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

Personal Stories, Advice, and Support 730 People

    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 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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    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 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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    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 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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    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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    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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    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 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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    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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    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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    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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    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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    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 10 Responses a week ago

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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 11 Responses Oct 16

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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 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 18 Responses 6 days ago

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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 4 Responses Oct 1

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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 2 days ago

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    None of my friends or family have any idea but when I get home at night and if I have no prior plans the first thing I do is shower shave or wax if I need it then spend a glorious...
    Jimhes Jimhes 31-35, M 6 Responses Sep 30

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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 14 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 1 day 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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    Until lately, my dress code for work was just nice looking dresses and skirts. Now my boss decided a white suit is much better ... Even as personal assistant, I spend a lot of time...
    LittleStain LittleStain 18-21, F 3 Responses Sep 30

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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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    Isn't it just the best? Wearing soft female clothes instead of boring male ones? My favourites are tights, skirts and panties.
    Dannjazz Dannjazz 22-25, M 5 Responses Sep 30

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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 1 day 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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    Anyone wants to add me feel free also if you want to know anything or ask anything just msg me thank you xx
    cutieXtights cutieXtights 22-25, F 3 Responses Sep 29

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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 8 Responses a week ago

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

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    dont you think tht they gonna have large collection to choose
    sam94123 sam94123 22-25, M a week ago

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

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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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    It was another uneventful function at my uncle's home. A lot of female relatives were present there. One of the guests was a close friend of my mother as they had taught together...
    priyankapatel131089 priyankapatel131089 22-25, F Oct 6

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    Hello everyone!!!! sorry it been so long. Any way im going to tell you the TRUE story on how i started wearing one piece swimsuits instead of some made up one grrrrrr. Anyway i...
    Conzo101 Conzo101 16-17, M 1 Response Oct 9

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    I have worked in this café for 2 years. I laid an eye on him on first sight. He is quiet, friendly looking and mysterious. He came to the coffee shop everyday for a coffee, but no...
    seraphurn seraphurn 22-25 13 hrs ago

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    I always felt so jealous when I saw little girls wearing what I should have been wearing. I always wanted to wear dresses and frocks and skirts and nighties. I loved twirling in...
    Iamsasha Iamsasha 18-21, F 1 day ago

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    I often have the hard decision of choosing what colour nail varnish to wear, should I wear black like the colour of my soul or red like the blood of my victims?
    iloveyousomuchdontforgetit iloveyousomuchdontforgetit 13-15, F 15 hrs ago

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