I've been jerking off into briefs since I was 12 by wrapping them around my dick and going to it. I grab a pair from the laundry basket and let it rip. As PinkSteel stated, they're going in the laundry anyway. 2 years ago, my default underwear changed from briefs to boxers. I can jerkoff in boxers while I'm still wearing them. Makes for some fun sessions at the computer. If I don't J/O in my boxers, I have to use baby powder to cut the friction. I made my dick bleed over the weekend by pounding it dry. The only wet lube I use is soap in the shower, and I prefer a dry method when I get off.