You can go 2 ways.
Wear jeans and a pink t shirt.
Or make a big joke out of it and go the whole hog, party dress, wig, lots of make-up, stockings and a garter belt.
This is funniest if you are a really male looking guy, so get a 5 o’clock shadow.
And if you don’t like it, don’t make silly bets.

I have a girlfriend and her son’s school had a “cross-dress” day, she gave him a tampon, told him to put it in his pocket, and now you�re dressed just like all the girls that attend your school. Brilliant.

A denim skirt above the knee with black nylons or tights. Fake Uggs. Stuffed bra in a reasable size for your frame. Black top with long sleeves and big scoop neck, should be stretchy tight. Shave close. Eyeliner, lip gloss.
At a good thrift shop and discount drug store you should be able to get all this for less than $20.

Black mini skirt with red tube top. Platform shoes and a thong. Big hair on top with red lipstick. Fishnet stockings are optional.

Okay. i got caught in the same place. my response to the person i lost the bet to. NO. I’m blowing it off. you can’t force me to or i will drag you into court for what you could call assult. he quickly tried to capture me but i ran out in time and escaped. he still hates me for backing out. but it is the only way to not embarrass yourself.