Post
Experience Project iOS Android Apps | Download EP for your Mobile Device

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

Personal Stories, Advice, and Support 776 People

    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

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    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

    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

    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 4 Responses Mar 10, 2014

    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 3 Responses Dec 2, 2011

    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...
    57Peggy 57Peggy 56-60, M 2 Responses 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 6 Responses May 20, 2011

    Your Response

    Cancel

    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

    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

    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

    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

    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

    Related Experiences

    not many people are capable of making me feel like i matter. idk if its just me not wanting them to or if its them just being self absorbed like everyone else. the world is full of...
    ForgetableMe ForgetableMe 31-35, M 47 mins ago

    Your Response

    Cancel
    When using one of those dating apps where you swipe and swipe pictures, 80% or more has this icy look. I am not even sure if id call it a serious look, it is just kinda flat, icy...
    mirkwood86 mirkwood86 26-30, M 1 hr ago

    Your Response

    Cancel
    I was just a little boy, around the age of 4 or 5, before I started school. I used to put on my mother's hose. I was caught and made to take them off. That was just the start for...
    phlover7 phlover7 18-21, M 1 hr ago

    Your Response

    Cancel
    It seems frustrating...whoever i meet now is like am looking at a piece of wood..no feelings at all..i keep trying to overlook the matter and see the soul but in vain
    kimoboston kimoboston 36-40, M 5 hrs ago

    Your Response

    Cancel
    My involvement with knickers began at the age of six or seven when my sister and her friend, who were two years older than me and my friend, decided to entertain our parents. They...
    alpin5011 alpin5011 70+ 6 hrs ago

    Your Response

    Cancel
    2 years ago I was raped by him, and they put me into a psychiatric hospital. The same night they took me, they came back and got me to take me to children's hospital for a rape kit...
    GodsArte GodsArte 18-21, F 6 hrs ago

    Your Response

    Cancel
    I don't wear makeup because "I need it" I wear it because makeup is my passion . And for people to tell me " oh why do you wear makeup when you don't need it??" Is actually really...
    FlowerChildWithARockNRollSoul FlowerChildWithARockNRollSoul 18-21, F 10 Responses 8 hrs ago

    Your Response

    Cancel
    I wear pantyhose always as long as I remember and love to wear pantyhose very mouch since i was young. It has never been a big deal in our family. So I still wonder why it's just...
    IamPantyhoseboy IamPantyhoseboy 18-21, M 1 Response 9 hrs ago

    Your Response

    Cancel
    Wow! I thought this was going to be the all time creepiest group ever... on my iPad in the "Explore Groups" option it looked like this group was "I am a Guy who dresses head to toe...
    slimmmerman slimmmerman 41-45, M 2 Responses 9 hrs ago

    Your Response

    Cancel
    One day I was talking to my girlfriend (Alexis) who currently plays softball and I play baseball. The sign ups were coming up and bc her team is a big travel team she wouldn't get...
    Collin17 Collin17 13-15, M 15 hrs ago

    Your Response

    Cancel
    I would love to wear old fashioned dresses everyday. I might as well, I have never wore pants or shorts of any kind. I'm almost 45, I'm a plus size, I never have wore pants, shorts...
    JamieCarlin44 JamieCarlin44 41-45, F 18 hrs ago

    Your Response

    Cancel
    22 year old single woman looking for women older than my age to cuddle and be intimate with. I enjoy being nurtured and taken care of. Maybe a future wife may come along, but am...
    RainbowsAndMangos RainbowsAndMangos 22-25, F 1 day ago

    Your Response

    Cancel
    I would like you to share your opinion on this matter. I am single mom with two children and I think I have a good body for a woman at my age, that's why I wear a thong swimsuit...
    Kimberley811 Kimberley811 31-35, F 4 Responses 2 days ago

    Your Response

    Cancel
    I really believe all boys should experience wearing a dress, A feeling comes over you that is incredible, you are happy and friendly, wanting to make others the same.
    CharleeneA CharleeneA 13-15, M 3 days ago

    Your Response

    Cancel
    One would find me in either a short skirt and blouse or a short dress when I am out. I do not wear pants to work because I feel it is unprofessional for me to do so. Besides I am...
    femalemusiclover femalemusiclover 46-50, F 9 Responses 4 days ago

    Your Response

    Cancel
    zip up the back is very nice to have it must feel so sexy if you are with someone and you can feel them slowly unzipping your dress and just slide off that has to be sexy
    dresscross dresscross 51-55, M 5 days ago

    Your Response

    Cancel
    Pot is ok but I hate people that must tell me they smoke it or talk about how they do it. Who cares? I take a **** but I don't get on Twitter and brag about it. Smoke it, ok great...
    iSceneGirl iSceneGirl 13-15, F 4 Responses 5 days ago

    Your Response

    Cancel
    I do wear panties and bras i put pads in them
    wwerwee wwerwee 22-25 1 Response 6 days ago

    Your Response

    Cancel
    It's Summertime!!! That means SUNDRESSES!!! Yay!
    Mrskatearch Mrskatearch 31-35, F 13 Responses 6 days ago

    Your Response

    Cancel
    Terror on Extension 29 Nineteen - Michael Duke I didn't sleep that night after my wife and daughter called me back to report their findings. My theories had been blown right out...
    MaryJanine MaryJanine 56-60, F a week ago

    Your Response

    Cancel
    I'm a boy that likes putting on my sisters makeup 💄 bra panties and high heels 👡 lipstick 💄 dresses skirts
    tmccom123450 tmccom123450 13-15, M 1 Response Jun 22

    Your Response

    Cancel
    ya I too love to be a women and wearind skirt and I have some of them..but right now I am wearing a red saree..and I feel feminine and sexy
    deleted deleted 26-30 Jun 21

    Your Response

    Cancel
    I am a white girl and I've been absolutely fascinated with black boys since I was about 9 or 10 years old. I always used to wear dresses and white pantyhose to school in 4th and...
    ashlynparker2001 ashlynparker2001 13-15, F Jun 21

    Your Response

    Cancel
    Anytime I'm out in public I'm dressed as a girl. It doesnt have to be a dress or a skirt. I can be wearing skinny jeans, capri's , short shorts or a beach cover-up over my bathing...
    bobbylee111 bobbylee111 41-45, T 5 Responses Jun 21

    Your Response

    Cancel
    I don't know why but I feel like I'm bothering people here with my questions.
    WWYDfan WWYDfan 22-25, M 1 Response Jun 20

    Your Response

    Cancel
    ....because that means no need for cashmere stockings or my thickest Wolfords when I wear dresses to battle the winter climes while commuting or going out. Summer makes me feel...
    bleutifulheart bleutifulheart 41-45, F 2 Responses Jun 20

    Your Response

    Cancel
    I am on vacation far away from the studio, but I still like wearing my dresses and heels., so I bought a few more pretty dresses to wear around the cabin and while driving around...
    Plugslave Plugslave 31-35 8 Responses Jun 20

    Your Response

    Cancel