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I To Wear A Skirt Or Dress In Public

Personal Stories, Advice, and Support 1,048 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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    Do any other women here enjoy giving people a

    little "peak" of yourself when in public?
    blondegirl36 blondegirl36 26-30, F 10 Responses Dec 1, 2013

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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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    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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    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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    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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    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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    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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    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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    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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    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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    Skirts

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

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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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    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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    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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    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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    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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    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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    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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    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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    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 5 Responses Sep 27, 2013

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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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    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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    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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    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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    Related Experiences

    Back in June I had written my first story in this group about how my skirt experiences got started. I mentioned how my wife reacted when I told her about this. I had not expected...
    Myotheridentity Myotheridentity 46-50 2 Responses Aug 7

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    Had to see a Dr today so I can see another Dr tomorrow. I have cancer for the third time. It's a form of skin cancer that's very treatable. Caught early it's not a problem. Does...
    shadowplt shadowplt 46-50, M 4 Responses Jul 23

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    This weekend my daughter competed in the Oklahoma USA Age Group swim meet. She did absolutely great! One proud dad. Traveling there and home I had the opportunity to wear my...
    shadowplt shadowplt 46-50, M 5 Responses Jul 27

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    I love wearing skirts :) I never wear panties with then though.
    starfire007 starfire007 13-15, F 13 Responses Jul 26

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    Am a very strict and experienced mistress and have been training newbies who have high interest in wearing skirts for so long and am willing to share my vast experience with you...
    bestmistress bestmistress 36-40, F 2 Responses 4 days ago

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    Apart from shorts, I have only been wearing dresses or skirts since I was 8 or something. And apart from the fact that my husband does not want to see me in trousers, I like...
    Susanna3 Susanna3 31-35, F 2 Responses 6 hrs ago

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    Freedom. There's just something about wearing a skirt that makes me feel more open and free. I love the movement of the skirt as I walk and the ease of adjusting the skirt and...
    slipgirl274 slipgirl274 61-65, T 5 Responses 3 days ago

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    Early one morning when my mistress got up and I sorted her breakfast she had that look in her eye some times it was really great and others I new I was going to suffer, after my...
    Sportsman007 Sportsman007 51-55, M Aug 8

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    Another unique experience. I was going home after work as usual. I got my go home soda and as I usually do, I took my slacks off to cruise in my boots and skirt. ( I wear a skirt...
    shadowplt shadowplt 46-50, M 3 Responses Jul 22

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    Today after a VERY early wake-up, (set my alarm to get up early yesterday) my dog heard it and woke me to go pee. Anyway, my wife cooked some great French Toast we did our...
    shadowplt shadowplt 46-50, M Aug 2

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    Just wondering, if I've good shaved legs and 27 male, an it's 2014, should I show off my shaven legs in public or no in a skirt? I shaven my entire body. I love the feel of nicely...
    TransAsian TransAsian 26-30, T 4 Responses Aug 2

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    Spent the day dressed around the house. Heels, skirt and a nice blouse. Didn't really do much, just a day of relaxation. Something struck me. Why can't people be like our pets...
    shadowplt shadowplt 46-50, M 2 Responses Aug 3

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    Tomorrow I have to drive another two hours back to the city. This time to see an eye doctor. I had surgery on my right eye socket last February and I have to follow up with a...
    shadowplt shadowplt 46-50, M 3 Responses Aug 10

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    My wife was miffed at me today. I thought it was because I was wearing a skirt last night. Turns out she had a beef with how I was discussing living arrangements with my 23 yr old...
    shadowplt shadowplt 46-50, M Jul 28

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    Yesterday I took a two hour drive to a swim meet in a nearby city. I worked as an official. I drove there wearing my skirt, heels and uniform shirt. Once at the pool I ditched...
    shadowplt shadowplt 46-50, M 1 Response Aug 10

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    My first skirt was a black and white very flowing and full ankle length with a side zipper and button closure, it didn't take long for a denim mini to show up followed by a maxi...
    CdKimmi CdKimmi 61-65, M 1 Response Aug 12

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    I found my Skirt I want to buy and wear!! Victoria's Secret Easy Mixers The Lounge Skirt $29.50 JW-311081
    TransAsian TransAsian 26-30, T 4 Responses 1 day ago

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