Honestly, that guy's lifestyle seems like it would just naturally wear him out to death and let that serve as his punishment. How the hell would you even balance going out with that many girls it a time? (Carnival Phantasm did a pretty hilarious episode about how exhausting the gigolo or harem master life would be.)
Maybe I just don't think big enough, but it seems like this power could be used more effectively to keep up a romance with one woman (god knows the power would make that a lot easier than it is normally), find a job involving face-to-face negotiations or something similar to exploit the power in a non-romantic way for money, and you'd be set.