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

Personal Stories, Advice, and Support 732 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 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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    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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    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 5 Responses Mar 10

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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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    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 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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    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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    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'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 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 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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    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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    Related Experiences

    I first started experimenting with wearing dresses when I was about 6 years old.at first I wasn't sure why I did it fight at the time I enjoyed the experience. When I got older...
    Dora922 Dora922 31-35, T Oct 16

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    Why not?? They are the best clothes and boys don't wear them because they're embarrassed? I say man up and wear them and love them.
    MissAlanah MissAlanah 18-21, F 11 Responses Oct 17

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    I first started experimenting when I was 6 years old with wearing female clothing. As I reach puberty I started experimenting more with bras and panties and occasionally address...
    Dora922 Dora922 31-35, T 12 Responses Oct 16

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    I love wearing my skirt and tights when im at home my wife son daughters and soninlaw all know that I wear them it's just normal for them to see me wearing skirts and tights
    step1968 step1968 46-50, M 4 Responses 3 hrs ago

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    I would like to know how many girls, not guys in skirts, but girls who like to wear skirts, if they still wear slips. It is harder and harder to find really pretty slips in the...
    sharonwoods sharonwoods 51-55, M 1 Response 1 hr ago

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    Hi I am lee about 2 years ago I started wearing my sisters dresses now I love being in them and want to tell my mom
    YngLee YngLee 13-15, M 2 Responses Oct 6

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    Not all boys necessarily , but in general, I think boys should be able to wear skirts and dresses and have it be fine. Girls wear pantsuits and they're perceived as powerful. Boys...
    laracomn laracomn 16-17, F 19 Responses Oct 18

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    When I was younger I used to steal my older sisters' clothes one was ten years older the other six years older than me. Until I was caught and got the belt and made ashamed by my...
    Hiddensissy69 Hiddensissy69 26-30, M 5 Responses Oct 1

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    I just had to pull off the road and write about my experience. I went to my sister's house to pick up some things. As I left her house, while still in the driveway with the motion...
    Sharon03 Sharon03 56-60 4 Responses 3 days ago

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    I started wearing skirts and dresses since I was14 years old. I would pick them out of my moms closet and wear them for some hours. Me personally always liked the blach gothic...
    ChanelleCD ChanelleCD 18-21, T 4 Responses Oct 12

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    My friend took me dress shopping this morning , it was the happiest I've been in a long time. I got to twirl and try on several dresses. I picked out an awesome blue dress that's...
    Hiddensissy69 Hiddensissy69 26-30, M 10 Responses Oct 16

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    I have enjoyed wearing a pretty dress, or cute skirt & blouse. My biggest thrills were the ones I had in my teens. I had already bought my own panties, panty girdles and lacy cup...
    carolannP carolannP 61-65, M 2 Responses a week ago

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    One day and soon it will get colder. Yay! I love wearing tights, boots, and long sweaters with my dresses. It's so cozy. I can't freaking wait. Even when it snows my dresses and I...
    lovedaria lovedaria 26-30, F 2 Responses Oct 8

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    What a day! After everyone left the house I put on my girl clothes. Black and white flared skirt, a white pullover sweater and all of the correct under garments. The sweater was...
    mat2Robin43 mat2Robin43 51-55, M 15 Responses Oct 13

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    I like wearing short dresses or mini skirts when doing out. I do not wear pants ever. I have long legs and prefer showing them off.
    computerbusinessmom computerbusinessmom 36-40, F 9 Responses a week ago

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    I went out again today. First to a costume party. Since everybody was in some sort of costume it wasn't too bad. After that I went grocery shopping in my dress. I loved doing...
    Dora922 Dora922 31-35, T 5 Responses 5 days ago

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    I'd describe myself as a straight, in the closet , cross dresser. For years I used fancy dress parties as an excuse to dress up, and , to be honest , i've always had a thing about...
    donnaka donnaka 36-40 5 Responses 4 days ago

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    Getting colder here now, so wearing skirts and dresses are not always an option. Unless you got a really warm long coat lol.
    StockholmblondiE StockholmblondiE 22-25, F 2 Responses Oct 13

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    Ohio winters aren't the most conducive for skirts and dresses but paired with some killer tall boots, it can be done. My favorite dresses are sundresses, I won't see any again...
    rosieredmittens rosieredmittens 36-40, F 4 Responses 1 day ago

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    Ah like wer dreess become part is a hot girl the other is a boy I want be a hot girl and the drees make u more sexy and hot
    jacobbarry12 jacobbarry12 16-17, M 3 days ago

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    ​I always go to the mall with my bae and try on dresses all day
    CapnAlairaQuinn15 CapnAlairaQuinn15 16-17, F 5 days ago

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    this is my normal every day clothes. I may own a couple pair of shorts and a couple pair of jeans but I have a closet full of skirts and dresses, love the looks I get and the fresh...
    Donna15K Donna15K 31-35, F 12 Responses Oct 13

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    Every since i was around 9 or 10, i wanted to wear a dress and cute skirt and tops. My parents did not like the idea at all. But the thoughts of me in a dress with heels or skirt...
    ca042578 ca042578 36-40, M 1 Response Oct 16

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    I wear skirts 2 or 3 times a week. They are comfy and I like the look.
    0hBrandie 0hBrandie 41-45, M 1 Response a week ago

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    Being a woman and working outside the home, I must wear either a dress or a skirt and blouse as my office work attire. When I get home I love to remove my clothes and put on...
    olderandmaturefemale olderandmaturefemale 46-50, F 7 Responses Oct 3

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    So I'm going through college right now, and don't have money to buy stuff like girl clothes. But if you buy me something off my wish list I'll send you a whole bunch of sexy pics...
    Poopoohead17 Poopoohead17 18-21, M 2 days ago

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    on Thursday I wrote about how I was going to go out this weekend dressed in my female persona. I just want to say and OH MY GOD! It was so much fun. I didn't want to come back...
    Dora922 Dora922 31-35, T 11 Responses Oct 18

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    And panties if you have a bubble butt yes
    Masterlicks Masterlicks 31-35, M 1 Response Oct 16

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    dont you think tht they gonna have large collection to choose
    sam94123 sam94123 22-25, M Oct 17

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    I have to walk over to the next building of my complex to use the laundry facility. In the beginning I would just have some hose on underneath my pants and walk there with no shoes...
    nyloncrush nyloncrush 41-45, M 2 Responses Oct 14

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    Most days I do. Sometime jeans are better.
    SweetKimber5 SweetKimber5 46-50, T 3 Responses 23 hrs ago

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    I haven't been able to get sleep in three days :(
    Princessinmind Princessinmind 18-21, F Oct 18

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    i would of loved the idea of having a mum putting me through petticoat discipline as a little boy, making me wear dresses & petticoats. perhaps modern day mums should start it...
    GirlyAndrea1987 GirlyAndrea1987 26-30, M 1 Response Oct 16

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