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I Love Wearing Shorts In The Winter

Personal Stories, Advice, and Support 82 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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    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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    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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    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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    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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    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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    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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    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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    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

    I have loved wearing women's shoes and boots since I was a child. I wear them in public now after only wearing them indoors for years.
    hh4evry1 hh4evry1 36-40, M 9 Responses Jul 14

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    I love wearing them! They look and feel good :)
    JennyRose2 JennyRose2 13-15, F 3 Responses Jul 12

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    i love wearing pink leather ballet slippers and ballerina outfits i cant help it it turns me on lol
    deleted deleted 26-30 1 Response Jul 17

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    i love wearing pink ballet tights with a pink silk leotard or pink silk ballet dress
    deleted deleted 26-30 1 Response Jul 17

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    i love wearing anything related to ballet as long as its pinklooking for friends that share the same
    deleted deleted 26-30 Jul 17

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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 9 Responses Jul 24

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    I love wearing make up!!! I feel better with make up on
    andreaespe andreaespe 18-21, F 4 days ago

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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 day ago

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    When I wear boy shorts to work as my outerwear, I don't wear panties underneath. I admit I like getting the looks that I do!
    Paca24 Paca24 18-21, F 8 Responses a week ago

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    It's been four days now, and I haven't changed clothes at all! I've not seen anything that is underneath my clothes for all that time, I haven't even pulled them down to go to the...
    TotTotTotTot TotTotTotTot 18-21, F 1 Response Jul 18

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    I'm wearing purple bikini style panties, black and white yoga shorts, cheetah bra, and a black tank top to bed 😏😍
    sammixdress sammixdress 18-21, M 3 Responses 5 days ago

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    I actually enjoy all the seasons but winter lands on me in a big way. My home is way off the beaten path and winter can come very early. South Dakota got walloped last October and...
    EdwardTeach EdwardTeach 46-50, M 1 Response Jul 18

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    Cleaning Out the Closet I have been cross dressing for many many years and have acquired a collection big enough to fill a walk in closet. Some of the items I have date all the way...
    jamie50 jamie50 51-55 5 Responses Jul 3

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    my favorite panties, especially when they're boy shorts
    lilnymph lilnymph 18-21, F 2 Responses Jul 13

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    I wish I could wear short shorts like all the girls do!! Why men have to wear shorts to their knees?? It's just Not Right!! Ugh. An I don't know where to buy the short shorts...
    TransAsian TransAsian 26-30, T 6 Responses 1 day ago

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    All my shorts almost reveal my but cheeks
    teenally teenally 13-15, F 9 Responses Jul 18

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    I like wearing a mini skirt whenever I can. It makes me feel young and sexy, showing off my smooth long, tanned legs. Right now I'm wearing my tan denim mini, a black cami, and...
    SandyBG SandyBG 56-60, T Jul 4

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    I like wearing a mini skirt whenever I can. It makes me feel young and sexy, showing off my smooth long, tanned legs. Right now I'm wearing my tan denim mini, a black cami, and...
    SandyBG SandyBG 56-60, T Jul 4

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    I like wearing a mini skirt whenever I can. It makes me feel young and sexy, showing off my smooth long, tanned legs. Right now I'm wearing my tan denim mini, a black cami, and...
    SandyBG SandyBG 56-60, T 1 Response Jul 4

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    I like wearing a mini skirt whenever I can. It makes me feel young and sexy, showing off my smooth long, tanned legs. Right now I'm wearing my tan denim mini, a black cami, and...
    SandyBG SandyBG 56-60, T Jul 4

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    I wear chokers a lot (I'm actually wearing one in my profile picture). My neck is quite long and slender, and I wear them tight around the middle of my throat. Two nights ago I...
    fragilethroat fragilethroat 22-25, F 2 Responses Jul 19

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    It was great when I was 12, 13 & 14 and I could get away with wearing a girls two- pice skimpy bikini, since my lack of full boobs wasn't such a giveaway at that age. I loved...
    LuvToWear LuvToWear 22-25 1 Response Jul 23

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    Cleaning out the closet IIAfter the wife left for work, I went and pulled out my oldest trash bag full of clothes and heels and then went and took a shower. I figured I better run...
    jamie50 jamie50 51-55 8 Responses Jul 4

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    I wear sexy lingerie everyday. I love how it feels against my skin. I work for a lingerie company and I started because to understand lingerie you have to wear it. Not many people...
    lonelycaleb lonelycaleb 26-30, M 5 Responses Jul 7

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    Today I am wearing a dress to work... Well OK it is a mini dress under my "man" clothing. But how I wish I didn't need to wear the slacks... Also question for you all. I love lace...
    str8CD str8CD 36-40, M 7 Responses Jul 15

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    I can't stop myself from wanting to be a girl sometimes. I do believe I should have been born a girl, I truly feel that because this part of me gets so excited when wearing women's...
    Shadowhunter23 Shadowhunter23 18-21, M 6 Responses Jul 17

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    Reciently I came out of the closet after 30 years of hiding my love for wearing womens clothing. I had told my wife and she is taking it real good, what a trooper she is. This past...
    estacie estacie 51-55, M 12 Responses Jul 21

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    I'm wearing a lovely pair of French Knickers today :) They are purple with a pink waistband going round them. They feel wonderful and so sexy
    LisaTG LisaTG 26-30, T 2 days ago

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    I brought my first bra and suspenders set yesterday along with a sports bra and a Calvin cline top, and a pair of size 8 woman's jeans that are probably a size too small, I love...
    Incideofme Incideofme 36-40, M 8 Responses 2 days ago

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    I just bought five pairs of sexy panties for myself. Seriously, I'm not sure what compelled me to do it. While there have been times in my past when I was in my 20s that I did...
    frogchop frogchop 46-50, M 6 Responses Jul 2

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    Lace is the best. When a guy notices that you're wearing sexy panties. 👍
    orangecrayons orangecrayons 18-21, F 10 Responses Jul 7

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    My wife would put small hoop sleeper earrings on me after I had fallen asleep, for several weeks I awoke and found them, One morning I noticed red dots on my ears and assumed I...
    CdKimmi CdKimmi 61-65, M 2 Responses Jul 8

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    I have been wearing exclusively panties now for 2 weeks. It feels so amazing. So liberating. I am going shopping tomorrow with my girlfriend to VS to pick out a few more items to...
    Winesissy Winesissy 46-50, M 9 Responses Jul 10

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    There's just something that gives you such a confidence boost wearing sexy underwear!! Just need to work on my body so that I look good :) I hate my body so much :(
    Sinead432 Sinead432 18-21, F 6 Responses Jul 18

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    I don't know why. It's probably cause I'm just used to buying that brand. Plus it's convenient when you want to dance, in my opinion. Damn if there was a possibility That I would...
    FunnyandNerdy FunnyandNerdy 16-17, F 1 Response Jul 20

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     Look at this picture. I'm not afraid to show skin. I'm the one wearing the crop top if that wasn't obvious.
    teenally teenally 13-15, F 1 Response Jul 23

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    Almost all of my female attire is second hand! I go to Garage sales a great deal. I have purchased; second hand panties, bras, slips, pantyhose, skirts, blouses dresses, and...
    OhioSissy OhioSissy 51-55, M 2 Responses Jul 23