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

Personal Stories, Advice, and Support 700 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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    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 4 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 6 Responses May 20, 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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    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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    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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    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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    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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    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'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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    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

    After that dressing up with my cousin for a photo, i started feeling jealous of what girls used to wear. They always have more dresses to wear. All so comfy and cosy... In my...
    priyacbe2k1 priyacbe2k1 31-35, F Nov 8

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    Not just boys but men as well. We are all tied up in other people expect that we lose sight of who and what we are. We do what ever everyone else wants us to do. We do not stand up...
    Adam59 Adam59 56-60, M 1 Response 6 days ago

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    I'm transgender, but gender doesn't matter on what you like to wear. I mean.. sometimes I'll feel like I'm less of a boy when I wear "girl" clothing, but w/e. I love wearing those...
    SleepyGamers SleepyGamers 13-15, T 4 Responses Nov 10

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    No I'm not gay. I dress for comfort and I prefer dresses and skirts. If clothes dictate whither or not your gay, then every women that wears pants or shorts, the only accepted male...
    Adam59 Adam59 56-60, M 3 Responses Nov 19

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    Before I moved I used to wear my friends sisters stuff when they weren't home. I would sneak in through a really large window that was always unlocked an make my way to her room. I...
    LexyCD LexyCD 18-21, M Nov 16

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    I started dressing when I was 11 or 12. I would wear my step mom's clothing any chance I could. I still dress every chance I get and love wearing dresses and skirts
    jasminecd5 jasminecd5 36-40, M 4 Responses Nov 1

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    Yes I love wearing dresses. They are so liberating. My feminine side can be herself. Not shoved into pants. Rather being the classy lady that she is.
    Adam59 Adam59 56-60, M 1 Response 1 day ago

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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 1 Response 15 hrs ago

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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 6 Responses Oct 27

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    I have all manner of things in my feminine wardrobe; skirts, panties, tights, some pantyhose, leotards, slips both half and full, Spandex shorts both half thigh to almost no leg...
    wcurnow wcurnow 46-50 Nov 5

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    Dressed as girl for Halloween To Halloween I attended a costume party. A good opportunity to jump into a dress a be a girl some ours. I tried to find a dress on the internet, it...
    ToShareStories ToShareStories 22-25, M 8 Responses Nov 14

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    Why shouldn't i. I'm wearing one right now. Dresses are so comfortable and allow freedom of movement. There is nothing dragging on the legs or cinched up around the waist. I prefer...
    Adam59 Adam59 56-60, M 5 Responses Nov 12

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    ok , so here goes for the second time. if you've read my first post, you'll know what a rush I got from being out in the street and passing , for all of 5 minutes. i attribute...
    donnaka donnaka 36-40 1 Response Nov 4

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    dressing in public number 3. Who else has made this journey- having a single item you obsess about for years (often panties , i believe , but mine was tights) , telling yourself...
    donnaka donnaka 36-40 9 Responses Nov 4

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    I have several coloured dresses, black, blue, red, crotchet etc....but i really like to wear a white men's shirt as a minidress, it is very comfortable in summer, airy and soft on...
    HeelsKitten HeelsKitten 31-35, F 14 Responses Nov 8

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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 Oct 28

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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 2 Responses Oct 31

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    Shopping trip planned for later this week to get a couple of dresses for Christmas parties.
    ris9358 ris9358 51-55, M 4 Responses Nov 4

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    dresses are the best thing in the world. love spinning around in them
    ladeputy ladeputy 22-25, F 5 Responses Nov 10

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    I Love Tight Dresses And Skirts. They look great and really make me feel feminine
    jasminecd5 jasminecd5 36-40, M 3 Responses Nov 10

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    Thank you all for your wonderful comments. I am encouraged to show you another short dress. It is crotchet and daring for me because i never wear a bra. Although the shoes i wear...
    HeelsKitten HeelsKitten 31-35, F 12 Responses Nov 13

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    I wear them all the time at home. Feels so comfortable and natural. I like to look good so everything must match. I would like to be able and accepted to wear them all the time.
    Adam59 Adam59 56-60, M 10 Responses Nov 14

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    I decided to go out and buy my first skirt in public today. I saw this maxi skirt on JCPenny online and been eying it for awhile. I found out they had some near a store near me and...
    ExpandingHorizonsForMyself ExpandingHorizonsForMyself 22-25, M 3 Responses 18 hrs ago

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    I think wearing a dress or a skirt and a blouse with hose and high heels is wonderful. I love dressing up when going out to work and after work to.
    singleandpregnantmom singleandpregnantmom 31-35, F 3 Responses Nov 15

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    I don't usually, but there's one guy who used to get turned on by me wearing women's clothes, so sometimes as a treat I would do my best to dress as a woman for him. We always had...
    bd693 bd693 18-21, M 3 Responses 2 days ago

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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 Oct 28

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    I have never cuddled before. How does it feel? I'll probably never know :( I have no experience of any physical intimacy with anyone, not even family. Even receiving a hug is...
    acopalypse acopalypse 22-25, M Nov 5

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    Well I did it went to Halloween as a girl still in the dress as a matter of fact. Only problem was my friend forgot my makeup and jewelry. But it turned out okay because another...
    Hiddensissy69 Hiddensissy69 26-30, M 6 Responses Nov 1

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    After taking a break two weekends ago I spent this past Saturday as a female. I met up with someone for lunch and then went to a BDSM club with my wife. I was so excited to at...
    Dora922 Dora922 31-35, T 4 Responses Nov 10

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    Here is me in a skirt and a top and also tights
    Cdallaslover99 Cdallaslover99 13-15, M 3 Responses Nov 10

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    Most days I do. Sometime jeans are better.
    SweetKimber5 SweetKimber5 46-50, T 3 Responses Oct 30

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    Any girl want me treat u as sl////// ut
    misstress2015 misstress2015 31-35, F 2 Responses Nov 16

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