Usually twice...it takes him about 90 minutes to cum the first time, and 15-20 minutes for #2. After the first orgasm, he needs no recovery period, just starts right back up again.
On rare occasions, he will just cum once, and there have been a few times he has cum three times (Hall Pass hookups in those instances).
On rare occasions, he will just cum once, and there have been a few times he has cum three times (Hall Pass hookups in those instances).