I Love Wearing Skirts

Personal Stories, Advice, and Support 927 People

    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
    1 Response Oct 17, 2009

    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
    6 Responses Aug 27, 2012

    Tbh I could die in an American Apparel tennis

    skirt and I think that would automatically make it a fortunate death. 👍🏻
    spoiledsweetforever spoiledsweetforever
    18-21, F
    4 Responses Jan 27, 2016

    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

    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
    7 Responses Jan 13, 2011

    I love wearing skirts

    because what I wear under them, like today I'm wearing a smart knee length pink skirt with two pleats on the front and one on the back, I'm wearing black stockings with a pink six clip suspender belt and the knickers I'm wearing are a peach control thong that's waist high...
    tightjane tightjane
    41-45, F
    3 Responses Oct 28, 2015

    ~ 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
    1 Response Feb 3, 2013

    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
    61-65, M
    2 Responses Jun 10, 2013

    Check out this maker of skirts

    for men. http://www.skirtcraft.com
    deleted deleted
    1 Response Jul 15, 2014
    jessica1959 jessica1959
    56-60, M
    2 Responses Nov 2, 2015

    Who are Best Response Media.

    A british company who are invading my space ? Kiltiekid.....8.4.16.
    kiltiekid kiltiekid
    70+, M
    Apr 7, 2016

    So.... I have this dream

    where my family is going to thanksgiving dinner. I was ranting about nothing to wear and my wife says you should wear that blue skirt and these black stockings... 😳 I felt tingles all over my body when she said that! ( she hates that I dress) So I sheepishly slip on the...
    VeronicaNpantyhose VeronicaNpantyhose
    Nov 21, 2015

    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

    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
    2 Responses Feb 11, 2013


    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
    Nov 8, 2010

    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
    3 Responses Sep 5, 2010

    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

    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
    2 Responses Apr 25, 2014

    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
    3 Responses Aug 3, 2007

    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...
    deleted deleted
    2 Responses Jun 23, 2014

    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

    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
    26-30, M
    5 Responses Sep 20, 2014

    I'm a boy, who likes to dress up in girls

    clothes. I want a girl to talk to me.
    devan1234 devan1234
    18-21, M
    1 Response Feb 13, 2016

    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...
    deleted deleted
    3 Responses Jun 21, 2014

    ~ My New Skirt ~

    if you dont have skirts? try this?
    Evangeline1985 Evangeline1985
    3 Responses Feb 7, 2013

    If I had a choice between wearing a dress

    or wearing skirts I really think that skirts would win out. I have 2 pencil skirts that I just adore and another shorter skirt that I don't wear too often. It feels good to match it up with a nice blouse or sweater, depending on the weather or mood. Anyone else like skirts more...
    ReneeTalley ReneeTalley
    61-65, M
    6 Responses Feb 19, 2016

    Been wearing my Skirts,

    by gender they are Gentleman's Skirts, for thirty years. No one has time to bother what I wear. I like to look smart or casual. definitely a man in a Skirt. Do they all wear skirts where I come from. no one really cares. I will stand beside a lady wearing a skirt. There are...
    kiltiekid kiltiekid
    70+, M
    2 Responses Jan 24, 2016

    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...
    deleted deleted
    3 Responses Jun 23, 2014
More Stories