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I Wear Skirts Whenever I Can

For those people who hate wearing trousers 1,009 People

    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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    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 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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    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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    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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    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 2 Responses Jun 1, 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 4 Responses Feb 6, 2011

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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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    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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    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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    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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    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 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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    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 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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    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 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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    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 Nov 2, 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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    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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    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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    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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    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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    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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    Related Experiences

    I want to try wearing skirts but I cant :(
    lostgirlboy lostgirlboy 22-25, M 1 Response Apr 5

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    Of Petticoats and Parking Lots When I got married in 1987 the retro fashion of crinoline petticoats had just come into style. I loved the look and comfort of wearing three white...
    BadPam BadPam 51-55, F 3 Responses 3 days ago

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    Yes I do.. Very much so. I love to show off my long sexy legs in short skirts. I do have some long skirts but don't wear them all that much. Most of the time I'm wearing a short...
    TiffanyMarieLeggs TiffanyMarieLeggs 51-55, T 2 Responses 6 days ago

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    Springtime is almost here! I love warm weather and a short or mid length skirt is the perfect thing to wear on a warm breezy spring day. I love having my legs un-covered after...
    shygirl214 shygirl214 18-21, F 5 Responses Mar 24

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    Finally the weather is warming up....time to break out the skirts! My purple jeans mini is the first one I will wear.
    Brandie1960 Brandie1960 41-45, M 6 Responses Apr 1

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    The shorter the better. I have a collection of schoolgirl skirts, and I wear them mostly with kneesocks, and tights at times.
    schoolgyrlKaren schoolgyrlKaren 41-45 4 Responses a week ago

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    This evening I went out shopping guy style....I know what I'm looking for and don't want to spend a lot of time doing it. Went to a discount clothing store looking for boots...
    shadowplt shadowplt 46-50, M 4 Responses Mar 29

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    Had some time before work and went to Walmart to get shaving cream. I shave every day to keep from getting stubble legs and chest. Started shaving my arms too. Legs and chest for...
    shadowplt shadowplt 46-50, M 3 Responses Apr 10

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    Interesting day yesterday . I spent the day wearing knee high hose and regular shoes. (For me regular shoes are what's called "Scrubs") Too cold to wear shorts so I wore jeans a...
    shadowplt shadowplt 46-50, M Mar 24

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    Today I was able to get off work early and wear my skirt and boots. I wore the skirt in my truck and hid it when running errands. Still skittish about being open with a skirt...
    shadowplt shadowplt 46-50, M 3 Responses Mar 26

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    The other day I was wearing some nice work clothes, hose and scrub shoes. My wife commented that the shoes were too casual for my attire. Went to breakfast then looked at what I...
    shadowplt shadowplt 46-50, M 1 Response Apr 8

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    Question: if I wear a skirt under my jeans, boots that are fem with dress pants, that too are fem, and a neutral shirt am I CDing and if so, how do I explain it to my wife? All...
    shadowplt shadowplt 46-50, M 4 hrs ago

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    Today was weird. I had a normal Monday. Up early, Got to work did my job came home. Once home had to take my daughter to guitar lessons then swim team. All the while wearing my...
    shadowplt shadowplt 46-50, M 2 Responses Mar 31

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    Been wearing my flat boots and skirt to work in the past week or so. No one has said anything. Of course I have on guy pants and shirt, but the boots are definitely not "male...
    shadowplt shadowplt 46-50, M 2 days ago

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    Today I discovered something.... People don't care what you wear. They care more about the norm and the stereotypes of society. Went out wearing a floral skirt and boots this...
    shadowplt shadowplt 46-50, M 1 Response 2 days ago

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    Yesterday was a fun day for me. I had a long day wearing my skirt, boots and have added hose to the ensemble. Really liking the feel of hose on my shaved legs. Kinda silky, kinda...
    shadowplt shadowplt 46-50, M 3 Responses Mar 23

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    Some times it's fun to walk the dog wearing a skirt, hose and heels. Didn't get to do that tonight. Just walked the dog. Tonight I get to watch tv, and get up early. Rinse and...
    shadowplt shadowplt 46-50, M 3 Responses Mar 24

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    Went to the downtown area last night. It's an event called First Friday. The downtown square opens its doors for shopping, dinning and socialization. Fun event: music (a band...
    shadowplt shadowplt 46-50, M 1 Response Apr 5

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    I discovered something yesterday....it's fun to bowl in a skirt, even if it's under jeans. I was also wearing hose instead of socks. Makes the bowling shoes more comfortable.
    shadowplt shadowplt 46-50, M 2 Responses Apr 7

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    Another new experience today..... Had to be in a Very public place all day. Wore my short boots, dress pants with a skirt underneath, boy shorts and a nice dress shirt. It was...
    shadowplt shadowplt 46-50, M 1 day ago

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    ;-( leggings decided to rupture at the toes. Had to get a new pair. Bought knee highs and thigh high. Have to admit, thigh highs are comfortable and cover enough leg to look good...
    shadowplt shadowplt 46-50, M 1 Response Mar 20

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    Last night went to a mall store to look for dress pants for work. Found a pair in the women's section that look a lot like guy dress pants only they have a tapered leg towards the...
    shadowplt shadowplt 46-50, M 2 Responses Apr 2

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    Another day blog. Went to work and had a short day. Got home early and had the chance to be home alone. Well you know what that means, Skirt time! Got to spend a few hours alone...
    shadowplt shadowplt 46-50, M 2 Responses Apr 3

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    Added some new photos and am working on more.
    shadowplt shadowplt 46-50, M 6 days ago

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    Especially in the summer! :)
    1234Ideclareathumbwar 1234Ideclareathumbwar 18-21, F 2 Responses 6 days ago

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    Yesterday I went and took a bunch of pictures of being out and about. Kinda scared doing this but at the same time fun to do. I'll try again on another day.
    shadowplt shadowplt 46-50, M 1 Response 5 days ago

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    Mainly I wanted to say that the first picture on this page, the one of both a boy and a girl wearing identical yellow dress costumes was taken by me several years ago at the annual...
    Charlesea Charlesea 70+ 2 Responses Mar 21

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    Im a straight male who has a son and 100 % loves women, but I have this crazy obsession with women's clothing but mainly tights. I hate the fact that I come under the title of a...
    opaquelover100 opaquelover100 31-35, M 5 Responses Apr 11

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