i'm not into anal, so i've never done anal. but i guess you'd go at it like a chick, yah? work him with your fingers. when you do get to the point where you stick your cock up his bum brah, go in very slow and use a lot of lube.
and, i hope you know this already, but there are a lot of peoples here, who, shockingly, don't...wear a condom.
also, i dunno if it's been asked but...if he's done it once before, how is he a virgin?
EDIT: ok, some other peoples have questioned this haha. also...i'm stoked you
re not gonna use drugs and alcohol with him