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I Like to Wear Skirts

Personal Stories, Advice, and Support 2,285 People

    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 Nov 24

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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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    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 Nov 20

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    Well today I only had to work a half day.

    I wasn't scheduled for an afternoon simulator, so....I went home and changed into my boots and skirt. Sat on the couch and watched some of my favorite TV shows. It's nice to be dressed in a skirt and enjoy a day of nothing but mind numbing TV.
    shadowplt shadowplt 46-50, M 3 Responses Dec 3

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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 5 Responses Nov 22

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    Tonight my wife and daughter went to Wally

    World to shop. I've changed back into my fem clothes while they're out. I'll change back before they get home. Really enjoying the skirt and heels.
    shadowplt shadowplt 46-50, M 1 Response 3 days ago

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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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    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 24 Responses Jul 30

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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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    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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    Going to try more fem attire.

    As I age I've discovered that I really don't care too much what other thing of my appearance. I care what my wife and kids think, but the rest, I don't care. I want to enjoy how I feel and think.
    shadowplt shadowplt 46-50, M 20 hrs ago

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    This has been a skirt less weekend.

    😢 Yesterday I attended my daughters USA swim meet. Wow what a girl. Set several PR's. Very proud of her. Of course I couldn't dress for this so I just wore panties and my boots. I love my wife and daughter. She's (my daughter) a great swimmer.
    shadowplt shadowplt 46-50, M 1 Response Dec 7

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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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    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 6 Responses Nov 19

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    Dannjazz Dannjazz 22-25, M 6 Responses Nov 16

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    Good nite to my friends.

    I just want to once again say thanks.
    shadowplt shadowplt 46-50, M Nov 19

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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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    Tomorrow I'm driving to another city in the

    afternoon. I'm planning on wearing my favorite skirt and boot heels all afternoon and throughout dinner. I'm only taking male clothes for the swim meet I'm officiating at: don't think YMCA would appreciate a female dressed male as an official. Besides I don't want those I know...
    shadowplt shadowplt 46-50, M 1 Response Dec 11

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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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    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 now, my In-laws were here

    for the past two days. Had to dress manly while they are here. In the morning they and my wife and I get up early. I forgot that I'd painted my nails and walked into the kitchen with bare feet. Whoops. I don't think anyone but my wife noticed. Had to cover the nails. I like them...
    shadowplt shadowplt 46-50, M 8 Responses Nov 28

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    Girls, tonight I'd like to say thanks to the

    responses I've received on this site. Could some explain to me how to put on eye liner and still look like a man. I've gotten the mascara down, but have trouble with dressing the eyes.
    shadowplt shadowplt 46-50, M 2 Responses Nov 29

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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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    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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    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 Nov 21

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    pinkleatherpants pinkleatherpants 22-25, F 7 Responses May 20

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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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    I like to wet my panties

    while wearing a mini skirt
    mischef mischef 41-45, T 1 Response Nov 24

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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 Nov 21

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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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    starfire007 starfire007 13-15, F 14 Responses Jul 26

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    shadowplt shadowplt 46-50, M 3 Responses Dec 9

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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 3 Responses Jul 15

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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 Nov 19

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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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    I need help. I'm about to go to bed totally

    confused. I want my womanhood but also want male hood.
    shadowplt shadowplt 46-50, M 2 Responses Nov 24

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    The next two days ought to be interesting.

    I'm working Thursday and Friday,my wife and daughter are leaving for a swim meet. I'll catch up to them.
    shadowplt shadowplt 46-50, M 4 Responses 3 days ago

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    I got this skirt today

    while in the city. I really like the colors and the flare at the bottom.
    shadowplt shadowplt 46-50, M 4 Responses 22 hrs ago

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    I really enjoyed my afternoon today.

    I got off work early and went home. I was able to wear my fav skirt and boots for several hours. Washed my used panties and stockings and basically re-set my fem side. Tonight I'm going to enjoy an evening with my wife and re-set my masculine side. Love being fem and male.
    shadowplt shadowplt 46-50, M 3 Responses 3 days ago

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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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    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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    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 3 Responses Aug 6, 2012

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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 1 Response Nov 22

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    I hope I die in a fire from my life experiences

    I mean like Jesus my childhood and life is and was terrible, absolutely horrifying and just plain out terrible. I am just making this statement clear.
    Butterking47 Butterking47 18-21 3 Responses Dec 9

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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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    I can't express how proud I am of my daughter

    today. She's swimming so well.
    shadowplt shadowplt 46-50, M 19 hrs ago

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    Just wondering....why is the icon

    for this experience a dog in a skirt?
    shadowplt shadowplt 46-50, M 2 Responses Nov 25

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    To those of you who celebrate: Happy

    Thanksgiving 👗+💅*♥️=😍
    shadowplt shadowplt 46-50, M 4 Responses Nov 27

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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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    I love wearing skirts in the summer - a cute

    skirt about knee length, a knit top, and sandals: my summer uniform!
    BBWand40 BBWand40 41-45, F 6 Responses Mar 2

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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 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