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

Personal Stories, Advice, and Support 700 People

    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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    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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    Please, Can I

    I have always wanted to dress like my sisters. I wanted to wear those pretty little dresses and sunsuits that they got to wear. The one with the ruffled sleeves and hems as they brushed your arms and legs. I could not wear them as my sisters were younger than me. Believe me I...
    Adam59 Adam59 56-60, M 3 Responses Mar 1, 2013

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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 6 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 70+, M 2 Responses Nov 11, 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 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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    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'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 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 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 7 Responses May 20, 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 51-55, M 1 Response Jan 10, 2013

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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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    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 4 Responses Dec 2, 2011

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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 5 Responses Mar 10

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    Related Experiences

    I wish i could wear dresses and skirts 24/7. I want to wake up in a nighty every morning. Finish my morning rutines then change to a short dress/skirt and slip in to some nice...
    sissypantyhosekiss sissypantyhosekiss 18-21, T 16 Responses Jun 24

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    I wish I could wear dresses twenty four hours a day. I have started a small collection of them an am buying more as I can. I will most likely never have enough of them.
    Jessica1967 Jessica1967 41-45, T 7 Responses Jul 10

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    Even though I'm quite masculine looking, I love wearing dresses and skirts. I only wish I had been allowed to do so as a child.
    quearme quearme 56-60, M 3 Responses a week ago

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    I am a business man I am merried my wife is also know about my hobby of wearing female dresses i like to wear saree blouse much. i have few collection of saree blouse bra paticoats...
    surekha57rpandya surekha57rpandya 56-60, M 3 Responses Jul 10

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    i love to wear my mothers and sisters clothes now i feel better wearing them than i do my own but what happens if i get caught
    glovesam glovesam 26-30, M 5 Responses 2 days ago

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    So I love dressing up in my/and my wifes dresses. I love trying on her dresses. Wished I could do it with her knowing I would love to be fully out of the closet, I hate having to...
    Laurie1960 Laurie1960 51-55 7 Responses Jul 14

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    I love crisp tailored clothes- I try to wear nice jackets, pencil skirts or shift dresses for work. Usually in neutral colors like white, black gray or navy. Sometimes I might...
    theyrereal theyrereal 31-35, F 4 Responses Jun 25

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    I wear female clothes except at school.even when going out, I prefer dressed as girl, than as a boy with long hair.
    charudays charudays 18-21, M 3 Responses Jun 29

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    When I started cross dressing it was a winter thing, but now own so many summer dresses short and long......
    amber8642 amber8642 51-55 3 Responses Jun 29

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    I'm a jeans-and-T-shirt kind of girl, but I just love dresses. My dream is to find the perfect dress to wear with Chucks.
    cece930 cece930 18-21, F Jun 25

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    I love my Leather and PVC skirts and Dresses, it make me feel so sexy.......
    amber8642 amber8642 51-55 3 Responses Jun 29

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    I love shirts and dresses. There just awesome. I mainly posted this so I could get opinion from people with fashion lol Pink skater skirt or Aztec skirt?
    LovelyDeadly LovelyDeadly 16-17, F 6 Responses 2 days ago

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    i wear my mums clothes and it feels good anybody else do it
    glovesam glovesam 26-30, M 6 Responses Jul 5

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    I just took a good look at my favorite house dress, and realized I'll have to replace it. It is threadbare! I like it so much that I've worn it out. It is a yellow cotton...
    aprilrose aprilrose 61-65, T 4 Responses Jun 26

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    I woke up yesterday and went to help my wife make her lunch. I had on the blue floral nightie I had slept in. When my wife left for work I went and toke a quick shower and then put...
    mat2Robin43 mat2Robin43 51-55, M 4 Responses Jul 8

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    But I respect those people who are gay.
    schoolgyrlKaren schoolgyrlKaren 41-45 5 Responses Jun 23

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    Yeah guys sorry , (I'm not really)
    swagstagram100 swagstagram100 16-17, F 4 Responses Jun 30

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    I'm going to dress up sexy and walk around at Milford lake park
    harley80cu harley80cu 41-45, M 1 Response Jul 14

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    Check out this maker of skirts for men. http://www.skirtcraft.com
    Prettyjennifer2004 Prettyjennifer2004 51-55, M 2 Responses a week ago

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    Last weekend I wore a skirt everywhere I went and it was a lot of fun and I really enjoyed myself and so did my fiancé. We both had a lot of fun with it and going to do it again...
    highkin highkin 31-35, M 6 Responses 3 days ago

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    I bought 2 today. And shoes. Did I need them? Not a bit. But I always feel prettier in a dress.
    pinkcorsetgirl pinkcorsetgirl 41-45, F 2 Responses Jun 28

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    I gave you my heart, all my love, my life, you are my all, only and everything why cant you see this hurts, why? I love you so much without you I would instantly die I swear I...
    CallmeShaneyney CallmeShaneyney 13-15, F 20 hrs ago

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    When I say annoying, I mean that she says and does things that makes me think "wtf? you really think thats funny?" or or "why would you even say/do that?" Shes a good sister, she...
    JosephMichaelSmith JosephMichaelSmith 18-21, M Jul 10

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    Me and my boyfriend have known eachother for years. We have been dating for 2. A few months ago we signed a lease and moved to a new town. A week after moving in together we get...
    angrynhyrt angrynhyrt 31-35, F 1 Response 2 days ago

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    Dont know why, i just feel like writing and writing, sorry if i annoy u
    desirejanice desirejanice 22-25, F 1 Response 21 hrs ago

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    Sooo I have a boyfriend who doesn't realize that his words and actions don't match up. He is one of those talk the talk but can never walk the walk kind of boys. I feel like he...
    SilentNynja SilentNynja 22-25, F 1 Response 12 hrs ago

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    he makes me feel so special sometimes like he would do anything for me but then he gets me off guard and hurts me a lot and he doesnt care, i told him that i cutted and he just...
    CallmeShaneyney CallmeShaneyney 13-15, F Jun 29

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    I wish there was a guy that could sweep me off my feet. I hate being single and looking at couples walking besides me. The other day I was sitting down thinking to myself: why cant...
    WeirdOtaku WeirdOtaku 18-21, M 2 Responses Jul 10

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    I always try to be matching. Well Monday to Friday evening i only wear knickers (different styles of course) and no bra as i don't want people in work to see the bra under my t...
    Madhead79 Madhead79 31-35, M 2 Responses Jul 13

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    I love wearing dresses, but changing into sweat pants and a hoodie is so much more comfortable! 😍
    TheSongPlaysWithin TheSongPlaysWithin 16-17, F 2 Responses Jun 25

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    More like a woman. I like wearing dresses and skirts, pretty Lacey underwear and bras. I like curling my hair and smelling good. I like baking and helping people. There is...
    theyrereal theyrereal 31-35, F 7 Responses Jun 24

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    Like, everything is crap. Worthless ****. Nothing.. And that I can go on no more. But i been there, and I dont want to go there again. I read many books over my time now... Much...
    mirkwood86 mirkwood86 26-30, M Jul 11

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    My female friends are sometimes mistaken for being actual girlfriends and i can see why. I treat them like my trophies, my prize possessions my Princesses. Its like being my...
    coolcalv coolcalv 26-30, M 3 hrs ago

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