Cry a lot? I didn't really notice much of that. Despite him crying upon hearing a specific 'death,' and waking up with tears in his eyes, I can't recall him crying. Well, except if you want to say that "tears welled up in his eyes upon seeing Nat." is called crying as well. I personally thought it was a good way to show that Leon thought more of the kid than just someone who followed him.
My compliments about the story, but I can't go into details just yet, considering I'm one of the judges of the Story Contest.