Another hilarious guest submission, this time by Joural0401:
This story isn't about a bad DM or anything of the sort. It's just… it needs to be shared. We had an average party at the time, and were in the middle of confronting a pirate king. Sorcerer, Rogue, Fighter, Barbarian, Cleric. Pre-gunpowder, so ballistae are the primary weapons for boats. The entire party is onboard the Pirate King's boat, and he's reaming out the pirate captain who led us here(apparently he's done these kinds of things in the past). Eventually it's decided that the pirate captain will have a chance of surviving, so they put him on a rowboat, and the DM immediately starts describing the captain frantically rowing away.
Apparently, the thief never read anything on TV tropes, so half way through the description of the captain in the horribly rickety boat, he says "I jump on."
The entire table stands silent for a moment, before the Fighter says "I follow him."
I(the sorcerer) try to stop them, but can't convince them and I fail my grapple check. So they're on the boat. The Pirate King turns to look at us, makes a comment about how our friends like to gamble, then starts talking about how the Big Bad has access to all these amazing innovations of weaponry.
Three cannons, all pointing at the little rowboat. The first one fires. Miss. Second one fires. Miss. Third one fires… hit. Reflex save time. The both make it, so the fighter takes half damage and the rogue takes none. The DM pauses, and asks for a second reflex save. Again, the Fighter makes it, but the Rogue fumbles, and is now bleeding 1d3/round. In the ocean. The rogue fails a swim check, so the fighter swims down and saves him.
Around this point, I realize what's coming next while the fighter is crowing "We survived!", though given the status of the thief at the time(he got a 1 on a fort save, so now he's bleeding 1d4), might have been premature anyways. Then the fins appear.
Sharks between them and the boat we came from, sharks between them and land. Fighter swims for a turn, but decides he'll have a better chance if he drops the rogue, and the rogue barely makes it to swim under his own power. He's still bleeding out. Fighter swims off, rogue decides to swim in the other direction because… hell if I know. A turn later, he fails a swim check and a fortitude check, and ends up unconscious underwater, while the fighter swims a bit further. The DM is generous and gives the Rogue a fortitude save to have one last chance at surviving. Says 'you'd basically need a natural twenty to wake up.'
Entire table silent for the fateful roll.
Everyone leaning in.
It was the perfect moment of cinematic you'd-never-believe-it-in-a-
movie, but the rogue wakes back
up, no longer bleeding, underwater.
"make a swim check."
So the rogue is dead.
Meanwhile the fighter has realized, at long last, you can't outswim a shark, so he draws his weapons to try and fight them off. He fumbles his first roll, and his sword is out for the round. Dagger time. Rolls for it… fumble. Both attacks miss. Shark turn. One of the sharks charges forward to attack. Critical hit. The fighter had 3 HP left following the cannon hit- now he's at -11.
So both 'let's get on the boat' people are dead, end of the story, right?
Wrong. Because I made the mistake of intimidating the Pirate King.
A round later, I was blind. The cleric tries to guide me to cast a spell but when it fails I just enlarge person the Cleric(phase one of any combat at this point is, of course, to enlarge the barbarian), climb on her back, and tell her to swim like her life depends on it. We hop in the water(sharks are better than the CR like 10 or whatever guy on the deck) and swim to the boat. Making it on board, the session ends with the captain of our ship asking where the rogue and fighter went.
None of us knew how to answer until the Barbarian says "Well, last thing I heard them say before the sharks showed up is 'I got this guys,' so I'm sure they're fine."
End of the night, end of the best session ever.