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I Dressed Up Like a Girl On Halloween

Personal Stories, Advice, and Support 674 People

    So Did I

    The party was held on the weekend after Halloween.This group that held the party is very new to me that I found on the internet and the first thing I seen was a Halloween party coming up and I joined the group right away and a bit later I had met two girls a about 3 weeks ago...
    RobynTheBeautiful RobynTheBeautiful 41-45 2 Responses Dec 1, 2011

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    Not Such A Big Deal

    I often go dressed up as a girl, and also love it. But, then again, I often wear skirts and dresses in the summer, not to look like a girl, but just because they are more comfortable, so the Halloween thing is not such a big deal for me. A year ago I was at a Halloween dance in...
    davyjo davyjo 51-55, M Jan 21, 2013

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    Dancing The Night A Way

    A couple of year ago my girlfriend talked me into dressing as a girl for halloween. I was a bit nervous at first but the whole thing turned out to be a lot of fun and I was surprised at how good looking I turned out. I went over to my girlfriends apartment about 3 in the...
    deleted deleted 26-30 6 Responses Oct 29, 2009

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    I Really Want Too

    im hoping that i can this year. its been a really long time since i even did anything for halloween. id really love be able to go out dressed up because of the thrill of it an knowin no one will say anything about it. i just hope my girlfriend will give me the okay to do it.
    glasscitycd90 glasscitycd90 22-25 4 Responses Jul 24, 2012

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    Dressing Up At Work On Halloween - Lost my carreer.

    Been dressing up for years. But I always want to push it more. Been out shopping, to the mall, various walks all over, running errands, but for 15 years been dying to dress up at work where everyone knew me. Even some family. I mean it was Halloween. A few signs had been put up...
    dawn3000gt dawn3000gt 36-40, T 6 Responses Nov 6, 2013

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    School Night...

    unfortunately for me, halloween is a school night for me. I don't mean it's a night before I have school the next day, I mean I have school that night. BUT I've decided that I'm going to crossdress to school that night. It'll be a different experience for me, I've been out and...
    STLCD STLCD 22-25, M 4 Responses Oct 26, 2012

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    I'd like to hear about it

    and see some pictures. Message me for my email.
    ar29605 ar29605 22-25 1 Response Feb 9

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    I was dared to be a girl

    for Halloween this year. My hair grew a few inches longer since summer and got a new layered hairstyle. One of my friends let me borrow her skirt and crop top. I wore a white tank top underneath. She shaved a little my eyebrow to feminize it. Had eyeliner added, red lipstick...
    meowrawrs279 meowrawrs279 18-21, M Dec 6, 2013

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    Halloween

    For halloween I wore my black leggings and uggs. I also wore a bra and a pink top with flowers
    redleg19 redleg19 16-17, T 3 Responses Nov 30, 2013

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    When I Was 8

     i had on a pink baby dress,a diaper,pink stockings,a bow in my hair.and i went around like that.and people actually thought i was a girl.and would say isn`t she a cuttie.when i got home i stayed dressed like that for the rest of the night untill bed time.
    mamaslittlebaby mamaslittlebaby 18-21, M 1 Response Aug 27, 2009

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    I Really Want To

    I have a very hot younger co-worker in my office building that want to dress me as a passable woman for Halloween. The two things holding me back is my wife does NOT like my dressing and I haven't told anyone about liking to dress fem. I haven't told her that I would love to, but...
    thisismeisthisyou thisismeisthisyou 41-45, M Oct 14, 2012

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    Halloween At My Local

    I dressed up in a long black dress, high heels, wig and fishnet tights for halloween. I went out with my wife to my local dressed up like that. It was such a thrill being able to dress as I like and get away with it in public. Cant wait for the next excuse !
    welshtv welshtv 36-40 1 Response Jan 29, 2011

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    Dances Are Fun

    Whenever I know there will be dancing at a Halloween party I always wear the shortest frilliest miniskirt I have. Now I won't dance with guys, but many girls get a kick out of "trading parts" while dancing, so I have sort of learned to follow her without stepping on her toes...
    davyjo davyjo 51-55, M Jan 21, 2013

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    After Years Of Waiting, I Finally Did I!!!

    I'm happy to say that not only did I dress up on halloween but, I actually went out in public while still dressed up!!! I'll start from the beginning, I work nights as package handler (please keep the minds out of the gutter people) at a near by FedEx so I already knew I probably...
    glasscitycd90 glasscitycd90 22-25 Nov 1, 2012

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    I let a girl dress me fom head to toe

    as a french maid one year. Very emberessing at first but once i got some liquor in me i jad fun with it. The nail polish was a ***** to get off. Hahaha. There was of course alot more to this story. So much lace and lipstick. But i really need to b drunk or have a girl super...
    staggershine staggershine 31-35, M 2 Responses 6 days ago

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    This Year I Probably Will

    I never really thought about the possibility because I've always thought that I'd want to go out a few times before I attempt halloween. now that I've been out a few times, and likely will several times between now and halloween I'm probably going to do it this year. Of course I...
    STLCD STLCD 22-25, M 3 Responses Jul 20, 2012

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    My First Halloween Dressed As A Girl

    Halloween has always been one of my favorite holidays. I just love dressing up in costume and have often gone out en femme. Afterall, it is the one day that no one questions you about being in drag. I was married at the time. My wife knew of my crossdressing interests, but I...
    jennyla73 jennyla73 36-40, F 12 Responses Mar 25, 2012

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    My sister had this cheerleading uniform (like,

    actual cheerleading uniform, not a crappy overpriced Halloween store costume, but a real overpriced costume that a real girl would wear on a real football field). I decided to, a few years ago, see if I could fit into it. I did. I then decided to use it as my Halloween costume...
    tiffanyjoxd1989 tiffanyjoxd1989 22-25, T Mar 11

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    I Did This Year

    A young girl too. I think her name is Alice and her curiosity gets her into trouble :)Like chasing rabbits and such.
    babybearjean babybearjean 56-60, M 2 Responses Oct 31, 2013

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    It's Getting Close

    ? Girls , I need some ideals for this year and it is getting close .What chick can i dress like ? ( the outfit must in vole hose , longsocks or tights ?? Please help me look hot these halloween
    shoesred shoesred 51-55 8 Responses Oct 5, 2012

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    Drama

    Hello everyone. My middle school offers drama class to students who choose it. I did and the part I got in a play happens to be Miss Muffit. This is the perfect role for me as I am a crossdresser and with this I get to do it in public with out arising any suspicion. Also the...
    DevinTimes2 DevinTimes2 18-21, M Nov 9, 2011

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    Every Single Year

    ever since i was 15 3 years ago i have dressed like a girl for halloween the first year wasnt that good i looked like a guy wearing a dress but the second year i got a girlfriend and she had me go as a hooker she even did my makeup it was a big hit but the 3rd year i did it i...
    loverofboobs loverofboobs 18-21 3 Responses Nov 29, 2013

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    Dressed As A Woman Again For Halloween

    I spent my afternoon getting ready for a Halloween party. My wife suggested I dress as a sexy secretary. So we went out and bought a nice black skirt, blazer and a teal top. So I got dressed in my bra, forms and padded panties, put on my pantyhose and my new outfit. I then did my...
    JoanneF JoanneF 36-40, F 9 Responses Nov 1, 2012

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    First Time. Trying It Again.

    When I was younger, in grade 5, 8 years old. i had decided I want to be a girl for Halloween. Telling my mom wasn't easy, but she approved, at this point in my life I knew I had wanted to do feminine activities, but had never had the chance, nor was I brave enough. I had my moms...
    FemmeLove FemmeLove 22-25, M 1 Response Sep 10, 2013

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    Katy Perry Tonight On Bourbon St. - First Time Out!

    So I have my sexy outfit, heels, panties (for the lucky viewers), blue wig, fishnets.... I can't wait... bit I am nervous! first time in public - it is halloween and I'm going out w gf so... any tips?
    MandiLi MandiLi 31-35, T 6 Responses Oct 27, 2012

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    Any advice?: Dressing As Katy Perry On Bourbon St!!!!! W Gf

    I can't wait the full story to come... My first time dressing in public! So I'm starting to get nervous... and heard that a family memeber may be in the same area for a party... this is my shot! I have my wig, sexy outfit, heels... my mom is going to be in same area, may or may...
    MandiLi MandiLi 31-35, T 4 Responses Oct 23, 2012

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    This will be my last halloween to dress up.

    Im going to go out on top i want to pass a a woman.This is what i got so far any opinions? 
    jtrain jtrain 31-35, M 2 Responses Jun 20

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    Yoga As A Girl

    So this year a few weeks before Halloween some of friends from yoga and I were talking about our Halloween costumes, and I mentioned I was going as a girl. well two of the girls started in on how I should they would want to see that and that I should wear my costume to class on...
    littlefoxlost littlefoxlost 31-35 5 Responses Nov 30, 2011

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    Best Halloween EVAR!

    last year a month before halloween me and my girlfriend were talking about halloween and who we should dress up as but we couldnt agree on one idea so we said just to put ideas into a hat and thats how we will choose i really wanted to see my girlfriend dressed super sexy so i...
    sissyslut64 sissyslut64 18-21, M 4 Responses Sep 11, 2013

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    My First Time...

    My first time dressed as a girl was on Halloween. It was the early 70's, and my Mom and aunt thought it would be cute to dress my cousin and I as girl for Halloween. We wore the latest 70's fashion -- we each wore turtleneck bodysuits, pantyhose, mini skirts, go go boots, and...
    driver88 driver88 46-50, M 1 Response Jul 21, 2010

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    Cindy Brady

    I want to dress up as Cindy Brady this Halloween , just can't decide which hairstyle to pick.
    PrettyLittleStacy PrettyLittleStacy 18-21, M 2 Responses Oct 9, 2013

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    When I Was 9

    I was a doll. I had a blast. I wasn't worried I that might be gay at all. :P
    ThisIsNotForYou ThisIsNotForYou 13-15, M 5 Responses Jan 10, 2012

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    A Witch

    Not a sexy witch, more a green faced old hag, but it was still convincing enough to fool 3 of my oldest friends. One person at the party could not be convinced, without me exposing myself, that I was actually a guy. It was a great night!
    Heellover Heellover 36-40, M 1 Response May 6, 2012

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    Every Halloween

    I grew up in a family which didn't have a lot of money, so mom didn't go out and buy me expwensive costumes for halloween. My cousin Jane andI usually swapped outfits for trick or treating. I'd wear one of her dresses and she would qwear something of mine. For instance I remember...
    jere51 jere51 51-55, M Apr 18, 2011

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    I do this regularly,

    although not last year, hmmm
    Abilohman Abilohman 26-30 1 Response Jan 12

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    Related Experiences

    So back when I was younger, I would always play with girls more often than boys (as any typical girl would). Every now and then I would be hanging out with a girl friend or...
    ShyBi416 ShyBi416 16-17, F 4 Responses Jun 30

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    I like boys and I like girls. I have an amazing boyfriend whom I love with all my heart. I couldn't imagine spending my life with someone else. But I also love girls. I am really...
    Nemessie Nemessie 22-25, F 3 Responses a week ago

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    when i was a young girl about 8 my baby sitter use to come ova in do little things to me as i got older about 11 or 12 and my next door neighbor liked me and she came ova my house...
    neababy1987 neababy1987 26-30, F 1 Response Jun 30

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    Ever since I was a little girl I was always attracted to other girls. When I was little I'd play house and I would offer to be the dad just so I could have a "Wife". As I grew up I...
    TheGirlFromJupiter TheGirlFromJupiter 18-21, F 4 Responses Jul 4

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    I am a lesbian. Where I live you really can't speak about it. I've known I liked girls for as long as I could remember and I remember when my female friends would talk about boys...
    Alexandra987 Alexandra987 18-21 3 Responses Jul 7

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    I have been dabbling between girls and guys for a while.I like guys but I am kinda more into girls,I personally feel like girls just lie less and are genuine,at least in my case...
    jesikahluv jesikahluv 18-21, F 4 Responses a week ago

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    So I became friends with this girl this year and then one day I was messing around and saying I was gonna go lesbian. Well we kissed and it was amazing. And now we are like dating...
    mld95 mld95 18-21, F 1 day ago

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    I think I first realized my like for other girls when I watched lesbian **** for the first time. When I found myself getting turned on and intrigued, I turned it off and refused to...
    kittybabe100 kittybabe100 16-17, F 3 Responses 17 hrs ago

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    I've never been with a girl. But I've always known I like girls. I thought college would finally give me the experience I've been looking for, but it hasn't yet :( I'm easy to get...
    J94RoseRed J94RoseRed 18-21, F 2 Responses Jun 30

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    I've always liked girls, I've never had feelings for a guy. People find it strange because I usually spend most of my time around guys when I go out & never with girls. I guess it...
    KMargatroid KMargatroid 16-17, F 4 Responses Jul 7

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    So.... I know for a fact that I like girls..... I mean, how could you NOT like girls?? They are pretty, they smell nice, they can be sweet and kind, and they kinda understand you...
    Brokenglassapple Brokenglassapple 16-17, F 1 Response Jul 13

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    I am a girls and I like girls I am a lesbian Anyone girl want to have fun
    emma872 emma872 26-30, F 3 Responses Jul 18

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    Man Idk but Ima girl who likes girls. Ever since childhood, I am gayer than Light Yagami or Light Imagay. Man, I even kissed a girls uh you know Ima gayiiiiiii. HAHAHA!!!! Trolling...
    GothicLunar GothicLunar 13-15, M 3 Responses Jul 20

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    So I realised that I really like my friend a few weeks ago. I already knew I liked girls and I came out to her, I trust her, with being bisexual a few months ago. I was so scared...
    sfairy27 sfairy27 13-15, F 4 days ago

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    Girls actually listen and get it, they know what another girl wants, which makes it a great match. I like girls although I like guys as well.
    jesikahluv jesikahluv 18-21, F 1 Response 4 days ago

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    I am a girl who likes girls that is seriously lacking in the friends "girls who like girls" department. Hopefully I can make some :D ah warning personality wise o.o I can be a...
    MaryLiz94 MaryLiz94 18-21, F 3 Responses 1 day ago

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