Even though I should be putting this on the actual website, I'm too lazy. Basically, this is some of the absolutely idiotic things my friends do.
The party, all of which are playing evil characters, start off in a prison with every conceivable kind of trap and escape-prevention system imaginable. They are escorted out of their cells to a large room where troughs of barely-edible food sit. Guards walk on bridges above, surveying everything. It goes well at first, with my party playing King of the Hill with the other prisoners and making friends with a half-elf that seems to know more than he lets on. Eventually, a raven visits our svirfneblin paladin with a note that says "Prepare." on it. The next day, alarms sound all throughout the building as something unknown happens. Party manages to get their stuff and kill a few guards along the way.
The half-elf helps the party find their way to the exterior of the prison, only to find it levitating a few hundred feet off the ground. As the party debates what they should do, the half-elf activates Dimension Door and helps get everyone to the ground safely. He then escorts them to a shadowy back alley, where they join a thieve's guild known as the Nightrose, lead by a Shadar-Kai by the name of Traedis Vedoran. The half-elf turns out to be a changeling named Ghost. At this point, our githzerai monk, Eregor, of the party gets heart eyes for her.
Fast forward a session, where the party has been sent by Traedis to meet up with one of the contacts. Ghost has tagged along with the party, and this is where the githzerai decides to make a move. He fires up Careless Whispers and attempts to go and seduce Ghost. Anything short of a natural 20 would fail. 15. Ghost whips out a dagger of venom and warningly pushes it into Eregor's throat. He tries again. 12. This time, Ghost decides to lead Eregor away for some "private time." He takes the bait and follows her away, thinking she's about to start kissing him. As he's walking, I roll a dice, laugh, and describe as Ghost stabs him in the back twice, not with the intention to kill but to teach him a lesson. Sore and wounded, Eregor makes it back to camp, where the other Nightrose member, a monstrous black Dragonborn called Ragnarok asks what happened. When Eregor tells him, Ragnarok snorts, informing the githzerai that the last man who tried to love Ghost had his throat gashed open.
Fast forward again. This time, the party had decided to turn on the Nightrose and attempt to overthrow Traedis and rule in his stead. It was a terrible idea, even with the party wiping the floor with driders and other enemies. They're doing ok, but then our drow rogue dies without another word as an assassin rolls a Nat 20 with his vorpal sword, killing him instantly. Another Nat 20 with a Nine Lives Stealer rips the life force of the party's drow ranger. Everyone is overwhelmed until finally, it's just Eregor and Traedis. Traedis makes the first move, dealing a whopping 78 damage with his chain spike and katar. Eregor fights back, but since Traedis had taken one action to teleport, the damage comes out to be 22.
Traedis takes another turn, this time doing 50 damage. Eregor is sweating, only having a few hit points left. In one last desperate attempt to kill Traedis, he uses the last of his ki points to do a flurry of blows and stunning strike. Stunning strike fails, but the flurry of blows does drop Traedis a good couple dozen hit points. Once more, the shadar-kai attacks, rolling a Nat 20 with his spiked chain. I describe how the chain wraps around his neck, coiling and slashing, then is pulled free, shredding Eregor's throat. Never take on an entire thieve's guild unless you know what you're doing!