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I Dressed Up Like a Girl On Halloween

Personal Stories, Advice, and Support 805 People

    this was a wile ago..

    .me and my wife at the time was looking for something to do on Holloween the Casino was having a Halloween costume contest so I told my wife at the time that I wanted to dress up as a girl for Halloween she was not too happy about it but she knew I was a crossdresser and it was...
    buggy6395 buggy6395 36-40 Jul 17

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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 2 Responses Mar 11, 2014

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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 1 Response Nov 1, 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, 2014

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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 2 Responses Nov 30, 2013

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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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    I do this regularly,

    although not last year, hmmm
    Abilohman Abilohman 26-30 1 Response Jan 12, 2014

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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...
    deleted deleted 26-30 5 Responses Sep 11, 2013

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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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    One week until the Halloween party getting

    excited and nervous, can't believe I'm wearing a cheerleader outfit, so glad Les is coming too
    deleted deleted 26-30 Oct 26, 2014

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    I've dressed up as a girl

    for Halloween twice but wish I did it a lot more. The first time, when I was 14 I went with my gf of the time and her friend and her boyfriend. there wasn't much attention paid to me. Just was given some fish nets with some heels that didn't fit right. Also wore a skirt and a...
    crossfitprincess crossfitprincess 22-25, M 5 Responses Jun 21

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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 13 I'd dressed up in my sister's

    things when I was babysitting for her so I knew what I wanted ... it was just a case of how to manage it. I'd be going out as something to a friends party but how could I change into girls clothes for the party and then back before I went home? I couldn't think of anyone to ask...
    amandatrane1 amandatrane1 51-55, T 3 Responses Jul 15

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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 4 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...
    Mistressharley Mistressharley 18-21 4 Responses Nov 29, 2013

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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 6 Responses Sep 27, 2014

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    I'd met and become friends with an older lady

    after buying a few things she had placed for sale. She'd been nervous when I first showed up, some of that due to a previous crossdresser, and made sure her daughter was present for safety. I needed to try a few things on and changed in the washroom. When I came out her...
    amandatrane1 amandatrane1 51-55, T 1 Response Jul 18

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    Back when I was a little younger

    and was dating my 1st wife, she came up with the idea that I should dress as a woman for Halloween. She had a friend of hers that did my makeup and wig, and I shaved my face and legs also. Was a very interesting evening as I was hit on by several different men and even won the...
    Thongme Thongme 41-45, M 3 Responses 3 days ago

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    I saw les for a few mins at lunch today he had

    rugby practice but I walked home with him we never spoke about last night or the very brief kiss this morning, I was thinking the worst but as he stopped to go into his house he said to me to call for him later and that we will just stop in his room on his console. I hope...
    deleted deleted 26-30 Oct 29, 2014

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    So my costume is ready I

    even have a girls wig to wear, I will have to shave my legs and armpits but that's fine. One thing I have thought about but not mentioned to mum ur Les is what underwear should I put on under the cheerleader costume ? I'm thinking just some briefs or full girls knickers...
    deleted deleted 26-30 2 Responses Oct 29, 2014

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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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    I went as a girl on Halloween it was really fun

    and all my friends loved my costume, no one was rude to me and I'm still wearing the costume haha, here's a picture, I was caught sorta off guard when my friend took it though haha, I'm the one on the right. :)
    JulieCakes JulieCakes 16-17, M 3 Responses Nov 1, 2014

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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 5 Responses Oct 29, 2009

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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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    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 61-65, M 3 Responses Oct 31, 2013

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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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    Works party. They mostly weren't surprised to

    see me dressed as a sexy witch. They were surprised at how convincing I looked, and acted. My lecherous, sexist pig of a boss tried to cop a feel saying "dressed like that you must want it". Apart from that it was a marvellous evening.
    Heellover Heellover 36-40, M 7 Responses Nov 1, 2014

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    I'm looking forward to it again this year!

    Thinking of dressing as a bride or Elvira
    0hBrandie 0hBrandie 41-45, M 6 Responses Sep 15, 2014

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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 7 Responses Oct 5, 2012

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    This is it im ready to go out bless mum

    for her hard work and the costume, I could of smiled but hey put some more on later I will smile promise
    deleted deleted 26-30 2 Responses Oct 31, 2014

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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 5 Responses Oct 27, 2012

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    So I saw Les tonight we just stopped at his

    house as weather was rubbish, we played a bit of Xbox and was talking about Friday still skirting around last night, when Les said so are we going out or not ..in private of course? I said if he was sure, he leant over a kissed me it was more of a peck, I kissed him back a long...
    deleted deleted 26-30 Oct 29, 2014

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    I love this time of year.

    Halloween is when all of us crossdressers can openly dress and be the girl of our dreams. The rest of the world may just think were being silly, but we know in our hearts what we are really expressing. I can shop for lingerie all year round without a problem, but this time...
    silkydrawers silkydrawers 46-50 3 Responses Oct 27, 2014

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    I'm going to a Halloween party dressed

    as a cheerleader and my best friend has said he will go as a football player with me. My mum is making the costumes though she is a little bemused as me dressing as a girl but now I'm nervous about it. My mate les said he is nervous too going with me but it's s friend of my...
    deleted deleted 26-30 3 Responses Oct 22, 2014

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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 5 Responses Sep 15, 2014

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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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    So the morning after the party the night before,

    I was so nervous, mum took us over in the car and I had lots of people looking at me when I went in,I had to speak to my aunts who were asking about the costume I was proper nervous. I spoke to my cousins and was dancing, les and my cousins went out the back and was chatting and...
    deleted deleted 26-30 7 Responses Nov 1, 2014

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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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    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...
    Meow1357 Meow1357 18-21, M 1 Response Dec 6, 2013

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    This was my 2nd Halloween I have

    even dressed up for. My first time is in a story I put up here 3 years ago. Since I was with different people this time I wore the same outfit as that 1st time.This picture was taken outside a shopping mall where we just come out from buying drinks and the checkout girl seen us...
    RobynTheBeautiful RobynTheBeautiful 41-45 7 Responses Nov 1, 2014

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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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