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So, in our last session we had a fine example of tag team chicanery.
Neither are especially focused on social skills, though they both have fair values in Bluff (a 15 and 10, respectively).
So, a group of bugbear, ogres, and an ettin, all members of the army the PCs are allied with, decided to try to shake them down. The monsters were in way over their heads, as the PCs are 13th level. I expected them to just destroy the fools and move on. Little did I know...
The biggest (and dumbest) ogre, demands a toll of 50 gold apiece from the PCs and their assorted cohorts/minions/hangers-on. The vampire, pretending to be confused, successfully bluffed the ogre into thinking they (the PCs) didn't know what gold was. The ogre pulled out a handful (17 gold) of coins, and showed them. The drow (with his Sleight of Hand skill of 15, proceeds to try to steal the gold out of the ogre's hand while he's talking to the vampire.) He rolls a 2, but even with the +10 bonus for the spotting obvious theft, fails to spot the drow take the money. He is confused as to where his money went.
The drow then proceeds to attempt to pay the toll, with the ogre's own money, and bluff him into thinking they gave him more than what he demanded. One decent bluff roll by the drow, and abysmal sense motive check by the ogre convinces him that since 7 is obviously more than 5, 17 gold is more than 50.
The PCs go on their way, but I have a feeling the band might figure it out eventually and confront the PCs at a later date.