I Love Dressing Up In Skirts and Dresses

Personal Stories, Advice, and Support 560 People

    Wearing A Skirt

    I was in high school.  First, I got a lacy padded white bra with sexy little straps.  I would put that on and then I would add white panty's that had strings that wrapped around my hips.  I would obviously hide my monstrosity between my legs to look more feminine...
    KikkiNikks KikkiNikks
    26-30, T
    1 Response Nov 19, 2009

    I love dressing up in skirts

    and dresses. Which I do 7 days a week. I never wear pants or shorts...ever, never have in my entire life, never will. I celebrated my birthday tonight by going to Red Lobster for dinner. I wore a long sleeve multi-colored shirt, my new blue skirt (I got for my birthday), black...
    deleted deleted
    26-30
    Aug 29, 2015

    Wish I Could More Often

    I love wearing dresses and heels and skirts. I really do wish I had more opportunities to do so; it's kind of awkward to do so just for school. But damn, I look so gorgeous when I do! What to do, what to do?
    BrownEyedMystery BrownEyedMystery
    18-21
    Nov 16, 2010

    If I Had My Way

    i would be in skirts all the time if it were allowed by society maybe some day 
    spaz2692 spaz2692
    46-50
    Jan 3, 2012

    Torn between choosing what to wear this evening,

    I plumped for the following:- Matching black bra and panties. Black 'body' with a crotch fastening. Fitted sweater. Dark red opaque tights. Red heels. Genuine wool, red pleated mini kilt. Do you approve?
    AnnaliseB AnnaliseB
    31-35, T
    1 Response Mar 4

    A Free Weekend

    Whilst the wife was away...I took seized the opportunity. I spent most of the time in the apartment this weekend in women's clothes (mostly skirt/ blouse combos). I did venture out, dressed, to walk the dog in the dark before dawn. I loved the cool night breeze brushing across...
    JosetteLaRoc JosetteLaRoc
    36-40
    Jun 11, 2012

    There Is No Real Reason

    Why a man can't wear a dress or skirt granted there is some styles that are made for showing off the assets of a woman's body other than and no pockets there really is no reason . I think that a nice simple a line dress or shirtdress and wrap style dress comfortable and pactical...
    notech64 notech64
    41-45, M
    2 Responses Apr 1, 2011

    Observation In The Mall

    So today I went tot he mall to pay a few family bills, this is always a time for me to window shop, and check out what the women are wearing on a day to day basis. Its a great opportunity to people watch. So while waiting to be served I looked over my shoulder and here comes a...
    mpenner mpenner
    51-55
    2 Responses Jul 5, 2013

    I Love To Dress Up In Skirts And Dresses

    as a 16yr old i dont own any skirts but i do own dresses i love to wear dresses so much. i love wearing panties and pantyhose under the dress. i love the feel of the pantyhose over top my panties swishing with the skirt
    addguy3455 addguy3455
    18-21, M
    Sep 27, 2011

    Representing My Gender In The Best Possible Way

    Yes, I enjoy dressing in skirts, dress, high heels ... the whole nine yards. Why? Because I am a woman and I can. I like to look the very best I can as I represent my gender and in no way ever want to reflect poorly on women or on myself.
    Josie06 Josie06
    56-60, F
    4 Responses Aug 13, 2010

    This wasn't bad tonight.

    I bought 3 new skirts...1 blue, 1 white, 1 purple with black cheetah spots (which I'm wearing right now), 4 new pairs of Just My Size white nylon underwear (one pair I'm wearing right now) & 2 pairs of black knee-high socks (1 pair I'm wearing right now). With a grey T-Shirt, I...
    deleted deleted
    26-30
    Sep 21, 2015

    So the other day I was wearing my mini skirt

    around the house. My partner knows I wear it but know one else does. I had a lacy purple thong on under it. We have just built a house in a brand new estate so we have no fences, it was almost dark and I had to go out the back. I went out the back and as I did the lady behind my...
    Skimpythong Skimpythong
    26-30, M
    Dec 12, 2015

    Ofcourse I Do!!! Xd

    I love wearing this kind of clothing,short dresses and skirts, awesome XD It makes me look good and i can feel the wind under my....(I shouldn't say it)
    AngelsReflection AngelsReflection
    16-17, F
    1 Response Jan 6, 2010

    So the other day I was wearing my mini skirt

    around the house. My partner knows I wear it but know one else does. I had a lacy purple thong on under it. We have just built a house in a brand new estate so we have no fences, it was almost dark and I had to go out the back. I went out the back and as I did the lady behind my...
    Skimpythong Skimpythong
    26-30, M
    Dec 12, 2015
    deleted deleted
    26-30
    1 Response Feb 13

    I love wearing dresses & skirts.

    Do I really have a choice? That's what I wore everyday of the week my entire life, even in rain or snow. That's what all women should dress like. A strapless dress, long-sleeve turtleneck, black or brown knee-high socks, white bra & white underwear. Even in heavy wind, I had to...
    JamieLynnCarlin45 JamieLynnCarlin45
    46-50, F
    1 Response Oct 22, 2015
    deleted deleted
    26-30
    3 Responses Feb 13

    I love dressing up in dresses everyday.

    Every morning, I pick out my dress I'll wearing that day, then I pick which turtleneck or flannel shirt I'll be wearing that day, then I pick out which pair of knee-high socks (which is either black or brown), I'll be wearing, which bra (which is always nylon white), which pair...
    JamieLynnCarlin45 JamieLynnCarlin45
    46-50, F
    5 Responses Apr 2
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