A guy acting like a girl?

[Nevaeh]

I've had this idea for a novel that I'd really like to wirte. The main character is a guy. He's a writer. His English teacher reads some short stories of his and notices that all of his main characters are male. She challanges him to write something with a female main character. He's smart, so he goes to an internet school where he can work on the assignments at his own pace. Since he can do that, he decides that he's going to dress up as a girl and go to an all girls school (as well as his normal online school) to find out what girls act like when guys aren't around.
So...how would he be able to act like a girl without getting caught?

[Tundra]

Be young enough/young enough looking that you don't look like a guy.
Cover your neck so that people don't see your adam's apple? Depends how old he is and what he looks like, really.

[Nevaeh]

Oh, he's probably gonna be about 14 or 15. And he probably will look a bit feminine. It's his voice I'm really worried about. Any suggestions for that?

Also, would his friends who are guys notice if he did things like wear makeup and forget to wash it off?

EDIT: I'm also wondering if anyone knows how I could have him do all this without his parents knowing. Even though his parents are gonna travel a lot, I'd like this school to be a boarding school (because I have a great idea for something with a roommate), and I think his parents might figure that out.

[Maulden]

He could always claim that his girlfriend wanted to put make-up on him for some reason. That sort of thing has been known to happen... >_>

[cowmage]

The obvious rules are the most important ones (no tight pants, cover the adam's apple if he has one, nothing that exposes any part of the fake breasts he's wearing, etc.)

It's a lot easier for a guy to fake being a tomboyish girl than to fake being a girly girl. The reasons for this should be pretty evident.

Does it matter what social groups he's trying to be a part of? Each group tends to come with its own style of dress, and he obviously can't wear certain clothes.
It'll actually be easier to pull off if he can wear something kind of revealing that doesn't show the 'problem areas' - a bare midriff allays some suspicion in these situations (but introduces the concern of the kind of underwear he'll be wearing).
Obviously neither of these concerns applies if the school has a uniform; the second is eliminated or reduced by almost any dress code.

The voice is as much of a concern as you make it; some guys can disguise their voices as feminine with no effort, and some can't do it at all. If he's not a natural, he'll likely find himself coughing a lot when he speaks.

Of course, he may or may not have trouble switching between personalities. The easiest personality for him to fake is a tomboy with a strong disdain for societal conventions - it allows him to act very much like a guy typically would. Obviously, he needs to pick a social group that respects a girl who acts like a boy. (Not sporty types. Punks, maybe?)

[adelaidejane]

Oooh. Just finished watching an anime series called I My Me! Strawberry Eggs! which deals with cross-dressing like this. The guy in question needs a teaching job, but the only one going around is for a female teacher - so his landlord helps him dress up. He has this special choker that somehow changes his voice (I can't remember whether it was a magic choker or not...), and of course he has padded bras. He's...well, it's anime, so he's kinda got a pretty effeminate body to start with - like he's slim and not really muscular like a big macho guy or anything. I'm not quite sure how he conceals his genitals, because they even show him in a sporty two-piece bathing suit at one point - maybe he wasn't very well endowed anyways :wink:

Dunno if this has helped, but good luck anyways!!!

[Thuriel]

Huh. I just want to point out that masquerading as a girl is not the only way to find out how they act when not among boys. I, for example, have learned more about the personal lives of certain girls than I ever wanted to know just by sitting there and letting them talk around me. It's very amazing, actually, how they somehow manage to completely forget that I'm there, even if I'm sitting at the same table as them. They don't talk to me, they don't look at me, they don't notice when I react to something they say... When I say something they notice me again, naturally, but I've learned a lot by just listening.

(For the record, I'm kinda socially invisible even when I'm not just with a group of girls. The same thing happens with any group that doesn't include someone who knows me well enough to keep me in the conversation.)