I’ve always wanted to run an elaborate prank session as a GM. How wonderful, I thought, if I could disguise the powerups from Mario or the plot from some famous movie, only to reveal my fabulous gotcha! at the the final moment.

“Your princess is in another castle!” the myconid steward might declare. Or perhaps, once the orc shaman had fallen into her designated acid pit: “Only her footgear remains. The shoes are surprisingly fashionable though, festooned with red gemstones. Upon further examination you discover that they are magical, and can cast word of recall once per week. Would you like to know the command word?” Cue GM troll face and pained player groans.

Of course, even though I’ve read about this stuff on the interwebs, I never got around to making such shenanigans a reality. Certainly I never thought they would be perpetrated upon my poor unsuspecting person. Is it time for another tale from the table? You bet your Lollipop Guild union dues it is!

So no shit there we were, foundering on the shoals of catastrophe. The session premise was that we’d been washed up on an uncharted isle post-shipwreck. No complaints though. (It’s an old trope, but it checks out.) What made the situation interesting was our NPC escort. We’d been sent on a diplomatic mission, and it was our job to keep Madame Ambassador alive while we scoped out the tropical wilderness and found some means of escape.

Our first stroke of luck was another wrecked ship. It had apparently washed up on shore some years ago, and looked to be a magical boat. It was also missing a big chunk of its keel.

“Could we restore it if we found the keel?”

“You mean the McGuffin?”

And so we had our mission. The next piece of luck came in our first combat encounter. Scanning the clifftops overlooking the beach, we spotted a humanoid figure looking back at us. He was clad all in red. And as the lanky weirdo begins to pick its way down towards us, the ambassador pipes up with some lore.

“These islands are supposed to be uninhabited. Even the pirates have given up on them. The last who sailed these waters perished in my grandfather’s day: a fearsome buccaneer by the name of Lord Howl. His ship was supposedly lost at sea some fifty years ago. Wise mariners have steered clear ever since.”

I should mention at this point that this session was part of an ongoing Dungeons & Doggies campaign. No doubt Lord Howl would turn out to be a warg or a werewolf or some other appropriately themed beastie.

Any dang way, by the time the ambassador finishes her exposition the figure is shambling down the beach towards us. He calls out in a weird, broken voice, and we soon discover that it’s a jester wearing red motley. He is also clearly undead.

The fight was short and very one-sided. The ghoul had some kind of homebrew escape powers though, so he slipped our barbarian’s grapple and bolted into the woods. All the while he’s muttering in that dorky voice of his, “The captain’s not gonna like this!” Lacking any better leads, we followed after the jester. If he was the minion of a very-probably undead Lord Howl, we figured he might lead us towards the missing keel and our ticket off the island.

Fast forward to combat encounter #2. The jester’s trail led us to this huge, elaborate treehouse on the far side of the island. Thatched roofs and platforms and spiraling staircases were bolted onto the biggest palm tree any of us had ever seen. And coming down one of these staircases was another undead. He held the jester in one beefy hand, shaking him by the scrawny neck and berating him for failure.

“Captain Howl?” we venture.

“Yes, and no,” replied the abomination. “I am the Captain, but Lord Howl waits within.”

The jester scampers off once again while we do battle. Grapple barbarian manages not to fail his rolls this time, and action economy soon puts an end to the flesh golem pirate captain.

Encounter #3 came immediately thereafter. And for a change of pace, it was a social scenario. The jester is quivering behind a wizened old undead who calls himself the Sage. “What do you want here?” says this latest monstrosity.

“We want off this island. Take us to your leader!”

“Very well,” croaks the Sage. “But be warned. If you seek an audience with Lord Howl, you had better prepare a worthy gift.”

Diplomacy turned out the be the right call, as the Sage shepherds us past another couple of combat encounters. The first chamber has this weird stage or dais or some such, along with a female undead in a tattered gown. Relieved to bypass a banshee fight, we pass through the kitchens en route to Lord Howl’s throne room. There’s a water-logged corpse scrubbing mindlessly at rusted pans. It peers at us through lank brown hair, and once again we feel like clever adventures for skipping the fight.

At this point we traipse over a narrow bridge to a final chamber, arriving inside the highest room of the treehouse. A pair of undead sit on a pair of bamboo thrones. One is wrapped in tattered sail cloth. His paramour looks to be some kind of creepy veiled lady.

“Lord Howl, I presume?”

“Gifts!” roars the pirate-themed mummy.

“Well you see, we were hoping to make our way off this island. If you could see your way to lending us that big chunk of keel-shaped wood strapped to the back of your throne….”

“I want gifts right now!” demands Lord Howl. He’s got a posh Mid-Atlantic accent for some reason, which is not exactly intimidating. But being spectacularly patient PCs, we begin offering gold and minor magic items. They disappear one by one, popping through Lord Howl’s wrappings and into his chest cavity. He seems to grow stronger with each offering, and he absolutely refuses to bargain. “More gifts!” he keeps shouting. And it’s at this point that we launch into Encounter #4 of the evening.

The jester chases our poor rogue around. The Sage levitates into the air, then begins to hurl coconut-grenades down at us. Meanwhile Lord Howl is wailing away on grapple barbarian, who is doing his best to rip the keel out of the throne via multiple Strength checks.

A few rounds later and combat is going surprisingly well. The jester and Lord Howl teeter at the edge of the throne room balcony. The Sage has been blinded, so he’s throwing around incendiary coconuts with reckless abandon. Meanwhile grapple barbarian has finally worked the keel free from the throne.

“That only counts as my free ‘interact with object,’ right?”

“Sure!” says our GM.

“Perfect! Then I charge the jester and his boss, using the magic keel as an improvised great club.”

The multiverse has a sense of humor, so of course grapple barbarian crits. Of course the damage is massive. And as the burning palm tree begins to topple, and as the undead fly off into the stratosphere like Team Rocket, Lord Howl berates the jester with words that I’ll never forget: “Ghoulligan! You idiot!”

The table froze. You could hear the hamster wheels turning as our minds cast back over the session. The lanky jester all in red. The Captain we’d fought downstairs. The fabulously dressed banshee and the brunette scullery zombie. The Sage and his coconut-based ordinance. And then of course…

Lord Thurston Howell III!” whispers the dumbstruck barbarian.

“And his wife!” cackles the jubilant GM.

We escaped shortly thereafter.  With the keel restored, the wreck turned back into a useful magic item. No points for guessing the name of the boat though. It was painted bright and bold on the side, clearly visible once we brushed away the sand. We also managed to swipe a magical walkie talkie that could cast message, but only between the two halves of the same coconut. I’m not sure I’ll ever forgive my GM.

I hope you’ll forgive the long-winded tale, but this mess happened just a few days ago. The outrage is still fresh in my (and my grapple barbarian’s) mind. What about the rest of you guys though? Have you ever fallen for similar GM chicanery? If so, tell us your tale down in the comments! And if not, please send your condolences. I need all the sympathy I can get after falling for that one.


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