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I Like to Wear Skirts

Personal Stories, Advice, and Support 2,106 People

    1234Ideclareathumbwar 1234Ideclareathumbwar 18-21, F 2 Responses Apr 13

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    Just a fun little picture.

    I'll add some different ones in a bit.
    shadowplt shadowplt 46-50, M 1 Response Jun 9

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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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    shadowplt shadowplt 46-50, M 2 Responses Jun 1

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    undrayaaa undrayaaa 18-21, F Jun 8

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    shadowplt shadowplt 46-50, M 2 Responses Jun 1

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    shadowplt shadowplt 46-50, M 1 Response Jun 9

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    pinkleatherpants pinkleatherpants 22-25, F 7 Responses May 20

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    I Love Shopping!

    Yesterday my wife and I went shopping at our local KMart. I like Jacklyn Smth fashions, maybe 'cause I watched her on Charlies Angel and liked her clothes then. Anyhow, we found huge mark downs on everything! Tops, suits and SKIRTS!!! At $5.00 each I could have easily blown our...
    leggsqueen leggsqueen 56-60 4 Responses Mar 4, 2012

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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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    Ok, I realize most of those

    who post here are guys. We do our best to emulate those we love but NOTHING we do or wear will make us as pretty as the women we love. Watched my daughter get ready for a band camp. She and Mom were getting her concert dress ready and modeling it, wow one proud Dad! We guys...
    shadowplt shadowplt 46-50, M 5 Responses Jul 5

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    Wondering something..

    ...I know about wearing skirts What do straight married guys do? When they want to crossdress?
    shadowplt shadowplt 46-50, M 4 Responses Jun 2

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    Han an evening on the pool.

    Relaxing and getting rained upon! We really needed a good soaking.
    shadowplt shadowplt 46-50, M Jun 2

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    I've had a unique experience

    for myself. I've brought my hi heeled boots to work yesterday and today. Put them on (under my male slacks), they look no different than the boots I normally wear, and no one noticed! It's weird because I work in an ULTRA conservative environment. I actually had a guy ask me...
    shadowplt shadowplt 46-50, M 1 Response Jul 10

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    shadowplt shadowplt 46-50, M 1 Response Apr 20

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    Tonight once again floating on my pool

    and doing the EP thing. Over 100 deg today ... Ouch. Wore my black skirt to work and a nice soft pair of panties. Of course I can't openly wear them (sad). Did get to wear my boots and nylons underneath. (Happy).
    shadowplt shadowplt 46-50, M 3 Responses Jul 9

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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 2 days ago

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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 8 Responses Apr 1

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    Question: My wife knows about my skirt wearing

    and probably my wear of heel boots. She's told me that I had to let my arm hair grow out ( I tried shaving them for a few weeks) but haven't said much else. How do I present myself to her ? She's VEry conservative .
    shadowplt shadowplt 46-50, M 2 Responses Jun 21

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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 2 Responses 10 hrs ago

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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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    I get to do as I want tonight.

    My wife and little girl are at a swim meet, which I'll meet them tomorrow. So tonight I get to wear my skirt and boots. Yea! Will wear them driving to the meet tomorrow.
    shadowplt shadowplt 46-50, M 2 Responses Jun 27

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    I know I hear this all the time,

    guys who CD and say that they're straight. My opinion on this statement is that while we love our ladies, we have to be somewhere on the TG spectrum. I think most of us enjoy the ladies clothes and feeling fem, but at the same time we're males, and have male desires. This places...
    shadowplt shadowplt 46-50, M 7 Responses Apr 27

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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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    Tonight I get the house to my self.

    My wife is off to another city, my son is at work and my daughter is at a swim camp. Kinda weird to be home alone. It does allow me to dress as I please. So, tonight I get to wear my skirt, heels and fem stuff. I've tried some makeup for the eyes. Not too bad. Looks...
    shadowplt shadowplt 46-50, M 2 Responses Jun 13

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    Tonight has been a weird night.

    Wore my skirt on my float then got rained upon. Yea rain! Really it's been so dry here. Wanting to wear my girl stuff, but can't. Guess I'll just have to wait till tomorrow.
    shadowplt shadowplt 46-50, M 1 Response Jun 2

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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 2 Responses 4 days ago

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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...
    jmallon764 jmallon764 18-21, M 3 Responses 1 day ago

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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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    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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    So today I was wearing my boots out

    and about running errands after work. I got a weird look from some ladies older than I am. One walked over to me and asked,"Young man, why do you have ladies boots on"? My reply to her was that they're comfortable and I liked the look. Then I asked her, "And why do you have on...
    shadowplt shadowplt 46-50, M 1 Response Feb 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 3 days ago

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    Floating on the pool last night with my cell

    phone. You guessed it, plop. Dang, had to revert to an older model. Won't do that again.
    shadowplt shadowplt 46-50, M 1 Response Jun 1

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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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    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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    You asked. I deliver.

    My fav skirt in the pool
    shadowplt shadowplt 46-50, M 2 Responses Jun 3

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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 7 Responses Mar 24

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    Tonight I once again tried an anal insert.

    The tampons with plastic surrounding them fit well and really make you feel as though you need to poop. Add pool water and they expand inside you. It's and amazing feeling. I felt every aspect of it as I sat on the pool float.
    shadowplt shadowplt 46-50, M 2 Responses Jun 4

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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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    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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    This evening my bride of 15 years is at my

    daughter's apartment passing on the skills of making enchiladas. I get to stay home and get some skirt/ boot time. Looking forward to an evening alone with my wife. Probably won't be dressed, but fun none the less. Also looking forward to an enchilada dinner.
    shadowplt shadowplt 46-50, M 2 Responses Jul 8

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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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    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 3 Responses 6 days ago

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    Kind of proud of myself toady.

    Wore my low rise short boots to the bowling alley on base. I had on thigh high hose ( boots are more comfortable with nylons than cotton socks ) and a skirt under my jeans. A couple lanes away a group of girls and their moms were bowling. As I changed into my bowling shoes one...
    shadowplt shadowplt 46-50, M Jun 8

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    Tonight......doing what I love.

    ...grilling in heels. Hamburgers, hot dogs, beans and bullets. Nothing better than the American burger by a pool and on a grill!!!!!!
    shadowplt shadowplt 46-50, M 2 Responses Jul 1

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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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    Today was a first for me.

    I went out wearing a skirt and heeled boots. Kinda scared me. It was a knee length black bell shaped skirt with black 3" heeled boots. Didn't spend much time outside my truck. Just enough to towel dry it after washing. Felt scared and exposed, yet at the same time exhilarated...
    shadowplt shadowplt 46-50, M 3 Responses Feb 14

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    Today I was able to get off work early

    and wear my skirt and boots. I wore the skirt in my truck and hid it when running errands. Still skittish about being open with a skirt. Boots are a different story. Getting comfortable with wearing them around town. Get some weird looks occasionally, but no comments or glares...
    shadowplt shadowplt 46-50, M 3 Responses Mar 26

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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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    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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    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 1 day ago

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    Related Experiences

    I have just discovered this maker of skirts for men http://www.skirtcraft.com Check it out!
    Prettyjennifer2004 Prettyjennifer2004 51-55, M Jul 15

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