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

Personal Stories, Advice, and Support 755 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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    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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    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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    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 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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    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 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 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 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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    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 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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    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 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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    Related Experiences

    No more dresses for me !? Mistress does not want me to wear dresses any more. She wants to be able to see my lingerie, she does like my leather dress, so I am not without a...
    Plugslave Plugslave 31-35 3 Responses Apr 13

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    Like many of you I really like wearing dresses. My favorite is an a-line bodice with short sleeves and having a full skirt. I cherish the task of having to zip up the back of my...
    deleted deleted 26-30 9 Responses Apr 5

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    I'm a guy but I like to wear dresses they are comfortable and nice tell me what you think
    changegender changegender 16-17, M 1 Response 4 days ago

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    Been a long, long time since i was a 'boy' but I remember how much I loved to play after school with the girls in my neighborhood wearing the play dresses my mom made for me. I was...
    AlbertSAT AlbertSAT 66-70, M 3 Responses Apr 12

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    talk to me anyone who likes wearing cute or sexy dresses ;)
    ilikepugs ilikepugs 13-15, M 2 Responses 3 days ago

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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 6 Responses Mar 29

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    All your sissy's are too much. Girls dont talk about what kind of panties or bra's they are wearing. I think its so funny listening to you all brag about how wonderful it is to...
    jennylee911 jennylee911 41-45, F 4 Responses Apr 9

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    Little girls with long long long hair love to wear 2 ponytails any height with hair bows– and they also love to put little boys long long long hair up in 2 ponytails any height...
    PonyTailsGirl24 PonyTailsGirl24 46-50, F 5 Responses 6 days ago

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    Dresses are my fav, I don't really ever wear pants unless I have to. I like pink or black dresses with poka dots on them or just all pink maybe some flowers to if I'm feeling...
    daddysfavoritegirl daddysfavoritegirl 13-15, F 3 Responses 5 days ago

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    Not always. But sometimes I'd like to dress sexy. Tight short dresses are my favorite, some of them reveal my lingeries. (as you can see below) So I enjoy to see how peoples' react...
    Canaria Canaria 22-25, F 19 Responses Apr 12

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    I love that the weather is getting warmer and I get to see more women wearing skirts and dresses, showing off their beautiful legs. Makes a man's mind rage with questions and...
    avgjoe71 avgjoe71 41-45, M Apr 6

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    so in 2 weeks i'm going out again. i've set myself the following tasks to complete whilst hopefully passing as a woman (i) visiting a particular tourist attraction , and having my...
    donnaka donnaka 36-40 6 Responses Apr 15

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    I LOVE dressess. l'm a little dress obsessed :P
    NightOwlGirl NightOwlGirl 18-21, F 4 Responses Mar 28

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    I'm a 52 year old man and have been crossdressing since I was about 7. I would much rather wear a dress that pants and a belt. Like most men my age I've got a bit of a "belly" and...
    hotgarters hotgarters 46-50, M 5 Responses 23 hrs ago

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    The prettiest dresses are worn to be taken off...
    Brunette4U Brunette4U 31-35, F 5 Responses 6 days ago

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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 Mar 27

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    Samara11besc here I just bought the most cute halter dress black and white zebra stripe exposed shoulders and perfectly my size at a thrift store the hem is solid black and my...
    samara11besc samara11besc 51-55 2 Responses Apr 1

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    I own 2 pairs of pants for extremely cold weather and outside work thsts hard in a long skirt. My skirts least come to midway between my knees and ankles. I was raised to be a...
    sassygirl15 sassygirl15 13-15, F 2 Responses 1 day ago

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    The poor country pastor was livid when he confronted his wife with the receipt for a $250 dress she had bought. "How could you do this!" he exclaimed. "I don't know," she wailed...
    jml2000 jml2000 56-60, M 3 Responses Apr 3

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    My wife loves the fact that I wear full dentures as much as I enjoy wearing them. She finds my 'handicap' appealing, and my gummy smile 'cute'. She is also very keen on my other...
    dendek dendek 41-45, M 2 days ago

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    My then fiancée, now wife, encouraged me to get full dentures. She knew my partials caused me discomfort and, when two further teeth crumbled, and then my wisdom teeth erupted and...
    dendek dendek 41-45, M a week ago

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    today i am very sad day, because i stand for my friend in their happy and sadness.one of my friend said that . "iam the trouble and i make the trouble". its okay for me ,i dont...
    mubariskhan mubariskhan 22-25, M Apr 16

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    today is my off I am enjoying my short skirt at home
    girlyboy83 girlyboy83 31-35, T 6 Responses Apr 3

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    2015 Jovani Sheer Sleeve Sexy Prom Dress 74457 From www.darlingpromgown.com
    Experiencdsds Experiencdsds 26-30, M 1 Response Mar 27

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    Lace Red Short Prom Dress 2015 By Sherri Hill 21227 Hot From www.darlingpromgown.com
    Experiencdsds Experiencdsds 26-30, M 1 Response Mar 31

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    Sequined Purple Strapless Lace-Up Back Ball Gown From www.promgowndiscount.com
    Experiencdsds Experiencdsds 26-30, M 1 Response Mar 31

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