The Power of Masturcizing and The Mirror Trick (by Patti, ntcweb)
Before we played last night I considered his comments, and made some modifications to the activity based on other games we play.
Since he had trouble getting past four times, I told him that for every time after four that he finished, I would roll two dice and he could have that many strokes to get himself off.
Normally, there are no opportunities for him to orgasm until much later in our play, so he was excited about this. Of course, he knows it's a two-edged sword. We've played games where I have given him ten strokes to get off, and we have learned that if he isn't VERY VERY close, he will usually need more than that to have a decent orgasm. Sometimes, he WILL start to cum, but not really have enough strokes to FINISH cumming, so it's a bit unsatisfying for him.