This wouldn't seem particularly bad
I mean hey, we all fantasized about the cute girl in class when we were teenagers, right?
Some people clearly just have trouble shutting off every memory of that when they turn 16/18/21/whatever the law requires. When I'm 52 I sure as hell won't have forgotten my 15 year old girlfriend (from back when I too was 15). I wonder if my memories of those hot, sweaty nights are legal or not. A photo certainly wouldn't be, even if I'd been the one who'd taken it of her back then with her consent. What I guess I'm saying is that he's probably just stuck in the schoolgirls-are-hot phase of development and so probably isn't an evil guy like that nursery nurse woman from a few weeks ago that everyone's probably forgotten about.
And pretending to be someone they're not? Everyone does that online. From the teenager clicking the "yes, I'm totally over 18" button on a porn site to modifying your facebook profile pic to get rid of that irritating spot. The whole lot's just a web of lies an deceit...
But then there's the pre-pubescent stuff. And that's just wrong (assuming it's not a cartoon- remember that those funny simpsons pics you got emailed last week are soon to be kiddie porn). Saying that it quite possibly stems from the schoolgirl thing, so could probably be psychiatrist-ed out of him. Or at least pared down to a slightly more socially acceptable ephebophilia.
And the icon choice is because- by the sounds of it- he should be walking over a psychiatrist's welcome mat rather than that of a high security prison for a 20 year term of having the crap beaten out of him.
Or should I just say he's a sick freak that should be shot? Probably a more popular answer...