Hot sexy underwear and a half million dollars?
Hell yeah.
Bleah, didnt read the op. i voted male/yes, but not for that little money.
What, like flannel?
Nothing’s stopping you. Management is not pervy enough to make you drop trou–er, skirt–in the random inspections. Probably the inspection agent just pops into your workplace/favorite coffeehouse/etc without warning, makes sure you’re wearing a skirt or dress, shrugs, & leaves.
That’s between 15 and 20 times my current annual income; I’d be insane to not take it.
No, but you might maybe could talk me into wearing a kilt for a year for 10% of the payout.
For one thing, I doubt it would be easy to locate women’s clothing that would fit me. For another, men wearing women’s clothing is only good for one thing, comedy, and I already look funny enough. Finally, I might accidentally run afoul of the “never go outside” police, depending on when and how frequently the “random” checkups occur – this clause kinda screws over the homebodies.
You gotta tell us the story behind that one.
I’d take this deal in a second–then again I’m a crossdresser:). The big problem is that I work at a lab, and I can count on my fingers the number of times one of my female coworkers has worn a dress or skirt in the last five years.
Probably, if I could get some kind of promise from my employer not to fire me over it.
Shoot I’d do it for 50k without a second thought. For 500k I’d skip to the bank in my skirt.
nm
Heck, I’d do it for a helluva lot less than $500,000. Take the damn infernal killer pointytoes shoes out of the mix and I’d almost do it on a lark for free. Disclaimer: I wear skirts several times a year as it is.
Sure. I’d make like Corporal Klinger for a year for $500,000.
Yeah, no problem. Where do I sign up?
$500,000? $10,000 a month?
I’d go to work in a French Maid’s uniform (assuming I wouldn’t be fired for any part of this, of course). That would be a huge financial boost.
I haven’t been brave enough to ask (also, it seems like it would be kinda rude)! The dude wears a dress/skirt, heels, and a purse. Fashionably matched, as best I can tell. But he has a man’s haircut and keeps a short beard. He’s been at it for well over a year, so if he lost a bet it’s a pretty big one! I guess he just takes his crossdressing seriously. At this point, he grabs my attention less than high-water-pants guy, emergency-orange-shirt guy, the-twins-who-also-wear-identical-clothing, or the-polish-crowd-who-all-wear-shorts-even-when-it’s-raining.
Come to think of it, Tom Hanks did that to earn an honest paycheck, and went on to win Oscars; Michael Caine, likewise; Jack Lemmon did it, Dustin Hoffman did it, Robin Williams did it, Cary Grant did it, Alec Guinness did it, Jeff Bridges did it, and Heath Ledger did it, and paychecks and Oscars ensued.
That’s not actually my point, though. Instead, I’m now picturing someone winning the bet by just paying homage to cross-dressing on film: walking around town like Mrs Doubtfire, or making the rounds as Tootsie, or slapping on plenty of Joker makeup complete with nurse’s uniform…
I wouldn’t wear “traditional women’s garb” for a year and I am a woman!
Okay, I probably would for decent money, but men, save yourselves! 
Skald, old man, I say… what is it with you and the Cymry?
Did a Welsh lass spurn your affections one fine evening in Carmarthen?
Is it that you break out at the touch of lanolin?
Perhaps you just don’t like the smell of boiling leeks in the fine autumnal breeze.
You seem like such a well-balanced chap. Do tell what has riled you against those who dwell among the Cambrian hills, if you will.
For me, that would be the best part. My lovely and talented female spouse mostly dresses like a lumberjack. I .on the otherhand, am always overheated, and would prolly wear skirts and sandals all year. I’m thinking that with my shaved head I could rock a Sinéad O’Conner look.
Sign me up. I’ll also wear a sign that says “I’m getting $500K to dress like this”. And, being self employed, I have no doubt that my boss will allow me an extended sabbatical. Perhaps to write that novel I’ve started half a dozen times.