I would try it around the house first. For me I just can't do it; just average size but I can't stand the jiggle and even if I could I find that most of my pants irritate/scratch my glans.
I see no albums in Josty's profile so I have no idea how his penis hangs. He says that it is just average size, which may be part of the reason for the irritation.
I think that how it hangs or doesn't hang might affect how much irritation results from freeballing. If you have compact balls that push up under your cock then it will project out in front of you, to be chafed by your pants. Walking will make it move side to side to chafe on the fabric.
If your balls are loose and low, allowing your penis to hang stright down from your crotch then it can hang down one leg of your pants and swing freely, without chafe problems. Mine is 7" flacid and my balls hang below the tip of my cock in summer, so I have no problems. I sometimes adjust the height of my shorts to get the tip of my cock to lightly touch the center seam as it swings when I walk. It creates a very pleasant sensation to keep me smiling with nobody knowing why. In the cold of winter my balls pull up and my cock shrinks a bit, so it pushes out to the front a bit over my balls before turning down. Then tighter jeans hold it in place with less likelihood of chafe.
I saw a survey somewhere (non-scientific of course) that showed that well-hung guys are more likely to freeball than those who are not well-endowed. Among other possible reasons, this may be because of the difference in chafe between hanging and projecting cocks and the discomfort of cramming all that flesh into underwear.