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I Started Crossdressing

Personal Stories, Advice, and Support 114 People

    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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    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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    Getting Started

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

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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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    Related Experiences

    Just got my clothes for the day... Can't wait to try them out
    Jess967 Jess967 18-21, M 1 Response Apr 7

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    Aahh the nostalgia... Back into my sisters panties. Lol, my photo looks like a pair of boobs
    Jess967 Jess967 18-21, M 2 Responses Apr 10

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    It really is a fantastic feeling slipping in to a nice skirt or dress and complimenting it with other nice items :) I love wearing dresses and the feeling of how free everything...
    LucyTG LucyTG 26-30, T 4 Responses Mar 20

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    Hi. Im a male 18 at college. Ive been crossdressing for a while but am looking for a female to talk with about it and whatever..message me on here
    Zxi19 Zxi19 18-21, M Mar 30

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    A night out as Rhonda had me visiting a local establishment where a band was playing that I follow. I was with a friend, and she is very acceptable of my crossdressing. I was...
    SweetRhonda SweetRhonda 51-55, T 5 Responses Apr 8

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    I want to know more about crossdressing
    nightfun56 nightfun56 18-21, M 2 Responses Apr 9

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    I like Crossdressing. But I have never told anyone. Do you think I should?
    Pinklovemaddie Pinklovemaddie 13-15 3 Responses 5 days ago

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    I was tired, lonely and needed to relax. I went to the local adult video store and picked up a video. In it, there was a woman who was really cute who wore a white corset, and a...
    wistfulmiles wistfulmiles 51-55, M 5 Responses Mar 23

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    I started smoking weed about 3 months ago and recently i have been wanting to tell my parents. I am going to tell my mom because as a 15 year old girl we have a connection and i...
    scruffy341 scruffy341 13-15, F Mar 22

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    I started posting massive data dumps of myself online because I did not think I was going to make it. I wanted the people I loved to know something truthful about me. I came...
    ObiOneyouremyonlyhope ObiOneyouremyonlyhope 41-45, F Mar 24

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    I an 64 years and just started a catherer-I have narapathy and can't get the bad on. Anybodyhave suggestions? I could reallyusethem.
    dennis2214 dennis2214 61-65, M Mar 28

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    Well I started working out again and this is my second week of working out non stop everyday except the weekends. And I've been eating healthy, 5 meals a day and I feel great!
    andreaespe andreaespe 18-21, F 1 Response Apr 2

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    I started a blog parentsobserve.blogspot.com and I invite other parents to contribute as guest posters. Solid writing skills preferred. If you are a parent, and have great stories...
    nhoccg nhoccg 31-35, M Apr 9

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    I started working out at the gym this. I want to lose about 20 lbs and gain definition. I'm a 38 year old woman and I've never done weights before. This week, after being very...
    lee1898 lee1898 36-40, F 1 Response 5 days ago

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    Hi guys, I'm just new to the idea of perhaps starting smoking. I know that at 35, I'm a little late starting getting into this game. Perhaps a little back story is in order... I...
    bluefireball4949 bluefireball4949 31-35, M 3 Responses 4 days ago

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    She was at first a junior counselor at my summer art program. She is 16 years old and her name is Karina. As for me, I'm 13 and my name is Ron. It was a few days at the beginning...
    nerf25 nerf25 16-17, M 1 Response 13 hrs ago

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    I'd love to crossdress but I'm scared of doing so, because I'm worried I won't be able to like what I see in the mirror when I do so. But I adore make-up and women's clothes.
    lyolyo1 lyolyo1 22-25, M 4 Responses Mar 20

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    I dont know when my cd begin..i my child hood my mom wears my sisters skirt and top,pants etc..mom always tell about my attraction to the girls properties.. so this will be the...
    deleted deleted 26-30 1 Response Mar 21

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    Interesting in chatting to men in my area Johannesburg South Africa. I am bi sexual
    Jhbpantieboy Jhbpantieboy 41-45, M Mar 22

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    I love wearing girls clothes the more girly the better. I'd love to chat to other crossdressers so send me a message :)
    deleted deleted 26-30 1 Response Mar 25

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    I love to ware woman's underwear. Like bras and pantys. I have ever since I was potty trained in my cuz pantys. Is this ok?
    onomaine onomaine 22-25, M 3 Responses Mar 27

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    I crossdress every chance I get. My wife knows but does not participate.
    cdtommy cdtommy 66-70, M 2 Responses Mar 28

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    Hey im 18 in college. Anybody close to that age wanna talk or anything? Im a guy from ct/ny.
    Zxi19 Zxi19 18-21, M 3 Responses Mar 30

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    Sometime my wife makes me cross dress
    bendoverman75 bendoverman75 36-40, M 1 Response Apr 2

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    I should preface this with "I'm pretty sure this is weird," because even I get mad at myself for thinking it. Basically, I'm jealous of my boyfriend when he dresses. I realize this...
    Lynne82 Lynne82 31-35, F 4 Responses Apr 4

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    Fem Sissy Boy is honestly searching for a masculine and protective boyfriend/husband and treat me as your princess wife! I am TG and would even love to dress for you and if you...
    FemGayBottom FemGayBottom 26-30, T 1 Response Apr 4

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    Check out my new photos guys! I'm sure you'll love them
    JessicaCrossdresser92 JessicaCrossdresser92 18-21, T Apr 5

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    Im starting a Ki.K group chat ANY full time cross dressers under the age of 20 This is a chat for crossdressers to show off their outfits talk about shopping clothes and post like...
    lovevspink16 lovevspink16 18-21 Apr 5

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    Look at mycrox-d.com Lingerie for crossdresser
    fercrox fercrox 46-50, M Apr 6

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    Look at mycrox-d.com Lingerie for crossdresser
    fercrox fercrox 46-50, M Apr 6

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    Look at mycrox-d.com Lingerie for men
    fercrox fercrox 46-50, M Apr 6

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    Look at mycrox-d.com Lingerie for men
    fercrox fercrox 46-50, M Apr 6

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    Look at mycrox-d.com Lingerie for men
    fercrox fercrox 46-50, M Apr 6

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    Look at mycrox-d.com Lingerie for men
    fercrox fercrox 46-50, M Apr 6

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    I am Miami FL looking for someane close to here to love wear femenine lingerie
    fercrox fercrox 46-50, M 1 Response Apr 6

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    Panties for men at mycrox-d.com
    fercrox fercrox 46-50, M Apr 6

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    gay men may have crossdresser?
    fercrox fercrox 46-50, M Apr 6

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    After stumbling across a cross-dresser in p**n, all I think about when I'm in public out of my feminine personality is that I wish I was wearing more than just my sisters tight...
    Jess967 Jess967 18-21, M 4 Responses Apr 7

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    I am Miami FL some CD to share experiences
    fercrox fercrox 46-50, M 2 Responses Apr 7

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    I love my friend Mia! She is so cool I can't even cope. Just the other day she did herself a complete makeover to look like an emo guy. It was so fricking hilarious to walk hand in...
    alpaqqa alpaqqa 13-15, F 1 Response Apr 8

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    Got into my sisters bikini and loving it!! Pink frilly bottoms with white and baby pink stripes and a frill top with stripes and polka dots!! Lovin this
    Jess967 Jess967 18-21, M 4 Responses Apr 8

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    How I do so that the balls do not fall out of my panty?
    fercrox fercrox 46-50, M 2 Responses Apr 8

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    The uncertainty is exciting. I will go for drives in a skirt nylons shoes and a blouse with no make up or wig. Then I will go into stores like corner store or a coffee shop or the...
    Brandie1960 Brandie1960 41-45, M 3 Responses Apr 9

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    My older cousin cousin, (a girl) Madie, was babysitting me. As I was only 7 or 8 at the time. She was doing her makeup and I asked can I try some? She then did my "make up" and put...
    Teege07 Teege07 18-21, M 4 Responses Apr 10

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    i want cross dress as a female like all the clothes,have long hair, makeup, jewelry and everything and also learn the ways of women. even how to do sex. plzzz message me and help...
    shifakhan shifakhan 18-21, M Apr 11

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    One of my first times I was around 16 I tried on one of my sister's miniskirts and then I was hooked. And of course I was always attracted to girls in knee socks, so I had to try...
    schoolgyrlKaren schoolgyrlKaren 41-45 2 Responses Apr 12

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