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I Wear Skirts Whenever I Can

For those people who hate wearing trousers 1,043 People

    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 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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    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 3 Responses Sep 4, 2014

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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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    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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    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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    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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    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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    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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    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 1 Response 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 1 Response Nov 12, 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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    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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    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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    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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    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 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'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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    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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    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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    Check out this maker of skirts

    for men. http://www.skirtcraft.com
    Prettyjennifer2004 Prettyjennifer2004 51-55, M 1 Response Jul 15, 2014

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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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    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 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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    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 1 Response Jun 1, 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 1 Response Feb 7, 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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    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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    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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    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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    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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    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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    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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    Related Experiences

    I'm definitely a fan of wearing skirts, particularly the shorter ones. I guess I'm known around my school for having a tight, short skirt. I end up in detention quite frequently...
    LeahUK LeahUK 13-15, F Jan 11

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    I know a lot of girls prefer to wear pants, but for me, skirts are almost always nicer to wear. If you don't wear a fitted skirt, I find my legs can move more easily when I'm...
    YuEvans YuEvans 18-21, F 4 Responses Jan 22

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    I have worn women's clothes since I was very young. About five years ago I decided I didn't want to hide it any more so I came out about it. I approached our HR department and...
    peteorpen peteorpen 61-65, M 1 Response Jan 6

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    I love to wear short skirts and a blouse when going out. Many times, I will wear a short dress or a sundress depending upon the activity.
    middleagedfemalemom middleagedfemalemom 41-45, F 17 hrs ago

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    i am gong to remove my night gown now. Reding to go to work i am going to wear my my wife panty she prefer for me all her cloth that i can wear to my work....... i love her so much...
    daya55 daya55 26-30, M Jan 18

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    I'm having a debate with myself this morning. Tonight is league bowling night. That means guys, bowling and beer. It's a highly testosterone involved environment. I think it would...
    shadowplt shadowplt 51-55, M 9 Responses Jan 15

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    I had to go to the storage unit and drop some things off and pick up some other things. I put on my bra under my Hawaiian shirt on the way over. When I went in the office I think I...
    Sharon03 Sharon03 56-60 7 Responses Jan 9

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    Well yesterday was a fun day. Cleaned the house while wearing my favorite skirt and heels. Played with eye shadow (I really suck at make-up). Watched some movies and did a whole...
    shadowplt shadowplt 51-55, M 2 Responses Jan 11

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    Planning on going to the city this afternoon. I'm going to wear my frilly skirt and heels. My daughter has a swim meet for high school and I want to watch it. Won't wear it at the...
    shadowplt shadowplt 51-55, M 1 Response Jan 13

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    If only I had a skirt, then I could where it all day😀. But I don't, manly because Im not at home so I can not wear my sister stuff😟. I miss that, but this mean I could get my...
    qwerty12474479321 qwerty12474479321 18-21, M 1 Response 2 days ago

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    I really need to buy a skirt so I can sit down and do my work being constable and feel fem. only problem is I don't know where to get one, wear know one would suspect anything...
    qwerty12474479321 qwerty12474479321 18-21, M 1 Response 1 day ago

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    Working remotely has given me an opportunity to dress for work. I don't do it often but today the mood struck me. If only those on the conference calls knew I was wearing this...
    babybearjean babybearjean 56-60, M 6 Responses Jan 15

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    what do you think if world allow us to wear dress outside????
    daya55 daya55 26-30, M 6 Responses Jan 18

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    Today is one of those days I really enjoy. This morning I shaved legs, chest, arm pits, face and neck. Feels wonderful to be smooth. My wife had to work. She's a teacher and has...
    shadowplt shadowplt 51-55, M 4 Responses 5 days ago

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    I'm going to be me today. Whatever that means. Just me. I'll love my wife and kids, enjoy the day as it comes and wear what I feel makes me happy. I'll praise Jesus for the gifts...
    shadowplt shadowplt 51-55, M 2 days ago

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    My wife and daughter went out for lunch with one of my daughter's friend and her Mom. They're shopping down town. I get some skirt time at home and finished doing the laundry. It's...
    shadowplt shadowplt 51-55, M 1 Response Jan 3

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