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I Like to Wear Skirts

Personal Stories, Advice, and Support 2,733 People

    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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    What a weird day. I'd planned to drive to the

    city to do some shopping while in my skirt and heeled boots. After breakfast and some house stuff, I took off. I'd changed into my skirt and heels and started to the city. I did stop at a convene store for a soda and a pee. The clerk was surprised I used the men's room. After I...
    shadowplt shadowplt 51-55, M 1 Response May 9

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    I went on a road trip from SD to Memphis

    wearing a skirt and heels had no problem what a great time
    jerbare jerbare 61-65, M 5 Responses Apr 30

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    Went and saw Rodney Carrington last night.

    What a funny guy. WOULD NOT take a young child (under 18) to see him perform. Very fun show. My wife and I laughed our A&& off.
    shadowplt shadowplt 51-55, M Jun 14

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    Yesterday I went for my customary evening walk.

    I wore my ankle length red/black skirt, heeled boots and a tee shirt. Had a fun walk. Passed a bunch of people with no comments (yea). On the way home, I stopped at a convenance store to get a soda. While filling my cup, the clerk (a woman) came up to me and complemented my...
    shadowplt shadowplt 51-55, M 2 Responses Jun 17

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    I see my style and sexy sophisticated,

    and I love a good above the knee form fitting pencil skirt.
    CDrixieXXY CDrixieXXY 31-35, T 9 Responses Feb 17

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    Today I put on my Wolford 20 sheer hose

    and a black denim skirt with flats. My wife wanted to visit her friends house but wanted me to drive her there so I had to take her there and back about 30 minutes each way. I decided not to change into male clothes but stay in my tights and skirt. She didn't say anything about...
    deleted deleted 26-30 21 Responses May 21

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    Just arrived at my layover destination.

    So far so good. I been given a few "looks", but otherwise it's been a wonderful experience traveling while skirted. It's much more comfortable and cooler (temperature wise) than jeans.
    shadowplt shadowplt 51-55, M 2 Responses Jul 6

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    This evening my two sisters

    and their husbands will see me wearing a skirt. They do not know I wear skirts. Wish me luck.
    deleted deleted 26-30 18 Responses Jun 3

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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 15 Responses Oct 1, 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...
    deleted deleted 26-30 5 Responses Jul 19, 2014

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    It's not an issue for me,

    though. I'm a woman. But I still love wearing skirts. I love wearing those dyed gauze skirts with a halter top or a cropped baby tee, & bare feet!
    MeghanL MeghanL 26-30, F 7 Responses Jun 3

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    just tonight I worked up the courage to step

    out in a skirt and wedges and walk around the block it was a little scary and got the heart rate going but nothing bad happened was seen by a few passing cars it was a fun time
    jamie172 jamie172 46-50, T 6 Responses 4 days ago

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    I have the best family ever I'm a 45 year old

    man married to my wife and I have 3 kids two girls aged 22 18 and one boy aged 15 and they all know that I wear skirts and tights nothing else I don't want to be a woman I am just a man who likes to wear them , they really support me in doing this and I love them for it , I...
    deleted deleted 26-30 13 Responses Jul 13

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    I'm beginning to realize

    that I'm going through some life changing experiences. I'm not sure if they are positive or negative. I've been slowly working my way into more feminine attire, looks and mannerisms. It's nothing I've consciencely been doing, I've just noticed that I find myself desiring more...
    shadowplt shadowplt 51-55, M 7 Responses May 8

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    The skirt and top I had on

    when I drove into work this morning.
    mat2Robin43 mat2Robin43 51-55, M 9 Responses 3 days ago

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    Not quite sure where to put this post,

    but I think this will do just fine. Saturday I painted my toe nails a nice light purple sparkle color. Just having some fun and didn't think about it. Today I had a Dr's appointment for a full body scan of my skin. (I've had melanoma and some other skin cancers. ) Well I'd...
    shadowplt shadowplt 51-55, M 2 Responses Apr 13

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    This is the skirt I wore today.

    I'll be sad to take it off at the end of the day.
    KatieTreat KatieTreat 51-55, T 30 Responses Jun 30

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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 5 Responses Jan 22

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    What a wonderful day it is here in Ok.

    Sunny, warm and most importantly, NOT windy. A perfect day to wear a skirt and heels while car shopping. I drove to OKC to price some cars for my daughter. Her's was totaled by the insurance company and was paid for better than blue book to replace it. I decided to wear my...
    shadowplt shadowplt 51-55, M 7 Responses Apr 25

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    Getting ready to go to a swim meet this

    afternoon. Feeling very fun and confident about the drive and watching swimming. Plan to wear my blue skirt (see my avatar) and heels. Hope my wife approves.
    shadowplt shadowplt 51-55, M 7 Responses Jun 27

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    After taking care of home stuff,

    yard work, cleaning the house, washing clothes etc. I'm going to the city and shopping. I plan to skirt it up and look for some heels. I've a new goal, finding a swim suit....one piece.
    shadowplt shadowplt 51-55, M 6 Responses Jun 14

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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 61-65 8 Responses Jan 9

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    wearing one of my nice jean skirts is always

    fun I feel cute and with fresh shaved legs even better. I enjoy the sensation of any skirt sliding on my skin.
    whitwhit86 whitwhit86 26-30, M 5 Responses a week ago

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    starfire007 starfire007 13-15, F 11 Responses Jul 26, 2014

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    This is the first of my return home experiences.

    As I type this I'm sitting in my plane seat at 39,000 ft in my blue skirt and heeled boots. It the one on my avatar. So, far so good. Drove to the airport stopping along the way to fill my rental car and get a soda. No one batted an eyelash. Yea! Once at the airport, went to...
    shadowplt shadowplt 51-55, M 6 Responses Jul 9

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    On my way to my parents house in another state.

    I'm sitting in my hotel room 'cause I've an early wake up tomorrow. I wore this skirt and heels to the city, dinner and shopping. Felt wonderful to have a few shop clerks complement me. Went into a convince store for a soda. When I came out, two young ladies had their phone...
    shadowplt shadowplt 51-55, M 6 Responses Jul 5

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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 7 Responses Jan 9

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    pinkleatherpants pinkleatherpants 22-25, F 6 Responses May 20, 2014

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    I found a new skirt today at the thrift store.

    It's my second one. I can't wait to wear it.
    hissassy1 hissassy1 41-45, F 1 Response Jun 30

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    I just got a text from my friend reminding me

    that I committed to a golf tournament tomorrow. He's a burly, barrel-chested, manly - man with a heart of pure gold and knows nothing about my feminine wiles, as far as I know. So my wife and I meet he and his wife for a night out, and he shows up wearing a kilt ! When I...
    JessicaDale JessicaDale 51-55 7 Responses May 8

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    Wow. Had a very (to say the least) frank

    discussion last night with my wife. She's not comfortable with the idea of me dressing and wearing women's clothes. She's afraid I'll go Bruce on her, which is the farthest thing on my mind. I love her so much and hate that this is something that's getting in our way. I wish I...
    shadowplt shadowplt 51-55, M 11 Responses Jun 24

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    Yesterday was a fun day.

    My wife, daughter and her friend went to an aquarium a few hours away. That left me at home alone. We're painting my daughter's new room, so I took up a roller and worked on it as much as I could. When finished, I dressed and drove to the city to go to a mall and shop. What a...
    shadowplt shadowplt 51-55, M 4 Responses Mar 22

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    I bought a box of 50 hangers off ebay several

    months ago, for hanging leggins and skirts in my closet, thinking it would be a very long time before I ever used that many. Now I have a shortage of hangers. I think I have enough skirts for now. But I saw one at JC Penny today that I really want. *sigh* I think I have an...
    KatieTreat KatieTreat 51-55, T 5 Responses Jul 4

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    The Lord was with me yesterday.

    Being over 50, it was time to get scoped. My wife drove me to the hospital and very patiently sat with me as I waited my turn for the doctor to perform his magic. Her patience and love removed all doubts about the procedure. Everything turned out well and I finally got to have...
    shadowplt shadowplt 51-55, M 4 Responses Jun 13

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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 26 Responses Jul 30, 2014

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    Monday I fly to Washington,

    D.C. I plan to wear my red skirt and heels the whole way. I'm driving to my parents house to be with my Mom as she's going through cancer treatment. I plan to expose myself to her before she passes. I want her to know. I'll return dressed until I get home. I need to do the...
    shadowplt shadowplt 51-55, M 11 Responses Jul 4

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    Once again, attempting to add a picture of my

    latest addition. Just updated the app, we'll see. It a denim skirt with pockets!
    shadowplt shadowplt 51-55, M 4 Responses Jun 14

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    Tomorrow, I get on a plane to fly home

    after visiting my mother in my home town. She's getting up there in the years and finds my transgender experience interesting, though may never think of me as anything other than her son. However, this experience has helped us make a connection that we've never had before. I...
    KatieTreat KatieTreat 51-55, T 7 Responses 4 days ago

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    Yippee! Another evening walking in my local

    town in my skirt. Very happy. Very confident.
    deleted deleted 26-30 Jul 21, 2014

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    How's this for a girly rental car?

    No muscle, no frills.
    shadowplt shadowplt 51-55, M 5 Responses Jul 7

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    My new skirt. Kind of feels restrictive to walk

    in. I've never had an A frame skirt.
    shadowplt shadowplt 51-55, M Jun 1

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    What's with trying to attach a photo.

    I've done it before and now all I get is an Apple dialog saying "Ok"? Anyone know what's up?
    shadowplt shadowplt 51-55, M Jun 1

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    Tonight I went out to our local walking trail

    wearing my favorite skirt. Right now I'm home, floating on my pool and enjoying a cooling breeze. I have a Cool male swimsuit on and have painted my toe nails a very bright red. Love being a woman and a guy.
    shadowplt shadowplt 51-55, M 5 Responses Jul 21

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    This is the last of travel blog (if you want to

    call it that). I've finally arrived at my destination. My parent's house. As you may or may not know, I traveled wearing a red ankle length skirt (similar to my blue one I posted yesterday), high heeled boots and knee length nylons. My shirt was a simple red, v-necked tee...
    shadowplt shadowplt 51-55, M 5 Responses Jul 6

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    Well, I'm convinced the world (at least around

    where I live) isn't as asinine as the TV and news would have you believe. I went to the city today dressed in a skirt and heeled boots. As I've said before, no make up, breast forms or pretending to be what I'm not. I was accepted in every place I went; the mall, conscience...
    shadowplt shadowplt 51-55, M 1 Response Jun 21

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