What I Learned Playing D&D for the First Time as Dungeon Master

I had never played Dungeons & Dragons before even though I knew of it from my middle and high school years. Something about growing up in the late 80s and being a teen in the early 90s made knowing about D&D just base-knowledge. It’s like how I’ve never read a single proper superhero comic but know most of the most important stories for most of the DC and Marvel universes. It’s background noise.

With the resurgence of D&D and now an adult with a home, I though it’d be fun to give it a go. I posted an innocuous status update on Facebook saying I was interested in playing, got several responses from my local friends, and made a FB group (The Casual Gamers). Our initial group consisted of three experienced players and two who like myself knew of D&D but had never actually participated before in any way. I volunteered to be the Dungeon Master thinking it might be a good way for me to motivate myself into finishing my fantasy novel series.

It took nearly nine months to finish this first campaign.We began playing in early November of 2017 and finished in late July 2018.  It was a fun endeavor. I’m now turning over the DM-ing duties to another player in the group. He’s kept the same setting but created a huge city modeled after Terry Pratchett’s Discworld city Ankh-Morpork he’s calling New Adtham.

I’ve learned a lot during this time gaming as a DM. I’ve discovered I kinda love building models and sets, collaborative storytelling is wonderfully fun, and I’m slowly warming up to the idea of a more visceral or active roleplaying. But I think the top ten things I’ve learned from diving in and running the game are the following:

  1. You can’t force players to play the way you want. 
  2. No matter how detailed and prepped you are, you won’t use it all. 
  3. You will have to improvise nearly every game night. 
  4. There always needs to be a balance between fighting, roleplay, and puzzling. 
  5. Patience is vital.
  6. You got to have a great poker face. 
  7. Rewards are their own reward. 
  8. Players need a sense of purpose, of direction even just for the sake of ignoring it. 
  9. Rules as Written and Rules as Intended are trumped by Rules as Played
  10. Consensus makes everything easier and more fun.

Now this weekend I will embark on my first time playing D&D as a player. I’ve got a character rolled and fleshed out. Hopefully, I’ll survive…


The Backwater Gambit


The Plot

The players wake up in prison cells. The last thing each remembers is falling asleep in safety. The first task the players have–get out. As the party of adventurers make their way out of the Usurer’s Tower to the nearest village they soon discover strange things going on in the county of Larrissone. This area is extremely remote. It takes a few adventures before the party discover they are on the distant continent of Osse (most had come from Faerun). So, in a backwater of an unknown continent, the party discover witches, a drow conspiracy, a gnoll and hobgoblin army, a city on the brink of collapse, and a corrupt church.


The party discovers at the end of the campaign who is responsible for bringing them to the county. By the end, they are high enough level to free the county from the magical threats plaguing it.

But a quick sketch–

Over a 150 years ago, a human warlock came to the region from down river most likely the massive city of New Adtham. Founding the villages and naming the county, he attempted to build a safe haven where humanoids of all kinds could live in peace. This was primarily inspired by the fact that this warlock had as his betrothed a drow priestess. The two had a vision of the drow living above ground, out of the Underdark and out from under the wicked control of the goddess Lolth through the protection of good drow goddess Eilistraee. 

The warlock named himself ruler taking the title of Margrave. He ventured to the three Corse Ruins (temples and settlements originally built by native Osselanders but abandoned centuries before) where very powerful lamias had taken up residence. He defeated each stealing their accumulated magical wealth and imprisoning all three into a single ruins. These lamias became known as The Sparing Ones. Their only desire was to wait, build their power and influence, and escape the ruins to rule over the county again.

After this victory, the margrave intended to marry the drow priestess. However, Lolth discovered the plot of the two striking the priestess down and turning her into a drider on her wedding day while killing the margrave. With the county now populated but ruler-less, it limped along as best it could with most of the margrave’s wealth and magical items scattered and hidden throughout the county. The settlement called First Town gave way to the small city of Bas Eldritch where a Pelorian monastery was built upon the foundation of the margrave’s library. In Bas Eldritch an uneasy alliance between the religious leaders, the City Guard, and Merchants’ Guild developed. Outside of the city, the villages of Foxon and Monton managed to just barely hang on through farming, mining, and thin trade.

A hundred years have passed since the disappearance of the margrave. Mysterious and magical forces are gathering in the hopes of taking control of the people in this small, rural backwater. However, there is a divine presence who is attempting to keep the county free and push back against corruption. That presence has brought in outsiders to foil the machinations of evil witches, beasts, and humanoids.


Sets & Minis

All the players in my campaign had miniatures made of their characters through HeroForge. The minis were fun and I looked into getting my own for the adventure. However, I’ve hardly the income to spend. This is when I stumbled upon the paper minis offered through DriveThruRPG.

So, I picked up a few free models and some modestly priced ones spending about a week to create my first setting for the campaign–the town of Monton, which saw a two part battle.

I then used some plastic chess pieces I was given as child from my parents when we lived in Germany which turned out to nearly perfect scale to the minis the party had. This setting worked very well and only increased my desire to make more settings. The paper models turned out to be a wonderful, inexpensive way to augment gaming. Some of the other ones I put together were a ruins, 


a handful of boats, 


and some wagons with supplies.


These buildings and minis now reside in my office closet alongside two other sets I created. One of which I called The Gauntlet,

and the last set I made for the face-off against Kolo Illrym,

To populate these sets I was able to get access to a 3D printer and through free files via Thingaverse make a bulette, drider, treant, and two shield guardians.

These combined with the pewter drow I purchased (and did a mediocre job of painting) and the goblin minis I bought from my local gaming store, made for my set of baddies. I made these sets so the players would have an occasional treat. However, I’ll be honest, I kinda want to keep making more and more miniature settings.

On our last day of the campaign, I didn’t have any thing created but I did try to find some neat looking paper cutouts to serve as the opposition. The last battle took nearly six hours but I think it was a worthy end…


My Favorite NPCs

Making characters is fun. In fact, I think I do it a bit too much. Of the non-playing characters (NPCs) in my campaign, a handful I really liked and may attempt to bring back into future campaigns or even flesh out as characters for me to play. Each NPC I created was meant to fit a role in the story, and after I rolled their numbers, I went looking through Pinterest to see if I could find some images that would correspond to what I had in my mind’s eye.

Alice ‘Grim’ Donovan


Grim was the leader of The Inquisitors, a troupe of witch hunters. She was my first attempt at a badass character. In the party’s first encounter with her, she and the group’s rogue nearly came to blows. In fact, it was only a poor DM role that kept the rogue from literally getting his throat cut. 

Alice ‘Grim’ Donovan, witch hunter, is the de facto leader of a band of outcasts devoted to one goal–the eradication of the evil that ruined each of their lives. For Grim, that evil was a witch who tried to bring her village under its control by killing or tormenting the elders. She lost her family when they displeased the witch, and it slaughtered them. The town, rather than standing up to the witch, refused to fight driving the young Alice into a rage. She plotted and hunted the witch, eventually trapping and killing it. Young Alice brought the witch’s body back to the village, hung it up in the center of the hamlet, and set it aflame before everyone as she stared them down covered in soot and blood. Her face never betrayed any emotion earning her the name ‘Grim’ from that day on.


Talice Quavael


She only appeared in a side quest, but the Drow Talice Quavael was a character I really enjoyed making even though she had only the small role in the campaign. Talice served the function of revealing to the party the identity of Kolo Illrym and giving them the first inklings of his larger scheme for the county. It also gave me the opportunity to set up the reveal the setting of the campaign–the continent of Osse–by establishing the story within Forgotten Realms lore and geography (1494 DR).

Talice came from the Underdark Drow city of Ust Natha, one of the many cities Kolo has been recruiting. However, arriving in Larrissone turned out to be less than she expected leaving her wanting to go home. Unfortunately, Kolo doesn’t look kindly upon those who want to leave his fold. She barely escaped and bears the fresh scars to remind her.

She is looking for a way to return to Ust Natha and believes she has found a way. Within the ruins of the great estate maze the last margrave of Larrissone built, there is a magical forge where Kolo’s underlings are crafting teleport pads and portals.


Swith Masmond


Although Karen turned out to be a more significant component to the story with a rather big reveal at the end, it was the mayor of Monton Swith Masmond that I had the most fun role-playing. Swith was a mix of Futurama‘s Zapp Brannigan and Seinfeld‘s J. Peterman. However, Swith was a hero. During the Battle of Monton, he sacrifices himself to allow the townspeople shepherded by Karen to escape the gnoll and hobgoblin army. I had intended to bring him back into the narrative but the party never really made it back to an area where he could come into the plot again. Yet I like to think Swith is still out there.

Masmond is dressed in overly elaborate clothing of many layers. Tall with an impressive upper body, he has a severe looking scar down one side of his face and closely cropped silver-white hair




Another character who only saw limited campaign time was the half-orc fence, Zur. I actually had a couple of storylines involving Zur which would have brought the party into Bas Eldritch a lot more smoothly than how they did but the group never really bit on any of my in-game pitches. Zur was the first multiclass character I made, a mix of bard, rogue, and cleric. He was meant to be the guy who could move your merchandise, the guy who knew a guy. I may rework this character to be one I play some time in the future.

Zur is a fence for much of Edda Taisi’s supplies when they arrive in First Town and when he has to move product discreetly in Bas Eldritch.




Finally, there’s the street urchin Wand, a native Osselander, who was once a wizard’s apprentice. I had written Wand as a nonbinary character, a kid (8-10) who you couldn’t tell the gender of. I wanted to have a character that had a good amount of secrets but was looking for the right people to trust. Wand turned out to serve as primarily a guide for the party through the city of Bas Eldritch.

Wand leads the party through the tunnels answering the party’s questions about what’s going on in Bas Eldritch.

Wand gets their name from the the Wand of Wonder they wield discovered while exploring the catacombs of Bas Eldritch. The party never felt comfortable using the Wand of Wonder, which kinda bummed me out. But I still like the character. I had made Wand a wizard/rogue to fit their current situation, and I think I may reuse the character in the future, perhaps a bit older.





2 thoughts on “What I Learned Playing D&D for the First Time as Dungeon Master

Leave a Reply to danielwalldammit Cancel reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s