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Halloween dressup

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It's Halloween. You're going to a costume party with a lady friend, wife, girlfriend,etc. If she asks to dress you up as a sexy woman, would you agree? How far would you take it?
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If the wife asked I would get dressed as a woman and go to a Halloween party. I think it would be fun
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I know this is an 'Ask The Guys' thread, but I just had to share this.
When I was in high school I had a guy friend who dressed up as a woman for Halloween. Not really a big deal, except that he made a better looking woman that guy. LOL! I just had to share that.
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I would have to go as "The Bearded Lady," but yeah I would do it.
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Would prefer a night of Haloween UNdressup...
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i would have no problem dressing up as a matter of fact i would love it
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^ I would never have guessed! lol

Done it before and would do it again. A few months ago I lost a bet and went to some nightclubs in a dress, wig, fishnets, boots, make-up etc... Couldn't exactly tuck it up into the waist of my pants if required.. :s
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Sure why not i think it would be fun and i would take it all the way
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God yes in a heart beat...might take a while for the right lingerie to where but l'd so love to go
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Duh, check my profile....IN A HEARTBEAT!!!!!!!!!!!!!!!!!!!!!
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I would LOVE it!!!!!
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Of course. In fact I already have my stripper outfit for a Halloween party I'm going to.
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Thanks to everyone who posted a reply. This was the first forum post I started.

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Yes Id let her dress me up enfemme.I have been totally feminised by girlfriends for parties lots of times from something mild to wild like a hooker or bride in the satin lace gown and all
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I'm a closeted crossdresser so yes!

In fact I went to a fancy dress party a few weeks ago which was a gender swap theme. I had to be careful so as to appear not too keen! My gf insisted I make an effort though so my full outfit was dress, satin thong, suspenders,bra, lace top stockings, high heels, wig and make up.
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100% jump to do it just just to mind fuck people doing it........
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i would not mind as long at she dressed me up tastefully. no offence to cd's and treanny's but i dont want to look like a transexual. i would want to look as sexy a possible.
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It would depend mostly on who else would be at the party, but probably yes.
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I dressed up several times as a women. Ive gone as far as shaving my face , my legs and my under arms. I paid for doing the shaving when it grew back but I had a lot of fun. All the women would reach under my skirts and play with my ass and my balls and aslo the dick. It does get a little cold though when you out side in the fall.
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Hell yea I would. That would be fun. It wouldn't be a mindfuck to anyone, it's Halloween. If I dressed like that for work, that would mind fuck people. lol



When the debate is lost, slander becomes the tool of the loser. Socrates
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Quote by lafayettemister
Hell yea I would. That would be fun. It wouldn't be a mindfuck to anyone, it's Halloween. If I dressed like that for work, that would mind fuck people. lol


Certainly never at work...right...

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Quote by Curlygirly


Certainly never at work...right...



it all depends on relationships at work if i were working with lot of ladies yes but with pigheaded males like i do i couldnt
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love it
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It would have to be more than just a sexy lady. Maybe if it were a character that made it funny, that would work. Princess Leia or some other iconic female character that made it more into a gag than just cross dressing would be fine.
"I saw the angel in the marble and carved until I set her free." -Michelangelo


Please Enjoy: The Beach, The Workout, The Hike
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Without a second thought I would do it!
Active Ink Slinger
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Well, my husband will be wearing a blue latex pleated mini skirt, a white satin tie top, and thigh high boots. Lots of cheap bling jewlery and makeup along with a bright pink wig , cut in a "bob" cut.
It was my idea.
"When its too kinky for everybody else, its just gettin' good for me."
(Kinky Freedman)
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Sure I would. I've already dressed as a woman on previous Halloweens.
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Yes I would havent done it but then again I would make one fugly broad