A Minor Heist [One-Shot D&D Scenario]

Dorien Wynter is the first Dungeons and Dragons character I’ve ever created. He’s a 5th edition character –  a level 1 half-elf rogue with a mysterious past, a talent for manipulating people through the art of seduction, a nasty larceny habit, and a full-on alter-ego he can disguise himself as whenever he likes – made with the intention of dropping into an existing 5th ed game that the DM is bringing back after a long hiatus. Though I’ve played a reasonable number of tabletop RPGs over the past 2 years, I’m still relatively new to the hobby, and have never actually played Dungeons and Dragons before, so I wanted to take Dorien for a spin before plunging in at the deep end with a group who are all more experienced players than me, and have played this actual story before (gulp).

M took about ten minutes to prep me a 1-on-1 scenario that he basically made up on the fly. (As such, he asks that you don’t judge him on it, but I consider it impressive for something with no prep and done just to show me the ropes; and I had a blast, which is the important thing!) This gave me a taste of what the game is like and, also, what my partner is like when he stops being my boyfriend and starts being my DM…


I chatted to a shifty elf in a tavern and ended up stealing back an item that was supposed to be delivered to him but the Sheriff had confiscated. I got a great taste of having to roll for way more things than I’m used to; swaggering up to the tavern I fudged a perception roll and tripped up a step, but I managed to style it out, and I also buggered up dodging a coyote and got bitten by it (fortunately, no rabies). I also had a few high stealth rolls, meaning I was like a frikkin’ shadow when I wasn’t tripping over things and taking damage from small, bitey creatures… I really enjoyed it, and now can’t wait to get stuck into something with more to it.

The Game

I was expecting your generic medieval-fantasy-setting, but M had Dorien rock up in a town that wouldn’t have been out of place in the Wild West. It was a small place, and Dorien was in search of adventure, so he headed straight to the tavern – because where else? Complete with swing doors like a stereotypical western, the bar was quite busy for early in the evening. A bunch of humans were scattered about the place, but there was also a group of half-orcs drinking and playing an orc card game, and a shady-looking elf lurking in the shadows.

I headed straight to the bar to order a drink and see if the bar guy had any hints about where to find work in the area. He directed me to a notice board, which had a decent assortment of jobs on offer – woodcutting, mining, something in what appeared to be gnomish – but nothing that took my fancy. I took my drink and went off to lurk near the elf I’d seen when I walked in, leaning against the wall near him.

Part of Dorien’s character is that he speaks a few languages, including thieves cant, so while verbally passing the time with the initially sceptical-looking elf, I took a gamble. In thieves cant, I remarked on the place being full of honest work for honest folk, but that I was looking more for dishonest work for dishonest folk… and he replied. Come and find me later, or I’ll come and find you. After that vaguely unsettling statement, he left the bar through the front door.

I decided against following him, as I was trying to keep a low profile as the newcomer in town, but I had a whole evening to pass. I decided to take a chance and see if I could join the orcs at their game; they were gambling, and I was eager to attempt to relieve them of some of their money. Dorien is charismatic and his persuasion skill is high, so I successfully rolled and was allowed to join them; as half-orcs, they felt that a half-elf knew their struggles with not fully being accepted as a member of either race. I was welcomed, and the drinking began.

I did a sleight-of-hand roll to see if I could get away with pouring some of my drink away under the table, to avoid getting to drunk to successfully rig the game, and I succeeded. Though initially I was losing at the game, which helped endear the orcs to me further, I slowly started to turn it around, and by the end of the evening I was 5 gold pieces up. Due to another successful charisma roll and the general good-natured-ness of the evening, they didn’t mind having lost to me, and we parted ways as friends. I headed up the stairs to the room I had rented for the night from the barman, and lay down to sleep.

True to his word, the elf did find me: he scaled the wall of the building and snuck in through my window like a creepy little bitch. Fortunately I was still awake when this happened, so I wasn’t totally taken by surprise and managed to be cool about it. He informed me that a parcel that was to be delivered to him had been intercepted by the Sheriff and confiscated; as he was already known to the Sheriff, he needed someone who could fly under the radar and get it back. He asked how long I thought it would take me to get it back from the Sheriff, and I told him 2 days – giving myself time to scout out the situation, actually steal the package back, and get it back to the elf. He seemed satisfied with this, and offered me 10 silver pieces for my trouble, on delivery of the parcel. I tried to haggle him up but failed the roll quite badly – I was an unknown entity, he didn’t know me etc – so 10 it was, with mention of future work if I pulled this off. With a last instruction to put an unlit candle on the windowsill if I wanted to speak to him, he left the way he came, and Dorien settled down for the night.

The next day, I decided to utilise one of the tools in my Sneaky Fuckery arsenal: my disguise kit. Rather than donning my alter ego, which wouldn’t be suitable for this scenario, I altered my appearance using the kit so that what I was about to do would be less likely to be traced back to the enigmatic newcomer in the bar the night before. I didn’t do too well on the roll for execution of the disguise, but it was enough that although I would have looked familiar to someone who knew me, it was different enough from Dorien’s usual appearance to throw people off the scent.

After eating breakfast in the bar, I headed across the main street – that is, literally across the street – to the Sheriff’s office.

This is the part where I wanted to start practising the skills needed to have real success as a character in a tabletop RPG. Though I’m confident making in-character decisions and handling any Plot thrown at me, I suck at remembering to look for clues, see what I can observe, and generally hunt down information and hidden surprises; it’s not the way my brain is naturally wired, so it’s a skill I’ve been trying to learn. I told the Sheriff, sat in his office, that I was in town looking for my cousin – a drunkard and a gambler who had once again gone missing – and had the Sheriff seen any layabouts matching that description? As the conversation went on – of course, the Sheriff hadn’t seen the fictional cousin – I got a good look at the layout of the interior. The building seemed to consist of the entrance, the office with a single, unbarred window, and two doors behind the desk with windows set into them. One seemed to lead to a storage area, the other to a corridor with a few cells. Through small talk, I discerned that the Sheriff had no deputy – it is a small town, and he’s the only one here. I thanked the Sheriff for his time, and told him I’d be staying at the Tavern for the next few days if he heard anything.

Once night had fallen and the evening activity in the bar had ramped up, I stealthed out of my window as the elf had done, managing just enough of a success to not make noticeable noise. Rather than just crossing the street in plain sight, I elected to take a scenic route around the edge of town, to approach the Sheriff’s office from the back. This went smoothly baring the aforementioned coyote attack; the little bitey arsehole certainly regretted it’s life choices when I skewered it on my rapier and flung it’s corpse into a bush.

I found that all windows in the building except the one to the office itself were barred. I jimmied the office window open, thankfully getting a solid roll so it was done smoothly and silently, to find the Sheriff, feet propped up on his desk, snoring away inside. In the interest of pursuing the game, and with little to lose, I decided to hedge my bets and stealth inside, fortunately not waking him up. I was glad I’d bothered to take the risk; it was a decoy! There was no one in the building. I started my search in the back room, then the office, but found nothing. I finally headed to the cells, where I rolled low on my searching and ended up leaving a bit of a mess behind as I did so, but I found what I was looking for – a parcel, secreted inside one of the pillows on a cot in one of the cells.

As I snuck back out of the building, I rolled a natural 20 that was enough to carry me like the wind around the edge of town, now mercifully devoid of coyotes, and back into my room at the tavern without incident.

When I unwrapped the parcel, it turned out to be an intricately carved wooden box. I held my breath as I unhooked the clasp and opened the lid, to find… fuck all. It was empty. I rolled to search it for secret sliding panels or something tucked into the lining; nothing. Disgruntled, I carefully rewrapped it and placed an unlit candle on my windowsill as a signal to the elf.

He turned up, he was impressed, I got paid. The scenario was over. Frustrated, I asked M, “So what was the big deal with the box?”

“What do you mean what was the deal?” he said, smirking. “It’s a box.”

“Yeah, but like… is it a special box? Is there something hidden that I missed? Drugs in the lining? A magic box, designed to contain a dangerous magical item?”

He grinned at me, enjoying my frustration. “It’s just… a box.”

Godammit, M. God fucking dammit.

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