It’s a cultural thing, isn’t it? I sleep naked. Were it I, I’d pack boxer shorts or be prepared to sleep in my boxers if seeing me naked seemed to bother him. It’s never wrong to make some effort on another person’s behalf.
Personally, I wouldn’t have any problem winging it, so to speak, taking measure and making a judgment the first night. Exactly how close are the beds, for example; I assume these are not bunk beds and you wouldn’t be climbing up and down from the top bunk; how much space will there be between you, that sort of thing? I wouldn’t be afraid asking him whether he cared, if it seems the thing to do. However, remember, if you ask, you have to respect the answer.
He might not care. If it seems awkward, maybe you could slip out of boxers with your back to him when getting in bed and slip them on when getting up. Would he really be upset if he accidentally caught a peek? That seems to me to be a little much for two guys sharing a room for two weeks.
I wouldn’t normally expect to wander about a room nude, sitting on my bed nude, around just anyone, first night out. While it wouldn’t bother me I understand some people are different. Some guys at LPSG claim they’ve never even seen another male’s penis. It’s amazing to me, but I guess if people never lived in dorms or frat houses, were never in the military, don’t shower at the gym, whatever, maybe, that’s their normal.
Actually, what I’m wondering, isn’t anybody going to wank for two whole weeks?