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I Crossdress

Personal Stories, Advice, and Support 1,513 People

    Born Into Cross Dressing

     I recall my first cross dressing experience as a kid when my sister would dress me up. i had 4 sisters no brothers. ive never really liked having a penis and always felt so sexy in girls clothes. I used to steal skirts from op shops. and id wear them in the dark on the...
    love2wearskirts love2wearskirts 26-30, T 4 Responses Sep 24, 2009

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    Cd **** For Older Men

    Once i slip on my stockings, panties, heals, mini and top. Davina appears. Davina is a very naughty but fun CD ****. Davina first dressed for a stranger, a older male in public toilets for him to treat as a naughty girl. She then got hooked on dressing, being in public places...
    dirtydavina dirtydavina 36-40, M 1 Response Jun 30, 2011

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    Yes I Do

    I really don't like to call it crossdressing, but by definition that is what I do.Why is it, that since I enjoy wearing lingerie, that it has to have to a "label"? Why can't it just be a person wearing clothes?Female clothing has a much wider choice of colors, fabrics and style...
    happilymarriedguy happilymarriedguy 51-55, M Dec 16, 2012

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    In My Sister's Pantyhose

    the first time i ever put on my sister's pantyhose,i was 5. i did it often until i got caught. stop doing it until i was 12,by then i had alot more to chose from,i would wear them every chance i got.I have 5 sister's only one knows i still wear pantyhose
    philmaria philmaria 41-45, M 3 Responses Nov 6, 2007

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    Finally!!

    I have been crossdressing in the closet my. Whole life. (Well as much as I can remember). Always in secret and alone. I'm 35 now and have finally found someone. To share my passion with. What a freeing experience! She loves how I look and I love how it feels to dress with someone...
    lovestocrossdress lovestocrossdress 36-40 3 Responses Mar 22, 2013

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    I Do It Everyday

    I crossdress everyday. There is nothing that feels better than being in the soft and sensuous clothes that women get to wear. I love the freedom and coolness of a skirt that is full and freely moving around me. Plus the feeling as it brushes my legs. I so much love dressing this...
    Adam59 Adam59 56-60, M 3 Responses Feb 28, 2013

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    An Experience to Remember

    I started crossdressing at a very young age, trying on my sister's clothes. Eventually, around the age of fourteen I began trying on my mothers clothes, and even buying my own first pair of pantyhose. At sixteen I started dating girls, but the girl I remember most, I dated when I...
    Jenisa Jenisa 46-50, T 7 Responses May 25, 2008

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    My Son Wants To Start Crossdressing

    Hello everyone i need some advice i am single mom of a 13 year old son.I found him the about a month ago and caught him with one of my bras on.So of course he started to cry and telling me he was sorry .I told him there was nothing to be sorry about it .So we sat down and had a...
    Proudmom2000 Proudmom2000 26-30, F 3 Responses Aug 25, 2013

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    last week i bought my first female cloths.

    i ordered a garter and some matching panties and bra along with some big lace top thigh highs. i am so glad i did. wow. so sexy. i also ordered some 6in stilettos. when those come in my greatest fantasy will take place. i cant wait
    Zoe24 Zoe24 22-25, M 3 Responses Mar 20

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    This morning I decided to wear a bra

    and my falsies under my shirt when I went out for coffee. I also put on a rather dainty necklace as well as my favorite charm bracelet. It is cold here in Connecticut so I wore a light jacket which helped hide my bust though I did not wear the jacket while in my car. I...
    SevenFox SevenFox 36-40, T 5 Responses Dec 28, 2013

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    Hi I Am Guy Always Loved Femme Smoking While Dressed Always Found It Very Sexy, Wad Wondering If Anyone Else Out There Did Also

    Tell me your experiences and what you like, I have trouble finding other similar people
    frenchinhale frenchinhale 41-45, M 2 Responses Oct 23, 2013

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    Is it wrong for a straight guy to be curious

    about transgender women mtf?
    Crockhogan78 Crockhogan78 31-35, M 3 Responses Mar 12

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    how and why

    it all started when i was about 15. i had a beautiful girlfriend who was very feminine and always wore flowing skirts and heels. i loved it when her skirts laid over me when we sat together or cuddled. i finally plucked up enough courage to ask her if i could try one on and after...
    capeme capeme 46-50, M 9 Responses Nov 11, 2009

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    The Peephole

    My experience as a crossdresser began quite early in my life. I was 9 at the time. I remember we lived in a mobile home, and my room was next to my sisters. One night as I was playing in my room, I noticed a small hole in the wall and a light comming through. it probably happened...
    MsMarcy MsMarcy 41-45 1 Response Jan 2, 2013

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    Cross dressing youth

    Well it all started when I was little my step sister used to put nail polish on me and I hated it at first and then loved it and my Freshmen year is when I found out I like to cross dress I love wearing dresses, cheerleading uniforms, bras, nail polish and other make ups but it...
    Thecrossdresser Thecrossdresser 18-21, M 4 Responses May 21, 2011

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    How it all started:  I got interested in

    cross-dressing and scat many years ago when I was around twelve. I was delivering newspapers one early morning on the day that trash was out for pick-up. I noticed a bag that had turned over and some **** magazines had spilled out. I scooped up the whole bag and took it home...
    deleted deleted 26-30 3 Responses Dec 12, 2013

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    I Crossdress Because Thats Who Iam

    Iam a crossdresser thats who i am Iam not a woman but i love dressing up and transforming in to one. I dont know why i have this desire but i know that I love it . The feeling i get when i start to transform is so special I know its apart of me , just the thought of choosing my...
    hornydevil2710 hornydevil2710 36-40 Nov 15, 2012

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    Thank You Sisters

    at the age of 5 my sisters that are twins put stockings on me, and have never looked back, now 59 came out to my wife last year, she is ok with it so now get to wear every day, most of the time just seamed stockings and high heels, and a slip or skirt, sometimes go all out and...
    junita1954 junita1954 56-60 Aug 11, 2013

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    I have been crossdressing on

    and off for over 20 years now and although I have not dressed for over 2 years now. I can't help but being drawn back in to it. I have even thought about transitioning mtf. I told my partner about my dressing after we got back together again 3 years ago. She accepts it but doesn...
    Crockhogan78 Crockhogan78 31-35, M 1 Response Mar 11

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    Self Served

    I was dressed and feeling horny. I tired to ignore it and started to do some cleaning around the house. First, I did some dusting, then vacuuming. I was getting a lot done and making some progress. I don't know what cam over me, but I pulled up my skirt and...
    bicleveland bicleveland 36-40, M 4 Responses Mar 2, 2009

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    I Started

    I started whe I was 14   and found some older clothes belonging to my Dad's live in girl friend in our basement.  Started sneaking down late at night trying them on.  Now 28 years later I have a whole room full of clothes, wigs, shoes, and 2 sizes of silacone...
    Kara66tv Kara66tv 41-45, M 7 Responses Mar 22, 2008

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    My Son ....

    My son is now just 13, he has ADHD and has the mental growth of a 9-10 year old, I am pretty sure he is starting his change to young manhood, He has always taken my clothes, i think he was 3 when i noticed, but as all kids want to dress up....well here we are 10 years later and...
    ilovekisses ilovekisses 36-40, F 6 Responses Sep 23, 2009

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    Grocery Shopping Is Fun In A Skirt!

    I love going grocerry shopping in my skirts, and I'm lucky to have a nearby store where I can do it. I went again this morning in a bright white short Merona skirt (from Target), my pink soft Merona t-shirt and a dark wine-colored wrap, wearing my Great Northwest Clothing...
    JaxSkirtz1 JaxSkirtz1 56-60, M 7 Responses May 24, 2011

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    First Time Caught By Family

    I know I already wrote a story about my first time getting caught. The thing is that was for getting caught at school. This is the story of getting caught by family, fyi I was in a different town in this one do that is why I didn't count the getting caught at school in the first...
    richardthomas richardthomas 18-21 2 Responses Mar 24, 2009

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    I have been dressing in female clothing

    since I was in my teens, I do not go out in public like this though. I like how it makes me feel pretty. Even though the reality is not that. Inside I see myself as a woman , I know I will never be female. I also know there is not much I can do to look female either due to the...
    SevenFox SevenFox 36-40, T 1 Response Dec 27, 2013

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    My Wonderful Day

    Yesterday morning was a wonderful day. I got up and put on my new dress. It is a short dress, black with flower pattern. I drove to a local park to check out whats happening and sucked a older gentlemen's ****. After this I drove to a gas station to get gas. Then I went to...
    meg1cdforyou meg1cdforyou 61-65, M 3 Responses Aug 1, 2012

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    Closet Crossdresser Need Help!!

    Hi gurls so I´m a closet Cd, I´m Bi and have a girlfriend she´s very accepting. The thing is I dont know how much she lets me wear short shorts and panties from Victorias Secret. I wan´t to take it to the next level and thought about Palazzo flow pants (link below). I have...
    feraf87 feraf87 26-30, M Nov 5, 2013

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    So a few weeks ago I wore some tight pants

    and a belly shirt out in public without a sweater to cover myself and I felt so exposed lol but it felt nice, but I guess it didn't look nice according to people's expressions o.o
    navel795 navel795 18-21, M 2 Responses Feb 1

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    In Public

    My wife is responsible for my interest in crossdressing. It was her fantasy we were playing the first time I dressed up and after that first time I was hooked. I don't dress "en femme" all the time, but I do dress and it is great. My wife and I even go shopping together. She...
    km44 km44 61-65, M 1 Response Apr 16, 2013

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    Crossdressing

    I have not been crossdressing for very long. My wife introduced me to crossdressing. It was such a turn on that it has become a regular part of our lives. I go to the mall as my wife's best girlfriend. We look at clothes and try them on. I find things I think she would look sexy...
    km44 km44 61-65, M 4 Responses Mar 11, 2013

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    My First Trucker

    I was crossdressed wearing a short flowered dress on my way to a park that has some *********** available once in awhile. On the road on the way in I passed a truck and he blew his horn. He followed me into the park. I arked my car. He turned around an blew his horn again and...
    meg1cdforyou meg1cdforyou 61-65, M 5 Responses Jul 31, 2012

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    Kik

    does anyone wanna kik me @mkw3 any tg cd ladyboy
    mkw007 mkw007 18-21, M Jul 29, 2013

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    Was Marsha...now Marcy

    Just wanted to let my EP friends that I'm back to share more experiences and pics with my lovely friends. I was "Marsha". I have been calming down somewhat with pushing for more cross dressing in front of my wife. I always wear my panties, which after five years, still feels...
    1amMarcy 1amMarcy 51-55, M 20 Responses Aug 20, 2011

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    My Crossdressing Story

    I have just joined so, I would like to introduce myself. My female moniker is Molly, but as you can tell I was not born with that name. Here is my story. Like most of you I was fasinated with my mothers clothes from an early age I would try on her stockings I did not understand...
    mpenner mpenner 51-55 Aug 27, 2012

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    Look Mommie, It's Barbie!

    One of my favorite past experiences happened when I was shopping enfemme at a department store. It was on of the first times I had shaved my legs and I was wearing a short denim skirt with a white floral top with my new "feathered" below shoulder length wig. I had...
    kathielynne kathielynne 41-45, T 2 Responses Sep 18, 2009

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    I Cross Dress

    Last weekend I went shopping at Catherines. I had completed a survey about a recent shopping trip and was sent a coupon for ten dollars off a purchase. I wanted to use the coupon before it expired. After looking around the store I found a sleeveless maxi dress in a brown and...
    jml2000 jml2000 56-60, M Jul 5, 2013

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    Caught At School

    The first time I got caught crossdressing I was in fourth grade I was changing into my gym clothes and I forgot I was wearing panties and a dress that day under my jeans and shirt. When I was either crossdressing or wearing diapers on a gym day I always changed in the stall but...
    richardthomas richardthomas 18-21 3 Responses Mar 13, 2009

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    For everyone who enjoyed my other stories of

    crossdressing I'm going to have a new story soon. I'm house sitting for 9 days for a super hot 23 year old chick and her husband. I can't wait to explore her cloths and lingerie. It's gonna be so hot and I can't wait to tell you guys here at EP about it :)
    Zoe24 Zoe24 22-25, M 1 Response Apr 7

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    CD 4 BBC

    Hi! I dress sometimes in my own home. Turns me on. I have a girlfriend and she doesn't know my fetish. I hear story's of black men and how endowed they are and white girls think there amazing in bed. Well, I'd like to find out for myself. Just need to find a BBC man to handle me...
    FemBoie FemBoie 31-35, M May 21, 2013

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    I cross dressed, but not any more

    I arrived at my current lifestyle by trying on my sisters clothes as a young boy.  I knew then that I was not like other boys. When I was dressed in skirts and blouses, or even a simple dress I felt quite secure and natural. At...
    Micayla Micayla 61-65, F 2 Responses Aug 15, 2008

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    Mr.Prom Queen

    Tomorrow at my school my friends are dressing me up in a dress, leggings, heels and a thong! I will have to walk around openly for my school all day! I'm going to be in heaven!
    deleted deleted 26-30 2 Responses Mar 21, 2013

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    I Need Some Advice

    Hello all I need some advice I am a 25 year old cross dresser .I decide to have my hair done in a female style .I decided to have a wash and set at a salon .I am a kind of nervous and my sister and a female friend of mine wants to go with me for support.My sister also wants to...
    crossdressingjenn crossdressingjenn 22-25, F 3 Responses Oct 15, 2013

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    My Favorite Outfit

    As far back as I can remember, playing "dress up" has always been exciting and relaxing to me, but the best night was when I finally bought exactly the outfit I always wanted. Each piece was purchased at a different time, and I knew what the final look was going to be...
    Fezwick Fezwick 31-35, M 3 Responses Dec 15, 2006

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    My First Time As A Woman (Crossdressing)

    I'm a crossdresser since I turned 14. Back then I was "borrowing" my moms lingerie and dresses all the time when nobody was at home. I started out pretty innocent, but since that time the girl in me evolved a lot. I love to dress up as a complete woman including a wig, makeup...
    nathalie69 nathalie69 26-30, F 5 Responses Nov 1, 2012

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    I Enjoy It..

    Been dressing up for some years, I do enjoy the feeling of the lace and satin against my skin, depending on the mood determines what out fit that I am going to wear that particular day, I even wear my stockings and panties to my doctor visits, probably will go shopping again this...
    imcrater imcrater 46-50, M 3 Responses Apr 25, 2013

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    It All Started With Tights

    "I cross-dress" it all started when i was very young and for some reason loved seeing women's legs in tights. I envied my sister when she got to go to school wearing tights, but didn't know why. About age 8 or 9, i tried on a pair if my sisters ballet tights and was instantly...
    SaskiaIreland SaskiaIreland 31-35, M 10 Responses May 9, 2009

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    Every Day

    atleast in panties, often in much more, i wear panties of some sort 24/7, luckyli my wife loves it and is totally supportive, so i have a big load of lingerie and clothes, i like that i can change whenever i wan't and allways find something i haven't used for a while
    bodylower bodylower 31-35, M Jul 29, 2013

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    Just Started and Loving It

    I was over at my best friend's house helping her pack for her trip to queensland. She was going to some distant relative's funeral. We have been best friends since primary school. Her mum was at work, it was just the two of us. She had all her clothes laid out on her bed. She...
    Maddycd Maddycd 16-17 9 Responses Aug 12, 2008

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    I Still Love It.

    Started wearing my mum's things when I was 11 or 12. Love the old "Living Girdles." Then found out about tights, boots, bras. Even ventured out in the front yard when no one was home. Bondage came next. Once dressed in bright-red tights, bra, girdle, black boots...
    kakomitsumi kakomitsumi 56-60, M Jan 9, 2008

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    Related Experiences

    I want to be open as a crossdresser and part of a female group of friends or crossdressers
    Jess967 Jess967 18-21, M 1 hr ago

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    I've always loved the idea of dating a crossdresser. I'm what some people might call a "tomboy" and I just always found the juxtaposition ( I that's the right word I'm not really...
    BrahmaDonna BrahmaDonna 22-25, F 16 Responses Mar 22

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    I am falling for a crossdresser. I love him and who he is and I would never change him. I told my family, which consist of my mother and sister. Mom was accepting, my sister was...
    bbsw1963 bbsw1963 46-50, F 2 Responses Mar 24

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    Ok this is my first time writing about this and I am nervous about doing so. Ok i have crossdressed for as far back as I remember. The first time I can recall was at the age of 4...
    deleted deleted 26-30 4 Responses Apr 6

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    Um... Hi im a aspiring crossdresser Id kinda like help crossdressing if anyone would want to My kick is josef3303664
    deathtrap12 deathtrap12 18-21, M 3 Responses Apr 13

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    I love wearing girls clothes the more girly the better. I'd love to chat to other crossdressers so send me a message :)
    deleted deleted 26-30 1 Response Mar 25

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    I crossdress every chance I get. My wife knows but does not participate.
    cdtommy cdtommy 66-70, M 2 Responses Mar 28

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