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I Dressed Up Like a Girl On Halloween

Personal Stories, Advice, and Support 706 People

    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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    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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    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 3 Responses Dec 1, 2011

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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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    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 1 Response Mar 11

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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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    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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    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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    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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    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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    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 13 Responses Mar 25, 2012

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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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    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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    I do this regularly,

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

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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'm looking forward to it again this year!

    Thinking of dressing as a bride or Elvira
    Brandie1960 Brandie1960 41-45, M 5 Responses Sep 15

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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 1 Response Apr 18, 2011

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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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    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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    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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    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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    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 8 Responses Nov 1, 2012

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    So Halloween was coming up

    and my team decided to do a pot luck for our weekly meeting which happened to be on Halloween to celebrate the holiday. I had dressed as a girl once when I was in grade school and had always remembered how much fun it was and how much I liked it. Living alone I had started...
    GirlyMe GirlyMe 46-50 2 Responses 3 days ago

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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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    Not yet, but I want to!

    I don't consider myself passable most days. I would hope that with a little help, I could pull it off a little better.
    JosetteLaRoc JosetteLaRoc 36-40 4 Responses Sep 15

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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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    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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    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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    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 3 Responses Oct 31, 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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    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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    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 4 Responses Nov 29, 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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    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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    Related Experiences

    Yes, I like girls. Although I am bisexual and mostly into men, I still like women also. Now.. I have never actually been with a female before (or with a guy, physically, for that...
    MissClueless MissClueless 16-17, F 3 Responses Sep 13

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    I'm really confused. This story might be a little weird but I want to get some insight. So it started when I had an eating disorder and got obsessed with having a thigh gap. I...
    PrudeAndPrejudice PrudeAndPrejudice 16-17, F 7 Responses Sep 19

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    I like girls that like girls too.
    adav218 adav218 13-15, M 2 Responses Sep 6

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    Hello Ladies and Girls, well I had been battling with myself and trying figure out what is my sexuality for few years, now I am 19 years old and currently have boyfriend. We are...
    xwolverinex xwolverinex 18-21, F 3 Responses Sep 7

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    I'm a real girl who likes girls. But the many people who be hitting me up are not. Like dude you're not fooling anyone. I know you're a man. So if you are a real girl and wanna hit...
    YouDaOne23 YouDaOne23 18-21, F 1 Response Sep 18

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    I don't understand how anybody could not like girls. There's so much to like, ugh girls are perfect.
    thefurthestthing thefurthestthing 18-21, F 4 Responses 4 days ago

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    I am 20 years old . I have been with my girlfriend for almost 2 years now . She's 22. Sighs * I love her to life and this relationship has been no easy task ... The problem is I...
    LadyBug94 LadyBug94 18-21, F 1 Response 22 hrs ago

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    Just bored, and looking to chat with some other girls that like girls.
    FallingRaindrops FallingRaindrops 18-21, F 2 Responses 14 hrs ago

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    I like girls. In my country its kinda illegal to be gay or bisexual and its not by law but the citizen of the country. Jamaica that is. I really like girls and hope one day I will...
    Moniquedavids Moniquedavids 22-25, F 1 Response Sep 3

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    Idk why I like girls more then guys. Maybe because the relationship is more passionate, or sensational. And not as intense
    LifeBeingCereal LifeBeingCereal 18-21, F Sep 5

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    I think I might like girls. I find my self more interested in women each day and might be bi :)
    COcutie21 COcutie21 18-21, F 4 Responses Sep 9

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    I like girls more than boys. I think I'm more on the lesbian side lol
    JusttThatGirl JusttThatGirl 16-17, F 2 Responses Sep 16

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    I like girls more than boys and would love to meet lesbians or bisexuals who are not just acting online. I want a genuine friend who I could easily talk to because they either feel...
    Ryel004F Ryel004F 18-21, F Sep 18

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    Well I do. Mostly because I have really big b00bs and there is nothing wrong with being proud of them.......... I like girls who have big b oops and small ones.
    kddd38 kddd38 26-30, F Sep 18

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    I like girls, but a lot of the times I wish I didn't..
    ConfusedLittleTeenagedGirl ConfusedLittleTeenagedGirl 13-15, F 3 Responses 1 day ago

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    like I said in my other story (funny how they call em stories here wen their not stories, their actualy true :S :L) my mum moves around wiv work soo much dat I neva get to no any 1...
    XXmelanieeXX XXmelanieeXX 13-15, F 1 Response 1 day ago

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    Well yes we like girls but then again I would hope that that is self explanatory
    LSCouple LSCouple 26-30, F 1 Response Sep 7

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