One time while playing D&D we were fighting a dragon in an underground water temple and I was trying to get somewhere safe, so I sarcastically said “I’m going to use my stealth to crawl inside the dragons ass!”
Then my dm called me out and said roll for it…
I had a low stealth, so naturally I was like “Fuck…”
But I nat 20’d and my dm told me to roll again and once again… Nat 20.
My dm let out an audible sigh and said “you are now inside of the dragon… I hate you…” And then I killed him from the inside out.
All quotes from one session, minimum context provided. Mostly OOC
Rogue: (When Clown bandits show up) I thought we were on a quest to do paperwork! DM (me): This is on the way to do paperwork. Rogue: OH NO! Juggalo Paperwork!
Wayfinder (Rogue): Wayfinder is about to find out, that most things bleed when you stab them.
Paladin: He’s gonna be like “forgot to add a plus one” on like every roll DM: (damage roll) …and a plus one to that!
Rogue: Knowing the DM, they’ll probably throw a dragon at us any minute. ADHD Monk: I’ll just charm them with my massive Charisma. DM (Ominously): I’ll hold you to that.
ADHD Monk: (To a Great Wyrm surrounded by half Dragon Guards) You need anything else? Drugs, money, hookers? (ooc) Should I roll to seduce them? Great Wyrm: I have lots of consorts, where do you think my Guards come from? Rogue (Not a Half Dragon): Are you my mommy? Great Wyrm: (deadpan) Unlikely.
Rogue: Hang on… Why does this huge ass dragon need us to go find the people who wrecked his lab? DM: Well, it would be a bit conspicuous for a dragon this size to be walking around the middle of the city. Rogue: Most dragons get shape change. DM: Hmm… Hold up a sec, let me check… Nope, turns out Red dragons don’t get that. Rogue: Wait… Then… How the hell did he get inside this building? Paladin: (Bane Impression) He was born into it, molded by it.