I don't mind going commando if I'm wearing jeans (vs. wearing briefs), especially when I get semi-hard down one leg. My experiences with going commando in loose shorts, pants or sweats is that I usually do get hard and pointing out is more embarassing than pointing down the pant leg.

I also have problems with keeping my pants up, especially when walking fast or carrying groceries, boxes, etc., and worry that if my pants ever did drop with nothing underneath, it would cause a great deal of legal trouble.

On a side note, I also enjoy the freedom one experiences on a nude beach and in the water, how good it feels to hang without the constrictions of a swim suit. When I was in Cancun a couple of years ago, while in the ocean, I discretely pulled the supporting liner in my somewhat loose swimsuit out of the way to let my dick hang free, more or less, but still covered up. I'd watch the people that happened to be swimming near me (their heads under the water) and their reactions when they came up and made eye contact. A few smiles on their faces when they looked at me. Overall, that was a great experience. I continue to do this at almost every swim opportunity when I feel I can get away with it