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I Love Wearing Skirts

Personal Stories, Advice, and Support 549 People

    I recently purchased the skirt you can see in

    the picture which I am wearing which is a body contouring style made of soft polyester a wonderful multi purpose fabric. When I put the skirt on gave me a beautiful feeling of femininity and sensuality. I wore a white silky nylon and lace half slip underneath with a pretty bra...
    FontanaSlips FontanaSlips 41-45, M 3 Responses Sep 9

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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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    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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    ~ 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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    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 2 Responses May 30, 2013

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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 3 Responses Aug 7

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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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    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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    ~ My New Skirt ~

    if you dont have skirts? try this?
    Evangeline1985 Evangeline1985 26-30 1 Response Feb 7, 2013

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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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    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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    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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    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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    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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    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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    I just got my first skirt!

    Right now I'm sitting in my room doing homework wearing a skirt and panties, with my legs freshly shaven and a nice new coat of a royal purple nail polish on my toes. I feel so happy feeling this feminine and wearing a skirt for the first time.
    jjthom jjthom 22-25, M 2 Responses 2 days ago

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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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    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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    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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    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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    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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    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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    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 Apr 25

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    Related Experiences

    Today I dressed up femininely in the dress you can see in the picture and it gave me a beautiful feeling of femininity and sensuality. The dress is a body contouring style made of...
    FontanaSlips FontanaSlips 41-45, M 1 Response Sep 9

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    I love wearing anything nylon and feminine. The more feminine, the better! I love to wear lace trimmed nylon panties, slips, baby doll nighties and nightgowns. I also love to wear...
    closetedcd60 closetedcd60 56-60, M 4 Responses Sep 12

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    hello i love wearing boilersuits, im a plumber and stand out wearing them, but like to have my work close clean under them for going to shop for lunch, etc ,
    coyle88 coyle88 22-25, M Aug 31

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    I love wearing shorts with a hoodie and vans but I don't like wearing a shirt under the hoodie. The most perfect outfit I like to wear ^~^ it's comfy
    ShantaleeCx ShantaleeCx 13-15, F 3 Responses Sep 8

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    Ever since I was 10 I have loved wearing tights esp ballet tights. I also love men in tights. I have never done ballet but would love too. The problem is that in the UK there are...
    balletprince balletprince 41-45, M 2 Responses 3 days ago

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    I love wearing sissy lingerie and my wife buys my lingerie
    rimonty59 rimonty59 51-55, M 6 Responses Aug 30

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    I love wearing my nice silver shiny high heels. I'm 4'10" n my shoe size is 5. I look so chic in them. They almost look like the Disco shoe from the 1970s. Disco Rules!
    DiscoNight1970s DiscoNight1970s 46-50, F 9 Responses Sep 4

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    I'm almost exclusively living in women's clothes, now. I have a job where I can work from home a lot, so I only have to put on menswear when I have to go to the office. And...
    KatieTreat KatieTreat 51-55, T 4 Responses 23 hrs ago

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    I am very passionate about wearing a kilt. I have had a Friday off from work - my first day off in a long time. I have been working 7 days a week for the past few weeks. I...
    mancblue mancblue 51-55, M 3 days ago

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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 Aug 24

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    I love myself wearing men clothes! For example borrowing (or stealing lmao) a t-shirt or a hoodie and wearing it <3
    dropdeadwilma dropdeadwilma 16-17, F 10 Responses Aug 29

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    hehehe you wouldn't believe this...but look down at the story I wrote on August 14th. I'm still wearing those clothes!!!! Still! That is 23 days without changing clothes! It is...
    TotTotTotTot TotTotTotTot 18-21, F 2 Responses Sep 6

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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 Aug 23

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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 Aug 23

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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 :)
    artsyguy86 artsyguy86 26-30, M 1 Response Aug 24

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    I'm laying in bed and wearing a nappy im about to have a huge **** I've keep in all morning. I'm now doing it along with a having a pee it feels good im planning to stay in it all...
    london560 london560 41-45, F 2 Responses Aug 25

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    I'm wearing a jockstrap right now at work! Who else wears there's to work?
    andyj1987 andyj1987 26-30, M 3 Responses Aug 28

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    I am wearing to sleep my new Mycrox- d black leggings. They are very soft and smooth
    kamilatv kamilatv 46-50, M 2 Responses Sep 7

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    Yes please <3 (I was wearing shorts underneath calm down)
    ColourfulDreams ColourfulDreams 13-15, F 1 Response Sep 8

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    I just love it when I show my body off to other people, most of the time they come up to me and start talking to me even girls who I think are much prettier than me, I'm still...
    Smexyshannonxo Smexyshannonxo 13-15, F 2 Responses 1 day ago

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    I bought a pair of black women's clogs earlier this year hoping they'd both look nice and not make me roll my ankles like my men's dress shoes do. I've been happy with them from...
    ia16 ia16 36-40, M 2 Responses Aug 29

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    I love women that wear sexy bra . It make they breast look so beautiful and sexy . I wish more guys would enjoy it instead of the naked version.
    flex0712 flex0712 31-35, M 4 Responses Aug 30

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    I remember the day when i started wear hijab .. i feel like having another leather skin on my head.. but i still love to cover my head as obligation along with lifestyle thats why...
    fizamahmood fizamahmood 36-40, F 1 Response Sep 5

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    People always tell me "aw man it must suck to always have to wear a tie to work" the fact could not be farther from the truth. If it was appropriate I would wear a suit too. I love...
    Legionicula Legionicula 36-40, M 1 Response Sep 5

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    Here are my new heels I love them
    Disturbedheels Disturbedheels 26-30, M 2 Responses Sep 10

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    Summer's over and fall means the beginning of boot season. I'm tempted to buy a new pair of brown or black high-heeled thigh boots to wear with a short tight little sweater dress...
    Vboots Vboots 26-30, T 3 days ago