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I Love Wearing Skirts

Personal Stories, Advice, and Support 586 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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    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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    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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    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 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 3 Responses Sep 20, 2014

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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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    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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    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 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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    ~ 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 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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    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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    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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    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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    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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    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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    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 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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    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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    Related Experiences

    I love girls clothes as much as the next person on this experience and it all started several years ago when I was 10-11 years old and I don't know why this started and I don't...
    StarcraftsSwarm StarcraftsSwarm 13-15, T 2 Responses Jan 9

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    I love wearing leather skirts. Leather makes me feel so good inside about myself.
    Donna717 Donna717 36-40, F 3 Responses 5 days ago

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    Yes I do love wearing women's clothes. I love wearing those see through tops with a nice colorful bra under it. I love wearing a skirt with no pantie or some times I'll wear a...
    serinalynn serinalynn 61-65, M 8 Responses Jan 4

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    My wife and I love wearing pantyhose together, feeling that nylon clinging to you and rubbing our nylon covered bodies together feels so good. Check out our profile for more about...
    pantiescouple pantiescouple 26-30 2 Responses Jan 2

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    I love wearing high heels! However, I find that its very hard to find comfortable heels that I can stand in day in and day out. I recently found this amazing product that I thought...
    Heelswaps Heelswaps 26-30, F 1 Response Jan 13

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    I love modesty! I always feel so feminine in my skirts and have noticed people treat me more like a lady when I am in public. Boots in the winter and sandals in the summer go...
    bobbieshae bobbieshae 41-45, F 4 Responses Dec 30, 2014

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    I love skirts I have mostly worn short ones which are great cause they let everything breath. I love how it feels when you sit down with a skirt on!
    LexyCD LexyCD 18-21 Dec 27, 2014

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    It was the least I could do on a cold work day is wear my sun tan Sheer Energy pantyhose. I love the feel on me silky smooth legs. Especially when I wear them all day. It's a nice...
    marcycd12 marcycd12 41-45 4 Responses Dec 29, 2014

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    My dating began in the women shoe store. I went to a big shoe mall to buy heels. I was in 3 inch navy blue pumps. I was just looking at the racks for something new. sales girl...
    heellover4 heellover4 31-35, M 3 Responses Jan 14

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    Theirs just something so sexy about chokers, i love the way they look on certain girls necks and the way they feel on mine. The way they gently choke and caress your neck, makes...
    xXSamanthaCDXx xXSamanthaCDXx 31-35, M 2 Responses Jan 15

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    So yesterday I went out in public wearing opaque plum coloured tights and a black skirt, shirt, jumper and flats. I walked through the village to the local shop to buy some beer...
    Prettyjennifer2004 Prettyjennifer2004 51-55, M 5 Responses Dec 30, 2014

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    It has started really getting cold here. I was out with friends yesterday and it was really cold. My friends were all really cold, and they were surprised how it really did not...
    lovelivinglife lovelivinglife 22-25, M 2 Responses Jan 1

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    I want to be extremely fat so much. I had a giant custom fat suit made that makes me look huge and fat - over a100" waist. When I moved to Southern California a few months ago I...
    MAKVA MAKVA 56-60, M 1 Response 3 days ago

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    The moment I put on my red high heels I start getting all kinds of ideals I feel like I am on top of the world So I dance around until I twirled In my red high heels I can do...
    Goldenfairy Goldenfairy 26-30, F 3 Responses 1 day ago

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    Thongs and g-strings for me. They are my favorite and i love seeing others in theirs or talking about their thongs. All i think about are thongs and the ***** wearing thongs or g...
    thongluvr582 thongluvr582 31-35, M 3 Responses Jan 1

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    I've been wearing pantyhose for a very long time. I just love the feel of the smooth soft material. I get very turned on by looking at women's feet in nylons. I ********** in them...
    deleted deleted 26-30 1 Response Jan 6

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    ive been wearing for 6 years of my life never once regretted it. i love the feel of my tight skinny jeans on my *** when i have a thong on and i always wear pantyhose to work you...
    lovegfpanties lovegfpanties 18-21, M 10 Responses Jan 17

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    I love the feeling and warmth you get wearing a union suit, they feel like another layer of skin on your body.
    Smellyjeans Smellyjeans 46-50, M 2 Responses 3 days ago

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    I feel so sexy only wearing my bf large white tee with a cute thong and my hands resting on his shoulders barely grabbing his neck looking in his eyes biting my lip. Idk but i...
    bellavuira bellavuira 18-21, F 2 days ago

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    I always wear silky or satin panties 24/7. I usually only wear pantyhose during the day but have just bought some Wolford 9 Luxe 9 cosmetic to sleep in. It feels wonderful. Wearing...
    Prettyjennifer2004 Prettyjennifer2004 51-55, M 1 Response Dec 27, 2014

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    I couldn't agree more that wearing a guy's tee is def the most comfortable outfit. I like buying tees from the guys' department haha. They're all baggy and loose and it's super...
    Likeylalayys Likeylalayys 16-17, F 2 Responses Dec 27, 2014

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    I adore wearing beautiful bikinis! I miss the summer so much, and now being in winter I can't wear them :( This also acts as a treat for all the people, girls and boys who'd like...
    AmyGirlWinter AmyGirlWinter 18-21, F 6 Responses Dec 29, 2014

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    I have worn bras off and on over the past 35 years. I really enjoy wearing bras myself. I am a male off 67 years.
    Miltsch Miltsch 66-70, M 1 Response Dec 31, 2014

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    My first experience in a woman's one piece actually ended in me receiving my firsts blow job (from an older gentleman)! It was an amazing experience that kick started a life long...
    Medic72880 Medic72880 31-35, M 3 Responses Jan 1

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    I am transgender and been wearing nothing but gender neutral women's clothes do 7 weeks now. Except for when I swim. I swim for my workout . But I just ordered my first women's...
    DawnR59 DawnR59 51-55, T 1 Response Jan 1

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    Went to the mall yesterday wearing makeup. There were several ladies that noticed but the men didn't. Went into a jewelry store and was looking at earrings. I was looking at some...
    MsRobyn MsRobyn 51-55, T 6 Responses Jan 4

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    I to have been hooked by the allure of tights, I am 40 and have been wearing them since the age of 10, had my first O in them and try to wear them as often as possible along with...
    deleted deleted 26-30 1 Response Jan 4

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    I really started wearing women's clothing when I was the only guy on a trip to Mardi Grais. The four girls I was with said I was one of the girls and needed to dress that way on...
    Therealjason Therealjason 31-35, F 3 Responses Jan 5