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I Am a Crossdresser

Personal Stories, Advice, and Support 6,463 People

     so I decided to put on my maid outfit

    with my new heels, what do you think guys and galls? ;)
    billy1710 billy1710 22-25 2 Responses Jun 11

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    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

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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 Responses Apr 19

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    Worked well. Message the wife saying can't find

    long jhons wearing ur leggings kept my legs warm. She said ok.. hope it a step forward
    24chris24 24chris24 22-25, T 5 Responses Jun 26

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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 33 Responses Mar 27, 2012

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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!!
    deleted deleted 26-30 14 Responses Jan 11, 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 67 Responses Feb 5, 2008

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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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    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 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 4 Responses Apr 10

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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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    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 11 Responses Jun 7, 2014

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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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    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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    Well I finally came out to my group of friends

    about my crossdressing, they were reluctant at first but they supported me regardless. We made a plan to all hang out that weekend and they were expecting me to dress up. I got ready and showed up in a teal, floral print dress with a pair of black tights and flats. I also threw...
    Rockitt Rockitt 18-21, M 7 Responses Apr 28

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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 7 Responses Mar 22

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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

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    Hi everyone! I'm dressed right now!

    !! I partially dressed at work, went to the dentist, Payless Shoes (where I bought a pair of pumps). In my car in the parking lot I pulled down my slacks (I had my skirt on under them), then put on my shoes and blouse. I drove home in heavy rush hour traffic. When I arrived i...
    joanw joanw 61-65, M 3 Responses Jun 23

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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 3 Responses Apr 4

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    I just had by far the best

    and most exciting day of my life. I went out to my local city to look around and do some shopping. I knew the main thing I wanted to buy was a wig. I didn't think I'd actually do it, I thought I'd chicken out and go home on the bus disappointed with myself. In the end I...
    Jenny23694 Jenny23694 18-21, T 6 Responses Jun 20

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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 16 Responses Apr 3

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    I start every day by dressing in hosiery

    and heels with a pretty chemise.
    Plugslave Plugslave 31-35 4 Responses Jun 10

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    I like dressing up in lingerie body suits

    and pretend that I'm a maid. i also like wearing feminene leotards and swimsuits.
    leotardi leotardi 22-25, M 2 Responses May 14

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    I just love sheer nude color stockings with a

    really pretty dress and high heels. I save the black stockings for special times ; )
    Plugslave Plugslave 31-35 1 Response Apr 27

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    My 4 year old daughter bursts in with a proud

    twirl "Daddy, do you like my pretty new dress that mummy bought me?" Somehow it feels like she is taunting me. Like 'ner ner, I've got a pretty new dress and you haven't' but she doesn't know, so it can't be. Oh I hate feeling like this, and I hate myself for feeling like this...
    Heellover Heellover 36-40, M 1 Response May 27

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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 4 Responses Mar 18

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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 11 Responses Nov 20, 2014

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    Came home from a week away first thing I done

    went and bought myself some boxers female ones they are so comfy..
    24chris24 24chris24 22-25, T 1 Response May 12

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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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    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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    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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    deleted deleted 26-30 23 Responses May 29, 2014

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    i just changed out of amazing silk pajama pants

    with a tank top and i am now in bike pants a sports bra and a black thong
    chloerosecd chloerosecd 18-21, M 4 Responses Jun 9

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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 6 Responses Apr 1

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    Comeing Out To A Friend True Story

    Well my dad and was gone overseas for work for a year or more.So my mom asked me to move back whilie he was away.She knew i crossdressed and stay that way for days.Well i moved back home and mom and i was haveing few drinks and we got on subject of who still lived around town...
    cdpaula cdpaula 41-45, F 7 Responses Jul 6, 2010

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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 7 Responses Dec 30, 2013

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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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    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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    Sat in alcudia all i want 2 do is go home

    and put on my girly clothing
    24chris24 24chris24 22-25, T May 11

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    Thanks Mary, I want to have fun; I also want to

    be discreet and respect those that will never understand me. I don't want to be found out. How safe is this site and app.
    nuetrogena nuetrogena 56-60, F 3 Responses Jun 5

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    carsheelsandwomen carsheelsandwomen 36-40 2 Responses Mar 18

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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 26 Responses Oct 20, 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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    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 1 Response Jun 23

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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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    Just posted some new pics.

    Let me know what you think ;-)
    JessicainNH JessicainNH 41-45, M 3 Responses Jun 24

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