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I Love Wearing Shorts In The Winter

Personal Stories, Advice, and Support 88 People

    Christmas Hike

    It was cold, it was wet, but today I had a long walk wearing black shorts. I could feel the rain running down my bare legs and it was worth it. I try to stay in shorts as much as possible and today looked like a good opportunity.
    jamieq1 jamieq1 26-30 1 Response Dec 25, 2012

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    Pleasant Surprise At A Zebra Crossing

    Chilly this morning (December 10th) wasn't it? Freezing fog early on: a bit of thin, watery sun by 10 o'clock, but temperatures hardly above zero. So there I was, driving my bus into Stevenage Old Town, when I had to stop at a zebra crossing - to allow a couple of fortysomething...
    xsadidas xsadidas 56-60, M 2 Responses Dec 11, 2012

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    My Friend Wears Shorts All Year

    I know only one person who wears shorts all year: he's my class mate, he came to our class last September. He wears shorts because his parents are strict and they make him wear shorts All other boys wear long trousers after September October. He says he's not cold even when it's...
    isoldaomol isoldaomol 13-15, F 2 Responses Jul 27, 2012

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    I Love Wearing Shorts In The Winter

    I always wear shorts. I wear them everyday at school and I got a job delivering pizzas and we can wear shorts to work so i do. They are more comfy for me than jeans. In the winter i just thrown on a sweatshirt or jacket. My legs don't get as cold and I like the feeling of the...
    dirkgreer dirkgreer 18-21, M 4 Responses Nov 17, 2013

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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'm super excited for it to snow this year!
    Alexis117 Alexis117 18-21, T 1 Response Aug 6

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    I'm In Shorts No Matter How Cold It Is

    Ever since I started working at an amusement park, I've had to wear shorts, it was part of my uniform. I wasn't always open to wearing shorts, most of the time I was in pants. I didn't like showing my legs off, but I had no choice when it was a requirment of the job. I finally...
    speedracer80668 speedracer80668 41-45 1 Response Jan 5, 2012

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    More Attention In The Winter

    I do love wearing shorts in the winter. I do it because I like the sensation of freedom, and the heightened sensations of temperatures and air movement. I also like that it is an expression of my dislike of other people expecting me to confirm to their clothing choices. Of...
    pelerine pelerine 41-45, M 2 Responses Mar 11, 2013

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    Walking In Shorts With Friend In The Winter When We Were 13

    We had no uniforms in school. Was allowed to wear shorts to school, but not in the winter. I wore shorts from April or May to October, and was unhappy from October to May. When I was 13, one boy who also liked to wear shorts came to class. Sometimes during winter holidays, while...
    bareknee bareknee 46-50, M 4 Responses May 15, 2012

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    It's Not That I Like Shorts

    It's that I just hate pants. They tend to not be too flattering on me. I like to wear shorts or skirts in the cold. It gives me a very awake feeling. I just like it.
    MyUnspokenWord MyUnspokenWord 18-21, F 1 Response Jan 7, 2013

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    Long Time Shorts Fan.

    I am a freethinker so do not care about conventional dresscodes. It's up to me how I dress, thats freedom of expression. That means it is up to you too. I respect that. It makes me wonder why people judge people who are like us. I would never do anything to offend public decency...
    deleted deleted 26-30 2 Responses Sep 2, 2012

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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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    All I wear is shorts hahaha I never wear pants. I live in Australia though so it's pretty hot in summer but cold in winter :')
    maxbondy maxbondy 13-15, M 1 Response 2 days ago

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    I just saw a girl wearing short shorts and admired how she could fit an iPhone in the front pocket without having it fall out. Interesting!! From AEO of course! Tan color. Inspired...
    TransAsian TransAsian 26-30, T 1 Response Aug 23

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

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    I love wearing short shorts, they really don't feel as revealing as they look but whenever I wear them they make me feel sexy. I have not worn them outside because I'm a little...
    thom2332 thom2332 22-25, M 3 Responses 1 day ago

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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 13 Responses Aug 17

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    i love wearing wigs to change up my look so many woman make fun of me but they wear weaves.... i dont see whats wrong with wearing wigs every now and then lol is it wrong that i...
    momoayami momoayami 18-21, F Aug 22

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    hello i love wearing boilersuits, im a plumber and stand out wearing them, but like to have my work close clean under them for going to shop for lunch, etc ,
    coyle88 coyle88 22-25, M 1 day ago

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    I love wearing granny panties the big pink ones are my fav
    Benbrian Benbrian 16-17, 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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    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 love wearing sissy lingerie and my wife buys my lingerie
    rimonty59 rimonty59 51-55, M 3 Responses 1 day ago

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    I like to wear shear to waist pantyhose to ***** clubs under short shorts. Of course I wear panties too. Also, I have a pair of black swade womens loafers and I wear a black clingy...
    lisapettie lisapettie 36-40 2 Responses Aug 2

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    100% love them I hate wearing pants so this is next best thing lmao
    Angel2345 Angel2345 13-15, F 3 Responses Aug 14

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    Dresses are cooler to wear than shorts but shorts are much sexier..especially if u have tanned legs . And with our usually intemperate summers in uk its nice to b able to put a...
    prettyflamingo prettyflamingo 41-45, F 2 Responses Aug 13

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    Hi, I am a pantyhose and tights wearing biker and attending lost of biker rally's and jol's,, I love to wear pantyhose and tights, so i will wear pantyhose under my normal riding...
    hosebiker hosebiker 51-55, M 1 Response Aug 22

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    Yes, last saturday was my first whole day in flats. I started at a coffee shop showing my brown flats like wearing regular svoes, some glimpses but no more. I was wearing my...
    Bisbix Bisbix 41-45, M 1 Response Aug 12

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    I just find them so comforting and exhilarating. As you can read in some of my other stories, it began with bras as a pre-teen and grew slowly over the years. Now that I live on...
    LockedDarius LockedDarius 26-30, M 2 Responses Aug 21

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    Yes, It happened again. Yesterday night, the temperature was good and I proceeded to go roller skating wearing nothing else than one of my skating dresses. I choosed my very small...
    Nadia1977 Nadia1977 36-40, M Aug 24

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    I love myself wearing men clothes! For example borrowing (or stealing lmao) a t-shirt or a hoodie and wearing it <3
    dropdeadwilma dropdeadwilma 13-15, F 10 Responses 3 days ago

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    my experience since 18 i have loved soffe especially the slickster Do you love them?
    madi107 madi107 18-21 Aug 15

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    Can't stop wearing tights and panties. The feeling is just incredible. I love having them on in public under my trousers, makes me feel so naughty.
    LoveWearingTights LoveWearingTights 22-25, M 16 hrs ago

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    I'm wearing my wife's leopard print nightgown
    schumy schumy 31-35, M 9 Responses Aug 1

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    I have worn lingerie for years. I started when I was in my early teens. Like most men who wear and start early, it was my mothers stuff that I found first. Things like stockings...
    Fullofstars Fullofstars 31-35, M 4 Responses Aug 3

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    I am a guy and have been wearing men shoes for my whole life, but yesterday when my shoes blew out I wanted a new pair of high tops, and no one in my town carries Converse so I had...
    icicle001 icicle001 36-40, M 2 Responses Aug 4

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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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    I am laying in bed feeling naughty wearing my Billabong tie side bandeau top costa blue scrunch butt bikini. Makes me happy and feels luxurious
    deleted deleted 26-30 1 Response Aug 10

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    Today I'm wearing underwear that belonged to my friends girlfriend . Grey cotton g string white bra . They feel so good and just the thought that she had them on drives me insane...
    toesforme toesforme 36-40, M 6 Responses Aug 12

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    My wife has me wearing matching satin Cacique bra and panties with black nylons, black flirty skirt, red top and my red 4" heels. Also all made up with a my brown curly wig and...
    nikkifemmdslave2 nikkifemmdslave2 36-40, M 4 Responses Aug 12

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    any ladies/girls wearing tight sexy leggings today? what type and colour?
    wheels1972 wheels1972 41-45, M Aug 16

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    I think I do..... For about a year or so, with the exception of my school uniform, that's all I've worn.... I'm so used to them now that it feels strange not wearing one...
    SarahTheHooker SarahTheHooker 18-21, F Aug 20

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    I have to wear satin panties under my clothes and at home my wife has me take off my pants and teases me through them and she tells her friends and I do all the kinky things asked...
    CCstnt45 CCstnt45 46-50, M 9 Responses Aug 23

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    Ordered a few pair of "training bras" to get more used to wearing them daily. Hopefully they'll be here soon :)
    artsyguy86 artsyguy86 26-30, M 1 Response a week ago

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    I'm laying in bed and wearing a nappy im about to have a huge **** I've keep in all morning. I'm now doing it along with a having a pee it feels good im planning to stay in it all...
    london560 london560 41-45, F 2 Responses a week ago

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    I'm wearing a jockstrap right now at work! Who else wears there's to work?
    andyj1987 andyj1987 26-30, M 2 Responses 4 days ago

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    I love for somebody to chat with on here. If you love tights and wanna be my master message me
    Sissyboy696969 Sissyboy696969 13-15, M Aug 10

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