Yeah, I know everyone has a different ick factor. That doesn't personally bother me, so long as I've got clean undies every morning! My point was simply if you choose the proper underwear, it is possible to do it comfortably. To each their own, though.

To answer your question about "proper" shorts, until I am riding for a couple hours, I don't really see much of a benefit in padding. I generally ride with them regardless, but sometimes just grab gym shorts. Really, my MTB shorts with their compression liner aren't much different than gym shorts and compression underwear, if you don't need the padding.