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I Like to Wear Skirts

Personal Stories, Advice, and Support 2,162 People

    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 9 Responses Mar 24

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    pinkleatherpants pinkleatherpants 22-25, F 7 Responses May 20

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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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    Today is 9/11. I realize

    for many of you it's a so what day. To me VERY Solomon. America was attacked by radicals. We've fought back. I cried on this day. I fought in the Gulf wars. I defended my country. What a day.
    shadowplt shadowplt 46-50, M 1 Response Sep 11

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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 4 Responses Jul 23

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    I just thought of it.

    I wear my chef pants daily, why not get a waiter apron to wear daily every where? It's like a skirt somewhat an I can still wear shorts with a square apron! Or just a skirt too lol! Clever I am!!
    TransAsian TransAsian 26-30, T 1 Response Aug 29

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    Just wondering, if I've good shaved legs

    and 27 male, an it's 2014, should I show off my shaven legs in public or no in a skirt? I shaven my entire body. I love the feel of nicely shaven every where!! Thoughts, comments, suggestions wanted!! I currently in Providence, RI for college.
    TransAsian TransAsian 26-30, T 4 Responses Aug 2

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    Today my wife got up early,

    4:30, so did i. Deem wanting to go to bed early tonight. Wore my skirt to work. Boots too. Had fun and taught a lot.
    shadowplt shadowplt 46-50, M Aug 29

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    My wife and daughter went to the city today to

    watch a movie. Had the house to myself. Mowed the yard and cleaned the house in my fav skirt and heels. Nice day.
    shadowplt shadowplt 46-50, M 3 Responses Aug 16

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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 21 Responses Jul 30

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    Tomorrow I have to drive another two hours back

    to the city. This time to see an eye doctor. I had surgery on my right eye socket last February and I have to follow up with a specialist. I'm planning on wearing a red tartan skirt and a black v next tee; along with 3" heeled boots and nylons. Looking forward to the drive...
    shadowplt shadowplt 46-50, M 3 Responses Aug 10

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    My wife, daughter and I accepted

    and did the ALS challenge. We're donating $30 to the cause. I challenge three of my circle to do the same. I did mine dressed in my favorite skirt and tee shirt. How will you do it?
    shadowplt shadowplt 46-50, M 1 Response Aug 22

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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 4 Responses Jun 14, 2012

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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 4 Responses Apr 24

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    Tonight was the first night of our bowling

    league. I wore a skirt and heels to the game. Skirt was under pants heels exposed. Han a great time.
    shadowplt shadowplt 46-50, M 1 Response Sep 11

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    So Versatile

    I find dresses and skirts so feminine. I could wear both for almost any function. Skirts are especially good for work as they not only look professional but you can show off some very special blouses and tops. Skirts come in many shapes and sizes. Although I'd love to wear...
    Josie06 Josie06 56-60, F 7 Responses Sep 30, 2008

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    shadowplt shadowplt 46-50, M 2 Responses 6 days ago

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    Going thru TSA security line later today.

    I'll have to take off boots and go thru the exam line. I wonder if they'll pull me aside wearing panties and other female attire. Guess I won't risk it and dress for my gender.
    shadowplt shadowplt 46-50, M 2 Responses May 23

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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

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    Hello,my name is jacob

    but i like to go by zoey. I have spent the last seventeen years of my life alone because I am a girly-boy. Now I have the Internet and sites like this. i am now seeking help from someone who lives near me. i live in Virginia and am looking for some one I can meet, i love EP...
    zoey764 zoey764 18-21, T 2 Responses Jul 23

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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 5 Responses Apr 12

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    I did it today! I wore my skirt in public in

    heeled boots! :-) It wasn't for long. I've done this before in the dark, but not on purpose. Today was a conscience decision. I washed my truck and had to dry it. The wind was blowing Oklahoma fast, so I just figured what the heck. Oh what a feeling! Skirt billowing, heels...
    shadowplt shadowplt 46-50, M Aug 31

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    Learning something new each day.

    Today I started to figure out that John Q Public ( most of them anyway) really couldn't give a rats A_ _. What you wear when out and about. Some will Lear, make funny faces or chuckle to their friends, but most just don't notice or care. They're too busy with themselves and...
    shadowplt shadowplt 46-50, M 3 Responses Mar 14

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    While I like the feel

    and comfort of wearing a skirt, I like watching American football even more. I may be a guy in women's clothing, but I'm still a football guy Tomorrow, high school football. In nirvana!
    shadowplt shadowplt 46-50, M 3 Responses Sep 4

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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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    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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    Wow this morning I tried hoes with garter

    straps on thigh high hose. Very interesting feeling on the legs. Not quite sure if I like them over knee length hose. I'll give it a day and see.
    shadowplt shadowplt 46-50, M 1 Response Apr 23

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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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    What a wonderful day.

    My wife was out of town all day. My son worked and I had the house to myself....besides the dog and cat. Got to wear my skirts and heels all day. Worst part was when the cable went out. Decided to go bowling, power was out to the alley. :-( Came back and went for a swim in my...
    shadowplt shadowplt 46-50, M 1 Response Jul 13

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    Getting ready for work.

    Skirt and boots with short hose.
    shadowplt shadowplt 46-50, M 2 Responses Aug 25

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    Well the wife and kids are away

    and I have the place to myself. Time for skirts, boots and a movie!
    shadowplt shadowplt 46-50, M 3 Responses Jul 24

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    Tonight I'm wearing a skirt to bed.

    Wonder what My wife well feel.
    shadowplt shadowplt 46-50, M Aug 24

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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 4 Responses Jul 19

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    Today after a VERY early wake-up,

    (set my alarm to get up early yesterday) my dog heard it and woke me to go pee. Anyway, my wife cooked some great French Toast we did our morning stuff. I dressed in my skirt and jeans. Wore them all day. :-) went bowling wearing them. My wife went shopping with my...
    shadowplt shadowplt 46-50, M Aug 2

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    Skirts And Dress Are The Bomb

    I too preferre skirts over pants or slacks, next to a pair of cleanly waxed legs, there is no comparison when the soft lining of the skirt rubs against your bare or pantyhosed legs. It definately shows of a cute blouse as well. But dresses are an easy solution to something to...
    MaryAnn4665 MaryAnn4665 46-50, M 2 Responses Oct 17, 2011

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    Tonight I'm floating on my pool

    and enjoying a cool breeze. I'm wearing my fav pool skirt and writing this blog. Tomorrow I have an early wake up. I'm having cancer surgery again. I've been having bouts of Melanoma for the past 8 years. Everything is going ok, but I'm tired of the surgeries. Just want it...
    shadowplt shadowplt 46-50, M 2 Responses Jul 31

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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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    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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    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 3 Responses Aug 12

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    starfire007 starfire007 13-15, F 13 Responses Jul 26

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    My wife was miffed at me today.

    I thought it was because I was wearing a skirt last night. Turns out she had a beef with how I was discussing living arrangements with my 23 yr old son. She actually complemented me on my appearance. Then the ax fell on other stuff. One confused guy. Some nights skirts aren...
    shadowplt shadowplt 46-50, M Jul 28

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    Went thru cancer surgery today.

    I have bouts with melanoma. All's well and feeling fine. Just a new scar on my face. Guess that removes me from those who can pass.
    shadowplt shadowplt 46-50, M 1 Response Aug 1

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    As I said in my last post,

    I was going to wear a skirt to my daughter's swim meet; I did. Great drive to the venue and once there, no one questioned it! Did have a few younger kids giggle and a couple of people give me weird looks....(perv or something...not quite sure) Best thing to wear in a humid...
    shadowplt shadowplt 46-50, M 2 Responses Jun 28

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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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    I had a unique experience at a convince store

    just this afternoon. I was filling a soda when a rather large man came to get a soda. He looked at my boots (I was wearing 3" heels) under my work pants and said, "Those are awesome boots. Where did you get them?" I was flabbergasted that a guy would complement my heels. I don't...
    shadowplt shadowplt 46-50, M 4 Responses Jul 15

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    I love wearing skirts in the summer - a cute

    skirt about knee length, a knit top, and sandals: my summer uniform!
    BBWand40 BBWand40 36-40, F 6 Responses Mar 2

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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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    Yesterday I took a two hour drive to a swim

    meet in a nearby city. I worked as an official. I drove there wearing my skirt, heels and uniform shirt. Once at the pool I ditched the heels and put on water shoes ( the pool deck gets really wet ). I worked six hours in a blue cargo skirt, white polo shirt and deck shoes. No...
    shadowplt shadowplt 46-50, M 1 Response Aug 10

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    I Love My Skirts

    From maxi's, to mini's, to denim, to high wasted, to colorful I have all the skirts you can imagine! My favorite are the high wasted skirts. I have 4 high wasted, 6 mini's, 3 denim, 5 maxi's, and 3 different colored denim (pink, ombré orange, and ombre green). Skirts make me...
    Fieldhockeylover Fieldhockeylover 18-21, F 2 Responses Jul 9, 2013

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    Related Experiences

    Apart from shorts, I have only been wearing dresses or skirts since I was 8 or something. And apart from the fact that my husband does not want to see me in trousers, I like...
    Susanna3 Susanna3 31-35, F 7 Responses Aug 21

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    I've always been more boyish and spent my teenage years dressing in baggy black clothing (I admit I still do that a lot of the time :-D), largely because I was conscious of my body...
    kakhi kakhi 18-21, F 2 Responses a week ago

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    Never liked wearing underwear...over the years going from the whitie tighties, to boxer briefs, to boxers....felt better without them. I haven't worn any in over a month now...
    codeblue665 codeblue665 36-40, M 1 Response Sep 5

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    I like wearing leotards! They are so sexy!
    ILoveSpandex ILoveSpandex 18-21, M 1 day ago

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