What should I make my brother wear?

Question

I won a bet with my brother and he has to wear my clothes and accessories and look like a girl for a week during winter break. If I had lost I would have had to do all of his chores and clean his room, but I didn't!

What should I make my brother wear?
outfits for a whole week! yes!!!

Answer 1

Wow, big loss. For a day is one thing but a whole week ... wow!
I think each day should have a theme so lets see, all days require hair done, make-up to match the outfit, and nail polish of course, then for each day ...

1) Casual mini-skirt day - short jean skirt, girly t-shirt (pink and says something like Girl Power on it), white and pink tennis shoes, girls socks (shaved legs right?)

2) dress day - just a nice short dress, high heels, accessories (a nice pretty girl look)

3) Bad girl day - A hot looking black mini-skirt (leather?), boots, fishnet stockings, studded belt, tight black top, one of those collars with the o-ring, black nail polish & lipstick

4) Long Skirt day - a long ankle length skirt, pretty blouse, high heels, and carries a purse

5) Prom Date Day - Yep, a prom dress, high heels, and all the trimmings

6) Cheerleader Day - get a school cheerleading uniform and dress him up all the way, make him carry the pom-poms too

7) Mini-skirt day - Short black mini-skirt, white blouse, black nylons, black stilleto high heels (really high, with ankle straps), nice make-up (sexy but not trashy), black grommet belt with the skirt, jewelry (necklace, bracelet, and earings).

Oh yea, and all outfits of course require a bra and panties underneath them!

Bert

btw - me as #6 in the icon, that was this years Halloween Costume - Rah Rah Rah

Answer 2

Unless your brother secretly enjoys wearing women's clothes, he'll likely feel humiliated no matter what you make him wear. I suggest you offer to renegotiate. Tell him that he'll have to don dresses and skirts, and all that go with them (bras, panties, slips, pantyhose, heels, makeup, nail polish, jewelry) for a week -- unless he agrees to some less obvious but more drastic terms. For example, you could let him get away with only panties and bras, as long as he wears them for a full year.

Answer 3

I think this must have been a pretty good bet.I would say try a few skirts, and girl dress shoes.And maby some girlish caprie's,some blouses with girlish sayings on them or maby with flowers.Also maby some cute little barretts.

Answer 4

Not sure why you want to go around town with him dressed that way. I would give him the chance to impress you and your friends with a day out. He can take you out to Breakfast, lunch, shopping, a movie, maybe somewhere origional and creative. If you are impressed by his day out them you let him off the hook. If he fails to impress you and yours by a vote of some kind then let him "have it"

Answer 5

Make him look cute so he'll get lots of compliments (& he'll enjoy it.) Get his ears pierced. Make sure he wears lot of skirts w/hose, and get his hair done at the salon! Take him to the makeup counter for a makeover -- and oh yeah, take lots of pictures!

Answer 6

give him something so femiine you wouldn't even wear, super tight jeans and over stuffed bra or a shirt saying somethings along the lines of "I look better when I'm wet."

Answer 7

jean beam shoe thong. cut hair up to ears die black and wind tight. wear a little girls hair clip and wear some dirty cloths!

Answer 8

anything short and skimpy
with hair accesories
and crazy make-up
good bet! haha

Answer 9

Halter tops, spageti straps, a bra, Skirts, dresses, make up. Anything that's girly, it will be funny.

Answer 10

short skirts and feminine tops