I wear underwear when going outside or otherwise I might be flapping around, but not around the house. It's way too constricting. Feels so much better without it.
Interesting that most men posting here don't but then that's probably why they chose to answer this question and why it was posted. Personally, I would never consider going without underwear a] because it is not hygienic and I cannot imagine any woman would consider sex with a man who didn't wear underpants and a fresh pair every day and b] women could comfortably go without panties under a skirt because they do not have significant external genitalia. We, on the other hand have both a penis and balls which need for comfort to be contained and supported. Stylish well fitting briefs or trunks are both practical and attractive.
I used to worry about the “flapping around”when ai was younger, but not anymore.who cares if someone notices the presence of my penis. I am a nudist, and am used to people seeing me. Why worry about it when I have to wear clothes?
Actually it's healthier to go without wearing underwear. There's a reduced risk of yeast infections, you'll have fewer allergic reactions, reduced chafing and irritation, and improved circulation in the scrotum. Plus the balls are further away from the body which promotes better sperm production (for those wanting children). All the women I've been with haven't cared that I go commando when they lower my pants. In fact they like having easier access (so do I).