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I Am a Crossdresser

Personal Stories, Advice, and Support 5,291 People

    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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    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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    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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    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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    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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    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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    Anyone around the Chicago land area would be

    able to dress me. I would like a girl that knows about makeup or a cross dresser that is passable that knows about makeup and cloths
    llcoolj1996 llcoolj1996 18-21, M May 20

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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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    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 8 Responses Jul 23

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    A Girls Night In

    This happened to me recently and is true. A little background my wife was in hospital for a few days and I was home alone. I laid out some clothes on the spare bedroom to wear later.The phone rang my neighbor said could she come over for a few drinks and catch up.She arrive and...
    bernadine52 bernadine52 56-60, M 20 Responses Jun 3, 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 62 Responses Jun 25, 2011

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    dave1jonson dave1jonson 46-50, M 4 Responses Sep 6

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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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    Set back at the time

    when I was 10 years old. i have two brothers and two sisters, a mother and my father passed away when i was 6 years old. my eldest sister and brother were in boarding school while me, my sister and younger brother were not. me and my brother who was 8 at that time will finished...
    amaninadia amaninadia 18-21, F 3 Responses May 19

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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 2 Responses Oct 2

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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 20 Responses May 6, 2013

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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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    Hey, this is just about my life

    as a crossdresser so far :) http://gyazo.com/76d532b3499d2f64bd33ba0e9836ced2 Enjoy! :) xxxxxx
    MATTC95 MATTC95 18-21, M 8 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 2 days ago

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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 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 occurences 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. What...
    kayleew2000 kayleew2000 18-21 29 Responses Oct 20, 2012

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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 17 Responses May 21, 2013

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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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    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 28 Responses Mar 15, 2011

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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 20 Responses Oct 4, 2011

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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, M 5 Responses Sep 1, 2011

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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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    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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    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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    hey im a crossdresser

    who has been getting more into forced feminization and i wanted to talk to someone from the dominate side of things, lets talk about thing.
    SaphireTracy SaphireTracy 18-21, T 3 Responses Jul 30

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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 10 Responses Jan 2, 2011

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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

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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 33 Responses Apr 18, 2013

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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 14 Responses Mar 2

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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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    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 20 Responses Dec 2, 2012

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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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    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 7 Responses Mar 2, 2008

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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 14 Responses Jun 7

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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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    I've always had something special

    for dresses , skirts and other fem clothes from very young age I was almost 6 years old when I tried my sister's skirt secretly and liked it, then I was 14 when I start to dig my sister's undies and clothes secretly and I start to wear it when I was alone, I was fully dressed...
    gerryian gerryian 26-30, M 1 Response May 20

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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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    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 10 Responses Aug 5

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    More Than I Bargained For

    My wife and I have been married for 10 years and are very much in love but we do have our own little fantasies as we have learned over the years. She is 5'8" tall, blonde hair blue eyes, in my mind, quite a sexy body, with great legs, a nice ***, and ample breasts. She really...
    Suhayma69 Suhayma69 22-25 9 Responses Mar 15, 2011

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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 15 Responses Apr 22, 2012

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    Hey everyone knows i like dressing up in womens

    clothing and they think am a freak or something but now i dont know what to do now i still want to crossdress but will people lile what they think of my or just **** me off i love crosddressing when ti wear the clothes it makes me feel nice and sexy but i dont know what to do...
    Sexyboy1997 Sexyboy1997 22-25, M 5 Responses Jun 5

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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 10 Responses Sep 7

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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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    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 21 Responses Jul 11

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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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    nidhi9skirt nidhi9skirt 26-30, F 3 Responses 2 days ago

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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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    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 69 Responses Feb 5, 2008

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