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I Love Wearing Short Skirts

Personal Stories, Advice, and Support 1,002 People

    I Like Short Skirt And Boots

    this weekned i did not care what pepole think but i put on school skirt a white blouse coffee color pantyhose and knee high boots and my bra and my black wig i felt so good about my self i going to say a women all the time it great just to walk out in public being your self
    debbiehose debbiehose 56-60, M 4 Responses Sep 10, 2012

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    I am 48 years old and

    although I say so myself ,Im still in good shape for my age.I am 36DD 28 34, I used to be a formular 1 girl in the 80s, I worked as a ******** in Germany in the 90s and I married a millionare in 2001. My husband enjoys me in a very short skirt, we both play golf and he insists...
    patriciajohnson patriciajohnson 46-50, F 9 Responses 6 days ago

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    Short Skirts Are Lovely

    I am a cross dresser. I love the feel of a short skirt floating around my thighs. I find that when I have a short skirt on I am fare more conscious of my posture. I make an effort to stand straight. I have worn longer skirts and my legs do not look so good in longer skirts, they...
    Vanessacd1957 Vanessacd1957 51-55, M 3 Responses Sep 14, 2011

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    A Really Short Pleated Mini Skirt.

    Today I bought a really short mini skirt in London, I love it, it is grey and maybe about 5" above the knee so it will create plenty interest when I am travelling on public transport, I will have to wear my best knickers and stockings with this skirt as plenty people will see...
    deleted deleted 26-30 17 Responses Feb 29, 2012

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    Mid Thigh Is Best

    If I am in the mood to dress sexy I wear a mid thigh snug skirt with pantyhose and heels. I feel really sexy dressed like this. I like to walk around seeing my legs coming out if the short skirt. What more can I say other than I love shirt skirts.
    Adam59 Adam59 56-60, M 1 Response Mar 8, 2013

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    Love Mini Skirts

    love to wear short skirts with nice stockings, undies and heels. love the comments I get from women, from men it is mostly long looks
    Cissieall Cissieall 41-45, T 2 Responses Oct 15, 2011

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    Short Skirts

    In summer I go down to my local beach, It's usually fairly quiet where I go, as it's a fair way from cafe's etc. I'll spread my towel out on the warm sand, then venture down to the water. As I get deeper, the waves start to soak the short black flared mini skirt I am wearing...
    roadtooblivion roadtooblivion 56-60, M 5 Responses Dec 31, 2011

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    Short Skirts

    I love wearing short skirts but not to short
    xdpaul xdpaul 56-60, M 4 Responses Jun 10, 2011

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    I Love Guys Trying To Peek A Look.

    i love wearing short skirts around the house coz i know it drives my dad crazy. iv got a denim one that i wear with a black g string and skip around with at home. the other day i was wearing it while i looked in the fridge, i bent over with my legs spread a little so my dad could...
    deleted deleted 26-30 11 Responses Jul 27, 2012

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    Minis

    I like short skirts, short skirted dresses, minis, and I like micro minis, but I don't like a trashy look, it has to be right. I have long thin legs so I look ok in very short skirts, and it don't have too many angles, there's not a defined kind of anorexic look to my limbs. I...
    aoutdouze aoutdouze 18-21, F 3 Responses Nov 26, 2013

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    encamino67 encamino67 46-50, F 2 Responses May 4

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    I Think My Best Feature Is My Legs When I Cross Dress.

    And I want to show them off. In fact the shorter the better. If the tops of my stockings almost show or even sometimes do if I aren't careful is even more of a kick. In fact I like skirts so short that if I bend over the slightest bit my panties will show. Guess I pretty much a...
    RayanneA RayanneA 56-60, M Apr 11, 2012

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    Is there anything sexier

    than a short skirt worn with stockings fishnet and suspenders a nice pair of high heels nice bra ribbed top and sexy thong I love to tease men I know I'd love to be a naughty secretary being punnished by my boss with a cane across my skirt seat then sex over the filing cabinet
    caning caning 36-40 2 Responses Mar 22

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    not short short......

    my legs are my best feature.......so short enough to show off my legs as i walk....and maybe some thigh when i sit down.........
    SexySue4u SexySue4u 51-55, F 8 Responses Dec 27, 2013

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    10. Birthday Card

    Life was wonderful over the following months as both David and his mother were given their sexual satisfaction, and poor Frank was beginning to walk a bit bow legged, but he wasn’t complaining as he was having the time of his life. His joint wardrobe with Davids mother was...
    Mohangora Mohangora 56-60, T Aug 21, 2012

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    I'm loving the short skater style skirts at the

    moment. I have several in different colours. They are lovely to wear but also a little risque, especially when it's a bit breezy and there is a possibility that I may show my panties.......
    karenhobbs karenhobbs 26-30, T 5 Responses Apr 1

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    I Love Short Skirts

    I love wearing short skirts and I love women who wear short skirts that let you have a peek up them :-)
    DiaperedSissyLee DiaperedSissyLee 41-45, M 1 Response Aug 20, 2011

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    At My "t" Weekend

    I was away last weekend with my Trans group. It was real good fun being en femme all three days. I saved my shortest mini skirt until the last evening and I felt good in it. I was suprised how many nice comments I got from the other gurls. I did my best not to show my nickers...
    Vanessacd1957 Vanessacd1957 51-55, M 6 Responses Mar 27, 2012

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    Bought My Shortest Skirt Yet

    just today i went about the sales in town and came across a purple mini skirt reduced to a really low price so i went to try it on. i didn't realise til i put it on how short it really was... it literally just comes under my arse and when i go to sit down in it, my panties were...
    ron129 ron129 18-21, F 4 Responses Jun 26, 2012

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    I Love To Wear Them!

    I have always loved wearing skirts! I guess I really started to love them when I was a cheerleader! I loved the attention I got. Even after giving birth to twins and being pregnant again, I love showing off my legs! I still get quite the stares from men when I bend over and...
    deleted deleted 26-30 6 Responses Nov 26, 2013

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    Yesterday

    I wore a short brown miniskirt with a dark blue three buttons jacket, and under that I had on a black camisole (no bra no panties), and brown leather zip side calf length boots. I was working with the small team put together by the projects director, and the project manager for...
    bonizil bonizil 22-25, F 4 Responses Mar 6, 2013

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    I Love Guys Trying To Peek A Look!

    i love wearing short skirts around the house coz i know it drives my dad crazy. iv got a denim one that i wear with a black g string and skip around with at home. the other day i was wearing it while i looked in the fridge, i bent over with my legs spread a little so my dad could...
    deleted deleted 26-30 17 Responses Sep 17, 2012

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    12. The Second And Best Ever Birthday Present

    Frank lay on the bed with one hand stroking the heavily brushed beard of wool on his new white mohair cardigan whilst his other hand was busy fondling his erect manhood beneath their red mini skirt that he was wearing. She then reminded him about Saint ****, as he had fondly...
    Mohangora Mohangora 56-60, T Aug 21, 2012

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    I love to wear short skirts they make my legs

    look longer and you can just see which knickers I am wearing,wearing short skirts and feel as the wind as it gently blows around my legs and I just love to bend over to show my nicks of.
    Frillypink Frillypink 56-60, M 4 Responses Jan 14

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    My Short Skirts

    I always wear short skirts when I go out dressed up. Most are at mid thigh on me or a little shorter. I'm 6' 1" tall without my 5" heels on. I love to show off my long sexy legs and I love the attention they get from women and men. At home sometimes I'll wear longer skirts, but...
    deleted deleted 26-30 9 Responses Jul 23, 2013

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    Out at the local shopping center this morning

    in pleated black mini, lace topped hold ups going up and down on escalators, glass lifts and stairs. Nicely groped on the way home thank you, love that feeling of never even seeing the mans face x
    Leggylou Leggylou 31-35, F 6 Responses Feb 8

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    I Want Another Girl To Slip Her Hand Up My Short Little Skirt

    How fun to be dressing up and putting on your make up, when suddenly, you feel fingernails sliding up your thighs as you smooth on your lip gloss. Your concentration moves from the deep red liquid gloss to an increase in your own slippery liquid seeping into your panties. You...
    deleted deleted 26-30 2 Responses Jul 5, 2013

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    I Wear Short Skirts All The Time, All Year Long

    i agree with every one, nothing beats wearing a short skirt. i love the looks i get and the complements from men, and women too. i love it when the wind is blowing. thats when i wear a full skirt and lace string bikinies. they just go great together and i love showing them off...
    closet36 closet36 61-65, T 3 Responses Mar 16, 2013

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    Short Skirts And Woolen Tights

    I love to wear very short skirts and woolen tights. It's comfortable and looks very sexy.
    LizaBurns96 LizaBurns96 18-21, F 3 Responses Mar 26, 2012

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    No Underwear

    I love wearing short skirts especially without any underwear on, the thought of someone getting a glimpse is a huge turn on for me. I have often made sure that someone I like the look of gets a good look by bending over near them. I like wearing short skirts on public transport...
    deleted deleted 26-30 2 Responses Feb 16, 2012

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    11. My First Of Two Belated Birthday Presents

    Finally I sat my last exam. Now there was going to be a full three months before the results came out. Fortunately for me the County Hotel had given me another summer holiday job waiting on in the hotel restaurant. The money wasn’t brilliant but you got some good tips sometimes...
    Mohangora Mohangora 56-60, T 1 Response Aug 21, 2012

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    New Micro

    i just got a new denim micro mini skirt that is only 12 inches from waist to hem, by vanity and i love it. i have to wear leggings with it because everything shows. i want to wear it with my 6 strap garterbelt and stockings with a pair of cute panties for a lover sometime. that...
    Mizsuzy Mizsuzy 46-50, T 2 Responses Feb 6, 2012

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    Not Wearing Them But Looking At Them, For Sure

    This is one of the great inequities in the the man - woman discussion.  If a woman is wearing a MINI skirt, a man is helpless.  I have watched this phenomenon many times at malls, parties, bars......everywhere.  A woman in a mini skirt is irresistable to a mans eyes, he has...
    dadddyman dadddyman 51-55, M 1 Response Mar 21, 2012

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    I've been babysitting on weekends

    for about a year now and I'm very attracted to one of the kids I babysit's father. He's very handsome, young and muscular, and it turns me on just to see him :) I always wear something short and tight when babysitting so he'll see me after the night is over.
    slutbunny126 slutbunny126 16-17, F 9 Responses May 7

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    Related Experiences

      So I'm a guy....and I am love wearing short shorts....I can't stand the styles they have today down at the knees....I like them mid thigh or shorter. I honestly haven't...
    ilovethongs23 ilovethongs23 41-45 4 Responses Aug 10

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    When I was young the miniskirt was all the rage and we loved wearing them. We used to get into trouble at school if our skirts were too short but mum was very good about our desire...
    Jilly53 Jilly53 56-60, F 1 Response Jul 31

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    Back in high school I would wear shorts on the winter but I'm excited for this winter to stop wearing shorts and start wearing skirts! Also I usually hate winter and the snow but I...
    Alexis117 Alexis117 18-21, T 1 Response Aug 6

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    When I was a teenager I loved wearing miniskirts. In fact I used to wear them as much as possible in preference to jeans, etc. to show off my legs. My mum used to let us wear...
    Jilly53 Jilly53 56-60, F 1 Response 6 days ago

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    I really do! They're so comfy and a great substitute to dresses and skirts for me who isn't really the girly type! Perfect for summer
    Sasha0827 Sasha0827 16-17, F 3 Responses Aug 2

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    I have several mini's. Love them all. This one I wore yesterday when I went to town. Did some shopping and visited the doctors office.
    Brandie1960 Brandie1960 41-45, M 5 Responses a week ago

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    I was a teenage boy in the early 1980s and when I wore those shorts one of the things I liked most was how cool I felt on long hot afternoons. What was the thing you liked most...
    smoothlegs smoothlegs 41-45 3 Responses Aug 7

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    No..... Just no...... No....
    TheStillmanator TheStillmanator 13-15, M Aug 7

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    I love wearing low-rise jeans or shorts with a low cut tank top that show off my belly and cleavage ;-)
    SexyBellyButton80 SexyBellyButton80 31-35, F 6 Responses 4 days ago

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    I love wearing thongs so boys will see my thong and I wear my thong with a pair of low rise jeans and I like my but crack and thong is showing
    lauran2014 lauran2014 16-17, F 3 Responses Jul 21

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    So guys and girls I am needing some help.I am wanting to pic has my first pair of thongs.Any suggestions on brand,fabric,any bigger size,etc.I love wearing panties and I think...
    Bigboylovinpanties Bigboylovinpanties 18-21, M 1 Response Jul 23

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    I love wearing women's clothes. I just feel so right. The problem is that my body type doesn't fit this obsession. I seriously sometimes feel like I should be a girl.
    c455muscle c455muscle 22-25, M 10 Responses Jul 24

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    I love wearing make up!!! I feel better with make up on
    andreaespe andreaespe 18-21, F Jul 27

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    I love wearing granny panties the big pink ones are my fav
    Benbrian Benbrian 13-15, M 3 Responses Aug 5

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    I love wearing all kinds of lingerie, and I especially like the kind that makes me feel like a sissy. I made this video when I was feeling a little sissyish. I hope you like it...
    VictoriaFredericks VictoriaFredericks 36-40, M 3 Responses Aug 12

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    i love wearing my wifes clothing and going out for a drive in the car and maybe a walk
    funlover74 funlover74 36-40, M 4 Responses 4 days ago

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    Back in June I had written my first story in this group about how my skirt experiences got started. I mentioned how my wife reacted when I told her about this. I had not expected...