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I Am a Crossdresser

Personal Stories, Advice, and Support 6,486 People

    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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    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 16 Responses Mar 2, 2014

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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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    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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    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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    deleted deleted 26-30 23 Responses May 29, 2014

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    Just ordered padded hip enhancing underwear.

    No more pencil shaped Roxanne!
    Foxanne Foxanne 22-25, T 6 Responses Aug 8

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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 51-55, M 29 Responses Nov 9, 2014

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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 6 Responses Apr 28

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    Just posted some new pics.

    Let me know what you think ;-)
    JessicainNH JessicainNH 46-50, M 3 Responses Jun 24

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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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    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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    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 16 Responses Jan 21

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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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    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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    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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    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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    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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    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 22-25, T 6 Responses Jul 23, 2014

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    The first and only person

    that i have ever told, and possibly the only person to ever catch me dressed in panties.I was in Anatomy class one day with my good friend. Her and I were in the back of the class trying not to fall asleep. All of the sudden I get the urge to tell her about my secret. I don...
    banannasplitz09 banannasplitz09 22-25, M 3 Responses Jun 9

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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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    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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    And have been that way my entire life.

    Funny thing is, I only feel like a cross dresser when I'm wearing men's clothes. 😀
    BoyNbraNpanties BoyNbraNpanties 26-30, M 4 Responses Aug 3

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    It's a dang shame. I dress up

    whenever I get a chance .Last night I had the house to myself, but I was so tired that all I did was take a shower and put on a bra and panties to sleep in. I missed a great chance to enjoy myself.
    mandywantsit mandywantsit 51-55, M 8 Responses Jul 29

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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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    Went out for the first time dressed

    as a woman. It was very exciting but also scare wish I had done it long time ago
    Lonely47 Lonely47 66-70, T 1 Response 1 day ago

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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 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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     so I decided to put on my maid outfit

    with my new heels, what do you think guys and galls? ;)
    billy1710 billy1710 22-25 3 Responses Jun 11

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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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    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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    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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    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 15 Responses Jul 31, 2011

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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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    It makes me happy that,

    yes I may have a blanket slightly covering my legs, but I am sitting in easy view of my neighbours, while wearing leggings, a thong and a hood less sweatshirt while watching the rainstorm and scrolling through EP. I told myself to do it and here I am :)
    deleted deleted 26-30 2 Responses Aug 3

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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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    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 12 Responses Nov 20, 2014

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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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    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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    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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    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 65 Responses Feb 5, 2008

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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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    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 1 Response Apr 19

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    I start every day by dressing in hosiery

    and heels with a pretty chemise.
    Plugslave Plugslave 31-35 5 Responses Jun 10

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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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    It is a sad day. My wife has requested

    that I retire Terrieann permanently. It is a difficult thing to do, she has been a part of me for as long as I can remember and has helped me through difficult stressful times. I'm not sure I can really do this, but out of respect for my wife I feel I must try. Many thanks to...
    ta61 ta61 51-55, T 6 Responses 5 days ago