I bought this in XXL because it says 38-40 and I'm a pretty hefty dude. These things were huge in the waste. So size down. Way down. Despite their large waste, MyPakage uses this weird shelf divider that comes from the ass to the base of the sack and kind of props everything up. I did not care for this. The pouch was very roomy, but I'm not sure if it retains that comfortable roominess at smaller sizes. I bought some Saxx at the same time that absolutely blew the Keyhole technology MyPakage uses out of the water so I won't be trying these in a smaller size.

Points to take away: 1) Keyhole technology is weird and feels like you're propping up your junk on a shelf. 2) These size large, so despite what the waste size says, think about going a size down.