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StoryTellerBob comments on The devil challenges you to a game for your soul, what do you choose?

“Dungeons and Dragons, eh?” The devil cackled with laughter.
“But… I am the Dungeon Master.” The devil’s grin soured as he plucked a pen and paper from the folds of his robe.
“Fine, but when I beat your campaign your soul will be mine.” Johnny nodded in agreement and the two took their seats, only a few sheets of paper and a pair of dice between them.
“You are an adventurer who has been captured by the dragon lords of Blackhollow. The dragons keep you locked in a cell where you await your execution for trying to trespass in their sacred halls. You must escape Blackhollow to win the game and my soul, but you must also kill the Vath, the king of the dragons, or he will not stop hunting you until you are dead. You awaken in your cell mere hours before the execution is scheduled to take place wearing nothing but a loin cloth. Through the bars of your cell you can see a huge, dimly lit hall with rows of pillars stretching into the seemingly infinite darkness outside.”
“Alright, let’s see… I search the cell for hidden passages.”
“You search the cell thoroughly for an hour, but you find nothing.”
“Fine, what about the lock? Maybe I can break it open with a rock or something.”
“You give the lock a good bash with whatever pebble you can find on the ground, but it’s made out of the finest steel, forged in dragon fire and you don’t even managed to put a dent in it. You are running out of time”, Johnny said and smirked at the devil.
“I’m not done yet. I, uh, bang on the bars of the cell, shouting for a guard.”
“After a few minutes of making a racket a huge, thundering quake shakes the ground beneath your feet. Through the darkness a scaly black dragon emerges, his wings easily spanning a hundred feet. He stops in front of your cell and fixes you with his gaze, puffs of thick, black smoke spiraling from his nostrils. ‘What do you want, puny mortal?’ The dragon asks, the force of each word shaking the walls around you.”
“Okay, I want to persuade it to let me go.”
“You can’t do that. You defiled the sacred halls of his ancestors, he wants you dead, there’s no way that’s going to work.”
“Well, you can’t make an impossible to beat game, that’d be against the rules.”
“Alright, fine, you can do a persuasion roll, but you get a -10 because he wants to kill you, a -5 because it’s hard to persuade someone when you’re wearing nothing but a loincloth, -5 because the dragon is in a particularly shitty mood today and why not just throw in another -10 because he would break the laws of his people if he let you go and would most likely be executed himself. So there, you’ve got to roll a 38 on a D20. Like I said, there’s no way that’s going to work.”
“Isn’t a natural 20 always a success though?”
“Yeah, sure, but if you fail he will be so insulted that he will burn you to a crisp on the spot.”
“Alright.” The devil smirked and took the dice in his hand, rolling it in his hands and blowing on it for good measure. “Watch and learn, watch and learn.” He send the dice flying across the table and when it clattered to a halt a burning 20 facing up.
“Boosh! Natural 20, baby!”
“Fine, the dragon takes pity on you and decides to stay and hang out for a while. The two of you shoot the shit, grab a couple of beers and just talk for a while. His name is Steve and he works at the grocery store, but that’s just temporary until he makes his big breakthrough in his acting career. Unfortunately, when you ask him to let you go, he says you seem like a cool guy and he totally would, but he doesn’t even work here, he was just passing through when he heard you making a ruckus.”
“Oh come on, how is that even fair?” The devil complained.
“All is fair in love and D&D. Anyway, now the real guard-dragon shows up and drags you out of your cell. He marches you through the dark hallways out into a huge amphitheater where the councilors of Blackhollow have gathered to watch your execution.”
“Don’t I get a trial or something?”
“Okay, fine, but you’re totally guilty and everyone knows it.”
“I demand a trial by combat.”
“Wow. Really? Okay, I guess. The dragon king Vath sits at the head of the council and he agrees to your request. The dragons send forth their champion, Eussath, a dragon so large and menacing that he makes you wonder if Steve was a dwarf or what the deal is. He lets out a roar that shakes the amphitheater and the other dragons join in. You are still unarmed, basically naked and have no weapons or magical abilities. What do you do?” Johnny smirked to himself, thinking he finally had the devil beat.
“I want to disguise myself and sneak out.”
“Disguise yourself as what? The only creatures there except yourself are dragons.”
“So I disguise myself as a dragon.”
“…”
“Yeah, yeah, I know, only a natural 20 works, got it.” The devil cupped the dice again and blew on it before dropping it, once again rolling a 20.
“That’s cheating!” Johnny pointed at the dice in disbelief. “There’s no way you just rolled 20 twice in a row!”
“You learn a thing or two about dice, playing games for souls since the beginning of time, Johnny-boy.”
“Whatever. Okay, you disguise yourself as a dragon. Somehow a whole group of dragons mistake you for a 80 feet tall fire-breathing monster with scales harder than steel instead of a half naked human. They’re all terribly confused about where the guy they were about to kill went.”
“Okay, let’s get out of here.”
“You still have to kill the dragon king to win.”
“Crap, I forgot about that. Alright, I walk up to the king and punch him in the face.”
“Alright.” Johnny let out a heavy sigh. “Just roll.” He buried his face in his hands and sure enough, a moment later the devil let out a triumphant squeal.
“Natural 20!”
“Okay, your fist connects perfectly with his jaw, but his scales are so thick that he doesn’t even notice you hit him. You can’t kill a dragon with your fists, man, that’s like, D&D 101.”
“Maybe you can’t kill a dragon with your fists, but I have a plan. I let my dragon disguise drop and when the dragons all drop their jaws in surprise, I jump into the kings open mouth.”
“That kills you. Getting eaten by a dragon kills people.”
“No, see, I jump past his teeth and dive down his stomach!”
“… Fine.”
“And now I punch him from the inside. No scales here, bitch!”
“Okay, you punch the dragon king for two points of damage. He’s got 80’000. The dragon feels your punch this time, although just barely, and decides to breathe some fire. A giant fireball forms in his stomach, where you are, and burns you to a crisp. There’s no way to run or escape it. You are dead.”
“You can’t just kill me without even giving me a chance to roll or anything, what kind of bullshit is that!”
“You jumped into a dragon’s stomach, what did you expect, you idiot! Still, I suppose I should give you another chance. When you die, you’re greeted by the devil. He tells you that he will play you in any game and the winner takes your soul.”
“Alright, my game of choice is one where the least powerful of the two wins. If he wants to win, he’d have to make me more powerful than himself, in which case I can take my soul back with force.”
“Damn, why didn’t I think of that.”

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