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I Started Crossdressing

Personal Stories, Advice, and Support 125 People

    Born in the 60s, the world around me was a

    wonderful place. I distinctly remember at a very early age sitting in the same room as my mother and her sisters would be carrying on in conversation and think nothing of lifting their skirts, adjusting their garters, and smoothing out their tucked in blouses. I found all the...
    AndiTV AndiTV 51-55 8 Responses Aug 10

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    Started Crossdressing A Long Time Ago

    I started crossdressing, wearing panties, pantyhose and lingerie a long time ago. First it started with panties, seeing my sisters panties on the bathroom floor after the showered I could not resist picking them up and feeling them and all of the sudden before I knew it I had...
    pantiescouple pantiescouple 26-30 Mar 5, 2013

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    Last night i confessed to my mom

    that i want to try crossdressing and painting my nails and this morning she bought $100 dollars worth of womens cloths online. Im so glad I confessed to my mom, im going to own my first pair of heels and dress in a week :D Thank you people who replied to my last post.
    Poopoohead17 Poopoohead17 18-21, M 1 Response May 17

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    My First Crossdressing Experience

    When I was about  5 years old, playing round at my aunties house, I accidently wet myself. When I told her what I had done she said don't worry and told me to get undressed.I was then bathed and dried.She the told me the only clothes she had that would fit were my...
    Claire1965 Claire1965 41-45 5 Responses Dec 2, 2010

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    Getting Started

    Just got started need advise
    nfordhaas nfordhaas 41-45 Oct 7, 2012

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    Started?

    Not 100% sure what got me started crossdressing and when it was.I remember as a kid I would look through the Christmas catalogs that would be laying around just before Christmas. When people were around I would be looking through the toy section, and if no one was around I would...
    happilymarriedguy happilymarriedguy 51-55, M Nov 25, 2012

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    Related Experiences

    I started crossdressing in my mother's clothes when I was 10 and became addicted to it almost immediately. A few years later, my little sister caught me at it. I became submissive...
    cdchrystal cdchrystal 46-50, M 5 Responses Sep 29

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    Hi there! I am a 17 year old sissy cross dresser and I have been dressing as a girl since I was little. I was recently found out by my sister. I was home alone at the time and I...
    ThatSissyBoy ThatSissyBoy 22-25, M 10 Responses Oct 1

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    I've become rather open to my family and friends about my crossdressing. Labor day weekend I was attending a family reunion. I was bent over and my panties were showing, when my...
    Phxpaulena Phxpaulena 61-65, M 8 Responses Oct 10

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    I enjoy crossdressing. Right now I am dressed in a nicely fitting black dress, wig, heels and makeup. There is not a thing that I am wearing that is not feminine and I feel good...
    juliemarie2 juliemarie2 61-65, M 1 Response Oct 12

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    I've just read some of your very interesting articles on this subject, so had to get my '2 bobs worth' in. My parents separated when I was very young & I went to live with my...
    zymack zymack 56-60, M 3 Responses Oct 13

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    Im 17, loves crossdressing and diapers. Very submissive and slutty. Want to live with my lover, i live in Pennsylvania. Hoping to find my lover and please him. <3
    AlexBunnyBoy AlexBunnyBoy 18-21, M 4 days ago

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    Wanted to go shopping while crossdressed with my Mother, However since we lived in a smaller town she was afraid we would run into someone we knew. Then one weekend we had to go to...
    Stephaniegirl226 Stephaniegirl226 36-40, M 8 Responses Sep 23

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    It started when I was about 8 we used to go to a local park and play on the swings and climbing frames , on day it was really hot and I was wearing a summer dress and I slid down...
    Maryb96 Maryb96 18-21, F 4 Responses 17 hrs ago

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    I just started exercising! Going to lose 10kgs. Started with the rower for 20minutes. It has been 4 years since I went to the gym.
    Panasonic123 Panasonic123 31-35, F Oct 2

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    After hard work and commitment, I have finally started enrolling in school again. Everything I hoped for did not happen. Instead I am left with more work and more commitment. I am...
    Shaddee Shaddee 22-25, M Oct 9

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    well after 2 years and 3 months free of cutting and 1 year 7 months of not purging it started again. i know i cant let it happen again especially after my parents spent tens of...
    1yr7monthquitter 1yr7monthquitter 22-25, F Sep 22

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    Wellll, exam hasn't started, and I'm already thinking of what to do after exams. XD 7 days of exams, 7 Oct to 13 Oct excluding weekends. I already have planned to have a chalet on...
    TetraZL TetraZL 13-15, F 1 Response Sep 30

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    I started at age 6 or 7, but I didn't have my first orga*m until I was 14, then when I was 14 I'd do it every night!
    gracelynn1 gracelynn1 18-21, F 4 Responses Oct 5

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    Okay so I have no comments to this tag, but let me tell you all a funny story about this subject Okay so I was around 4, and my friends and I sat on some swings and talked about...
    ColourfulDreams ColourfulDreams 13-15, F 9 Responses Oct 6

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    I was seventeen when I first started driving. I was scared, but excited. I knew I'd have my freedom soon. But mom was very impatient. When I got on the road, I couldn't keep the...
    ChelseaMonroe ChelseaMonroe 22-25, F 5 days ago

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    I'm 6'7"185 lbs brown hair blue eyes and a full time cd. You can find me farming in drag in middle TN. Most of my drag is clown drag but when I go to town I dress really girlie. I...
    bobbert720 bobbert720 26-30, M 1 hr ago

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    rate me guys?(: by the way that is me! I love wearing girls clothes and getting attention(: thanks!
    sissyboylovescock sissyboylovescock 16-17, M 11 Responses Sep 27

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    I stop in a bar while out of town just to unwind than she walks in wearing a sixty's style satin shirt dress with buttons down to below her knees, I find myself staring more than...
    satinlover01 satinlover01 61-65, M 2 Responses Sep 27

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    Hi Friends read this http://www.answers.com/Q/Why_do_men_wear_womens_clothes
    lingarielover lingarielover 31-35, M Oct 2

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    When I go out dressed as a woman I usually go at night because I don't want my neighbors to see me, However several years ago I went on an afternoon shopping trip as I wanted to...
    Stephaniegirl226 Stephaniegirl226 36-40, M 10 Responses Oct 3

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    well gurls, I'm Jessica, I am not "truly" in New Hampshire, I'm in Gardner Ma which is about ten minutes south of Rindge NH. there isn't really anybody in my area to connect with...
    JessicaMann JessicaMann 41-45, T Oct 3

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    I came out to my spouse some months ago . She not only accepts but approves and helps me . It is such a wonderful feeling being " out" to/with her . No more secrets on any level...
    MissMsSissy MissMsSissy 56-60, M 9 Responses Oct 4

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    After many frustrating years keeping it hidden, I recently told my wife about my desire to dress. Finally after months of talk it happened. She sent me out on Saturday to buy a wig...
    NaughtyBecky NaughtyBecky 41-45, T 6 Responses Oct 6

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    I have done this a few times to know the feeling of being a pregnant woman. I have used a blanket-pillow belly that has the weight, giving the feeling of a baby. I have slept with...
    Eikenmaster Eikenmaster 22-25, M 1 Response Oct 7

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    I am out now getting some paint And wearing my pink frilly panties and corset feels so good :)-
    prettypatty5 prettypatty5 61-65, M Oct 8

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    Just wore my new pink panties and corset so sexy
    prettypatty5 prettypatty5 61-65, M 2 Responses Oct 8

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    I have been having fun the last few days with my pregnancy belly. Waddling around and feeling the sensation that I could be a mom. I have even been messing with the size...
    Eikenmaster Eikenmaster 22-25, M 1 Response Oct 9

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    I'm thinking of trying a larger size belly when I cross dress pregnant. I like the feel of the twin sized belly I usually end up with, but am thinking of going to a triplet sized...
    Eikenmaster Eikenmaster 22-25, M 1 Response Oct 10

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    I kind of like when people tell me to do all this kinky stuff for them ;x it's such a turn on!
    CoryCD CoryCD 18-21, M 1 Response Oct 10

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    When I'm alone for more than an hour I usually rush to make a large pregnant belly and put it under a certain camisole that was stretchy and put it under a dress that I liked, then...
    VirtualGinger VirtualGinger 13-15 3 Responses Oct 10

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    So if you heard my last story you would know how I was caught wearing a bra. Since then I have been wanting to wear panties, and I've also been a bit curious about an entire...
    ErickHernandez ErickHernandez 13-15, M Oct 11

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    I think I might have gone too big this time around. Downside, I don't think I'd have enough milk for all of my babies in there if they were real.
    Eikenmaster Eikenmaster 22-25, M Oct 11

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    im so excited, a couple of girls i know want to dress me up after a hinted at it. one of them is buying me a maid outfit and high heels that lock. they are also bringing lots of...
    Curio95 Curio95 18-21, M 1 Response Oct 11

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    Mera nam naresh hu. Me cd hu meri wife ka nam kavya hai . Meri wife mere ko ladki kadpaka pehnake liye force karti hai. Sharu sharu mere ko ye shab ajib lagta tha .ek din wo boli...
    nidhih nidhih 26-30, F Oct 11

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    I'm thinking of trying to go out in public dressed pregnant. Not too far, maybe just out to check my mail box.
    Eikenmaster Eikenmaster 22-25, M 2 Responses Oct 11

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    I have been a cross dresser my entire life and I indulge in my hobby whenever possible, much to my wife's disapproval. We have been married 41 years and my biggest mistake was not...
    MCTV MCTV 61-65, M 1 Response Oct 11

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    I love the feeling that my pregnancy belly gives me. When I pretend that I am expecting a baby, I can't help but rub my pretend baby belly. When I look at my baby belly, and feel...
    Eikenmaster Eikenmaster 22-25, M Oct 13

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    My wife old cloth i use in home
    nidhi9skirt nidhi9skirt 26-30, F a week ago

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    Just a girls bathing suit is all
    anygirls anygirls 18-21, M a week ago

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    Just a bathing suit,nothing more nothing less
    likebad likebad 18-21, M a week ago

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    When I was about 12 I was at home by myself so I decided to put on some makeup so I put on some blue eye shadow and blue mascara well I was watching tv and after about an hour a...
    pmgurl pmgurl 51-55 2 Responses a week ago

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