Something tells me this poster is not a parent! 
Update: I do have the friend’s telephone number and address. I had Paul call the number last night and no one answered but he left a generic “call me” message with our home number. We’ll just try until we get someone, which may not be until after the holidays.
Pasta, I do think he’s a good kid. 
There were things in Hustler which disturbed a lot of people (women in a meat grinder being the classic example.) Playboy, yeah, you’re probably right, it’s about as vanilla as it gets (or it was when I was stealing Dad’s in the 80’s). Penthouse…well, I learned about chicks with horses and a particularly delicious story about a girl whose father forcibly bred her to a farmboy, leather restraints and all, from Penthouse, so you make that call. I’m sure *my *mom wouldn’t have been happy about that.
And, despite Rule 34, the vast majority of porn found online is more Penthouse than Hustler. I’d even argue that watching amateur porn online, with real people of mixed ages and body shapes and preferences, might give a kid a much more realistic view of sex and men and women than either the airbrushed or cookie cutter raunchy fantasy porn of yesteryear. At least they get to see how to give women REAL orgasms! 
Not as far as you know.
Whacker’s gonna whack. Get the kid a Costco bundle of kleenex and a PC in his room with decent antivirus/antimalware software and leave him alone. he’ll know what to do.