Well, his first pass on Sunday had a LOT more pre-cum than his first on Saturday (which was reassuring for me, because it meant he probably hadn't cheated) and each one after that was more still.
After the fifth one, I rolled the dice for him, right on the mirror he had just licked clean. Unfortunately for him, he rolled a seven. The look on his face was precious -- sad and frightened at the same time. He gave himself seven very slow strokes, but wasn't able to cum.
I told him he probably hadn't gotten himself close enough, and would he like to try again in a few minutes, and he jumped at the chance. (Hmmmm... one thing I'm learning about this whole Mistress/subbie thing is that the little boys seem to make VERY dumb decisions when their cocks are hard and dripping.)