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I To Wear A Skirt Or Dress In Public

Personal Stories, Advice, and Support 1,057 People

    To Wear A Skirt In Public

    i have a boss who i went out with and she works in marks and spencers and would like to wear a skirt where she works and try on clothes . she only works there on a sunday and would love to do it . i just love wearing skirts and dresses but i have only been to my meetings enfemme...
    georgiacd georgiacd 41-45 3 Responses Dec 28, 2011

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    Dresssed On Halloween

    This Halloween was the 1st time I went out in a skirt. It wasn't that bad as it was dark. There were few young girls that got close to me to see that I was a guy. They just started and a few giggled. Most adults didn't say or do anything. But then again it was Halloween
    sissybrenda56 sissybrenda56 51-55, M 5 Responses Dec 6, 2010

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    Would Love To

    i would love to especially on a windy day letting my dress/skirt blow up showing my panties
    addguy3455 addguy3455 18-21, M 3 Responses Oct 24, 2011

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    Dresses In Public

    I have worn a dress in public many times, one day i was in K-mart, and had to go to the bathroom. SAo as any ladie would, I went into the kadies room. Well didn't some clerk get an attitude, she says to me sir the ladies restroom is for ladies. Needless to say, I continued into...
    lottsafun lottsafun 61-65, M 4 Responses Sep 27, 2012

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    I Go Out Dressed Up In Drag Sometimes.

    My gay groups have activities about once a month or so. i always get dressed up for these occasions. mostly this summer it has been girl short shorts, and girl shirts, but I have gone to Halloween dances dressed in dresses before. I usually take a taxi so I don't have to put up...
    sisypwimp sisypwimp 41-45, M 1 Response Nov 11, 2010

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    Reactions From People

    Wife & I got together at a bar with some friends this weekend. Decided to wear a solid-colored sweater with a wool plaid skirt & loafers. Can't afford to buy a new Utilitkilt, so I bought the skirt on Ebay for $2. Wife said my legs looked pasty, and said that I ought to wear dark...
    deleted deleted 26-30 1 Response Jan 28, 2013

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    Mass Trouser-free Walk In Brighton Uk

    I think the LGBT people and straights should all join hands on this one... Gender and sexuality are not the main issues here. The central issue is the impoverishment experienced in a society that reinforces redundant stereotypes and unfairly discriminates against men in the...
    Btrue21self Btrue21self 51-55, M 3 Responses Oct 24, 2012

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    Brother Wearing Skirt

    i am male cd  when i was in the age of 13, 14 i use to share my room with sister. one day night time my sister told me to wear her skirt  just  for fun i immidiately tried her skirt and i was looking very nice girl . she immidately were her...
    radhaparag radhaparag 36-40, F 4 Responses Dec 4, 2010

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    Just Go For It

    There is no reason why a guy can't wear a dress or skirt in public.Since its been nice out,i've wore dresses twice, so far.I am a crossdresser but i wore these as my male self.No make-up,no falsies.Just as myself.Went yard saling,resale stores,grocery stores.Went to Best Buy and...
    cindyloulove cindyloulove 56-60, M 3 Responses May 30, 2012

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    Well, I Do ... As Much As I Can

    I started with this group as a "plan to", but hey, you know how it goes, one thing leads to another, and suddenly you're out there en femme in a favourite skirt buying the groceries.I just love it! I have had one or two smiles from younger people, every shop assistant so far has...
    Fullcircle Fullcircle 51-55, F 2 Responses Mar 7, 2011

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    Most Of A Week

    I am studying for a degree - distance learning, but recently Ihad a week long residential course.Of course, during the week I wore a skirt to the labs, to lunch, to the pub in the evening (when I wasn't writing up the experiements) . A WHOLE WEEK! No hassle!I nearly went into...
    purecotton purecotton 51-55, M 3 Responses Aug 21, 2012

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    Skirts

    t wear skirts tops at home alot outside to
    azcd azcd 61-65 May 28, 2011

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    I Want To So Bad

    I want to go out in public wearing a skirt so bad. Bad enough that I am thinking about it all the time. It is the fear of what people might think, say, or do. I know that I must get over this fear and the only way to do that is to just go out wearing a skirt. I know that I want...
    Adam59 Adam59 56-60, M 1 Response Jul 27, 2012

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    Wearing A Skirt In Public

    The first time  I wore a skirt was about 5 years ago.  I was involved with a theatre group.  After running our show, we run a special presentation of the show with roles reversed -- men play women and women play men.  Even the house staff goes along with it.  I finally went...
    ed8101 ed8101 56-60, M 3 Responses Feb 9, 2012

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    Wear A Skirt Night

    If I owned a bar on 'Ladies Day' which in alot of places is wed. The only way you could get in is if you are wearing a skirt or a dress and that would be for men and women. I would have the first beer free and half off for the rest of the night. Instead of calling it Ladies Day I...
    mustangsally1965 mustangsally1965 61-65, M 8 Responses Oct 15, 2010

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    A Walk In The Park

    I was 16 and it was summer and hot. Even the night air was so heavy and felt thick. I had gone to bed early and woke up around 2 am. I dawdled around thinking god, there is nothing on the TV. Sunrise wouldn't be for a few hours and I was restless. I went to the kitchen and...
    Melodie13 Melodie13 61-65, M 3 Responses Jan 27, 2011

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    I Only Wish I Could

    I love skirts and dresses. I would so love to be able to just relax and maybe take a nice walk in the park in a pretty sun dress, I love dresses Dennis / Denise
    deleted deleted 26-30 10 Responses Nov 9, 2010

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    Skirts As A Man

    I love wearing skirts and kilts as a man. I find them comfortable and a great alternative to shorts. When the weather is nice 9 months out of the year I wear nothing but skirts, kilts and shorts. When the days are cooler I wear breeks with knee socks for warmth. In the winter...
    billbb billbb 51-55, M 5 Responses Mar 7, 2011

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    My Wonderful Crossdressing

    So I was in school and was wearing panties and tights under my school uniform and someone noticed me. She asked me about it after class and I explained. She said it was so sexy so we went to my house after school. She admitted she had a garter fetish and she loved mini dresses...
    Tharealcsim Tharealcsim 22-25, M Sep 24, 2012

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    Do any other women here enjoy giving people a

    little "peak" of yourself when in public?
    blondegirl36 blondegirl36 26-30, F 11 Responses Dec 1, 2013

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    Running In Skirts.

    I often go to the forest and run in a skirt, I love running and the feeling of freedom.I bought a few polyester mini skirts at Goodwill for $4.00 a piece they breath and are comftorable no chaffing or bunching. My favorite is a pastel bubble skirt with flowers on it.
    skirt12 skirt12 51-55, M 1 Response Dec 4, 2012

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    It Is A Dream

    I would love to wear a dress or skirt in public. But for now that is just a dream. I would like to go out shopping dressed up in a skirt to start with then dresses later. I think it would be fun to do this but I'm not sure how it would be taken. When my wife gets comfortable with...
    Adam59 Adam59 56-60, M 3 Responses Jun 14, 2012

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    Shoping At Walmart

    The other day I went to a walmart near by wearing a dress and hose & flats. No wig or makeup as this is how I have been going out lateley. I can't pass so why even try. I shoped around but did not find anything I liked so I got a couple pars of panties and headed for the check...
    steffiecd steffiecd 51-55, T 4 Responses Oct 7, 2012

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    Shopping In A Skirt

    I went shopping today in very nice black skirt with my gorgeous orange tights and black combat style boots an orange jacket and cap. I spent about 45 minutes in the store going through the aisles. All the employees were helpul and they all called me sir. I felt great and can't...
    skirt12 skirt12 51-55, M 3 Responses Dec 7, 2012

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    I Wear Skirts In Public

    I am a male who has and does wear skirts in public. I live in a medium size city here in Ohio. I go everywhere in my skirts. I enjoy the comfort and some of the variable styles. I prefer the A-line skirts because of my long stride as I walk. The pleated and unpleated styles...
    Melodie13 Melodie13 61-65, M 4 Responses Nov 4, 2010

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    Swishing Skirt In Public

    Once Again, I just have to comment on just how Lovely the Pretty Yellow half slip is. Oh my Yes I just became overwhelmed at the Pretty Picture of your cute Yellow half slip, with pretty white lace about the hem. Yes, I too had a pretty half slip like that, along with a matching...
    carolannP carolannP 61-65, M 1 Response Feb 17, 2011

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    My First Skirt.

    This story is dedicated to two very special people here at EP, one who is living life to the fullest and enjoying with others and one at the early part of life who have touch me and taught me to love beening myself .thank you Billie and Sue.This happened many years ago and had...
    bernadine52 bernadine52 56-60, M 4 Responses Jun 25, 2011

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    I Like To Wear Dresses

    I enjoy wearing dresses when out in public. I will put on a dress with all the undergarments and step into a dress and shoes with two inch heels.  I take my purse with me and put on some jewerly.  Into the car to run about my errands to the bank, post office, grocery store and...
    jml2000 jml2000 56-60, M Jun 26, 2012

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    Men In Skirts

    I'm really thinking about wearing skirts or a dress in public. I don't mean dressed trying to pass as a woman. I mean with my full beard and all. I was thinking about the kilt thing and then I thought 'what the hell' I really want to wear a skirt or dress and I really don't want...
    mustangsally1965 mustangsally1965 61-65, M 26 Responses Oct 12, 2010

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    In Public Dressed Up

    apart from a couple of times as a teenager when my mother or aunt took me out i have not openly gone out in public as a female any where near my home. over the years i have occasionally gone out dressed when some where i was unlikely to meet any one i knew, and usually only with...
    Cyclopes66 Cyclopes66 51-55, M 2 Responses Oct 9, 2011

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    My First Time Wearing A Skirt In Public!

    In May of 2004, I went to San Francisco to participate in the "Bay to Breakers Marathon". I went to walk in the marathon with a group that called themselves "Bare 2 Breakers". Yes, this group walks the 7 1/2 mile course nude, but that is another story. I stayed at a hotel in the...
    Aguynamedsue Aguynamedsue 66-70, M 2 Responses Aug 15, 2011

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    Pressure!

    I was recently in a fight with a female i have never met in my life before! I can't tell you a reason for the altercation but she had been picking on me for a while! To make this story short we fought & later that night I dreamed I was approached in my moms living room with a...
    Victoria54 Victoria54 16-17, F Dec 31, 2012

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    Uh Ya! 💃

    I'm out & I'm wearing a dress right now! AND DRINKING A BLUE DRINK WITH AN UMBRELLA IN IT. 🍹🍹🍹🍹🍹
    Elzkitty Elzkitty 26-30, F Nov 22, 2013

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    Oops.. (:

    Looks like I forgot to wear panties today.. Oops (: just my smooth bare *** and my perfectly shaven ***** under my skirt. Maybe I'll see someone sexy enough at the office that makes me "accidentally" spread my legs open a little too far just so they can get a perfect view of my...
    foreveryoung1991 foreveryoung1991 22-25, F 6 Responses Sep 27, 2013

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    Related Experiences

    I've always been more boyish and spent my teenage years dressing in baggy black clothing (I admit I still do that a lot of the time :-D), largely because I was conscious of my body...
    kakhi kakhi 18-21, F 2 Responses Sep 13

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    i just love wearing skirts, expecially pleated school style skirts. would love to find a cheerleader skirt in my size.
    girlyAndrea1987 girlyAndrea1987 26-30, M 2 Responses 5 days ago

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    I love my skorts... I like and wear skirts in all their different styles, but my favorite is a pretty skort. They allow me to show off my legs better and are more comfortable on a...
    janusatv janusatv 61-65, T 2 Responses a week ago

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    I am a tall lady and loves to wear short mini skirts and dresses and shorts to show off my long legs. My husband loves to show me off to crowds of friends and strangers when we are...
    debbielovescruises debbielovescruises 41-45, F 2 days ago

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    My husband is all about it. I was very hesitant at first, but now I enjoy all the attention. Love wearing a small tight skirt with a thong underneath. Ill walk around in my heels...
    curiousbrenda69 curiousbrenda69 26-30, F 5 Responses Sep 8

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    Today I dressed up femininely in the dress you can see in the picture and it gave me a beautiful feeling of femininity and sensuality. The dress is a body contouring style made of...
    FontanaSlips FontanaSlips 41-45, M 1 Response Sep 9

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    I would love to wear a pair of opaque tights with either a short skirt or pair of shorts in public.
    MITUK MITUK 36-40, M 2 Responses Sep 9

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    To those of you who've been reading my posts about wearing a skirt on the walking trail. Thanks for posting back. I'm slowly working up courage to expand where I am dressed. Your...
    shadowplt shadowplt 46-50, M 4 Responses 5 days ago

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    i love skirts and dresses but in high school people call you easy and the pervs try and get behind you on the stairs
    kkkeeennnzzz kkkeeennnzzz 13-15, F 3 Responses Sep 4

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    Tonight after dinner with my beautiful wife, I went to our local walking trail to work on my swim officials test. While there, I decided to take another walk. In my skirt and boots...
    shadowplt shadowplt 46-50, M 2 Responses 4 days ago

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    One more night out dressed. Every time I feel more comfortable in a skirt. Sat at a table with park benches and worked on my swim homework. No one said or did anything. My hair is...
    shadowplt shadowplt 46-50, M 1 Response 1 day ago

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    I recently purchased the skirt you can see in the picture which I am wearing which is a body contouring style made of soft polyester a wonderful multi purpose fabric. When I put...
    FontanaSlips FontanaSlips 41-45, M 3 Responses Sep 9

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    I just got my first skirt! Right now I'm sitting in my room doing homework wearing a skirt and panties, with my legs freshly shaven and a nice new coat of a royal purple nail...
    jjthom jjthom 22-25, M 2 Responses Sep 20

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    Today I drove from my city to the big city to do some shopping without my wife. Just a me day. Wore mascara, a skirt boots. I had so much fun rummaging thru the women's section...
    shadowplt shadowplt 46-50, M 5 Responses Sep 21

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    Tonight was a total success. After dinner as it got dark, I told my wife I was going out to chill and relax. We have a two mile walking path nearby. I drove to it wearing my new...
    shadowplt shadowplt 46-50, M 4 Responses Sep 22

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    Once again I went to the local walking trail wearing this skirt. Just roamed the trail. Absolutely thrilling. I'm slowly convincing myself that most people really don't care what...
    shadowplt shadowplt 46-50, M 5 Responses 6 days ago

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    While I like the feel and comfort of wearing a skirt, I like watching American football even more. I may be a guy in women's clothing, but I'm still a football guy Tomorrow...
    shadowplt shadowplt 46-50, M 3 Responses Sep 4

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