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I Love Crossdressing For Halloween

Personal Stories, Advice, and Support 180 People

    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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    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 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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    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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    " 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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    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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    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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    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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    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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    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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    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 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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    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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    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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    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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    Related Experiences

    Let's start by explaining I'm a closet cross dresser. I don't just want to be a girl for Halloween I want to pass for one at least with people that don't know me. I know I would...
    Hiddensissy69 Hiddensissy69 26-30, M 4 hrs ago

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    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 4 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 Sep 10

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    I seriously need a girlfriend who will love me for me! Any takers? Now accepting applications! Lol
    rescueme27 rescueme27 18-21, F Sep 18

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    I want to die by my self but I want a man that will love me for me. Someone who want me and only me. Someone who knows what I am mad at then and they know what to do about it! Some...
    Shabz5black Shabz5black 22-25, F 2 Responses 1 day 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 Sep 14

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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 Sep 10

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    It's short and brief, I don't have a boy friend, and I believe love comes itself 😉😉 Looks don't matter for me, I do care about the personalities. I rather fall in love with...
    Martin7470 Martin7470 18-21, M Sep 19

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    My earliest memory of cooking was with my mum and grandmothers as a child, I've always been bought up with home cooked food and watching my family cook, I love it so much I do it...
    Tomm3y Tomm3y 18-21, M 6 days ago

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    My earliest memory of cooking was with my mum and both my grandmothers, I've always been bought up with home cooked meals, family dinners and nice restaurants, I love cooking so...
    Tomm3y Tomm3y 18-21, M 6 days ago

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    It's a great way to show you care for them!
    picklebobble picklebobble 46-50, M 6 days ago

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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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    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 7 Responses Sep 17

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    I went shopping the other day, I was looking for a new shirt to go with a skirt I had. I was in my regular male clothing but I did have my bra on with my inserts but not to...
    mat2Robin43 mat2Robin43 51-55, M 1 Response Sep 23

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    This must be the 1/8 Italian in me, but it's true. Also, not this "Everyone grab a slice" stuff, but the smaller one per person pizza's. Also, yes, I do use a fork.
    LittleStain LittleStain 18-21, F a week ago

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    Fall is Forbidden... you walk away leaving my desire erect reaching for you still with my mind even... my clear longings flee waters lay still... the leaves begin to twist, to...
    PoetryNEmotion PoetryNEmotion 51-55, F 4 Responses 5 days ago

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    The men's underwear section always seems to be in some dark corner of the sales floor. And it's usually empty. But when it's not, I notice that the person, who is shopping there...
    pilotpro pilotpro 22-25, M 2 Responses 22 hrs ago

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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 Sep 13

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    Cooking is a way of expressing myself . I cook daily and my daughter turned to me and said I wish you knew how to cook like McDonalds
    Dancemomisme Dancemomisme 46-50, F 2 Responses Sep 23

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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 Sep 14

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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 Sep 14

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    Wiid -by mc chris, best song ever
    austin1218 austin1218 13-15, M Sep 14

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    If I didn't smoke, I might be a serial killer. Thank Marijuana that youre not dead
    Alylovespuppies Alylovespuppies 18-21, F 2 Responses Sep 15

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    I don't think I would ever find that. I always have to act like somebody else to impress him. When I'm myself it's all weird So I act like somebody else and dress like somebody...
    lorrena19 lorrena19 18-21, F 3 Responses Sep 18

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    Activist4MMJ Activist4MMJ 51-55, M 1 Response 5 days ago

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    Happy October first!!! Time to decorate for Halloween. Muahahaha
    Anngeleyes Anngeleyes 26-30, F 5 Responses 7 hrs 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 Sep 11

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    What should a wheelchair chick be for Halloween? I'm thinking of doing a Mario Kart thing...... Dressing up as Mario and placing balloons behind my wheelchair like the video game...
    perilousindenvers perilousindenvers 18-21, F 4 Responses Sep 20

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    What should I dress as for Halloween? Any ideas....