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I Summer Skirts For Boys

Personal Stories, Advice, and Support 278 People

    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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    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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    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

    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 2 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 2 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 3 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 4 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 4 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 1 Response 4 days 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 4 days 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 5 days 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 3 Responses 6 days ago

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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 a week ago

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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 a week ago

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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 a week ago

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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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    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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    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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    I like bad boys too but also needs geeks whatever doesn't matter to me
    Yplv Yplv 16-17, F 3 Responses Jan 25

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    simply cannot remember a time when my younger sister (the baby of five siblings) did not express a distinct and vehement desire to dress like a boy. Aged two, she was found...
    janecool janecool 16-17, M 2 Responses Jan 25

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    I am 13 years old and I have to admit that I like boys but I am also very curious about girls and I think about what it would be like to date one. I have kissed a couple of boys...
    rachelholland rachelholland 13-15, F 2 Responses Jan 24

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    Been wearing my Skirts, by gender they are Gentleman's Skirts, for thirty years. No one has time to bother what I wear. I like to look smart or casual. definitely a man in a Skirt...
    kiltiekid kiltiekid 66-70, M 1 Response Jan 24

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    I never use this app anymore I never really write things out either and don't expect anyone to really read this so I guess it's just my way of clearing my head haha. If I think...
    MShein MShein 18-21, M 2 Responses Jan 22

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    I don't know what it is about denim skirts but they drive me crazy! Maybe it's because it's a hard wearing material that is normally associated with jeans, maybe because when I see...
    jameson1992 jameson1992 46-50, M Jan 22

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    I'm a 15 year old sissyboy I secretly wear my 17 year old sisters cloths tank tops bra panties lingerie dresses gowns bikini tights leggings yoga pants skirts and definitely make...
    deleted deleted 26-30 Jan 20

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    I'm a 15 year old sissyboy I secretly wear my 17 year old sisters cloths tank tops bra panties lingerie dresses gowns bikini tights leggings yoga pants skirts and definitely make...
    deleted deleted 26-30 Jan 20

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    Ok, here goes.....It's official, I'm getting divorced. My soon to be ex-wife and I had dinner together last night and discussed our situation. It was a very frank and quite...
    shadowplt shadowplt 51-55, T 12 Responses Jan 20

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