Post

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

Personal Stories, Advice, and Support 707 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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    Related Experiences

    A little conversation with my 3 year old daughter the other day. She was wearing a pretty little dress, spinning round so the skirts puffed out. She looked so cute. She turned to...
    Heellover Heellover 36-40, M 9 Responses Aug 8

    Your Response

    Cancel
    Got to wear a dress an entire afternoon and evening after work on two days this past weekend... It was so nice. Since my family was out for the weekend I didn't have to worry about...
    Roccondil Roccondil 22-25, M 9 Responses Aug 7

    Your Response

    Cancel
    Hi guys in need of some advice about my boyfriend and the relationship he has with his sister. Myself and my boyfriend have been together for just under 3 months, although have...
    angrykid123 angrykid123 22-25, F 2 Responses Aug 9

    Your Response

    Cancel
    So, to day was my last picture day, and I decided to wear a pretty white dress it's so cute, and perfect for summer! I never wear dresses but, I love them I really want more.
    Vannarose Vannarose 16-17, F 1 Response 6 days ago

    Your Response

    Cancel
    Wearing dresses make me feel more feminine
    KinkyKatieLouise KinkyKatieLouise 46-50 6 Responses Aug 13

    Your Response

    Cancel
    I'm Pentecostal so I have my reasons. Besides my religion, I enjoy wearing dresses and skirts instead of pants. Pants are so uncomfortable.
    PeaceBatman PeaceBatman 22-25, F 5 Responses Aug 16

    Your Response

    Cancel
    I like to wear dresses or skirts - and preferably short ones - as often as I can. Partly because I like to feel - and look - feminine - and because my husbands loves to see me that...
    Susanna3 Susanna3 31-35, F 4 Responses 6 days ago

    Your Response

    Cancel
    I wish at least once that one girl in the world would give me a bit of attention. It would be nice to speak to a girl and she talk back rather than walk away. Why do girls not...
    memph31 memph31 31-35, M 2 Responses 4 days ago

    Your Response

    Cancel
    When I grew up I did at least in private and sometimes not so private wear short pleated skirts and the occasional pinafore style dress. This was not a punishment and indeed I am...
    littlegreyshorts littlegreyshorts 51-55, M 4 Responses Aug 1

    Your Response

    Cancel
    I love wearing them! They are really comfortable, and hug your body so well, especially with their interesting fabrics. And of course the lower body freedom. I would not want to...
    Roccondil Roccondil 22-25, M 10 Responses Aug 1

    Your Response

    Cancel
    Isn't it amazing that a single moment in time can flip a switch inside of us and nothing is ever the same? I can think of a hundred things that might have affected me in a...
    kayleew2000 kayleew2000 18-21 13 Responses Aug 16

    Your Response

    Cancel
    OK... Google the phrase "shopping tunic", then click the "shopping" tab. You'll see that pretty much all the results are for "women's tunic dresses". Then search "gladiator sandals...
    steve66oh steve66oh 46-50, M 6 Responses Aug 11

    Your Response

    Cancel
    I have worn dresses or skirts since i was 6 but i would love to live in a world where a boy can wear them openly instead of having to be called a cross dresser. i hope that day...
    jamie172 jamie172 46-50, T 9 Responses Aug 4

    Your Response

    Cancel
    This has to be one of the worst and unchallenged stereotypes ever. Just because a boy is feminine, it has nothing to do with his sexuality. It's been my privilege to know many...
    MrsJoanieBNH MrsJoanieBNH 56-60, T 4 Responses 1 day ago

    Your Response

    Cancel
    So a couple of months ago I told my sister I wanna crossdress ( she thinks this is my first time curiosity) she said she'd help me dress when she came home for the summer... Well...
    Marissatgsissy Marissatgsissy 18-21, T 8 Responses Jul 27

    Your Response

    Cancel
    I love to dress up and wear short dresses and skirts with a nice looking blouse or top. Also, I love to wear shorts and swimwear with hose and four inch high heels on.
    tammylynne tammylynne 41-45, F 8 Responses Aug 10

    Your Response

    Cancel
    I wear a dress as often as possible. It's such a free feeling. You don't have to wear underwear if it's not see thru. I love the way they look, especially the long ones that are...
    jaylow13 jaylow13 36-40, F 2 Responses Aug 18

    Your Response

    Cancel
    I love to wear my short dresses with thigh high boots :)
    PoojaTimberlake PoojaTimberlake 18-21, F 9 Responses Aug 8

    Your Response

    Cancel
    I can't wait to get home from work and get out of my work clothes. I take a shower and shave all my body hair. I then get out and lotion all my body. Then I pick out panties and...
    Michelle1976 Michelle1976 36-40, T 6 Responses Aug 16

    Your Response

    Cancel
    I usually only wear them on special occasions like a birthday or something, except in the summer i wear them if its too hot out and i need to feel fresh, like i feel the need to do...
    violet1698 violet1698 31-35, F 5 Responses Aug 11

    Your Response

    Cancel
    My dad says I can wear whatever I want at home. He bought me a skirt. A pink one. When I wear it, I wear only my skirt. I'm kind of growing out of it, you can sort of see my junk...
    gayandproud13 gayandproud13 13-15, M 1 Response 5 days ago

    Your Response

    Cancel
    I loved wearing miniskirts as a teenager and a young woman. I wore them in preference to jeans or trousers where possible. However, they did have their own hazard! One day, when we...
    Jilly53 Jilly53 56-60, F 5 Responses Aug 16

    Your Response

    Cancel
    I wish I could be Abby all the time
    abbyseaney abbyseaney 16-17, T 6 Responses Aug 5

    Your Response

    Cancel
    I'm going to be posting and sending nude pics or will be on Skype so add me kik: missjazzmin Skype: misscrossdresser
    missjazzmin missjazzmin 18-21 2 Responses Aug 11

    Your Response

    Cancel
    Lately with a pair of black leggings. I must admit my legs look great in them.
    deleted deleted 26-30 2 Responses Aug 13

    Your Response

    Cancel
    I have no problem with those who are but even through I dress as a woman I can not see myself having sex with a man not that I have not thought about it
    jamie172 jamie172 46-50, T 4 Responses 1 day ago

    Your Response

    Cancel
    All the time now, except at work. My favorite dress ATM, is floral, tight around the bust, with spaghetti straps, and flowing at the bottom. So comfortable!
    deleted deleted 26-30 7 Responses 19 hrs ago

    Your Response

    Cancel
    It does make a difference. Emphasises femininity I guess.
    picklebobble picklebobble 46-50, M 1 Response Aug 8

    Your Response

    Cancel
    Before I start this, I want to say that I know that this shouldn’t upset me as much as it does. The problem is my boyfriends’ brothers’ girlfriend (my boyfriend and his...
    faithtrustandpixiedust faithtrustandpixiedust 22-25, F 34 mins ago

    Your Response

    Cancel
    Last Year yayayayayayayayay I didnt go out for a good bit so here is a story of other people showing their cracks. Me and a bunch of my friends including my closest girl friend...
    KSISp33dstar123 KSISp33dstar123 18-21, M 1 Response Aug 10

    Your Response

    Cancel
    Growing up, i was a normal kid. I liked to play with dolls and barbies, but also with dinosaurs and cars... The more i grew up, the more i hated to wear dresses and feminine...
    yoyo1324 yoyo1324 18-21, F 1 Response Aug 17

    Your Response

    Cancel
    My first experience with thong bikini happened unexpectedly. I was planning summer vacations with my sister and this time we decided to visit Spain (oh, it's wonderful!!!) I've...
    Alishakiss Alishakiss 22-25, F 2 Responses Jul 29

    Your Response

    Cancel
    I am NOT a feminist because I am not a victim. I never have, nor will I ever, see myself as a victim. I am not subjugated, controlled, or misled by the male population. I can wear...
    Meriyne Meriyne 18-21, F 1 Response Aug 12

    Your Response

    Cancel
    Apart from shorts, I have only been wearing dresses or skirts since I was 8 or something. An