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I Like Wearing Dresses

Personal Stories, Advice, and Support 7,113 People

    I'm a 52 year old man

    and have been crossdressing since I was about 7. I would much rather wear a dress that pants and a belt. Like most men my age I've got a bit of a "belly" and am constantly pulling my pants up because they tend to slide down because of the belly. Who developed this anyway?? Oh...
    hotgarters hotgarters 46-50, M 5 Responses Apr 26

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    So Feminine And Alluring.

    I never wear trouser suits or jeans ever.I wear dresses or skirts all the time, the choice of fabrics and styles and colours is almost endless.The sexy look will never diminish and such wonderful lingerie can be worn under the dress or skirt.More girls should try dresses instead...
    pamela8 pamela8 66-70, F 12 Responses Nov 24, 2011

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    I Served As A Waitress

    I was asked to serve at a larger bussinesspart where I hardly knew anybody. I think the organisers thought it was kind of fun to have a crossdressing waitress.. I think it went well. I was welcomed and everybody who organised the party were wery friendly. I changed and gort help...
    Bea92 Bea92 41-45, M 10 Responses Oct 7, 2013

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    When I am going out I really like to dress up

    by wearing a nice dress, with thigh highs, and heels.
    christymclake christymclake 31-35, F 4 Responses May 7, 2014

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    I'm selling tons of adult baby clothes

    and a adult baby crib message me if your interested tons of girly dresses
    feedeeforyou feedeeforyou 18-21, F Jul 17

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    My first dress that I ever wore is still my

    absolute favorite dress! I was 12 years old and went into my parents room and into my mom's closet. There it was a beautiful white Mrs. Cleaver house dress. I put it on and twirled in it! I can hardly explain how great i felt in that dress. I would practice sitting very lady...
    deleted deleted 26-30 4 Responses Aug 29, 2014

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    Some believe a dress is impractical

    for the modern woman. I am of the other view, a dress is a statement of empowered femininity.
    Astrucbmt Astrucbmt 22-25, F 31 Responses Jul 23

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    I wear a dress as often

    as possible. It's such a free feeling. You don't have to wear underwear if it's not see thru. I love the way they look, especially the long ones that are back in style. Those long folded waisted patterned skirt w a t-shirts and casual heals. Dresses allow you to be cute and...
    Jennerrous Jennerrous 36-40, F 1 Response Aug 18, 2014

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    Im not the type of girl to wear dresses.

    But when i do, i surprise myself as well as others (in a good way) haha
    ninjadentistinspace ninjadentistinspace 16-17, F 1 Response Feb 1

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    My First Dress

    Hey, I am a boy, but I feel like a girl. That means I am Transgender, I don't have problems with that as long as I have the possibillity that I can dress like a girl. Today I got my very first dress, pantyhose, bra and mid. high boots with a small heel. My parents are very...
    JustMeTiffany JustMeTiffany 18-21, T 24 Responses Apr 20, 2013

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    My mom knows me so well!

    She came home with this dress for me<3
    Alliforevers Alliforevers 18-21, F 14 Responses May 21, 2014

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    deleted deleted 26-30 1 Response Jul 16

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    My Love For Dresses

    Ok so I love dresses but im a guy and how weird is it having a guy buy a dress that just so happens to be his size? Well I dont care what people think about me buying dresses. What they dont know will not hurt them. I buy and wear all kinds of fancy and casual dresses. I would...
    AdrianneJaye AdrianneJaye 22-25, T 35 Responses Mar 5, 2012

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    omg...... I live at home with my brothers

    and mum and I like wearing my school dress witch I brought online at home and no one knows I sometimes walk out in public wearing it and it so cool I love wearing them and no im straight I even wear it in front of my gf ive been wearing dresses since I was 6 years old no one in...
    imcool2002 imcool2002 13-15, M 2 Responses May 9

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    I love wearing a bra

    and panties, short dresses or short sundresses, thigh highs, or no hose at all, and either high heels or sandals when I am out too.
    dianefisher dianefisher 22-25, F 3 Responses Feb 1

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    My favorite dresses are maxi dresses Tight

    fitting or not. They are cute
    lorrena19 lorrena19 18-21, F 2 Responses Feb 2

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    Midi, Maxi And Short Dresses.

    I prefer wearing dresses as they offer far more freedom of movement and there is a dress suitable for all occasions, be it work related or a function or a formal event.Far better than trousers and also under a dress you can wear a full length Petticoat or a half slip, so...
    janeseymour janeseymour 22-25, F 40 Responses Jul 4, 2012

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    I love wearing dresses

    or sundresses or skirts and blouses when I am getting dressed up and going out. I always wear hose and high heels with my dress or skirt.
    redheadedfemale redheadedfemale 41-45, F 8 Responses Aug 20

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    I Love Wearing A Dress At The Weekend.

    The feeling is really good and most girls have forgotten the freedom a dress gives and wear jeans or trousers as every day wear.Remember how your Mother dressed you as a Girl, it was always dresses by the seasons, Summer dresses. Winter and Christmas Dresses, glide over your...
    demuremandy demuremandy 26-30, F 11 Responses Jan 10, 2012

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    I'm selling tons of adult baby clothes

    and a adult baby crib message me if your interested
    feedeeforyou feedeeforyou 18-21, F Jul 15

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    I love wearing short sundresses year round.

    I do not have any long pants but I do wear shorts and a bikini when out on the town. I do not wear any panties under my dresses ever. Even when wearing my Sunday dresses, I never wear panties to church. That is so hot as I sit in the first pew, with my family, and open my...
    redheadedfemale redheadedfemale 41-45, F 11 Responses a week ago

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    Mrskatearch Mrskatearch 31-35, F 11 Responses Jun 25

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    not like I love wearing them.

    the only problem I have is do to my body shape I have a problem getting one that fits on top that isn't to large at the waist and hem
    jamie172 jamie172 46-50, T 5 Responses Aug 9

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    One Sunday I wore a purple dress to church.

    It was nothing special but it looked nice. After church we went into the Commissary to get a few groceries. We were checking out when I noticed that the elderly gentleman bagging our groceries was a veteran. I walked told him intent on thanking him for his service when he looked...
    SweetMae SweetMae 61-65, F 48 Responses Mar 21, 2014

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    Because I am professionally employed,

    I must wear dresses or a skirt and a blouse at work. I actually love and enjoy dressing up when going out to other places. I always wear thigh highs and high heels too because I have long legs and my husband wants to show me off when we are out. Many times I do go commando...
    momoffivegirls momoffivegirls 36-40, F 6 Responses May 25, 2014

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    Not always. But sometimes I'd like to dress

    sexy. Tight short dresses are my favorite, some of them reveal my lingeries. (as you can see below) So I enjoy to see how peoples' react about me. I feel more attractive when I dress like this! And I work as part time bartender these days, I get much more tips when I wear...
    Canaria Canaria 22-25, F 55 Responses Apr 12

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    I love and enjoy wearing dresses.

    Besides I have long legs and want to show them off. If I wear pants, then my beautiful legs are hidden from view of others.
    amandahill amandahill 31-35, F 8 Responses Jun 8, 2014

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    I like wearing a beautiful dress with some

    heels. It makes me feel like a pretty lady.
    MsKristin MsKristin 18-21, F 4 Responses Mar 8

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    marebare303 marebare303 13-15, F 6 Responses Jul 31

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    Last night I went to a party.

    I went in my normal male drab, but took some clothes with me. I asked my wife if I could change into my dress. She said yes. So I went to the bathroom and took off all my male clothes. Put on a pair of black Wolford satin touch 20 tights, and a short glittery dress, a pair of...
    deleted deleted 26-30 11 Responses Feb 1

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    I love wearing dresses,

    they feel so much better than boring mens clothes. Slipping in to a nice dress feels so sexy, wish I could spend more time in them and head out full time :) Ah well that is what my future holds x
    GirlyLisaTG GirlyLisaTG 26-30, T 2 Responses Dec 29, 2014

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    Being A Girl For The Summer

    when i was 18 i was in a drum and bugle corp, back then they were every where. i was a solo soprano with sever corps through the years. i became friends with some girls in a rifle line of another corp and would hang out with them at there practices a lot and even started spinning...
    closet36 closet36 61-65, T 16 Responses May 7, 2012

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    I like to get up in the morning put on a bra

    for the day then a summer mini sundress. No pantie. it is so sexy feeling.
    serinalynn serinalynn 66-70, M 5 Responses Aug 26

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    I'm a guy but I like to wear dresses they are

    comfortable and nice tell me what you think
    changegender changegender 16-17, M Apr 22

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    I like wearing short dresses

    or mini skirts when doing out. I do not wear pants ever. I have long legs and prefer showing them off.
    computerbusinessmom computerbusinessmom 36-40, F 7 Responses Oct 24, 2014

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    I Wear Dresses Most Days.

    I do not know why so many girls permanently wear jeans and baggy jumpers, no glamour at all and some of these girls have nice figures.But they are not showing there figures to advantageIf I am not wearing a dress I wear a skirt, I own all lengths and styles and I never wear...
    sally1981 sally1981 31-35, F 21 Responses Dec 27, 2011

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    sylarisgay sylarisgay 18-21, M 8 Responses Feb 25

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    If I could wear a dress everyday,

    that would be heavenly! I remember a time where you would never catch me wearing a dress... That changed in college. Now I'm proud of my legs and closely getting more comfortable in my own skin
    SeanaO SeanaO 22-25, F 8 Responses Mar 19

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    NightOwlGirl NightOwlGirl 18-21, F 3 Responses Mar 28

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    I've been crossdressing

    for most of my life, but I absolutely love satin and silk dresses. My current favorite is a creme colored, floor length gown with pleated skirt, an open back (can't wear a bra with it) and jeweled waist.
    faellorien faellorien 26-30, M 10 Responses Jun 2, 2014

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    feedeeforyou feedeeforyou 18-21, F 1 Response Jul 15

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    im selling tons of adult baby girl dresses

    message me if your interested
    feedeeforyou feedeeforyou 18-21, F Jul 17

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    Mabel12345 Mabel12345 41-45, F 3 Responses Jun 9

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    Red Dress :)

    So tomorrow am going out with all of my friends to celebrate being well again.Everyone's into their monochrome and wanting to wear black and white. I like to wear a lot of black but not tomorrow...I'm going get out there in my bright red dress and red heels WOOT!
    FallenAngelWOOT FallenAngelWOOT 31-35, F 4 Responses May 10, 2013

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    I do. Call it old fashioned.

    Or girly. Or a desire to be just a little sexy, but I like wearing them. I am so glad spring is here!
    pinkcorsetgirl pinkcorsetgirl 41-45, F 17 Responses Apr 30

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    Anytime I'm out in public I'm dressed

    as a girl. It doesnt have to be a dress or a skirt. I can be wearing skinny jeans, capri's , short shorts or a beach cover-up over my bathing suit. I will always look and feel like a girl forever. Everyone that likes to wear dresses should feel feminine when wearing them.
    bobbylee111 bobbylee111 41-45, T 6 Responses Jun 21

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