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

Personal Stories, Advice, and Support 751 People

    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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    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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    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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    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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    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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    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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    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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    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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    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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    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 66-70, M 2 Responses Nov 11, 2011

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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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    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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    Related Experiences

    Dresses and skirts are the best i believe all girls and women should wear them. I wear dresses and skirts that hide my knees i was raised to the fact that girls must not show too...
    sweetmary14 sweetmary14 13-15, F 1 Response a week 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 6 Responses Mar 2

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    So tonight my parents went out of town so it was a total girls night for me. I've been trying to wear panties everyday for about a week now, so today I was already in my cute...
    CDcarly CDcarly 22-25, M 1 Response 4 hrs ago

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    Not for religious reasons (I’m agnostic) or laziness but for the freedom it seems to give me. I like walking around in my yard, sitting on the porch (I mean on solid ground not a...
    DreamCloud17 DreamCloud17 18-21, F Mar 14

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    i am cross dresser man i like wear saree blouse . my close friend knows my this hobby one day he challenge me to pass in public as lady. At that time i have no time for make up on...
    surekha57rpandya surekha57rpandya 56-60, M 2 Responses Mar 16

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    send me pics of boys in dress or girl clothes or if they are Male to Female any age under 18
    raileymathins raileymathins 18-21, T 4 Responses Mar 17

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    I have worn dresses since I was quite little and I still do. I love how they make me feel. Today is a dress day rather than skirts. My dress is royal blue ,knee length and has...
    paula3198 paula3198 46-50, F 2 Responses Mar 8

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    the most amazing thing is a woman dressed in heels hose and skirt and acting like a woman but that isnt nothing compared to shaving your legs lotion up and paint your toenails then...
    samara11besc samara11besc 51-55 7 Responses 5 days ago

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    I LOVE dressess. l'm a little dress obsessed :P
    NightOwlGirl NightOwlGirl 18-21, F 3 Responses 12 hrs 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 20 Responses Mar 3

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    If I could wear a dress everyday, that would be heavenly! I remember a time where you would never catch me wearing a dress... That changed in college. Now I'm proud of my legs and...
    SeanaO SeanaO 18-21, F 5 Responses Mar 19

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    I like wearing a beautiful dress with some heels. It makes me feel like a pretty lady.
    xBeatifulDollx xBeatifulDollx 18-21, F 5 Responses Mar 8

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    Just been out for a lovely meal on holiday wearing a dress and heels that cost next to nothing and lots of people wanted to know which designer shop I bought my dress in I haven't...
    girlynicole girlynicole 36-40, F 1 Response 1 day ago

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    except me for my ways and i will be loving and true i just feel the need for love and give it. i love being happy to be a loving and caring b boy
    tomot2121 tomot2121 51-55, M Mar 16

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    I love to experiment with different outfits. This is my black/white mod dress with white tights and my favorite Mary Janes!  See more in my album.
    sensuousPH sensuousPH 41-45, M 17 Responses Mar 17

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    Went to Sears today and I tried on this dress cause I thought that it looked really cute what do you all think? Please ignore the socks
    highkin highkin 36-40, M 11 Responses 4 days ago

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    I do and wish I could more often
    shannonsjourney shannonsjourney 18-21, F 1 Response Mar 18

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    At the weekend I am going to a costume party. Of course I am dressing as a woman in a pink dress as in the cover picture. I will have to walk in public to get there as it is not...
    Prettyjennifer2004 Prettyjennifer2004 51-55, M 8 Responses Mar 18

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    2015 Jovani Sheer Sleeve Sexy Prom Dress 74457 From www.darlingpromgown.com
    Experiencdsds Experiencdsds 26-30, M 1 Response 1 day ago

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    I am a 14 year old white girl and I am very feminine in the way I dress and conduct myself. I wear dresses or skirts with white pantyhose to school every day and I am very much...
    weakandpowerless weakandpowerless 13-15, F 3 Responses Mar 17

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    I've only met 2 people like that. we all used to be best friends. Like sisters, actually. we were all so similar, that we could've passed as triplets.. But without actually looking...
    Scoodaloop Scoodaloop 18-21, F 16 hrs ago

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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 Mar 5

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    I want to find a girl that can love me an dominate me force me to wear dresses and spank me and all that stuff....... I don't think any girls would be willing in a million years to...
    lovepink73 lovepink73 16-17, T a week ago

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    LIKE SEROUS, I CHATTED TO MANY GURLS ON LINE, EVERY ONE SAY YES I LIKE TO CHAT, BUT THY CANT KEEP A DAM CONVERSATION GOING, OR THE LIKE YAH LETS CHAT AND U NEVER HEAR FROM THEM...
    PAL15 PAL15 26-30, M Mar 6

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    I'm a girl and I love to wear only thongs and g strings is it all I wear I don't like normal panties my boyfriend loves I wear thongs everytime I go to the mall I walk out with...
    sexyness1987 sexyness1987 26-30, F 2 Responses Mar 3

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    i dont know what to do anymore everything feels like its not normal not rite nothing is normal no more everything is jest not the same i cant stand it why do i feel like this i...
    emoteman emoteman 18-21, M Mar 9

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    Hiya. It's Kelly. This is my first posting in about 3 months ( I had a break from EP) and it's something I wanted to share. If you've read my other stories you'll know that for a...
    kellyloveslife kellyloveslife 18-21, F 5 Responses Mar 16

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