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I Like to Wear Skirts

Personal Stories, Advice, and Support 2,223 People

    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 some tights to wear underneath before I go.
    shadowplt shadowplt 46-50, M 5 Responses Nov 11

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    Today my wife and daughter traveled to another

    town for a swim meet. I stayed home because I was officiating a YMCA swim meet here in town. This afternoon I got to wear my new dress. Tried a little eye shadow. Don't really like it so it's coming off, but not the dress. At least until tonight when they come home.
    shadowplt shadowplt 46-50, M 2 Responses 2 days ago

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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 male clothes (except that for what I needed to officiate in). Went into a convenience store and the men's restroom was occupied. The clerk...
    shadowplt shadowplt 46-50, M 3 Responses Nov 8

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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 4 Responses Aug 6, 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 46-50, M 4 Responses Oct 12

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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 46-50, M 3 Responses Jul 22

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    Question for all: how do I determine

    if I'm trans or not? I really enjoy being feminine but at the same time like being a guy. Makeup, hair styles and appearance matter now, but comfort of jeans and make dress clothes do too. Just curious. I know many of my friends are TG. Please help.
    shadowplt shadowplt 46-50, M 3 Responses 1 day ago

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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 46-50, M 3 Responses Aug 22

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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 23 Responses Jul 30

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    To all who follow my posts: thank you all๐Ÿ˜ I

    really appreciate your comments, advice and comment to this experience. I'm a guy and I I like to feel pretty from the waist down. Thanks for the support!
    shadowplt shadowplt 46-50, M 2 Responses Nov 14

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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 46-50, M 5 Responses Jul 23

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    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 46-50, M 1 Response Oct 3

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    Well a follow-up to my post yesterday.

    OMG! We had the most wonderful conversation yesterday evening. She asked me many questions about what she knew I was doing and I truthfully answered. There wasn't an argument or yelling or anything other than us two discussing where we go from here. I'm so happy! I know she's...
    shadowplt shadowplt 46-50, M 4 Responses 6 days ago

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    As I go to bed tonight,

    I'd like to thank those that have responded to my previous posts. It's heartwarming to know you all are out there and have had similar experiences. This is what I like about EP. Good people thought the world regardless of past or nationality coming together. As Mr Spock said...
    shadowplt shadowplt 46-50, M 1 Response 5 days ago

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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 46-50, M 2 Responses Aug 3

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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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    I am getting ready to leave

    for a trip. I have a 300 mile drive to do and I plan on having my new skirt and blouse on the whole time. I may stop at a dress shop on the way also. This is going to be a fun drive.
    mat2Robin43 mat2Robin43 51-55, M 3 Responses Jul 20

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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

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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 24 Responses Dec 27, 2011

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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

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    starfire007 starfire007 13-15, F 13 Responses Jul 26

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    Best place to be right now.

    ...lounging in bed, wearing a skirt, watching the news while my wife and I get ready for work. Going to try wearing some mild eye shadow and mascara to work. Hopefully I can pull it off.
    shadowplt shadowplt 46-50, M 4 Responses 14 hrs ago

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    Went to the swim meet.

    Daughter smoked it today. Very proud of her. I did dress for the trip and throughly enjoyed the feeling of a skirt swishing in the breeze as I went into convince stores and other places.
    shadowplt shadowplt 46-50, M Nov 15

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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 46-50, M 6 Responses 3 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

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    Well winter has arrived here in the mid-west.

    Having our first snowfall of the year. Expecting 1-2". Had to put on leggings under my skirt to keep warm. The real bummer is I can't feel the swishing and flow of the material. No breeze up the skirt either. ๐Ÿ˜ฅI've also discovered that heels don't do so well in snow. A little...
    shadowplt shadowplt 46-50, M 4 Responses Nov 16

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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

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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 46-50, M 7 Responses 5 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 evening. At a convenience store filled my truck and no one batted an eye lash. Felt scared and thrilled at the same time.
    shadowplt shadowplt 46-50, M 1 Response Apr 17

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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 favorite skirt and boots. What a thrill to know what I'm wearing and feeling comfortable in it. Even went to the gas station to fill up my...
    shadowplt shadowplt 46-50, M 5 Responses Jul 27

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    I like to wet my panties

    while wearing a mini skirt
    mischef mischef 41-45, T 1 Response 15 hrs ago

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    I want to so much come out to my wife

    and be totally honest. She doesn't approve of my dressing but I so much want to be able to. I love her so much, I hate hiding but I also hate disappointing.
    shadowplt shadowplt 46-50, M 2 Responses Nov 16

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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

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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 46-50, M 4 Responses Sep 22

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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

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    Today I'm a little depressed.

    Nothing serious, just wanting a weekend free to do as I want and not have to obligate to others. That's not going to happen, so I press on and enjoy the moment.
    shadowplt shadowplt 46-50, M 3 Responses Nov 14

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    Dressed this way the entire day.

    Even going out for dinner this way. I'm having a fun girl day.
    shadowplt shadowplt 46-50, M 2 Responses Nov 16

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    With the snow and earlier bad roads I wasn't

    able to make my daughter's swim meet today. ๐Ÿ˜ฅ Painted my toes and cleaned the house, all while wearing my heels and fav skirt. The down side, can't remove the toe paint. Something about the nail polish remover isn't working. I'm stuck until time removes it.
    shadowplt shadowplt 46-50, M 1 Response Nov 16

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    Just wondering something.

    ..I've been listening to a hypnosis recording about feminization and how to (not convert) become more feminine. I really enjoy wearing the clothes and mannerisms, but want to remain masculine in my thoughts. Does anyone think the hypnosis is actually taking? I usually listen...
    shadowplt shadowplt 46-50, M 1 Response 3 days ago

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    shadowplt shadowplt 46-50, M 1 Response Nov 13

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    Today was a work day.

    Getting braver. Wore a skirt to McDonalds. Bunch of older folk there at the time. Whoops. A co-worker walks in and sees me. We converse and at work nothing was said or strange looks. I of course, being quite embarrassed, changed into guy clothes before getting to work.
    shadowplt shadowplt 46-50, M 2 Responses Aug 12

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    Yesterday I found something I'd never thought

    I'd like, a dress. I went into the store just casually looking over clothes. There on the rack was a dress that was made of a material I enjoy. I quickly looked it over and to my surprise, it was my size. I took it to the dressing room and tried it on. OMG it fit and I really...
    shadowplt shadowplt 46-50, M 4 Responses 3 days ago

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    My wife has now left

    and I'm home alone. Finally I can shed these pants and put on a skirt. I was able to put on panties and a slip earlier, so it was easy to shed the trousers and don a skirt. Now I'm. comfortable.
    sharonwoods sharonwoods 51-55, M 3 Responses 4 days ago

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    My daughter had a great swim day.

    Too bad I missed it. I love watching her swim.
    shadowplt shadowplt 46-50, M 1 Response Nov 16

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    Today my wife and daughter are traveling to

    "the city" for a two day swim meet. I'm following a bit later. It'll give me a chance to dress and have some fun. I'm going to post a picture of myself in a little while. I'm hoping my daughter does well. I'm her biggest fan.
    shadowplt shadowplt 46-50, M 1 Response Nov 15

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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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    I can't tell you all enough how important the

    support I've received from everyone is to me. It's been nice to know there are others out there that have experiences like mine. I thank you all.
    shadowplt shadowplt 46-50, M 2 Responses 5 days ago

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    Today has been a wonderful day.

    I did dress underneath my male garments until I got home. Then I went back to boots in heels,skirt and shirt. My wife is accommodating my desires but still doesn't necessarily agree.
    shadowplt shadowplt 46-50, M 2 Responses 6 days ago

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    Dannjazz Dannjazz 22-25, M 6 Responses Nov 16

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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 dressed and watching a movie while she and my daughter were out. She came home and I had gone to bed. I had gone to bed dressed. She didn't...
    shadowplt shadowplt 46-50, M 3 Responses a week ago

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    I like to wear mini skirts,

    they are really cute. I am a huge girly girl sometimes.
    beautylasts beautylasts 13-15, F 4 Responses 2 days ago

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