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I Wear Skirts Whenever I Can

For those people who hate wearing trousers 1,013 People

    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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    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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    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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    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 2 Responses Aug 13, 2012

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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 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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    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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    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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    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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    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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    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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    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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    i love skirts and dresses

    but in high school people call you easy and the pervs try and get behind you on the stairs
    kkkeeennnzzz kkkeeennnzzz 13-15, F 2 Responses Sep 4

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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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    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 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 1 Response Jun 9, 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 1 Response Nov 12, 2012

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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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    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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    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 3 Responses Feb 6, 2011

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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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    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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    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 2 Responses Jun 1, 2012

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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 1 Response Nov 2, 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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    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 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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    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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    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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    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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    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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    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 1 Response Feb 7, 2011

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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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    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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    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 1 Response Nov 29, 2011

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    Related Experiences

    As a man I want to wear skirts all the time. Pants are so boring and can be hot along with being uncomfortable. I think if more men wore skirts in public then society would be more...
    Adam59 Adam59 56-60, M 4 Responses 5 days ago

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    I have been wearing skirts about 3 times a week over the summer and now that it is fall I am still wearing them the only difference is now I wear nylons or leggings with them...
    0hBrandie 0hBrandie 41-45, M 2 Responses Oct 24

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    I am a male and I like my skirts. My skirts are mostly knee length. I find so comfortable to wear. I have pencil skirts and some flowing skirts. I wear my skirts or dresses all the...
    Adam59 Adam59 56-60, M 2 Responses 2 days ago

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    Most definitely a skirt. Skirts are cooler and don't drag on the legs like trousers. Skirts come on a wide variety of styles, colors, and prints. If I given the choice of skirts or...
    Adam59 Adam59 56-60, M 2 days ago

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    Since I had an appointment this morning I had to wear guy clothes. On the outside. Underneath I was wearing panties and a slip. Couldn't get away with a bra today. Now that I'm...
    sharonwoods sharonwoods 51-55, M 4 Responses Oct 29

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    I'm spent. Yesterday I f-up with my wife. She's PO'd at me and won't comment about it. I want to clear things up with her but she's claimed up. My f-up was I was home comfortably...
    shadowplt shadowplt 46-50, M 3 Responses 3 days ago

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    Today I had planned to drive to the city wearing a skirt and doing some shopping. A cold front passed last night and the temperature dropped 30 degrees. Now I'm thinking of getting...
    shadowplt shadowplt 46-50, M 5 Responses Nov 11

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    Added a new twist to my attire: knee length boots I can wear to work!
    shadowplt shadowplt 46-50, M 1 Response a week ago

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    With the snow and earlier bad roads I wasn't able to make my daughter's swim meet today. 😥 Painted my toes and cleaned the house, all while wearing my heels and fav skirt. The...
    shadowplt shadowplt 46-50, M 1 Response 4 days ago

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    Driving into work I have to pass through a security checkpoint. As I offered my ID card, the guard asked me if I owned a kilt. He said he saw someone who looks like me walking down...
    shadowplt shadowplt 46-50, M 3 Responses Oct 23

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    I'm trying something new to me. I purchased some women's panties. I was curious about how they felt. Really it's not different than wearing male bikini underwear. It is fun under...
    shadowplt shadowplt 46-50, M 6 Responses Oct 28

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    Just had a chance to put on a cute new skirt. I've been underdressed all day and now had the opportunity to shed my pants and wear a skirt.
    sharonwoods sharonwoods 51-55, M 3 Responses Oct 31

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    Went to a swim meet today a couple hrs from my house. Wore my red skirt, new heeled boots and panties. As I drove I had the urge to have to use the restroom, whoops forgot to bring...
    shadowplt shadowplt 46-50, M 3 Responses Nov 8

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    A man in a skirt is a man in a skirt. A skirt is a piece of clothing. It does not change your gender or make you more feminine. Men have the rights to wear a skirt if they want too...
    Adam59 Adam59 56-60, M Nov 12

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