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I Am Wearing A Skirt

Personal Stories, Advice, and Support 817 People

    This goes back about 11 years,

    it was Halloween and I had an appointment to get my haircut. Knowing that the stylists at the salon dressed up for Halloween, I decided that this would be a perfect opportunity to wear a skirt,hose, and heels to the salon. I put on nude shade pantyhose, a knee-length tight...
    krisyca krisyca 41-45, T 4 Responses Mar 5

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    Love Black....

    I love black color , it makes you hot, sexy and elegant at the same time. Keeping those in mind I went for shopping last week and bought two black inner skirts, one is lil long and the other one is short net skirt with a stitched bikini inside. I loved already when I was buying...
    shania0adorable shania0adorable 26-30 2 Responses Jun 12, 2012

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    Haven't Always Though

    It is not unusual for me to wear a skirt.  In fact I wear a skirt almost every day.  I am comfortable in my skirts but I haven't always been this way. I learned to love skirts while being in a D/s relationship.  He  always wanted me to look my best and he...
    infiniteheart infiniteheart 31-35, F 13 Responses Dec 31, 2009

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    Love My Mini

    Right now I am wearing a plaid mini skirt.  I have on a pair of capizio dance tights and 3" heels.  I love the feeling!  I come home normally and put on my skirt, heels, bra and top almost every day to unwind. Sometimes I dont even need to put on hose becuase I was already...
    deleted deleted 26-30 2 Responses May 17, 2011

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    Me Too

    Yessss, I wear dresses and skirts, most off all girls-clothes and I'm feeling fine with that
    laikagirl laikagirl 51-55, M Jun 5, 2012

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    Doorbell!

    My wife and daughter are having a show break in the capital this weekend. Since they booked in the sumnmer, I had planned to dress while they were away, and bought a pretty sleeveless chiffon blouse to go with a petticoat. However, I didn't reckon for the November weather at the...
    Fullcircle Fullcircle 51-55, F 3 Responses Nov 12, 2010

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    Finally Some Time To Wear My Favorite Skirt!

    I have been thinking about it and thinking about it.I see where it is hidden every day and dream of putting it on and swishing my way around the house in it.I do get some occasional fleeting moments to throw it on and look in the mirror before having to slip it off and hide it...
    cdpattyny cdpattyny 46-50 9 Responses Nov 21, 2011

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    Skirts Rock

    Though I have a load of dresses, I have twice as many skirts, and generally wear one on a daily basis. I love the mix and match capability of the skirt and sometimes even change my top halfway through the day, just because I can. That can't be done with a dress. And if I'm going...
    josilver josilver 56-60 1 Response Sep 10, 2012

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    Wearing Of Skirts

    I started wearing skirts when I was 23 after buying one to see what it was like to wear a skirt & found out that I liked wearing a skirt so the next month I went out & bought 5 more. I am now 54 & I must have over 40 of them which I could only wear all day for 1 or 2 days a week...
    xdpaul xdpaul 56-60, M Jun 5, 2011

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    Working From Home

    I am wearing a short, black pencil skirt for work - with a black lace top, hose and black pinstriped 4" pumps. Just love the feeling and look of the pencil skirt - so classic for work.
    scaff69 scaff69 36-40 3 Responses Oct 15, 2010

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    My favorite skirts are my schoolgyrl plaid

    skirts. I have a red, pink, green, and kaki.
    schoolgyrlKaren schoolgyrlKaren 41-45 4 Responses Apr 12

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    I Luv Skirts!

    Skirts are always my first choice, denim minis or any kind of pleated skirt.  Especially with leggings and heels, of course!  My fav things to wear!
    denisegurl2 denisegurl2 46-50, T Jul 22, 2010

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    Hey

    hey i was just wondering how old you were because i am 14
    thenman thenman 13-15 2 Responses Oct 6, 2012

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    Black Lace In layers

    I love this skirt. It is almost ankle length, and made up of four layers of black lace. It has a black leather belt with studs stitched into the belt loops. I love it! I am wearing a black denim jacket above it, with underneath just my black leather bra (it has warm cotton cups...
    ToiledAraignee ToiledAraignee 22-25, F 4 Responses Nov 12, 2012

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    If Anyone Knows Me...

    If anyone knows me, they know usually my outfit consist of Jeans, and a t-shirt, or pajama pants, or a pair of capiries. But NOT today. Today I am wear a very sexy Shirt, along with a very sexy, black skirt. I Love it. Its not me, but I feel very comfortable in it :)
    deleted deleted 26-30 1 Response Dec 31, 2009

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    I Wear A-line Skirts

    I do wear everyday A-line skirts. They are very comfortable and cover the same as a pair of shorts. I realize you need to be careful on windy days or getting in or out of a car. Generally though there isn't a problem. Currently I own several skirts and have discarded all the...
    Melodie13 Melodie13 61-65, M 1 Response Nov 30, 2010

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    Skirt And Black Tights In Public For The First Time

    I am wearing a black cheerleader skirt that has white and gold on the bottom corner on one side with black tights while doing laundry at a public laundromat also wearing female boots that look like the one Kantinss wears in the film The Hunger Games and a female shirt all 100...
    Multiplex4862 Multiplex4862 26-30, M 3 Responses Aug 30, 2013

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    Skirts Are Great

    All types of skirts even the long ones are great they provide excellent movment and freedom they fit nice on your body and really are good
    mazzz77 mazzz77 18-21, M 1 Response Nov 10, 2010

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    I Love Wearing Denim Skirts

    I love to wear denim skirts. A couple of weeks ago I went shopping at a consignment store and they had a lovely denim skirt.  I grabbed it and went into the changing room. Turns out the denim skirt  was too big in the waist.  Oh, well.  I'll just have to keep looking and...
    jml2000 jml2000 56-60, M 2 Responses Nov 8, 2012

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    I Am Wearing A Skirt

    I am wearing a purple skirt with snowflakes design now  and also sissy panties.   They feel so comfy. I wish I could wear them all the time!  It's too bad some idiots call it gay clothing when a man wears skirts.  I'm not one of those idiots.   I like wearing skirts...
    aquarius3 aquarius3 61-65 4 Responses Nov 22, 2012

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    Related Experiences

    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 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 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 wearing my mini skirts ( see mini skirt album) my girlfriend amber fully supports me dressing up. No there will be no pics of my girlfriend no asking please. I love sitting...
    naughtykevin430 naughtykevin430 41-45, M 1 day ago

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    3rd september 2014, wednesday #my attire to work Wearing a maroon colour knee length figure hugging skirt with a off white long sleeve blouse, blouse tucked under the skirt...
    HotMomShaama HotMomShaama 46-50, F 4 Responses Sep 2

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    11th september 2014; thursday. Wearing a biege colour figure hugging knee length skirt with a off white blouse with blouse tucked under the skirt. Wearing a red thin belt around...
    HotMomShaama HotMomShaama 46-50, F 6 Responses Sep 10

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    Why I Love Fullslips Every woman's body is different. Some have the perfect shape for skirt and sweaters, others are better served by dresses. I am one of the latter. As much...
    slipgirl274 slipgirl274 61-65, F 1 Response Sep 2

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    I haven't tried dresses yet; I'm unsure about my figure. Skirts, though, now we're talkin'! I love the free flowing feel of a long, cotton skirt, or the no-nonsense of denim. Given...
    MollyPetal MollyPetal 41-45, T 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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    Isn't it just the best? Wearing soft female clothes instead of boring male ones? My favourites are tights, skirts and panties.
    Dannjazz Dannjazz 22-25, M 3 Responses 18 hrs ago

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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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    None of my friends or family have any idea but when I get home at night and if I have no prior plans the first thing I do is shower shave or wax if I need it then spend a glorious...
    Jimhes Jimhes 31-35, M 2 Responses 6 hrs 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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    I wish constantly I was female so I could wear dresses and skirts all the time. I wear them as a C D every chance I get and just love how I look and they feel.
    Janae60 Janae60 51-55, M 5 Responses Sep 6

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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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    The way jeans and trousers are made there's almost always a seam under your crotch. Well you need panties on because the hardness of the seam catches your undercarriage and you get...
    Mstroig Mstroig 18-21, F 7 Responses Sep 9

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    Went to work yesterday dressed Felt great walking into the office in a skirt and tights.Most people accept me as a woman apart from old bag who made nasty comments. (I put it down...
    girlynicole girlynicole 36-40, F 9 Responses Sep 16

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    I went shopping the other day, I was looking for a new shirt to go with a skirt I had. I was in my regular male clothing but I did have my bra on with my inserts but not to...
    mat2Robin43 mat2Robin43 51-55, M 1 Response Sep 23

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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 wearing dresses and skirts.
    Cdallaslover99 Cdallaslover99 13-15, M 5 Responses Sep 3

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    I had been working this summer at the rental office of an apartment site owned by my aunt. I always dress nicely for work (as well as school!) and this day I was in my newest white...
    lookingmybest lookingmybest 16-17, F 1 Response Sep 3

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    Love to dress up in tights and skirt with nice top almost anything girly love been girly wish was more feminine I am in away I guess but don't like the idear of getting older :(
    boytightslover boytightslover 22-25, M 5 Responses Sep 9

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    I'm almost exclusively living in women's clothes, now. I have a job where I can work from home a lot, so I only have to put on menswear when I have to go to the office. And...
    KatieTreat KatieTreat 51-55, T 4 Responses Sep 22

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    When I go out with friends or to the mall, I dress for comfort. A lot of times this means a skirt and no panties as I find them restricting. I don't go around flashing people but...
    KrisNudist KrisNudist 18-21, F 5 Responses Sep 22

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    I've done a lot of cross-dressing but I also do some hybrid stuff. I've since started referring to myself as a jane-girl (the opposite of tomboy) and I feel really comfortable...
    beccareuno beccareuno 26-30, F 2 Responses Sep 23

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    Stripes are my fave, preferably worn w/just panties but w/shorts or a mini skirt has 2 suffice when others around.
    ladylox ladylox 46-50, F 2 Responses 3 days ago

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    Hi. I am a 13 year old boy. We live in a apartment with two floors. Both are of us. But the upper one remains locked. Today, I told my mother that I want to take bath. So I took my...
    mylittlebra mylittlebra 22-25, T 2 days ago

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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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