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I Like to Wear Skirts

Personal Stories, Advice, and Support 2,375 People

    Today I had an amazing epiphany,

    people don't really care about what your wearing. I drove to another city in my state. I was wearing my skirt and heeled boots. Nothing unusual. Most people can't see into my truck and view what I'm wearing. I got to my hotel and was tired so I went inside to check in wearing...
    shadowplt shadowplt 51-55, M 1 Response Oct 3, 2014

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    shadowplt shadowplt 51-55, M 1 Response Jan 11

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    Skirts

    I have a large selection of skirts in all styles and lengths made of a variety of materials.I have a number of flared mini skirts that look great with seamed stockings, they always turn a few heads.I have to the knee demure skirts for work.Generally I find skirts a very versatile...
    sally1981 sally1981 31-35, F 25 Responses Dec 27, 2011

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    This picture is how I presented yesterday on my

    trip to the city. I had a very wonderful day.
    shadowplt shadowplt 51-55, M 1 Response Dec 31, 2014

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    Found this yesterday at a discount store.

    I really like the material. It's very satin feeling. I'm liking it very much. Extends the feeling to the chest. Now I just have to find a necklace.
    shadowplt shadowplt 51-55, M 5 Responses Nov 21, 2014

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    I like to be naughty some days

    and go without panties. It is a rush when you know something that no one else knows. Especially when it a naughty one. I like to sometimes be a lot more naughty and in public I will slowly uncross my legs to change legs crossed. Nothing like a small tease.
    kittyluv78 kittyluv78 36-40, F 14 Responses Oct 1, 2014

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    Well I tried on my first skirt today in 10 years

    and I wanted to know what y'all think about this outfit that I might get
    Karianne6614 Karianne6614 16-17, F 25 Responses Jul 30, 2014

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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 park to my car. I drove home and when I got home and was greeted by my wife she just said, oh, a skirt at work today? I said yes. Later we...
    Prettyjennifer2004 Prettyjennifer2004 51-55, M 5 Responses Jul 19, 2014

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    I drove to the city in my favorite skirt

    and heeled boot as I've done many a time. I usually stop at a convince store to use the restroom. It's normally not very crowded but for some reason there were about 20 people in the attached Subway restaurant. Needless to say I was hesitant to go in, my bladder said otherwise...
    shadowplt shadowplt 51-55, M 4 Responses Jan 18

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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 lot of nothing. I did go out for lunch wearing my heeled boots. Got a few double takes from some ladies at the restaurant. I found...
    shadowplt shadowplt 51-55, M 2 Responses Jan 11

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    To all my friends and future friends here on EP,

    wishing everyone a Happy New Year. I hope everyone has their dreams and wishes come true this 2015. I'm going to work on mine. I want to strengthen my marriage, learn to incorporate my desire to dress with what my wife's comfortable with and support her desires.
    shadowplt shadowplt 51-55, M 3 Responses Jan 1

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    My daughter and wife are traveling to a swim

    meet today. I opted to stay home and clean the house/rake leaves. Going to do it dressed and heeled. Looking forward to just being myself, watching movies and having some me time. I'll let everyone know how the day went.
    shadowplt shadowplt 51-55, M 3 Responses Jan 10

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    shadowplt shadowplt 51-55, M 1 Response 6 days ago

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    Skirts And Ts

    I love skirts and dresses so much more than a pant. However, wearing a pant is a bit of a right of passage for TS's as our bodies are not shaped exactly correct and it takes us a long while to achieve the shape which is so prominently displayed in a tight pant. After many years...
    LapiudolceTS LapiudolceTS 36-40, T 5 Responses Jun 14, 2012

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    Well, I did it. Wore my red

    and black ankle length skirt into the airport and thru TSA security zone. Boarded the plane and flew to one of the busiest airports in the US. Chicago O'Hare. Finally flew from there to Va. All this time dressed in skirt and heels. No one said anything to me. I know that I got...
    shadowplt shadowplt 51-55, M 4 Responses Oct 12, 2014

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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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    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 being stuck in jeans and pants all winter, and I love to feel the wind and the warmth of the sun on my knees. Also, I have to...
    shygirl214 shygirl214 18-21, F 12 Responses Mar 24, 2014

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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 back home I can get rid of the pants and put on a skirt. I'll also put on a bra and nice sweater.
    sharonwoods sharonwoods 51-55, M 4 Responses Oct 29, 2014

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    Yippee! Another evening walking in my local

    town in my skirt. Very happy. Very confident.
    Prettyjennifer2004 Prettyjennifer2004 51-55, M Jul 21, 2014

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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 make me feel human and not really care too much what others think about my dressing. I know I'll probably not live to 100...
    shadowplt shadowplt 51-55, M 5 Responses Jul 23, 2014

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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 amazing how much I can't properly sort my wife's and daughter's clothes. I know my stuff (both male and female), but theirs...
    shadowplt shadowplt 51-55, M 1 Response Jan 3

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    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 for incorrect uniform, having my skirt too high and short. The new skirts are designed to stop us from folding them up, however we are able...
    LeahUK LeahUK 13-15, F Jan 11

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    Well a nice day has gone south.

    My wife has told me she's given me time to be me. That's why she's working extra hours and doesn't want to spend time with me. She doesn't like my CDing. I'm guessing I need to choose between how I feel about her and my desire to CD. To me there's no real choice, I have to lose...
    shadowplt shadowplt 51-55, M 5 Responses 5 days ago

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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.
    0hBrandie 0hBrandie 41-45, M 6 Responses Apr 1, 2014

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    Going to the city today.

    Plan on going enFem all afternoon. My wife actually suggested I go today since she has to work. She knows (without saying it to me) that I'll dress and told me to enjoy the shopping. I'll post a picture on my journey.
    shadowplt shadowplt 51-55, M 2 Responses Dec 30, 2014

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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 ๐Ÿ˜Ÿ. I gess I would all so want some tights and maybe a to as well๐Ÿ˜€.
    qwerty12474479321 qwerty12474479321 18-21, M 1 Response 1 day ago

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    Nerd in a skirt. Not really.

    But I love to read and this skirt is so pretty. Love the buttons and pattern.
    SPIDERLIMBS SPIDERLIMBS 16-17, F 3 Responses Jan 5

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    Another unique experience.

    I was going home after work as usual. I got my go home soda and as I usually do, I took my slacks off to cruise in my boots and skirt. ( I wear a skirt under my work slacks ) I happened upon an accident between two cars and stopped to help. It's a usually busy intersection and...
    shadowplt shadowplt 51-55, M 3 Responses Jul 22, 2014

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    Spent the day dressed around the house.

    Heels, skirt and a nice blouse. Didn't really do much, just a day of relaxation. Something struck me. Why can't people be like our pets. My dog and cat just look at me and wag their tails wanting love and food. They don't judge us or critique us. They just accept us the way we...
    shadowplt shadowplt 51-55, M 2 Responses Aug 3, 2014

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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 caught the receptionist checking out the bulges in my shirt a couple of times. Then I went out back and changed into a skirt and...
    Sharon03 Sharon03 56-60 7 Responses Jan 9

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    To all my EP friends

    and circle, a huge thank you. I've appreciated the candor and comments I get. I'm feeling better about myself and my famine side because of you all. I'm not trans, gay or otherwise anything but a guy who likes to be famine. I trust your advise no matter what your desires. God...
    shadowplt shadowplt 51-55, M 1 Response Jan 11

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    I'd arrived late to this week's PE lesson due

    to long queues at the girls' bathroom. I ended up sharing a cubicle with a lad in their bathroom, I honestly couldn't hold it any longer, I was so desperate. I was told to head straight for the gym instead of changing into my PE outfit, and was told to join is as usual with the...
    LeahUK LeahUK 13-15, F 1 Response Jan 13

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    My after work attire

    while doing a whole lot of nothing at home.
    shadowplt shadowplt 51-55, M 1 Response Jan 5

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    An exceptional thing happened today.

    I wore mascara to work along with my heeled boots. Everything else was normal; dress slacks (skirt underneath) a nice shirt ( women's blouse that imitates a man's dress shirt) not one word from my co-workers. Every time I change a little and no one notices or says something...
    shadowplt shadowplt 51-55, M 3 Responses Aug 22, 2014

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    The married man I'm seeing loves me to turn up

    in a short skirt and no knickers so he can **** me straight away!
    sexysahra79 sexysahra79 31-35, F 3 Responses Apr 24, 2014

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    Yesterday was a weird day.

    I had to work very early so I could take my daughter to an appointment. That meant I got off work early and had the rest of the day to myself. Got to dress and lounge around the house. I played with make-up. Still not comfortable with it. It's hard to put on and even harder to...
    shadowplt shadowplt 51-55, M 3 Responses Jan 7

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    daya55 daya55 26-30, M 6 Responses Jan 18

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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 He's given me and love life as He's designed it for me.
    shadowplt shadowplt 51-55, M 1 day ago

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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 7 hrs ago

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    Tonight is a good night.

    Had a fun day raking leaves and being a guy. Played with my dog. He loves leaf piles. Hides his ball in them and pretends he's forgotten where it is. Got inside and warmed up by getting on my fav skirt and boots. Sat on the couch all curled up and just vegged.
    shadowplt shadowplt 51-55, M 1 Response Jan 1

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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 pool (too many people I know), but otherwise I'll be dressed enfem. Looking forward to a little me time.
    shadowplt shadowplt 51-55, M 1 Response Jan 13

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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 be fun to wear a skirt to bowl in and make a fun joke of it. Of course, I'd be the one at the brunt of the jokes and the one having fun doing it...
    shadowplt shadowplt 51-55, M 9 Responses Jan 15

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    shadowplt shadowplt 51-55, M Jan 11

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    Skirt Appreciation

    I wore my first skirt when I was about 9 or 10. The feeling was incredible! My brother and I were playing dress up with my sisters. I have tried to recreate that feeling over the years with varying degrees of success. I have come to feel that skirts are wasted on women. They...
    Sharon03 Sharon03 56-60 2 Responses Aug 6, 2012

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    I was seen by a coworker this morning with a

    skirt on. I went to work early so I was the first one there. As the first one in the building I had to go and turn off the alarm system. As I was loving into the computer and my back was to the door another employee walked in. He just said, morning. And turned to go down the...
    mat2Robin43 mat2Robin43 51-55, M 8 Responses Jan 9

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    pinkleatherpants pinkleatherpants 22-25, F 7 Responses May 20, 2014

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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 wearing a skirt, maybe because the fabric's not trying to stay still on my legs? I also really like the... "ventilation" one can get with a skirt...
    YuEvans YuEvans 18-21, F 4 Responses Jan 22

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    starfire007 starfire007 13-15, F 13 Responses Jul 26, 2014

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    Ok, I'm a happy camper this afternoon.

    Went to work and wasn't scheduled for a single simulator mission. So.....I took the afternoon off, went home and am sitting on my sofa watching tv while enjoying the comfort of a nice skirt and boots. I'm becoming more comfortable dressed this way than not. It's kind of scary...
    shadowplt shadowplt 51-55, M 6 Responses Nov 19, 2014

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    Well I'm back from my trip to the city.

    Left the house dressed for power shopping. Since it's suddenly really cold I had to wear black tights under my ankle length skirt. Those can get pretty warm in a heated truck. Walked throughout the mall dressed from the waist down. Heeled boots clacking as I went from store to...
    shadowplt shadowplt 51-55, M 2 Responses Dec 30, 2014

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    Tonight was a total success.

    After dinner as it got dark, I told my wife I was going out to chill and relax. We have a two mile walking path nearby. I drove to it wearing my new skirt. I had on my heeled boots and a t shirt. Walked the path. Passed several couples and individuals, the only comment I got...
    shadowplt shadowplt 51-55, M 4 Responses Sep 22, 2014

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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.