I must admit I've never got this showing it off thing either. How easily people could see my cock never crossed my mind til I saw some of the topics on here. I'm usually wearing loose fitting dark jeans or trousers which I don't imagine they show much. I've recently started wearing closer fitting jeans, but that's because I've lost weight and got in better shape so I think I can get away with them now, never thought about how much it shows my dick.. in fact usually the pants I wear are irrelevant, most of the time I'm outdoors I wear a full length black wool coat that obscures my crotch completely.
The idea of wearing something deliberately to make it blatantly show is just odd, god have some decency, there could be children around! Believe it or not the whole world doesn't want to see it. And as for getting laid, well if you really have to rely on your size to generate interest, just sleep with the most loudmouthed biggest gossip you know and let your reputation spread, there's no need to parade it in everyone's face...