Wash your ass, dude.

I think it depends on the thickness of the cheeks and thong/string. I have a thicker than average booty for a guy, and I usually just feel thongs rest between my cheeks. If I start doing some crazy stretches or yoga I’m sure it’d get a little closer to the anus as things spread out.

Strings definitely get more up close and personal, but I feel it more on the top of my ass where it meets my back and on my gooch than my anus directly. It definitely goes a little deeper between the cheeks though, but I sure don’t feel it rubbing against my anus. The right thong/string should feel like almost wearing nothing.

Guy here, I’ve worn a few in my time and it’s a lot like wearing a new ring on your finger, at first you notice it constantly, you feel it between your fingers and you notice when it moves, but eventually you forget it’s even there. Exact same experience with thongs. After the initial sensory experience wears off its as present in your mind as the underwear you’re currently wearing. It doesn’t move much between the cheeks, and I can’t say I’ve ever explicitly felt it shading my asshole.

Personally I’m not a fan of them because they don’t provide the two things I wear underwear for, padding between my thighs so they don’t chafe, and decency if I manage to cut it rip my pants while working. If I don’t need to worry about those I’ll just go commando.

Isn’t that the whole point? But no to the latter question. Your shoes rub your toes but you probably forget about it after a while. Ever wear sandals? There’s comfy pairs and uncomfy pairs.