I cried when my dad died for sure. If you are asking "is it ok to cry in situation X, society tells me no", then the answer is no, because society told you that. You can apply reason, but it won't matter- if you think that, in your society, crying over thing X is not masculine, then crying over thing X makes you less of a man, full stop.
Basically, if it wasn't true (to YOU), you wouldn't have to ask. You'd either not perceive that society was telling you that, or you wouldn't care.
Is it a truism? Does crying make you a bitch? No, of course not. Unless you believe otherwise, and you don't get to really pick and choose beliefs at this level.