you don't much see anymore. Nylon fabric with a crotch in the same fabric instead of cotton crotch. And wild, psychedelic prints.
    Wow does that ever bring back memories Joanie!

    I would have to say one of my fondest memories came about 1966, I would have been 12 or 13 when the family was gone and I put on my older sister's undies and minidress and white go-go boots with a wig of my mother and went into the back yard, my first outing? It was dark and no one saw me but the breeze on my nylon covered legs hooked me for life.

  10. #60
    Aspiring Member Leelou's Avatar
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    Cheerleader Outfit

    By far my favorite memory was 7th or 8th grade our school had Spirit Week, and one of the days was "Battle of the Sexes" day. Basically, it was crossdressing day. One of my best friends was a cheerleader and she "persuaded" me into wearing her cheerleader outfit for the day.

    Needless to say, for a young crossdresser, it was heaven on earth. Some of the boys teased me about how cute I was, and one of my teachers teased me about how comfortable I appeared in the girl clothes. If they only knew--well, maybe they did

  11. #61
    Junior Member VeronicaV's Avatar
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    Lots of playing dressup back then! I was about 10, when I used to do shows in front of my grandmother, with her wig, heals, and silk robe! She always got a kick out of it.
    Having babysitters who also had girls around my age, provided other great opportunities to explore through their closets and try on some clothes. I'll never forget the feeling of putting on a pair of pantyhose for the first time...sheer exhilaration.
    Some memories are a little more permanent. One day I raided through my mom's stuff, and wore her underwire bra the whole day, among other items naturally. At the end of the day however, I was shocked to see a slight outline of the bra across my chest where the "wire" had been! I still have it, and is a reminder everyday of my CD roots.

  12. #62
    Junior Member ashley82's Avatar
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    When I was little I had a big chest of drawers in my bedroom in addition to my dresser... Well some of the drawers held random and off-season things of my little sister. Swimsuits in the winter, sweaters in the summer, tights, and so on. It was hard to ask for more when you're 12.

  13. #63
    Member Lainie's Avatar
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    In a thrift shop

    I started visiting a thrift shop, following someone's suggestion on line. Before that I had just the occasional article of clothing, threw away most of what I bought because I guessed wrong on the size. The SA suggested I try some things on, and pulled some things off the rack for me to try. Felt so accepted, it was a delight. Soon afterward in their upstairs dressing room I put on a dress that zipped up the back and fit perfectly! It was so feminine--I was so feminine--that I almost fainted right there. It took my breath away.

    Lainie

    You're only young once, but you can be immature forever!

  14. #64
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    Wearing a long leg panty girdle for the first time. I loved how it controlled me and girdles have been part of me since. The first one I actually bought was a side zipper long leg panty from JC Penny. The next one I bought at a corset shop with lots of courage and that one was a Promise by Porette. The next one was an open bottom which I realized I could wear under jeans and pants. I need to stop typing.

  15. #65
    Aspiring Member VanessaVW's Avatar
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    I remember my grandma dressing me in her slip, panties (too big) and stockings. I really enjoyed it. Guess it occured a few times until mom and dad found out.

  16. #66
    Junior Member Blake Lively's Avatar
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    Let's see, probably early teens I would search my mom's closet and drawers for bras and stockings. It was, if I remember, just out of pure curiosity that I would wear these things. Than as puberty struck a sexual interest emerged. . Ah those were the carefree days...
    Last edited by Nigella; 04-26-2010 at 12:09 PM. Reason: Too Much Information (TMI)

  17. #67
    Silver Member Dragster's Avatar
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    At about 12 or 13, I put on my mother's hook-side open bottom girdle. I can't remember where the motivation came from, maybe I knew I needed its suspenders to hold up her stockings. It was so tight, it took me quite a while to do up all the hooks and eyes, but I remember trembling with excitement, feeling that I was a little "trapped" in it; it would take me quite a while to take it off if she came back unexpectedly. I had no trouble hooking up her stockings, and boy did it feel good to caress my legs in nylon! in the girdle! I didn't know what was happening at the time, just that it felt fantastic, but panic set in when I realised I had a major clean up to do, before anyone discovered my "misdemeanor".

    I had many more "adventures" in that girdle and stockings, and, if you'll excuse the pun, I've been hooked on girdles and corsets ever since. I progressed to wearing many of her other clothes; my favourite was one of her ballgowns, black lace over pink satin. I can still remember the feeling of its full length skirt swirling around my stockinged legs, and the sound of the back zip going up nearly sent me into orbit. I was really sad when I grew too big to get the zip past my waist.

    Tony
    Last edited by Nigella; 04-26-2010 at 12:10 PM. Reason: TMI

  18. #68
    Silver Member BRANDYJ's Avatar
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    I'd have to say it was not my earliest memories of my adolescent/teen years, but when the first person I ever told, the woman that became my wife, woke me one morning and said that we needed to go shopping for a new dress for me. This was soon after I had firs told her and after a week or so of her trying to figure it all out and accept it. It was not an easy thing for her. So this particular morning was really her way of saying she is really OK with it and is willing to share the experience with me. RIP Dona..and thank you.

  19. #69
    Member makin' it real's Avatar
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    Kid stuff

    Oh gosh! I still vividly remember how fun it was trading clothes with a kindergarten classmate, until mom caught us and SCREECHED! Yikes. That didn't slow me down long, though. It's hard to pick a favorite moment, there were so many that stand out. Like visiting my grandparents and stealing a pair of my aunt's panties. She was only 2 years older than me and wore really sexy clothes.
    Or the day there was a picture in the local, backwoods PA newspaper of a running girl in a string bikini. THAT sure made an impression. I started standing on the side of the tub in the bathroom, folding down the band on my underwear until it looked like the triangles she was wearing.
    Or, oh my goodness, every new, semi-annual catalog from Sears or JCPenneys, with their pages of women's underthings. I would spend hours looking at the demi bras and imagining how they'd feel on me. MMMMmmmmmmm. Yummylicious!

  20. #70
    Member marlacd's Avatar
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    My fondest memory really wasn't when I was just starting to dress. It was when my wife brought home a brite pink skirt for a number in her dance troup. When I saw it, I decided to build a outfit around that skirt. I had to buy a white blouse, heels, and new lingerine for it. Even a new wig. As it turned out, it was a good thing that I had decided to get lacy bra and slip, since the blouse I had bought was a bit sheer, and it was rather visable under that. I also decided that if I was to go that far, that I was going to dipose of the hair on my legs, and wear perfume too! And of course I just had to have my makeup as good as I could get it, and fingernail polish to boot.
    I made sure that as I pulled myself together that I was going to try to not see the whole picture until I was ready.

    When I stepped in front of the full lengh mirror, I was floored!!! After that, I proceded to ruin my makeup, and knew that I was never going to be anything less than a Crossdresser for the rest of my life.

    Isn't it funny that accepting yourself isn't very hard when you do it correctly?
    Last edited by Nigella; 04-26-2010 at 12:12 PM. Reason: TMI

  21. #71
    Lingerie Lover RachelDenise's Avatar
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    It was trying on my mother's Playtex Cross Your Heart bra for the first time. I was about 11 or 12 and her lingerie drawer sang to me like a siren's song. I coulkdn't help myself. And now, I'm soooo glad I took those fateful steps and actions.
    Rachel Denise

    [SIZE="2"]“One day Alice came to a fork in the road and saw a Cheshire cat in a tree. ‘Which road do I take?’ she asked. His response was a question: “Where do you want to go?’ ‘I don’t know,’ answered Alice. ‘Then,’ said the cat, ‘it doesn’t matter.' "
    - Lewis Carroll
    [/SIZE]

  22. #72
    Aspiring Member Samantha_Smile's Avatar
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    I still remember the first time vividly.
    Twas a saturday, I'd have been 12 or 13.
    Mum, dad and my lil bro had gone to town doing the saturday 'big shop' which would mean they would be in Asda for atleast 2 hours before going into town for bits and pieces, from past experience I knew they were always away for 4 hours at the minimum.
    I had intended to spend the afternoon completing Sonic the Hedgehog in one sitting, I got KO'd by the first Dr Robotnik and turned off the console.
    Bored and alone, I made my way to my parents room and mooched around. I went into my mum's delicates drawers and found a white fully satin bra and matching ruffled french knickers. Curiosity took hold, I returned to my room, took my clothes off and went back to the bra and knickers.
    I pulled on the bra and fumbled behind my back for a minute and got the hook and eyes to meet.
    I instantly became aroused (not that I knew what to do with myself at that age) and went into a state of panic.
    I tried franticly to remove it for what seemed like hours (probably seconds) with visions of everyone coming home and catching me. I got it off, put everything away and ran to my room.
    When I looked at the clock, I realised they had only been gone 45 minutes, and then curiosity and some amount of determination took hold.
    I returned to the silkies and slid the knickers on first up my hairless (late bloomer) legs and I felt instantly softer.
    I grabbed the bra again and fastened it, and went to my room and stuffed the cups with a pair of boxers in each side.
    I went back to my parents room to have a look at myself in the full length mirror and I liked what I saw.
    From there it just spiralled for another 30 mins.
    I pulled out some white suspenders and nude stockings, again stopping to look in the mirror.
    Then a little black dress that I never saw my mum wear, it fit me like a dream, and then a pair of black heels (again fit me like a glove (ahhh, youth).
    Paying no attention to my face I kept a check on the mirror.
    I posed around for about 15 mins, and then took everything off with hours to spare.
    I dont think I ever did the saturday 'big shop' again after this day

    And the rest, as they say, is history...
    Samantha -x-

  23. #73
    Senior Member Jennifer in CO's Avatar
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    my 'wedding' when I was 15

    ok...now before you all go off and have a cow it wasn't a real wedding. The summer I turned 15 I spent with my GP's. I also spent about 3 weeks with my aunt (who created Jennifer 5 years earlier). Very long story short, I worked the first few weeks of that summer at the Community Chest my Granddad founded. No pay, but was offered 'payment' of anything I found I liked I could have. So after a couple of weeks there, I had all the clothes for the summer a girl could want...and a wedding dress. So when I went to my aunts to spend a few weeks, I took the dress. My aunt was a beautician (another long story of how Jennifer actually came about) and I'll never forget that Saturday afternoon/night. She had to do the hair of a bride and we 'girls' went with her to the church so she could do the final prep. The week prior, she had done my hair (which usually swished around at mid shoulder-blade) in a style similar to that worn by Farrah Fawcett in the Charlie's Angels TV series a few years later. Well, she wanted pictures of my hairstyle, so once the bridal party left she had a church full of flowers available and I had a wedding dress. So, once everyone was gone, I was put in my dress and with my cousins as 'brides-maids' I had pictures taken. The catch to this was as I was preparing to walk down the isle, my Grand dad appears from a side door wearing a suit. In shock (I really wanted to run but my feet were frozen to the ground) I stood there as he walked up. His words will forever be in my heart and mind..."What...you think I'm going to let my grand-child walk up the isle alone?" As he took my arm and we walked up the isle I saw grandma sitting towards the front. To keep from crying was difficult to say the least. The photographer took the pictures Aunt Jess wanted, then took shots of my cousins and me and also took some of me by myself and with with Grandma and Grand dad. Grandma had one of those pictures on her chest of drawers till the day she died (10 years later). No one ever figured out (as far as I know) that the girl in the picture with Grandma and Grand dad was me, just "someone special" as she would explain the picture. The remainder of that day/evening was wonderful, with Grand dad saying as he and Grandma left that if I came home in a dress that was fine with them, that I was still the same person inside. So I spent the remainder of that summer as Jennifer. It was VERY difficult to go back home and to be "me" when I did as I had by then spent 2+ months living/being a girl. Grand dad said he tried to get mom and dad to let me stay that school year (so I could continue being Jennifer) but they insisted I come home.

    THAT is my fondest memory of childhood...

    Jennifer

  24. #74
    Member Soriya's Avatar
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    Hmmm, for me it would have to be the very first time I dressed completely head to to with makeup and all. I was a lot thinner back then and when I saw myself in a full length mirror I could not believe it was me. I stood there starring at myself for probably over an hour.

  25. #75
    Cute and Southern Fried KerryLynn's Avatar
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    ahhh pleasent memeories. I remember showing my panties to my first "Girl Friend" We were both like 5 or 6 and i had on a pair of my moms panties **not proud of that** We both had a good laugh and she gave me a pair of hers to remind me of her.

    She was also my frist kiss and Her brother and I talked her into eating a piece of cat food with us. Kids are werid again Good times
    [SIGPIC][/SIGPIC]
    I am Evil Monkey..... ooops wrong panties

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