As a guy who wears thongs 99% of the time, I’d love to weigh in on your hypothesis that smaller undies hurt more!
Your standard cut of thong (
like these by Jack Adams) really aren’t that bad. Dare I say, maybe not even as bad as tighty whities?! A lot of thongs cut like this are really stretchy to be more comfortable, so even if there’s not a lot of fabric, it’s not super painful unless someone pulls them super far. Now if you get a cheaper pair without much stretch, they’ll definitely hurt a lot more!
G-Strings (
like these by PetitQ) are the definition of butt floss, and a wedgie in them is always pretty painful. No matter how stretchy they are, it’s still a little string being pulled between your cheeks, so even a casual tug is going to sting! BUT that little string rips easily, so there’s kind of an upper limit on how hard you can pull a G-String.
Then we’ve got the thick-waistbanded, almost jockstrap-looking, “more manly” thongs (
like these by Marco Marco). These are BRUTAL to get a wedgie in! I’d have to say top of the list. Usually the waistband on these is very stretchy, but the strap between your cheeks isn’t AT ALL! If a G-String feels like floss being yanked between your cheeks, these can feel like a rope. Even a gentle tug and you’ll feel a lot of pressure between the cheeks. This is the only type of thong where I’ve literally been picked up off the ground, all my weight on just a strap between my cheeks. And THAT was painful!
All in all, I’d say a lot of it comes down to how stretchy the material is. Can’t comment on boxers, though. Haven’t put on a pair in 15 years.
