Max: I would say that you could pass if your mannerisms were right, which they must be if you're passing to your classmates. Your hair looks unkempt enough for you to just to be a long haired guy. I'd suggest wearing t-shirts with rounder neckholes, or smaller ones at least, because low or pointed ones look more feminine to me, although if you're wearing the same one in both photographs then it could just be the angle in the second photo. I'd say that you were maybe 14.
Seth: You definitely pass.
Tom: You pass as well, but I'd probably think you were gay, emo, or both, especially from the last photo.