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

Personal Stories, Advice, and Support 732 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'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 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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    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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    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 18-21, M Jan 11

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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 5 Responses Jan 11

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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 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 70+, M 2 Responses Nov 11, 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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    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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    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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    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

    Wearing skirts, dresses, and looking pretty makes me happy, so should I do it in public? I wish it was as simple as "if it makes you happy, do it", but it's not :(
    WalterStuart22 WalterStuart22 18-21, M 1 Response Jan 9

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    I do agree, I think that all boys, at least at some stage of their lives, should be allowed to experience how wonderful wearing cloths made for girls could feel. They should be...
    mizmaid mizmaid 36-40, M 7 Responses Jan 11

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    Wearing dresses at home There are only a few occasions I'm wearing dresses in public: On halloween or other opportunities where it is "normal" or somehow accepted for men wearing...
    ToShareStories ToShareStories 22-25, M 12 Responses Jan 14

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    I love wearing dresses :3 I love them a lot
    AshleyNicolee AshleyNicolee 18-21, T 10 Responses Jan 3

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    I love wearing dresses, they feel so much better than boring mens clothes. Slipping in to a nice dress feels so sexy, wish I could spend more time in them and head out full time...
    GirlyLisaTG GirlyLisaTG 26-30, T 2 Responses Dec 29, 2014

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    I begun to dress as a Girl early my 9 or 10 years but knowing that it was a "sin", always where in secret. When I reached 14 year old, I got my first best friend (a Girl called...
    L0yd L0yd 31-35, M 7 Responses Jan 6

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    2014 Review 2014 was a year of firsts in my crossdressing adventures, as I was able to go out dressed for a new record number of hours. Some of those extra hours were those that I...
    1SarahAnn 1SarahAnn 46-50, M 5 Responses Jan 4

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    As biologically male, I love wearing skirts!! I envy females cause my area gets way too Hot down there and needs cold air to freshen if up often!! I HATE Pants!! It's just Wrong...
    AsianTransGirl AsianTransGirl 26-30, T Dec 29, 2014

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    I had a dream last night that I was with my friends that are girls, and somehow they found out I like wearing girl's clothes, and started getting excited about it. They took me to...
    WalterStuart22 WalterStuart22 18-21, M 1 Response Dec 30, 2014

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    I love the way dresses or pleated skirts twirl around my stockinged legs when I walk in them.
    nikkitran nikkitran 51-55, T 11 Responses Jan 2

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    so I had my day out. an early start , a few hours drive. The appointment was in an open salon. Sadly , early on a tuesday morning there were no other customers. i wore the same...
    donnaka donnaka 36-40 4 Responses Jan 11

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    i need advice on how to start to come outside of the house wearing more female clothes i always wear girls underwear but i want to wear more NEED ADVICE!!
    lovegfpanties lovegfpanties 18-21, M 7 Responses Jan 14

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    My wife has caught me wearing panties so many times I think she has given up on trying to stop me. At least she knows I don't wear hers.
    tgkristenmarie tgkristenmarie 56-60, F 3 Responses Jan 5

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    i am gong to remove my night gown now. Reding to go to work i am going to wear my my wife panty she prefer for me all her cloth that i can wear to my work....... i love her so much...
    daya55 daya55 26-30, M Jan 18

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    what are you wear now.... i have wear my nightgown
    daya55 daya55 26-30, M 5 Responses 2 days ago

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    I just watched the film (movie), "the boy in a dress". It moved me deeply. I highly recomend it to all of you. X
    Heellover Heellover 36-40, M 7 Responses Jan 1

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    New Years Eve 2014 My wife and I have spent the three previous New Year’s Eve nights out of town at small hotels. Each of these hotels had a small lounge and a party to bring in...
    1SarahAnn 1SarahAnn 46-50, M 3 Responses Jan 6

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    i am with my new nightgown today its so silky and long i wont to buy one more am on the bed lookin my self. i am not a lady boy i love wife mor but i like it
    daya55 daya55 26-30, M 1 Response Jan 16

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    what color dress are u going to wear today
    daya55 daya55 26-30, M 11 Responses Jan 16

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    hi girls is it okay if your husband wear your nightgown on bed with you to sleep
    daya55 daya55 26-30, M 2 Responses Jan 18

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    This is not really a story but I am looking for advice. I have my mind up to come out of the closet. My first time will be Thursday and looking for advice on how far to go or what...
    SylviaJames SylviaJames 56-60 6 Responses 3 days ago

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    I don't know what pantyhoses are, but I already hate them. I don't like wearing skirts and dresses; I feel naked. And when the horny wind blows and lifts it up, they practically...
    SweeterThanToblerone SweeterThanToblerone 13-15, F Jan 5

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    i liked a girl , but closer i tried to get to her further she went ! i was so obsessed that when i could not find her anywhere i tried to find her within me , I met her and talked...
    navchetan navchetan 26-30, M 2 Responses Dec 30, 2014

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    I like thongs to and skirts mmmmm
    Ericaloves Ericaloves 22-25, M 1 Response Dec 30, 2014

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    My wife and I were able to get out for a couple of weekends of Holiday fun recently, and had some very interesting experiences while I was dressed as Sarah. The first one was at a...
    1SarahAnn 1SarahAnn 46-50, M 3 Responses Jan 4

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    LIKE THIS PAGE PLEASE https://m.facebook.comprofile.php?id=1534157783490006
    daya55 daya55 26-30, M Jan 19

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    this way if they are gay they can pull up the skirt like a good girl.
    aqww aqww 13-15, M 2 Responses 11 hrs ago

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    Yeah I may enjoy doing things that other people are scared of, but that's just because they've never done their research haha. I'm secretly really freaking awesome. I just don't...
    SarcasticBadger SarcasticBadger 16-17, M Jan 4

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    I luv my dress omg what do u think?
    AshleyNicolee AshleyNicolee 18-21, T 82 Responses Jan 5

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    How do i look? :)
    shadowhero92 shadowhero92 22-25, M 1 Response Jan 5

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    I know this isn't a dress or anything but I loved the support I was getting last night for my dress I had to post this picture for all you lovely people. If you want add me on...
    AshleyNicolee AshleyNicolee 18-21, T 5 Responses Jan 6

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