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

Personal Stories, Advice, and Support 800 People

    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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    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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    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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    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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    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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    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 22-25 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 66-70, M 2 Responses Nov 11, 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 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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    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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    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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    Related Experiences

    I always wear underwear under my dress or skirt. Obviously, because I only wear dresses & skirts. I own a total of 19 pairs of underwear (all white, no thongs). 12 cotton, 6 nylon...
    SweetJane45 SweetJane45 41-45, F 11 hrs ago

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    My name is Vicky. I have cerebral palsy. I went to a boarding school near Brighton. I was a pretty girl then. I had long blond hair. I am slim as well as being quite small. I...
    vickybiggs vickybiggs 18-21 1 Response 1 day ago

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    I love wearing short sundresses year round. I do not have any long pants but I do wear shorts and a bikini when out on the town. I do not wear any panties under my dresses ever...
    redheadedfemale redheadedfemale 41-45, F 10 Responses 1 day ago

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    I like to get up in the morning put on a bra for the day then a summer mini sundress. No pantie. it is so sexy feeling.
    serinalynn serinalynn 66-70, M 5 Responses 2 days ago

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    Mistress left me my clothes for the day, a pair of silky sheer nude pantihose, a little black body-con dress and platform sling back pumps. I love wearing so little, and looking so...
    Plugslave Plugslave 31-35 1 Response 4 days ago

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    Why cant my fiancee get over a one night stand I had when we werent even together? He ended, or said he ended, our relationship to reconcile with his wife and I was heartbroken. At...
    Harleygirl65 Harleygirl65 46-50, F 1 Response 4 days ago

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    Not much went down today. Woke up as usual to the sounds of my sisters waking up in the next room. I actually felt decently well-rested. I lolled about before getting ready for the...
    PinkMellow PinkMellow 18-21, F 4 days ago

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    I wear a Rago 821 waist cincher, which helps my back problems and reduces my waist by 2-3 inches.
    d0hhkgh d0hhkgh 66-70, M 4 days ago

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    what can I say , I think sexy panties, should be for guys and girls, I thought years ago that my girlfriend looked so hot in them, and it was such a turn on for me, I decided that...
    pantydaddydale pantydaddydale 36-40, M 5 days ago

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    I love to wear dresses and skirts. A LBD (little black dress) is always good to have handy :) A pleated skirt is also fun to wear to feel feminine and flips up nicely when dancing...
    satnlacy satnlacy 22-25, T 7 Responses 5 days ago

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    It seems like there are a lot of girls out there who don't like being girls and would rather be boys. Some people call these girls "tomboys". I have never understood why so many...
    danielle1357 danielle1357 13-15, F 1 Response 5 days ago

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    I see you like the same kind of outfits too. Dark colored knee-high socks, long-sleeve shirts, white bra, white panties. I'm from Nebraska, I live on a farm, when I'm out there...
    deleted deleted 26-30 4 Responses 5 days ago

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    Like me, you only wear dresses and skirts too.
    deleted deleted 26-30 2 Responses 5 days ago

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    My parents (actually my mom because I don't talk to my dad so much) say that they love my sister and I equally but they don't. It's clear to me that my mom likes my sister more...
    sk761921 sk761921 22-25, F 6 days ago

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    Call me old-fashion, crazy, or just my southern upbringing, but I still much prefer a dress to jeans and shorts. Dresses to church on Sunday are a must and I love a good summer...
    southernbellegirl southernbellegirl 36-40, F 14 Responses a week ago

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    Who can tell me whatd they make me wear
    jman0105 jman0105 13-15, M 2 Responses a week ago

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    How should I respond to my boyfriends mom? Here is the story of what is going on. My boyfriend has learning disabilities(reading,writing,) but he can function. He can hold a...
    AtadbitLost AtadbitLost 22-25, F a week ago

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    I love wearing dresses or sundresses or skirts and blouses when I am getting dressed up and going out. I always wear hose and high heels with my dress or skirt.
    redheadedfemale redheadedfemale 41-45, F 7 Responses a week ago

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    I am a 15 year old girlyboy who secretly wears his 18 year old sisters lingerie gowns bikini bras panties skirts shirts leggings and make up and I'm attracted to tough men it's all...
    deleted deleted 26-30 a week ago

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    I am a 15 year old girlyboy who secretly wears his 18 year old sisters lingerie gowns bikini bras panties skirts shirts leggings and make up and I'm attracted to tough men it's all...
    deleted deleted 26-30 a week ago

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    I'm a sales rep. at Macy's. The one thing I like is I can wear a dress everyday. I always wear a black dress with a black shirt, black polo short sleeve in the summer a long sleeve...
    deleted deleted 26-30 2 Responses Aug 20

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    Started waist training with a women's corset and holy smokes! After a week and a half the results are undeniable! I've got a real hour glass thing going on here, lol!
    AbsintheMinded08 AbsintheMinded08 26-30 Aug 19

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    The Babysitter Murders Chapter Forty-Six Although I liked Ellen immensely, it was a relief to know Mommy trusted me enough to go with her and my brother and sister shopping. I...
    MaryJanine MaryJanine 56-60, F Aug 18

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    I don't know why but one day like 5 years ago I started stealing my sister's and step mother's clothes and I kept them for a couple months and they found out then they gave me some...
    te214696 te214696 16-17, M 4 Responses Aug 16

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    I've posted this already. I'm serious that I only wear dresses & skirts 7 days a week. It works for this 45 year old Montana girl. I have never wore a pair of pants a day in my...
    deleted deleted 26-30 6 Responses Aug 16

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    I am a 15 year old sissy boy who wears his 18 year old sisters panties bra lingerie and dresses and tights and gowns and make ups secretly and Im attracted to tough guys lol...
    deleted deleted 26-30 2 Responses Aug 16

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    I really like to wear dresses and I am definitely what people would call a dress and pantyhose type of girl. School starts for me this week and I plan on wearing a dress every day...
    allisonhashope allisonhashope 13-15, F 2 Responses Aug 16

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