I agree, whatever he wants to wear, a 14 year old is old enough to figure it out for himself and make his own decision. I don't have any man bits, but I think if I did I would want to wear boxer briefs. That's what DH likes, and they seem like the most comfortable option. DS (3.5) has a half and half mixture of briefs and boxer briefs in his drawer. He actually has a couple pairs of boxers too but he really doesn't wear those. I worry they'd be uncomfortable, but when he gets older if he wants me to buy them I totally will. They're his parts! lol He can support them however he wants, as long as he is wearing underwear, I don't care what kind.