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I Am a Crossdresser

Personal Stories, Advice, and Support 5,215 People

    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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    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 27 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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    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 22 Responses Jul 11

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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 31 Responses Mar 27, 2012

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    nidhi9skirt nidhi9skirt 26-30, M 3 Responses Oct 18

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    Loved to dress up and show on cam in messanger .

    .... in fact I have my red lingerie on right now and am on cam. Look me up - dave1jonson is my YM ID
    dave1jonson dave1jonson 46-50, M 2 Responses Aug 30

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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, M 13 Responses Jul 31, 2011

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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

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    I Got Caught My Little Cousin

    I forgot about this until reading some stories. I was around 10yrs old  and  fully dressed . I was wearing a frilly dress ,stockings with a garter belt . I had on make-up. I was wearing apair of mary-jane shoes,that were to small. It took awhile to get my feet in them, but i...
    cindyloulove cindyloulove 56-60, M 9 Responses Jan 2, 2011

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    Being Discovered By A Friend ...

    So about fifteen years ago, when I was living in Massachusetts, I had befriended a woman who discovered at our workplace that I was wearing pantyhose one day. She was so kind and discreet as she asked me to share a drink at the end of the day as she wanted to discuss something...
    dustywhitney dustywhitney 51-55, T 8 Responses Dec 18, 2012

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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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    dave1jonson dave1jonson 46-50, M 4 Responses Sep 6

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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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    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 11 Responses Nov 9

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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 8 Responses Sep 7

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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...
    PaulaNightshade PaulaNightshade 46-50 4 Responses Oct 2

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    All alone at home. All dressed up

    and having a nice play. Look me up in Yahoo Messanger. Love to chat, voice and cam. ID is dave1jonson
    dave1jonson dave1jonson 46-50, M 1 Response Aug 31

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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 4 Responses a week ago

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    I will be online chatting in Yahoo Messanger

    tomorrow Saturday 4th. October at 10pm. New York Time (EDT). Love to chat, share pics, chat and maybe cam. YM ID is the same as here ..... please look me up. I have posted some special pics in my album
    dave1jonson dave1jonson 46-50, M 1 Response Oct 3

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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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    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 62 Responses Jun 25, 2011

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    Last week i decided it was time to get really

    naughty when i was out shopping. I went to a large department store and and bought some nice black lingerie, bra, garter belt, stockings and panties. I went in to the toilets and texted my wife to skype with me. I dressed up in my new purchases and when she logged in gave her a...
    dave1jonson dave1jonson 46-50, M 1 Response Sep 29

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    Currently in Messanger

    and getting dressed. Anyone want to cam and chat ? ID is dave1jonson
    dave1jonson dave1jonson 46-50, M Aug 31

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    I love dressing like a girl in stockings

    and sexy lingerie and parading around exposing my sissy girly clitty! It's especially fun to show off on cam dressed! Hit me up for c2c fun gurls! sara_cd_4 on yahoo.
    saracd4 saracd4 51-55, T 1 Response Jun 7

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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 7 Responses Aug 25

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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, M 1 Response Aug 1

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    On messanger now ....

    .. look me up for some fun. dave1jonson
    dave1jonson dave1jonson 46-50, M 1 Response Oct 3

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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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    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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    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 6 Responses Jul 23

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    The New Girlfriend

    My wife and I have been married for several years and she, I believe, has suspect my cross dressing desires but has never come out and asked me. I do dress up in some of her clothes when she's not home and has commented on the fact that some of her bras and panties seem...
    Suhayma69 Suhayma69 22-25, T 28 Responses Mar 15, 2011

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    I cross dress almost every night now

    and I've always wanted to be a girl. When I'm with my family I just want to go upstairs and put on some leggings or yoga pants a nice shirt and stuff a bra or something like that. I even cross dress when I smoke because it just turns me on that if I got caught smoking It'd be...
    HockeyPlayer536 HockeyPlayer536 18-21, M 7 Responses Jul 7

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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 35 Responses May 31, 2009

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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...
    PaulaNightshade PaulaNightshade 46-50 2 Responses 23 hrs ago

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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 8 Responses Mar 2, 2008

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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 22-25 8 Responses Dec 30, 2013

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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 22-25 2 Responses 5 hrs ago

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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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    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, M 9 Responses Aug 5

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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...
    PaulaNightshade PaulaNightshade 46-50 2 Responses Oct 22

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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 4 Responses Aug 25

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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

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    Check my tumblr account.

    Online Saturday 10pm EDT time, New Yoor on messager. ID the same as here. https://www.tumblr.com/blog/dave1jonson
    dave1jonson dave1jonson 46-50, M 1 Response Oct 3

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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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    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 12 Responses Mar 2

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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 30 Responses Apr 18, 2013

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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 2 Responses Oct 15

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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...
    PaulaNightshade PaulaNightshade 46-50 2 Responses Sep 27

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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 13 Responses Jun 7

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