So back a few years ago, a friend of mine and I gained a small bit of interest into dnd, I think it was around the time the critical role stuff came out but I can’t remember for certain. Our parents didn’t buy it for us though because satanism, witch craft, the usual reasons. So in response my friend made his own version (which we later found out was just homebrew) with “unique” races and classes and such, but it ultimately ended up being like Skyrim turned into a TTRPG.

We still enjoyed it though and gathered a few small tales to tell. We ran about 3 or 4 campaigns since his approach was very similar to a sandbox campaign where as long as you rolled high enough, it was technically possible and therefore in the game.

I bring that up because in one campaign I was playing a mini-giant knight, pretty much his op class and race for strength, and upon a quest I found some chains in a dungeon, which I kept for scrap initially. However I got curious and asked him if I could turn it into something like a flail or something, where I attached two boulders, one to either side, and swung it around. He allowed it and soon enough, I had an improvised weapon that was better than anything he intentionally put in the game.

Well later on in the story I was helping this kingdom which was at war with goblins. He sent me on a naval fleet with the rest of his men to try and deal with the goblins, roll to hit: nat 20.

Swinging my chained boulders around like Kratos’s chaos blades I wrecked all of the enemy ships and all of the king’s ships. I returned to the king and rolled a nat 20 when confronted on why his ships were destroyed. I simply told the king it was the goblins that did it, explaining the battle in vague detail that seemed to satisfy the king.

As a result, I was made a naval commander and given a reinforced fleet to return to the war. That was about as far as we got until life happened and split us up a bit, but I always think back to that and the other campaigns and how much fun it was with him.

In a different campaign with him I played a khajiit monk, which in his version was just a way of the fist monk. He played a blacksmith and another friend joined who I’m gonna call Kevin, playing a ranger.

Nothing particularly interesting happened at first outside of the encounters, but at the start my friend would roll nat 20s outside of combat like his life depended on it and in combat he would constantly roll 2s and 3s (in his game if it was above 12 or so it hit, 20s were critical, and 1s came back and did 1d4 damage to the player who rolled)

At the beginning my cart broke down outside of a town, leaving me to wander in to find someone to fix it, where I met the ranger and the blacksmith. The blacksmith offered to try and fix the wooden wheel but made no promises. Roll d20: nat 20.

Not only did he repair the wheel but it was fully reinforced. I guess to make things more interesting or whatever he rolled to try and put the wheel back on, and another nat 20. Puts the wheel back on perfectly.

At this point we were cracking up like Game Grumps in their ps1 wheel of fortune video and talking of checking his dice to see if they were weighted, but we got into an encounter. We had a bit of a smug feeling since our heavy hitter of the party rolled 2 nat 20s back to back. He goes to roll, nat 1.

Kevin and I took out the enemies before setting off to find out why they attacked us. My friend, trying to add realism, had us long rest and went to forage for food (there was no food mechanic, just padding) rolling, you guessed it, nat 20. We joked about it being a Golden Corral style buffet of food just waiting for us.

That was about the end of his insane luck out of combat but it didn’t really improve in combat either, but we still had fun and occasionally I’ll remind him of some of those.

TLDR: a couple of short campaign stories from a homebrew session years ago involving an op improvised weapon and insane nat 20s during inopportune times.