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I Am a Crossdresser

Personal Stories, Advice, and Support 5,148 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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    The Real Me

    Hi im a 3o yr old crossdressing male *****. ive been dressing in womens clothes since i was 12, but i had always liked girl clothes better than boy stuff ever since i can remember. It all started cause my mother would have me help her pick out what she would wear each day, and it...
    nathaliajames4872 nathaliajames4872 26-30 3 Responses Nov 22, 2013

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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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    This is a little collection of some REALLY

    DIRTY STORIES that I've experienced between the age of 8~14. Some of these stories mind sound a bit too "sick" to our adult standards but back in the child's world there were merely an exciting harmless game. I feel many people might think this is my imagination and the pictures...
    CDJasmine CDJasmine 22-25 3 Responses Jan 2

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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 6 Responses Mar 2

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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 13 Responses Oct 23, 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 15 Responses May 21, 2013

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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 9 Responses Dec 18, 2012

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    A Relaxing Evening

    Just relaxing tonight and enjoying the feel of my new pink ballerina slippers that I picked up wal-mart, sitting here in my nightgown and finishing my nails.Buffing my nails to get a nice shine and clear polish, finally got all the pink polish off since last time, wonder if any...
    Joann62 Joann62 61-65, M 2 Responses Dec 1, 2013

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    cdjo cdjo 41-45, M Feb 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 27 Responses Mar 15, 2011

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    Got a couple new photos up with my face

    and makeup. What do you think? Do I look sexy and passable?
    Crossdresser15asian Crossdresser15asian 18-21, T 3 Responses Feb 20

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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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    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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    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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    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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    The Life And Times Of Isabella Regaldo Prt: 1

    For awhile I had thought of what it'd be like to be a girl. It's something that I've been thinking about almost since childhood. I vaguely remember at the age of four, attempting to wear my sisters clothing. I'm not sure if I was ever caught as I only have a fuzzy memory of this...
    IsabellaRegaldo IsabellaRegaldo 18-21, T 8 Responses Dec 6, 2012

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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 14 Responses Apr 22, 2012

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    Beginning my transition: I came out to parents

    and friends in October of last year that I wanted to become Lucy full time and make the transition. It was the most stressful time of my life and I still can't believe I actually did it but wouldn't change it for the world now. I have lost a number of friends by my wonderful...
    LucyTG LucyTG 26-30, T 3 Responses Feb 18

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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 21 Responses May 6, 2013

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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 24 Responses Oct 20, 2012

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    I love to shopping and dressing in women's

    clothes. It is such a thrilling and a rush. In can't pinpoint what I like the most. Could it be the nylon and heels. Could it be the matching bra and panties. Maybe it is the dresses and skirts.
    cdjo cdjo 41-45, M 4 Responses Jan 5

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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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    biggbaddy biggbaddy 22-25, M 3 Responses Jan 14

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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 12 Responses Dec 2, 2012

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    Surprise surprise. ..

    . I had a meeting to attend yesterday in Des Moines IA. It was just in the afternoon so I drove up and back the same day. I got dressed in my man clothes but put on panties and thigh highs. The plan was to wear a pair of heels to drive to and from the meeting. I left the...
    cdjo cdjo 41-45, M 4 Responses Apr 15

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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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    have been an (on & off) cd

    since i was very young (8 or 9), starting with my moms lingerie, going over stealing classmates to buying myself, purging several times as most cd's i here, but then i met my wife and over the years she has accepted my dressing and i now wear atleast lingerie everyday, i am a...
    bodylower bodylower 31-35, M 4 Responses Mar 16

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    So here I am just reading stories

    and feel so comfortable I started cross dressing this year and been a new experience for me everything from accepting myself to what size I am to what color I like to I like to shop shoes mostly, I love flats and I love getting new bathing suits too well I just wanted to say it...
    Curiouseone Curiouseone 22-25, M 8 Responses Dec 21, 2013

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    As i was finishing cleaning up

    after dinner my wife told me we must talk. I did"nt know what i did wrong. After i was finished i sat next to her and she told me to get each of us a glass of wine. I felt a little relieved now. I brought back the wine we each took a sip. She than told me that she was pondering...
    lindabo99 lindabo99 56-60, T 5 Responses Dec 31, 2013

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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 6 Responses Dec 30, 2013

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    Yes, I am a crossdresser.

    That's not what this story is about, regretably. Or perhaps it is? I just posted this in I Want to Improve the Experience Project. But I also wanted to give fair warning to everyone of the latest good tidings from EP Admin. I just received another "wonderful" email from EP...
    Kim1girl Kim1girl 56-60, T 13 Responses Mar 20

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    I am a crossdresser,

    and I would love to dress up as a woman whenever I want to. But as most crossdressers, I need to take care whenever I crossdress because of the neighboors, family, children, friends, the society in general, and of course my wife. When I first came out and confessed my...
    thereseNorway thereseNorway 36-40 5 Responses Feb 24

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    Hello... I've been wanting to share my story.

    .. I am 25 male.. Been working full time since i was 16.. I am a mechanic and an ordinary man or so everyone would think... I have been crossdressing in secret for 14 years or so.. I started when i realised i really love the feeling of tight clothes... I used to wear my sister's...
    ericasecretcd ericasecretcd 22-25, M 4 Responses Dec 19, 2013

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    Embrace It

    i have been dressing in girls and womens clothes since i was about 4 or 5 yrs old. i am now 46 and i love it. i have lots of really beautiful lingerie, all silks and satins and lace and i love wearing black nylon stockings. i used to be so confused and conflicted by my...
    xdresser9 xdresser9 46-50, M 10 Responses Apr 5, 2011

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    Hey, ive been doing this

    for a while, but never with someone else. I really want to, if anyone else in NYC does, please message me.
    mangera mangera 22-25, M Apr 9

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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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    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 10 Responses Mar 2, 2008

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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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    Hi, My name is Lilly.

    I was wondering if I could get some advice re wardrobe. My chest is 36 and my waist is 31. I've been looking at picking up a pair of velvet or velour pants a pair of Black leather or faux leather pants and some bell sleeve blouses. I feel like I might be almost ready to try...
    Lilly292 Lilly292 41-45 4 Responses Jan 5

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    New Years party and an old ***.

    I was at a small New Years party at a friends house. Amung the people at this party were friends that I have mentioned in some of my previous stories. There were also two friends that I haven't seen for a long time. One for 15 years, the other nearer 20 years. One of these old...
    Heellover Heellover 36-40, M 3 Responses Jan 3

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    Repair Mans Visit

    Today :) Today, Mother left me in to wait for the repair man whilst she went to work. Typical! A whole day in on my own that I could use to be En Femme without any worries of anyone interrupting me, and she has to get a repair man in! Oh well, I think, knowing that likely he'll...
    Heyyoitsjo Heyyoitsjo 26-30, T 14 Responses Nov 29, 2011

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    Be Who You Are

    I started dressing by wearing my sisters clothes when I was 7. would get dressed whenever I was home by myself. I have dressed on and off since then. The older I get the move I feel free to dress as I want.The feeling of dressing in public and being who you are is immense.
    juliecd juliecd 56-60, M 13 Responses Oct 4, 2007

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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 27 Responses Mar 27, 2012

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    So I've been on this site before

    but deleted my account before. Now I'm back! Been cross dressing only for a few months (since summer) but just seem to love it. Doing it as I type :) Just love feeling feminine and sexy but my biggest joy is that I turn on people looking like a girl. The open deception is...
    idk137 idk137 22-25, M 4 Responses Dec 31, 2013

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    Today I have the whole house to myself with no

    one it! So I get to dress up like a girl completely! just uploaded more pics go check them out!
    mrman77 mrman77 22-25, M 3 Responses Apr 4

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    I've loved dressing as a woman

    since my early teens. I love all sorts of feminine clothes, lingerie, nighties, pretty dresses and rainwear. When I'm dressed I'm very submissive and I love the feeling of turning on guys. Sadly I've never been truly convincing - I'd love to be able to go out and about dressed...
    rosemaryflowers rosemaryflowers 51-55, T 5 Responses 2 days ago

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    mrman77 mrman77 22-25, M Mar 5

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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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    My Love Of Crossdressing

    Since I began crossdressing all those years ago, it is forever on my mind. When I'm walking down the street and see women beautifully dressed, I want to run home and slip in to a dress, tights and heels. Anywhere I go I'm constantly wanting to dress and when out with my group of...
    LucyTG LucyTG 26-30, T 14 Responses Mar 1, 2013

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    My Mistress has me wearing garters

    and stockings almost exclusively now, and I have been allowed to wear my little black dress more often now too. I love wearing my high heels as often as I can, and I just adore how my pretty feet look with Go-Go Girl red on my toes ; )
    Plugslave Plugslave 31-35 4 Responses Mar 4

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    I had a meeting with HR

    and my manager today about transitioning from male to female in the near future. My gender clinic appointment is in April and I want to start my Real Life Experience as soon as possible. HR will be holding a meeting with my colleagues soon and we have agreed for me to come to...
    LucyTG LucyTG 26-30, T 9 Responses Mar 10

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    I love prancing around in my skater dress,

    pumps and tights. Have a look at my new photo album.
    sensuousPH sensuousPH 41-45, M 6 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 17 Responses Apr 18, 2013

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    Crossdressing for Christmas This Christmas I

    am staying home and crossdressing full time for a few days. I went out for the last few needed items yesterday. After that I got changed when I got home. Today I woke up, had my morning coffee, then went for a soak in the tub and to shave my chest and legs. Then I laid back on...
    AnonymityDarkstone AnonymityDarkstone 31-35, T 2 Responses Dec 24, 2013

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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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    and have been for many years.

    I am married and have kept my crossdressing secret so only get to indulge about once a month but I spend a lot of my time thinking about it and on the internet reading or watching videos or in chat rooms (under my sissy persona).
    cdjanine cdjanine 41-45 4 Responses Mar 2

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