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I To Wear A Skirt Or Dress In Public

Personal Stories, Advice, and Support 1,033 People

    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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    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 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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    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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    Skirts

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

    Hope everyone had a Merry Christmas. I know I did. Had a discussion with my wife about dressing. It's still ongoing. She's comfortable about me wearing skirts if I'm going to...
    shadowplt shadowplt 46-50, M 4 Responses 2 days ago

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    I wore skirts for the first summer this year on days that were 75F or more. I thought maybe when it gets warm again, I'll wear skirts with pantyhose underneath on days that are 65F...
    Cetacean Cetacean 36-40, M Dec 16

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    This was a news headline in our local newspaper and all the news channels. Female volunteer turned away from Festival of Trees for wearing pants instead of dress, skirt. The girl...
    Sharon03 Sharon03 56-60 5 Responses Dec 9

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    Girlfriend and I went to a costume party a few years back and I was dressed up as a girl. That in it self isn't strange at a costume party. I was wearing this black pvc mini skirt...
    nylonbritches nylonbritches 51-55, M 1 Response 3 days ago

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    Tomorrow I'm driving to another city in the afternoon. I'm planning on wearing my favorite skirt and boot heels all afternoon and throughout dinner. I'm only taking male clothes...
    shadowplt shadowplt 46-50, M 1 Response Dec 11

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    Well today I only had to work a half day. I wasn't scheduled for an afternoon simulator, so....I went home and changed into my boots and skirt. Sat on the couch and watched some of...
    shadowplt shadowplt 46-50, M 3 Responses Dec 3

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    This has been a skirt less weekend. 😢 Yesterday I attended my daughters USA swim meet. Wow what a girl. Set several PR's. Very proud of her. Of course I couldn't dress for...
    shadowplt shadowplt 46-50, M 1 Response Dec 7

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    cute little skirts with designed tights and a jumper... my favorite :D so comfy
    hdhdodkdhdi hdhdodkdhdi 16-17, F Dec 19

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    I've always wondered why. Ever since I was a small child I was told that it was okay for a girl to wear "boys" clothing but that it was completely and utterly wrong for a boy to...
    Unapologeticallybrilliant Unapologeticallybrilliant 13-15, F 1 Response 4 days ago

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    Tonight after dinner with my wife and girls I went out to Penneys to look for dress slacks for the work, I looked around the men's section and couldn't find anything a size I could...
    shadowplt shadowplt 46-50, M 3 Responses 5 days ago

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    Well now, my In-laws were here for the past two days. Had to dress manly while they are here. In the morning they and my wife and I get up early. I forgot that I'd painted my nails...
    shadowplt shadowplt 46-50, M 8 Responses Nov 28

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    Girls, tonight I'd like to say thanks to the responses I've received on this site. Could some explain to me how to put on eye liner and still look like a man. I've gotten the...
    shadowplt shadowplt 46-50, M 2 Responses Nov 29

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    I want to see pics of trans male to females or boys dressed as girls ages under 25
    raileymathins raileymathins 18-21, T 1 Response 6 days ago

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    I really enjoyed my afternoon today. I got off work early and went home. I was able to wear my fav skirt and boots for several hours. Washed my used panties and stockings and...
    shadowplt shadowplt 46-50, M 3 Responses Dec 17

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    Feeling fem today. I really want to get on a skirt, heels and a blouse/shirt. Settling into bed tonight with a short skirt and tee shirt waiting for what Santa brings. 😍 going...
    shadowplt shadowplt 46-50, M 1 Response 4 days ago

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    I'm ecstatic today😀 I drove to the city to just kill some time and do a little shopping. The way down, while shopping and they way home, I wore my favorite skirt, high heeled...
    shadowplt shadowplt 46-50, M 3 Responses 3 days ago

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    I love skirts I have mostly worn short ones which are great cause they let everything breath. I love how it feels when you sit down with a skirt on!
    LexyCD LexyCD 18-21, M 1 day ago

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    I want it to be normal to wear corsets and full length dresses in every day life and have it be socially acceptable, instead of having people stare at me wondering how insane I am...
    21goth12 21goth12 18-21, F 1 Response Dec 13

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    Tonight my wife and daughter went to Wally World to shop. I've changed back into my fem clothes while they're out. I'll change back before they get home. Really enjoying the skirt...
    shadowplt shadowplt 46-50, M 1 Response Dec 17

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    I got this skirt today while in the city. I really like the colors and the flare at the bottom.
    shadowplt shadowplt 46-50, M 4 Responses Dec 20