24/7/365. I wear loose-fitting slacks so there is no fear of the zipper. Been that way for about 3 years. Recently tried wearing underwear and I felt too constrained. Lasted about 45 seconds. There are no more pairs of underwear in my house now.
Never! I like my underwear so I wouldn't want to be without it.
Once while wearing a kilt in the tropics. Very uncomfortable and sweaty.
Another time in shorts to discreetly flash my bits to my other half in a crowded bar, she was commando under her skirt and showing me her vertical smile at the same time.
Otherwise no - too much friction on sensitive parts.
Very rarely, I like everything to be contained.
In pants? Ewwwwwwwww! I love it in baggy shorts, though.
I go about 50/50 these days.
If i'm at home i'm going commando, if i'm going out but not to work i often am too.
I've yet to find any underwear that doesn't make my balls feel crammed up...sooo much more comfortable without any.
This post comes to you from the original and highly disorganised mind of mine...be scared, I certainly am, lol
I do when I am not working at my job
Depends on anticipated level of physical work. In warm weather, especially, I try to go w/o as much as possible. HANG LOOSE!!
I pretty much never go without underwear. It feels weird for me when its just hanging loose, probably just because i am so used to wearing underwear.
I go without most of the time after i get out of work and on the weekends. I like it when i see a woman looking at my crotch and maybe a little smile comes over her face. She might have seen some movement or maybe the outline of my head. It's a turn on !!
Never - getting a stiffie in a public place could become a nightmare!
I am commando most of the time. In Rio it's hot in the Winter, and waaaaaaaaaay hotter in the Summer. At about 80% humidity on a dry day, you need the air circulation.
if I have pants on I have underwear on.
Always have on my boxer briefs if I am wearing clothes.
I often go without, especially when I'm wearing the kilt. It's the next best thing to being naked.
Only when I go out without pants. When that happens my wife almost always calls the police.
Every time I wear my kilt, which is usually a few times a year.