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I Like Wearing Dresses

Personal Stories, Advice, and Support 7,395 People

    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 22-25, T 23 Responses Apr 20, 2013

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    I am a 15 year old sissy boy

    who wears his 18 year old sisters bra panties bikini gowns dresses leggings skirts pj and I wear her lipstick and eyeliner it's all a secret and I like men tough ones and masculine ones
    deleted deleted 26-30 Sep 18, 2015

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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 15 Responses May 7, 2012

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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 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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    feedeeforyou feedeeforyou 18-21, F 1 Response Jul 15, 2015

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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 11 Responses Aug 20, 2015

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    Mrskatearch Mrskatearch 31-35, F 11 Responses Jun 25, 2015

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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, 2015

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    Mabel12345 Mabel12345 46-50, F 10 Responses Jun 9, 2015

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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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    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, 2015

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    What do you think of this dress

    for a wedding? I will match it with black strappy heels :)
    GirlyLisaTG GirlyLisaTG 31-35, T 3 Responses Oct 29, 2015

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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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    I like wearing a beautiful dress with some

    heels. It makes me feel like a pretty lady.
    MsKristin MsKristin 22-25, F 4 Responses Mar 8, 2015

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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 6 Responses Aug 9, 2015

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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 46-50, M 10 Responses Oct 7, 2013

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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 11 Responses Jun 2, 2014

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    NightOwlGirl NightOwlGirl 18-21, F 3 Responses Mar 28, 2015

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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...
    deleted deleted 26-30 48 Responses Mar 21, 2014

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    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, 2015

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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, 2015

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    deleted deleted 26-30 1 Response Jul 16, 2015

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    My mom knows me so well!

    She came home with this dress for me<3
    Alliforevers Alliforevers 18-21, F 15 Responses May 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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    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 28 Responses Jul 23, 2015

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    I'm a 15 year old sissyboy

    who secretly wears his 17 year old sisters bra panties leggings tights lingerie bikini skirts dresses tank tops skinny jeans heels and of course make up and I'm secretly attracted to masculine tought men and hairy men
    deleted deleted 26-30 2 Responses Oct 20, 2015

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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, 2015

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    I have been dressing in women's clothes

    since I was 5 years old
    looking76yg looking76yg 36-40, M 7 Responses Nov 3, 2015

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    im selling tons of adult baby girl dresses

    message me if your interested
    feedeeforyou feedeeforyou 18-21, F Jul 17, 2015

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    As a pre-op M to F transsexual

    who has spent over half a century in female underpinnings the delight of openly wearing dresses or skirts is exhilarating and liberating. Dresses are also so practical, one item and you are done when getting dressed, they signal femminity and do not hamper leg movement, or can...
    Nuback Nuback 70+, T 2 Responses Oct 18, 2015

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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 20 Responses Dec 27, 2011

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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 18-21, M Apr 22, 2015

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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 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 46-50, F 16 Responses Apr 30, 2015

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    I adore floaty white sundresses with bare feet

    and nothing underneath. They are the polar opposite to what I wear for my job and they make me feel incredibly attractive and free. 
    LizzieLost LizzieLost 18-21, F 7 Responses Sep 21, 2015

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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 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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    This cool weather is a shock

    when I get in the car in the morning. Maybe I'll wear sweats under my dress till I get to work :)
    Blond4you Blond4you 22-25, F 4 Responses Oct 19, 2015

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    Sometimes shorts or jeans make more sense,

    but if I have the option, I'll wear a dress or skirt. They're cooler and easier to get into and out of, and most men notice a woman more quickly in a dress. Here at the beach, I put a summer dress over my swimsuit and I'm ready for anything :)
    Softandsweet2 Softandsweet2 22-25, F 10 Responses Sep 27, 2015

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    I Was Raised In Dresses

    i was born a boy with and older brother by 4 years who hated me. my father was an over the road trucker and never home. my mother wanter a girl, not another boy, so she raised me as a girl. in every way shape and form. i had only girl things. i only played with the girls and i...
    closet36 closet36 61-65, T 8 Responses May 5, 2011

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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 71 Responses Apr 12, 2015

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    I'm a man, and no, I don't wear dresses.

    No cross dressing for me! That being said, there is nothing better on a woman than a shapely dress fitting to her beautiful feminine form. Just to enjoy the soft fabric, the beautiful patterns, the lace and frills, the cut of the design...It is all like a guided tour and...
    TheRedTie TheRedTie 31-35, M 1 Response Jan 12

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    marebare303 marebare303 13-15, F 6 Responses Jul 31, 2015

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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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