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I To Wear A Skirt Or Dress In Public

Personal Stories, Advice, and Support 1,028 People

    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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    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 2 Responses Aug 21, 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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    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 9 Responses Nov 9, 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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    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 7 Responses Sep 27, 2013

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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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    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 2 Responses Jun 14, 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 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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    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 3 Responses Dec 4, 2010

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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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    Skirts

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

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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 2 Responses May 30, 2012

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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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    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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    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 2 Responses Oct 24, 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 24 Responses Oct 12, 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 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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    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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    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 4 Responses Mar 7, 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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    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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    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 2 Responses Oct 24, 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 6 Responses Oct 15, 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 Jan 28, 2013

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    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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    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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    Related Experiences

    As a man I want to wear skirts all the time. Pants are so boring and can be hot along with being uncomfortable. I think if more men wore skirts in public then society would be more...
    Adam59 Adam59 56-60, M 4 Responses Nov 16

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    I am sad to say that I do in fact like to wear skirts. But because I practically grew up with them since my sister liked to cross-dress me and make me wear miniskirts so I've...
    Butterking47 Butterking47 18-21 5 Responses 2 days ago

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    I am a male and I like my skirts. My skirts are mostly knee length. I find so comfortable to wear. I have pencil skirts and some flowing skirts. I wear my skirts or dresses all the...
    Adam59 Adam59 56-60, M 2 Responses Nov 19

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    Any real girls in here wanna join me in peeing contest in public
    lesbian2015 lesbian2015 31-35, F Nov 12

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    I'm spent. Yesterday I f-up with my wife. She's PO'd at me and won't comment about it. I want to clear things up with her but she's claimed up. My f-up was I was home comfortably...
    shadowplt shadowplt 46-50, M 3 Responses Nov 17

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    Ok, I'm a happy camper this afternoon. Went to work and wasn't scheduled for a single simulator mission. So.....I took the afternoon off, went home and am sitting on my sofa...
    shadowplt shadowplt 46-50, M 6 Responses a week ago

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    Today my wife and daughter traveled to another town for a swim meet. I stayed home because I was officiating a YMCA swim meet here in town. This afternoon I got to wear my new...
    shadowplt shadowplt 46-50, M 1 Response 4 days ago

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    Went to the swim meet. Daughter smoked it today. Very proud of her. I did dress for the trip and throughly enjoyed the feeling of a skirt swishing in the breeze as I went into...
    shadowplt shadowplt 46-50, M Nov 15

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    Today has been a wonderful day. I did dress underneath my male garments until I got home. Then I went back to boots in heels,skirt and shirt. My wife is accommodating my desires...
    shadowplt shadowplt 46-50, M 2 Responses Nov 18

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    Yesterday I found something I'd never thought I'd like, a dress. I went into the store just casually looking over clothes. There on the rack was a dress that was made of a material...
    shadowplt shadowplt 46-50, M 4 Responses 5 days ago

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    A man in a skirt is a man in a skirt. A skirt is a piece of clothing. It does not change your gender or make you more feminine. Men have the rights to wear a skirt if they want too...
    Adam59 Adam59 56-60, M Nov 12

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    I love to flash girls my panties in public
    Pushupbra Pushupbra 31-35, F Nov 1

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    Most definitely a skirt. Skirts are cooler and don't drag on the legs like trousers. Skirts come on a wide variety of styles, colors, and prints. If I given the choice of skirts or...
    Adam59 Adam59 56-60, M Nov 19

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    I'm trying something new to me. I purchased some women's panties. I was curious about how they felt. Really it's not different than wearing male bikini underwear. It is fun under...
    shadowplt shadowplt 46-50, M 6 Responses Oct 28

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    Just had a chance to put on a cute new skirt. I've been underdressed all day and now had the opportunity to shed my pants and wear a skirt.
    sharonwoods sharonwoods 51-55, M 3 Responses Oct 31

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    Went to a swim meet today a couple hrs from my house. Wore my red skirt, new heeled boots and panties. As I drove I had the urge to have to use the restroom, whoops forgot to bring...
    shadowplt shadowplt 46-50, M 3 Responses Nov 8

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    Getting ready for work. Have to dress male while there, but commute as is.
    shadowplt shadowplt 46-50, M 1 Response Oct 29

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    Since I had an appointment this morning I had to wear guy clothes. On the outside. Underneath I was wearing panties and a slip. Couldn't get away with a bra today. Now that I'm...
    sharonwoods sharonwoods 51-55, M 4 Responses Oct 29

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    Today I had planned to drive to the city wearing a skirt and doing some shopping. A cold front passed last night and the temperature dropped 30 degrees. Now I'm thinking of getting...
    shadowplt shadowplt 46-50, M 5 Responses Nov 11

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    Today my wife and daughter are traveling to "the city" for a two day swim meet. I'm following a bit later. It'll give me a chance to dress and have some fun. I'm going to post a...
    shadowplt shadowplt 46-50, M 1 Response Nov 15