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

Personal Stories, Advice, and Support 720 People

    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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    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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    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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    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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    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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    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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    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 4 Responses Mar 1, 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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    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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    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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    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

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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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    Related Experiences

    This is another example of how a restrictive EP entry style followed by the removal of maintained groups with icons has made things worse over the years. Really the style should...
    Joanne0chan Joanne0chan 31-35 Dec 15

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    Hello everyone. :) Hope you are having a nice day and I wish you great Winter Holidays.. I guess I should start with telling that I am a very sensitive person, lets say over...
    AnnaLeah94 AnnaLeah94 18-21, F 5 days ago

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    I have always enjoyed wearing feminine clothes and makeup but only to relieve myself. And when I am done with that I usually remove all the makeup and feminine clothes. Now when I...
    sexysissy11 sexysissy11 18-21, M 4 Responses Dec 16

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    It so happens that there was a long time before my opportunity to go out a 4th time. But in the summer my wife was going away for a week-end. I was so excited!! I shopped around...
    donnaka donnaka 36-40 3 Responses Nov 27

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    Just put in an order for this amazing dress from the Ashley Roberts Key collection.. I cant wait for it to come. You gen girls are so lucky to be able to buy these dresses and wear...
    cdlovingguy cdlovingguy 31-35, M 6 Responses Nov 30

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    I just had a once-in-a-blue-moon opportunity... I recently visited a local thrift shop and to my excitement I discovered on the dress rack a figure skating dress just about my size...
    Roccondil Roccondil 22-25, M 7 Responses Dec 17

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    I've been wearing this one all afternoon.I dared myself and ventured out, TWICE! Once was through a drive-thru to get a bite to eat. The other was to the RedBox outside the local...
    JosetteLaRoc JosetteLaRoc 36-40 7 Responses Dec 9

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    My style has become progressively more feminine over the last few years. In some ways at odds with that is my continued disinterest in the sort of embellishments I loved as a teen...
    morea morea 22-25, F 2 Responses Dec 1

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    As a transgendered Catholic boy who was forced to grow up male, I remember my first communion and wanting so desperately be one of the girls dressed in a beautiful communion dress...
    tessoconn tessoconn 18-21, F 2 Responses Dec 2

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    Ok so recently I find only girly crossdressers that may or may not have fake boobs:)and because I am a girly crossdresser ever since I wore my sisters dress at age 12:)I just...
    HeatherVictoria00 HeatherVictoria00 18-21, M Dec 3

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    I generally wear a dress or skirt to work, and a dress or robe at home. I just feel more comfortable. I only wear jeans if a dress is not practical.
    Sarah1990x Sarah1990x 22-25, F 5 Responses Dec 8

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    I hate wearing skirts ever since my step dad started touching me so no I don't like them
    cattie1283 cattie1283 18-21, F 3 Responses Dec 8

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    I've been wearing this one all afternoon.I dared myself and ventured out, TWICE!It was my first time out dressed in the day time.I went to the local RedBox outside the local...
    JosetteLaRoc JosetteLaRoc 36-40 5 Responses Dec 9

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    I try my best not to dress like a woman. I can can keep it under control for a month maybe two. But there isn't a day that goes by that I don't think about it. Eventually the...
    chrissyk48 chrissyk48 46-50, M 9 Responses Dec 13

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    I love dressing up when my husband and I are out for the evening alone and/or with other couples. We all love eating out and then doing dancing on Friday or Saturday nights. We...
    wifeinbackyard wifeinbackyard 31-35, F 2 Responses Dec 8

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    I like to dress mostly on the bottom half of my body mini skirts loose gstrings and high heel boots it surprises people when I bend back up and they see im a guy but alot of them...
    Donpi Donpi 18-21, T Dec 1

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    I wear a Prince's Wand and have for years
    happyguy99 happyguy99 66-70, M Nov 28

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    How come society makes us feel bad for thinking out the box when all the time it's made up to control us. Come play at secreterotica . com it's sexy, fun the groups and library are...
    YouKnowItMakesSense YouKnowItMakesSense 31-35, M Nov 28

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    Headed out on an adventure tonight. Next stop is Payless for a new pair of shoes.
    CDKristiK CDKristiK 51-55, M 8 Responses Dec 5

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    I'm a girl, to be honest with everyone here. I love to get on this experience page and read what you all have gone through. This is a truly amazing and inspiring section you all...
    Emilia0659 Emilia0659 18-21, F 14 Responses Dec 6

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    Found this pretty dress at goodwill.
    jazz2013 jazz2013 56-60, M Nov 30

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    Panties, hose, bra, eye makeup and lipstick and off shopping. Pretty dress at home.
    jazz2013 jazz2013 56-60, M 3 Responses Nov 30

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    I love to be dressed up fully as a woman then wrapped up tightly in shrink wrap so I can't escspe
    aldi1106 aldi1106 31-35, M Dec 1

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    makes everything so much faster and by everything i mean EVERY THING ;)
    kittylips kittylips 18-21, F 5 Responses Dec 7

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    just cause I got a perky bubble butt and my butt is there doesn't give you the right to give it a slap cause it hurts!!!
    Donpi Donpi 18-21, T 1 Response Dec 8

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    i love to go out fully dressed as a woman with heels, wig, makeup and whatever dress or skirt I fancy that day.
    nikkitran nikkitran 51-55, T 8 Responses Dec 9

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    Christmas day...The 1st dressed as Amber now the truth is out, New leather dress black stockings and high heels, but stillcooking the Christmas dinner, Dress so good you can clean...
    amber8642 amber8642 51-55 5 Responses 2 days ago

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    no ill never stand for my life to get this low again! no way no how!
    wickedlilangel69 wickedlilangel69 31-35, F Nov 29

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    No, it's true, there are girls out there who admire us toothless chaps. Thank the Lord.
    ledertal ledertal 51-55, M 6 days ago

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    My best friend uncle made me dress a girl and raped me about two years For years I thought I was gay for liking it and enjoyed dressing as a girl
    sarahbethsarli sarahbethsarli 46-50, T 1 Response Dec 18

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    My mother encouraged my crossdressing at an early age 11 she was happy to let me wear my older sisters panties and bras. I'm sure this is why I have always been a sissy.
    esililedsisi esililedsisi 36-40 1 hr ago

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    She's popular and has all these friends and I don't and everyone wants me to be like her. Why? She may be pretty and crap but her grades blow, mine are better. I apparently dress...
    SphiSphi SphiSphi 18-21 1 Response 4 days ago

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