Trip Stone, my dwarf monk (Pathfinder) has worked out exceedingly well so far. 
Last session was a perfect example of how a ludicrously specialized PC can be really, really fun to play.
Module U1, Pathfinder-Style
Our table has moved to episodic play over grand, long-running campaigns. Eric, our DM, decided to run an old AD&D module and convert on the fly. Last night was our first session playing U1: The Sinister Secret of Saltmarsh.
On our initial approach to the ‘haunted’ mansion, we camped in the wilderness in hopes of viewing the mysterious lights that the townspeople spoke of. We settled down for the night and trip took first watch.
It was full dark when Trip hear noises in the near distance, by the cliffs edge. He grabs a small handful of stones and chucks a rock in that general direction. The noise stops, momentarily, and then the shadow of a dire animal rises over the cliff’s edge.
DM: (Flips through the Pathfinder Bestiary for a Dire Weasel and can’t find it. He decides to wing it.)
TRIP: How big is it?
DM: Big enough to eat you.
TRIP: (Imagines something as big as a horse) I let out a battle roar and charge the shadow. I’m trying to bull rush it off the cliff. (Rolls a 1) *groan*
DM: (Grabs iPad for the fumble app) Make a Reflex save! If you fail, you run right off the cliff! (Trip fails)
The dire weasel slinks out of the way and batts at you as you pass, adding momentum to your charge.
TRIP: OOoo K. So Trip runs, full charge, off the edge of the cliff, arms flung wide. Base jumping anyone?
As the cliff rushes past me, I make an opportunity attack to grapple it, right?
DM: Make a Reflex save. The cliff isn’t a sheer drop at first. It starts as a steep slope with plenty of exposed roots. (Trip makes his save) Aaand you grab one! Take 3 falling damage.
The weasel leans over and bites at Trip. (rolls dice) Its teeth sink into your shoulder. Take another 8 damage.
[The party wakes up and arms themselves. They approach the melee but they see no evidence of Trip, just a big ol' weasel-butt.]
DM: OK, Trip’s turn again. You’re grappled by the dire weasel. What do you want to do.
TRIP: I’ve spent my whole life training for this on top of a mountain. I’ll be damned if I’m going to be beat at my own game or fall off the cliff. I’m going to try to reverse the grapple. (rolls) 24?
DM: You got him. (to the party) From behind, you see the weasel begin to thrash its head wildly. Occasionally, you see the dwarf’s feet swinging out from behind its profile.
TRIP: I’ve got hold of a tooth and a jowl! Hanging on for dear life as dire weasel spit flies in my face!
[The party takes a few swings but miss or deal inconsequential damage. Maybe they should try not laughing so hard before they roll the dice!]
From here, it’s slightly less entertaining. In the two following rounds, the monk continues to grapple with the aminal. First, he pins the weasel’s mouth shut and then he ties the mouth closed using one of the long leather belts he loops about his person for such an occassion.
After that point, the barbarian lands a devastating blow on the weasel’s hind-quarters and sends it over the edge. The dwarf made his acrobatics check to scrabble up the length of the dire animal and leap to safety.
Trip really needs to multi-class as a ranger or druid, because it the previous adventure he hog-tied two dire wolverines in a similar fashion. At this rate, we should have had trained dire mounts for the whole party!
