Oh wow, you'd make him write the whole word all over again 5 times eh? Harsh, but probably appropriate. I'll bet he would never submit a Y like that again after that experience! (Or any other letter that wasn't properly cock-painted either.) ;-)  And if I recall correctly, I don't think he used his hands to hold his dick the entire time. I'm pretty sure that was a rule of mine, no hands allowed anywhere near his dick while painting I mean if you think about it, if he was working hard to earn the right to touch his dick, he shouldn't be able to touch it in the process of earning that right, agreed? But I'll have to find that video and check it to be sure. If he did touch his dick at any point, maybe I should still punish him now, even though it's years later? I wonder what the statute of limitations is for improper cock painting punishments? Is anyone out there a kinky lawyer? *grin*