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I Halloween Crossdressing

Personal Stories, Advice, and Support 162 People

    Halloween Crossdressing

    Hello everyone. Mostly hope to share this with other wives or girlfriends who have submissive males in their lives. It's getting clsoe to Halloween and there IS preparation time for teaching males how to look their best when done up for Halloween as a woman. Time to start is ASAP...
    deleted deleted
    26-30
    19 Responses May 28, 2013

    So on this day of days

    when you can wear anything you want the best I could do was put on my red cross blood donor t-shirt and point to the cross and say I'm a crossdresser. Sad. But at least I got to tell everyone that I was a crossdresser. Giggle giggle.
    Sharon03 Sharon03
    61-65
    1 Response Oct 31, 2014

    Dressing For Halloween

    My wife and I always enjoy dressing up for halloween and its a great time of year for us to stock up on sexy costumes and outfits. We always go out to bars, clubs, for there halloween parties. One year we dressed up as 2 naughty schoolgirls, wearing white stockings, short...
    pantiescouple pantiescouple
    26-30
    Jun 27, 2013

    You Can Get Away With Soooooooooooo Much More At Halloween

    I love crossdressing for Halloween. For many years now I have attended LIVE Rocky Horror Plays ( not the movie) and rotate costumes using the various female characters. My favorite is the French Maid Magenta ( you can see some of the outfits in my photo album "Alter Ego"). During...
    Flirt4ever Flirt4ever
    66-70, M
    2 Responses Aug 30, 2013

    I was caught by a friends older sister,

    Pam, wearing her cheerleading outfit. I was also wearing her tiny pink panties and a bra I had stuffed. If that wasn't embarrasing enough, I was lying face down with a picture of her in a bikini inches from my face. She screamed when she came in the room. I rolled away...
    bo10 bo10
    36-40, M
    2 Responses Jan 5, 2014

    My "Flirty" Elvira is Coming to Life: A Shortcut to the Toils of Halloween Shopping

    I'm really glad that there is NOT a 12 step program for this Shopping addition , I truly like the high it puts me on. With Halloween coming soon, I decided that this year I would explore a "flirty" ELVIRA. I found a really cute "official" low cut Elvira dress made for male bodies...
    Flirt4ever Flirt4ever
    66-70, M
    2 Responses Sep 11, 2013
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