Game Night Fight

by The card holder

Rating: everyone
Tags: Anon, My Little Pony: Friendship is Magic, Comedy, Slice of Life, Human, Twilight Sparkle, Main 6
Length: 9872

Anon describes a board game from home, and Twilight arranges a game night to recreate it. This proves to be a greater threat to their friendship than anything they have faced.

Anon has been living comfortably in Ponyville for a while now, but the novelty has been wearing off, and now he misses many of the entertainment options he had back home. He brings this up to Twilight, and together they arrange for a game night with her friends to try and make Anon feel more at home.

Unfortunately, Anon forgot just how badly human board games can strain or break even the toughest of friendships.

This story was a commission by IHateNumbers

Published 2023-02-27 04:50:01 UTC
Last updated 2023-06-30 10:59:23 UTC

Roll the Dice

As far as Anon knew, he was the only human living in Equestria, and he was bored.

Sure, life in Ponyville was comfortable. He had been here for over a year now, and he was already settled in with a long-term job and friends around town, but there was always that itch for something to do on those days when he had no work and no one was immediately available to hang out.

There were books, of course, but he could only handle so much reading of pony literature. In most regards, ponies were far more innocent-minded than humans, and while that allowed for a perfectly safe and happy lifestyle, it came with the side effect of crippling the quality of their writing, at least as far as Anon was concerned. The darkest thing he ever found in a pony story was a single murder mystery, and even that was a cop-out because the "mystery" ended with there being no murder at all!

Of course, Anon's next attempt at entertaining himself was to simply nap the days away, but this had the drawback of not only throwing his sleep schedule out of whack, but also drawing concerned attention from Princess Luna within his dreams. It took longer than he wanted to convince her that everything was fine, but it still made him not want to sleep too much during the day.

Thankfully, there was one final way Anon found to keep himself occupied: board games.

It was pure happenstance, he went over to Twilight's place to see if she wanted to hang out when he caught Spike and Starlight playing chess. Sure, it was called something else (just "castle" which was, curiously, not a horse pun like so many other names around Equestria), and the pieces all had different names, but it was still recognizably chess, with the same number of pieces performing the exact same movements. Anon was never a fan of it back home, but he still knew the basics, and was very easily able to talk Twilight into playing it with him semi-regularly. All of his other friends either didn't know how to play properly or had zero interest.

This is where we find Anon now: engaged in a battle of wits against the princess of friendship, brows furrowed as he considered all of his move options. His blue side of the field was slowly encroached upon by Twilight's red forces, but he made sure that his king (or princess, as the ponies referred to it) was defended. Despite Twilight's lead, Anon did have a few pieces in position for a long range attack, he just had to find the right way to get past her with minimal casualties to himself.

Across the table, Twilight was equally focused. It was as if she was trying to predict which move Anon would make, and thus what her best response would be.

The silence in her reading room was deafening.

Eventually, Anon reached down and slowly moved a bishop (sentry) into position. "Check."

Twilight sucked in a sharp breath, and Anon grinned. She had more experience on him in this game, but Anon had the advantage of playing unpredictably. He never learned any of the proper maneuvers one could perform in chess, which made him a complete wildcard capable of anything, as far as Twilight knew.

Suddenly, Twilight's eyes lit up, followed shortly by her horn. As soon as her queen (princess's aide) was coated in her magic, Anon muttered a curse. He spotted the opening he left, but far too late.

She placed the aide just short of taking out his sentry, but that was never her goal. She now had a direct line of attack on his princess piece. Not only that, but even if Anon retaliated with the adjacent sentry, Twilight had her own perfectly in line to make the same attack.

Twilight looked up and smiled. "Checkmate, Anon."

Anon groaned and flopped back in his seat. "Jeez, you're good at this."

Twilight laughed sheepishly as her magic cleared the board. "Well, I had a lot of free time as a filly, and my dad said castle keeps the mind sharp. I guess a lot of that practice stuck."

Anon stretched out his arms. "Well, I played it a bit in highschool, never too often and never anywhere close to professional. I'm just glad I remembered what I did."

"It still fascinates me that the same game exists in both our worlds," Twilight said.

"I chalk it up to the same reason a lot of Equestrian city names are eerily close to human city names," Anon said as he shrugged. "Weird cosmic coincidence."

Twilight let out a thoughtful "Hmm," and looked over at a nearby whiteboard. She levitated a marker to add a tally to her win count. She was now up to twenty-seven wins, compared to Anon's pitiful two.

Anon grimaced when he looked over and was reminded of his poor performance against the pony. "Maybe we should find some other game to play. I don't think I have quite the mind for chess. Or castle, or whatever."

"Nonsense, you're still one of the better players I've seen!" Twilight tried to reassure him. "I've never seen anypony else manage to counter a Hoofman's Opening with a Trotter's Cut!"

"Twilight, I have no idea what the hell those are."

The princess sighed. "Well, I guess we could find another board game to play."

"The only problem is I don't know any other pony boardgames," Anon said. "Whatever you pick, you'd have a huge advantage over me."

Twilight put a hoof to her chin. "Hmm, fair point. Maybe we could find a game neither of us have played before?"

Anon quirked an eyebrow. "Would you know where to find such a game?"

Twilight hesitated, then deflated. "No..."

Anon rolled his eyes and stood up to stretch his legs. "Well, I'm gonna run to the bathroom real quick."

Twilight folded up the castle board with her magic, and replaced it and the pieces in their box. "Alright, I'll see if I can come up with something while you're there."

Anon nodded and left the room. Twilight put the castle box back in a nearby closet and looked through every other board game she could find. There were a number of children's games that she skipped over. She had no idea why she still had them, honestly, but she also couldn't bring herself to get rid of them. Even still, she skipped over them in her search. She doubted Anon would have much interest in playing a game meant for small colts and fillies.

Thankfully, there were a few more adult-oriented games in the stacks, as well, and Twilight retrieved any she thought might be to Anon's tastes. Over the year or so he had been in Ponyville, she managed to learn a fair amount of what he did and didn't like, and so she tried to choose accordingly.

Just as she finished her selection, Anon returned. "Oh, nice, you already got a few."

Twilight nodded and read through the assembled games. "I have Crystal Land, Pirate Ship, Book Trivia-"

Anon snorted with laughter. "Of course you have a board game about books."

Twilight rolled her eyes. "Anything jumping out at you?"

Anon dropped back into his chair and shook his head. "Not so far."

Twilight shuffled through the stack of boxes and pulled out a new one. "How about this one? It's called Mayor For a Day."

Anon sat up slightly. "Sounds interesting. How's it play?"

Twilight flipped the box over with her magic and read the blurb on the back. "'Two to eight players work together to run the perfect pony town. Manage properties, build homes, and avoid scandals to become the most prosperous village in all the lands.'"

"Hmm." Anon tapped a finger on his knee. "Something about all that sounds familiar..."

Twilight turned to him, eyebrow raised. "Really? Is this another game you had a version of back home?"

Anon racked his brain. It definitely reminded him of a human board game, but for some reason the name was escaping him. "I think so, except..." Even without the name, he could still remember the differences from what Twilight read out. "...I think it was less about running a town together and more about business. Buying property, staying out of jail, charging other players if they land on your stuff, that kind of thing."

Twilight flipped the box back over. "Huh. So it was more of a competitive game than a cooperative one?"

"Something like that, yeah."

She tapped a hoof to her chin in thought. "That could prove to be an interesting experience." She suddenly jumped up onto all fours, an excited gleam in her eye. "Hey, why don't we get everypony together later this week and we could play your version of this game?"

Anon matched her smile. "Oh, a game night? I can't even remember the last time I had something like that back home."

"Then it sounds like a fun way to spend an afternoon!" Twilight levitated every other game back to her closet, but kept out the box for Mayor for a Day. "Do you think it would be possible for you to write down all the rules you can remember from your version?"

Anon scratched his head. "I mean, I could try. My memory's a bit fuzzy on every possible detail, but I'll see what I can come up with." He pointed at the game box and added, "Could I take that home with me? If I have the actual board on hand, I might have a better job remembering."

Twilight nodded and levitated the box to him. "Sure thing, Anon."

He accepted the box from her magical grasp, but paused when he noticed how Twilight was practically bouncing in place. "You seem pretty excited about this, Twiggle."

"Oh, hush," she shot back. "I'm the Princess of Friendship, of course I'm excited that a relatively new friend from an entire other dimension wants to share a game from his own world with his other friends!"

Anon laughed and tucked the game box under his arm. "You ponies and your friendships, I swear."

"I figured you'd be used to it by now."

He shrugged and started walking to the door. "Guess you're right. Anyway, I'll be heading off now. Make sure to tell me when game night's happening, alright?"

"Will do, Anon!" Twilight waved goodbye. "See you then!"

Anon left Twilight's castle and spent the entire walk home trying to remember everything he could about the game he was remembering from back home. He clearly remembered the broad strokes, and a lot of the more basic deviations from the pony version he held, but the more he thought on it, the more rules remained stubbornly lost in his memories.

By the time he made it home, he was already opening the box to take a look at the contents. Eight player pieces, which were all a random facet of pony society, like a carriage, a train, or even just a horseshoe. The board was a square, divided into multiple color-coded property spaces on each side. There were even two six-sided dice in the box, which helped to jog some of Anon's memories for the game.

The function of the other spaces weren't immediately obvious to the human, so he decided that he should probably learn how exactly this game was supposed to work before he started to bend and twist those rules to better fit the obscure memory floating in his subconscious.

Sure enough, it was an entirely cooperative experience, just as the box claimed. There was a large bundle of small colored bills in the box, and the rules stated that all this money was pooled between all of the players, for them to work together and spend on the properties around the board, while minimizing losses from random events brought about by a deck of "crisis cards" that described all manner of situations that could make the group gain or lose money, from the mundane to the comical. At least, Anon viewed something like a "rabbit outbreak" as comical. For all he knew, that was a serious problem that ponies had to face at one time with tragic results.

He pulled out a notebook from one of his desk drawers and began taking notes of what rules would be changed, and how. The first and biggest one was obvious: players would compete instead of work together, each with their own stash of money. Rather than properties being something to upkeep and repair as the game goes on, they'd be bought and developed, to punish any other players that landed on them after the fact.

The corners of the board were the most perplexing to Anon. The start space was obvious, and even the original rules in the book mentioned the players gaining more money every time someone did a loop of the board and passed it. In the opposite corner, there was a space that only contained a bed and the words "Day off." The manual explained that this was a free space, meant to be celebrated since it meant nothing went wrong when a player lands on it. However, Anon swore that space did something completely different in the game he was trying to remember...

Eventually, Anon had an epiphany, and rapidly wrote down what he remembered: that space was meant to be a "jackpot" space, where money collected from random events was pooled, thus whoever landed on that corner would receive a massive payday.

Unfortunately, Anon had unknowingly made a critical error, and had incorrectly remembered a rule that didn't actually exist in the official ruleset for the game he was imagining. This would not be the last such error he would make, and all of them would ultimately prove to be disastrous.

For now, though, Anon was oblivious, and was on a rapid pace, writing down every rule he remembered along with how other spaces on the board would function. Surprisingly, the board already had something similar to the jail spaces he was familiar with, in this version described as a random villain capturing one of the players, taking them across the board, and forcing them to either get out on their own or be helped out by someone else. Of course, Anon made sure to write down how players sent to the cage were on their own to get out, be it through rolling doubles or paying a fee.

"Rolling doubles..." Anon muttered to himself just after he wrote the phrase down. Another memory hit him like a bolt of lightning, and he went back to the manual to look for something.

However, nothing was mentioned of rolling doubles in the pony version of the game, but that didn't stop Anon from remembering the extra turns they gave in his game. He hastily scribbled them in on his ever-growing rules list.

After what felt like no time at all, Anon took a break to lean back and stretch. He looked out the window and was surprised to see that it was now dark outside. A glance at the clock told him that he had been working for a few hours now.

He decided that this was as good a time as any to call it a night and get some sleep. After all, he had a few more days, at least, until game night with Twilight and her friends.

Those next few days were busy for both Anon and Twilight. While the human continued to dedicate his spare time to the drafting and perfecting of the rules for the game, the princess traveled around Ponyville to talk to her friends and see if they wanted to partake of game night. She could've simply sent out letters, but she found that propositioning her friends face to face was not only much more polite, it also had a much better chance of securing their attendance once the time came.

She had already decided that they'd all get together next Saturday, since that was when there were the fewest schedule conflicts, but it wasn't perfect. Trixie would be out of town for the weekend on some errands, Starlight would be accompanying her in order to ensure she didn't get in any serious trouble, and Spike apparently had accidentally volunteered to help the Cutie Mark Crusaders with something and was too polite and/or concerned to back out and leave them entirely on their own.

The first pony she visited about the matter was Pinkie, who was not only ecstatic at the thought of having a board game party with her friends, she even offered to bring some sweets for them all to enjoy during the occasion. Twilight graciously accepted the catering; it was why she started with Pinkie, after all. Even if that mare could manifest a sugary banquet for them out of thin air with very little notice, Twilight still wanted to be polite and give her a bit of time to prepare.

After her was Rarity. She wasn't the biggest fan of board games, owing to her constant losing streak against Sweetie Belle whenever they tried to play something together, but she was still intrigued by the idea of Anon coming up with a new game for them all to play.

Twilight managed to meet with both Rainbow Dash and Fluttershy at the same time, since the former flew down to see what Twilight was up to at the latter's house. Twilight wasn't even halfway through her explanation before Dash cut her off and said she was in. Apparently she was still upset about the time Anon completely decimated her in a game of castle (Twilight was surprised that she knew how to play it, only for Dash to clarify that she didn't, but still took the challenge). Fluttershy, meanwhile, hesitated before saying that she'd be there. Even if she wasn't the competitive sort like Dash, she'd still like to be there to at least hang out with her friends, if nothing else.

The next place Twilight visited was Sweet Apple Acres. Applejack was in the middle of working, but like usual, that didn't stop her from having a conversation with a visiting friend. She was happy to join in on the festivities, especially when she learned that Dash and Anon were also going to be there.

And last but certainly not least, Twilight paid a visit to Anon's place to see how he was coming along, and to pass on the date of the get together. When she knocked on his door in the afternoon, it didn't take long for him to answer.

"Oh, hey, Twi," he said. He tried to act casual, but Twilight could see the beginnings of bags under his eyes.

"Hey yourself, Anon," she greeted back. "You okay? You look... tired."

Anon shrugged. "A bit. Been staying up a bit later than normal trying to nail down every detail on this board game." He stepped aside and waved her in. "I think I'm just about done, actually, so great timing."

Twilight entered his home and shut the door behind her. Anon wasted no time and presented a rather large bunch of papers, each page filled with handwritten and amended notes and rules. It was a lot to take in all at once.

"I... see," she eventually said. "You've been busy on this, huh?"

"Yeah, it took a lot of sitting and trying to remember, but I think I got all of the rules down now," he said. He took a drink from a glass of water that sat on his desk, then asked, "So, when's everyone getting together?"

"This Saturday at noon. It's when most of us have free time, and..." She looked again at the mountain of rules Anon had written. She focused on one of the first passages, which detailed how the game worked in a competitive sense. "...That's probably for the best, because I have a feeling this will take a while with seven players."

"Oh yeah, that reminds me," Anon pulled out another piece of paper and handed it over. "Here's a list of things you'll need to get for the game to work, too. This box didn't have enough."

This was only one piece of paper, thankfully, with only a few written lines, but it was still enough to make Twilight feel the slightest bit of concern. "Bigger house pieces than the game came with? Blank cards? Five times the normal amount of play money?!"

"I mean, we both know this Mayor for a Day game isn't one-to-one with the one I'm remembering," Anon said. "For one, there's just not nearly enough money in a single box to distribute between so many players." He pointed to the bundle of rules paperwork that Twilight still held in her magical grasp. "The other two will make more sense once you read through that. The cards are very important, though, because otherwise there's no way to denote who owns what properties."

She slipped the shopping list on top of the packet. "I- I see..." An awkward silence filled the room, so she pointed at the game box that still sat on Anon's desk, wide open. "What about what was included? Were you able to find a use for everything?"

"Oh, yeah, totally." Anon pulled out the game board and unfolded it to show her. "I hope you don't mind, but I went ahead and made some adjustments to the board, to better fit what I remembered."

Twilight looked at his handiwork. There was now a lot of marker graffiti on the spaces, either to overwrite text that was originally printed there or to assign one of eight different colors to properties around the board. "You... doodled on it?"

"Hey, they're more than just doodles!" Anon pointed to a set of colored spaces. "This is really important to play the game right!"

"Uh huh." Twilight was wondering if it was such a good idea to let Anon have this much free reign over the project, but she didn't say anything to stop him.

Anon took the lack of objection to continue his explanation. "See, players can buy the properties up as they circle the board, but they can't actually develop them and build houses and stuff unless they have all of a certain color. That way, players who get a monopoly would earn even more-" He suddenly cut himself off and slapped a hand to his forehead. "Monopoly! That was the name of the game!"

For some reason, both of them felt an eerie chill go down their spine as soon as he remembered the name.

Twilight did her best to shake off the feeling and said, "So... it's a very business-oriented game, I guess?"

"Something like that," Anon answered. "Everyone competes to get the most money and bankrupt the others."

"Wouldn't that make the game a bit... antagonistic?" Twilight asked, more than a little worried.

Anon leaned against his desk and shrugged. "I mean, I guess, but that's part of the fun, building up rivalries and even alliances as the game goes on."

Twilight tilted her head. "Alliances?"

"Oh, yeah, it's in the rules you haven't read yet, but players can try and make deals with each other at any time. Try and get something from another player in exchange for something else, that kind of thing."

Part of Twilight's mind still felt a bit apprehensive about this whole idea, but she squashed it down. After all, this would be played among close friends, and even if the game itself proves to be a bust, they can use the day to hang out and do other things, no problem. "Alright, then. I'll get started on this shopping list, get everything we need for Saturday."

Anon smiled and put everything back in the game box and added it to her magical levitation cloud. "Thanks a bunch, Twilight." He hesitated, then added, "It feels surreal, sharing something as mundane as Monopoly from back home, but... it's not bad."

Twilight shared his smile. "I'm very glad to hear that, Anon." She turned to leave, everything still held in her magic. "See you Saturday!"

"See you then!"

Twilight walked back out into the open air. She still had a few lingering doubts about this 'Monopoly' game Anon was so dedicated to recreating, but she pushed them aside. Whatever problems they ran into, they'd be able to resolve them with no drama at all.

After all, they were all great friends, and a simple board game wouldn't be enough to jeopardize that...

...right?

Pay the Price

The next few days passed very quickly for Anon. Now that he didn't have to stress about remembering the rules for Monopoly, he spent most of his days after work catching up on the sleep he missed. Because of this, when Saturday finally rolled around, he was more than ready to head over to Twilight's place to partake in game night.

By now, whatever doubts he had about playing the game had vanished. He had a good feeling that today was going to be a fun time for everyone.

He was blind to the fate he had sealed for himself and his friends.

Anon was confused to see that he was the first one to arrive at the castle, besides Twilight of course. She already had a table set up with seven chairs around it, along with the box to the Mayor For a Day game sitting front and center on said table. The lid was a bit lopsided, as if someone had stuffed more contents into the box than it was originally designed to hold.

Twilight still held the packet of rules in her magic, but looked up from them to give Anon a tired smile as he arrived. "Hey, Anon, you're a bit early."

He checked his watch. "Really? You said Saturday at noon."

Twilight gave a light-hearted eye roll. "Just because I set a time doesn't mean anypony meets it. I've been friends with these ponies long enough to know that, no matter how much they mean well, they'll always be at least a few minutes late to things."

"I mean, usually I am too," Anon admitted, "but I just got up kinda early today and I figured I'd make sure I was here on time."

Twilight smirked. "I don't think I've ever seen you this excited for something, Anon."

He shrugged and took a seat at the table. "I'm curious how this will play out." He glanced around the rest of the room. While there was a second table set up a small distance away, he couldn't hide his disappointment at the fact that it was still empty. "Say, weren't there gonna be sweets and stuff?"

"Pinkie said she'll bring it all once she's here," Twilight said. "Normally I'd ask anypony else to bring it in advance, but you know how she can be."

"Oh yeah, speaking of that," Anon said, "I've always wondered, how exactly does Pinkie do all that stuff she does?"

Twilight shook her head, smiling. "Don't think too hard about it, Anon. I already made that mistake."

"Wait, what do you mean-"

Anon was cut off by a knock at the door. Twilight called, "Come in!" and the door opened to reveal Rainbow Dash, who quickly swooped into an empty seat.

"Dang, Anon beat me here?" she asked. "I must be slowing down a bit."

"I just had nothing else going on today," Anon said. "Besides, aren't you normally fashionably late?"

Dash leaned back and shrugged. "Eh, I'm in the same boat as you. Got bored, figured I'd go ahead and come over a bit early."

"You can just admit you were excited for the game," Twilight said.

"I mean, I do get to whoop you all at something new," Dash bragged, "so I guess that'll be cool."

Anon rolled his eyes. "You don't even know what the game is yet."

"So? I'm a fast learner."

While they laughed off Dash's bravado, Pinkie bounced into the room with a wagon in tow, stacked taller than Anon with sweets. He had to do a double take because the stack was taller than the door, but he didn't see how the hell she managed to get it through.

"Hiya Anon, Twilight, Dashie!" Pinkie said, bouncing from one friend to another in time with her greetings. She pulled the wagon next to the table and Twilight began levitating the sweets into place.

"Hey, Pinkie," Dash greeted. "You look excited for this whole thing, too."

"But that's how she always is," Anon pointed out.

"Both right!" Pinkie said as she bounced into the seat next to Dash. "I've never played a human board game before! This oughta be fun!"

Rarity and Fluttershy arrived next, together. "Glad to see everypony had the same idea about arriving early," Rarity commented.

"Well, besides AJ," Dash said. "Funny, she's usually the punctuated one."

"Punctual," Twilight corrected without thinking.

"Yeah, that too."

"I think she was talking to Apple Bloom last I saw," Fluttershy said.

"Oh yeah, her sister's doing something with her friends and Spike," Anon said. After a moment, he added, "We sure they'll be okay?"

"Eh, I wouldn't worry about it," Dash said. "Scoots is with them, and she's the toughest little filly I know."

"I also trust Sweetie Belle to keep them in line," Rarity said.

"Same with Spike," Twilight added. "Even if anything happens, I know he'd come here to tell me first thing."

As they talked, Applejack finally arrived, already looking a bit sour. "Sorry I'm late, gals, just had to lay down the law with Apple Bloom 'bout her little 'adventure' today."

"What exactly were they doing, anyway?" Anon asked.

Applejack shook her head. "She wouldn't say. Just told me she'd be with her friends and Spike."

Dash waved a dismissive hoof in the air. "I wouldn't worry too much, they're a smart bunch."

Anon chuckled. "Smarter than you?"

"Hey, maybe!"

The seven of them shared a laugh as snacks were grabbed and the rest of the seats were taken. Twilight was the last to join them, with the over-stuffed board game box trailing behind in her magic. She set it in the middle of the table and began to set it up as she explained.

"So, I admit that this game is a bit complicated, Anon was very thorough about a lot of details."

"You're welcome!"

"Right." Twilight continued. "Anyway, the game is still based on Mayor For a Day if you remember how to play that, but it's now competitive in nature. If you run out of money, you go..." She glanced back at the rules packet to search for the right word. "...'bankrupt', and you're eliminated from the game. Last one playing wins."

Stacks of bills and slips of paper listing properties were stacked in front of Anon as Twilight kept speaking. "This game requires one player to operate the bank, and because Anon is most familiar with this game, he will be in charge of it."

"Hey, couldn't he just cheat and give himself extra money?" Dash asked.

"Oh come on, I wouldn't cheat," Anon said. "Besides, even if I wanted to, I doubt I could with all of you watching."

"He's never cheated at anything before," Applejack defended him.

"Thank you, AJ."

By now, Twilight finished setting up the board and took her own seat. The player pieces were just different colors of tiny pony models, so everyone picked a color close to their own without complaint. Anon was left with the green piece.

"So, who goes first?" Rarity asked.

The table filled with silence. Twilight brought the rule book over and flipped through it. After a few moments, she looked at Anon. "You didn't put down how turn order is decided."

Anon blinked. "Oh, uh, whoops." After a second of thinking, he snapped his fingers. "I think it went by age. Oldest player goes first, then clockwise from them."

Everyone looked between each other.

"I think that's me," Fluttershy said. "Unless you're older, Anon?"

Anon shrugged. "I'm twenty-three."

Fluttershy nodded her head. "You're older, then."

"Wait, wouldn't humans age different from ponies, or something?" Dash asked.

"I'd rather not get into that kinda stuff," Applejack said. "We can just let Anon go first."

"Well, alright then." He picked up the pair of dice and made the first roll of the night.

A two and a three.

Anon moved the five spaces, landing on the railroad. He gladly bought the property without fuss. The ponies watched his turn carefully.

Applejack was next, and she carefully picked up both dice in her hooves. "Alright, I think I get it." She rolled, and got a pair of twos.

After moving her piece, she bent down to read the text that Anon had drawn on over the normal space. "Pay two hundred? To who?"

"To the middle," Anon said. "It turns into a reward for whoever lands on this space," he pointed to the empty corner space, "first."

Applejack exhaled sharply as she put the money in the middle. "Already down and nothing to show for it. Off to a good start."

She went to pass the dice to Dash next to her, but Anon stopped her. "Hey, you rolled doubles, you can go again."

"Oh, really? Nice." Applejack rolled again, getting a five and a six. She moved the eleven spaces and landed on another railroad. "So, I pay you for this?" she asked Anon.

"Well, you pay the bank," he said. "You want it?"

Applejack looked at her lessened funds, then nodded. "Sure."

She gave him the money and he gave her the card. Dash picked up the dice as they did this and made a quick roll. Double sixes.

"Aww yeah!" She zipped her piece across the board, then tilted her head when she landed. "Electric company?"

"You want it?" Anon asked.

Dash tapped a hoof to her chin, then shook her head. "Nah. I'll just go again."

She rolled again, and got snake eyes. She moved the two spaces without comment, this time agreeing to buy the property. After the exchange, she pointed to the dice. "So, do I just keep going?"

Anon nodded. "Yes, but-"

"Sweet!" Dash cut him off by rolling again, and got a pair of threes. She began to move again but Anon stopped her by putting a finger on the board.

"You rolled doubles three times in a row, that means you go to jail," he said, pointing to the corner of the board she just passed.

Dash looked at him. "What? That sounds made up."

"He's right, Dash," Twilight said, holding up a page of the rules. "Three doubles in a row means directly to jail."

"A bit too fast, I reckon," Applejack said, smirking.

Dash groaned and put her piece in jail. "Whatever. I'll get out."

"Ooh! Ooh! Me next!" Pinkie hopped in her seat as she quickly picked up the dice and rolled, only to land on the same spot as Applejack, but without the doubles. "Woohoo!"

"Uh, Pinkie, you lost money," Applejack said.

Pinkie nodded. "Oh, I know, but this is still fun!"

"As long as you're enjoying yourself," Rarity said as she levitated the dice into the air then dropped them for her roll. A four and a six, so she landed on the same jail space as Dash.

She blinked. "So... am I in jail, too?"

"Nah, you're just visiting," Anon said, pointing to the edge of the space. "Nothing happens if you land there."

"Ah, I see."

Fluttershy rolled next without a word. She landed on another unclaimed property, but when Anon prompted her about buying it, she just softly said, "No thanks."

"And then it's me," Twilight said. She rolled the same way as Rarity and landed on the railroad Anon bought. He looked at the card, told her the price he'd have to pay, and she gave it over without comment.

"Alright, now I get how this game works," Dash said. "We just have to buy up stuff and get ponies to land on them, right?"

"Pretty much," Anon agreed. "So, how we all feeling about it after a full round?"

"I'll see this through," Applejack said. "This is plenty interesting, I gotta say."

"Likewise," Rarity said. "I'm sure this will be good fun."

Once again, Anon felt a chill down his spine, but he ignored it and picked up the dice. "Then let's keep going."

The following hour passed by before anyone knew it. One by one, the ponies and Anon made their rounds around the board, sometimes buying up properties they landed on, sometimes passing them up for various reasons.

Dash managed to get out of jail after two turns by rolling another set of doubles on her second attempt. However, she landed on the single property Fluttershy had purchased when she did so, which led to plenty of grumbling from Dash and chuckles from everyone else.

For now, the atmosphere was competitive, but still friendly. More importantly, as the ponies came to grips with how exactly the game worked, they asked Anon less and less questions about how things worked. There were a number of Chance and Community Chest cards drawn, but they were all obvious enough to figure out without needing much extra explanation from Anon. Rarity even managed to snag a Get Out of Jail Free card, which she was more than happy to stash away for later.

As money slowly traded from pony to person to pony, a clear tide was beginning to form. Despite her best efforts, Applejack's funds were approaching zero. She had already been told about selling her properties back to the bank to stay out of bankruptcy, but she was too stubborn to do so until she had no choice.

Luckily for her, she didn't need to consider that option. After a small roll of five spaces, she landed on the Free Parking space, and was able to collect the now-sizable pot in the middle of the board.

"It won't last," Dash attempted to taunt her.

"We'll see," Applejack replied, still sorting her new bills together.

After a few more turns, Twilight ended up being the first to obtain a Monopoly, now owning all of the yellow properties on the board. For the first time in a while, she consulted Anon's rulebook.

"What does it mean if she owns all of a color?" Rarity asked.

Anon lifted up the plastic holding the bank's cash, revealing a small bag full of plastic homes. "Now she can start building houses on them."

"Not until my next turn, though," Twilight said, putting the rulebook back to its corner on the table.

"So, what do houses do?" Dash asked.

Applejack looked down at the property cards she owned, and went wide-eyed. "Take a look for yourself."

Dash followed her gaze, despite having her own properties to inspect, and her jaw dropped. "The price can go up that much?!"

Anon grinned. "Yep. You're not scared, are you?"

Dash huffed and puffed up her chest. "It just means I'll have to hurry to catch up and do it first!"

Pinkie giggled. "This is fun!"

The others shared her sentiment as Anon took his next turn. As luck would have it, he would be the next one to complete a color set, though his weren't as valuable, being the light blue properties on the first side of the board. Still, it was progress, and he was happy to take the properties.

While the ponies went through their round of turns, he looked closer at the board, and inspected what everyone else owned. All four railroads were bought now, split evenly between him, Applejack, Twilight, and Fluttershy. Dash managed to snag both utility spaces, despite passing Electric Company up on her first turn, and there were only a handful of colored properties left unowned.

He had his eyes on two in particular, though. The dark blue spaces at the end of the board, the spaces he knew were infamous for bankrupting players in a single go. Pinkie held one, and Dash held the other. So far, nobody had thought to bring up trading with each other, and he wasn't sure if he wanted to be the first to try it or not. After all, once that particular genie was out of the bottle, the game would inevitably become far more complicated.

Anon snapped his attention back to the rolls just in time to see Rarity land on the Go to Jail space. She levitated her card from earlier and asked, "Can't I use this and ignore that?"

"Nope," Anon said. "You still go to jail, you can just use it to get out without rolling or paying."

"Drat." Rarity moved her piece to the opposite corner, and Fluttershy took her turn. She landed on a Chance space, and timidly drew a card and read out the contents.

"'You come second place in a beauty contest.'" She shrunk slightly at that sentence and quickly read the rest silently, before quietly saying, "I get fifty dollars."

Anon quirked an eyebrow as he handed over the money from the bank. "What, don't like that card?"

She looked away, blushing slightly. "Don't worry about it."

Rarity stifled a chuckle beneath her hoof, but when Anon looked to her for an answer, she pretended to be busy inspecting her hoof.

He shrugged it off. It probably wasn't anything important.

Now that it was Twilight's turn again, she inspected her Monopoly and rubbed a hoof on her chin in thought. After some glances between the property cards and her funds, she nodded to herself. "Two houses, please."

Anon obliged from the bank's stash of plastic, and she levitated them in place onto two yellow spaces.

Dash shifted uncomfortably in her chair, since she was positioned not far behind those new houses. Pinkie was, as well, but she simply swayed gently in her seat, still smiling as wide as ever.

With her developments made, Twilight rolled the dice and ended up landing on Go. Anon gave her the standard $400 for doing so (standard as far as he remembered, at least), and then he made his own house purchase.

Thankfully, houses for his properties were much cheaper than Twilight's, so he was able to easily put one house on each of his three light blues. After that, he rolled, and landed on the jail's visiting space, next to Rarity.

Unfortunately for Applejack, she rolled high enough to become the first victim to Anon's homes. After he gave her the passing Go bonus from the bank, he then immediately read off the new price of his property, which led to her giving most of it back directly to him. She grumbled as she did so, but she wasn't discouraged. She still had a fair amount of money in her corner, especially after her earlier jackpot, she would live.

Dash took a deep breath, rolled the dice, and prayed.

Her prayers were answered, as she managed to narrowly avoid Twilight's houses and instead land on Waterworks, something Dash herself owned. She gave a big sigh of relief, and both Anon and Applejack chuckled.

"What's wrong, you sweatin'?" Applejack asked.

"Pssh, no," Dash lied. "I knew I'd miss them."

"My turn!" Pinkie announced as she scooped up her dice and made her roll. She wasn't as lucky as Dash, and landed directly onto one of Twilight's built up properties. "Yay!"

Dash glanced at her. "Uh, Pinks, that's bad."

"Oh, right." Pinkie's smile shrunk, but it didn't fully vanish, as she looked to Twilight for the cost.

Twilight hesitantly read it off, then Pinkie started counting up that amount. However, she ran out of bills before she could match it.

Everypony paused, then looked to Anon for guidance. "So... what now?" Twilight asked, even though he could tell by her expression that she had an idea what came next.

Anon shrugged. "If Pinkie can't pay the rent, she's bankrupt and out of the game," he said. He then pointed at her property cards and added, "you can sell those back to the bank to get the money, though."

Pinkie considered it for a moment. "Hmm..." After a few seconds, she snapped back up in her seat. "Nah, I'm good!"

Dash was confused next to her. "Wait, you're just gonna take the loss?"

"Yep!" Pinkie nodded happily. "Can't win 'em all. That was fun, though!"

Twilight sheepishly levitated what money Pinkie had into her own, then looked at the properties she still had. "What about them?"

Anon looked at her. "Didn't I write that down in the rules?"

Twilight brought the rulebook to her face and quickly shuffled through it. "Nope, you never mentioned what happened to a player's properties after they go bankrupt."

Anon smacked his forehead in frustration at himself. Of course he'd manage to forget something so important. "Uh, well... If I remember right..." He wracked his brain, trying to find any memory about what to do in this situation, until he finally arrived at some kind of answer. "I think... they go back to the bank? So people can buy them again."

The ponies all looked at each other, then collectively shrugged. "Sounds good to me," Dash said.

Fluttershy nodded.

Twilight levitated the cards over to Anon, who stacked them back with the other unpurchased spaces.

Once that was all dealt with, Rarity cashed in her Jail card to leave, and then took her turn.

More time passed as they made more trips around the board. Now free from the game, Pinkie bounced (often literally) between the snack table and the game table, just to watch how the rest played out.

Surprisingly, Fluttershy was the next one to obtain a Monopoly, nabbing the oranges just behind the Free Parking space. After her turn, Twilight rounded out her own properties with one more house, then rolled and bypassed Anon's houses, only to land on Electric instead. Her high roll meant she had to pay quite a bit to Dash, but the spoils from bankrupting Pinkie meant she wasn't perturbed by the cost.

Anon rolled next and managed to land on the railroad belonging to Applejack. He handed over the cash without comment, and the game continued.

He glanced at the remaining dark blue property, now up for grabs with Pinkie out of the game. Dash was in a position to grab it if she wanted, but she was just as likely to avoid it, as well. It was hard to land on a specific space if you wanted it, after all.

More turns around the board, and Fluttershy joined Anon and Twilight in the house game, though only with a single one for now. It paid off immediately, because Twilight was unlucky enough to land on it on her next turn.

Money continued to be passed around, the prices increasing to drastic levels when the Monopolies were involved. Twilight and Anon slowly added more houses to their properties, Fluttershy slowly following behind them.

Dash barely missed the vacant dark blue property, instead having to pay tax to the middle of the board, which meant Anon was the next one to have an opportunity to nab it. As luck would have it, he barely managed to land on the spot, and bought it up without hesitation. Now he just needed a way to get the other from Dash.

Rarity was the next to get a Monopoly, laying claim to the reds next to Twilight's yellows, and despite her vulnerable financial state she seemed pleased by this. Normally, she would've made some kind of taunt towards the others, but by now the game was beginning to become serious. The only things said between the players were prices as they landed on each other's spaces, or reading out cards and their effects.

Twilight landed on a Community Chest space, and was dealt a critical blow by what awaited her. "Assessed for street repairs... Forty per house?!"

Twilight still only had the single Monopoly, but she had stacked it with ten whole houses between them. This meant she had to pay a very steep price.

Anon shook his head. "That's a rough time to get that one."

Twilight glanced over her paper bills, and even Anon could tell that she didn't have enough. She looked back at her houses and asked, "I can sell them to pay for it, right?"

Anon nodded. "Yeah, but I'm pretty sure you'd still have to pay as if you still had them all."

Twilight sighed. "Fair enough." She returned four of the houses to the bank, took the money she spent on them, and then put most of it right back into the middle of the board. The Free Parking jackpot was once again quite stuffed.

Anon rolled, and managed to get double sixes. He passed Go, got his two-hundred, and landed on his own Monopoly before rolling again. As soon as the dice landed and he saw where he was going, he pumped his fist in silent victory before setting his piece in the corner and collecting the jackpot for himself.

"Man, when am I gonna win that?" Dash asked. "I'm falling behind fast here!"

"Sounds like a you problem, sugarcube," Applejack taunted as she took her turn. Her smugness instantly dissolved when she landed on Fluttershy's orange property, stacked with two houses.

Fluttershy seemed genuinely sad when she told her the price.

Applejack counted up her bills, but came up just short. She sighed and gave her railroad back to the bank in order to get the rest, but Fluttershy tried to stop her. "Oh, Applejack, you don't have to pay if-"

"No, I do," Applejack cut her off. "Them's the rules, right? I land on your stuff, I pay for it."

Fluttershy accepted the money after a moment, though she still didn't seem thrilled about it.

Dash picked up the dice to roll, but paused. Instead, she looked across the board and asked, "Didn't you say we could trade in this game?"

Anon felt a nervous pit grow in his stomach. "If both players agree, yes. Why?"

She pointed at one of his property cards, then to one of her own. "Give me that green, I'll give you this blue. Deal?"

Anon wanted to scream in celebration, but he maintained his poker face. Even if the trade would give her a Monopoly, it was exactly what he wanted. "Deal."

They swapped cards, even under Twilight's concerned gaze. "You sure about that, Dash? Those blue spaces get pretty expensive..."

Dash waved off her concern. "It's only two spaces. I have three greens. Mathematically, I'll win. Or something." After a moment, she also asked, "I can still buy houses this turn, right?"

Both Anon and Twilight nodded, so she immediately put out two homes on her greens. After that, she took her roll and landed directly onto Anon's three house light-blue.

She smacked a hoof to her face and grumbled into it. Anon gave her the price, and while she was able to afford it, it left her with barely any money left.

The game continued into the evening. Despite the high stakes and the amount of money being traded across the board, nobody could be truly eliminated. Even if they managed to land on an expensive property and didn't have the money available, they would simply sell some houses or properties to make the difference up, only to buy them back later as they earned more money either from the other players or from the occasional jackpot.

Even still, Applejack constantly found herself on the back hoof, never truly being able to catch up once everyone else had Monopolies and houses. After many stubborn turns spent clinging to her spot at the table, she was finally done in by an unlucky landing on Dash's green spaces. Even if she sold every property she had, she'd come up just short of the price.

She sighed heavily, gave her money to Dash, then stood up from the table, joints cracking as she did. "Welp, that sure was somethin'."

"Almost had us, AJ," Dash said, though her tone leaned close to mocking.

"Shut up, Dash."

Applejack's blunt retort went unnoticed by the table. She went to join Pinkie at the snack table, who was cartoonishly napping on a couch next to it.

More turns passed, and Anon finally claimed his first victim to the dark blue titans. Unfortunately, it was Fluttershy, so he felt way too bad about it to enjoy the sensation. She had to sell almost all of her houses to meet the gargantuan bill, and it wasn't long before she was in the same place as Applejack moments ago.

In the meantime, Rarity and Twilight ended up securing secondary Monopolies of their own from the properties Applejack left behind. Dash landed on her own Electric Company again, and when Fluttershy's turn came around and she managed to land on Go with a pair of snake eyes, she asked, "Can we build houses at the end of our turn?"

The question surprised Anon, so it took him a bit to respond. "Uh, yeah. Why, you want to?"

She nodded and gave over the money, and Anon handed her the appropriate amount. At first, he wasn't sure what she was doing, since this left her with little money, but then he noticed that Dash was in the perfect place to land on them next turn.

After Fluttershy rolled again and ended up on a now-available brown space that she declined, and Twilight and Anon both made inconsequential low rolls, Dash rolled and ended up falling right into Fluttershy's trap. She groaned when she heard the price, and she had to sell all of her houses just to make the payment.

Rarity's turn sent her directly to jail, and Fluttershy narrowly avoided Anon's properties and landed on Community Chance, which sent her right back around to Go with a free four hundred dollars.

Twilight rolled next, and landed on Dash's now-homeless green properties. Dash threw her hooves up and groaned in wordless frustration, but still accepted the meager amount of cash.

Anon landed on Twilight's housing development, which put a sizable dent into his money, but he was able to make the payment without selling anything, which still left him in a good position.

Dash rolled next, and ended up landing on Rarity's red set. At first, she didn't do anything, but then Rarity cleared her throat.

"What? You're in jail," Dash said. "I don't have to pay you if you're in jail... right?"

Twilight coughed as she flipped through the rulebook. "Well, actually..."

"Oh come on!"

When she saw that she'd once again have to part with something to make the payment, Dash instead just shoved the money she had towards Rarity and aggressively shoved away from the table. "Whatever, this game sucks anyway."

"Please don't be a sore loser," Fluttershy said, but it went unheard as Dash went to the opposite end of the snack table from Applejack.

After Fluttershy had to pay tax right in front of Go, Twilight rolled and became the second victim to Anon's dark blue four house Monopoly. This massive bill cost her most of her houses, and she grumbled as she gave over the money.

Anon managed to join Rarity in jail, but he considered this a good thing. Jail meant he wasn't moving around the board, and that meant less chance to land on someone's property and lose all his money.

Rarity clearly had the same idea, because she spent her turn rolling to get out rather than paying the minor exit fee. Unfortunately, she got a pair of threes on the first try, and had no choice but to land on Fluttershy's domain. This resulted in much of her own houses being undone, as well, and she glared silently at the board, as if it were to blame for her misfortune.

Now very financially stable, Fluttershy added yet more houses to her domain, and bought up the last purple she needed to obtain another Monopoly. Anon tapped his fingers on his leg; she now had complete control to take from anyone coming out of jail.

Twilight, meanwhile, proved to be the unluckiest person at the table as she rolled a pair of ones, sending her from one dark blue property directly to the next.

"Horseapples," she muttered to herself, and after doing some quick math regarding everything she owned, realized she didn't have nearly enough and forfeited her money to Anon. "Well played."

She left the table and the room, and Anon briefly heard her angrily say, "Spike, what did you do?!" before the door closed.

Anon put all of his focus on the other two players. Rarity was on the ropes, but Fluttershy was quickly gaining momentum as well. Even with the money he earned from Twilight twice in a row, he knew that it could just as easily vanish thanks to them.

History repeated itself as Rarity rolled low enough to land on Fluttershy's orange properties again, and this time it was enough to knock her out. She didn't say anything, just levitated her remaining money over to Fluttershy and left the table and the room, the same way as Twilight.

And then there were two.

Anon studied his opponent. Fluttershy still refused to make eye contact, same as usual, but she wasn't looking in another direction like normal. She was fully focused on the board, and Anon swore he could see some part of her posture shift.

With the both of them flush with cash and a lot of the board now up for grabs again, they rolled back and forth, losing incidental amounts to each other's railroads or undeveloped properties while buying up everything they could.

The room was silent save for the rolling of dice, the moving of plastic, and the occasional brief readings of numbers.

Dear Princess Celestia,

This is a sudden request, but could you please come to Ponyville and try to talk some sense into Anon and Fluttershy? They have been in my castle playing that board game from Anon's world for well over twelve hours now, and there doesn't seem to be any sign of them stopping. I would intervene myself, but to be quite honest I feel like they might try to hurt me if I did.

Once that is done, I will also need your help to dispose of the board game, including having Princess Luna wipe the memory of it from our minds, if that is possible. None of my friends wished to speak to me after last night, and while I respect that the game is an aspect of Anon's culture, I fear that it may have proven to have caused irreparable damage to our friendships.

Signed,
Twilight Sparkle

P.S. If, hypothetically, three fillies and a dragon somehow came into possession of an infant ursa minor, what would be the fastest, safest, and most discrete way to return it home?