Any advice to help me win a bet to dress up as a woman for a whole week?

I have taken this bet but I need advice about how to win it! All suggestions welcome, I need to be as glamorous as I can!





On halloween I won a bet by dressing up in drag for a costume party with people from work. Some of the women there bet me I could not last a night in drag because the clothes and shoes would be too uncomfortable. Actually it was no problem! But now they have offered to double the bet if I take a new challenge. They said one night was too easy and I couldn't last a whole week. There is a Christmas costume party on a Friday night in a few weeks. To win the new bet I would have to go in drag to that party and for work for the whole week before. The boss said it is OK as long as I look convincing as a woman at work.





So I would have to wear a business suit (with a short skirt and high heels) for a week and a party dress again, and they would give me a complete makeover for the week - hair, make up, fake nails, shaved legs, the works. I am up for laughs and it would be funny to win and prove them all wrong. So I need advice on how to look good and how to last the week, especially in those shoes, I managed walking around in 4 inch stilettos for one night but a whole week could be hard! And for the party I need to find an awesome dress that will look stunning, but not cost too much, any ideas?Any advice to help me win a bet to dress up as a woman for a whole week?
lol good luck on that one I never wear heels. I'm surprised your boss was ok with that for just a bet, alot of places don't accept that even for transexuals. I'm guessing you like dressing that way and are using that as an excuse. This is the LGBT section feel free to admit the truth lol.Any advice to help me win a bet to dress up as a woman for a whole week?
Yr best bet is a constant shave and make up-well done. You don't need much, the basics are eyeliner, mascara, lipstick and in your case foundation to hide the stubble. If you really wanna go for it I strongly advise plucking the eyebrows if they're thicker than half a cm.


Not every woman wears 4 inch stilletoes, go for flat pumps with tight trousers (ouch...maybe not the trousers) or a floaty skirt. Kitten heels are a maybe as some find them more unbalancing but they're worth a go. Wedge heels are good too. If you're worried about twisting your ankle a good pair of heeled boots go well with trousers if they're short, and a skirt if they're long.If it's a week and assuming the place your living in is winter at the mo, I would suggest a couple of nice crisp blouses for a good half of the week, and some stretch tops with a blazer for the rest. If you're feeling a little lazy in the bra department use a top with lots of ruffles. Your bottom half staples are well tailored trousers, a knee length skirt as comfy as can be, so 3 days plus 2. Keep it varied-women never wear the same outfit twice. TK/TJ Maxx usually have good clothes-make sure the colour compliments you m'dear. And don't forget (but also don't overdo) to accessorise.
First I'd like to congradulate you on winning the bet. Besides Bill Gates, I think your the luckiest guy I have ever read about. I just recently went through a bet of the same for two days last month. One day was at work and the next was with my gf and to a halloween party. As you probably know, it was an enjoyable experience that i didn't expect.





Is there anything in the rules that say you have to wear a busiess suit or those heals. If not, wear some comftorble skirts with blouses/sweaters and/or pretty dresses that hang no lower than just above the nees. Get a couple of other pairs of shoes with lower heels. maybee 3 inch or 2 inch pumps. Don't wear flats. Because you want to keep your feet looking small and dainty.


If you don't have a slim figure. Get a womans waist cincher thing. That would hug around your waist to promote curves. Wear a bra that fits you every day. preferably one that is water or gel packed. It will make you look like you have boobs. Or get a corsette to cover both areas.





Only wear pantyhose and tights. No boxers or briefs. the reason being is that they are very comftorble and feminine feeling. Which is something you would want to impress.


If you have to shave your face every day. Like I do. Then start using some creamy stuff that woman use to remove it. It will thin it out so you don't look like your growing a beard at the end of the work day. As well shave any other manly hair. Like chest, arms, legs ect. and use some skin softener each day. Hair always grows back and softener wears off after a wile.


Use the next couple of weeks to learn how to put on make up. And fix it sometimes at work. Paint your nails. If there short; put on some fake ones. It's only for a week.


If you have long or shoulder length hair have it put into a girlish style. If not get a long haired wig. The long hair will discise some of the malish look of your face. Get a cheap purse to put your make up and stuff in.





For the best part act like a female. Give them the impression that your liking it. Let them know that they lost on the first day by acting truly feminine. It will aggervate them for the whole week.


Examples:


Blow the hair out of your eyes. There's something special about a femaile that's a little sassy.


Walk with a little wiggle. I found that if you keep the upper part of your thighs together as you walk and take small steps. You give the one foot ahead of the other look without being obvious.


When standing in one spot for a bit. Slightly rub the insides of your legs and knees together. In fact, always keep your legs together never stand or sit with your knees apart. If you decide to cross them it would be cute. But, appart would make you look trashy.


Always do things the way they would. Like picking things up, eating with small bites, be carefull not to smudge your makeup, giggling and talking with a feminine tone.





You did say it was a costue christmas party at the end of the week. Wear a mini green dress with a bra, elf hat, pair of elf looking booties or bootie socks and a pair of red tights. Or a womans santa mini dress with a hat, bra, pantyhose and the 4 inch heels. Win the bet in ways they would never expect.


If there's a cash payoff, after youv'e won the bet. Tuck the money into your bra, Smile and thank them for buying the wordrobe.





Have the time of your life. Because, oppertunities like this don't happen often.





This doesn't need to be expensive. Lots of department stores have clearence racks and sales due to the economy.