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

Personal Stories, Advice, and Support 869 People

    Hi I'm a 15 year old sissyboy

    who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns skinny jeans heels and definetly make up and I also secretly am attracted to masculine tough and hairy men
    deleted deleted 26-30 Oct 14, 2015

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    Im a 15 year old sissyboy

    who secretly wears his 17 year old sisters cloths bikini bra panties lingerie dresses gowns skirt tank tops leggings tights yoga pants and definitely make up and I secretly like hairy tough masculine men both genders feel free to message me
    deleted deleted 26-30 Jan 21

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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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    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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    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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    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 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'm a 15 year old sissyboy

    who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels and definetly make up and I also secretly am attracted to masculine tough and hairy men
    deleted deleted 26-30 Dec 30, 2015

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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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    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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    If I wear a dress and wear my hair girly

    and it hurts no one ... So what, happiness is all that matters
    Dryermaniac Dryermaniac 46-50, M 2 Responses 2 days ago

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    You can, you just have to be prepared

    for the reactions u'll get. U will have to take some negativity. But u can and if u want to u should. But it shouldn't have to be like this, getting negative comments just cuz u r dressin how u want to
    darkspiritwolf darkspiritwolf 18-21, F 3 days ago

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    I like to wear cute frilley dresses

    but its hard i dont want to be hated for it
    drifterx212 drifterx212 22-25, T 4 Responses Mar 10, 2014

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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'm a 15 year old sissyboy

    who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels and definetly make up and I also secretly am attracted to masculine tough and hairy men
    deleted deleted 26-30 Dec 11, 2015

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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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    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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    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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    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, 2015

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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 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...
    TaylorStuart TaylorStuart 18-21, T 4 Responses Jan 11, 2015

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    I'm a 15 year old sissyboy

    who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns heels lipstick skinny jeans heels and definetly make up and I'm secretly attracted to masculine tough hairy men
    sissyboyteen sissyboyteen 13-15, M 1 Response 3 days ago

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    I'm a 15 year old sissyboy

    who secretly wears his 17 year old sisters bra panties bikini lingirie tights leggings dresses skirts tank tops gowns skinny jeans heels and definetly make up and I also secretly am attracted to masculine tough and hairy men
    deleted deleted 26-30 Dec 5, 2015

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    Related Experiences

    i like to wear midriff tops especially in the summer time or like in the spring. pretty much when the weather is warm or hot and even sometimes in the winter. i been wearing...
    sonyatubetop88 sonyatubetop88 22-25, F 1 Response 1 day ago

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    And though I know it would never actually happen, I would not be averse to society demanding and requiring that ALL women and girls wear dresses and skirts all the time and banning...
    MrsAshleyR MrsAshleyR 18-21, F 2 Responses 2 days ago

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    I am with the love of my life. In 2002 we were good friends, then dated each other for a while, fell in love, only for us to get into a huge argument, part and go our separate...
    MartiniMagic MartiniMagic 36-40, F 1 Response 2 days ago

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    Hot and spicy is the best idk why I just like it I mean I eat normal stuff to but I love spicy stuff idk why I must be like part Canadian or something
    CallMePonyTail CallMePonyTail 13-15, F 3 Responses 3 days ago

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    Will wear anything on cam if I can find it, will do almost anything really ahah - text me for some good chats guys;)
    Shadrinz01 Shadrinz01 13-15, M 3 days ago

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    Yesterday was a good day for me and a bad one too. Good day: I invited my daughters over for a taco dinner night. Just a time to be with them and converse. Had a great meal and...
    shadowplt shadowplt 51-55, T 5 Responses 3 days ago

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    It's a little weird feeling. In not a fan of Facebook and hardly use it much. I changed my profile picture yesterday (not because i was sad, instead, i was really happy and...
    kasiyat kasiyat 26-30, F 1 Response 5 days ago

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    I love to dress up as a women in sexy under wear and stocking and high hills and play with my self
    janetjanet janetjanet 51-55, T 1 Response 6 days ago

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    So, I'm very shaken up. A few weeks ago, my boyfriend received multiple calls, texts, and friend requests from his ex-girlfriend. I didn't think much of it, I thought it was an...
    Iamvindicated Iamvindicated 18-21, F 1 Response a week ago

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    I don't wear panties or a bra when I wear skirts or dresses #FreeTheNipple #Commando
    deleted deleted 26-30 Jan 29

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    I'm actually the wife of one whom I support and love fully.
    girlonpause girlonpause 36-40, F 7 Responses Jan 29

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    And I hate it when people ask me that. I always reply with a smile and I just shrug my shoulders. I don't know why I'm quiet. I hate it and I don't know how to explain. That's why...
    EnigmaticPerson EnigmaticPerson 13-15, F 1 Response Jan 27

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    I remember the one time that I cried my eyes out at school in front of my small class of 12 students. Thankfully only two other people close to me saw. But it was a really...
    lunarrose123 lunarrose123 16-17, F 1 Response Jan 27

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    Once you put on nylons over freshly shaved legs it's hard to stop. I shave my legs every other day and can't wait to put on some nylons over my painted toes and sandals or high...
    stephenjstasiowski stephenjstasiowski 46-50, M 2 Responses Jan 26

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    Best thing for women to wear. Nothing shows off the booty more. ;) although the more fit you are the better you can pull off something like this. I also love how the thong bikini...
    deleted deleted 26-30 Jan 26

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    Every now and then, I get this overwhelming feeling. I start noticing how most people I meet or know don't talk to me. My family puts me on the bottom of their priority list and...
    Dereth Dereth 26-30, M 2 Responses Jan 26

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    This is probably my favourite outfit and one that I scarily venture out into the real world in. Wish me luck that I survive the strange stares and giggles as I totter along on my 5...
    deleted deleted 26-30 1 Response Jan 25

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    Tartanpleats, You were probably invove in this original thread. My observations while standing in a Kiltmakers shop in my old Kilt and Argyll going through two book of Tartan...
    kiltiekid kiltiekid 66-70, M 1 Response Jan 24

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    I love wearing dresses and skirts. They look nice with shoes and stockings and flow nicely when walking. I just like being feminine.
    Sienna32 Sienna32 26-30, F 4 Responses Jan 24

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    Been wearing my Skirts, by gender they are Gentleman's Skirts, for thirty years. No one has time to bother what I wear. I like to look smart or casual. definitely a man in a Skirt...
    kiltiekid kiltiekid 66-70, M 1 Response