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I Love Crossdressing For Halloween

Personal Stories, Advice, and Support 178 People

    My Dream Costumes...

    There are a couple of costumes that I would LOVE to wear for Halloween. One of them is a ballerina -- either a tutu and white or pink tights or maybe a leotard with tights and a skirt. The other costume I would love to wear would be a "60's chick". Short, short mini dress...
    driver88 driver88 46-50, M Jun 24, 2012

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    Dressing Up For Halloween

    Several times I have dressed up for halloween and me and my wife even dressed as playmate twins one year, it was fun and we got lots of attention for both guys and woman. We had really short skirts and my wife and I were pretty much showing off our panties and stocking tops the...
    pantiescouple pantiescouple 26-30 1 Response Oct 1, 2012

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    One Halloween At The Office.

    Well first I'll give some background, at work we had a summer swim party several years back. I have long thin legs. They do look like girls' legs. So one of the secretaries I worked with observed that I had ‘girly’ legs. She teased me about how I would look in drag. I...
    JoanneF JoanneF 36-40, F 7 Responses Oct 25, 2010

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    My Wife Crossdressed Me Then Took Me to a Halloween Party.

    About ten years ago we got invited to a last minute halloween party. I said we didn't have any costumes. The people said just improvise. We scrounged through the closets and couldn't find anything, then my wife got an idea. She said why don't I goa as a man and you go as a woman...
    IMACD IMACD 56-60, M 10 Responses Feb 11, 2009

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    Going All-out This Year

    I've crossdressed several times for Halloween, but this year I'm doing something I've never done before. Two friends of mine and I are going to dress up as the Kardashian sisters! I'm going to be Kim. I'm getting a long black wig and will shape my eyebrows to match hers. I...
    jennyla73 jennyla73 36-40, F 4 Responses Sep 21, 2012

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    Did It! (Follow Up To: Tonight’S The Big Night)

    The deed is done. I did it. WE did it. First my wife shaved every body hair I had from the neck down not including my arms. Shower and then perfume she picked out. Next was the see through g-string and fishnet pantyhose. Then the cute little lady bug costume. Finally I put on...
    2muchexp 2muchexp 51-55, M Oct 28, 2013

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    Finally Did It!

    For as long as I can remember, I've always wished that I had the guts to be a girl for halloween. Even in elementary school, I remember there was always at least one person who did it, and it was always a really huge deal and they got all kinds of attention for it, and I was...
    wesleyd wesleyd 22-25 2 Responses Jun 7, 2012

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    Party

    wife has me practicing wearing 4 inch heels for Halloween this year she has me going as a **** in a minidress and she is going as my boyfriend even going to wear her *******
    deleted deleted 26-30 5 Responses Sep 18, 2012

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    Party II

    My wife has been training me for weeks to walk and dance in 4in stillettos. Now its time for the party well last night was, She started to get me ready early at three in the afternoon she made me go to the bedroom where she told me I would do everything she wanted tonight and...
    deleted deleted 26-30 5 Responses Nov 5, 2012

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    " Dressin' Up "

    Every Halloween I wanted to get dressed up as a woman, but my wife at the time wouldn't let me. Now my wife helps me get dressed up for Halloween. It wa so much fun having her help me with my make-up and hair. I had stick-on nails and she painted them for me. When she got done I...
    davis36a davis36a 61-65 2 Responses Jan 23, 2012

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    My Wife went out to get us costumes

    for halloween i told her to suprise me , even tho we both knew it would be girl costumes. she came back with a coupla different costumes. but the 2 that we chose were the same cute glittery dresses. so the transformation was on. got dressed with booty and waist shaper. my big...
    Savannah907 Savannah907 46-50 1 Response Mar 22

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    Transpire?

    Silly idea. Could a cross dressing vampire be called a tranpire? Instead of sucking blood to survive, might a tranpire survive by sucking other fluids
    Officestyle Officestyle 36-40, T 4 Responses Oct 25, 2012

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    Seems To Be......

    the only time of year that I would have some excuse to give some one if I were to be caught, discovered or found dressed up or crossdressed. So every year around Halloween my plan has been to go to a crossdressers store in Toronto to have them do me up in make up, dress up in...
    allyg allyg 41-45 Dec 5, 2010

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    Party III

    Where we left off. Me and my wife are at a holloween party crossdresssed and the girls have cornered me about my sex life in he kitchen. Cindy asks "How big is Julie's **** then". "She has a few" I answer trying to be vague.  Mary chimes in "What is the biggest you take up...
    deleted deleted 26-30 7 Responses Nov 6, 2012

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    Tonight's The Big Night!

    OK tonight is the big night. Tonight I’m going out with my wife to a huge party in Houston. I’ll be in my panties, stockings, petticoat, heels and this cute little lady bug costume. I’ll have in my fake ****. The world will finally see me as the sissy boy I really am.She...
    2muchexp 2muchexp 51-55, M Oct 26, 2013

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    Related Experiences

    I love talking for hours, it makes me feel like I know the person better. It's just a little pathetic over the internet but I wish I could have a face to face conversation half the...
    MiZShortiiE MiZShortiiE 18-21, F 2 Responses Jul 12

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    Hi i am a female still in middle school and i want to crossdress.But how can i hide it? i mean from my elders and maybe classmates...but anyways it would not be hard for me to fit...
    crosdreser123 crosdreser123 18-21, F 2 days ago

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    Dil ne yeh kaha hai dil se My heart calls out to your heart Mohabbat ho gayee hai tum se... I have fallen in love with you Meri jaan mere dilbar mera aitbaar kar lo My...
    AKIDIRANY AKIDIRANY 16-17, F 2 Responses Jul 1

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    Call me, but not if you're really old in your 20's and up 416-661-0123 I'm 15 and love to talk on the phone. I hate texting
    Tasha15Girl Tasha15Girl 13-15, F 6 Responses Jul 3

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    I bought my first pair of hi heels the other day. I took a short walk in them yesterday. I must walk much slower then I would with and other shoes but I love how they make me feel...
    mat2Robin43 mat2Robin43 51-55, M 2 Responses Jul 15

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    I have accepted the fact that falling in love isnt in my cards. I know what you may think your only 19 you have time. But the way I see it time passes very quickly I'll soon be 30...
    Missmonroe95 Missmonroe95 18-21, F Jul 16

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    I have accepted the fact that falling in love isnt in my cards. I know what you may think your only 19 you have time. But the way I see it time passes very quickly I'll soon be 30...
    Missmonroe95 Missmonroe95 18-21, F 2 Responses Jul 16

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    even if i'm not a good cook, i still try my very best to cook from the bottom of my heart (with love) .....Those people who eat my food and says its good are my LOYAL FANS...
    lissomirl lissomirl 22-25, F 2 Responses 3 days ago

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    When I actually do it. That is THEE best time of day. The night wanderers have finally retired for the day, and the day chaos has yet to rise. It's perfect...
    BabyBurd BabyBurd 26-30, F Jul 10

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    I think the best time of the years are holidays something in the air that smells good and feels heart warming cooking for family and friends just make it that much better .
    Fire143 Fire143 22-25, F 2 Responses Jul 13

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    Ok so life moves on next time around this old girl will find someone to show her how much they care and love me, not just from words but actions too , Im not perfect and wouldn't...
    summerspirit summerspirit 46-50, F 6 days ago

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    I love cooking breakfast for the family on Saturday mornings. Pancakes, eggs, bacon. :) I always look forward to it.
    newdayrising newdayrising 36-40, M 2 Responses 6 days ago

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    One of my favorite things to do is cook for or with my boyfriend. I also cook for his family sometimes. I enjoy spending time with them and I appreciate that they allow me to come...
    fairytalesandspiderwebs fairytalesandspiderwebs 18-21, F 6 days ago

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    I saw Bowling for Soup live and met them last Friday, nicest and funniest band ever, absolutely love them and their music.
    xhet xhet 18-21, T 4 days ago

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    He came into my life and changed all the darkness into light. I owe him so much but will never be able to repay him for what he has done for me and how he has changed my life
    jpops jpops 22-25, F Jul 6

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    I purchase all of my Wife's lingerie and sleepwear and I am good at it because she likes and wears what I buy her. She chooses what to wear and she dresses for bed each evening...
    pdqsailor1 pdqsailor1 51-55, M a week ago

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    These past years i have been hurt by guys. I dont know what i have done wrong but all of them cheated on me. :( really hurt right now
    ladyhurt ladyhurt 22-25, F 1 Response Jun 29

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    Gerard Way- Not just A man, my hero Frank Iero- my favourite smile Mikey Way- my serious boy Ray toro- my guitar hero
    DarlinYoullBeOkay DarlinYoullBeOkay 16-17, F Jul 1

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    Call me, but not if you're really old... 901-854-2598 I'm 18 years old
    chris7ina chris7ina 18-21, F Jul 3

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    This one feels very good to pull on...
    LemonSqueezer515 LemonSqueezer515 41-45, M 4 Responses Jul 10

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    I wanna talk on the phone text me ur number n I will call I'm 17 so no old ppl
    idontknow72 idontknow72 16-17, F 2 Responses Jul 14

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    Yeah, my favorite movie. Although I haven't watched the movie in a while.
    heartbroken198 heartbroken198 22-25, M 3 days ago

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    I was supposed to be born on Halloween but I was late. I've always loved everything about Halloween! My apartment is forever decorated for the occasion much to my boyfriend's...
    blueeyedcarolinagirl90 blueeyedcarolinagirl90 22-25, F 2 Responses Jul 16

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    So I got the book,'Maleficent' the other day. And wow. I'm just ad blown away with the book like I am with the movie! It actually introduces Maleficent's mother and father...
    T1997 T1997 16-17, F 1 day ago

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    "If I'm James Dean, You're Audrey Hepburn" [Intro:] Stay for tonight If you want to I can show you What my dreams are made of, as I'm dreaming of your face I've been away for a...
    TurtleKatlynn TurtleKatlynn 16-17, F 2 hrs ago

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    I know Love is risky. You have so much to lose, but with the right person you can be really happy. I did not knew Love was this difficult. I never figured out myself and my...
    Wewerethereinthattime Wewerethereinthattime 18-21, F 7 hrs ago

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    So to start the story, i've not always been really close to all of my cousins, since my parents don't really bring us together, but there's one cousin who's a guy, and one year...
    LilyGlass LilyGlass 13-15, F 1 Response Jun 25

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    But, he did love me for three weeks a year.
    JennaR JennaR 46-50, F 4 Responses Jun 26

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    I know it wasn't that long ago but i just really want someone who cares about more than my looks. I want someone to tell me they love me and actually mean all of me. I want my ex...
    WendyDarlin WendyDarlin 18-21, F 1 Response Jun 26

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    We protect and love those who love us, for we need their love to love us back. It's a beautiful process being done in a beautiful and elegant matter, beautifully.
    MyLady9 MyLady9 46-50, F 1 Response Jun 27

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    I'm young yes.. But does being young necessarily mean you don't know what love is? Ever since I was a little girl i grew up watching the love stories dreaming that one day that...
    autumnforeverme autumnforeverme 13-15, F Jun 27

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    You are not your size or shape your height or your weight You are what you love the something that makes you smile brighter than the sun shines You are your passions how you wish...
    captivateyourlife captivateyourlife 18-21, F Jun 28

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    She did love me for a while. Then she said she didn't. Then she did, but as friends. Then, slowly she drifted away. One intimacy, one level of connection at a time. Shut off. Given...
    anyoldrobert anyoldrobert 51-55, M 1 Response