Lost a bet have to crossdress?

Question

Ok i lost a bet now my girl is making me crossdress. she wants yahoo to decide what i should wear. I am going to be wearing the clothes for after school for one week. and i will be going out each day so i can't have anything too revealing, except for one day. she already told me that on the one day i am going to be like a butler for her and her friends and have to go to school dressed up. so if you could please give me an outfit for each day of the week. she wants to buy the clothes asap. I already have long hair so I am going to also need hairstyles for each day as well remember this is for one week with one day including to school during the week. the week will start on this coming monday and end on sunday.

Answer 1

Here's what I say to every guy that has lost a bet & has to dress-up like a girl, just go ahead & dress-up as a girl. You're going to enjoy dressing up as a girl, so you should go all the way & wear whatever you want & dress-up as the girl of your dreams


jk

Answer 2

You have to have the total experience.
* If you're willing to go the whole way, shave arms, legs etc
* A thong won't work, so go for panties
* Of course, a bra. Tissue sort of works, but balloons filled with jell-o (jelly if you're in the UK), or rice works better as you'll get some idea of weight and your breasts will bounce a bit too.
* Don't forget the pantyhose
* Wear a pair of heels

The rest of the outfit depends very much on your build
* If you're well built you'll not want to show off your muscles so wear loose blouses or sweaters with sleeves and a longer skirt. A-line and gypsy skirts can give an impression of hips!
* If you're slim, you can wear almost anything. Try a nice halter-neck dress or a mini-skirt with layered top.

Of course you should dress in keeping with the weather; so maybe consider some boots too. I hope your paying attention to what girls of your age, height and build are wearing too!

Don't forget you'll also need makeup- that includes nails (get some stick-ons if yours are short), and a bag/purse for your makeup, phone, keys

My suggestions for the week are..

Schoolday
Practical - Jeans, Layered tops, Jacket, Uggs or Pink trainers. Hair up in pony-tail. Light makeup

Other Weekdays
selection of skirts and tops. Maybe even a sweater-dress one night.

Saturday
Saturday night (out - party/club) - Black dress, with heels. Hair curled or french braided. (in - pajama party?) Baby-doll nightie. 'Hottie' makeover

Sunday
Off to church with a suitably modest blouse and skirt combi

Answer 3

if I had to crossdress a guy, I would try to use as many of the following as possible.

fishnet stockings,
daisy dukes (if it's warm enough), if not then a plaid skirt with a slip
rollers in your hair,
leg warmers,
a blouse with shoulderpads and sequins
granny cateye glasses
and virginia slims cigarettes,
maybe cowboy boots, but only with stockings on and a skirt
and you MUST carry a purse, one bigger than your head, (ideally leather so stiff it would act as protection from a stabbing attack)

Answer 4

basically try dressing according to weather and your comfort, hair, well if your doing it, maybe just down, or pony tail, would be easiest unless you can get her or another to do it for you. Try to stay simple, especially with the shoe thing.i would stick with pants and a loose fitting top most of the time, flat shoes or tennis shoes. (look at the girls, basically thats what they wear most the time).

Answer 5

Hmm i like the french maid outfit theory in my view, besides i could say you could desire to do a manner tutor modeling each and every variety of female outfits, i do no longer understand what all you have get admission to to yet stuff like: a black gown, a prom gown, a mini skirt...you get the belief circulate to city with it. Sorry with regard to the wager, yet once you could desire to make it much less embarrassing attempt to appreciate it, it is lots extra embarrassing in case you act such as you're afraid of it. have relaxing. :P

Answer 6

first question:
what was the bet?!

second question:
what's the weather like where you are?

ok, for shoes i would say flats, high heels, thick flipflops, and/or high heel boots

you should wear jeans w/ rhinestones or embroidery, a longer skirt, a dress

i don't know. just pull stuff out of your girlfriend's closet

Answer 7

haha sucks for you.


Monday - short shorts, tube top
Tuesday - miniskirt, fishnets
Wednesday - a dress
Thursday - long shirt with leggings
Friday - capris
Saturday - miniskirt, halter top
Sunday - short shorts, spaghetti strap top






bahaha

Answer 8

one of those tight short dresses, panty hose and HEELS

Answer 9

Dude, you sound Wayyyy too into this. :o)