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I Boys Protesting Trousers And Shorts By Wearing Dresses

Personal Stories, Advice, and Support 26 People

    I don't think I have to admit I like wearing dresses and skirts! I dream, yearn, desire, and want to wear anything that a woman wears, dresses, skirts, skorts or short-shorts. I'm...
    Cassandrajoan Cassandrajoan 61-65, M 3 Responses Feb 6

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    As I wrote in my first story (found in I Dressing Boys as Girls), sometimes all we know is what others have told us. As you also know, even though I was a boy baby, my mother...
    SylviaJames SylviaJames 56-60 4 Responses Feb 22

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    Yes, its true! I love wearing dresses; short, to my knee's or way above them, or anywhere below my knees. Guess what? I'm a man and I've always felt comfortable and at ease wearing...
    Cassandrajoan Cassandrajoan 61-65, M 1 Response Feb 6

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    Yes, its true! I love wearing dresses; short, to my knee's or way above them, or anywhere below my knees. Guess what? I'm a man and I've always felt comfortable and at ease wearing...
    Cassandrajoan Cassandrajoan 61-65, M 6 Responses Feb 6

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    I finally told someone This is already my 4th story in this group but I have to say thank you to all of you! Your comments on my story encouraged me to tell someone about my...
    ToShareStories ToShareStories 22-25, M 7 Responses 6 days ago

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    My uncle and his new wife got married HATE wearing dresses but wore one How I look? Lol
    RainbowWolf13 RainbowWolf13 13-15, F 1 Response 12 hrs ago

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    Well, i recently split up with my girlfriend and decided no more dressing up so got rid of all my girly clothes. It didn't take long tho until i needed some new underwear...while...
    algina algina 36-40 7 Responses Feb 14

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    I just love wearing short babydolls and fit and flare dresses. It has to be short, it is all about the legs !
    Plugslave Plugslave 31-35 11 Responses Feb 15

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    So today I had my makeover. It was awesome. I tried on lots of outfits, and we chose a blue skater dress with daisies on it, opaque tights, wedge ankle boots with fur trim , and...
    donnaka donnaka 36-40 10 Responses a week ago

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    i'm booked in with a dressing service , for a whole day, in a few weeks. they'll take me out. anyone got any dares for me , while i'm out and trying to pass?
    donnaka donnaka 36-40 2 Responses Feb 11

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    a week from now i'm using a dressing service to go out for a day en femme. i've asked for challenges, had some daft replies, but so far one good one, to try on a dress in a...
    donnaka donnaka 36-40 4 Responses Feb 16

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    I love this dress I wish I had the money to buy it!! How do I look?
    AshleyNicolee AshleyNicolee 18-21, T 12 Responses Feb 21

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    Im not a girl but i would like to try on a dress or two ❤
    sylarisgay sylarisgay 18-21, M 9 Responses 5 days ago

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    I am more than what I wear.
    Brianhi26 Brianhi26 46-50, M 3 Responses 4 days ago

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    Hi ladies! New shoes arrived yesterday! Red pumps that fit well were not expensive and are really comfortable to walk in! Squeee!
    amyjones3371 amyjones3371 51-55, T 3 days ago

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    I had a co worker ask me why I wear dresses and skirts, she actually said to me why are you dressing so girly. I am a woman and I like to wear dresses and skirts, I don't know why...
    Welllaugh Welllaugh 36-40, F 14 Responses Feb 19

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    Where and how does it all begin? At an older age we may not remember possibly the best we can do is to go on what our elders have told us through the years. Thinking back on some...
    SylviaJames SylviaJames 56-60 4 Responses Feb 21

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    I just recently decided that I wanted to start wearing shorts all the time whenever I'm not at work (Can't wear shorts at work). First off, I'd like to mention that I live...
    bigsean88 bigsean88 22-25, M 1 Response Feb 8

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    This is a another childhood memory. One of my favorite movies at that time and still to this day is Hook (starring Robin Williams). Back then, I really focused on a scene towards...
    tightsman88 tightsman88 22-25, M 1 Response Feb 14

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    I like girls as friends but not as girlfriends. I like looking at really cute boys and I imagine that they like me the same way I like them
    wayneS2004 wayneS2004 13-15, M 1 hr ago

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    I started liking dresses when I think the 2nd grade. I was friends with two girls that would always wear fancy party dresses that looked like something for square dancing. I don't...
    Melissa11520 Melissa11520 41-45 2 days ago

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    My bf and I went to the mall yesterday and I couldn't help but notice that I was the only girl out wearing shorts but I saw quite a few guys wearing shorts. What's up with that...
    emdavis emdavis 18-21, F 3 Responses Feb 9

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    Tuesday, March 3, 2015....Today I'm wearing navy blue ribbed Jockey Poco low rise briefs (no fly). The ribbed ones are very comfortable and definitely conform to one's shape better...
    Undieguy Undieguy 36-40, M 2 Responses 2 hrs ago

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    I got a little carried away when I was with a guy last night. I was at a gay party and I let slip that I had tights on under my trousers. Anyway he started to feel between my legs...
    ris9358 ris9358 51-55, M 9 Responses Feb 15

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    I am a 30 year old straight male too and I have started to wear women's short shorts! They feel so much more comfortable with that stretch feel, but also when it hugs around your...
    DiamondD84 DiamondD84 26-30, M 14 hrs ago

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    To Impress : ....and so... we now find ourselves in the 'Tarn' of France. Wearing my normal attire - not trousers (pants) thats 'abnormal' for me, Mini-skirt and tights - I drove...
    dambust3r dambust3r 46-50, M 1 Response 17 hrs ago

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    I felt that even as a straight male I can feel comfortable wearing women's shorty shorts! They just plainly are a heck of a lot more fitting and not even feel that they are on me...
    DiamondD84 DiamondD84 26-30, M 13 hrs ago

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    This arrived and it's perfect. The material is impeccable. The first nice evening of 2015 I'm wearing this. In white of course. I can't wait. I hate cold snow. I'm ready for...
    Jennerrous Jennerrous 36-40, F 10 Responses Feb 9

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    I am 48 and was married 25 years and wore mostly only tee shirts and jeans. After my divorce I lost from size 14 to 8. I straightened my hair and went with high/low lights, added...
    Sharpi1 Sharpi1 46-50, F 7 Responses Feb 15

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    I love short shorts too. If there is no lining even better
    SHORTSHORTS12 SHORTSHORTS12 61-65, M 1 Response Feb 5

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    I have some Jo Snyder shorts. Very daring
    SHORTSHORTS12 SHORTSHORTS12 61-65, M 3 Responses Feb 5

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    I have no choice as my parents always bought shorts and nothing else for me even for winter. But I am OK with that and like to be bare-legged, most of the time the only one like...
    erik2000erik200 erik2000erik200 13-15, M 2 Responses Feb 10

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    I went to visit a friend, 650 km away. My wife bought a velvet suit with shorts just above the knee, wearing with a gray knee-length coat and knee-socks. This was my first bare...
    bareknee bareknee 46-50, M 1 Response Feb 10

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    My mom got pissed at me cuz there was this guy in my kitchen fixing our dishwasher and I didn't know; so I came out with booty shorts ( my *** was kinda hanging out ) and a tank...
    kjonesr kjonesr 18-21, F 7 Responses Feb 22

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    I like wearing short shorts with heels Or flats
    lorrena19 lorrena19 18-21, F 1 Response 3 days ago

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    FOR LADIES ONLY - Wearing pants Is Masculine. Masculinity AND Femininity ARE Opposites. You CANNOT wear pants; and 'Claim' to be Feminine. If you DO, You practice Lies and...
    desireindisguise desireindisguise 56-60 Feb 18

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    So yesterday I impersonated a real person in a uniform I made up from ebay. I bought a hivis jacket with security reflective patches, black security trousers, a white shirt, black...
    Kymmy2012 Kymmy2012 22-25, F Feb 15

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    I am wearing my red shiny lycra shorts under my jeans I love how they look and feel
    wheels1972 wheels1972 41-45, M 3 days ago

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    Today I am wearing black lace and silk boody shorts if I'm not mistaken they're bobby brooks. the the top is the silk and the rest is the lace so they leave very little to the...
    onomaine onomaine 22-25, M 22 hrs ago

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    Wednesday, February 18, 2015....Today I'm wearing a navy blue pair of 2(x)ist Pro Sliq no-show briefs (bikini). They're made of some awesome nylon microfiber and they feel awesome...
    Undieguy Undieguy 36-40, M 2 Responses Feb 18

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    Well close anyway. In my teens, I wore clothes intended for my sister. My mom's best friend had a daughter the same age as my sister but much bigger. Her good used clothes were...
    AlbertSAT AlbertSAT 66-70, M 8 Responses Feb 5

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