Wow... I could do entire pages on how my characters have either smooth-talked or otherwise wheedled their way out of situations. For brevity's sake I'll leave out my Vampire experiences for now.
I played a wizard in a 3.0 Greyhawk game a few years back, Lekinvahr, who focused on enchantments (
charm person was the spell he ended up casting most often). The party was working for the thieves' guild in the City of Greyhawk. By the end of the first session we had already established the
modus operandi of me covering everyone else's getaway.
First mission was to sneak into a dwarf's house and steal a map and some papers regarding a gem mine somewhere within the Cairn Hills. The DM let us stake the place out for a week of game time and it became obvious that no one was home. He figured we'd try for a strict infiltration route (as we were supposed to be thieves, after all). I instead headed over to the tailor's shop, purchased a Velunan courtier's outfit and distressed it, and went to the authorities claiming that this dwarf owed money to investors in Veluna. I wanted to get the map and titles to the mine to be divided up among the "investors." The DM actually took me away from the table to explain how that plan was just too damned smooth, since with a judiciously applied
charm person, the magistrates would go get the map and titles for me themselves. "Incredible idea, but please don't derail my adventure."

I still got a roleplaying award to my XP for the idea though.
As you might imagine, the party essentially burst out onto the street with armloads of loot, followed by members of the Nightwatchmen's Guild concurrently barreling down the street. I jump out buck-naked, flailing my arms and screaming about how an assassin cult kidnapped me and brought me there. Still claiming to be a Velunan traveler, the clerics of Saint Cuthbert take me in and question me about exactly what happened. I told them that these assassins kidnapped me and kept me in the house, where they were apparently operating before some rogues broke in to loot the place and the fight broke out. This was unbelievably sweet- the clerics questioning me actually shared everything they knew about this dwarf. Apparently he'd disappeared a few weeks back, and now the clerics of Saint Cuthbert thought they had a new lead. Not only had I bought the party the time they needed to escape, but I had also inadvertently gathered more intelligence for the thieves' guild and threw the focus of the authorities on finding these "assassins."
Turns out the clerics of Saint Cuthbert were my best friends throughout that campaign. They actually assigned guards to protect me and granted me an audience with Eritai Kaan-Ipzirel when I had a "prophetic dream." I had told them that I had seen a cudgel break a mace, then break and axe, then break a sword, but a dagger stabbed the cudgel, splintering it but not breaking it. The cudgel then bled... This was all followed by clerics furiously scribbling down what I was saying and consulting obscure texts for the meaning of this "dream."
Lekinvahr's crowning achievement (from a smooth-talking standpoint) was surrendering to a really angry paladin and convincing her to let me go. I started passing out bread to kids as I walked down the street with this paladin, saying that, "Hey, yeah, I work for the thieves' guild. But I'm not really evil at heart, see? I work for them because I'm trying to take them down from the inside out. Haven't you noticed how the really evil thieves somehow always slip up at the wrong moment? Did you really think those terribly stupid mistakes were just coincidence? You know when you take me in, whoever replaces me could be alot worse... (sigh) I just hope someone feeds the kids while I'm rotting away in the dungeon for my 'crimes,' noble paladin... Could you at least stop by every once in a while and see how they're doing?"
The DM told me that the paladin was almost sobbing as she told me that I'd better not cross her path again and I'd better be a bit more discrete.
