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I Am a Crossdresser

Personal Stories, Advice, and Support 6,343 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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    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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    anyone in San Diego. Bi sailor

    who wants to get back into crossdressing again
    saint0928 saint0928 18-21, M 1 Response Jan 18

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    I cross dress a lot and have been out in public

    a few times but I have to walk everywhere because I don't have a car and I have to do it when my family is away because no one in my family accepts it and only my boyfriend accepts it.
    Eriborn Eriborn 18-21, M Mar 3

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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, 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 8 Responses Apr 19, 2007

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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 61 Responses Jun 25, 2011

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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 10 Responses Nov 20, 2014

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    dressed in nice wite lacy lingerie

    and some new high heels. Look me up in messanger. Same ID as here
    dave1jonson dave1jonson 46-50, M 1 Response Mar 28

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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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    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

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    lol. ok, so my mom's ex boyfriend was a cross

    dresser, I was long before him, but never told my mom. she found out he was a cross dresser after she broke up with him and she threw a ***** fit. we're talking extreme! so now I definatly don't want to tell her I'm a crossdresser yet alone bisexual.
    ThatOneGuy2254 ThatOneGuy2254 13-15, M 1 Response Feb 22

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    dave1jonson dave1jonson 46-50, M 1 Response Mar 9

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    I go for walks dressed

    as a woman all the time. My favorite time was when I went to an ex girlfriend's place and admitted it to her and she let me dress up at her place and then we went for a walk.
    sandralingerie sandralingerie 46-50 6 Responses Feb 24

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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 38 Responses May 31, 2009

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    I don't usually do this

    but I felt like it. I felt like dressing up as Cinderella, and I have no regrets.
    shadowhero92 shadowhero92 22-25, M 5 Responses Apr 4

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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 just noticed on the facebook news segment

    that Will Smith's son Jaden has admitted that he likes to shop and wear womens clothes. Best thing is he doesn't even try to pass as a woman. This has restored may faith in that one day i can go out in whatever i want and not be judged. Hopefully people will take wind of this...
    shadowhero92 shadowhero92 22-25, M 2 Responses Apr 10

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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 absolutly love to dress myself into girls

    clothes. Yesterday I was all dressed up and made pictures of myself. most of them are posted on my profile so take a look if you read this. tomorrow i'll post new pictures of me into a dress or skirt. I'm really exited to go crossdressing again. more people should try it!!
    ChanelleCD ChanelleCD 18-21, T 14 Responses Jan 11, 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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    I wish crossdressers didn't have to be in the

    closet. I wish we could just dress how we felt without having it be attached to certain stigmas and stereotypes. I'm considering starting to dress more effeminately, but feel like I can only really do so after coming out as bi.
    WalterStuart22 WalterStuart22 18-21, M 6 Responses Feb 16

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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 :))
    Junglist013 Junglist013 31-35, M 14 Responses Apr 3

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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, 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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    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, 2014

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    I am currently laying around in one of my short

    sundresses wishing I could share some snapchats 😉😘
    RubYourDick RubYourDick 22-25, M 2 Responses Apr 8

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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 34 Responses Apr 18, 2013

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    Hi, just wanted to say

    that I'm happy that I'll be going to UCLA for college, and that I hope that over there I'll have more freedom to dress and meet more people like me and that like me, so if you're in los angeles hmu lol. woo, i <3 cding
    username00ism username00ism 18-21, M 2 hrs ago

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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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    Laying in bed this morning,

    just my panties and my pillow. Sometimes simple can be so arousing.
    srqgmann srqgmann 56-60, M 5 Responses Feb 26

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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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    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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    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 12 Responses Nov 12, 2014

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    I am a very passable crossdresser.

    problem is. gay guys don't want me . and straight guys only want me as a woman. I'm a crossdresser nor a female.
    tylerlh tylerlh 18-21, M 5 Responses Feb 5

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    I am starting to find my feminine side more

    appealing❤. I always wanted to be a girl, but unfortunately i was raised by a family that doesnt and will never understand us. I have been a closet crossdresser for as long as i can rember. I started with my sisters and mothers clothes until eventually i baught some (few...
    crossdresser1994 crossdresser1994 18-21, M 3 Responses Mar 18

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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...
    Junglist013 Junglist013 31-35, M 6 Responses Mar 22

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    LydiaCDRose LydiaCDRose 18-21, M 24 Responses May 29, 2014

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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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    Lisahugebra Lisahugebra 26-30, T Feb 19

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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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    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 12 Responses Dec 8, 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 13 Responses Jul 31, 2011

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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, 2014

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    I Am crossdresser, I have scare walking outside

    of home, I live in Orlando, somebody help me please
    KayraCasanova KayraCasanova 46-50, M 5 Responses Apr 1

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    I started dabbling in crossdressing

    as young boy. My first time was when I was 6 years old. My mother and I stayed home from church cause we were sick. And I thought that wearing her dress would make her laugh. So I donned her bright pink dress and pearl white heels and walked out to her. Mom just laughed and said...
    TXKSCD TXKSCD 26-30 1 Response Dec 10, 2014

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