Tighty whities briefs... mainly due to the humiliation factor and the fact that it's not too rough on your junk. Normal loose boxers are terrible to get wedgies in because the fabric can be pulled up splitting your nuts or cutting your crack. I was given several wedgies in boxers (switched from tighty whities due to peer pressure, but eventually switched back in high school) while in middle school, and while nothing got permanently damaged, I wish I had been wearing tighty whities for those wedgies because it would have been somewhat more embarrassing (and the prospect of me wearing tighty whities seemed to be of interest to my friend), less painful, and more enjoyable. 
Boxer briefs... I guess they're like getting a wedgie in briefs but with more available fabric. Wouldn't really know though... only wore boxer briefs for a year or so in high school (and wasn't given any wedgies), and since then, it's all been briefs for me.
Boxer briefs... I guess they're like getting a wedgie in briefs but with more available fabric. Wouldn't really know though... only wore boxer briefs for a year or so in high school (and wasn't given any wedgies), and since then, it's all been briefs for me.