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I Like to Crossdress

Personal Stories, Advice, and Support 1,166 People

    DildoSniper DildoSniper 18-21, M Sep 24

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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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    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 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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    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

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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 18-21, M 3 Responses Sep 21

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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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    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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    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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    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'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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    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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    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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    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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    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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    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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    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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    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'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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    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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    fercrox fercrox 46-50, M 2 Responses Apr 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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    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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    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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    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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    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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    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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    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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    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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    marcus15 marcus15 16-17, M 2 Responses Jun 3

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

    for more teens into this
    SCARFACEkyle SCARFACEkyle 18-21, M 2 Responses Apr 24

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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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    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 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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    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

    Are there any girls from New Jersey that like crossdressers? I'd love to hear from someone and chat
    Lovethembig Lovethembig 18-21, M 1 Response Sep 28

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    If you're a girl that likes crossdressers you are automatically cool in my book. Y'all are the best!
    rachelmarie13 rachelmarie13 18-21, T 3 Responses Sep 28

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    I have always loved the ladies, even when I was the shy guy. Now, recently, I have been delving into crossdressing- clothing, makeup, and all. There is something surprising I have...
    MollyPetal MollyPetal 41-45, T 3 Responses Sep 22

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    Wanted to go shopping while crossdressed with my Mother, However since we lived in a smaller town she was afraid we would run into someone we knew. Then one weekend we had to go to...
    Stephaniegirl226 Stephaniegirl226 36-40, M 8 Responses Sep 23

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    I enjoy crossdressing. Right now I am dressed in a nicely fitting black dress, wig, heels and makeup. There is not a thing that I am wearing that is not feminine and I feel good...
    juliemarie2 juliemarie2 61-65, M 1 Response Oct 12

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    I be want to meet someone special the like to be with a crossdresser male or female I haven't had any experience with no one I want someone to training me
    vicky994 vicky994 36-40, M 1 Response 4 days ago

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      Just wondering if there are any girls out there that want to chat with a crossdresser in the uk. Nikki x
    Nikki1988x Nikki1988x 22-25, T 1 Response Sep 21

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    And if any would like to chat i am just a message away :)
    klgfrtf1345 klgfrtf1345 18-21, M 4 days ago

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    rate me guys?(: by the way that is me! I love wearing girls clothes and getting attention(: thanks!
    sissyboylovescock sissyboylovescock 16-17, M 11 Responses Sep 27

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    Any cute CD's that want to chat???
    SteelNettt SteelNettt 18-21, M Sep 29

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    As a confirmed sissy, tranny queer I love women who are into trannies. I often try women's clothes on when shopping, it is embarrassing "coming out" to strangers but some are...
    Jimhes Jimhes 31-35, M Sep 30

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    I have been a cross dresser my entire life and I indulge in my hobby whenever possible, much to my wife's disapproval. We have been married 41 years and my biggest mistake was not...
    MCTV MCTV 61-65, M 1 Response Oct 11

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    I'm in my slutty panties and lipstick I hope I can please someone through chat I'm on my knees and ready
    Yyntnt80 Yyntnt80 46-50, M 1 Response 23 hrs ago

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    Any crossdressers wanna talk?
    PlusSizeLover12 PlusSizeLover12 16-17, M 2 Responses 4 hrs ago

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    I'm an European boy, not a "teen" anymore since I've already turned 20, but I think this is the best group to post my story. Crossdressing has been part of me since I was 13, and...
    Eurocd Eurocd 18-21, M 1 Response Oct 10

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