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I Love Crossdressing For Halloween

Personal Stories, Advice, and Support 175 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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    " 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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    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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    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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    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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    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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    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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    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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    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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    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 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 9 Responses Feb 11, 2009

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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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    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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    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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    Related Experiences

    I'm a crossdresser, I love wearing women's panties anyone girls like that? :)
    natessecret natessecret 18-21, M 2 Responses 5 days ago

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    Fem Sissy Boy is honestly searching for a masculine and protective boyfriend/husband and treat me as your princess wife! I am TG and would even love to dress for you and if you...
    FemGayBottom FemGayBottom 26-30, T 1 Response Apr 4

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    I've never really tried or paid any attention to guys until this past year when one of my relatives asked me why I was still single... I had no answer besides that I was busy with...
    fgarci04 fgarci04 18-21, F Mar 25

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    Best online shopping for crossdressers is Glamour Boutique! GlamourBoutique.com Please check them out. Tell them Cami highly recommended it!! I LOVE the people at...
    Camilla2014 Camilla2014 46-50, T 1 Response Mar 28

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    I have shoe shopping problems .. I buy all the shoes I want and obsessed with heels , when I was a teenager I used to wear them all the time and after my daughter was born I didn't...
    daisy92 daisy92 18-21, F 3 Responses Apr 2

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    Wabi Sabi: the ancient Japanese idea of illuminating the beauty in imperfection. Love. It’s right up there with air, food, and water as the most necessary of ingredients for...
    Luna47 Luna47 46-50, F 1 Response Apr 6

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    I remember I cooked an actual "romantic style" meal for my best friend whom i loved when I went to her house and I actually did a good job. I cooked her simple stuff like pasta...
    emilesfault emilesfault 16-17, M Apr 7

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    I love to drive for about an hour, explore the city and find new parks, it´s awesome how many new spots you can find while you drive at night.
    Zua95 Zua95 18-21, M Apr 14

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    I wore my first thong on Waikiki Beach. Not being fond of laying around like a beached whale, I walked and jogged the length of the beach. I loved the feel of the sun on my *** and...
    mike92262 mike92262 61-65, M 1 Response 2 days ago

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    It brings out the better and also feels ten times as rewarding (unless you are having some me-time)! Love cooking together with them too
    yxandy yxandy 18-21, F 2 days ago

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    I have a neighbor and she's 8 years old. Her father abuses and neglects her and I feel horrible. So everyday I make her come over and I let her barge at my house and eat because...
    bulimicbixtch49 bulimicbixtch49 13-15, F 5 Responses 2 days ago

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    Tonight is comfort food . Spaghetti with meatballs for the meat eaters and garlic bread , salad and for dessert brownies with homemade gelato .
    Dancemomisme Dancemomisme 46-50, F 2 Responses Mar 24

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    Man stuck in a dress. I had gone dress shopping at a department store wile out of town. I chose four or five dresses to try on. I found the dressing rooms and went in. I tried on...
    mat2Robin43 mat2Robin43 51-55, M 1 Response Mar 27

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    I am looking to go on a foraging adventure. Have you ever gone out for a few days and just survived with what you found?
    odyssey13 odyssey13 36-40, M Mar 27

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    I dont know if this post is still working, but I want/need to share my story. I was married to a guy who was a psycho when I was not even 18. Coming from India, thats like a death...
    kindredspirit75 kindredspirit75 36-40, F 1 Response Apr 5

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    It's great fun to just get in the car and drive with nowhere in mind. I once ended up 400miles away from my house before I stopped for the night and went home in the morning.
    SalinNY SalinNY 46-50, F 4 Responses Apr 14

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    Ford was one of the best. The Blackboard Jungle, The Big Heat, The Violent Men, Gilda and 3:10 to Yuma are essentials. If you like aviation try The Gallant Journey.
    johnny048 johnny048 46-50, M Apr 15

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    I feel so nerdy ! But it's my all time favorite thing ! I'm so interested in it . I find myself thinking about random forensic things during the day . Like what they would do at...
    lilmisslouhoo lilmisslouhoo 13-15, F 1 Response 6 days ago

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    It's extremely agitating comparing myself to others. It's almost an unwanted obsession that ceases to stop. I'm at the breaking point about to tear these walls down. I cannot...
    Allissaxxx Allissaxxx 22-25, F 1 Response Mar 28

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    Seattle pizza sucks! But N.Y.'s pizza rulz!! Btw the pic is of cheese!!
    Awesome5790 Awesome5790 13-15, M 1 Response Mar 28

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    I'm all ready..who's coming with me? #ladiesnight #wednesday
    dreamprinc3ss dreamprinc3ss 31-35, F 5 Responses Apr 2

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    Just received a gift card to DSW! I know where my money is running off to! 👠👠👠👠👠👠❤️❤️❤️❤️❤️
    Zacarabear Zacarabear 18-21, F 1 Response Apr 2

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    I picked up my 2nd pair of 40th anniversary L'eggs pantyhose in the Limited Edition Classic 'EGG' packaging on Sat. have been trying to find what colors they are coming in. So...
    krisyca krisyca 41-45, T 6 Responses Apr 7

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    Gotta eat them all!! Pizzamon!!! :3
    Oti91 Oti91 22-25, M 1 Response Apr 10

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    It is such a stress reliever!
    kelgurl kelgurl 31-35, F 1 Response Apr 11

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    It's what I miss most about cable:/
    holdenco holdenco 31-35, F 6 days ago

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    I love crossdressing for sex with men. I like feeling as much as a girl as possible. I love thongs and bras, and all womens sexy clothing.
    islutmyself54 islutmyself54 26-30, M 1 Response a week ago

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    Hi. Im a male 18 at college. Ive been crossdressing for a while but am looking for a female to talk with about it and whatever..message me on here
    Zxi19 Zxi19 18-21, M Mar 30

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    totally gonna be elsa for halloween/comic con!! going to have to make my own dress though/:
    heartslob heartslob 16-17, F 1 Response Apr 15

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    My name is Laurent ACHER 41 years old, French mother tongue I'm single , no children, Straight virgin height : 1.85 m, Weight: 85 Kg normal pace brown hair, brown...
    steack2 steack2 41-45, M 4 hrs ago

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    Well as the title says, I'm afraid I will never find anyone to really love me, I know I'm very young and all but most of my friends already had their first kiss, their first...
    IHateUsernames0 IHateUsernames0 13-15, M 4 Responses 2 hrs ago

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    I found the guy that loves me for my personality and not just my body. I found the guy who loves the idea of spending a Friday night in with me, watching movies. I found the guy...
    krorenae krorenae 18-21, F 2 Responses Mar 25

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    I Love vacations near the sea as sea atract me,love swimming love bikini,love Greece for this.
    blackweirdcat blackweirdcat 46-50, F Apr 1

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    I've always loved to look up at the night sky, I love seeing the moon, and the stars illuminate the world around me. i don't love them for their beauty but for reminding me of how...
    Krysk Krysk 13-15, M 1 Response Mar 24

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    I met a girl 2-3 years ago in mcdonalds she was beautiful, a real piece of work. The most amazing young woman i've ever seen. Snake-bite piercings jet black hair comepletely...
    Coolbeans10 Coolbeans10 16-17, M Mar 24

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    <3 regardless of what I deal with one a daily basis. Somebody who's gonna love me for me. I get told I'm a great, sweet, amazing girl who deserves the best but all I get a...
    93rp 93rp 18-21, F 1 Response Mar 24

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    I'm overweight and my self confidence is low but I don't hate my body. I'm 5'8" and weigh 375 lbs I've had this question stuck on my mind a lot lately because I've noticed that all...
    fgarci04 fgarci04 18-21, F 2 Responses Mar 24

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