If there is anything on which every tabletop RPG Game Master (GM) will agree, it is that you must always expect your players to do something unexpected. Allow me to illustrate eternal truth this with the story of my last library D&D session.
Following their previous adventure, I had a looser outline for the next chapter instead of a scripted story because there was room for many different options. The party returned to Brightvale from Wharton Mine as expected. They had decapitated the necromancer as physical evidence of his defeat and brought his head, along with his notes, to Brightvale.
Raissa, the village matriarch, recognized Onvyr immediately and said he had been the orphan of traveling merchants, and the town had taken him in and given him a home. They also raised funds to send him to the Cliffport mages college when his academic inclination was too obvious to ignore. The mysterious "Samwell" he had mentioned is the high mage who administers that college. After the party recounted the details of their adventure, Raissa asked them to escort her to Cliffport so she could get to the bottom of the matter and find out what had happened to turn Onvyr so hostile toward his adoptive hometown.
The party met Raissa the next morning at dawn. She surprised them by carrying a dwarf-made blunderbuss along with her traveling pack. She gave them the choice of walking several days further south to a swift river, or returning one day's journey to Riverton to find a cargo barge to hire passage. They chose the latter. In Riverton, they met Captain Brevar again, and he reported that in the last few days the town had finished cleaning up the desecrated temple and was actively seeking a new cleric to minister to the people. Raissa commented, "Well, it turns out you were right about somethin' fishy goin' on. I thank you for sendin' these folks to watch out for us, much as it pains me to do so!"
The barge journey was uneventful, and the party found lodging at the Angry Seagull for the night. One player elected to camp outside of town, and went beachcombing. I had him roll a DC12 perception check, and he passed, so I rolled on the d100 random item table. He found a gnomish music box that played a strangely familiar tune from his childhood. A lively bit of discussion regarding the nature and duration of Dragonborn childhood ensued.
The rest of the party went looking for passage to Cliffport the next morning. I told them there were three possibilities: a large cargo ship, a well-armed ship that they learned was a pirate-hunting ship run by paladins from the Order of the Burning Lance (the inquiring player got the privilege of naming the order and the ship), and a small sloop. One party member negotiated for passage on the pirate hunter ship, but there were three players interested in the sloop.
A sloop is a single-mast ship with a fore-and-aft rig. Image credit
I worked with the beachcomber to invoke his backstory and established that the sloop was captained by an old acquaintance named Josephine. He had brought some onyx as an apology gift due to the circumstances when they last parted, which involved ship damage. However, he was late to the party. You see, two other players hatched a more nefarious scheme, and this is where the story went completely off the rails and I had to improvise.
These other two said they wanted to steal a ship, and wanted to find a sailor willing to smuggle them aboard a ship they could commandeer. I allowed them to roll for it. They found someone. OK. Who would agree tonsuch an offer, though? Clearly it had to be someone who was a backstabber. So I decided he was looking for some landlubber chumps to shanghai. I intended that these two would be captured, and I could spin it into a search-and-rescue mission for the others. So the first player approaches the sloop and sees someone leading his companions up the gangplank and then through a hatch below deck.
A short while later, the two players climbed back up as the first was also clinbing the gangplank. They rolled extraordinarily well, and the sailors waiting in ambush with belaying pins rolled extraordinarily poorly. All four sailors were dead, and only one of the players had taken any damage. The dragonborn was enraged when he saw his companions emerging with bloody weapons, and tossed one overboard. The other went into sneak mode and managed to disappear quietly when eyes were elsewhere. Captain Josephine emerged on deck to find her former acquaintance sputtering about murder and dead sailors. She was naturally shocked and called for the town guard and the harbormaster to investigate.
It turns out her crew were planning to mutiny and establish themselves as slavers and pirates. The one party member who had been involved in the double-crossing tagged along and managed to argue that they had just been innocent travelers seeking passage before being ambushed, and the party avoided any blame.
In the end, everyone set sail for Cliffport on the warship.
To be continued...
So, the party did not need the pirate encounter I had planned, and instead tried piracy themselves. I had to improvise everything and spin a story that responded to their choices and actions completely off the cuff. I had to petition the players for backstory details I could weave in on the fly. It was completely bonkers, and a whole lot of fun. Will Captain Josephine return? Will she be appreciative of her former companion uncovering the pirates in her crew, or will she consider it more of his bad luck aura? Why is Raissa armed with such a rare and expensive weapon? And what will the party encounter in Cliffport? Well, some of the Cliffport part is partly done already, but the rest remains to be seen. Being a GM is fun!