Dressing right OR left?

sdbg

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How do some of you guys "dress up?" I mean, how do you get it to stay in that position?
When I wore briefs, I've always pointed it up toward the waistband. If they were snug enough, junior stayed in place all day. 6 years ago I discovered boxers and let junior hang freely. Whenever I wear cycling shorts or a Speedo, I point it up. It feels very uncomfortable to me to point down if I'm wearing anything tight.