Diary of a First Time DM – Chapter 1, Instant Derailment


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I’ve been studying to play or run Dungeons and Dragons for nearly two years, having discovered the game in my late twenties and lamented having not discovered the game when I was in my teens. I’ve recently hooked up with a local gaming store in the hopes of getting my fix, but in the few games I’ve played, I’ve learned two things: one, that I prefer smaller groups, and two, I think I have what it takes to run the game, despite my lack of experience.

With that in mind, I finally, after weeks of cajoling, managed to convince a long-time friend of mine to play in a D&D game, a starter adventure I’d whipped up the night before; a maze-like tomb, full of treasures and traps and tricksy monsters, that would teach him the rules of D&D.

He played a triton divine soul sorcerer called Aquilla, that I’d built for him based on a video game character he’d made in an unrelated game, and I played his bodyguard, a towering hulk of tiefling muscle, simply called Demon, as it was just the two of us at the table and I needed to keep his squishy character alive. He claimed his sorcerer was neutral good, but he played the character much closer to chaotic neutral, which I’d expected as we’ve known each other for years.

We start in the tavern, where so many stories begin, and he’s already into the story telling and world building, insisting that his character recently “won” some gold from another guy at the inn, which I allowed; it’s all backstory at this point. Aquilla is leaning back with his feet on the table, toying with his new coins, while his bodyguard is just standing nearby, conveniently convincing the men at the far table not to confront him about the gold.

Aquilla is dressed richly and gaudily in navy blue with gold brocade, and so attracts the attention of a portly man in equally gaudy purple and silver, who wants to hire him for a job. Aquilla doesn’t ask many questions, but agrees to the man’s request before promptly stealing one of his rings during the handshake.

As we were playing somewhat casually, I didn’t have access to dice at the beginning of the session, but rolled retroactively to see if the man noticed the sleight of hand, and the sneaky triton pulled it off (both metaphorically and literally) so portly man didn’t even realise the ring was gone. And so began my friend’s D&D career, and mine as a DM.

Aquilla retired for the evening, taking the best room at the inn for himself and partaking in some of the… “local entertainment”… before heading to the stables in the morning to go on his quest. The portly man has his horse and cart ready and Demon is already sitting atop every edgelord’s favourite horse; a black stallion with a red mane, and Aquilla, not wanting to appear lacking, decides to pass off one of the inn’s horses as his own, and tries to mount a grey and white stallion.

Nat 2 Animal Handling with no modifier, so he’s on his butt on the other side of the horse before he’s realised what’s happening. Portly man just laughs it off and invites him onto his unnecessarily lavish cart, his ego at least sated by Aquilla’s flop.

We skip to the tomb, the arched entrance framing a heavy iron door, hidden in the back of a small cave. Portly man sets up a picnic near the entrance to the cave and waits for Aquilla to return with the treasures inside.

Aquilla notices a stone structure to the left with another heavy iron door in it, though this one is locked and inaccessible. This was meant to be the secret exit to the tomb with easy access to the central chamber, that he would use to escape the maze once he’d retrieved the treasure. He’d need the exit after dealing with all the traps and monsters inside the tomb.

If you can see what’s coming, then you have better gaming senses than I do.

Aquilla tries the door, but it’s too heavy and there is no visible lock, so over comes Demon. Demon has a 17 strength and a seven-foot-tall bodybuilder’s physique, so I reason that he’s got a shot at opening the door, but would need a near superhuman effort to actually get through the-

Cue my friend’s first natural 20. I hadn’t actually set a DC and just reasoned that Demon was strong enough to do it, and so boom, over an hour of maze sculpting the night before has just gone down the toilet, and the hour or so I hoped it would take to actually complete the dungeon, lessons, treasures and combats included, would not be happening. I needed a treasure and I needed a boss fight, and I needed it right at that moment.

Aquilla found himself in a long underground corridor to one of the tomb’s many secret staircases, and then another long corridor inside the tomb itself, curving in towards the central chamber. He can hear voices up ahead and makes his first stealth check, rolling high enough that he manages to get to the chamber unnoticed. Inside are four thugs, and listening in on their conversation, they’re the same men he “won” his money from before. Seems they managed to get there first and were lying in wait, hoping to get their coin back, one way or another. Aquilla immediately assumes treason from the portly man outside, and, in a fit of rage, storms into the chamber and demands answers, taking the men by surprise, but also forgetting that he has a total of 8 hit points and that he hadn’t bothered casting Mage Armour before entering the tomb, and so when combat begins, he’s fourth in initiative order, and already in serious trouble.

A thrown dagger gashes his shoulder and a suddenly panicking Aquilla turns and flees back into the dark corridor, grateful for having access to Cure Wounds as he quickly gets his HP back, and just as grateful for the monster that is his barbarian bodyguard as he charges the men and cuts one in half with his great sword. The leader of the group of thugs calls Aquilla a coward for running before attacking Demon, while the last of the group chases Aquilla into the corridor and puts another dagger in his shoulder. Now pissed, Aquilla pulls out a small diamond and casts Chromatic Orb on the thug, who realises too late the danger he’s in and tries to run. Aquilla covers the poor sod in magical acid, leading to a slow but certain death on the floor of the chamber. Demon meanwhile is still on the warpath and hacks down the leader of the group, bisecting him with ease, leaving only one man alive. The poor thug looks up at Demon, then at his two butchered friends lying at his feet, and his other friend slowly sinking into a pool of his own entrails, and drops his dagger, begging for mercy. Aquilla demands answers, wanting to know what he’s doing there, but the thug insists that they’d overheard him talking to the portly gentleman and decided to lie in wait there. All they wanted was payback for losing their gold in a game of cards, and that it wasn’t supposed to go the way it had. Aquilla decides to let him go and the thug flees back into the maze.

As the party of two spend an hour recovering from their wounds, Demon searches the bodies, though he only manages to collect ten gold thanks to a poor Investigation check, and Aquilla inspects the treasure; a large golden gauntlet with a large glowing blue and pink gemstone in the back. He decides to put it on and attune to it in order to figure out what it did. Whatever it does though, it’s clearly worth a lot more than the one hundred gold the portly man had offered to them in exchange for their help, and Aquilla decides to keep the treasure for himself.

Exiting the tomb the same way they came, the two of them find the portly man sleeping against the wheel of the cart. Aquilla isn’t done screwing this guy over yet, and so decides to steal his horse and cart as well. However, both Aquilla and Demon fail their Animal Handling checks, leading to the horse panicking and bolting, dragging Aquilla and the cart behind it out of the cave and into the world outside, leaving his startled employer behind on his picnic blanket. Where they go from there is something I’m going to have to work out.

All in all, I’m happy with how the session went. It felt good helping my friend go on his first D&D adventure and I’m looking forward to formally getting behind the DM screen. True, things didn’t go as I’d planned; the entire tomb was skipped over by a lucky roll and I scrambled to come up with a boss fight on the fly, and the treasure I created is WAY too powerful for a level 1 Sorcerer, but I think I can still make it work. Besides, I was gratified to find that the 10HP and 12AC I’d given the thugs was right on the money for the bandit stat block in the Monster Manual, so I feel confident that with some actual prep time in the future, I should be able to handle anything my players throw at me.

I plan on trying to get my friend to come with me to the game store so I can get more players into my game and actually have an adventuring party, and I’ll post further adventures here if, or hopefully when, they happen.

The reign of Dungeon Master Kingpin has begun!!


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  1. Aaaand then corona happens… here I am, trying to start a D&D game and become a DM and really proud of my first game and first diary the I have a dozen plans for the future, and then nature itself decides to say “Thou shalt not play D&D”… prft…

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