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I To Wear A Skirt Or Dress In Public

Personal Stories, Advice, and Support 1,139 People

    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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    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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    Do any other women here enjoy giving people a

    little "peak" of yourself when in public?
    Hotwyfe Hotwyfe 31-35, F 12 Responses Dec 1, 2013

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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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    Skirts

    t wear skirts tops at home alot outside to
    azcd azcd 61-65 May 28, 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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    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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    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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    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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    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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    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 22-25, F 3 Responses Dec 4, 2010

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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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    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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    Its especially fun if you dont wear anything

    underneath ;) you can get a lot of guys to do... a lot more than youd expect when a teenage girls rubbing her bare *** all over you on the bus. It makes me wet thinking about when I used to do that stuff >~<
    TheKittyToii TheKittyToii 16-17, F 1 Response Mar 11, 2015

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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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    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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    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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    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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    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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    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 3 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 61-65, M Jun 26, 2012

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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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    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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    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 10 Responses Sep 27, 2013

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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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    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 51-55, M 1 Response Feb 17, 2011

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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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    Related Experiences

    As Christian women we are called to dress modestly and to express our God given femininity, which for means, in our society wearing a modest skirt and top or dress everyday. I don...
    MrsSThomas MrsSThomas 36-40, F 3 Responses 2 hrs ago

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    On the weekend my parents took me out i live by the sea it was cold and rainy but as always i had to wear my football shorts but they took me out in shorts (no underwear) a...
    Littlenudeboy Littlenudeboy 13-15, M 1 Response 3 hrs ago

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    Wearing very short & sexy miniskirt are my favorite. ...looking gorgeous & feminine all the time ! Not forgetting my ....short jeans pants too....looking curvy on my butt !
    Tsgirl86 Tsgirl86 26-30, T 3 hrs ago

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    I dont like i love pantyhose i love howy my 39inch long legs looks in them.How good they feel when i walk and my nylon covered thighs rub each other.My right now favorite is my...
    Jazonx Jazonx 36-40 6 hrs ago

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    Love to go out dressed in a short summerdress and show my sexy body , I usually have a bra on and stockings with a garter and high heels, I never have any panties on, love to show...
    cdmartina cdmartina 41-45, M 1 Response 8 hrs ago

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    I adore dressing in vintage lingerie and dresses. I feel so relaxed.
    Ozfisher71 Ozfisher71 41-45, M 10 hrs ago

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    Is this an acceptable length skirt for a school? I need opinions x
    LeahUK LeahUK 13-15, F 26 Responses 3 days ago

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    Dress up Time! Off to my very special lady friend who will do my pretty tarty makeup, dress me up and take lots of pretty girly pictures. What a fun time we have!
    deleted deleted 26-30 5 Responses 6 days ago

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    If I wear a dress and wear my hair girly and it hurts no one ... So what, happiness is all that matters
    Dryermaniac Dryermaniac 46-50, M 2 Responses 6 days ago

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    There I was. Sitting at my apartment watching TV when my door bell range. Now I'm wearing my skirt and heels when I answered the door. It was the post lady asking a question. We...
    shadowplt shadowplt 51-55, T 4 Responses 6 days ago

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    Yesterday was a good day for me and a bad one too. Good day: I invited my daughters over for a taco dinner night. Just a time to be with them and converse. Had a great meal and...
    shadowplt shadowplt 51-55, T 5 Responses a week ago

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    I prefer skirts to trousers for pretty much any occasion. when I do wear pants they tend to be women's and other than jeans have a side or rear zipper.
    MyFeminineSide MyFeminineSide 41-45 a week ago

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    Ahh, freedom. So much more comfortable. In the winter when its quite cold I wear them with tights or hose. In the summer oil up my legs and go. Of course, I like short shorts...
    onefourfun4u onefourfun4u 61-65, M 3 Responses Feb 2

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    I like to buy cute girls shorts on the internet the kind that zip up the side or on the back. They are hi waisted and dont have pockets. I have them in white red and black. I...
    sissybracd sissybracd 26-30, T 5 Responses Feb 1

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    in the summer I do it all the time! its fun to ''accidentally'' bend over too far so people can see what's underneath! :)
    sexxibaby4u sexxibaby4u 18-21, F 11 Responses Feb 1

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    Wow, just spent a s--- load of money to attend a conference in May where I get to spend a week with a bunch of people like me. I'm going to Esprit 2016. I'm scared, hopeful and...