All Things DnD's Story Dungeon

Warlock Outsmarts The Dungeon Master & Surprises Everyone

June 08, 2020 All Things DnD
All Things DnD's Story Dungeon
Warlock Outsmarts The Dungeon Master & Surprises Everyone
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All Things DnD's Story Dungeon
Warlock Outsmarts The Dungeon Master & Surprises Everyone
Jun 08, 2020
All Things DnD

When your own homebrew magical items backfire. Well played, this was honestly the best quick thinking I’ve heard in a long time.

Show Notes Transcript

When your own homebrew magical items backfire. Well played, this was honestly the best quick thinking I’ve heard in a long time.

The Warlock Who Managed To Outsmart The Dungeon Master & Surprise Everyone

Hi everyone. All Things DnD is back with another story. This is winning in DND. So many stories are about terrible DMs trying to beat down their player’s but this story is the exact opposite of that. We’d love to hear about your “winning” moments after you listen to this masterpiece that made us clap for the warlock in the end:

This is the story of when a good DM made an active attempt to kill most of the party in as hard a fight as he could fairly give us, something he fully admitted to afterwards, but things went wrong for him in the best way possible. Technically, it’s not possible for any single player to win at D&D as it’s a team based roleplaying game where you’re just supposed to have fun and slay imaginary goblins to get fictional rewards. Still, I’d argue if you’re able to not just ruin the plans of the DM in the best and most epic way possible, breaking his spirit in the process, but also get away with many more loot and experience then you should have gotten by a long way, then yes, you have won at this game.

Next game though, be prepared to fight an Archmage Tarrasque single-handedly if he feels as if you’re getting a bit too cocky.

The DM always remembers what you do.

This game took place in a West Marches setting, so we were doubled up on some classes and races. That said, let’s get this story started by introducing our players:

I’m playing Honest Con - Tiefling Warlock of Lathander, merchant lord, capitalist and greedy adventurer. Puts the “ha” in chaotic neutral. Only reason Lathander is his patron is due to spending over a year wearing the god down into being Honest’s friend. Basically, I played Honest as a ridiculously cartoonish Satan mixed with Monty Burns from The Simpsons and Del Boy from Only Fools and Horse.

The DM: A great guy who loves mean traps, meaner monsters and random magic effects. Will let you roll anything as it’s cool, or you can RP it properly.

Christabella Thornwhip - Halfling Wild Sorcerer, chaotic small person and, after a game I ran for her where she found a magic item that mutates organic life, has a big red squirrel tail with a large razor toothed mouth on the end. It’s neutral evil in alignment but doesn’t really do anything other than whisper fun prank ideas into her ear.

Xagath - also a Tiefling Warlock, but of Mephistopheles. Decidedly the opposite of Honest in every way. Holds a corner office on the eighth layer of hell and has an Imp familiar called Vom who dies every game without fail. Mostly at the hands of the rest of the party.

Valemon - another Tiefling, another Wild Sorcerer. Snarky and sarcastic. Own’s a gardening center, though it just amounts to a ruined garden shed. The only indication that it’s a shop being a small sign on the door and a few withered plants on the shelves. Very much the blaster of our party.

Tarhan the Giant Slayer - blue Dragonborn Fighter, beefy boy and, yes, he loves fighting giants. Made it a personal goal to try and slay one of each kind for the fun of it. Eventually, we finally decided to just make it canon that the tale of Tarhan the Giantslayer was so great, that giants read stories about him to their children to frighten them into behaving.

The party is exploring the mountains north of their hometown, Miran, looking for a city sized airship named Zale’s Heaven.

It’s said to have gone missing centuries ago under mysterious circumstances. Made of metals and magic lost to time so we figure it must be very valuable.

Honest has a lot of interest in this ship for a few reasons.

Current Warlock patron is Lathander the Morninglord, god of the sun, but the old one was an Elder Evil known as The Dust.

Elder Evils are always campaign enders. Look up Atropus the World Born Dead, and you get the general gist for how strong they are.

Honest considers it in his best interest to find an aircraft which can move VERY quickly.
They find the airship after a week and explore it.

After passing through several magical portraits where some weird stuff happens like Xagath dying and being resurrected, jumping through fixed points in time and Christabella gaining an epic boon by rolling very high on percentile dice. We find the Lich.

The Lich has put himself in suspended animation on his throne and surrounded by all the things he considered to be most valuable to him. Wealth, magic items and, behind him, not a thing, but a person.

His lover, a Mermaid the size of a Frost Giant, frozen in ice so thick that we could have used all our spells blasting it and gotten nowhere near to reaching her.

Later it turns out that the Lich and Mermaid were the DM’s and another player’s old characters.
I think they did this to themselves as, over time, a Lich will slowly lose their humanity and this one didn’t want to stop loving his wife. Mermaid was immortal and did the same thing, just so time didn’t dull her feelings.

Once woken, and after he’s used the Disguise Self spell so he looks as he did when he was still alive, Lich is surprisingly friendly and, after engaging in a bit of friendly combat for his own amusement, agrees to help us out.

He won’t give us his ship as he’s still using it, but gives Honest a different smaller one.
He also gives the rest of party magic items or gold to make them go away.

We get an Elemental Airship like the ones used in Eberron, but with extra goodies like an afterburner for boosted speed and the ability to go into space for a week.

I’d mentioned to the DM that Honest’s retirement plans involved making his own dungeons for fun, possibly even a moon dungeon.

This DM is the best DM.

As we prepare to leave, Lich stops us.

He tells us that if we take the airship, an Ancient Blue Dragon by the name of Skyfang will come after us to try and steal the ship. Only reason it hasn’t already attacked is because it doesn’t want to fight anywhere near the Lich's lair.

Offers to help us, but for a price.

He wants us to amuse him.

Offers to put us all through some tests. If we undergo them and reduce Skyfang to half health, he’ll enter the fight himself to help us out. We’re all levels 10 and 11. Skyfang’s challenge rating is 23. We have no choice but to agree.

Each test is designed to show us what would eventually destroy our characters if they didn’t change ways or find a way to resolve the problems we’ve caused.

For Valemon, it is his feud with his family from The City of Brass, and his unwillingness to follow their commands.

For Xagath, his inability to control his followers who dream of betraying him.

For Christabella, her pranks and chaotic nature which had led to her uncle being arrested. In this trial, we failed to save her uncle, resulting in an Androsphinx killing him.

For Tarhan, his feud with the giants and how he was slowly incurring the wrath of The Giant King, the most powerful and tallest giant who’s ever lived.

As for Honest, his trial wasn’t set by the Lich himself, but by Skyfang which the DM had decided best represented Honest’s greed.

Was more than accurate.

Honest isn’t evil. He just loves money way too much.

He’s the kind of person who fills his businesses with almost entirely unpaid interns, will make deals with the worst in the world for a quick coin, and likes to farm monsters such as the Corpse Flower to sell to BBEG’s for lair protection.

As Skyfang approached from the distance, DM gave us time to think up a plan.


Honest and Xagath summon Air Elements to intercept Skyfang and keep him busy.

Valemon gets on a Flying Carpet to circle the ship and prepares to blast Skyfang when it gets closer.

Christabella runs to the front of the ship to use the mounted weapons and blasts Skyfang with a weapon range of 800 feet.

Tarhan pulls out his sword and waits for Skyfang to get within whacking distance.

Things immediately go wrong as Skyfang ignores the Air Elementals and just comes straight for the ship.

Seeing this, Honest bravely and heroically hides in the Captain’s quarters. That turned out to be the smart move to make.

Skyfang starts the encounter with lightning breath. Does 16d10 damage to Tarhan and the ship.
Then lands on the ship and kills Xagath’s Imp familiar, Vom.

Vom dies every game so no one cares.

Hearing loud noises outside, Honest pushes the cabin door open a little and peeks outside.
Sees Skyfang’s rear pointed directly at him.

Shuts the door. And makes sure to lock the door.

Skyfang hears the sound of door locking because why wouldn’t he?

Next round, Skyfang breaks the door down effortlessly because the door is made of wood and Skyfang is made of hate.

Skyfang’s next lightning breath is aimed at Honest.

Does 93 lightning damage, reducing Honest from full hit points to just 5.

I think for a moment.

The airship, which started with over 200 hit points, now only has 30, will crash if something isn’t done.

Honest really likes his ship and has already named it The Honest Ride.

While the next player takes their turn, I check my equipment list and notice something.

The DM likes making homebrew items. One item he let Honest spend money to farm, and so getting an unlimited supply of, was called Funky Fungus.

Eating a mushroom and failing a DC 13 constitution save results in a random wild magic effect happening, centred on the person who ate it.

I get an idea but need to hammer it home with good RP.

Also, on the ship and in the captain's office is Honest’s fiancée. Optimal Luckyfingers, Tiefling Cleric of Mask and mother of Honest's son, Little Con.

Honest likes her because she steals him cool stuff, helps him out with high-level cleric magic from time to time and, based on a picture the DM drew when introducing her with a bunch of other NPC’s, is Thicc with a capital T.

Honest is a very shallow man.

It was probably the DM's plan from the start to get Honest with her as, being my first character, I did what a lot of new D&D players do when playing a charisma character. Flirt with any woman who passes by, though almost always roll low.

The only times Honest has ever succeeded in a seduction roll was with a hag who he ended up French kissing as part of a deal, and the god of evil dragons, Tiamat, by rolling a natural 20. After a while though, Tiamat and Honest decided to just stay friends. 
Anyway, back to the game.

I ask the DM if Lich is watching us.

He said “yes.”

Nodding, Honest turns to Luckyfingers and simply says “go, you’re more important than this ship.”

Luckyfingers takes their son and teleports out.

Skyfang is twenty feet in the air off the starboard bow. 

Honest steps outside of the Captain’s quarters with the bag of Funky Fungus. He shoves all of the mushrooms into his mouth and polymorphs into a Giant Ape, then jumps off the side of the ship and attempts to grapple Skyfang.


As I finished describing all of that, I told the DM that I swallow all the mushroom and willingly fail all my saving throws.

The DM is silent at this. He remains silent for a long time. DM is thinking VERY hard.

Finally, he asks me to roll contested athletics. 

I roll athletics for Honest Con’s Giant Ape form, which I like to call King Con. I only roll a 7, but Giant Apes have the athletics skill on their stat block. Total score is 16.

DM rolls in front of everyone.

Rolls a 2.

Even with Skyfang’s ridiculous strength, he still only gets a total of 11.

The DM is deathly silent as he tries to process what to do. Is silent for 5 minutes straight.

He considers using the Net Libram of Random Magical Effects, a free online list of 10,000 random effects for when magic goes wrong. He’s used this list a few times before and it’s saved characters more than once with lucky rolls. Thought he’d use that to decide on this, but the DM decides that what has just happened goes beyond even using that.

Also considers just killing off Honest but doesn’t. Eventually he decides on something.

“As you swallow all the Funky Fungus, your polymorphed body begins radiating rainbow light which illuminates the entire airship and can be seen from beyond the horizon. As your skin begins to bubble, you feel it melt into Skyfang’s. The two of you are fusing together from the sheer force of magical energy and becoming a single entity.” The DM said.

There is silence from the entire table at this.

“The Lich saw all this, right?” I asked.

“He did,” the DM said.

“He saw Honest telling Luckyfingers, his fiancée, to save herself before possibly sacrificing himself to save the rest of the party?”

“ …he did,” the DM said.

“Is he impressed?”

The DM, being very reluctant - “… yes. As the fusion takes place and you feel yourself altering beyond recognition, time stops. The world turns to shades of black, white and grey, and the Lich appears. He saw everything that happened and not only is he impressed; he’d like to make you an offer. Three options you can choose from which’ll decide your fate.”

This is what the DM finally decided on.

Option 1: Lich will blow up the dragon and Honest. They'll both die but that’ll be the end of combat. The Lich will then take the party and ship to their home safely.

I don’t even consider this option. Honest wouldn’t want to die and I want to keep playing as him for as long as possible.

Option 2: Allow the fusion to continue. Lich doesn’t know what will become of Honest as there’s a good chance Skyfang will survive, but so might Honest, albeit irrevocably altered and fused with the dragon.

Better than option 1, but not by much.

Option 3: Lich can undo transformation. Skyfang will be alive and very unhappy, but so will Honest. Fight continues but Lich will be helping from here on out.

I only have 5 hit points, and the ship only has about 30.

After careful thought, I choose option 2.

“Alright, if you’re sure. How many dice do you have?” The DM asked.

“I’m a D&D player, so a lot.”

“Count them out and then roll 1d4.” The DM instructed.

I do so. “Okay, so I’ve only got 127 dice, times by 3 is… err… 381. Why?”

The DM checks Skyfang’s health, and winces.

“That’s just barely enough. Skyfang’s wings burst off his body and his heart stops. He’s dead and no longer flying. You’re very high off the ground. Max fall damage is 20d6.” He said.

I did say at the beginning of this that DMs never forget what you do.

“I grab him.” Valemon said.

“What?” The DM asked, perplexed.

“I have a hand free, right?” I asked.

“ … sure?”

“I aid him so he has advantage on that roll.”

Valemon had been keeping out of the fight for the most part, but with his Flying Carpet and Belt of Fire Giant Strength, he was the closest to Honest and the best person to try and help Honest out of this mess.

Rolls strength. Rolls High.

“Alright, you’ve got him, but the carpet can’t hold that much weight, so…”

“I take out a weapon to cut him out.” Valemon said.

The DM allows it.

Valemon rolls again.

Rolls even higher than before.

“ … Valemon, you cut Honest out leaving Skyfang’s corpse to fall to the ground far below with a distant thud… This… wasn’t supposed to happen.”


The DM looks like he’s lost something in this game as, by his full admission, he was planning on trying to kill most of us, albeit as fairly as he was able to, but soldiers on regardless.

He goes on to describe that Honest is currently fused to a big clump of dragon flesh and needs to be cut out. Will probably take months to fully recover.

Honest now looks more like a slug than anything, and will need surgery to be less slug like.

Hearing this, Christabella proceeds to poke Honest with a stick as her pet dog runs circles around him.

Her dog survived the battle as we unanimously decided it was immune to all damage due to being too cute.

The DM decides that due to the experience of what happened, Honest’s racial stats have now permanently changed to reflect his new draconic nature.

Now has lightning resistance instead of fire resistance and racial spells replaced by Dragon’s Breath spell and Dragon Roar cantrip.

He also gains a bunch of blue scales on his back, chest, arms and cheeks.

It’s then that I remember that Skyfang is a dragon, along with the one thing dragons are famous for other than being combat monsters.

“What about Skyfang’s hoard?”

“You don’t know where that is.” The DM replied.

“Then I’d like to ritual cast the Divination spell to find it.”

The DM, who’s very much panicked, by this. “You need a hand free to cast that and you’re fused to the dragon.”

“You said I had a hand free to grab Valemon’s, so I can cast it, right?”

The DM looks like a broken man at this point. He goes silent for a final time. Then with a defeated shake of his head ends the game.

It’s several days before he decides on how to handle Skyfang’s hoard as he needs to research Ancient Blue Dragons.

As it turns out, when dragons near the end of their life, they start eating the hoard they’d spent over a thousand years building up.

DM was never going to allow us all the hoard, deciding most was on the other side of the world and some was already digested.

In the end, and after I’m banned from using Funky Fungus ever again, we get a few very rare magic items, 50,000 experience and more wealth then we should ever reasonably have for our level by a long margin.

We also levelled up once.


When your own homebrew magical items backfire. Well played, this was honestly the best quick thinking I’ve heard in a long time.  Please let us know what you think and comment below! 

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