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I Love Wearing Skirts

Personal Stories, Advice, and Support 746 People

    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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    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

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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 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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    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 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 4 Responses Sep 20, 2014

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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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    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 26-30 3 Responses Jun 21, 2014

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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 26-30, T 3 Responses Mar 14

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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 4 Responses Jan 18, 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 1 Response Oct 17, 2009

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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 3 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...
    deleted deleted 26-30 2 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 5 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...
    deleted deleted 26-30 2 Responses Jun 23, 2014

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    Check out this maker of skirts

    for men. http://www.skirtcraft.com
    deleted deleted 26-30 1 Response Jul 15, 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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    ~ My New Skirt ~

    if you dont have skirts? try this?
    Evangeline1985 Evangeline1985 26-30 2 Responses Feb 7, 2013

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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 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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    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

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    Related Experiences

    I am a 15 year old bit and ever since I was young I have loved wearing high heels and I have mastered walking in them. My cousin likes to party so I normally wear hers as they are...
    Alluakbar69 Alluakbar69 70+, T 1 Response 5 hrs ago

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    I love wearing a kilt because of the freedom and also because I wear knickers under.I try to wear one of my kilts as often as possible
    benafric benafric 70+, M 9 hrs ago

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    Does anyone else enjoy the feeling of straps under there clothes.? Tanks-camis-bra-full slip.??? Men just don't have anything with straps. Im just so at ease wearing anything with...
    Kittenkiss76 Kittenkiss76 61-65, M 7 Responses 1 day ago

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    I love wearing heels in bed..... So sexy
    thighspread thighspread 18-21, F 5 Responses 1 day ago

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    I just love wearing women's clothes. The feeling I get is just so unimaginable. I still remember the first time I have started do it and I'm so excited that I gave in back to it...
    12rak38 12rak38 36-40, M 6 Responses 2 days ago

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    I love leather fashion. I love the look of this outfit. It is great to wear. I love the shine on the leather. I think leather is sophisticated, smart and sexy all at the same time...
    rockerlinda15 rockerlinda15 22-25, F 1 Response 2 days ago

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    I first started wearing union suits during the coldest part of winter. I wore thermals other times basically October to April. I like the one piece aspect of union suits.
    coverallfan coverallfan 41-45, M 2 Responses 2 days ago

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    I've been wearing women's clothing for many years and, when home, wear them almost exclusively. Recently I went on Google to take a look at the house I lived in for several years...
    janusatv janusatv 61-65, T 8 Responses 4 days ago

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    i always wear skirts and it makes me feel pretty and people call me cute sometimes and it's just makes my day
    strawbby strawbby 13-15, F 5 days ago

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    I like to wear military uniform mostly. I have some older Russian ones from when the Soviet Union was still in existence. I love the way the uniform feels. I have tall leather...
    skylardo skylardo 26-30, M 2 Responses 5 days ago

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    I have worn ladies chunky aran cardigans for years. I always liked the cosy feel of wearing ladies button through cardigans.I try to find unisex cardigans which button to my neck...
    cardiganlover cardiganlover 61-65, M 5 days ago

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    I didnt start wearing stockings until I was 18 and understood the power stockings had over men :) I wore thigh highs in my teen years, was like wearing stockings, but its not the...
    satnlacy satnlacy 22-25, T 5 Responses 6 days ago

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    Beautiful day so it's on with a nice red bikini and straight in to the garden :) I love bikini tan lines, feels great to be outside :)
    GirlyLisaTG GirlyLisaTG 26-30, T 2 Responses 6 days ago

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    Hello everyone! I'm a guy and I love to wear heels. Maybe I love high heels more than my girlfriend. I use to wear them and watch my female part in the mirror and I like it a lot...
    CDL17 CDL17 18-21, M 5 Responses 6 days ago

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    I love them and wear them most of the time i am dressed and going out the look and feel with the stockings are so nice plus the advantage of the fact of panties come off easier
    alexiswcd alexiswcd 56-60, T 2 Responses 6 days ago

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    Love to see a woman in lingerie or cute underwear.
    grandpaj grandpaj 61-65, M Aug 20

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    I'm a sales rep. at Macy's. The one thing I like is I can wear a dress everyday. I always wear a black dress with a black shirt, black polo short sleeve in the summer a long sleeve...
    deleted deleted 26-30 2 Responses Aug 20

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    I love duct tape to be my perfect gag I like it more with the camo tape and just keep it tight on my mouth or around it
    MaxwellMoonHoof MaxwellMoonHoof 18-21, M Aug 19

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    Hey I am sorry my English is so poor.i am 30yes old and I started to wear panty and nightgown jus few yes back and my wig helping me out with it I love to do shopping with her. I...
    daya55 daya55 31-35, M 1 Response Aug 19

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    I love wearing women's panties it feels so good against my balls. I am totally straight but the sensation I get is second to none when I am wearing panties!!!
    pantyboy30 pantyboy30 26-30, M 3 Responses Aug 19

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    Satin skater skirts are so lovely. I love wearing them. They feel so comfortable and makes me feel so feminine. I adore women who wear short skirts and do respect them a lot. I...
    Pinkygir Pinkygir 16-17, M 1 Response Aug 18

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    I love to have sex with my wife wearing high heels, it is so hot and different just to feel fem and dominant at the same time
    bdavidlatin bdavidlatin 41-45, M 2 Responses Aug 17

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