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I Started Crossdressing

Personal Stories, Advice, and Support 121 People

    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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    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 1 Response Aug 10

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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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    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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    Related Experiences

    The last time..? Maybe? So it's been a while since my last post (December) and I was thinking about coming out. Well, things took a hold of itself in it's own way and so much has...
    elliecarr elliecarr 18-21, T 1 hr ago

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    Cuffed and detained during the holiday season. I wasn't really caught in the act of crossdressing but I was caught with the clothes for crossdressing. I actually had told this...
    banannasplitz09 banannasplitz09 22-25, M 3 Responses Jul 31

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    I have been married for 15 years. The crossdressing came out about 8 years ago. I was really supportive and loving about it. Felt sorry for Husband that he had had to hide it all...
    LadyLana39 LadyLana39 51-55, F 5 Responses Aug 1

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    I was Caught Crossdressing by my next door nebor Guy and Im still doing it to day. I was in my Wifes We are the same size too. Well I was in her 34-C push up Bra, and Bikini...
    Kellyboy541 Kellyboy541 56-60, F 6 Responses 1 day ago

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    Hi my name is ben I, live in swansea in wales, and im 17. I have long had fantasies about crossdressing, I would love to meet people on here to explore this aspect of my...
    swansea21 swansea21 18-21, M Jul 28

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    Hello everyone I am a 19 Year old Male who previously got addicted to crossdressing. I am strait but for some reason love to wear females clothing, I have tried on several of my...
    MsLexi MsLexi 18-21, F 1 Response 3 days ago

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    Seems like only yesterday when I started occasionally wearing panties under my male clothes. That gave way to wearing panties daily. Then I slowly started wearing a bra. Now I wear...
    pntybra pntybra 36-40, M 1 Response 4 days ago

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    Yesterday started out like most days. I get up in the morning and take a number of my nightgowns, negligee sets out of my closet and put each one on until I find the one I want to...
    silkydrawers silkydrawers 46-50 2 Responses 2 days ago

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    I have been crossdressing since I was in my teens .over the years the compulsion to dress as a woman has intensified dramatically .i now dress completely with full make up and am...
    francescalewis1956 francescalewis1956 56-60, M 1 Response Jul 22

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    I have been crossdressing for a while now but the first time I was caught was when i was 10. I have a older sister that washed cloths with mine one morning, and she had her pink...
    Fogle3 Fogle3 16-17, M 4 Responses Jul 31

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    Every week or so I change my mind about crossdressing. I think its weird and stop, and then later the urge to crossdress returns. I believe it will never go
    kylexdress kylexdress 13-15, M 9 Responses Aug 4

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    So this is a big step for me. I've never been incredibly public about my crossdressing. This is the first thing i've ever done online relative to it with any kind of public...
    EmilyRose15 EmilyRose15 16-17, T 3 Responses Aug 7

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    So, I am fairly new to crossdressing (been at it for about half a year). I keep it a secret and I'm perfectly content with it staying that way. But it has always been a desire of...
    SuperCornstock SuperCornstock 16-17, M 2 Responses Aug 10

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    It's Varied over the Years. In my teens, it was a big part of my sex life, both solo and with my buddy, and to a small part, with a few girls. Then I thought I'd outgrow it. Ha! I...
    AmberFountaine AmberFountaine 66-70, M 2 Responses Aug 10

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    It started off as just wearing my wife's tights. Now I don't know where I am?! I've wore stockings, suspenders & even bought my own heels & it feels so sexy! I've always thought I...
    susspender susspender 41-45, M 5 Responses Jul 26

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    It started when I was around 12 I had a friend that was a girl and we were playin truth or dare and she dared me to wear one of my sisters thongs for a few days and I did I love...
    Pantyhoseboy1 Pantyhoseboy1 18-21, M 3 Responses Jul 31

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    I think it all started with moms pantyhose. Had them stashed in my room. I'm sure she knew. Nothing was ever said. To this day I wear them whenever I can.
    dazzlinglegs dazzlinglegs 36-40, M Jul 31

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    My sister has started self harming again. She was clean for awhile but she started a week ago again.
    blahlahblah599 blahlahblah599 16-17, F Jul 24

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    In my fifties and possibly a bit late to the game. I had a pack lying around from my work and decided to give it a try. To give you some background to my story, I have always been...
    parry03 parry03 51-55, M 2 Responses Jul 28

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    I recently just started my first actual relationship with a guy I've known for a really long time. I'm comfortable around him and I really like him. My boyfriend and I had set my...
    Nala1217 Nala1217 13-15, F a week ago

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    I started fully ************ when I was nine. I remember touching myself a lot prior to that, but I know I started full on ************ every day when I was nine. I still do it...
    Lookingforadvice44 Lookingforadvice44 26-30, M 5 days ago

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    I've been pretty good with not touching a blade, even if it's in sight. I just didn't have the urge to do it. Until a few nights ago, when I started thinking about all the things I...
    SwimmingDarkness SwimmingDarkness 16-17, F 1 day ago

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    I started with my friend when I was 6-7 and ate her and then when I was 7-8 my step brother at that time took me every weekend he had a really big one and he was 17 after that I...
    dirtyperv35 dirtyperv35 31-35, M 2 Responses Jul 22

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    Right, although no one has said anything, I've started to think that my EP speak could be getting annoying. They are pretty obvious, but I'll explain a few of my speech features...
    InternationalDarkness InternationalDarkness 13-15, F 1 Response Jul 22

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    I was probably 12-13 when I started, but I was about 15-16 before I had my first ******.
    emileenicole31 emileenicole31 18-21, F 6 Responses Jul 28

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    There just comes a point in life when you're completely done, it just so happens that that point is now. I'm eighteen and I feel like I have nothing to live for. I had a...
    LeslieMarie247 LeslieMarie247 18-21, F 9 Responses Jul 29

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    My craze for dance and body building started from Salman Khan and still counts on...This was the first song in which my dancer came out of me and still singing the same out of me...
    adiscorpion41 adiscorpion41 22-25, M 1 Response Aug 1

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    I started out wearing Leggs Sheer Energy when I was 6 or 7. My friend and I stole the extra pairs my mom kept in the glove box and we played super hero games. Then when I was 11 I...
    hosedsailorboy hosedsailorboy 41-45, M 9 Responses Aug 5

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    I started today! Im going to do this 3 times a day!
    ShyProdigy ShyProdigy 13-15, M Aug 6

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    Hi I have just started to see someone who has MS. They have had the condition for a long time, and I am looking for a group/place that I can get more information about being a...
    Rosi1e Rosi1e 26-30, F Aug 8

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    i am a multi felon with mental issues who cant get a job because of my record. also cant rent a regular apartment. makes it hard to be self sufficient. so i started a painting...
    ericseamless ericseamless 31-35, M 1 Response Aug 11

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    Started at 5'8" 108 lbs. Now at 118 lbs. I will have to take new pictures since y hard drive crashed.
    btino72 btino72 41-45, M 1 Response Aug 12

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    I started at 13 and have carried on since and now I'm 16
    hdorrington hdorrington 16-17, M 1 Response 5 days ago

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    Started at 9 now I'm 17. Loved it from the start.
    Awesomechoruskid Awesomechoruskid 16-17, M 3 Responses 5 days ago

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    I have started a new tech blog for any techy geeks not got a lot of views really so the more the better and hopefully will get more with time feel free to visit it at http...
    adamridges adamridges 18-21, M 5 days ago

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    I started down a spiritual path after reading Conversations with God a few years ago. Sometimes in reminded just how short of a way I've come since then and it bothers me. I try...
    ollierosser ollierosser 26-30 2 days ago

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    I went dress shopping and found a short little summer dress in black with a lace back, and a nice flared skirt. I love slipping into it and zipping the exposed zipper up my back...
    Plugslave Plugslave 31-35 2 Responses 13 hrs ago

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    Ain't my style, what can I say. I'm not obsessed with female clothing and wearing them. I dress androgynous in some ways and some surfer stuff. I'm into casual clothing.
    KawaiiDemon KawaiiDemon 18-21 1 Response 7 hrs ago

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    Hi i am a female still in middle school and i want to crossdress.But how can i hide it? i mean from my elders and maybe classmates...but anyways it would not be hard for me to fit...
    crosdreser123 crosdreser123 18-21, F 2 Responses Jul 23

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    Hello,my name is jacob but i like to go by zoey. I have spent the last seventeen years of my life alone because I am a girly-boy. Now I have the Internet and sites like this...
    zoey764 zoey764 18-21 Jul 23

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    Hello,my name is jacob but i like to go by zoey. I have spent the last seventeen years of my life alone because I am a girly-boy. Now I have the Internet and sites like this...
    zoey764 zoey764 18-21 1 Response Jul 23

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