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I Like to Crossdress

Personal Stories, Advice, and Support 1,112 People

    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, T 8 Responses Apr 10

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    Last Summers Vacation

    I am a 56 years old, who has a wonderful wife that is supportive but careful about me cross-dressing. We call these outings. We have gone out together many times (shopping, dinner, sightseeing) mostly when out of town. I have cross dressed since my early teens. Last summer I had...
    clarame clarame 56-60, M 1 Response Apr 16, 2012

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    To-days Attire

    While I'm out shopping & using a computer in my local library I have on under my male clothing a bra & pantie set in red, red tights/pantyhose & a red summer dress 
    xdpaul xdpaul 56-60, M May 26, 2012

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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, T 4 Responses Apr 14

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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, T May 26

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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...
    Jedimindtrick39 Jedimindtrick39 36-40 8 Responses Oct 14, 2012

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    In A Relationship With A Much Older,muslim And Married Man

    it has been a month since we started dating before we dated he started courting me, 1st i was reluctant his a very hot handsome man,his 32 am 22.he never told me he had a wife before so we started dating he treats me well than other younger men,he made sure i fall inluv with him...
    toto1990 toto1990 22-25 Jul 26, 2012

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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, T 1 Response May 17

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    Any teens have a **** fet I'm looking

    for more teens into this
    SCARFACEkyle SCARFACEkyle 16-17, M 1 Response Apr 24

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    I've been cross dressing

    for a few years and I don't really remember how it began. I do remember that my first time involved a lace thong and not knowing how to put it on, but that's beside the point. I told someone for the first time just the other day. My friend (let's give her a pseudonym) Olivia...
    J3nni J3nni 26-30, F 3 Responses 1 day ago

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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, T 1 Response Apr 14

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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, T 3 Responses Apr 24

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    Can'T Stop Cd

    I love to cross dress my wife fond out and she wheat mad and kick me out had to promise I stop but I no I can't stop I hide my stuff when she is out I dress up then I don't no wort to do :(
    alistair1972 alistair1972 41-45, M Oct 2, 2013

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    marcus15 marcus15 18-21, M 2 Responses Jun 3

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    Crossdressing

    When I crossdress I feel like a woman, I get myself in a black skirt and tights followed with panties and bra that matches and a normal pink shirt with a girly jacket, My shoes are black leather boots which make me feel sexy wearing them and I love my wig and make up making me a...
    Bondageboy12 Bondageboy12 18-21, M Aug 21, 2013

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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, T 4 Responses May 1

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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 5 Responses Oct 4, 2011

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    Mexx

    My name is Mexx when I'm a lad. Basically I just started this 2 days ago when I dressed as a dude for a date, and when I showed my mates pictures of me as a boy they thought I was really fit and realistic! So soon I'll get my money and start getting some boys/men's clothes...
    h47hentahu7y5a h47hentahu7y5a 16-17, M 3 Responses Oct 1, 2013

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    An Outing With My Wife

    My wife and I call it and "outing " when I crossdress and we go out in public. Tonight, began preparation for tomorrow, by bleaching my hair on my wrists and doing my nails. My wife helped my pick out my outfit ( long black skirt with a white print along the bottom, a black...
    clarame clarame 56-60, M Apr 15, 2012

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    I Crossdress Too

    I love to dress as a girl from head to toe, i love putting on a bra and pair of panties and then putting pantyhose on over my panties and then a dress, then i put high heels on then i go outside and sit out front or in the backyard
    addguy3455 addguy3455 18-21, M Oct 3, 2011

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    I'm Bi And I Like To Dress As A Woman

    Well to start off I've always wanted to dress as a woman never had the guts for it till i thought to myself F*** It I'm doing this and see where it goes problem is I can't be out with my family otherwise I'd be out on the street so I am trying to find a place of my own so I wont...
    theshytype theshytype 36-40, M 1 Response Aug 26, 2011

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    The Beginning

    Like many of you, I started by wearing my mothers things. First it was her boots. I love boots to this day. Then I added pantyhose, then bras. That was pretty much it until after college, when I had my own money and started buying my own things. It has progressed alot since...
    tammibadger tammibadger 51-55 2 Responses Jan 4, 2013

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    I Love To Crossdress

    I love to crossdress.  I have been crossdressing for many years.  I started wearing mom's clothes when I was 12 or 13.  After outgrowing mom's clothes I started to buy my own women's clothes.  I's shop at church rummage stores and thrift stores to find things in larger sizes...
    jml2000 jml2000 56-60, M 1 Response Jun 20, 2012

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    I Like To Crossdress

    I shave my legs, make my face up real nice, get my stockins n heels, get a nice dress on and do my wig up a bit and go out. The sad thing is just drive around and never get out or go into the restaurant. All kinds of heads will turn at my some what attractive figure and this...
    AnnaisBell AnnaisBell 36-40 6 Responses Jan 16, 2011

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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, T 4 Responses Apr 15

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    Thrift Stores & More!

    I have been crossdressing for most of my life.  I can remember dressing fully from about 1975.  I have shaved my legs and chest in the past and dabbled with makeup from time to time, but long ago settled into lingerie, clothing, shoes, belts, wigs, jewelry and sometimes perfume...
    Falecia0 Falecia0 61-65 3 Responses Jul 22, 2012

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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

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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 5 Responses May 23

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    In A Relationship With A Much Older,muslim And Married Man

    it has been a month since we started dating before we dated he started courting me, 1st i was reluctant his a very hot handsome man,his 32 am 22.he never told me he had a wife before so we started dating he treats me well than other younger men,he made sure i fall inluv with him...
    toto1990 toto1990 22-25 Jul 26, 2012

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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
    Jedimindtrick39 Jedimindtrick39 36-40 3 Responses Jun 13, 2013

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    Can't wait to get home tonight

    but what to wear???? X
    xdresses xdresses 18-21, M 5 Responses Jun 21

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    fercrox fercrox 46-50, M 2 Responses Apr 6

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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

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    Wife accepts that I crossdress

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

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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, T 1 Response May 20

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    Nothing hurts me worse

    than being called an "it." People really suck sometimes.
    Stacy81 Stacy81 31-35, T 3 Responses May 20

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    Related Experiences

    I started crossdressing when I was around ten years old. Womens clothes just feel right on me. I liked crossdressing since the first time I wore my sisters bathing suit. It was...
    Jessica1967 Jessica1967 41-45, T 6 Responses Jun 26

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    well, yeah. basically, I have struggled with the crossdressing thing for some years. I don't go full out, makeup and dress out in public, I'm not that into it. Mainly just the...
    bigmacintosh22 bigmacintosh22 22-25, M 1 Response Jul 10

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    Well I do adore ladies who like crossdressers, but that's like, not the point. What I wanna say is - I'm a mtf trans (15) myself and I'd luv a bf who crossdresses, he may even...
    LindavdB LindavdB 13-15, T 5 Responses Jul 16

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    I am in Houston, Texas. I am looking for a woman who is interested in meeting and being with a crossdressing male. One who is interested in being friends first.
    jemmer01 jemmer01 46-50 1 Response Jul 13

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    I have been crossdressing since I was in my teens .over the years the compulsion to dress as a woman has intensified dramatically .i now dress completely with full make up and am...
    francescalewis1956 francescalewis1956 56-60, M 1 Response 2 days ago

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    Hi are there any females to help me crossdress? I need help i want to have a girl(s) dress me up as a girl If your a girl reading this and your interested message me or comment...
    BDSMFan1 BDSMFan1 22-25, M 3 Responses 8 hrs ago

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    Hi! Not one myself, but I was wondering if any drag queens/crossdressers would want to discuss makeup?! <3 I need more tips and I'm willing to give some as well!
    JustCammy JustCammy 16-17, F 2 Responses 7 hrs ago

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    I would love to meet a girl that likes cross dressers. Message me girls/ladies!
    wjk1849 wjk1849 46-50, M 4 days ago

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    Hello,my name is jacob but i like to go by zoey. I have spent the last seventeen years of my life alone because I am a girly-boy. Now I have the Internet and sites like this...
    jmallon764 jmallon764 18-21, M 1 day ago

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    I'm looking for a woman in socal (805 area code). I'm easy going nice and I love to shop :). I also live in Simi valley
    lauraCD805 lauraCD805 36-40, T 1 Response Jun 30

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    Every since i was made to out on a pair of panties when I was young, as soon as those panties were on I was hooked. And its all I've been wearing since
    Victoriacrossdresser Victoriacrossdresser 26-30, M 4 Responses 1 day ago

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    Sooo, tonight for some reason everybody seems to be calling me or texting me and talking about work things and such. All manly man stuff, but what none of them realize is I've...
    JessicaCD20 JessicaCD20 18-21, M 2 Responses 10 hrs ago

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    I love crossdressers... and why. I always saw things from the girl's body, feeling like a boy point of view. It was natural for me to wonder about the other side, if there were any...
    DarkwingGoslyn DarkwingGoslyn 31-35 1 Response Jun 28

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    Sometimes people think that crossdressing automatically would make someone seem gay, but that isn't it! Crossdressing is just a thing that some men (or women) like to do! It makes...
    naco26withcheese naco26withcheese 13-15, M 1 Response 5 days ago

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    I've struggled with being a crossdresser all my life, and be Christian crossdresser for the last 21 years. When I was only a crossdresser I just though I was sick and something...
    DawnR59 DawnR59 51-55, T 7 Responses Jun 30

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