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I Like Wearing Dresses

Personal Stories, Advice, and Support 6,384 People

    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 5 Responses May 10, 2013

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    Never Appreciated Them Until I Was 18

    I grew up with 2 women, my mother and her partner. They both always wore dresses or skirts. When I started wearing them, they just became clothes. I know they fely comfortable and were girls clothes. As I got older I started to understand what a dress is. When I hit 18 my real...
    RobinLeade RobinLeade 22-25 2 Responses Aug 23, 2011

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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 31-35, F 7 Responses Feb 11

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    Every morning I look thermometer

    and hope that it would be good weather to wear a skirt or dress. Yes I wear lots of jeans and shorts too, but skirts and dress has been always at my favorite.
    PigletThinksPink PigletThinksPink 13-15 1 Response Jan 1

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    I Get A Mommy

    Hi! My name is Sylvia James and my mommy is Theresa. She would never share this story on her own so I will tell it. You see Theresa became my mommy when she was three and we have been together ever since. So I was there and excited when this story took place. So when mommy was a...
    SylviaJames SylviaJames 56-60 Sep 20, 2013

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    Update: I have bought 3 dresses recently,

    - One amazing chiffon dress, Peach and Cerise with a Lime tie belt, for a special event now in February. - A gorgeous Royal blue sleeveless, ruffled neckline dress for Christmas...wanted to wear red but couldn't find anything I liked so went with what colour I knew suited me...
    LilRedd10 LilRedd10 36-40, F 7 Responses Dec 30, 2013

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    Shemale In A Dress...Any Dress

    Yes! I am a shemale girl...I don't just like wearing dresses....I LOVE it. Love and hugs and kisses to the girls (I also am lesbian), Susan
    susanunderhill1986 susanunderhill1986 26-30, T 1 Response Oct 16, 2013

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    My Dresses

    I collect dresses...they are my prizes...I can t get enough of their beauty and feminine grace...i have short dresses and long dresses...Indian dresses and Chinese dresses..Arican dresses, a jungle dress...I love dresses that show my shoulders and dresses with a slit by the leg...
    Abeautifulheart Abeautifulheart 18-21, F 8 Responses Oct 11, 2012

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    My parents want that I wear skirts then i go to

    school and also dresses when we go out for dinner or when we go to church. but hey that is no problem for me. I like dresses. exspecially when it is sommer. :D I don't understand woman who say that dresses look awfull or too girlish. Of course I like to wear jeans and T-shirts...
    Jennyred Jennyred 13-15, F 5 Responses Dec 23, 2013

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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 never wear dresses.

    Never. I have one dress in my closet from my 8th grade graduation and that's it. I love dresses and I want to own more, but before recently I was self conscience about they way I looked. I always found something about my body that I didn't like while wearing a dress and it...
    slytherinseeker98 slytherinseeker98 13-15, F 4 Responses Jan 6

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    Cheerleading Uniform

    When I was in high school, i've always wanted to be in cheerleading. I liked it when the girls would go out o the field in thier vest tops and skirts to cheer the team on. In my senior year, i had that chance to become a cheerleader...i showed the coach that i can do a roundoff...
    ShelleyAnnDowney ShelleyAnnDowney 36-40 2 Responses Dec 27, 2012

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    What I'm Wearing Tuesday

    Tomorrow I'm wearing my pink stretchy peplum top over pink bra and my red stretch skirt which is tight and dead sexy might put red suspenders on red knickers and black stockings and 3 inch heels I've worn my dress all day today and love it first time I've worn them all day Now...
    Keithmered Keithmered 61-65 2 Responses Oct 21, 2013

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    When I was young my mum would sew me the

    prettiest dresses, I remember people would comment on how lovely my clothes were. Then, when I was in my late teens to mid 20's I mostly liked to wear black pants or jeans. Then I would wear anything that would fit me basically for ages due to pregnancy, post pregnancy weight...
    LilRedd10 LilRedd10 36-40, F Dec 2, 2013

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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 3 Responses Feb 8

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    deven44 deven44 66-70, M 3 Responses Jun 1, 2013

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    My First Time In A Dress

    I can remember the first time i had a dress on. i was 13 . i was at my grandmothers house for the weekend and i was playing football when i come back from playing i was all mud !MYgrandmother told me to...
    maryyork50 maryyork50 18-21, T 8 Responses Nov 29, 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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    There Is Nothing Like It

    There is nothing like slipping into a dress. To be free to move around without something dragging on your legs. I always wear a slip under my dresses. It is so sensual. The dress is so much cooler and sexier than pants or shorts. There are so many styles, colors, and prints that...
    Adam59 Adam59 56-60, M 7 Responses Jun 13, 2012

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    Hi can someone from England please help me,

    preferably female if so message me
    wallsies wallsies 16-17, M Dec 29, 2013

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    I'm not the girliest girl in the world,

    but I can say that I love wearing dresses. I like how they allow movement and require little effort.
    mizicu mizicu 16-17, F 1 Response Jan 3

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    The Blue Knit Dress

    About 20 years ago I was shopping in a consignment shop and came across a stretchy knit blue dress.  Well I had to find out if it fit.  I had my lingerie on underneath my jeans and was wearing a pair of breast forms.  Off to the dressing room to try the dress on.  I took off...
    jml2000 jml2000 56-60, M 11 Responses May 28, 2012

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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 5 Responses Feb 23

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    I Havnt Worn A Dress Since I Was A Little Girl

    When I was younger I would always be dressed up in dresses and girly stuff but once I got older I developed my own way of dressing myself that was all so girly lol. I've been wearing only jeans for many years now .I havnt woren a dress since I was younger not even shorts. I've...
    Bitterrsweet Bitterrsweet 18-21, F 14 Responses Feb 26, 2012

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    Dress Shopping.

    I went to the mall the other day and walked through every store in it that sold women’s dresses. I just could not help myself and I must have tried on about 10 to 15 dresses. There were a few that I liked but were to much money. I found one that was an $80 dress on sale for $47...
    mat2Robin43 mat2Robin43 51-55, M 2 Responses Oct 12, 2013

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    -- Only One Of the Bling Clutch Rest --If

    wearing a pretty dress , a bling clutch would 100% match your dress . below only one piece rest because the items put on the online store always slower that the hypostatic, When Lanshowcase got these new items (Bling Clutch) from the factory , it sold fast in the hypostatic...
    cookiekong cookiekong 31-35, F Jan 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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    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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    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 7 Responses May 5, 2011

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    Green Dress

    I wore a medical pump around my waist for several years and was unable to wear dresses. Upon having surgery, rendering the pump no longer necessary, I was finally able. I walked out of the hospital wearing a beautiful green dress for the first time in 10 years.
    zeetalo zeetalo 26-30, F Aug 31, 2013

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    Dresses Are Sexy!!

    I HAVE OVER 30 DRESSES AND I WAER THEM EVERYDAY ,NO MATTER WHAT THE OCCASION IS , I THINK DRESSES ARE SEXY NO MATTER WHAT LENGTH THEY ARE, I THINK A WOMEN SHOULD HAVE AT LEASE THREE KINDS OF DRESSES .
    bodwin1971 bodwin1971 41-45, F Sep 12, 2013

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    Shemale In A Dress

    Of course I love wearing dresses! I'm a girl...even though I was born a boy. I'm 5 feet tall so I naturally wear very high heels with my dresses (and my skirts too). I don't even own a pair of slacks, jeans, or shorts! Love to all the girls, Susan
    susanunderhill1986 susanunderhill1986 26-30, T Oct 7, 2013

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    What's Your Favorite Style?

    I'm curious what dress styles people like to wear.My favorites are like 2 opposite extremes...either really short and stretchy and tight...or more like just above my knees with really full skirts.
    subbie4julia subbie4julia 18-21, F 5 Responses Jul 17, 2013

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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 56-60, F 27 Responses Mar 21

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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 21 Responses Jun 13, 2012

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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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    Love To

    I love wearing dresses they make me feel pretty when i go out. I don't ubderstand ehy more women don't feel this way. Pants are so restricting i feel. Am i alone here?
    boredblondebadwife boredblondebadwife 26-30, F 3 Responses Sep 28, 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 1 Response Jan 20

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    When I was growing up,

    in Southern California, as a young girl, my mother always dressed me up in pretty and colorful dresses and skirts and blouses. also, I did wear jumper outfits too. I loved them then and now too the wearing of dresses, skirts and blouses, and jumpers outfits. I went every I...
    welldevelopedmom welldevelopedmom 36-40, F 1 Response Dec 6, 2013

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    Dress To Hide Arms And Legs

    Its just a little armless fun and pleasure to hide one or more arms inside a loose and stretchy dress. Go on, try the experience.... The reasons can be :- 1. Keep outer limbs warm in winter 2. Pose as vulnerable 3. Stop using devices like phones and remote controls 4. Mas tur...
    ChrisBloom ChrisBloom 31-35 Jul 14, 2013

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    The First Time I "Went Public" In A Dress

    I had not been "out" for long, when my first BF, a gorgeous hunk, coaxed me into "dressing up"; yep, wig, makeup, shoes, and a thrift store cocktail dress, to an AIDS benefit at a gay club in our town. It all came off nicely - of course it was at night - ha, ha! While it was...
    BuffyOh BuffyOh 66-70, M 2 Responses Sep 22, 2013

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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 26 Responses Jun 8, 2010

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    deven38 deven38 18-21, F 3 Responses Jan 2

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    My Summer As A Girl

    picking up from where i left off.. these girls were like sisters. they dressed alike, went every where together and i was one of them now. wheeeee when we walked off the bus to practice for the show i was so scared i could hardly walk, so they made me worm them up and that took...
    closet36 closet36 61-65, T 3 Responses May 7, 2012

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    I Feel Pretty!

    I haven't owned that many dresses, but with summertime coming, I'm thinking I should get some nice casual sundresses, hehe. I LOVE wearing dresses. I love feeling feminine and pretty. I like the way they swirl when I walk and flap in the wind. And when I get married, I'm...
    paperalias paperalias 22-25, F 3 Responses Apr 4, 2009

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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 12 Responses May 3, 2011

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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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    Dresses are amazing. They hug my hips,

    they highlight my body,and they make me feel beautiful. Hi-low dresses are my favorite,because of the way they angle down and highlight my legs and body. I love it when I walk in a room and people stare at me,because I feel like I attract all the attention. Dresses for me well...
    littlesis333 littlesis333 16-17, F 9 Responses Dec 15, 2013

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    Related Experiences

    Love dresses! 💜 I grew up in a family mostly of ladies. I was 6 when I was put in my first dress by my cousins. I was embarrassed then but I really liked that experience. Since...
    sissyyumi sissyyumi 22-25, M 5 Responses a week ago

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    is there any better feeling in the world than standing outside on a breezy day wearing a dress or even a skirt with wee cute panites on and just letting the wind blow them up to...
    Pjstuart Pjstuart 26-30, M 8 Responses 5 days ago

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    i want cross dress as a female like all the clothes,have long hair, makeup, jewelry and everything and also learn the ways of women. even how to do sex. plzzz message me and help...
    shifakhan shifakhan 18-21, M 1 Response a week ago

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    When i was at a friends I went to the bathroom amongst the dirty washing was his sisters skirt, i ******** off and put it on, it felt brilliant i had a little dance in the bathroom...
    mike020200 mike020200 16-17, M 5 Responses Mar 20

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    When i was at a friends I went to the bathroom amongst the dirty washing was his sisters skirt, i ******** off and put it on, it felt brilliant i had a little dance in the bathroom...
    mike020200 mike020200 16-17, M 5 Responses Mar 20

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    Good I wear women's underwear pantyhose dress heels I love it
    astroboy4545 astroboy4545 61-65, M 4 Responses Mar 21

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    I love dressing up as a schoolgirl, pleated miniskirt, blouse, and knee socks!
    schoolgyrlKaren schoolgyrlKaren 41-45 8 Responses Apr 6

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    I love the way they feel when they hang off of me and swish around as I'm walking. But I also love the way a short skirt shows off my round buns when I bend over. My wife knows I...
    SamanthaLei SamanthaLei 46-50, M 2 Responses a week ago

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