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

Personal Stories, Advice, and Support 777 People

    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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    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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    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 66-70, M 2 Responses Nov 11, 2011

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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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    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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    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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    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 22-25, M Jan 11

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    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 5 Responses Jan 11

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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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    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 66-70, M 2 Responses Nov 11, 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...
    57Peggy 57Peggy 56-60, M 2 Responses Jan 10, 2013

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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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    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 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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    Related Experiences

    why does somebody have to be born looking pretty good(im not saying im the hottest thing out there) and not have any social skills... The last girl i was with thought i was as...
    sip3065 sip3065 22-25, M 1 Response 1 hr ago

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    They are just so cute :) even cuter than the girls in the dresses!
    MilkyCowCow MilkyCowCow 18-21, F 5 Responses 3 hrs ago

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    when I was 7, I was lying on the ground when my friend josie sat on top of me. We played a game she was interogating me. She was wearing yoga pants. Later on we played the same...
    jasondil jasondil 26-30 4 hrs ago

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    So I desperately need feedback to see if I'm the crazy one. I've been dating my boyfriend for two years. His one sister and I were fairly close at one point, but she was always...
    imacanceryo imacanceryo 22-25, F 6 hrs ago

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    I had to because I had outgrown all of my own underwear and mum said I had to wear my sisters cast off underwear as she could not afford to keep buying them as I was growing so...
    homesparky homesparky 46-50, M 2 Responses 9 hrs ago

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    One day I got one, as if by some miracle, and it was around Christmas time, which made it extra special. I didn't know that she had been searching for me because I wasn't ever...
    salty2013 salty2013 31-35, F 1 Response 9 hrs ago

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    I wore these shoes when I went out last Saturday.
    prudance prudance 51-55, T 9 Responses 10 hrs ago

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    This is me last Saturday before I went out.
    prudance prudance 51-55, T 4 Responses 14 hrs ago

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    I hardly ever wear it unless I'm going to work, church or a special occasion. I'm not knocking women who wear it faithfully; but I've never been that girl. I didn't even start...
    beyondrepair321 beyondrepair321 22-25, F 5 Responses 15 hrs ago

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    I enjoy wearing women's skirts and dresses privately. I have no shame in doing it. It feels so wonderful and outstanding. If society would accept this type of behavior I would it...
    12rak38 12rak38 36-40, M 5 Responses 17 hrs ago

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    Any girls wear leather mini dresses
    luke6615 luke6615 18-21, M 18 hrs ago

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    Bridesmaids are always close friends, cousins or sisters of the bride, and they wear beautiful dresses and hold nosegays in their hands to attend the bride's big day and complement...
    flywishes flywishes 26-30, F 19 hrs ago

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    I love wearing underwear, especially when they're under my dress. And again, I only wear dresses. Most of mine are white and no thongs. That is the only clothing I put on one leg...
    JamieCarlin44 JamieCarlin44 41-45, F 3 Responses 1 day ago

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    When using one of those dating apps where you swipe and swipe pictures, 80% or more has this icy look. I am not even sure if id call it a serious look, it is just kinda flat, icy...
    mirkwood86 mirkwood86 26-30, M 1 day ago

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    It seems frustrating...whoever i meet now is like am looking at a piece of wood..no feelings at all..i keep trying to overlook the matter and see the soul but in vain
    kimoboston kimoboston 36-40, M 1 day ago

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    I would love to wear old fashioned dresses everyday. I might as well, I have never wore pants or shorts of any kind. I'm almost 45, I'm a plus size, I never have wore pants, shorts...
    JamieCarlin44 JamieCarlin44 41-45, F 1 day ago

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    22 year old single woman looking for women older than my age to cuddle and be intimate with. I enjoy being nurtured and taken care of. Maybe a future wife may come along, but am...
    RainbowsAndMangos RainbowsAndMangos 22-25, F 2 days ago

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    I would like you to share your opinion on this matter. I am single mom with two children and I think I have a good body for a woman at my age, that's why I wear a thong swimsuit...
    Kimberley811 Kimberley811 31-35, F 4 Responses 3 days ago

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    I really believe all boys should experience wearing a dress, A feeling comes over you that is incredible, you are happy and friendly, wanting to make others the same.
    CharleeneA CharleeneA 13-15, M 4 days ago

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    One would find me in either a short skirt and blouse or a short dress when I am out. I do not wear pants to work because I feel it is unprofessional for me to do so. Besides I am...
    femalemusiclover femalemusiclover 46-50, F 9 Responses 5 days ago

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    zip up the back is very nice to have it must feel so sexy if you are with someone and you can feel them slowly unzipping your dress and just slide off that has to be sexy
    dresscross dresscross 51-55, M 6 days ago

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    Pot is ok but I hate people that must tell me they smoke it or talk about how they do it. Who cares? I take a **** but I don't get on Twitter and brag about it. Smoke it, ok great...
    iSceneGirl iSceneGirl 13-15, F 4 Responses 6 days ago

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    It's Summertime!!! That means SUNDRESSES!!! Yay!
    Mrskatearch Mrskatearch 31-35, F 13 Responses a week ago

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    Terror on Extension 29 Nineteen - Michael Duke I didn't sleep that night after my wife and daughter called me back to report their findings. My theories had been blown right out...
    MaryJanine MaryJanine 56-60, F Jun 24

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    I'm a boy that likes putting on my sisters makeup 💄 bra panties and high heels 👡 lipstick 💄 dresses skirts
    tmccom123450 tmccom123450 13-15, M 1 Response Jun 22

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    ya I too love to be a women and wearind skirt and I have some of them..but right now I am wearing a red saree..and I feel feminine and sexy
    deleted deleted 26-30 Jun 21

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    I am a white girl and I've been absolutely fascinated with black boys since I was about 9 or 10 years old. I always used to wear dresses and white pantyhose to school in 4th and...
    ashlynparker2001 ashlynparker2001 13-15, F Jun 21

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