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I Catch a Skirt Blowing Up In the Wind

Personal Stories, Advice, and Support 116 People

    My Stories.

    I like giving people a show so I sometimes go out commando in skirts/dresses that easily go up. I’ll share with you two of the best moments. I was wearing a purple, flowy, very-short (by that I mean just below the ***) dress and was getting off the subway. Normally there’s a...
    sexysweeet sexysweeet 18-21 1 Response Jul 13, 2010

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    What An Outstanding Day

    i've had the most wonderful day today. we had winds gusting up into the 60 mph range but it was still about 70 degrees. i made a visit to the college campus downtown and walked around. downtown, the winds get slightly accelerated by all the buildings. i was walking around...
    thisismyusername22 thisismyusername22 22-25, M 2 Responses Apr 7, 2012

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    Teachers Thong

    There was a really sexy teacher at my old school. She has a nice, wonderful and round arse. One day, we were doing a project, and she knelt down. This revealed a sexy, white lacy thong. I was so hard. I jizzed off happily at home! She had the perfect ****!
    egrve egrve 66-70 Apr 26, 2011

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    Full Frontal

    My wife and I had been posted to a new town and it involved quite a long drive through country areas. To spice the trip up a little I was constantly playing with items of my wife's clothing and continually undoing zips and buttons etc. I eventually talked her into letting me...
    citylivingcountryman citylivingcountryman 46-50 2 Responses Feb 24, 2011

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    Skirts Blowing On A Visit To London

    A few Saturdays ago I was walking down from London Waterloo Station down to the side of the Thames River by the Royal Festival Hall, when in front of me was a group of about six girls aged between 18 - 20. All the girls were either wearing skirts or dresses that in the windy...
    Robbies Robbies 41-45, M Jul 14, 2012

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    Wraparound Skirt Came Unwrapped

    I was walking from the parking lot into a large shopping mall one late spring morning. There was a woman ahead of me with a big purse and a shopping bag ahead of me and I did not think much about it until the wind started to nip at her skirt. I was thinking, nice tush, is there...
    eyeful eyeful 51-55, M 1 Response Aug 20, 2011

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    The First Time It Happened To Me

    I was on a business trip and I got tired of being in the hotel room so I dressed nicely and went to walk around the area. Then it happened. A gust of wind cought my skirt and lifted it some. I also remember catching it just in time so my panties and nylon tops didn't show...
    Josie06 Josie06 56-60, F 3 Responses Aug 5, 2010

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    Red-cheeked With Embarrassment

    The other day, I was taking my little girl for a walk in the park. I was wearing a cool, kicky sundress, the kind that hangs loose from the shoulders. There were lots of people about enjoying the sunshine and my daughter was skipping along beside me holding my hand. Suddenly, a...
    KristyLeigh02 KristyLeigh02 26-30, F 6 Responses Aug 19, 2011

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    Sexy Teacher

    I went to high school in a small farming town so the weather was usually very windy. A lot of girls wore skirts to show off their bodies and the teachers were no exception. The one day was extremely windy with about 50 to 60 mph winds. When school ended, I sat at a table inside...
    scarssymmetry scarssymmetry 22-25, M 3 Responses Aug 17, 2010

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    Nice Underwear

    I live near a suburban freeway with 3 lanes of traffic going in each direction . Outside of peak time  it is possible to cross 3 lanes to the medium ***** in the centre ,,wait there util there is clearance before completing to the far side . As I waited on the ***** ,a long...
    ginamontagu ginamontagu 31-35, F 5 Responses Aug 28, 2010

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    Oh My!

    several years ago (more than i'd like to remember), i worked for an airlines on maui. one day while working a flight on the ramp, a passenger was boarding the plane. the normal tradewinds were blowing so to say the least it was quite windy. as she got to the top of the steps a...
    deleted deleted 26-30 1 Response Jan 29, 2010

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    Beautiful And Pink

    It was my softmore year when I was just talking to my friends. This girl then walks out the building wearing a black mini skirt to cover up her juicy big beautiful booty. Just then a gust of wind came out of nowhere and blew up her skirt, revealing her cute pink panties and her...
    mrdac1234567891 mrdac1234567891 16-17 1 Response May 29, 2011

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    amazing view

    in town the other day, it was a really sunny day but really windy but girls still turned out in skirts and summer dresses and had already seen a load of flickering skirts with glimpses of panties and thongs. i end up being this slim asian girl who was wearing an extremely short...
    iloveupskirt iloveupskirt 22-25, M 3 Responses Jul 1, 2012

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    Related Experiences

    It seems like forever since I have last posted a story to this group. But I am happy to say that I have a new story to tell about Paula and her windy adventures in my life. The...
    scarssymmetry scarssymmetry 22-25, M 2 Responses Aug 2

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    My first skirt was a black and white very flowing and full ankle length with a side zipper and button closure, it didn't take long for a denim mini to show up followed by a maxi...
    CdKimmi CdKimmi 61-65, M 1 Response Aug 12

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    My family use to get so mad at me growing up they use to always say "we are not paying to heat the outdoors." but when it was October or even November and it was a crisp cool night...
    Chicgeekgal Chicgeekgal 22-25, F a week ago

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    I loved wearing miniskirts as a teenager and a young woman. I wore them in preference to jeans or trousers where possible. However, they did have their own hazard! One day, when we...
    Jilly53 Jilly53 56-60, F 5 Responses Aug 16

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    Has anyone ever seen or heard someone blowing a raspberry on a belly in public? I have a few times. Once when I was in infant school (elementary school) I was in the playground at...
    psychostudent psychostudent 18-21, M 2 Responses Jul 28

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    When I grew up I did at least in private and sometimes not so private wear short pleated skirts and the occasional pinafore style dress. This was not a punishment and indeed I am...
    littlegreyshorts littlegreyshorts 51-55, M 4 Responses Aug 1

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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...
    Myotheridentity Myotheridentity 46-50 2 Responses Aug 7

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    This has to be one of the worst and unchallenged stereotypes ever. Just because a boy is feminine, it has nothing to do with his sexuality. It's been my privilege to know many...
    MrsJoanieBNH MrsJoanieBNH 56-60, T 5 Responses 2 days ago

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    Skirts are so comfortable - especially when your most sensitive parts hang outside your body! And, really, skirts are as "feminine" as the Roman Army - badass lion fighting...
    steve66oh steve66oh 46-50, M 2 Responses Jul 28

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    After providing five years of great service my custom desktop with windows XP finally gave out. I ended up buying a new Dell with windows 8.1 preinstalled. At first I was...
    Jonathon11 Jonathon11 41-45, M Jul 29

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    My wife was miffed at me today. I thought it was because I was wearing a skirt last night. Turns out she had a beef with how I was discussing living arrangements with my 23 yr old...
    shadowplt shadowplt 46-50, M Jul 28

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    Today after a VERY early wake-up, (set my alarm to get up early yesterday) my dog heard it and woke me to go pee. Anyway, my wife cooked some great French Toast we did our...
    shadowplt shadowplt 46-50, M Aug 2

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    Yesterday I took a two hour drive to a swim meet in a nearby city. I worked as an official. I drove there wearing my skirt, heels and uniform shirt. Once at the pool I ditched...
    shadowplt shadowplt 46-50, M 1 Response Aug 10

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    Tomorrow I have to drive another two hours back to the city. This time to see an eye doctor. I had surgery on my right eye socket last February and I have to follow up with a...
    shadowplt shadowplt 46-50, M 3 Responses Aug 10

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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 Aug 14

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    I found my Skirt I want to buy and wear!! Victoria's Secret Easy Mixers The Lounge Skirt $29.50 JW-311081
    TransAsian TransAsian 26-30, T 4 Responses Aug 19

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    Apart from shorts, I have only been wearing dresses or skirts since I was 8 or something. And apart from the fact that my husband does not want to see me in trousers, I like...
    Susanna3 Susanna3 31-35, F 5 Responses 6 days ago

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    Behold the skirts for men come true!! http://www.thedailybeast.com/articles/2014/05/22/skirts-should-be-a-normal-choice-for-both-women-and-men.html Enjoy!! ;)
    TransAsian TransAsian 26-30, T 3 Responses 2 days ago

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    I have a wind chime at my window when the wind blows through its such a calming relaxing sound as the chimes moves and clangs off each individual chime. I sit with my eyes closed...
    Sweetgal40 Sweetgal40 36-40, F 2 Responses Aug 13

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    Well I tried on my first skirt today in 10 years and I wanted to know what y'all think about this outfit that I might get
    Karianne6614 Karianne6614 16-17, F 19 Responses Jul 30

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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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    Tonight I'm floating on my pool and enjoying a cool breeze. I'm wearing my fav pool skirt and writing this blog. Tomorrow I have an early wake up. I'm having cancer surgery again...
    shadowplt shadowplt 46-50, M 2 Responses Jul 31

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    Just wondering, if I've good shaved legs and 27 male, an it's 2014, should I show off my shaven legs in public or no in a skirt? I shaven my entire body. I love the feel of nicely...
    TransAsian TransAsian 26-30, T 4 Responses Aug 2

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    Spent the day dressed around the house. Heels, skirt and a nice blouse. Didn't really do much, just a day of relaxation. Something struck me. Why can't people be like our pets...
    shadowplt shadowplt 46-50, M 2 Responses Aug 3

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    I have worn dresses or skirts since i was 6 but i would love to live in a world where a boy can wear them openly instead of having to be called a cross dresser. i hope that day...
    jamie172 jamie172 46-50, T 9 Responses Aug 4

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    Jacked up skirt addict woman on drugs.
    hemititestone hemititestone 31-35, F Aug 6

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    A little conversation with my 3 year old daughter the other day. She was wearing a pretty little dress, spinning round so the skirts puffed out. She looked so cute. She turned to...
    Heellover Heellover 36-40, M 9 Responses Aug 8

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    I love to dress up and wear short dresses and skirts with a nice looking blouse or top. Also, I love to wear shorts and swimwear with hose and four inch high heels on.
    tammylynne tammylynne 41-45, F 8 Responses Aug 10

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    Though I only have a single pair of tiny leather ones.. but it sure is one of my favorite mini skirt! :)
    PoojaTimberlake PoojaTimberlake 18-21, F 4 Responses Aug 11

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    Today was a work day. Getting braver. Wore a skirt to McDonalds. Bunch of older folk there at the time. Whoops. A co-worker walks in and sees me. We converse and at work nothing...
    shadowplt shadowplt 46-50, M 3 Responses Aug 12

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    I'm Pentecostal so I have my reasons. Besides my religion, I enjoy wearing dresses and skirts instead of pants. Pants are so uncomfortable.
    PeaceBatman PeaceBatman 22-25, F 5 Responses Aug 16

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    My wife and daughter went to the city today to watch a movie. Had the house to myself. Mowed the yard and cleaned the house in my fav skirt and heels. Nice day.
    shadowplt shadowplt 46-50, M 3 Responses Aug 16

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    Am a very strict and experienced mistress and have been training newbies who have high interest in wearing skirts for so long and am willing to share my vast experience with you...
    bestmistress bestmistress 36-40, F 2 Responses Aug 17

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    I like to wear dresses or skirts - and preferably short ones - as often as I can. Partly because I like to feel - and look - feminine - and because my husbands loves to see me that...
    Susanna3 Susanna3 31-35, F 4 Responses a week ago

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    My wife, daughter and I accepted and did the ALS challenge. We're donating $30 to the cause. I challenge three of my circle to do the same. I did mine dressed in my favorite...
    shadowplt shadowplt 46-50, M 1 Response 6 days ago

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