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I Am a Crossdresser

Personal Stories, Advice, and Support 5,265 People

    Yes, I am a crossdresser.

    That's not what this story is about, regretably. Or perhaps it is? I just posted this in I Want to Improve the Experience Project. But I also wanted to give fair warning to everyone of the latest good tidings from EP Admin. I just received another "wonderful" email from EP...
    Kim1girl Kim1girl 56-60, T 22 Responses Mar 20, 2014

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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...
    kayleew2000 kayleew2000 18-21 32 Responses Mar 27, 2012

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    I went out for a run today in my tight lycra

    shorts. Felt very girly! Then got home, had a bubble bath (and a glass of wine!). Got out of bath and put some talc on. Then some barely black hold ups, G-string, garter belt and bra. Put some man clothes on top and had a walk to shop about a mile away for some more wine. My bra...
    GurlyPaula GurlyPaula 46-50 2 Responses Sep 27, 2014

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    I had probably my most embarrassing moment the

    first time I shopped in Ann Summers a couple of years ago. It was in Meadowhall in Sheffield and it was really busy, but I had plucked up courage to go buy something. Anyway I picked a bodystocking and took it to the counter. The girl at the counter explained that the one I had...
    GurlyPaula GurlyPaula 46-50 2 Responses Oct 22, 2014

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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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    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...
    kayleew2000 kayleew2000 18-21 28 Responses Oct 20, 2012

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    I am so excited that I found a pair of 3" Mary

    Jane heels on eBay for under $15! Now to just get paid so I can by my cart...which is full of those shoes, and a few pairs of super cute knee and thigh high socks! ;)
    GingerPrissXD GingerPrissXD 31-35, M 3 Responses Dec 4, 2014

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    A Little Help From the Landlady

    It was the late seventies and I was 16.  I had to move towns to complete my university entrance years (11 and 12).  My parents found board with a divorcee, a lady in her 40's living alone in a large house in a well-to-do suburb.  She was very kind although a little...
    IsaacNewton IsaacNewton 41-45 68 Responses Feb 5, 2008

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    Hello, I am new to EP.

    I have been crossdressing for several years now despite my parents views on the subject. Unfortunately my parents forbid this kind of activity and they usually do random checks of my room and remove any girls clothes they find. But this is all about to stop, I just moved into my...
    LittlemsLexiCD LittlemsLexiCD 18-21, M 7 Responses Sep 7, 2014

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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...
    kayleew2000 kayleew2000 18-21 15 Responses Jun 7, 2014

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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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    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 8 Responses Dec 3, 2006

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    I want so badly to be zipped up in a new faux

    leather skater dress I just saw on F21. So hot ! http://www.forever21.com/Product/Product.aspx?BR=f21&Category=dress_fit-and-flare&ProductID=2000100287&VariantID= I am going to get it, and wear these with it ! http://media.kohls.com.edgesuite.net/is/image/kohls...
    Plugslave Plugslave 31-35 4 Responses Dec 6, 2014

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    Why Are We Here On Ep?

    I've asked myself this very question a few times. What I find interesting is how my answer to this question has evolved over time. Initially, I didn't know what to expect. I simply knew I want to be able to express my feelings about crossdressing and some of my other...
    BizSuitStacy BizSuitStacy 46-50, T 15 Responses Oct 23, 2012

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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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    I am in my hotel lobby right

    now in my skirt and top. Black hose my bra filled to a full c. I just love having my girl clothes on.
    mat2Robin43 mat2Robin43 51-55, M 3 Responses Oct 18, 2014

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    Ever since i was 10 years old i knew i was a

    little different...it all started from a simple curiosity about girl clothes. as i walked into my sisters closet, home alone, and tried on her silk pink panties i was hooked. it was feeling that I've never felt before but all i knew was that it felt right. sure it started slow...
    caligurlx421 caligurlx421 18-21, T 25 Responses Jul 11, 2014

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    WHY is it so hard to find shoes?

    ! All I want is a pair of black mary janes!!
    GingerPrissXD GingerPrissXD 31-35, M 5 Responses Dec 1, 2014

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    I so enjoy wearing my corset,

    thong, and stockings, underneath my little black dress, and my ankle strap high heels. I would love to have my toe nails painted, but that will be later.
    Plugslave Plugslave 31-35 3 Responses Aug 25, 2014

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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 18-21, T 5 Responses Jul 23, 2014

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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 13 Responses Jul 31, 2011

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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 37 Responses May 31, 2009

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    All these years I've been wondering what is the

    main motivation behind dressing up. Internally I feel it: it's a combination of being very excited along with the feeling of wanting to be girly. An endless infatuation with the perfect image I hold inside. The combination of everything that is feminine and obedient along with...
    CDJasmine CDJasmine 26-30 8 Responses Nov 20, 2014

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    So...the Landlady's Sister

    I was asked to flesh (pun intended) out the relationship between my landlady's sister and I. She was a widower (husband killed in a mining explosion) and early forties.  That seemed old to me but she was attractive, vivacious and tall (about 6.0''). ...
    IsaacNewton IsaacNewton 41-45 9 Responses Mar 2, 2008

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    I was abroad on business

    and lost some inhibitions! I went into C&A and bought 3 pairs of sexy panties. The lady that served me looked more nervous than me. I smiled at her and I can't believe how relaxed I was. I browsed round the women's clothes section a little longer and actually enjoyed the looks I...
    GurlyPaula GurlyPaula 46-50 4 Responses Oct 2, 2014

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    Mistress told me to stop by a boutique today to

    pick up my new dress. She just loves how I look in it, and I just love being dressed up. http://www.forever21.com/Product/Product.aspx?BR=f21&Category=dress_fit-and-flare&ProductID=2000100287&VariantID=
    Plugslave Plugslave 31-35 4 Responses Dec 11, 2014

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    Crossdresser problems: thong panties

    and cotton work pants do not mix with cold leather seats! :)
    GingerPrissXD GingerPrissXD 31-35, M 3 Responses Jan 14

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    A couple musings on my philosophy on "passing.

    " I would love to see interesting discussions/debates develop in the comments section, so if you have anything to say, say it! My love for crossdressing stems not from the desire to be female, but from the desire to be feminine. I strive to express my femininity through a male...
    necxo necxo 18-21, T 1 Response Aug 1, 2014

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    Crossdressing In Public

    I sometimes dress in drag, and go out shopping for womens clothes. I dress as classy, and age appropriate as possible, and have gotten a few compliments from saleswomen, and other women, while out "enfemme", on making a nice looking "woman". I love getting...
    JillXD JillXD 56-60, M 9 Responses Apr 19, 2007

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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 15 Responses Mar 2, 2014

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    I feel like I shouldn't be a guy anymore ,

    I like other guys... I like doing girl things... I I dunno.....
    Studdleywizbi Studdleywizbi 18-21, M 2 Responses Nov 26, 2014

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    They Don't Bite

    Yes, I am a crossdresser, but don't get to dress much. No, I wasn't wearing a dress or skirt this time (I only wish! ). This story is another with me in male mode but feeling feminine when the situation presented itself, and , for once, acting on that emotion. It all felt very...
    Kim1girl Kim1girl 56-60, T 16 Responses May 21, 2013

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    Hi im 20 from libya !

    ! Anyone who want to talk !! Massage me !! :)
    Czcz763 Czcz763 18-21, M Dec 6, 2014

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    I am also submissive

    and a slave to my Wife and Mistress. I am working at one of my company's satellite offices out of town but only a day trip away so I will be home tonight. I have had meetings this morning and just got out of one a bit ago. As directed I am wearing panties, pantyhose and my...
    CDtvhhbs CDtvhhbs 46-50, T 2 Responses Aug 19, 2014

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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 17 Responses Dec 2, 2012

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    I work as a Taxi driver.

    This morning I went out to work, under my male clothes I put on a pair of back lacy panties, stockings, suspender belt, a pantie- girdle, and bra. I picked up a job, the chap told me he had no money for the fare. He said he would suck me. I agreed, but said to wait until he...
    debbiestockings debbiestockings 56-60, M 1 Response Oct 15, 2014

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    Cross-dressing has taken me many places.

    And my new fantasy is to buy homecoming and prom dresses that I see in pictures and match the outfits exactly. I look back at all of my girlfriends past dresses that she has owned and found them on DH gate and order them. Experiencing this is so arousing and so sexy. But no...
    Zoe24 Zoe24 22-25, M Jan 5

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    I Am Now Free To CD

    Recently my wife found my femme underwear that i had been wearing. It wasn't much as far as undergarments go, panties, and a bra. She asked who these belonged to? I looked at her and said " they're mine". She looked back at me fir a few seconds with a totally blank stare. "What...
    Beenthere69 Beenthere69 61-65, M 23 Responses May 6, 2013

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    I spent most of today dressed in a pink barbie

    one piece at the gay beach taking load after load I also had on red nail polish and pink lipstick and bright pink socks
    sissy1972 sissy1972 22-25, T 1 Response Dec 12, 2014

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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 19 Responses Oct 4, 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 46-50, M 23 Responses Nov 9, 2014

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    Guilty

    I love cross dressing. I would rather wear womens clothing over mens.  I dont remember what age i was but sometime during my early teens is when i discovered panties, and i would always wear them whenever i had the chance. When i met my wife and we started living together i...
    AmberRosecd AmberRosecd 31-35, T 31 Responses Apr 18, 2013

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    Hey, this is just about my life

    as a crossdresser so far :) http://gyazo.com/76d532b3499d2f64bd33ba0e9836ced2 Enjoy! :) xxxxxx
    MATTC95 MATTC95 18-21, M 6 Responses Aug 25, 2014

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    Just had a sudden urge to buy a leather skirt.

    With a long split at the side and not to short at just below the knees. Allready have a couple of leather mini's that look slutty, especially with boots (Mmmmm!)
    michellecd michellecd 22-25 Dec 2, 2014

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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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    This year at Halloween my wife

    and I were going to Biloxi Miss for the weekend. We got to our hotel on Friday about 2 pm we got checked in our room then went down to the casino and played till about 2am. We went back to our room and while I was in the shower my wife set out some matching nightys that she...
    pmgurl pmgurl 51-55 6 Responses Nov 12, 2014

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    Caught Crossdressing By Mom

    I started crossdressing when i was 6 yrs old. My Mom and Dad were divorced and my Mother worked all the time. By the age of twelve I uded to get dressed up after school and would do my makeup. I had long hair down to my sholders. I looked really good. I would dream about what it...
    jamiecd2726 jamiecd2726 31-35, T 13 Responses Aug 27, 2010

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    I shared my experience yesterday of wearing

    make up for the first time after treating myself to some at Boots chemist yesterday evening. What I didn't know was how hard it is to get eyeliner off! I managed to get the lipstick and eye shadow off with soap and water but I had to go to my client meeting this morning with...
    GurlyPaula GurlyPaula 46-50 3 Responses Nov 19, 2014

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    The Making of a Transvestite

    At age 9, I began wearing panties, slips, hose & heels when home alone. I would priss around the house , pose in front of the mirror & just feel so wonderfully different. This continued until about age 12 when my Mom called me down for borrowing her things & those of...
    dvdfg9 dvdfg9 41-45, T 11 Responses Mar 2, 2008

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    I am a crossdresser,

    and I want to look more androgynous. My wide shoulders make this goal impossible, so I'm wondering if it would be better to get something like hip implants? Does anyone here know about these sort of things and give me feedback about the idea?
    necxo necxo 18-21, T 9 Responses Aug 5, 2014

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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. i am now seeking help from someone who lives near me. i live in Virginia and am looking for some one I can meet, i love EP...
    zoey764 zoey764 18-21, T 1 Response Jul 23, 2014

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