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I Like to Wear Skirts

Personal Stories, Advice, and Support 2,669 People

    Having a great second day home alone.

    Got up, showered and shaved as I do every day. Then slipped on the blue skirt in my avatar picture and drove to the city for some shopping. My 16th anniversary is next Friday and I want to find something special for my bride. Didn't find what I'm looking to get her. I did get...
    shadowplt shadowplt 51-55, M 1 Response May 31

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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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    Today I went into the city looking

    for an anniversary gift for my wife. I was also looking for a denim skirt with pockets. Failed in both. After dinner I found my skirt here in town.
    shadowplt shadowplt 51-55, M 1 Response May 31

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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 3 Responses Jun 13

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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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    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 26 Responses Dec 27, 2011

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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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    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 61-65 2 Responses Aug 6, 2012

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

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

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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 6 days ago

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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...
    Prettyjennifer2004 Prettyjennifer2004 51-55, M 20 Responses May 21

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    Yesterday was a nice change of pace

    for me. I had to stay home to care for a sick family member. Got to watch too much TV. When the evening came, I was finally able to get some time to myself. I drove to the local walking path, changed into my skirt and heels, then went for a one hour walk. I met some friendly...
    shadowplt shadowplt 51-55, M 2 Responses May 12

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    Well yesterday was the first day I'm home alone.

    I was able to wear a skirt all day. What a wonderful feeling. I even went to see San Andreas without incident. (BTW...it's a typical disaster movie ). I just enjoy the freedom a skirt gives when it comes to movement and comfort. The colors and flexibility of mix and match is so...
    shadowplt shadowplt 51-55, M 3 Responses May 31

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    Tomorrow my wife and daughter leave

    for a vacation for a few days. I'm staying home 'cause I have to work next week. They're going to have a mother/daughter trip. Great for them! As a side benefit, I get to wear skirts, shirts and shoes when and where I want. I plan on being dressed as much as I can while doing...
    shadowplt shadowplt 51-55, M 5 Responses May 29

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    I like to wear mini skirts,

    they are really cute. I am a huge girly girl sometimes.
    deleted deleted 26-30 5 Responses Nov 21, 2014

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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.
    Prettyjennifer2004 Prettyjennifer2004 51-55, M 18 Responses Jun 3

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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 27 Responses Jul 30, 2014

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    Wow. I just experienced a realization.

    I need to just exude some confidence in myself to feel feminine and comfortable with myself. I've worn skirts, boots and heels in public and have never had a negative comment. I've just been scared about how others perceive me. Who cares what a stranger thinks. I won't see or...
    shadowplt shadowplt 51-55, M 3 Responses Feb 5

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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 1 Response Jun 1

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    So here's my weekend: Friday afternoon my wife

    and daughter drove to the city to spend the night before her swimmeet. I had the house to myself and wore my skirt and heels. yummy night. Saturday I had to be up at 5am, shower and drive to the city for the meet. Drove dressed, never had any problems. Stopped at several...
    shadowplt shadowplt 51-55, M 1 Response Mar 15

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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 36-40, F 1 Response Apr 24, 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 61-65 7 Responses Jan 9

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    Tonight I did my usual 2 mile walk.

    I was wearing my skirt and heels. The breeze was enticing on my legs as my skirt swirled around my ankles and heels. What a fun walk.
    shadowplt shadowplt 51-55, M 2 Responses Apr 26

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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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    A couple months ago i mentioned to my wife

    that I was curious about expanding my pantyhose wearing to skirts and shoes. She didnt seem to keen on the idea but said ok. A couple Saturdays later i woke up around 5 am. Knowing I had a few hrs before the rest of the family woke up. I grabbed a pair of my suntan stw pantyhose...
    deleted deleted 26-30 4 Responses May 21

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    I love wearing either a short skirt

    and blouse or short dress, hose, and high heels. My skirts and dresses are measured 3 to 4 inches above my knees.
    oldersinglemom oldersinglemom 41-45, F 12 Responses Jun 5

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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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    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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    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...
    Prettyjennifer2004 Prettyjennifer2004 51-55, M 5 Responses Jul 19, 2014

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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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    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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    I'm thinking that tonight,

    after dinner I'm going out for another walk. I'm feeling rather fem in my mindset and just wanting to wear my skirt. Tomorrow I have to take my truck to get fixed and will be home alone. SKIRT time :-)!
    shadowplt shadowplt 51-55, M 1 Response May 20

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    I went to the city today looking

    for a denim skirt with pockets. I'm tired of having to wear skirts and then hand carry my wallet and phone. I went in my red skirt and heeled boots. I'd forced myself to not chicken out in public by leaving my pants at home. The mall was fun. Every store I went into, I had...
    shadowplt shadowplt 51-55, M 7 Responses May 16

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    I like skits because I feel

    that skits come in all different colors and designs.
    elrod2006 elrod2006 22-25, F 1 Response May 29

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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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    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 5 Responses Jun 14

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    Funny thing. Tonight I was browsing on Google

    and put in "males in skirts", most notably the guys were models. Hummmm .... I can't compete. They also look queer; unsure how to feel relaxed.
    shadowplt shadowplt 51-55, M 1 Response May 22

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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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    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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    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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