Milk him over and over!

He couldn't hold back and orgasmed hard, but you are far from done with this pathetic loser! He clearly needs to be given more training, so to teach him a lesson you decide to strap him to a milking machine and torture his cock with relentless mechanical precision. He may squirm and whimper all he likes but the machine will milk him dry. Without a doubt, he will remember not to underestimate you next time!