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I Like to Crossdress

Personal Stories, Advice, and Support 1,303 People

    I just... feel more comfortable wearing more

    feminine clothes I guess... I love how they look, and how they feel. Wearing a dress or a skirt or some makeup, always makes me feel so... so pretty. I love feeling pretty. I'm still pretty closet-ed about it all though in real life :s I wish I was strong enough to express...
    Madoka9 Madoka9 18-21, T 1 Response Oct 30, 2014

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    A Girl Underneath: I can't always be dressed

    up but when I can get away with it I dress femme under my male clothes. One of the best times I can recall is in my second year at university. I stopped over at a female friends house early before class and I needed to shower as I got there all sweaty (I had been running) so I...
    a3s1r a3s1r 26-30, T Feb 19, 2014

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    Can't wait to get home tonight

    but what to wear???? X
    xdresses xdresses 18-21, M 4 Responses Jun 21, 2014

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    I have just returned from my first "outing" .

    Mid day , grocery store . Although in a chicken hearted way lol . I dressed in my girliest panties , pantyhose , ladies jeans with white dress shirt and open back ladies shoes with a half inch heel . One would have to look very close to detect , however it was one of my hugest...
    MissMsSissy MissMsSissy 56-60, M 7 Responses Oct 6, 2014

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    I have long legs. I love to wear this type of

    strappy heel with a short skirt or dress.
    stamfordfan stamfordfan 41-45, M 1 Response Oct 30, 2014

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    I'm new on EP. I like the freedom it allows.

    Reminds me of walking in a park wearing a sundress and no undies. I kinda wanted the wind to blow my dress up just for a second.
    stamfordfan stamfordfan 41-45, M 1 Response Oct 29, 2014

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    I like to shop enfemme

    whenever I get the opportunity.This is a picture of me
    breannahenderson123 breannahenderson123 41-45 5 Responses Apr 4

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    Bought some jeans today

    and actually tried them on in the store for once. Really starting to get the hang of this. :)
    Stacy81 Stacy81 31-35, F 4 Responses Apr 15, 2014

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    I love the ritual of getting dressed

    for a night out. Lying in the bathtub and thinking of what to wear. A dress? A skirt? A suit? Very short? Knee length? Maxi? Dress with a slit? Skirt and jacket? Or with a blouse? Or a sweater? Do I want it to be tight or loose? With stockings? Thigh highs? Garter belt...
    stamfordfan stamfordfan 41-45, M 2 Responses Oct 29, 2014

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    Second time in public with all girl clothes.

    Same jeans and tshirt look, but went to a restaurant with a friend this time. Felt good, for sure. Trying to build up to short shorts since they're a hell of a lot more noticeable than jeans.
    Stacy81 Stacy81 31-35, F 4 Responses May 1, 2014

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    When ever I see an attractive woman in a

    skirt/dress I like I want to talk to her and tell her I'd like to try on her skirt/dress.
    stamfordfan stamfordfan 41-45, M 3 Responses Nov 1, 2014

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    Any crossdressers want to talk I woke up horny

    I don't know and I feel sexy
    yuyu0079 yuyu0079 18-21, M Apr 17

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    I love to crossdress.

    I have some panties and a bra. I wear a dress sometimes and I can sometimes get thongs and sexy panties from my cousins sister. I wear panties under my jeans and I sometimes wear them to school. I am straight but I love the feeling of them.
    Wedgiesinthongs Wedgiesinthongs 13-15, M 4 Responses May 23, 2014

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    Love It..

    Guys are so funny. I grew up with a bunch of bullies in school. They made my self esteem low. The funny part of it, I'm sure most of them would have fallen for me, if I was dress as a woman. Lol
    KatrinaBoyer41 KatrinaBoyer41 41-45 3 Responses Jun 13, 2013

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    As much as I love wearing a skirt,

    heels, and hose, I think I'm at my cutest when I'm wearing women's jeans, a pink/ purple hoodie, and pink sneakers. Makes me want to hug friends and bake them pies.
    Stacy81 Stacy81 31-35, F 1 Response Apr 14, 2014

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    Today sucked in every way.

    Got called all kinds up ****** things, workers at stores were rude, and my real life friends don't seem interested this time. It happens and it will pass, but days like today really hurt.
    Stacy81 Stacy81 31-35, F 1 Response May 20, 2014

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    Wife accepts that I crossdress

    and ****** me crazy
    Sophieflesh Sophieflesh 31-35, T 5 Responses May 6, 2014

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    I really like crossdressing everything

    that a women wears I like to wear its a turn on and it turns other people on just love hat
    lvrofhose lvrofhose 56-60, M Dec 2, 2014

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    I was in Victorias Secret a few years ago.

    I was a little nervous as I shopped for stockings and a skirt. When a sales lady asked if she could help I blurted out "What size skirt would I wear?" She smiled and showed me the selection. I found a pleated short skirt I liked. The sales lady asked me "Would you like to try it...
    stamfordfan stamfordfan 41-45, M 4 Responses Oct 29, 2014

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    I seldom wear long dresses.

    My fav skirt length is where I stand up, put my hands by my side, and wear a skirt that's just shy of my finger tip. Very short and sexy. If I'm going out without panties I'll wear something a little longer. I was in a taxi the other night with a cute dress and no undies. I...
    stamfordfan stamfordfan 41-45, M 3 Responses Oct 29, 2014

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    I Love Crossdressing

    I had some hanes her way cotton panties that fit my feminine *** perfectly. I put those on with thigh high stockings. After I wore a white lacy bra with inserts that gave me a nice B cup. After, I put on a black skirt and a black wig. With make up, I was very passable. I love...
    KikkiNikks KikkiNikks 26-30, T 4 Responses Oct 4, 2011

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    I love getting in and out of car

    when I'm wearing stockings, a short dress or skirt and heels. People don't look to see if you're a girl or a boy. They just love to look.
    stamfordfan stamfordfan 41-45, M 1 Response Oct 30, 2014

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    I am male but I like to dreas women stuff I

    should say I wear it very little coz no one accept but when I am not I keep dream about it
    girlyboy83 girlyboy83 31-35, T 1 Response Feb 13

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    Nothing hurts me worse

    than being called an "it." People really suck sometimes.
    Stacy81 Stacy81 31-35, F 2 Responses May 20, 2014

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    I can`t believe I was able to squeeze into

    these skinny jeans :PBut they are super comfy :D
    DildoSniper DildoSniper 22-25, M 3 Responses Sep 21, 2014

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    Where do attractive ladies find the time to get

    all "dolled up." It takes me forever to shave my legs, paint my nails, do my make up and choose jewelery. Never mind choosing type of underwear, dress, stockings and heels. But it's all worth it in the end when you walk out there and feel people's eyes on you as you sassay down...
    stamfordfan stamfordfan 41-45, M 1 Response Oct 30, 2014

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    I used to be terrified of buying women's

    clothing while shopping alone. I still feel some anxiety, but I can do it. I came up with a decent trick, though; maybe you can use it, too. If I start to panic, I turn off my phone, put it by my ear, and pretend there's a woman on the other end explaining what she wants me to...
    Stacy81 Stacy81 31-35, F 8 Responses Apr 10, 2014

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    DildoSniper DildoSniper 22-25, M Sep 24, 2014

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    I don't think of it as crossdressing really.

    I've felt like a girl for as long as I can remember. It's more like finally being able to wear things that other women are wearing.
    SandyBG SandyBG 56-60, T 2 Responses Nov 1, 2014

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    The only thing that keeps me from gaining

    weight is my desire to crossdress. I love very short, tight skirts. Nothing beats the looks you get when your legs are perfectly sculpted in stockings and heels. I love to sit on a couch and cross my legs. It took me forever to learn how to do it correctly.
    stamfordfan stamfordfan 41-45, M Oct 30, 2014

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    I love wearing women's clothing,

    it makes me feel super cute!
    gaykitten gaykitten 16-17 1 Response Dec 29, 2014

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    DildoSniper DildoSniper 22-25, M 1 Response Apr 10

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    Crossdressed And No Where To Go

    Wow, it's 4a.m. and I finally finish geting dress. Everybody is sleeping, I got the door lock. My girl friend is gone for the weekend. I made plans this whole weekend to be dressed and walk around the house looking sexy. I wanted to go for a ride, but my girl friend's cousin is...
    KatrinaBoyer41 KatrinaBoyer41 41-45 8 Responses Oct 14, 2012

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    Officially taking a break from being Lydia

    and dealing with my urges. I have huge exams coming up and i recently got a girlfriend so i need the time and energy for other things. I'll be back in a few months maybe, thankyou everyone. Goodbye for now :)
    LydiaCDRose LydiaCDRose 18-21, M 3 Responses Nov 1, 2014

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    Just bought some sandals

    and wedges and got a veteran discount. Don't see that every day!
    Stacy81 Stacy81 31-35, F May 26, 2014

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    Went out wearing nothing

    but girl clothes tonight. First time ever. Granted I was at a musical on a college campus, and I was wearing jeans instead of a dress. Still, baby steps!
    Stacy81 Stacy81 31-35, F 2 Responses Apr 24, 2014

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    stamfordfan stamfordfan 41-45, M Oct 29, 2014

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    I'm at a cocktail party.

    I'm dressed like a guy in boring pants and a boring white shirt. I keep looking at all the girls in their cute dresses, wishing I could join them. Sigh. (Nylons under my pants is the best I could do)
    Stacy81 Stacy81 31-35, F 4 Responses Apr 14, 2014

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    I'm to the point now

    where I don't feel awkward buying women's clothes anymore. The only time I felt out of place today was when I walked through the men's section.
    Stacy81 Stacy81 31-35, F May 17, 2014

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    Oh my, on my Facebook tonight,

    one of my friends put a picture on my wall of a girl and dude wearing short shorts(about 3 sizes too small, but that's not the point) then another friend was like "looks like she wears the pants; not him" then in brackets put (it) , I coulda ***** slapped him
    JessicaCD20 JessicaCD20 18-21, M 2 Responses May 28, 2014

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    Would love to talk to ladies

    who like straight men who love to crossdress.
    stamfordfan stamfordfan 41-45, M 1 Response Oct 30, 2014

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    JamieMostra JamieMostra 26-30, T Feb 19

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    Related Experiences

    I love crossdressing, but whenever I start, I get soo h0rny. I end up on my stomach like this.
    sexysubboy sexysubboy 18-21, M 1 Response Mar 31

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    Ok, so I'm not a girl, but the title is sort of appropriate for my story. So my girlfriend has known for a while now that I crossdress. I told her early last fall and she was...
    WalterStuart22 WalterStuart22 18-21, M 3 days ago

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    So it's becoming real. Im saving money for a bus that im going to turn into a mobile store for crossdressing. With mirrors, make up counter, racks of clothes, shoes, toys...
    newasexy newasexy 26-30, F 6 Responses Apr 14

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    I wish I could crossdressing all the time, but my wife would freak . I feel stifled.
    simonsteane simonsteane 46-50, M 5 Responses Apr 17

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