heh fun poll. Lets see...if I was to end up in tickle hell, and can choose anybody, it would either likely be Dawn from the Stocksvill saga, or Tabitha Black from "My Black Rose", both embuad with the dark powers of tickle hell. Possibly both, instead of just one, depending on how masochistic I felt at the time.
As for my actual punishment, I would probably go the way I had intended to write a story one day. My punishment would be a combination between straight up tickle torture, and engaging role play involving tickle torture.