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I Love Wearing Skirts

Personal Stories, Advice, and Support 535 People

    Elegant And Graceful

    Long skirts that flow through the wind as you walk. When you twirl it spins with you. While you dance it moves to your rhythm like it has a dance of it's own. It shields you from prying eyes. They make a man have to imagine what you look like. The are elegant and very "lady like...
    Caitlinsmith1636 Caitlinsmith1636 18-21, F Feb 11, 2013

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    Many years ago when my ex

    and I split, she left clothes she had not worn in a long time. When I was packing her stuff to donate I found a skirt with a stretch waist that looked like it would fit me. I had always wondered what it felt like to wear a skirt with the free flow of air and all that, so I tried...
    Myotheridentity Myotheridentity 46-50 2 Responses Jun 23

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    No More Pants, I Wear Skirts Exclusively

          I have gotten rid of all of my pants.   I now own over 25 skirts, its all I wear anymore.  I can't really understand why more guys don't wear them. They are extremely comfortable.  They are substantially lighter then pants or...
    bobbie13 bobbie13 56-60, T 4 Responses Sep 5, 2010

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    Ok, I Know I've Already Said On Here That I'm A Jeans And T-shirt Kinda Girl, But....

    I love wearing skirts. Don't get me wrong, I love wearing a comfortable pair of pants and a regular shirt or blouse around the house, it's more practicle and allows more range of movement with less embarassment (especially some of the positions I lounge in). And it's hard work...
    AngelaDark AngelaDark 31-35, F 1 Response Aug 21, 2011

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    ~ My New Skirt ~

    if you dont have skirts? try this?
    Evangeline1985 Evangeline1985 26-30 Feb 7, 2013

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    My First Skirt Experience

    I've been into skin tight ladies clothing for many years. I have an obsession with panties and more recently wet look leggings, I've bought several pairs to wear around the house when doing the chores. Recently there has been a lot of flared, shiny 'skater' style skirts, which I...
    bonzodog bonzodog 56-60, M 1 Response May 30, 2013

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    ~ Skirts ~

    different perspective when people look at skirt length...i love all kinda skirts..as long as i have good body to carry it:)...
    Evangeline1985 Evangeline1985 26-30 2 Responses Feb 3, 2013

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    Wearing A Skirt Or Dress!

    Ever since I took notice in women I liked it when the dress or skirt was max 6 inches above the knee, no hire! I thought that is the highest I would wear mine! I figure with panties and pantyhose nothing could be seen any way! Well the first few times I did go out in public my...
    PJJA1000 PJJA1000 61-65, M 3 Responses Jan 18, 2013

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    I Really Like To

    I really love to wear a skirt in the summer time than shorts but there would be problem for me because I think it would alienate lot of family and friend that don't understand a skirt very comfortable and practical and should be a unisex garment to wear just like pants than again...
    notech64 notech64 41-45, M 8 Responses Jan 13, 2011

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    Wearing A Skirt

    I do like to wear denim skirts. I prefer wearing the longer maxi length skirt. I love the feeling of the breezes blowing around and under the skirt. I love the look of the skirt. I'll pair the skirt with some leggings. In the cooler weather I like the feel of tights. I...
    jml2000 jml2000 56-60, M 2 Responses Jun 10, 2013

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    I Enjoy Wearing Skirts

    I recently started wearing clothes that were deemed for women only. I love the feel of a skirt when I am walking around in my apartment. I feel the girl in me getting to come out when doing so. When I am not in a skirt I don't feel right...
    saraashley saraashley 31-35, F 4 Responses Aug 27, 2012

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    I spent a second day wearing a skirt on my

    travels through France. Stopped at lots of service stations for petrol food and coffee. I got quite a long state from a older lady. It seemed like she couldn't understand what she was seeing. I hope that I broadened some minds. Got to my holiday destination and checked in...
    Prettyjennifer2004 Prettyjennifer2004 51-55, M 2 Responses Jun 23

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    They Hide Everything!

    I love wearing skirts in the summer.   Nothing screams summer more to me then walking around in a summer skirt and flip flops.  The plus side to wearing skirts is that you can gain weight and have some extra padding on the hips and the skirt covers it all. ...
    reachin4goals reachin4goals 31-35, F 4 Responses Aug 3, 2007

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    I Love Wearing Skirts.

    I love wearing skirts because they are really comfortable. I wrote "Man Enough to wear a skirt and Woman Enough to wear a beard." I forgot to mention that I have a pair of black go-go boots that I wear with my double and gray. I can't believe it's been two years. The teenage boy...
    skirtmaster skirtmaster 61-65 2 Responses Oct 17, 2009

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    Mr

    well here goes first i think it is grate to no there is men out there who feel the same has me my first time is when i was invited to a party him to be her you know that kind of thing so that was the first time i put a skirt on and it was so grate to were in the hot summers day i...
    colinroberts04 colinroberts04 46-50 Nov 8, 2010

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    I Don't Understand

    I don't understand why there is no man's skirt, or its only very few... The skirt is comfortable, can be healthy in a warm summer day. I want to wear openly without feeling embarrassment, and not because i'm a crossdresser... i hate to boil my body in a pants. The female...
    VivienXX VivienXX 26-30, T 5 Responses Apr 15, 2010

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    Today I wore a skirt all day

    and travelled to France. I went to the channel tunnel terminal and walked around wearing a skirt. I bought petrol in France then stopped at many places to buy food and coffee all the time wearing a skirt. I checked into the hotel wearing a skirt. Nobody all day made any bad...
    Prettyjennifer2004 Prettyjennifer2004 51-55, M 3 Responses Jun 21

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    I love wearing Women's Skirts

    so much as a super sexy crossdresser. Normally I'm a size XL. The skirt I love wearing the most is the Women's Shiny Metallic High Waist Pencil Skirt in the color of Gold, because by the first time I wore it, I was feeling the super sex to go walking sexy. I was having the...
    deleted deleted 26-30 1 Response Apr 25

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    Back in June I had written my first story in

    this group about how my skirt experiences got started. I mentioned how my wife reacted when I told her about this. I had not expected this to go over too good with her and I was right, for the most part. Since my last story my wife and I had a more in depth conversation on this...
    Myotheridentity Myotheridentity 46-50 2 Responses Aug 7

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    So Many Different Styles

    I love to wear skirts. I think they are great and can be sexy. I like the comfort and freedom of my skirts. The cool air that can go up them. I am a male and I love to wear skirts.
    Adam59 Adam59 56-60, M Mar 30, 2013

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    So day three wearing a skirt in France.

    I spent most of the day in hotel wearing a different skirt today. Went down to breakfast and lunch in it. Then went for a walk into town to visit a bar all in my skirt. Then back to the hotel for dinner. In the evening I went down to listen to the live music in the town and...
    Prettyjennifer2004 Prettyjennifer2004 51-55, M 2 Responses Jun 23

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    Check out this maker of skirts

    for men. http://www.skirtcraft.com
    Prettyjennifer2004 Prettyjennifer2004 51-55, M 1 Response Jul 15

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    Related Experiences

    When I was young the miniskirt was all the rage and we loved wearing them. We used to get into trouble at school if our skirts were too short but mum was very good about our desire...
    Jilly53 Jilly53 56-60, F 1 Response Jul 31

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    Back in high school I would wear shorts on the winter but I'm excited for this winter to stop wearing shorts and start wearing skirts! Also I usually hate winter and the snow but I...
    Alexis117 Alexis117 18-21, T 1 Response Aug 6

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    When I was a teenager I loved wearing miniskirts. In fact I used to wear them as much as possible in preference to jeans, etc. to show off my legs. My mum used to let us wear...
    Jilly53 Jilly53 56-60, F 1 Response Aug 14

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    i love wearing wigs to change up my look so many woman make fun of me but they wear weaves.... i dont see whats wrong with wearing wigs every now and then lol is it wrong that i...
    momoayami momoayami 18-21, F a week ago

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    I love wearing granny panties the big pink ones are my fav
    Benbrian Benbrian 13-15, M 3 Responses Aug 5

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      So I'm a guy....and I am love wearing short shorts....I can't stand the styles they have today down at the knees....I like them mid thigh or shorter. I honestly haven't...
    ilovethongs23 ilovethongs23 41-45 4 Responses Aug 10

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    I love wearing all kinds of lingerie, and I especially like the kind that makes me feel like a sissy. I made this video when I was feeling a little sissyish. I hope you like it...
    VictoriaFredericks VictoriaFredericks 36-40, M 3 Responses Aug 12

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    I love wearing low-rise jeans or shorts with a low cut tank top that show off my belly and cleavage ;-)
    SexyBellyButton80 SexyBellyButton80 31-35, F 10 Responses Aug 17

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    I just find them so comforting and exhilarating. As you can read in some of my other stories, it began with bras as a pre-teen and grew slowly over the years. Now that I live on...
    LockedDarius LockedDarius 26-30, M 2 Responses a week ago

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    I think I do..... For about a year or so, with the exception of my school uniform, that's all I've worn.... I'm so used to them now that it feels strange not wearing one...
    SarahTheHooker SarahTheHooker 18-21, F Aug 20

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    I have several mini's. Love them all. This one I wore yesterday when I went to town. Did some shopping and visited the doctors office.
    Brandie1960 Brandie1960 41-45, M 6 Responses Aug 13

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    I really do! They're so comfy and a great substitute to dresses and skirts for me who isn't really the girly type! Perfect for summer
    Sasha0827 Sasha0827 16-17, F 3 Responses Aug 2

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    Hi, I am a pantyhose and tights wearing biker and attending lost of biker rally's and jol's,, I love to wear pantyhose and tights, so i will wear pantyhose under my normal riding...
    hosebiker hosebiker 51-55, M 1 Response 6 days ago

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    Yes, last saturday was my first whole day in flats. I started at a coffee shop showing my brown flats like wearing regular svoes, some glimpses but no more. I was wearing my...
    Bisbix Bisbix 41-45, M 1 Response Aug 12

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    Yes, It happened again. Yesterday night, the temperature was good and I proceeded to go roller skating wearing nothing else than one of my skating dresses. I choosed my very small...
    Nadia1977 Nadia1977 36-40, M 4 days ago

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    I'm wearing a lovely pair of French Knickers today :) They are purple with a pink waistband going round them. They feel wonderful and so sexy
    LisaTG LisaTG 26-30, T 1 Response Jul 29

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    I brought my first bra and suspenders set yesterday along with a sports bra and a Calvin cline top, and a pair of size 8 woman's jeans that are probably a size too small, I love...
    Incideofme Incideofme 36-40, M 10 Responses Jul 29

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    I'm wearing my wife's leopard print nightgown
    schumy schumy 31-35, M 9 Responses Aug 1

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    I like to wear shear to waist pantyhose to ***** clubs under short shorts. Of course I wear panties too. Also, I have a pair of black swade womens loafers and I wear a black clingy...
    lisapettie lisapettie 36-40 2 Responses Aug 2

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    I have worn lingerie for years. I started when I was in my early teens. Like most men who wear and start early, it was my mothers stuff that I found first. Things like stockings...
    Fullofstars Fullofstars 31-35, M 4 Responses Aug 3

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    I am a guy and have been wearing men shoes for my whole life, but yesterday when my shoes blew out I wanted a new pair of high tops, and no one in my town carries Converse so I had...
    icicle001 icicle001 36-40, M 2 Responses Aug 4

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    I am laying in bed feeling naughty wearing my Billabong tie side bandeau top costa blue scrunch butt bikini. Makes me happy and feels luxurious
    deleted deleted 26-30 1 Response Aug 10

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    Today I'm wearing underwear that belonged to my friends girlfriend . Grey cotton g string white bra . They feel so good and just the thought that she had them on drives me insane...
    toesforme toesforme 36-40, M 6 Responses Aug 12

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    My wife has me wearing matching satin Cacique bra and panties with black nylons, black flirty skirt, red top and my red 4" heels. Also all made up with a my brown curly wig and...
    nikkifemmdslave2 nikkifemmdslave2 36-40, M 4 Responses Aug 12

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    any ladies/girls wearing tight sexy leggings today? what type and colour?
    wheels1972 wheels1972 41-45, M Aug 16

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    I have to wear satin panties under my clothes and at home my wife has me take off my pants and teases me through them and she tells her friends and I do all the kinky things asked...
    CCstnt45 CCstnt45 46-50, M 9 Responses 5 days ago

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    I just saw a girl wearing short shorts and admired how she could fit an iPhone in the front pocket without having it fall out. Interesting!! From AEO of course! Tan color. Inspired...
    TransAsian TransAsian 26-30, T 1 Response 5 days ago

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    Ordered a few pair of "training bras" to get more used to wearing them daily. Hopefully they'll be here soon :)