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I Summer Skirts For Boys

Personal Stories, Advice, and Support 277 People

    Skirts In Summer

    During Junior High and HS I was alone most all days during summer with my Mom and Dad at work. Over a period of time I had amassed a selection of skirts, stealing form clothes lines and my girl cousins. As soon as Mom and Dad left for the day I was in panties and skirts. I kept...
    billbb billbb 51-55, M 4 Responses Oct 31, 2012

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    I once heard of a boy

    who wore a skirt to school. He was in trouble at school but good luck to him. We have to wear skirts except if it is very cold.
    deleted deleted 26-30 1 Response Apr 23, 2015

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    Skirt Me For Summer

    In the no off limits spirit, I'm going to type a short piece here . I was the dressed as a boy who really hated having to wear dark thick t shirts and especially trousers during the summer months so much so that I'd of given anything for a girl to have tied me to a tree to...
    deleted deleted 26-30 5 Responses Sep 20, 2012

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    Ok. I don't mind if boys wear summer skirts.

    Good luck to them! I like summer skirts because they are so cool. I am wearing one tonight.
    deleted deleted 26-30 2 Responses Apr 23, 2015

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    Related Experiences

    Had one that wore short skirts and short shorts very hot!
    floater170 floater170 31-35, M 5 hrs ago

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    I really do feel jealous when I see other boys my age whose chests are clearly visible under their shirts. Because when I look down at my own chest, all I see is my shirt hanging...
    2tail 2tail 13-15, M 8 hrs ago

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    Why is it that your car has to brake down on the day that your wearing a skirt and heels cause your off for an interview and you've to stand on the hard shoulder for 40 minutes...
    melreev123 melreev123 18-21, F 6 Responses 13 hrs ago

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    Planning for vacation has put me into full blown cabin fever mode.   While this is far from the worst winter we've had ... I am so ready for warmer weather.  I want to...
    4EverMan 4EverMan 51-55, M 18 hrs ago

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    I'm feminine enough to like lace and silk, but tomboyish enough not to worry about strangers seeing my panties, so short skirts are a must in my wardrobe.I have long legs, as I'm...
    Wishart95 Wishart95 18-21, F 1 Response 19 hrs ago

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    Summer is near in the Philippines. Me and my friends are planning to have a blast this time again! Come and visit Philippines. You will surely love it here. Especially Summer! :)
    cjg1289 cjg1289 26-30, M 2 days ago

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    And though I know it would never actually happen, I would not be averse to society demanding and requiring that ALL women and girls wear dresses and skirts all the time and banning...
    MrsAshleyR MrsAshleyR 18-21, F 3 Responses 5 days ago

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    I have a really difficult time trusting boys because when I was younger I was beaten up by them at school. I never did anything to deserve that kind of treatment but the boys at my...
    wendiemyers46 wendiemyers46 13-15, F 2 Responses 5 days ago

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    I have a real love for boys dressed as girls. A turn on for sure.
    katythekat katythekat 51-55, F 18 Responses 6 days ago

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    Yesterday was a good day for me and a bad one too. Good day: I invited my daughters over for a taco dinner night. Just a time to be with them and converse. Had a great meal and...
    shadowplt shadowplt 51-55, T 5 Responses 6 days ago

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    I'm a 15 year old sissyboy who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels...
    sissyboyteen sissyboyteen 13-15, M 6 days ago

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    Not going to lie I have an amazing bubble butt... And wearing mini skirts tucked with a g string is so hot!
    Livelife29 Livelife29 22-25, M 2 Responses a week ago

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    I prefer skirts to trousers for pretty much any occasion. when I do wear pants they tend to be women's and other than jeans have a side or rear zipper.
    MyFeminineSide MyFeminineSide 41-45 a week ago

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    Ahh, freedom. So much more comfortable. In the winter when its quite cold I wear them with tights or hose. In the summer oil up my legs and go. Of course, I like short shorts...
    onefourfun4u onefourfun4u 61-65, M 3 Responses a week ago

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    If you seriously support petticoating contact me. I work with mothers who happily use petticoating to turn their bratty sons into proper little ladies.
    radicalfeminist radicalfeminist 31-35, F 5 Responses Jan 31

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    It is strange but I have personally never had a desire to be feminine or a girl as I am a bloke. Though I do respect other men whose views differ. However I do wear skirts at...
    littlegreyshorts littlegreyshorts 51-55, M 4 Responses Jan 31

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    Again this doesn't have to do with skirts, but most of you know me on this post. Just returned from watching a movie, called my soon to be ex and got an ear full of expiration...
    shadowplt shadowplt 51-55, T 4 Responses Jan 30

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    I love wearing my skirts and shoes. of course there is a thong . found some cork clogs at family dollar for 8 bucks. they are cute.
    jpeck1 jpeck1 41-45 Jan 30

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    When I was little, I had some friends whose parents, like mine, were always working, were hardly ever home. Got up early, came home late. One summer, I decided to spend the summer...
    BareFeet199958 BareFeet199958 16-17, M 1 Response Jan 30

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    I got some new items in today. A couple new skirts and new leather boots. This is my faux leather flare skirt I have with my new boots. They fit quite nice. I wonder if I should...
    djshire djshire 31-35, M 4 Responses Jan 29

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    Want to wear a skirt daily in public then go ahead and do it just like I do here in eastern Tennessee every day during the hot humid summer months . I wear a denim skirt at just...
    girdledfarmer girdledfarmer 61-65, M Jan 29

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    WAs in London riding around on the tube. Some very windy days out along the Thames. Lots of close calls with damsels in much distress clutching at their hems .... Was on the steps...
    Marbled45 Marbled45 26-30, M Jan 29

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    5 months now of wearing only skirts to work and everywhere else! This picture is my new Skirtcraft Unaligned Skirt and Wolford Velvet 50 coca tights.
    jeffreyrichards2015 jeffreyrichards2015 56-60, M 3 Responses Jan 29

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    I don't wear panties or a bra when I wear skirts or dresses #FreeTheNipple #Commando
    deleted deleted 26-30 Jan 29

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    Tbh I could die in an American Apparel tennis skirt and I think that would automatically make it a fortunate death. 👍🏻
    spoiledsweetforever spoiledsweetforever 18-21, F 5 Responses Jan 27

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    Look, don't go about life missing If you're alone, that's probably because you haven't been risking 2016 the year I step up my standards If it's one thing I hate is low...
    LeahLovee LeahLovee 70+, F 1 Response Jan 27

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    Ok then. This doesn't have much to do with skirts, but I bit the bullet this evening and had my ears pierced. Should be an eye opener tomorrow at work and when my daughter and wife...
    shadowplt shadowplt 51-55, T 4 Responses Jan 27

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    I really do feel jealous when I see other boys my age whose chests are clearly visible through their shirts, Because when I look down at my own chest, all I see is my shirt loosely...
    2tailkitsune 2tailkitsune 13-15, M 3 Responses Jan 27

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    I love to look up women's dresses and skirts. Yes ladies I am that guy that purposely sits across from you so I can see all your sweet delicious goodies between your legs. I...
    snoop81 snoop81 31-35, M 1 Response Jan 27

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    Be far more comfortable than wearing pants, kilts and skirts are freedom for men
    donontario donontario 61-65, M Jan 26

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    I wear a kilt now fairly often, hoping I can switch to them as my only wear. Skirts would probably better, something mid-thigh for freedom of movement while walking/hiking
    donontario donontario 61-65, M 2 Responses Jan 26

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    When you have nice legs and enjoy showing them off miniskirts or micro skirts and dresses are the greatest thing ever. I wear them all the time, possibly under a longer coat...
    amandatrane1 amandatrane1 51-55, T 3 Responses Jan 25

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    I have discovered this last weekend that I love skirts even more than I thought. I have always worn hose with them in the past. most often thigh highs. However, my girlfriend...
    hosedsailorboy hosedsailorboy 41-45, M 6 Responses Jan 25

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    Why is it that most boys think that the only way they can settle their conflicts is by using their fists? Is it just a macho thing and do they feel that only girls and sissified...
    katiegibson katiegibson 13-15, F 2 Responses Jan 25

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    Ok then....Today was a most illuminating day. I went to work as usual and got done as usual. After work, I had an appointment with a lawyer specializing in divorce. She wasn't...
    shadowplt shadowplt 51-55, T 5 Responses Jan 25

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    I'm glad I found this page. I'm a straight guy who has always had a thing for skirts ever since I was a kid. I do own a few that I bought online. My favorite one is a black faux...
    djshire djshire 31-35, M 4 Responses Jan 25

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