Make his life a living hell, OP. Go to sadism and animal abuse forums on Tor, they'll known better than any of us here how to fuck with someone.
If you're insistent on staying on the surface net, try /b/ or some milder sadism forum.
Or just get one of your other buddies to sell him sulfuric acid tabs instead of LSD tabs and tell him it's LSD. Do some research, depending on how far you're willing to fuck with him you can go anywhere from a light dosage that will cause him to need a doctor and thus inform his parents of his life choices (also scare the shit out of him), to brain damage, to paralysis, to death. Your call, OP.
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