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I Love Wearing Skirts

Personal Stories, Advice, and Support 631 People

    Check out this maker of skirts

    for men. http://www.skirtcraft.com
    Prettyjennifer2004 Prettyjennifer2004 51-55, M 1 Response Jul 15, 2014

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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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    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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    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 mentioned once before on here about dressing

    up in a cheerleader's outfit on Halloween one year. Well, I can definitely say one thing, skirts are a very different type of clothing. There is nothing more feminine feeling and freeing than the right skirt in the middle of summer. I just wish that I didn't have to keep this...
    tiffanyjoxd1989 tiffanyjoxd1989 22-25, T Mar 14

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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 3 Responses Jun 23, 2014

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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, 2014

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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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    ~ My New Skirt ~

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

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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 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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    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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    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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    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 Sep 20, 2014

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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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    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, 2014

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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 1 Response Feb 3, 2013

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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 2 Responses Apr 25, 2014

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    Related Experiences

    So tonight my parents went out of town so it was a total girls night for me. I've been trying to wear panties everyday for about a week now, so today I was already in my cute...
    CDcarly CDcarly 22-25, M 6 Responses Mar 29

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    don't you just love seeing skirts and dresses blowing around?
    drrjr drrjr 22-25, M 1 Response Apr 13

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    I love wearing High Heeled shoes,. It's viewed as a symbol of feminine frailty and makes me feel so feminine. I do wear sneakers and pumps etc, but when wearing a High Heeled shoe...
    KrisKrosSk8 KrisKrosSk8 26-30, F 6 Responses Mar 27

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    but people always say. "Why do you wear so much makeup?" Because I want to. "You're pretty even without makeup." thank you, I appreciate that. "Natural beauty is so much better...
    MechaKimochii MechaKimochii 18-21, F 1 Response Apr 5

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    wearing stockings, susspenders, full back nylon panties, under a little frilly mini skirt is what I love wearing . Mmmmm !
    mick69x mick69x 51-55, M 9 Responses Apr 10

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    I love wearing bikinis. I own more than 50 pairs and planning to buy more for my incoming beach getaway. Yes. I'm a bikini addict. Lol. :D
    Pinaybarbie Pinaybarbie 31-35, F 3 Responses Mar 26

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    I love wearing my pajamas considering my pajamas are 3 very fluffy diapers
    diaperpowder20 diaperpowder20 22-25, M 7 Responses Apr 9

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    My New Thigh High Calfskin Leather Boots! I just love wearing them out and about!
    leatherman2 leatherman2 51-55, M 1 Response Apr 15

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    i love wearing bikini briefs by vs there soft and comfortable. i primarily am in diapers all the time. but sometimes i wear those with a thick underpad
    DiaperRD32 DiaperRD32 31-35, T 1 day ago

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    I am thinking about wearing a blue jean pencil skirt on a road trip from SD to DEGA in 2weeks it takes us 18 hrs to do the trip. It would be three of us my 40 year old son and his...
    jerbare jerbare 56-60, M 3 Responses 6 days ago

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    i love being who i am i love that I'm a guy and that i am feminine so what if its not the norm i make my own norm!!!
    cuteinmypantiestoo cuteinmypantiestoo 26-30, M 2 Responses 4 hrs ago

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    Today I went out in a short black pleated skirt, thigh highs, black thong and my black high heel boots. I love the feeling when the wind lifts it up a little. Walking through the...
    chase6069 chase6069 36-40, T 5 Responses Apr 2

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    Love them so much!! Love the free feeling especially with no panties on 😊
    Sweetheart126 Sweetheart126 16-17, F 8 Responses Mar 31

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    Let me wear one for you, message me, ask for pictures, let me share my love of feminine wear with you, be my friend, accept me, let me be yours
    ForeverMe88 ForeverMe88 18-21, M Apr 15

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    Whilst living in Seattle, I came across an office block that used air conditioning Situated in the car park was a bank of very powerful expulsion fans – that propelled at a very...
    Billowingskirts Billowingskirts 51-55, M 5 Responses Mar 31

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    There are 4,588 of us here on EP who are willing to admit we love to wear women's clothes. I can only begin to imagine how many men there are out there who secretly enjoy wearing...
    silkydrawers silkydrawers 46-50 11 Responses 6 days ago

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    I've been wearing panties for 20 years often on and 24 seven for 10 years. I have on a nice silky pair of shadowline nylon today. My wife caught me way back while we were still...
    Mmorris352003 Mmorris352003 46-50 2 Responses Apr 17

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    I went out last week and did some banking wearing a pair of 6" platform heels. The trip included stopping at 2 banks, lowes, and a supermart I was wearing a pair of longer jeans...
    jerbare jerbare 56-60, M 2 Responses 6 days ago

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    Just been out for a lovely meal on holiday wearing a dress and heels that cost next to nothing and lots of people wanted to know which designer shop I bought my dress in I haven't...
    girlynicole girlynicole 36-40, F 1 Response Mar 27

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    I started doing this when I was prob 13 or 14. It's fun because you can already be wearing cheeky shorts then before you get into the pool you pull em off and you have bikini...
    AllyWood AllyWood 22-25, F Apr 1

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    It's a lovely warm spring day in the UK so I'm wearing a pretty silky if a bit skimpy and see through, strappy white top, pink skirt, matching lippy and nails, Woolford 10 denier...
    ris9358 ris9358 51-55, M 6 Responses Apr 6

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    im wearing one now but im gonna take it off soon
    dimplezz19 dimplezz19 13-15, F 2 Responses Apr 12

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