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I Like to Wear Skirts

Personal Stories, Advice, and Support 2,454 People

    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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    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, 2014

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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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    I think I'm going thru a period in my life

    where I'm not certain about who I am. I enjoy and love being a guy, but I also am enjoying my feminine self. It's causing a lot of hardship in my personal life and my marriage. My wife sees it quite differently than I do and it's causing us stress. I'm not sure where this is...
    shadowplt shadowplt 51-55, M 9 Responses Feb 19

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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 6 Responses Jan 22

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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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    Tonight I was supposed to drive to another city

    to watch my daughter swim in the regionals swim meet, dang a bug hits me and whamo, I'm stuck dog sitting and nursing a fever. This sucks. The only up side is I get the house to myself and can be a sick (not in a bad way) me. Early bedtime for me tonight.
    shadowplt shadowplt 51-55, M Feb 6

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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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    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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    Spent the afternoon in my skirt

    and heels. Did this after taking my daughter to a dr appointment. This evening I'm home alone for a while. Wearing my boots and skirt watching the evening news.
    shadowplt shadowplt 51-55, M 4 Responses Feb 2

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    shadowplt shadowplt 51-55, M 2 Responses Feb 14

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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'm begging to think

    that I'm weird. My wife definitely thinks my dressing is weird. So too do I. Not sure where to go. Please help
    shadowplt shadowplt 51-55, M 5 Responses Feb 11

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    My newest purchase for wear under skirts

    and jeans in cold days or just around the house.
    shadowplt shadowplt 51-55, M 1 Response Feb 15

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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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    Today I wore a skirt

    and went on my favorite walk. Felt nice. Skirt bellowing in the breeze. Wonderful feeling having the fabric rustle your shaved legs.
    shadowplt shadowplt 51-55, M 2 Responses Feb 10

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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, 2014

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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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    Don't quite know how to express my enjoyment

    today. I went into the city dressed from the waist down. Wore my heeled boots panties and mascara. Otherwise presented as male. Not a single negative comment or sneer. I felt so pretty and feminine. Loved my day. Shopped all day dressed and never a comment to me. I'm sure some...
    shadowplt shadowplt 51-55, M 1 Response Feb 8

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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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    Today I'm going back to watch my daughter swim

    in the State finals for High School swimming. I'm really wanting to wear a skirt to the pool. It just gets hot in jeans or shorts. I don't think my wife will agree to it though. So I'll sit there hot and uncomfortable.
    shadowplt shadowplt 51-55, M 9 Responses a week ago

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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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    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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    I'm tempted to wear a skirt to work.

    But I'm not brave enough, yet. Plus, I'm a minority among my cowrokers, most of whom are from India. Anybody have any clue what their general attitude is toward trans people in India?
    KatieTreat KatieTreat 51-55, T 4 Responses 5 days ago

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    One time while I was wearing my skirt

    and heels I tripped in front of a guy and he got to see right up my skirt. I was wearing pink panties to boot, so that made things more awkward.
    AnyaGirl AnyaGirl 22-25, F 2 Responses 5 days 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 5 Responses Nov 21, 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 25 Responses Dec 27, 2011

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    I'm going to the city this weekend to watch my

    speedy daughter swim against some of the best in the region. It's supposed to snow by Friday afternoon. I'm planning on bringing my short skirts (thigh length) to wear while watching the meet. I'm driving home Friday evening and will completely dress in my skirt and boots. My...
    shadowplt shadowplt 51-55, M 2 Responses 2 days ago

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    pinkleatherpants pinkleatherpants 22-25, F 7 Responses May 20, 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 1 Response Apr 24, 2014

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    I'm trying something new today.

    I recently purchased a pair of yoga pants, half stretchy leather and half lycra/cotton. Wearing them under my dress pants commando while at work. What a great and cool feeling. It's cold outside and they are very warm.
    shadowplt shadowplt 51-55, M 2 Responses 4 days ago

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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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    Woke up this morning (way to early)

    after sleeping 10-11 hours. What a great way to cleanse the body of a cold/infection. Going to drive to watch my daughter swim in the finals of her regional swim meet. Feeling like a new me. Plan to wear my skirt and heels while getting there. I'll post a picture on my journey...
    shadowplt shadowplt 51-55, M 5 Responses Feb 7

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

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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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    It was rather hot today

    and to be comfortable I wore one of short demin skirts, not that fashionable but comfy
    paula3198 paula3198 46-50, F 2 Responses Feb 7

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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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    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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    Wow, painting your nails is an exciting

    and exeleriating experience.
    shadowplt shadowplt 51-55, M 3 Responses 16 hrs ago

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    This evening..... While skirted up waiting

    for my family to get home from work, swimming and whatever else they're doing. Prepped for cooking dinner ( fajitas ). Curled on the couch and just had a wonderful fem afternoon. Hope you all enjoy yourselves too.
    shadowplt shadowplt 51-55, M Feb 16

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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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    Follow up to my experience in the city with my

    daughter's swimming. It's been a long day and more to follow tomorrow; lots of driving and sitting. BTW she did great. I was able to wear my fem clothes most of the afternoon and this evening. My wife is with my daughter at the hotel and I'm home dressed watching TV. Since my...
    shadowplt shadowplt 51-55, M 1 Response 18 hrs ago

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    Really want to get dresses

    for Valentine's Day. Won't but want too. If love to surprise my wife and be myself. She won't agree.
    shadowplt shadowplt 51-55, M 2 Responses Feb 13

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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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    I absolutely hate when EP members leave

    nonsensical posts. Especially in all caps. Block those types.
    shadowplt shadowplt 51-55, M 1 Response Feb 14

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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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    One of the special things I like about skirts

    and some women's attire, is the diversity of colors, styles and the mix and match possible. I'll NEVER pass as a woman and never want too, I just like the comfort, colors and the feeling of femininity the clothes provide. Sometimes it's hard to dress in public and sometimes it's...
    shadowplt shadowplt 51-55, M 2 Responses Feb 11

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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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    This is the face of my Valentine's Day card.

    Read my next post and you'll get it.
    shadowplt shadowplt 51-55, M 3 Responses Feb 14

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    This doesn't quite fit the skirt theme,

    but I found a pair of what I believe to be yoga pants the other day. Pleather in the front and Lycra in the a$$ and butt. Under a skirt they feel really cool. Ankle length and up over the butt they are so comfortable. I really want to wear them all day.
    shadowplt shadowplt 51-55, M 1 Response Feb 9

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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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