Post
This experience may contain mature content, as flagged by the community. Please click away if you do not want to see this content, or if you are not of age. To report inappropriate content, please email us.

I Love Crossdressing For Halloween

Personal Stories, Advice, and Support 177 People

    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

    Your Response

    Cancel

    " 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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    Related Experiences

    Love shopping for them for sure. I wear panties daily, and I have a few items of women's clothing I wear out in public. Makes me feel cute and sexy!!
    islands115 islands115 46-50, M 3 Responses Jul 29

    Your Response

    Cancel
    Please help decide my slutty Halloween costume: www.misterpoll.com/polls/595069 In exchange, I'll post a story of what comes of it.
    sai7154 sai7154 18-21, T 2 days ago

    Your Response

    Cancel
    I love the way that women's clothing makes me look and feel women have all the best looking clothing
    dantodawn dantodawn 51-55, T 3 Responses Jul 29

    Your Response

    Cancel
    First vehicle ever. 2003 F-150 Supercrew, she's my love.
    Imsobored123 Imsobored123 18-21, M Jul 31

    Your Response

    Cancel
    I love the lyrics and how she sings them. In love.
    marisemarrs marisemarrs 22-25, F Aug 1

    Your Response

    Cancel
    I Speak Of Love i hold the memory of this high hesitant melody this haunting lament i remember you quivering an abyss of blue cerulean an absolute silence dark music rises a warm...
    PoetryNEmotion PoetryNEmotion 51-55, F 3 Responses Aug 12

    Your Response

    Cancel
    I love it when a guy I'm talking to has the guts to call me instead of text me :)
    lunalight21 lunalight21 18-21, F 3 Responses Aug 13

    Your Response

    Cancel
    Meditation begins in the words of masters, adoration begins at humility, concentration begins in the Mystery intuitively percieved, liberation begins by the grace of the Lord...
    Olu3804 Olu3804 36-40, M Aug 2

    Your Response

    Cancel
    Pizza is forever delicous. Where my pizza lovers at? Woop Woop 🙊🙈😋😜😜😜
    TwisterTy TwisterTy 22-25, M 1 Response Aug 8

    Your Response

    Cancel
    well like me and mey bff dr pizza were like yer know just like walking down eh street when he lik turned around and yer know like went for meh lips !!!! it was like shocking like...
    attcia attcia 13-15, F 1 Response Aug 13

    Your Response

    Cancel
    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 5 days ago

    Your Response

    Cancel
    I'm a weirdo. I know. Weirdos need love too
    Alylovespuppies Alylovespuppies 16-17, F 1 Response 3 days ago

    Your Response

    Cancel
    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 1 day ago

    Your Response

    Cancel
    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 1 day ago

    Your Response

    Cancel
    I'm sure most beginning crossdresser were all afraid of being seen dressed but wanted to be seen by someone. Sooner or later that desire will force us to stand by a window or...
    CdKimmi CdKimmi 61-65, M 1 Response Aug 15

    Your Response

    Cancel
    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 5 days ago

    Your Response

    Cancel
    Pizza yes one thing in the world that I would eat over and over and over and over and over again because it's freaking awesome...
    Zalbaar Zalbaar 13-15, M Jul 28

    Your Response

    Cancel
    Provided its quality And not crap. Or overpriced.
    Livyn4pals Livyn4pals 46-50, M 2 Responses Jul 28

    Your Response

    Cancel
    Had pepperoni pizza yesterday
    beautylasts beautylasts 13-15, F 3 Responses Aug 9

    Your Response

    Cancel
    I am in Brooklyn NYC and want to meet local men wearing thongs.
    Nycthonger Nycthonger 36-40, M 1 Response Aug 9

    Your Response

    Cancel
    Food is the edible art, so why not make a **** ton!:D
    tmac7318 tmac7318 16-17, M 1 Response Aug 12

    Your Response

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

    Your Response

    Cancel
    May ALLAH Gave me a happy life
    ApxentMinded ApxentMinded 16-17, M 1 Response Aug 20

    Your Response

    Cancel
    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 6 days ago

    Your Response

    Cancel
    I'm so done..............**** it .
    yassbishh yassbishh 18-21, F 5 Responses 3 days ago

    Your Response

    Cancel
    My favorite halloween costume was when I was little I was meg from Hercules my favorite character from my favorite Disney movie!! :) I hope to be her again for halloween one year!
    mhLILRED mhLILRED 18-21, F Aug 6

    Your Response

    Cancel
    I have been crossdressing for a while now but the first time I was caught was when i was 10. I have a older sister that washed cloths with mine one morning, and she had her pink...
    Fogle3 Fogle3 16-17, M 4 Responses Jul 31

    Your Response

    Cancel
    For Halloween, make your fudge brownies then cover them with chocolate frosting, use Milano cookies for the tombstones(if you're good you can put names on the cookies) and decorate...
    dog211 dog211 56-60, M Jul 30

    Your Response

    Cancel
    R.I.P Jeff Conaway who played my favorite charecter. For halloween one year I dressed up as the pink lady named Marty because I thought she was the prettiest haha. Im a weirdo
    newaccountquinnmac12 newaccountquinnmac12 13-15, F Aug 5

    Your Response

    Cancel
    Kingdom Hearts is one of my favourite games ever. I am trying to find a costume to wear for halloween though it is far off. But in the first game when you fight Leon, you are...
    AccaliaSilverblood AccaliaSilverblood 13-15, F 2 Responses Aug 8

    Your Response

    Cancel
    I am a mature cd and am seeking gurlfriends and admirers to share stories , tips and just be friends. I am so lonely right now mostly because of where i live.I have so many fun...
    susansfun susansfun 51-55, T 13 Responses Aug 14

    Your Response

    Cancel
    I love Michael Jackson. It all started when I was little. About 6 years old. This was 1998. I've heard a lot of Jackson 5 songs in different movies and on the radio and I always...
    DaQueenB92 DaQueenB92 22-25, F 2 Responses Aug 15

    Your Response

    Cancel
    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 3 days ago

    Your Response

    Cancel