DND Stories: That one time I played D&D with my boss.

Oh, boy. This is the craziest of the DND stories I’ve told so far… possibly. It all started back in college when I was delivering pizzas to make money on the side. I was living with a few friends just off campus in a dilapidated house in the nicer part of town, which we lived for free, because I’m incredibly lucky.

We frequently played Dungeons & Dragons in the basement at that house with Anastasia as the DM. Unlike my DM from my teen years, Anastasia liked combat. A lot. She was a big fan of the fight scenes from the movie Conan. Personally, I loathed these combat-focused D&Ds, but I kept coming back for her.

One night, I had off work and was in the basement with Anastasia, Chuck, and my other friend, Mike. We were getting ready to start a new campaign, which is what we always did after Christmas break at college. Anastasia had her books and miniatures set up on the piece of plywood that served as a table in the basement.

I was planning on playing an elven wizard and Chuck was playing a tiefling healer. Mike was playing a fighter.

We were gathered around the table, waiting for Anastasia to begin when Mike had to use the bathroom. He asked if someone could watch his character sheet while he was gone. Like the idiot I am, I volunteered.

Before Mike left, Anastasia pulled him aside and talked to him. I didn’t hear what she said, but I could tell she was urging him to use the bathroom before we started. He agreed, said he’d hurry back, and took off. At least that’s what I thought they talked about.

While we were waiting for him, I got a text message from Harold, my boss at work. The pizza place was shutting down early because some drunk frat boy had drunkenly climbed into the oven and almost died.

“Shit, man,” I’d texted. “Are you okay?”

“Not really, Paul. He was messed up pretty bad.”

“I’m sorry, Harold. Hopefully he’ll be okay.”

“Yeah… I hope so, too,” he sent back.

Harold had never been particularly friendly with me, but I liked him a lot. He was one of the few male leaders I looked up to because he was kind to me and treated me with respect. If I could be half the man he was, I’d feel proud for myself.

“Is everything all right, man?” Chuck asked, leaning over my shoulder.

I looked up at him. “What? Yeah, sorry. I’m just a little worried about Harold.”

“What’s wrong?”

“Some drunk frat punk climbed into the oven…”

“What?” Anastasia peeked from behind her DM screen. “Are you serious?”

“Yeah. He was on fire when he got out of there. Harold’s probably traumatized for life.”

Suddenly, something moved behind my character sheet. Naturally, I assumed it was Mike, who had just returned from the bathroom. I moved to the side, so he could take his seat.

As I did, I noticed my character sheet doing something I’d never seen before: it was beginning to breathe. I stared at it for a moment, stunned. Then I blinked a few times and stared at it some more.

It was still breathing.

“Are you okay?” Anastasia asked me from across the table.

“What?” I brought my attention back to her and the table. “Oh, yeah. Yeah, I’m fine. Just… I’m fine. Harold’s just worried about the cook.”

She nodded then disappeared behind her screen. We went about the business of getting ready for our first session. Mike was back by now, saying something about his character sheet smelling like the bathroom. Chuck looked at the sheets and said they didn’t smell like anything, which was true.

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I was still trying to figure out how my character sheet was breathing.

After a few moments, Anastasia had everything ready to go. She leaned over the table and asked, “Are you guys ready to start?”

I looked at the table. My character sheet was still moving. It was like a snake, its tongue flicking out of its mouth.

“Yeah,” Chuck responded. “We’re ready.”

“Okay then,” she continued. “I’m going to set the scene…”

Before she could begin, a loud banging on the front door upstairs startled the hell out of me. I jumped out of my chair and clutched the table for support.

“What the hell is that?” Anastasia said.

“Probably the wind,” I said. “This place is falling apart. It’s probably just a breeze that slammed the door shut.”

“Okay, Paul,” she said. “Just take it easy. If a breeze slammed the door that hard, it would’ve blown you off the chair.”

“I guess,” I said to her. “Just the wind.”

“Are you sure?”

“Yeah.” I nodded.

I was still staring at my character sheet, which was still moving.

“Are you sure?” she repeated.

“Yeah, I’m fine.”

She glanced at me for a second, then went back to her screen and started setting the scene. Before she could finish, the knock repeated.

“Yo, that’s someone at the door, man, Mike said. “I’ll go look.”

He stood up and started up the stairs.

Anastasia and I looked at each other. “I’ll go with him,” I said, standing.

Anastasia as her favorite NPC…

I followed Mike up the stairs and into the living room.

We heard the knock a third time. “I’m gonna go see who it is,” Mike said. “You stay here.”

I nodded. He went to the door and opened it. Harold stood there, a bottle of Jack Daniels in his hand.

“Oh, hey, Harold,” I said.

He’d been over to hang out a few other times, but I’d never seen him look so shaken up.

“You guys have any beer to go with this?” He raised the bottle.

“I’m sorry,” I said, “but I think Anastasia’s downstairs with Chuck. We’re in the middle of a game.”

“Oh, fuck.” He slumped against the wall. “Sorry to bother you guys, but I just wanna get drunk.”

“Come play with us,” Mike offered.

I shot him a look but didn’t say anything.

“Yeah. I’ll do that. Just give me one second.” He took a swig from the bottle. “Let’s go.”

We led him to the basement. He was in good spirits, but he was a little sloppy walking. We got down the stairs, and when Harold saw the table, he smiled.

“Oh my,” he muttered. “I haven’t seen a set-up like this since I was in college.”

“We’ve got a fourth player,” I said.

Anastasia took it in stride. “That’s perfect. Everyone sit down.”

Harold sat down. I took my seat next to him. Thankfully, my character sheet wasn’t moving anymore.

Over the next hour, as Anastasia led us in a rip-roaring adventure, we gradually explained Dungeons & Dragons to Harold. At first, he wasn’t interested. He hadn’t played in years, but he was eventually pulled into the game. We were having a blast. Harold, who was really the only drunk I’d ever met that didn’t get mean and angry, seemed to be enjoying himself.

Halfway through the game, Harold announced his character was going to drink a potion of some sort.

An NPC – some strange race we’d never met before – was standing next to Harold. He was playing a female gnome bard to be specific.

“You have an urge to press the button in the workshop,” Anastasia said.

“Who me?” Harold asked.

Anastasia nodded, just the top of her head showing over the DM screen.

“I press the button…” Harold slurred.

“Do not be pressing the button!” Anastasia practically screamed in an accent that cracked me up.

It sounded like a mix between a Jamaican dragon and a French pirate.

“Give me some dice. I press the damn button!” Harold insisted.

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“Do not be pressing the button!” Anastasia repeated in the voice that would become a meme to our group.

“Give me some dice. I press the damn button!” Harold said again.

“Do not be pressing the button!” Anastasia said again.

“Give me some dice. I press the damn button!”

“Do not be pressing the button!”

“Give me some dice. I press the damn button!”

This continued for longer than I think any of us expected. We were all laughing so hard we couldn’t stop. Anastasia wouldn’t let Harold press the button, and Harold kept insisting he’d press the button. Finally, Anastasia had to give in.

“Fine!” she yelled.

Harold rolled the dice. He rolled a natural 20.

“Did I press the button?” Harold asked.

Anastasia just stared at him.

We were all silent for a moment. A rush of cold air blew through the room.

“As you press the button…” Anastasia had us all drunkenly on the edge of our seats. “…a loud rumbling sound echoes through the room. It sounds like a machine of some sort – a large machine. It sounds like gears turning, like a massive engine, and it’s growing louder. Then, suddenly, a red light shines down from the ceiling at the far end of the room. It’s a light that you can feel, that you can sense in your bones, and it’s getting closer and closer. It’s almost like the light is growing. The light is becoming more intense, it’s almost…”

She stopped talking and stared hard at Harold. “Roll 10d4.”

I scrambled to get the appropriate dice in front of Harold, wondering what was going on.

“Roll 10d4.” Anastasia said again.

Harold started rolling, and as he did, I saw Anastasia grin.

“Eighteen,” Harold muttered.

“The light is becoming more powerful, and you can see that it’s not a light at all, but a blinding ray of red energy. It’s a ray of pure energy that’s emanating from the eye of a small red dragon.”

“Oh no,” Harold said, the grin fading from Anastasia’s face.

“As the light comes closer,” Anastasia went on, “it becomes more intense, and you can feel the heat from the red dragon’s eye. It’s so hot and so powerful, it’s almost burning you, and it’s getting closer and closer. You can feel the heat, you can feel the pain, you can feel the burning…”

“I unpress the button. I unpress the button!” Harold screeched.

At this point, we all lost it and any semblance of a normal Dungeons & Dragons session faded.

We helped call a cab for Harold (I’m aging myself here!), then all went back to crash.

As I fell asleep that night, I wondered if I’d see Harold again, but I also wondered why the hell my character sheet was moving.

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But that, my friends, is another story entirely.

Until next time, thanks for reading my DND stories…

Paul Bellow

LitRPG Author Paul Bellow

Paul Bellow is a LitRPG author, gamer, RPG game developer, and publisher of several online communities. In other words, an old school webmaster. He also developed and runs LitRPG Adventures, a set of advanced RPG generators powered by GPT-3 AI. Here at LitRPG Reads, he publishes articles about LitRPG books, tabletop RPG books, and all sorts of DND content that's free to use in your personal tabletop campaign - i.e. non-commercial use. Enjoy your stay and reach out on Twitter or Discord if you want to make contact.

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