What would be a legit reason that requires you to cross-dress?

Lots of schools hold woman-less pageants during spirit week. Woman-less pageants are popular in small southern towns. They usually start in middle school - when boys are about 10-yrs old, and then they continue and continue all the way through high school. Usually when they are young, its the moms who do all the work. Some moms go all out and treat their boys like they would treat a daughter in a pageant. These boys are not feminine, or gay, or sissies. They are normal, healthy, heterosexuals. Their mom's think that its healthy for a boy to role play, and develop some respect for girls, and learn NOT to be afraid of girl's clothes.

http://www.youtube.com/watch?v=0Gkqd_v6TnE

I know some guys who serve as contestants for several years in a row. Some become pretty good at it and they don't even win because usually the popular guys get the votes:

http://www.youtube.com/watch?v=P1YKE0KnvDk

Woman-less pageants are loads of fun and nobody seems to care that it is cross-dressing. These guys are heroes and they classmates cheer them on. I suppose that some of them end up with a closet full of pageant gowns.

If you are a girl wearing a guys attire say that it is comfortable or something.

If you are a guy wearing a girls attire say that it was a dare.

Although the dare excuse can be used for both.. or you are going to a costume party.

Your curious about what you want to wear otherwise I can't think of any other reason.

I wanted to see first hand what all the fuss is about.