Besting a Pit Fiend

Posted on May 11, 2018

A while back, our old adventuring party was involved in a lengthy planes-hopping campaign; gathering powerful magical items before our nemesis could, then searching for the portal to the next world.

One night we found ourselves in an abandoned city teeming with zombies. Fighting them was fun enough, but there were far too many of them to kill them all. We needed to find an escape. We were searching for our way out of this world when our portal finder noted the location of one in the distance at the top of a castle tower. Eager to be on our way to the next world, we pulled out one of our previously found magical items, a shape-shifting blob that could be turned into any mundane item at will, and formed it into a spy glass to get a closer look at the tower.

Passing around the spyglass, we took note of a figure flying around the tower. We knew what the being flying around the tower was, but we were too afraid to say it out loud—a pit fiend. I passed the spyglass to the next companion in our group so he could see for himself the obstacle that stood between us and our freedom. As he pulled the spyglass from his face I looked to him and suppressed a chuckle. Right around his eye, where the spyglass sat a moment ago, was a dark black ring, caused by my turning the spy glass into a trick spyglass before passing it on.

Anyways, we made our way to the tower, and reached the top to find the pit fiend standing before the portal waiting for us, a legion of hell spawn beside it. Knowing we had no hope of defeating him, one of our companions decided to play to the being's nature and bargained with him to let us go safely to the portal—if he could defeat the pit fiend in a thumb wrestling match.

Now our friend was playing a beast of a man, a magically enlarged Human Monk sworn to poverty and wearing nothing more than a loincloth over his manhood, but he was surely no match for the likes of a pit fiend. Our foe, of course, knew this as well, so he readily accepted the challenge.

Out of game, our DM and our friend laughed over the absurdity of thumb wrestling a pit fiend, but decided the easiest way to determine the winner would be to first roll a dex check to pin down the opposing thumb, followed by a str or dex check (whichever was higher), to hold down and/or escape a pin.

They rolled their first checks… the pit fiend won, pinning down the thumb of our Monk.

They rolled again, our friend escaped.

Roll: Pit fiend won.

Roll: Monk escaped again.

Roll: Monk rolled a critical success and pinned the pit fiend for the first time!

This was all well and good, but we'd seen the pit fiend was far too strong and agile to be kept down by our companion. The two rolled again. The pit fiend landed a critical failure!!!

We all stared at each other, in shock over the outcome.

The pit fiend stared back at us, stunned into silence.

We watched the emotions play over his face as he registered what just happened. He was defeated by a mere human in a game as simple as a thumb wrestling. He screamed in outrage and frustration at this turn of events, but grudgingly moved aside to let us pass.

With the pit fiend out of the way, we hurried through the portal, not wanting to press our luck.

Years later, we continue to look back at that adventure. It never fails to bring a smile to our faces when we think of the time our friend defeated a pit fiend in a thumb wrestling contest.

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