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I Love Crossdressing For Halloween

Personal Stories, Advice, and Support 216 People

    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
    4 Responses Nov 5, 2012

    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
    Dec 5, 2010

    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
    3 Responses Sep 21, 2012

    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


    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
    2 Responses Oct 25, 2012


    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
    5 Responses Sep 18, 2012

    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
    1 Response Oct 1, 2012

    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
    5 Responses Nov 6, 2012

    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
    3 Responses Mar 22, 2014

    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
    4 Responses Oct 25, 2010

    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

    dragqueenpa dragqueenpa
    61-65, M
    Nov 2, 2015

    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

    " 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
    2 Responses Jan 23, 2012

    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
    26-30, M
    2 Responses Jun 7, 2012
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