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I Am A Boy Why Cant I Wear Dresses Like My Sister

Personal Stories, Advice, and Support 750 People

    I love crossdressing in private

    and feeling pretty/feminine, but in public I'm an average guy. I'm starting to consider expressing my feminine side in public by wearing more feminine things like skirts/painting my nails etc. but am unsure if I would enjoy this in the long run. I wish there was a way to test it...
    WalterStuart22 WalterStuart22 18-21, M 4 Responses Jan 11

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    Wearing Dresses

    I found out about myself only a few years ago. now I'm wearing dresses or skirts every day. Always had the feeling that I would love and like wearing them. But I only do it at home and around the house, 'cause I still notice that people have problems with this. But I do like it...
    laikagirl laikagirl 51-55, M 2 Responses May 31, 2012

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    Because humans a mentally imprisoned life form

    that needs to be accepted by the norm and any sight of difference is considered a undesirable.
    ValhallaAwaits ValhallaAwaits 18-21, M Jan 11

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    My Sisters' Dresses

    When I was around 9 years old (1961) every Sunday myself & my two older sisters (11 & 14) would go to Sunday School and afterwards we would have our bath. My sisters would bathe first then i would. They would drop their pretty frilly dresses, petticoats and panties on the...
    MsLettle MsLettle 56-60 6 Responses May 20, 2011

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    I Didn't Have A Sister ...

    ... I wish I was one, or that I;d had one, but sadly not ... I always had the urge to dress as a girl as a child, but never had the chance - one reason I take the opportunity now! I wish I was with my 'sister' in a beautiful house, without a single item of male clothing anywhere...
    PrettyPennyM PrettyPennyM 41-45 2 Responses Jul 22, 2011

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    Growing Up

    Growing up I was the oldest and I had 3 little sisters. They were 4, 5 and 7 years younger than me. I always felt that they got better treatment than I did. I remember thinking maybe if I could wear dresses I'd be treated as well. Well I would wear my older sister's dress add my...
    Pegg Pegg 56-60, M 1 Response Jan 10, 2013

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    I like to wear cute frilley dresses

    but its hard i dont want to be hated for it
    drifterx212 drifterx212 18-21, T 4 Responses Mar 10, 2014

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    I Am Straight, But I Like To Wear Dresses~!

    What gives here girls and women both can wear what ever they feel like wearing in the male wardrobe area, and no one blinks an eye!  BUT! If your a male wearing a dress you get stoned to death! Why?
    wjk1849 wjk1849 46-50, M 3 Responses Jan 9, 2013

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    My First Dress.

    My very first dress that I wore was my sisters sparkly tan one. It was long and had straps. And when ever I wear it I feel like I'm a beautiful woman going out to a party. I feel so free in it. It's my favorite dress out of the 4 my sister has. I would wear it outside if my sis...
    Destroyer456 Destroyer456 18-21 3 Responses Apr 6, 2013

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    I've Never Had A Sister!

    but i wish i did because i like to wera dresses skirts slips panties and to be the girl i should have ben born as i still even now wish i were a little girl in cute pretty dresses just to finally be feminine instead of the boy i never wanted to be i wish i were a girl and a...
    eleventhdr eleventhdr 51-55, M 1 Response Sep 29, 2012

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    I Was Caught Wearing Girls Dresses

    My name is Brandon and i love to wear girls clothes but i don't  want to get caught again i was wearing a dress and panties in my back yard and my dad came out to have a segaret and he locked the door so i climbed over the fince and i rang the door bell my dad awnserd and he...
    stacy7 stacy7 13-15 3 Responses Jun 29, 2011

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    Dares #1

    The other day a friend of mine son stop over to see me his friend dared hime to go to a salon and get his hair done if he did $1000.00 would be his .i asked him do you need my help? yes i do .ok ill help first go use the nair i dontwont to see no hairon his body !while he...
    maryyork50 maryyork50 18-21, T 3 Responses Dec 2, 2011

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    How I Dress Now

    I go everywhere!  I wear womens jeans, Womens 2" Sandles, Blouses, Pretty tops, Jewelery, fingernail polish, lipstick, earrings, and I have my hair styled in a fem up-do!  And I shop everywhere, I go with my friend to the V.A., We go dto the Senior Center every day for our $2...
    mlisa7464 mlisa7464 70+, M 2 Responses Nov 11, 2011

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    I Wear Dresses

    There is nothing stopping you from wearing dresses like your sister, I am a 54yr old male & I wear skirts/dresses all the time when I am in doors
    xdpaul xdpaul 56-60, M 1 Response Jun 6, 2011

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    I Was Always Jealous....

    This isn't really a story but...maybe a confession. I was always very jealous of my little sister while growing up in the early 70's.She is 4 years younger, so her clothes would have never fit. Our Mother would dress her in the frilliest holiday dresses with her little mary janes...
    cdsusanri cdsusanri 46-50, T 2 Responses Oct 19, 2011

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    How I Dress Now

    I go everywhere!  I wear womens jeans, Womens 2" Sandles, Blouses, Pretty tops, Jewelery, fingernail polish, lipstick, earrings, and I have my hair styled in a fem up-do!  And I shop everywhere, I go with my friend to the V.A., We go dto the Senior Center every day for our $2...
    mlisa7464 mlisa7464 70+, M 2 Responses Nov 11, 2011

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    Related Experiences

    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 15 Responses Feb 19

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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 8 Responses Feb 24

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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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    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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    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 4 Responses Feb 6

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    I typically wear the right clothes for the right situation, working out, beach wear, etc. But day to day activity in town, at work and about, I only wear dresses and skirts. They...
    freenakedcouple freenakedcouple 26-30, F 7 Responses Feb 21

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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 3 days 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 9 Responses Feb 23

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

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    I have a doctor appt. tomorrow at a female doctor I only see once a year. I am thinking of wearing a dress to the appt. I just bought a new dress and I want to wear it so bad. The...
    mat2Robin43 mat2Robin43 51-55, M 14 Responses 2 days ago

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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 Feb 25

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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 13 Responses Feb 21

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    my daddy brought me home a new dress today I lovvvve it. :D
    Tygersilk1 Tygersilk1 16-17, F 3 Responses Feb 18

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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 6 days ago

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    I wore a dress to a bar message me for the story
    teenslut18 teenslut18 18-21, F 12 Responses 5 days ago

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    Hi! My name is Priyamvad Thenappan. I am 25 year old boy from South India. I am going to narrate my long hair story. I am from orthodox Tamil Brahmin family.I have two elder...
    Longhairmonk Longhairmonk 36-40 Feb 15

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    I can't stand being with my boyfriend any longer, but I don't know if I can leave him...I'm too afraid to let go. So this is our story: We're at a long distance relationship...
    Bitterlove Bitterlove 16-17, F Feb 10

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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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    Last night, Valentine's Day, a group of my friends and I decided to dress up and go see Fifty Shades of Grey. I had told my friend earlier that I was not comfortable wearing...
    hicks15 hicks15 16-17, F 6 Responses Feb 15

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    I would love to be a sissy slave and wear dresses I currently have 43 one piece swimsuits and I would love to be dressed up in girls clothes. Anyone in Australia
    Juzzy91 Juzzy91 22-25, M a week 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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    Im a girl Loving a man who cant Love me back ),: im a chiLdish super friendLy cute Lovely girL uggh im sweet im asking if whats wrong with ME ? why he cant LOVE me Like do why he...
    crazytwentytwo crazytwentytwo 16-17, F 1 Response 1 day ago