My friends and I were playing a Curse of Strahd one-shot, and this was my first time playing D&D; I knew plenty about the game beforehand though, so I knew what I was doing. I was playing a half-elf sorcerer built to be a perfect intel-gatherer, with proficiencies in deception and persuasion, among other things. Other than me, in the party, we had a stone warforged juggernaut cleric, a half-vistani werewolf paladin, a human fighter, an autumn eladrin elf rogue, and a wood elf fighter, and at this point our party was level 5; not very far into the session, considering how fast we were progressing.
We were about to rest at the inn and decided to get a drink at the bar while we relayed information to each other that we had separately gathered that day. The half-vistani werewolf paladin had the Sunsword, but the eladrin rogue wanted it, saying, “It’s shiny, and if it’s shiny, I want it.” The werewolf paladin laughed and said he could easily take her down if she tried to take it. She disagreed, and the rest of the party began the classic chant: “Fight. Fight. Fight. Fight.” The cleric used thaumaturgy to make the chant louder, and suddenly, we had drawn in an audience and were told to continue the fight outside. The wood elf fighter decided she should start collecting bets for the fight. Suddenly I had an idea.
Since it was night and we were now outside, I used prestidigitation to make small fireworks over the fight and draw in a larger crowd. I told the DM I’d like to persuade members of the audience to place bets, the bigger, the better. Because the fighter was helping me collect bets, I was able to roll with advantage. 23. Thanks to the now-large crowd and my persuasive efforts, the bets were in: 505 gold, 810 silver, and 1089 copper on the big, half-vistani paladin, and 200 gold, 17 silver, and 4 copper on the little elven rogue, making a total of 705 gold, 827 silver, and 1093 copper. The other fighter, the human, helped us collect bets for a couple minutes too, but gave the bets to the wood elf fighter so he could go inside to gather more intel from the barkeep. The paladin asked the DM if they knew how much was in the betting pool, likely so he could tease the rogue about his bets being so much higher, but the DM ruled that being in the fight when the bets were being gathered, they wouldn’t know how much was made until afterwards. I quietly shared my plan with the elven fighter as the match went down, and with a nod from her, we were ready to go. I went out of sight and used Alter Self to turn myself into a little girl with blonde pigtails; completely different from my half-elf male with short black hair to reduce any suspicion. The DM and everyone else, having been so invested in the fight, had no idea what we were doing or why I had decided to waste a level two spell slot like that, but didn’t care enough to question it. All the better for me.
I came back to the ring and got all of the bets from the elf. We had our story straight: a little girl saw us collecting bets and decided to help collect more for just a gold piece or two. The fight finished with the paladin reigning victorious, and it was my time to shine. “Let me handle the talking. I’m pretty good at that.” As the paladin and rogue approached for their cut of the bets, the fighter directed them to me. In the voice of a cheery little girl I said, “Hi, my name’s Elaine! I have your cuts of the bets! Sorry we couldn’t get more. I was helping this nice lady get more money for you guys, but these townspeople are poooooor… So here’s the 10 gold for the lady that lost, and 12 for you mister, since you won!” The players instantly knew I was up to something, having heard the earlier total of the bets given by the DM, and tried to insight check me, with me countering with a deception check. I beat them 19 to 17. After all, the two characters had no way of knowing how much was collected while they were fighting, and I was proficient in deception. The player with the human fighter wanted to stop me, so having “just left the inn” he shouted “Wait a minute! I helped collect some of the bets earlier! I know more money than that was in the betting pool!” Too late. By then, I had run off into an alleyway, coins jingling in my pockets.
My wood elf accomplice “chased after me” and out of sight to “get the money back,” and as soon as we were far enough away, we split the remaining money 50/50. I went to exchange the silver and copper for gold at a toy shop (very appropriate for a little girl, right?), and the wood elf fighter went somewhere else (to prevent suspicion) to exchange her money. After exchanging, the profits were a little over 400 gold in total for each of us. Once I finished, I left the store and changed back to my half-elven self, and with that, the little girl had “stolen all of the money and got away” and my great con was finished. The paladin had told me earlier that day that I seemed shady. He had no idea how right he was.