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I Like Wearing Dresses

Personal Stories, Advice, and Support 6,612 People

    I love crisp tailored clothes- I try to wear

    nice jackets, pencil skirts or shift dresses for work. Usually in neutral colors like white, black gray or navy. Sometimes I might throw in a tailored vest, collared shirt underneath. I also love wrap dresses. Ideally in a rich jewel color like blue violet, raspberry pink...
    theyrereal theyrereal 31-35, F 5 Responses Jun 25

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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 9 Responses Oct 7, 2013

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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 61-65, F 11 Responses Nov 24, 2011

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    Dress is the only thing I wear in summer.

    T-shirt and pants make me feel like a boy now. That's odd because I used to wear them almost everyday...before I turned 22 yo.
    Jadewayne Jadewayne 22-25, F 5 Responses Jun 8

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    I'm a jeans-and-T-shirt kind of girl,

    but I just love dresses. My dream is to find the perfect dress to wear with Chucks.
    cece930 cece930 18-21, F Jun 25

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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 7 Responses May 25

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    I love being able to be

    such a girly-girl when I want. :) I don't wear dresses much in the winter, but I love summer dresses! :) :)
    MissThickNSexy MissThickNSexy 18-21, F 5 Responses Jun 2

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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 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

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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

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    lovelypoison44 lovelypoison44 16-17, F 3 Responses Sep 19

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    Slacks And Pants Are Unhealthy

    I wear either dresses or skirts as much as possible. I have been dressing female for the past two years. I was born intersexed, raised as a boy, but was always a girl. What I like to do during the summer is not wear slacks or pants. Slacks and pants do not keep you cool...
    Micayla Micayla 61-65, F 13 Responses Aug 15, 2008

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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 44 Responses Mar 21

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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 39 Responses Jul 4, 2012

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    KinkyKatieLouise KinkyKatieLouise 46-50 7 Responses Aug 13

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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 23 Responses Apr 20, 2013

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    When leaving my home

    and going out to work, church, running errands, shopping, etc., I love to wear a nice looking short dress or wrap around skirt. I compliment that by wearing hose and four inch heels and carrying a nice looking purse as well.
    pattywoods pattywoods 31-35, F Jan 20

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    Dresses are wonderful to wear,

    I like the way a well fitting dress covers my body. I went clothes shopping today for something to wear to a party with a friend and we went from boutique to boutique, they all had amazing dresses but nothing really got either of our eyes. We had given up and were walking to a...
    paula3198 paula3198 46-50, F 3 Responses Jun 14

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    I just took a good look at my favorite house

    dress, and realized I'll have to replace it. It is threadbare! I like it so much that I've worn it out. It is a yellow cotton shirtdress that I sewed from a Butterick pattern. I still have the pattern. Maybe I'll make another one in a different color.
    aprilrose aprilrose 61-65, T 3 Responses Jun 26

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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 26-30, F 8 Responses Jun 8

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    I want to go out in a dress.

    Why is it so hard!!
    nabz77 nabz77 31-35, M 5 Responses Jan 25

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    Ok I was born a guy,

    but I love to wear a beautiful dress. There are so many styles and materials. And feeling beautiful isn't something that only part of the population should experience
    Abilohman Abilohman 26-30 2 Responses Feb 8

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    So I'm going through college right now,

    and don't have money to buy stuff like girl clothes. But if you buy me something off my wish list I'll send you a whole bunch of sexy pics of me k. http://www.amazon.com/gp/aw/ls?lid=1ZMDJL0TT8SX0 Just message me to let me know you bought something and I'll make it worth your...
    Poopoohead17 Poopoohead17 18-21, M Oct 28

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    I really really want to wear a dress out.

    But I'm way too shy. Any girls in sydney want to take me out??
    nabz77 nabz77 31-35, M 4 Responses Jan 19

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    Call Me Old-fashioned

    Call me old-fashioned, but I like wearing dresses. Not frumpy ones, not slutty ones, not too flouncy ones, or even cutesy ones.... I like ones that are just right. I like them to be comfortable and a little flirty.
    scarlet54 scarlet54 36-40 20 Responses Apr 2, 2008

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    I know there are a lot of.

    Sissy posts and most sound fake. I am a real life sissy submissive and have been for years. Currently my sex is locked and I do not have access to the key. I am drinking coffee in a Dennes before I go home and redress into a housemaid dress and clean. I wear a bra and breast...
    beyerswede beyerswede 61-65, M 5 Responses Feb 1

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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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    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 22 Responses Dec 27, 2011

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    My mom knows me so well!

    She came home with this dress for me<3
    Alliforevers Alliforevers 16-17, F 13 Responses May 21

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    Thank you all for your wonderful comments.

    I am encouraged to show you another short dress. It is crotchet and daring for me because i never wear a bra. Although the shoes i wear here are no mules i love them :).
    HeelsKitten HeelsKitten 31-35, F 12 Responses Nov 13

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    Being a TG I just love to look really pretty

    for my Man and make all the other guys jealous and my boyfriend HAPPY! I am proud and love being A special ladyboi
    FemGayBottom FemGayBottom 26-30, T 5 Responses Apr 26

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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 22-25, F 12 Responses Jan 10, 2012

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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 8 Responses Oct 24

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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 5 Responses May 7

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    Jeans And Trousers

    Sure i love my skinny jeans and cropped hipster combats, but whats happened to society when women wear them to go out for a evening? When i go out at the weekend all you see is the majority in jeans and trousers, if its christmas theres no glitz glamour and dresses, its jeans...
    Blondevixon Blondevixon 31-35, F 25 Responses Jun 8, 2010

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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...
    allgirlallthetime allgirlallthetime 56-60, T 3 Responses Aug 29

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    I used to be embarrassed having to wear them,

    now I can't wait for summer :)
    almaera almaera 18-21, F 2 Responses May 10

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    Ok Now I know I've Gotta Come Out....

    Ok here we go….I cross-dress every chance I get and underdress when I go out, but my partner/girlfriend doesn’t know. I have to tell her…the guilt is killing me I recently started (underdressing) wearing panties in front of her just waiting to be sprung….no such luck, ok...
    21Blue12 21Blue12 46-50, M 18 Responses Jun 13, 2012

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    Up too late. I am so freaking bored I thought

    I might share how much I love dresses....lol Does anyone have anything more interesting to talk about.
    lostnotfound78 lostnotfound78 36-40, F 7 Responses Feb 11

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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...
    AdrienneJaye AdrienneJaye 22-25, T 31 Responses Mar 5, 2012

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    Irán a Daymond Vaše želanie sa splnilo v

    južnej Kalifornii! Nebolo suchého oka u všetci pozvaní na Irán a Daymond obradu. http://www.zhdresses.org Bolo krásne slnečné popoludnie v Riviera Country Clube. Niekoľko minút pred tým, že Irán šiel uličkou, oblaky pokrývajú západ slnka na love. Daymond Irán...
    orologiomegarepliche orologiomegarepliche 22-25, M Sep 12

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    I have several coloured dresses,

    black, blue, red, crotchet etc....but i really like to wear a white men's shirt as a minidress, it is very comfortable in summer, airy and soft on the skin :).
    HeelsKitten HeelsKitten 31-35, F 14 Responses Nov 8

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    Funny I use to hate wearing dresses

    when I was little.I gave war to anyone that would try to put me in one.My grandmother (god bless her evil little soul) she managed to get me in some poofy cream puff looking dresses just to go to church.It was a real struggle to get into the church van.Now as an adult I feel...
    17hugs 17hugs 22-25, F 4 Responses Feb 23

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    See Through Dress

    i just got a new sun dress a few days ago and it is a tank top dress and short, but not mini. it is white with big red yellow and green flowers all over it.i have never worn a tank top dress before because i always wear a bra. BUT i thought i would try it. i went to the park...
    closet36 closet36 61-65, T 13 Responses May 3, 2011

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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 18 Responses May 7, 2012

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    Related Experiences

    I started dressing when I was 11 or 12. I would wear my step mom's clothing any chance I could. I still dress every chance I get and love wearing dresses and skirts
    jasminecd5 jasminecd5 36-40, M 4 Responses Nov 1

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    It so happens that there was a long time before my opportunity to go out a 4th time. But in the summer my wife was going away for a week-end. I was so excited!! I shopped around...
    donnaka donnaka 36-40 1 Response 14 hrs ago

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    I'm transgender, but gender doesn't matter on what you like to wear. I mean.. sometimes I'll feel like I'm less of a boy when I wear "girl" clothing, but w/e. I love wearing those...
    SleepyGamers SleepyGamers 13-15, T 4 Responses Nov 10

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    Shopping trip planned for later this week to get a couple of dresses for Christmas parties.
    ris9358 ris9358 51-55, M 4 Responses Nov 4

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    dressing in public number 3. Who else has made this journey- having a single item you obsess about for years (often panties , i believe , but mine was tights) , telling yourself...
    donnaka donnaka 36-40 9 Responses Nov 4

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    I Love Tight Dresses And Skirts. They look great and really make me feel feminine
    jasminecd5 jasminecd5 36-40, M 3 Responses Nov 10