When I wore briefs, this was the deal, but it would only work if the briefs were snug. Cotton UW stretches out a few hours after you've worn it, and gravity would always make my dick drop and get squished against my balls. It would get very uncomfortable and I had to constantly adjust. I figured that if it's going to hang, I may as well give it some breathing room. I switched to boxers a few years ago and never looked back. My dick always goes on the right side of my pants or shorts. The left side feels weird to me.