Just curious, can you tell when a guy is not wearing underwear?
I go commando when I wear pants, but not when I wear shorts.
There was time I was underwearless and a friend of mine (seriously!) asked me if I was not wearing any underwear. Of course, I told her I was.
She then cam up behind me later in the day and slapped my rear then said "I knew it! You don't wear no boxers boy".
So think some people can tell when you're going for the 'more natural' look.
depending on the tightness of the pants it is easier to tell due to how you "flop" around.
Yes, it does feel better and it's better for you, but...
You're a LOT more likely to leave pecker tracks, that is, pee and sometimes precum stains on your pants and the stains will be visible even after they dry.
You'd also better wipe your ass with wet toilet paper and a lot of it unless you want skid marks on your pants and a bad smell detectable by those walking up the stairs behind you.