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I Wear Skirts Whenever I Can

For those people who hate wearing trousers 1,023 People

    Lovely, Pink Skirt And Sweater

    My very favorite has always been one of the first outfits I wore. It was in 1966, (I was 14). I used to somehow get up my nerve and go purchase pretty pastel colored FEMININE clothes, from Foundations (Yes Pretty Colored Girdles were in Vouge then), lingerie, bras, and of course...
    carolannP carolannP 61-65, M 3 Responses Mar 21, 2011

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    Of Course I Wear Skirts Whenever I Can!

    Why wouldn't I.... they are sooooo much more fun to wear than pants! I think they look better on me than pants - they give me more of a feminine shape, allow me to walk and sit much more feminine-like and feel so good the way the move around my legs as I walk and sit. I wear a...
    terr01 terr01 31-35, M 3 Responses Mar 30, 2011

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    The Appointment

    I have an appointment with my doctor tomorrow and am, as always, fretting about what to wear. We are going to discuss whether or not I start on female hormones and I really want to make a good impression, so do you think I should wear a simple skirt and blouse or go with my red...
    PinksWoman PinksWoman 61-65, T 10 Responses Oct 30, 2012

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    I Do

    i have had a fascination with skirts and dresses since i was 6 years old as i drive a truck i can wear a skirt most times. it gets a little tricky sometimes but that is half the fun
    deleted deleted 26-30 1 Response Jan 14, 2012

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    Love Skirts

    Also love skirts and wear them when ever it is possible
    frieda123 frieda123 31-35, F 1 Response Aug 12, 2012

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    Every Oppertunity

    i like nothing better than to be able to ***** of my male garb and don a dress or a skirt. often i will use the excuse of having to do some correspondence for the business which means using my computer, which happens to be in my bed room. i will lock my door behind me and...
    Cyclopes66 Cyclopes66 51-55, M 2 Responses Oct 9, 2011

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    I Wear Skirts

    At the age of 23 after just wearing pantyhose for many a year I decided to buy a skirt & top along with a matching bra & pantie set, on getting home I went straight to my bedrrom & got changed in to my girly clothes & it felt great to be fully dressed as a woman for the first...
    xdpaul xdpaul 56-60, M 1 Response Jun 5, 2011

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    I Find Comfort In A Skirt

    I started wearing womens clothes years ago. It started with nylons and slips. My wife now knows that I wear womens clothes but does not like it much, so I do not wear them when she is home. Fortunately she works evenings so when i get home from work and on weekends when I can I...
    whynot4u whynot4u 51-55 2 Responses Jan 15, 2011

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    Love Wearing Skirts

    I wear skirts whenever I possibly can. I have many in my wardrobe. I prefer the flexability of a skirt and blouse over a dress for most occasions. Around the house I love wearing short cargo skirts in the summer, much cooler and very practical over shorts or capris. In...
    Shawnaroo Shawnaroo 56-60 Nov 1, 2012

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    So Do I

    I work in a smallholding growing vegetables and also  in a pub and I'm lucky, because in both jobs I can wear a denim skirt, which is what I like best. For farm work, skirts are mor practical and comfortable than pants, and that's what people on the land have always worn. In the...
    alanrunner alanrunner 26-30, T 4 Responses Jan 26, 2011

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    Sad Truth

    I am just starting my sixth week of living full time as a female and have made some interesting discoveries. When I began, it was a real rush, practicing my makeup, dressing up all girly, all the time, sitting, walking, even practicing my female voice. I was a little...
    PinksWoman PinksWoman 61-65, T 7 Responses Oct 27, 2012

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    The Maid

    I have the maid in today to clean up the place, do the laundry and the dishes. She is wearing a knee length black skirt, a ruffled white blouse, a little lipstick and small earings, don't want them to get caught on anything. 2" black strappy shoes, panties, pantyhose and...
    PinksWoman PinksWoman 61-65, T Oct 7, 2012

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    It's A Natural For Me

    I wear skirts and even dresses often because for me it makes me feel pretty. I love they way they look and I love how feminine I feel when I wear them.Sometimes when I wear a skirt, if it is shorter than knee length, I wear shorts underneath and in doing so I feel more...
    Josie06 Josie06 56-60, F 1 Response Dec 3, 2011

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    Dresses And Skirts

    I have been laid off for over 2 years, and have been wearing either a dress or skirt every day!  I love nylon granny panties, pretty bras, full nylon slips, hose and either pumps or flats!  It would be a dream for a woman to do a makeup makeover on me while dressed!
    OhioSissy OhioSissy 51-55, M Sep 7, 2011

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    Me Too

    I am a lifelong crossdresser who recently decided to feminize myself and live full time as a woman for the rest of my life. I have been doing so for almost a year now, and love to wear skirts and dresses in my apartment, I dress discretely in public however. I usually wear...
    PinksWoman PinksWoman 61-65, T Sep 30, 2012

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    Today And Tomorrow

    I am in toal agreement with all in this group. I no longer own or wear pants and I am a male. There is nothing more comfortable then a skirt, short of a dress of course. Then again what is a dress but a skirt with the top attached, no need for matching the wardrobe. I wear my...
    Melodie13 Melodie13 61-65, M 3 Responses Nov 8, 2010

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    Someday

    I prefer skirts over dresses most of the time, flouncy skirts that flare out when I spin around. I wear them every day in my apartment but as yet have not found the courage to wear one in public. I hope to have a complete feminine makeover for Halloween and wear both every day...
    PinksWoman PinksWoman 61-65, T Oct 1, 2012

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    I Wear Skirts Whenever I Can

    Now the dark nights are coming and closing in quickly it means I can wear skirts nearly all the time at home.  No need to wear uncomfortable trousers - just skirts every night now.
    deleted deleted 26-30 4 Responses Oct 16, 2010

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    I Love Skirts

    If It were up to me. I wouldn't wear anything else.
    Karalee2 Karalee2 51-55 3 Responses Jun 14, 2012

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    I Love It

    Oh I so love to wear my skirts. if I could I would wear them all the time. I feel so good in a skirt. Very rarely do I wear my skirts without panty hose and a half slip. To sit with my legs crossed talking to my wife is a real treat. Walking around the house in my skirts and...
    Adam59 Adam59 56-60, M 3 Responses Aug 13, 2012

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    Skirts Rock

    there is nothing better than coming home from work putting on panties and a bra then pantyhose then slipping into a short skirt.its heaven.
    aprilwalls aprilwalls 46-50, T 8 Responses Dec 27, 2010

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    Mini Skirts.

    I love to wear a mini skirt whenever possible, as during my working day I am usually wearing dirty , dusty overalls, so the feeling of the hem of my short skirt floating around my thighs, and the cool air is just so nice and also it just feels right somehow too. Plus it doesn't...
    roadtooblivion roadtooblivion 56-60, M Aug 12, 2012

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    To Be Honest I Have To For Work

    I work for a jewish school an orthodox jewish school. I have to wear skirts that come to my knee tops that cover all the way to my elbow. But years before that I wore skirts all the time I wore them every chance I got and I look really really good in them. The change into a...
    Starbuck82 Starbuck82 26-30, F 2 Responses Nov 12, 2012

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    I Do

    ...and it's becoming more often.My wife accepts that I do; so long as I keep it in the house (apt).She's away for the weekend. So, early this morning, I took the opportunity to venture out.I took the dog for a walk across the grounds. There are 5 buildings in the complex, with...
    JosetteLaRoc JosetteLaRoc 36-40 2 Responses Jun 9, 2012

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    I Love To Wear Skirts Too

    I have always loved to wear skirts ever since I was 7 or 8 when I put on my sisters skirt I love the feeling of the skirt against my skin and the freedom it gives me. I wear them now every chance I get when I'm home from work. I love doing the cooking and cleaning whilst wearing...
    scutty68 scutty68 41-45 2 Responses Feb 7, 2011

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    I really prefer to wear a skirt over pants,

    I just feel they are more comfy, pants are to confining.
    fireyes fireyes 22-25, F Apr 17

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    I Want To All The Time

    I want to wear skirts all the time. However, it is not accepted to wear them in public. So I wear them at home all the time. Hopefuy someday we will wise up and men will be able to be equal to women and wear our skirts out in public too.
    Adam59 Adam59 56-60, M 1 Response Jun 14, 2012

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    Pencil Skirts

    i love them, i love the way i have to hobble and mince around in them like a real sissy should. i have several skirts from mini to calf length and i adore them all i only have 1 dress and its a mini that just covers my butt and its sexy as hell. i love going to the thrift stores...
    Mizsuzy Mizsuzy 46-50, T Nov 29, 2011

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    Skirts Are Great

    What is not to like about a skirt. It has everything - variety, comfort and convenience all at once. A skirt is appropriate for every occasion and with careful selection the same skirt works for the office and clubbing after work without any need to stop and change. Just...
    Paulypeeps Paulypeeps 36-40 7 Responses Jun 10, 2013

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    Check out this maker of skirts

    for men. http://www.skirtcraft.com
    Prettyjennifer2004 Prettyjennifer2004 51-55, M 1 Response Jul 15

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    Unwinding In A Skirt

    At the end of a work I like to wear a skirt to unwind. All day long I make decisions. As a fire inspector people come to me looking for direction, wanting answers or raising questions that require research. By the end of the day or on the weekend I find that I can mentally relax...
    whynot4u whynot4u 51-55 4 Responses Feb 6, 2011

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    Question

    Why is it that as a woman I am so fastideous with my femine clothes when I was such a slob as a guy?
    PinksWoman PinksWoman 61-65, T Sep 30, 2012

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    I Hate Trousers But Not Shorts

    I like to wear both skirts and shorts. I dont like trouser though. Sometimes it's not easy to decide between a cute skirt and shorts! And I only like them with bare legs, I hate tights. It's so good to feel the air touching the bare skin on your legs.
    annabellalucas annabellalucas 18-21, F 1 Response Nov 2, 2012

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    My Time Wearing Skirts

    my wife is an exec at her co. and dresses in skirts all the time thats how i got into wearing them
    jeanettecd jeanettecd 51-55, M 5 Responses Sep 27, 2012

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    I'd Do It More, Too...

    ...if our personal finances allowed it. Preferably, I would like to always wear dresses or skirts, and never wear capris, pants, or shorts of any kind. I find them to be far more feminine than anything else out there to wear today. The only thing I find to be more feminine is...
    AmericanLeanings AmericanLeanings 31-35, F 3 Responses Aug 28, 2011

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    24-7 Skirts

    I always think what would happen if my pants ripped. So that's why I always where my skirts underneath Stealth skirts can't see em coming. And for me: just having one on calms da nerves.
    pieante pieante 51-55, T 3 Responses Nov 2, 2012

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    My Favourite Skirts

    My favourite skirt has to be the pencil skirt its elegant restricts movement and helps me walk like a lady. I also like to wear a knee length or calf length loose fitting skirt one that flows with you as I walk the freedom this gives is sooooo good. I also love to wear black...
    scutty68 scutty68 41-45 1 Response Feb 9, 2011

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    Chairman Wears A Skirt

    Recently I attended an AGM as chairman. I wore a skirt for the whole day. Of all the people there, only one comment from a teenage girl. "is that a skirt you're wearing", reply "yes it is", and that was it. I guess everybody knows about my skirt wearing now. Very happy!
    Prettyjennifer2004 Prettyjennifer2004 51-55, M 5 Responses Jun 1, 2012

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    Related Experiences

    I think men should wear whatever they want to wear. Skirts are cooler in hot weather. As long as the clothes are well fitting and look nice what does it matter what any one wears...
    renah64 renah64 61-65, T 1 Response Jul 20

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    Yesterday I decided I would change into my skirt at work. I just happened to have one in my briefcase, well, you do, don't you?! So I walked through the office and out into the car...
    Prettyjennifer2004 Prettyjennifer2004 51-55, M 3 Responses Jul 19

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    Had to see a Dr today so I can see another Dr tomorrow. I have cancer for the third time. It's a form of skin cancer that's very treatable. Caught early it's not a problem. Does...
    shadowplt shadowplt 46-50, M 4 Responses 5 days ago

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    I love wearing skirts :) I never wear panties with then though.
    starfire007 starfire007 13-15, F 7 Responses 2 days ago

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    What a wonderful day. My wife was out of town all day. My son worked and I had the house to myself....besides the dog and cat. Got to wear my skirts and heels all day. Worst part...
    shadowplt shadowplt 46-50, M 1 Response Jul 13

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    My wife was miffed at me today. I thought it was because I was wearing a skirt last night. Turns out she had a beef with how I was discussing living arrangements with my 23 yr old...
    shadowplt shadowplt 46-50, M 7 hrs ago

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    I have just discovered this maker of skirts for men http://www.skirtcraft.com Check it out!
    Prettyjennifer2004 Prettyjennifer2004 51-55, M Jul 15

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    Check out this maker of skirts for men. http://www.skirtcraft.com
    Prettyjennifer2004 Prettyjennifer2004 51-55, M 1 Response Jul 15

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    Check out this maker of skirts for men. http://www.skirtcraft.com
    Prettyjennifer2004 Prettyjennifer2004 51-55, M Jul 15

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    Check out this maker of skirts for men. http://www.skirtcraft.com
    Prettyjennifer2004 Prettyjennifer2004 51-55, M 1 Response Jul 15

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    Am I the only one who feels like someone should be able to do whatever they want to? Why can men not wear make up, dresses, pink etc without being told they are gay? Which makes...
    AnomalousEarthling AnomalousEarthling 22-25, F 12 Responses Jul 19

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    Well the wife and kids are away and I have the place to myself. Time for skirts, boots and a movie!
    shadowplt shadowplt 46-50, M 4 Responses 4 days ago

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    This weekend my daughter competed in the Oklahoma USA Age Group swim meet. She did absolutely great! One proud dad. Traveling there and home I had the opportunity to wear my...
    shadowplt shadowplt 46-50, M 5 Responses 1 day ago

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