Post

I Am Wearing A Skirt

Personal Stories, Advice, and Support 813 People

    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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    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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    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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    My favorite skirts are my schoolgyrl plaid

    skirts. I have a red, pink, green, and kaki.
    schoolgyrlKaren schoolgyrlKaren 41-45 3 Responses Apr 12

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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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    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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    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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    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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    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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    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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    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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    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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    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 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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    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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    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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    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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    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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    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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    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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    OK... Google the phrase "shopping tunic", then click the "shopping" tab. You'll see that pretty much all the results are for "women's tunic dresses". Then search "gladiator sandals...
    steve66oh steve66oh 46-50, M 6 Responses Aug 11

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    Back in high school I would wear shorts on the winter but I'm excited for this winter to stop wearing shorts and start wearing skirts! Also I usually hate winter and the snow but I...
    Alexis117 Alexis117 18-21, T 1 Response Aug 6

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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 Aug 17

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    14th August 2014, thursday Wearing a black knee length figure hugging skirt with a purple long sleeve blouse with blouse tucked under the skirt Wearing a thin black belt around...
    HotMomShaama HotMomShaama 46-50, F 3 Responses Aug 13

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    25th august 2014, monday Wearing a black figure hugging knee length skirt with a red blouse with blouse tucked under the skirt, wearing a thique black belt around my hips with a...
    HotMomShaama HotMomShaama 46-50, F 3 Responses a week ago

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    7th August 2014, thursday Wearing a maroon colour knee length figure hugging skirt with a black blouse with the blouse tucked under the skirt, carrying a black handbag, wearing...
    HotMomShaama HotMomShaama 46-50, F 2 Responses Aug 6

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    When I was a teenager I loved wearing miniskirts. In fact I used to wear them as much as possible in preference to jeans, etc. to show off my legs. My mum used to let us wear...
    Jilly53 Jilly53 56-60, F 1 Response Aug 14

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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 7 Responses Aug 21

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    I just find them so comforting and exhilarating. As you can read in some of my other stories, it began with bras as a pre-teen and grew slowly over the years. Now that I live on...
    LockedDarius LockedDarius 26-30, M 2 Responses Aug 21

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    I did it today! I wore my skirt in public in heeled boots! :-) It wasn't for long. I've done this before in the dark, but not on purpose. Today was a conscience decision. I...
    shadowplt shadowplt 46-50, M 8 hrs ago

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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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    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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    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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    19th August 2014, tuesday Wearing a grey colour figure hugging knee length skirt with a dark blue blouse, carrying a silver colour handbag, wearing white coat shoes, wearing a...
    HotMomShaama HotMomShaama 46-50, F 4 Responses Aug 18

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    27th august 2014, wednesday Wearing a long white loose skirt which is embroidered with a light purple blouse with white dots on it, Wearing a white tanga panty and a white bra...
    HotMomShaama HotMomShaama 46-50, F 2 Responses 5 days ago

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    Just the other day I saw a lovely little lady in Walmart. It was a hot day and she was wearing a floaty mini dress with a low back, down to her waist and very thin straps over her...
    MarieJosephe MarieJosephe 66-70, M 8 Responses 4 days ago

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    I have worn dresses or skirts since i was 6 but i would love to live in a world where a boy can wear them openly instead of having to be called a cross dresser. i hope that day...
    jamie172 jamie172 46-50, T 9 Responses Aug 4

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    A little conversation with my 3 year old daughter the other day. She was wearing a pretty little dress, spinning round so the skirts puffed out. She looked so cute. She turned to...
    Heellover Heellover 36-40, M 9 Responses Aug 8

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    I loved wearing miniskirts as a teenager and a young woman. I wore them in preference to jeans or trousers where possible. However, they did have their own hazard! One day, when we...
    Jilly53 Jilly53 56-60, F 5 Responses Aug 16

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    I'm Pentecostal so I have my reasons. Besides my religion, I enjoy wearing dresses and skirts instead of pants. Pants are so uncomfortable.
    PeaceBatman PeaceBatman 22-25, F 5 Responses Aug 16

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    Tonight I'm wearing a skirt to bed. Wonder what My wife well feel.
    shadowplt shadowplt 46-50, M a week ago

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    I went walking around town in a skirt, and I the sidewalk was getting crowed so I moved over and slipped on the side and fell! My but was in the hair and at least 20 people saw my...
    DoubleDirtyPanties DoubleDirtyPanties 18-21, M 2 days ago

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    My wife has me wearing matching satin Cacique bra and panties with black nylons, black flirty skirt, red top and my red 4" heels. Also all made up with a my brown curly wig and...
    nikkifemmdslave2 nikkifemmdslave2 36-40, M 4 Responses Aug 12

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    Isn't it amazing that a single moment in time can flip a switch inside of us and nothing is ever the same? I can think of a hundred things that might have affected me in a...
    kayleew2000 kayleew2000 18-21 14 Responses Aug 16

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    I can't wait to get home from work and get out of my work clothes. I take a shower and shave all my body hair. I then get out and lotion all my body. Then I pick out panties and...
    Michelle1976 Michelle1976 36-40, T 6 Responses Aug 16

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    I think I do..... For about a year or so, with the exception of my school uniform, that's all I've worn.... I'm so used to them now that it feels strange not wearing one...
    SarahTheHooker SarahTheHooker 18-21, F Aug 20

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    When I grew up I did at least in private and sometimes not so private wear short pleated skirts and the occasional pinafore style dress. This was not a punishment and indeed I am...
    littlegreyshorts littlegreyshorts 51-55, M 4 Responses Aug 1

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    Especially with a skirt... nothing like the freedom of a fresh breeze :)
    ultimatebeanstalk ultimatebeanstalk 36-40, F 14 Responses Aug 2

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