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

Personal Stories, Advice, and Support 757 People

    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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    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 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 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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    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 1 Response Jan 10, 2013

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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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    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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    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 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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    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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    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 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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    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'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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    Related Experiences

    I just loves every single thing about wearing a dress. Girls grow up wearing dresses as a a formality that turns many women off to wearing a dress, but I can't see how anyone would...
    CDcarly CDcarly 22-25, T 2 Responses May 17

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    Do you love wearing dresses and skirts and what color are they do you haveLong or really long hair and do you wear plain or fancy hair clips hair barrettes bobby pins flowers and...
    PonyTailsGirl24 PonyTailsGirl24 46-50, F 7 Responses May 15

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    omg...... I live at home with my brothers and mum and I like wearing my school dress witch I brought online at home and no one knows I sometimes walk out in public wearing it and...
    imcool2002 imcool2002 13-15, M 2 Responses May 9

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    I also wear dresses & skirts, I'm sat in hotel room, wearing red skirt, stockings and panties. Tomorrow I intend going into town and buying a LBD.
    simonsteane simonsteane 46-50, M 3 Responses May 17

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    I do like wearing dresses but also shorts now that it's so warm out. Next it's the beach.
    jusleaving jusleaving 18-21, F 2 Responses May 12

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    Why does it feel like everyone in my family hates me my parents always seem to favour my brothers and my sister but never me I'm starting to fill unwanted because everyday I always...
    Icryeverytime Icryeverytime 13-15, M 4 days ago

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    So tomorrow was going to be a day out with a dressing service. and like a small child at Christmas , i was counting the sleeps till it happened . And wot? Today I get a message...
    donnaka donnaka 36-40 8 Responses Apr 27

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    If anyone want to give me advice I want to start dressing like a girl
    deleted deleted 26-30 4 Responses May 5

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    None of them fit me properly and when I go shopping for dresses it makes me feel terrible about the way I look.
    23fly41 23fly41 16-17, F 1 Response 6 days ago

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    I wear wife's legging bra panty and top.. I ride a bike.. My wife also help me to wear those cloths..now i m wore it.
    rohitsomalkar rohitsomalkar 31-35, M 1 day ago

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    I do. Call it old fashioned. Or girly. Or a desire to be just a little sexy, but I like wearing them. I am so glad spring is here!
    pinkcorsetgirl pinkcorsetgirl 41-45, F 17 Responses Apr 30

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    Oh yes... Do I love my dress. I wear them all year long. Short and some long. It is nothing like getting up in the morning taking a shower. Blow drying my hair and then putting on...
    Babeondwy Babeondwy 41-45, F 3 Responses May 2

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    My first time wearing a dress was when I was 14. I put on a black dress with stockings. I knew then I was different and had a female side. I enjoyed more and more as I started...
    bmg1kel bmg1kel 61-65, T 3 Responses 6 days ago

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    Listen up! Ladies I just brought 2 of the cutest doll dress you ever want to see. 1st choice one has multi colors coral, pale blue black and a tab bit of white. I have a coral...
    Babeondwy Babeondwy 41-45, F 2 Responses May 2

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    jst bought a cute red dress today :) :) so excited to wear it :)
    littlejoey4190 littlejoey4190 22-25, T 5 Responses May 3

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    So I made myself pretty , and went to the library:- new photos , friends only.
    donnaka donnaka 36-40 1 Response Apr 29

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    for those of you who have noticed I've been asking for cross-dressing challenges, today(i) had coffee and a ciabatta in a cafe(ii) then went to a ticket office , where the "thing...
    donnaka donnaka 36-40 14 Responses May 6

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    Just some more new stuff, love my new clothes, I need more clothes and sone make up also a wig
    ArejayakaRegina ArejayakaRegina 22-25 6 Responses May 18

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    I have never done it before, but I really want to try. **** gender roles! Clothes have no gender!
    Madobsession Madobsession 16-17, M 1 Response 1 day ago

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    Look at my dress 😍😍😍...I'm sorry but when it comes to a cute dress. I will buy it no matter how short it is.
    ANNI3PI3 ANNI3PI3 16-17, F 10 Responses May 8

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    I don't think many are open minded. Sometimes I just want to give it all up. It gets so tiring fighting the pregudices
    beyerswede beyerswede 61-65, M 11 Responses May 16

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    The second my house is empty I put on my gaff, then some sexy lingerie and a dress. I'm at my happiest when I'm walking around in a tight sexy dress. X
    HaileyPenny HaileyPenny 18-21, M 4 Responses 6 days ago

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    I love skirts but the have to at least be to my knees
    Selinajudge Selinajudge 18-21, F 6 Responses 2 days ago

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    Timmy Timms is a 8 year old boy who is small for his age with blond hair in a very 1950's short back and sides with a face and he has dimples and big blue eyes. Tim has a problem...
    paddyboy1961 paddyboy1961 46-50, M 1 Response 17 hrs ago

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    I have been wearing thong casually for 3 years now. My first experience with thongs came from my sister and her best friend. They both were experiencing transitioning into become...
    krzlaoboi krzlaoboi 22-25, M 5 Responses May 5

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    So ,growing up I had 5 sisters. I was the only boy and my parents work in the military. I was 12 years old and my oldest sister was 22 my second oldest sister was 19 then 17, 14...
    Loserbame Loserbame 26-30, M 6 days ago

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    Part 3 Recap from part 2 I got all girl clothes and school uniform Now it was the first day back after breaking I come in looking like this Image from http://img1.promgirl...
    Sexyrachel1406 Sexyrachel1406 18-21, M 1 Response 4 days ago

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