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I Love Crossdressing For Halloween

Personal Stories, Advice, and Support 179 People

    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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    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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    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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    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 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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    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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    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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    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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    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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    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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    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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    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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    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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    " 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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    Related Experiences

    My husband wants to go to vegas for halloween, so that I can wear a slutty costume and fit in with the rest of the girls. I love the idea.
    curiousbrenda69 curiousbrenda69 26-30, F 3 Responses Sep 8

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    Hello, so, I want to be something Minecraft related for Halloween, but I can't decide what I want to be. I looked into making a creeper costume, but it seems really, really, really...
    H20Lover342 H20Lover342 13-15 a week ago

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    I've narrowed it down to ten choices for my Halloween costume. Please cast your vote for my slutty getup. http://www.misterpoll.com/polls/596003
    sai7154 sai7154 18-21, T 1 Response 3 days ago

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    Musings of a Poetess... your eyes turned my tide my ears deciphered rumours of your arrival my loneliness was shrouded deeply, neatly, layer pon layer... I shall report our kisses...
    PoetryNEmotion PoetryNEmotion 51-55, F 2 Responses 9 hrs ago

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    I miss having someone to hug for a long time Someone who would hold me after we got in a fight someone who would let me talk to forever about my problems and then tell me what I...
    Jessekat123 Jessekat123 16-17, F 2 Responses 3 hrs ago

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    A great man once said, It matters not who you love, where you love, why you love, when you love or how you love, it matters only that you love...
    poppagee poppagee 16-17, F Sep 6

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    6 months with you and it feels like im the only one in the relationship, its like im only your "gf" when you need something or wen u need attention. I live my life for you and do...
    rescueme27 rescueme27 18-21, F Sep 9

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    I like girls, but I rather be single. They only hurt you at the end.... Plus too controlling. Fell in love ones and I hope I never do again. Biggest mistake I've ever done...
    txblank91 txblank91 22-25, F 1 Response a week ago

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    Most days, some sick, twisted part of me compels me to come downstairs during break to hang out with people that I liked at some point in time. Those days are the ones that make me...
    raindrop19 raindrop19 31-35, F 1 Response Aug 22

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    I will fall in love with you for who you are not what you look like, a kind heart that treats me right is what I ask for <3
    NoraWilliams NoraWilliams 13-15, F Aug 22

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    I'm a weirdo. I know. Weirdos need love too
    Alylovespuppies Alylovespuppies 16-17, F 1 Response Aug 24

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    To be honest I have always been a good girl. Good grades, a good person, always trying to do what I thought was right. But then I met him. Not exactly in the way most people meet...
    rachel13124 rachel13124 16-17, F Aug 26

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    I had so many tomatoes from the garden, heirlooms, San Marzanos, and cherry's. Decided to make a sauce from scratch. I've always doctored up good canned ones. This is my second...
    SlickFX SlickFX 31-35, M Aug 27

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    From before I knew you Through the Ups and Downs I forgive you as I hope you forgive me I will always be with you No matter where I am or where you are You are my beginning and...
    Jacques0041 Jacques0041 46-50, M 1 Response Sep 6

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    I was going to try to go trick or treating but I figured since I'm kinda pushing it (and I can't have candy) I decided not to. My friend is having a party and I might go but idk...
    KittyKatLuvsYhu KittyKatLuvsYhu 13-15, F 5 Responses Sep 9

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    If a girl made me do this.. I'd be in heaven!
    CoryCD CoryCD 18-21, M 1 Response 3 days ago

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    My girl 😊 still working on her ❤️
    MissSubaru MissSubaru 26-30, F 1 Response Aug 18

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    May ALLAH Gave me a happy life
    ApxentMinded ApxentMinded 16-17, M 2 Responses Aug 20

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    I really do! You can really get to know a person by their voice. By the words they use. If anyone ever wants to talk on the phone, message me! :)
    Kaytee120 Kaytee120 18-21, F 2 Responses Aug 21

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    I'm so done..............**** it .
    yassbishh yassbishh 18-21, F 5 Responses Aug 24

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    A four wheel drive ,loud music on a never ending road!
    niza33 niza33 31-35, F 1 Response Aug 28

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    you land so soon cz il it been too long i get stop the tears and stay on my feet and be strong i see you on my dreams when i wake up your gonne i felt so weak to god we all belong...
    Jakies Jakies 18-21, M Sep 5

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    Anyone wanna talk on the phone? Have to live in the U.S., don't have an international calling plan
    abercrombie99 abercrombie99 13-15, M Sep 5

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    Out of stocks :( i miss the hiiigh! Here's a cat doing yoga.
    couplehotlove couplehotlove 26-30, F 3 days ago

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    It's actually a very beautiful place. You people should go there if you haven't yet.
    JohnBobMac JohnBobMac 16-17, T 1 Response 3 days ago

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    Wiid -by mc chris, best song ever
    austin1218 austin1218 13-15, M 3 days ago

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    If I didn't smoke, I might be a serial killer. Thank Marijuana that youre not dead
    Alylovespuppies Alylovespuppies 16-17, F 2 Responses 2 days ago

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    I really hope I can get someone to go do something with me for Halloween, like dress up and go to a haunted house or something dumb like that. I've never really done anything even...
    graveyardghosty graveyardghosty 18-21, F Sep 8

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    I love crossdressing the feel of a sexy bra and thong are the best and sexy mini skirt
    harley80cu harley80cu 41-45, M 2 Responses 6 days ago

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    The SmartLipo Triplex that combines three different wavelengths which include 1064nm, 1320 nm and 1440nm. The 1440nm wavelength is added to your Triplex as a result of its potent...
    William162d6ol9 William162d6ol9 31-35, M 1 Response Aug 25

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    LET ME BE .... Let me be the one that earns your love .. Let me be the one to end all tears of broken promises .. Let me be the one to hold you in my arms .. Let me be the...
    mintybear2 mintybear2 41-45, F 2 Responses 20 hrs ago

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    I have been in love twice, and both times have crushed my soul. Yet I continue to pursue it. I spend all my time searching for someone who loves me for me.
    msharleenquinzel msharleenquinzel 18-21, F 4 Responses 11 hrs ago

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    Head Over Feet - Alanis Morissette (Acoustic) https://www.youtube.com/watch?v=6R5bRw6kkDY "...You've already won me over in spite of me And don't be alarmed if I fall head over...
    Cherbelle Cherbelle 41-45, F 1 Response 7 hrs ago

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    How hard is it to find someone who loves you for you and not just sex? Ugh, people are just.. Bleh right now.
    Abbyy99 Abbyy99 13-15, F 2 Responses