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I Am a Crossdresser

Personal Stories, Advice, and Support 6,500 People

    I first realized something was different

    after I was dared to wear a leotard at my friends house on Halloween when I was 12. From there I wasn't sure why I liked wearing the leotard so much and felt guilty about it. I told a few of my best girl friends about it when I was 14. I would wear my sisters clothes when she...
    crossfitprincess crossfitprincess 22-25, M 5 Responses Jun 16, 2015

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    An Afternoon Quickie

    Several years ago i was chatting on AOL. I hooked up with a guy that dressed sometimes but was more of a CD admirer. We chatted for a while and he asked me if I would like to meet him in a few minutes. We were on the same side of town so it would be easy. He told me that he was a...
    rachaelbalenger rachaelbalenger 46-50, T 4 Responses Sep 1, 2011

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    Room Mate To Boyfriend

    I was living alone when a old high school friend told me he needed a place to live. I needed help with the rent and it was a big house so I said ok. But I had a secret to hide, I was a crossdresser. I had a lot of clothes and loved to dress. Kevin moved in and things went well...
    ammilnet ammilnet 36-40 11 Responses Dec 8, 2012

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    Yesterday was the best day of my life my

    girlfriend came over and treated me like her princess like I was a girl she brought over clothes for me to try on and she did my make up and she made me feel amazing
    chelsea2610 chelsea2610 18-21, T 7 Responses Dec 6, 2015

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    Some months ago, this post was deleted by the

    EP Police for being posted in a group deemed inappropriate. Thanks to my good friend, Kimmi, my little reflection on baseball last summer was saved. ----------------------- My Dad Taught Me to Throw a baseball …But My Stepmom Taught Me to Throw Like a Girl. Yesterday I was...
    deleted deleted 26-30 11 Responses Jun 7, 2014

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    Coming home for summer vacation

    and realizing you want to crossdress is exhilarating. im sad i cant do it though because i cant drive and there are no stores near me. Experience project is where i come to feel loved and to indulge my crossdressing fantasy. Talking to everyone i meet on here makes me happy. I...
    IamKatrina IamKatrina 18-21, M 1 Response Jun 25, 2015

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    Crossdressing Is My Safe Haven!

    I am shy with some insecurities. I am also strong and reliable and have moral principals. I am also very caring and loving towards my wife and son. I am also very likable and easygoing. I also love sports. Baseball, skiing and womens figure skating are my favorite sports...
    emmicd emmicd 51-55, T 28 Responses Jul 12, 2008

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    Here is a fantasy question: If you could switch

    bodies for 24 hours, which celebrity female would you choose to be? This would mean you would also have access to their closet.
    jamie50 jamie50 51-55 20 Responses Jun 28, 2015

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    Starting

    I started crossdressing when I was 8 with one of my mother's slips.  I loved the way she looked when she got dressed.  The bras, panties, stockings and slips she looked so wonderful on her.  One day I found a slip of hers and tried it on.  The feeling of the...
    SamanthaAnne SamanthaAnne 46-50, M 9 Responses Dec 3, 2006

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    Many times I go out shopping

    and trying on clothes in the stores and never had a problem with the the sales staff. Last night was no different. I have a friend that just started crossdressing. Other night when I dressed him up I talked about that I go to a few stores and try on clothes in the stores...
    cdjo cdjo 41-45, M 15 Responses Jan 21, 2015

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    My First Skirt

    I've been cross-dressing for as long as I can remember and will never forget when I purchased my first skirt. About 25 years ago I was living in the UK and got my own place, so decided it was time to get my own clothes (rather than sneakily trying on my mother or sisters stuff...
    michelletrans michelletrans 51-55, T 18 Responses Dec 2, 2012

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    Crossdressing And Flashing At Lake Hartwell

    It was a sunny day. I had recently purchased a two piece bikini. I drove out to the lake and found a remote location to wear my new bikini and layout in the sun. I parked the car. There was another car in the parking lot but I did not let that stop me. I put on my bathing suite...
    rachaelbalenger rachaelbalenger 46-50, T 15 Responses Jul 31, 2011

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    Hi, iam NicolaCD, i have been crossdressing

    since i way a teenager, i started by wearing my sisters panties but got more adventurous when she was out i would wear her nighties and lingerie, i would also wear her party dresses, now i am older i buy my own womens clothes, i am looking for lots of cd or trans friends to...
    NicolaCD NicolaCD 51-55, M 29 Responses Nov 9, 2014

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    It is a sad day. My wife has requested

    that I retire Terrieann permanently. It is a difficult thing to do, she has been a part of me for as long as I can remember and has helped me through difficult stressful times. I'm not sure I can really do this, but out of respect for my wife I feel I must try. Many thanks to...
    ta61 ta61 51-55, T 8 Responses Aug 27, 2015

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     so I decided to put on my maid outfit

    with my new heels, what do you think guys and galls? ;)
    billy1710 billy1710 22-25 3 Responses Jun 11, 2015

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    dave1jonson dave1jonson 46-50, M Sep 14, 2015

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    I've just begun to accept this side of myself

    more seriouslly the past year! I've bought a good amount of femme clothing an makeup lately...an have been wearing panties every day for at least 6 months now (got rid of male underwear)! I've yet to go out in public dressed up...but I hope to someday, an also hope to get...
    TinyDickJohn TinyDickJohn 36-40, M 1 Response Nov 7, 2015

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    It's a dang shame. I dress up

    whenever I get a chance .Last night I had the house to myself, but I was so tired that all I did was take a shower and put on a bra and panties to sleep in. I missed a great chance to enjoy myself.
    mandywantsit mandywantsit 56-60, M 9 Responses Jul 29, 2015

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    My Sister Taught Me To Crossdress ...my Mother Taught Me To Love It.

    At first, it was just a game. My sister wanted a girlfriend to play with and I was the only one around the house. I was 8 and Cin was probably 10. We had fun pretending and all day she dressed me in different skirts and dresses even though most were too big. At the end of the...
    deleted deleted 26-30 33 Responses Mar 27, 2012

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    It makes me happy that,

    yes I may have a blanket slightly covering my legs, but I am sitting in easy view of my neighbours, while wearing leggings, a thong and a hood less sweatshirt while watching the rainstorm and scrolling through EP. I told myself to do it and here I am :)
    deleted deleted 26-30 2 Responses Aug 3, 2015

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    Just ordered padded hip enhancing underwear.

    No more pencil shaped Roxanne!
    Foxanne Foxanne 22-25, T 7 Responses Aug 8, 2015

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    Caught By My Mom

    I remeber when the day I got caught by my mom.  I was about 15 yrs. old.  My mom was on her way to work and I said that I was sick so I could stay home.  She bought it and left for work.  FYI my mom always wore hose and skirts or suits to work, as her job...
    silkiehosewearer silkiehosewearer 31-35, M 36 Responses May 31, 2009

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    Young Crossdresser

    IForgive me for bad mistakes. My Femele name is ashley. and i started crossdressing since I was 16 years. First i dress my mother clothes, and do it for 1 years. Acctualy i haven't buy ant clothes for my self. ;) nobody supports me, i do it for my one. : ) I'am feeling great when...
    skillboy skillboy 18-21 12 Responses Apr 22, 2012

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    I've always been a part time CD

    since I was 20. I'm doing it daily now starting last week.
    Michelle41011 Michelle41011 41-45, T 4 Responses Nov 15, 2015

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    deleted deleted 26-30 22 Responses May 29, 2014

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    Gentlemen, wear stuff

    that fits, I learned that stuffing yourself in too a small dress hurts like hell later. I am watching animal planet with a heating pad on my side and pain reliever in my system... What I thought was that maybe something with a small figure could work like a body shaper... nope...
    darkcuckoo darkcuckoo 18-21, M Nov 13, 2015

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    Went out for the first time dressed

    as a woman. It was very exciting but also scare wish I had done it long time ago
    Lonely47 Lonely47 66-70, T 2 Responses Aug 31, 2015

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    The Art of Crossdressing!

    It didn’t take me long to figure out how to mix and match outfits. Crossdressing is about getting the details just right! Having two older sisters always helped in choosing the right outfits. My sisters had cute dresses, cut off jean, and baby t shirts…not to mention...
    PinkISpunk PinkISpunk 22-25, T 6 Responses Jul 23, 2014

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    I Think Earrings Were The Last Straw...

    There have been several milestones in my early life. You know, the normal events which might be seen as innocent and minor occurrences in a young girls life ...but to a little boy, are likely to cause cosmic shifts in their perception of themselves and the world around them...
    deleted deleted 26-30 26 Responses Oct 20, 2012

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    Kick anyone ? Send pics

    or talking about stealing knickers
    taylormc609 taylormc609 18-21, M 1 Response Oct 27, 2015

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    Just posted some new pics.

    Let me know what you think ;-)
    JessicainNH JessicainNH 46-50, T 4 Responses Jun 24, 2015

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    I have been a crossdresser

    and exhibitionist since I was 13, but for a long time I didn't know what that meant. I would go out wearing just a long shirt, or make some short cut off jeans, sometimes cutting out the part between my balls and ******* and turning them into a miniskirt. But I didn't discover...
    jackiebi11 jackiebi11 46-50, T Oct 26, 2015

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    Chance encounter I had to go to my local Sears

    for something, when I decide to check out the pantyhose section. I was looking thru the 'own brand' section when I noticed a very attractive women also looking thru pantyhose. It didn't bother me I was dressed in men's clothes (I actually enjoy the buzz). I started to check her...
    michelletrans michelletrans 51-55, T 17 Responses Mar 2, 2014

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    Last Sunday, I had a rare day home alone.

    As soon as I knew the coast was clear, I put on my black lace bra and panties with my black fishnet stockings. I did my make up and put on my wig and a cute pair of black heels and went for a walk around my yard and ended up sitting on a chair in my driveway for awhile. I just...
    JessicainNH JessicainNH 46-50, T 10 Responses Nov 6, 2015

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    I get really annoyed

    when addressed "Mister" even though I'm in a skirt and all feminine. If they can't figure out what to call me a simple "you" would suffice
    Leotrine Leotrine 56-60, T Oct 31, 2015

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    I just bought a new long hair blonde wig.

    So excited to try it out <3
    Lovebrittany Lovebrittany 18-21, M 1 Response 2 days ago

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    New white 7" heels and dress tonight :) And

    thanks to a good female friend - some decent hold-ups and a nice new red skirt :))
    GemsHeels GemsHeels 31-35, M 19 Responses Apr 3, 2015

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    At one point I lived in a duplex

    and there was a woman about my age who lived in the downstairs apartment. We shared a basement with laundry facilities. I occasionally looked at her clothing, but her styles never interested me much. I used to go down there in women's clothing to do my chores when I was...
    iwishmichelle iwishmichelle 31-35 3 Responses Jul 27, 2015

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    Tights121 Tights121 18-21, M 1 Response Feb 3

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    Shopping At A Crossdresser Boutique

    About two years ago I was surfing some CD sites and came across a link to a boutique which advertised "everything for the crossdresser." I immediately opened the URL and found just what I had been looking for. Not only did it have everything I was interested in, it was also a...
    becki2582 becki2582 41-45, T 18 Responses Oct 4, 2011

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    Questions Answered

    "Go ahead. Put them on." Adrienne nodded toward the pair of silver satin panties she had placed on the bed. Her boyfriend, Sammy, looked confused by this request, and a little nervous as well. "W-why would I do that?" "It's OK, Sammy. I know. "My panty drawer has seemed a little...
    sammi11 sammi11 41-45, T 60 Responses Jun 25, 2011

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    I want to crossdress

    and want to feel what other think of me, but sadly I don't have stuff to wear :(
    pepe3287 pepe3287 18-21, M 2 Responses Jun 23, 2015

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    Wwhat do you guys think of my latest costs

    dressing purchase omg I'm so in love with this dress! 
    Zoe24 Zoe24 22-25, M 1 Response Feb 3

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    This weekend from Thursday to Sunday night I

    wore my female clothing in front of loads of friends and they all accepted it wonderfully :-) I even applied nail varnish to my toenails which made me even more happy. I'm envious of girls now...
    GemsHeels GemsHeels 31-35, M 8 Responses Mar 22, 2015

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    I have been dressing up

    as far as I can remember and this is my story of how, who and when. I was already used to the female body as I have three older sisters that I have seen their naked bodies many times but my first contact with "****" was my dad's **** play cards that I found by accident while I...
    CDJasmine CDJasmine 26-30 8 Responses Dec 30, 2013

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