Her Big Brother, His Big Problem

by Rabuiods

Chapter 2: Free Hitching

“It’s nice to finally meet you, Princess Luna.”

Luna looked away from the window toward the earth pony that just addressed her.

“Thank you Mr. …”

“My name is Laughing Stock.” He shook Luna outstretched hoof. She went back to staring at the window. Laughing Stock had so many questions for the Princess of the Night, but he didn’t want to disturb her.

“So Mr. Laughing Stock, why are thou attending this retreat with the Royal Family?” Luna asked, still looking out her window.

“Well, I came with Twilight Sparkle” Laughing Stock explained.

“Oh, thou is the stallion who is courting Ms. Sparkle!” Luna looked away from the window. “We have heard many things about thee!”

“I hope they were all good things” Laughing Stock chuckled

Princess Luna looked very puzzled. “But of course! Why would our sister tell us bad things about thou?”

“I’m sorry princess” Laughing Stock apologized. “It was a joke. I’m a comedian you see.”

Luna still looked relatively puzzled, “What is a comedian?”

Laughing Stock was surprised at the princess’ question. “Well, a comedian is a type of entertainer who makes ponies laugh. Some sing funny songs or use props to tell funny stories, but most comedians tell jokes.” Laughing Stock told Luna more about the comedy world. She seemed to be rather interested. She asked Laughing Stock for a favor after he finished his explanation.

“We have never heard standup comedy before, would thou care to demonstrate?”

“You want me to tell you some jokes?” Laughing Stock had difficulties understanding Luna.

Luna nodded, the comedian cleared his throat and broke into an impromptu stand up performance.

“As you know, I am currently dating Twilight. I am so lucky to have a mare like her; she absolutely flawless! I’m just glad she has found a stallion like me, a stallion who is absolutely flawed!

Princess Luna was shocked to say the least.

“So that’s all thou does? Thou makes fun of thy self?”

“Yeah, pretty much.” Laughing Stock could see that Luna wasn’t sure why a pony would make fun of themselves in front of other ponies. “I have no problem with it. I learned a long time ago that I am not a perfect creature and I am fine with that. I may lack in some areas, but I make up for it in others. Nopony is perfect.

Laughing Stock turned to his left. He watched Twilight talk with Celestia and her brother for a moment.

“Well, almost nopony is perfect.” He sighed as turned back to Princess Luna. “What did you think of your first standup comedy performance?”

“Your princess rather enjoyed it” Luna said with a smile. “Would thou mind making a joke about us now?”

“Are you sure Princess? I don’t pull punches, just ask your sister.” Laughing Stock would have no problem making a joke about Luna.

Luna nodded. She eagerly waited to see what the comedian could do.

“Princess Luna, the whole time I have been here I have been wondering one thing. What is that on your head?” Laughing Stock pointed to the black object that sat behind her horn.

Luna lifted the object off her head so she could show it to Laughing Stock. “Tis our crown, we always thought that was clear.”

“What Celestia is wearing is a crown; what you are wearing looks like a mountain range has sprouted from your head.”

Luna burst out laughing as she placed her crown back on.

“Thou is quite humorous, we can tell thee will be a good companion to have.” Luna went back to staring out her window. She was quiet for the rest of the trip, which was fine with Laughing Stock. He slept the rest of the way while Twilight continued to catch up with her family.


“Laughing Stock, we’re here!”

The comedian opened his eyes, expecting to see a lavish, multi-story building. Instead, he saw your everyday, run of the mill cabin.

As the ponies exited the carriage, Celestia pulled Laughing Stock aside.

“So what do you think of our cabin?”

“It looks so…plain” Laughing Stock admitted. “One would think the royal pony sisters would have something fancier.”

“Every once in a while, it’s nice to just come out here and rough it. Luna and I have ponies do everything for us so we don’t have to lift a hoof, but sometimes I enjoy cooking or doing other household tasks.”

“I’ll make you a deal princess” Laughing Stock said, entering the simple cabin with the ruler of Equestria by his side. “Next time come to Ponyville, you can do all my chores.”

“You’re simply too much fun!” Celestia smiled making her way up the stairs. “Make sure Shining Armor sees that.”

Celestia’s advice echoed in Laughing Stock’s head as he helped Twilight unpack their things. Twilight could sense her boyfriend was troubled. She wanted to help her boyfriend get over what was bothering him so he could start enjoying their vacation.

“Bit for your thoughts?” Twilight took a seat on the nearby bed, patting the empty spot next to her. Laughing Stock took the hint and sat beside his mare.

“You know I love you, right?”

“I hope so” Twilight said with a smirk. “If you don’t, you owe me a year’s worth of rent.”

Laughing Stock elicited a somber chuckle. Normally Laughing Stock would’ve found this hilarious, but the comedian wasn’t in the mood. He leaned in and gave the beautiful unicorn a tight hug.

“I’m being serious. You know I love you, right?”

“Of course I know you love me, why do you ask?” Twilight began nuzzling her stallions’ neck, reinforcing her words.

Before Laughing Stock could answer, there was a knock on the door. Cadance stood in the threshold, looking a little embarrassed.

“Hopefully I am not interrupting anything.”

“Nope, you’re fine” Laughing Stock said, still holding Twilight. “What’s on your mind Cadance?”

“Celestia, Shining Armor and I were on our way into town, so we could pick up a few things for dinner. Would you lovebirds like to join us?”

Twilight immediately accepted the invitation. Laughing Stock declined.

“I want you to go spend time with your family; you don’t see them very often.” Laughing Stock watched Twilight leave, her face glowing with delight at the thought of spending an afternoon with some of the ponies she adored most.

A few minutes later, the earth pony decided to take a look around the rest of the house. Upon entering the living room, he saw a very bored Princess Luna entertaining herself with the record player.

“Princess…what are you doing?”

“This device is rather peculiar.” The princess moved her face closer to the record player so she could get a better look. “How does one use such a complex object?”

Laughing Stock wanted to get far away from this topic, so he suggested doing something outside.

“Outside? Why would we go outside?”

Laughing Stock asked the princess what she planned on doing inside an empty cabin all day. Luna’s gaze slowly moved from the comedian back to the record player. Clearly she had not finished unlocking the secrets of this unknown object.

Laughing Stock opened a small chest. After rooting around for a few minutes, he found a circular disc titled “Coltmanes Greatest Hits” and placed it on the device. After a moment, the disk began to spin while music poured out of the machine.

“This is called a record player” Laughing Stock explained. “Ponies use this to listen to music. The black round things are called records, this is where the music comes from.”

Luna was amazed. “Thou is saying that this beautiful sound is coming from this device?”

“Yes. Now that you know how it works can we go outside?” Out of the corner of his eye, Laughing Stock saw a toboggan propped up against a wall. “Why don’t we go sledding? There is a small hill right outside.”


“You mean you have never been sledding?” Laughing Stock couldn’t believe what he was hearing. “Where is the rock you have been living under?”

“It is back on the moon, where we spent the past one thousand years in isolation.”

For a few awkward seconds, the ponies just sat there with Coltmane playing softly. Laughing Stock completely forgot Luna was once Nightmare Moon.

“We rather stay inside and listen to this lovely composition” Luna said, sitting down in front of the record player.

Laughing Stock had one last idea. If he pulled it off, Luna would be outside in no time.

“Luna come here for a minute.” Laughing Stock walked to the record player and pointed to the spinning disk. “See the label in the middle there?”

Luna nodded as Laughing Stock continued his explanation. “Notice its moving in a circle. The edge of the record is moving in a circle too.”

“Why is thou revealing this to us?” Luna didn’t understand what Laughing Stock was trying to show her.

“The two circles are moving at two different speeds, Luna. See, the outer point has to spin twice as fast in order to keep up with the inner point. So basically, even thought they are moving at two different speeds, they make the same amount of circles per minute! Isn't that cool!”

Luna was dumbstruck. “So…what you are saying is that the outer circle speed have been doubled?”


“All we do is sit on this thing here and slide down the hill” Laughing Stock explained. “It couldn’t be simpler.”
Luna was nervous at first, but she agreed to try this new activity.

“Alright Laughing Stock, you have been a good companion so far. We trust you.”

With the toboggan in tow, the two ponies made their way to the top of the hill. Laughing Stock let Luna sit in front of the sled, so she could get the full experience.

“Alright, here we go!” Laughing Stock pushed off and the toboggan sped downhill. From her cries of laughter, the stallion could tell she was having a great time.

Once their ride came to an end, Luna asked if they could go again. Laughing Stock groaned at the thought of walking all the way uphill, only to end up in the same spot. He wished there was a way to get back up to the top of the hill with no effort on his part. Looking at Luna, he had an idea.

“You know what is more fun than sledding, Luna?”

The princess shook her head.

“A game you play while you are sledding called Uphill.”

“What is this game thou speaks of?”

Laughing Stock started grinning, “The pony that can drag the sled uphill the most times wins. I should warn you though, I am pretty good. Do you still want to play?”

Luna was eager to beat this stallion at his own game. She grabbed the rope and started climbing toward the top of the hill.

Before she could make any progress, Laughing Stock stopped her.

“You get bonus points if you let somepony ride on the sled while you carry it up.”


“Laughing Stock, please do not take offense by our inquiry, but are we almost done with this activity?”

Princess Luna and Laughing Stock spent the last hour sledding, both ponies were exhausted.

“Yeah, we are pretty much done, unless you want to find another hill to go down.” Laughing Stock really wanted to go inside and dry his fur, but he started feeling guilty about the whole “Uphill” thing.

“Let us ask that colt over yonder if he knows the locations of other fun places to sled.”

From what Princess Luna just said, Laughing Stock assumed that she wanted to ask for directions. They made their way to a small colt with red fur and a messy blonde mane; he was towing a sled that appeared to be very badly damaged.

“Are you hurt?” From the state of the sled, Laughing Stock guessed the colt had crashed.

“No, we’re fine” the colt said. “We wouldn’t have crashed if my co-pilot told me that tree was in the way!”

Princess Luna and Laughing Stock scanned the area for anypony else, but they didn’t see a single soul.

“Where is your companion at this moment?” Luna wanted to make sure there wasn’t another injured pony somewhere.

“He’s on the back of the sled” the colt replied.

Both Laughing Stock and Princess Luna looked behind the colt at the mangled sled. There was nopony there; in fact the only thing that was on the sled was a stuffed animal.

“Are you saying the stuffed animal is your companion?” Laughing Stock still didn’t understand what was going on, but he didn’t care. He wanted to go home.

“Yes and a lousy one at that!” The colt turned to face the toy. To everyponies surprise, he began screaming at it.

“Hey, don’t mean to interrupt your…discussion.” Laughing Stock had no idea what was going on, but he didn’t want to stick around and find out. “You know if there are any long sled trails around here?”

The colt told the two of a sled run that lasted a few minutes; he gave the ponies directions and went on his way.

“That colt is a rather peculiar specimen” remarked Luna.

“I bet he drives his parent’s nuts.” Laughing Stock stated as they made their way to the top of the massive hill.

Minutes later, Luna and Laughing Stock found themselves at the peak of an extremely large hill. Laughing Stock carefully placed the toboggan in the snow and climbed on. As Luna took her place behind the stallion, he asked if she was sure this is what she wanted.

“We are very…very high up, and there are lots of obstacles to maneuver through. Are you sure you want to do this?”

Luna wrapped her front hooves around Laughing Stock, as a precaution for the ride they were about to take. The stallion began to rock back and forth until the toboggan began to slowly move forward. With one last thrust, the two ponies began their downhill journey.

After a few seconds of traveling downward at breakneck speed, Laughing Stock broke the silence with a question.

“So Luna, Twilight told me about the whole Nightmare Moon thing when we first met. If you don’t mind me asking, why did it happen?”

Luna gripped the stallion a little tighter as he barely avoided a pricker bush.

“Well, it’s rather difficult for us to discuss…”Luna said while the ponies ducked under a low hanging branch.

“I understand completely. Forget that I even asked,I just wanted to get to know you a little better.” The stallion felt stupid as he continued to pilot the toboggan.

“I suppose it all happened because I was very jealous of my sister’s popularity.” Luna’s statement caught Laughing Stock off guard, nearly causing him to steered themselves into a creek. “It didn’t seem right that everypony in all of Equestria preferred the brightness and warmth of the sun over our dark and mysterious moon. We became very carried away with our lust for the spotlight.”

“Well if it makes you feel any better Luna, eternal darkness sounds awesome” Laughing Stock took his eyes off the terrain in front of him to look at the sullen princess. “I would have more opportunities to sleep.”

Laughing Stock expected to make Luna smile, she rolled her eyes instead.

“That is exactly what we were referring too! Everypony just slept all night! They never took time to partake in all the glory that is our night! ”

“No offense princess, but you are a little off on your view on the common pony.”

The princess was taken aback by the stallion’s comments.

“Do you have evidence that proves our assumption was misguided?”

Before Laughing Stock gave his reasons, he focused all his attention on the mountainside in front of the toboggan. “Well, ponies love sleeping and sleeping usually happens at night. Therefore, ponies like the night.”

Princess Luna wasn’t amused.

“Surely that isn’t the best argument thee could come up with.”

“It’s not; I have plenty more…and don’t call me Shirley.” Once again, Laughing Stock excepted the princess to find his play on words humorous. He decided to give Luna the second part of his argument.

“Well, my best friend Vinyl Scratch is a very popular DJ. She absolutely loves staying out late and performing shows for her thousands of fans. Even though she wears sunglasses, she has always told me night time is the best time. I have no idea what she means by that, but I know more fans show up to night shows than any other time of day.”

Luna still wasn’t convinced. “We are still certain that ponies across Equestria prefer our sister’s sun over our moon…”

Laughing Stock had one last chance to make Luna see that somepony out there appreciated her work.

“I look forward to the sun setting every night, do you know why?”

Luna remained quiet.

“Every night, I fall asleep with Twilight in my arms.” Laughing Stock could feel Luna’s grip on his midsection tighten. Whether it was because she like what he said, or because he narrowly avoided a collision with a pile of rocks, he wasn’t sure. “When I finally told Twilight I loved her, it was underneath your moon and stars. Every night when I fall asleep with that beautiful mare, I think back to that amazing moment in my life.”

After hearing Laughing Stock pour his heart out to her, Luna had one question.

“Thou made a confession of undying love underneath our moon?”

“Yes...why?” Laughing Stock had no idea where this was going.

“We find it very humorous that a pony with your creativity would do something so…uncreative.”

“So wait…I try and help you feel better, and your response is to tell me the way I told Twilight I love her was cliché?” Laughing Stock started chuckling, shortly thereafter Luna joined him.

“We are sorry if our comments offended thee. We really think thou is a great companion to have, Twilight is a very lucky mare.” Laughing Stock turned to Luna, hoping to thank her for the kind words. Before he could get his words out, she asked another question.

“What about the plunge?”

“Celestia told you I was planning on asking Twilight to marry me?” Laughing Stock didn’t know why Princess Celestia told her sister, but he trusted Luna to not say a word. “I really want to, but Shining Armor is making things very hard.

Luna turned the stallion’s head around and pointed in front of them. “We mean the plunge that is eminent.”

Before Laughing Stock could react, the toboggan sailed over the cliff in front of them. The comedian’s first instinct was to grab Luna, his second was to shut his eyes and start screaming like a little school filly.



Laughing Stock continued to hold on to the princess of the night after a few minutes. He wanted to know when the impact would take his life, but out of principle he kept his eyes shut.

“I love you too, sweetie. Why are you cuddling with Princess Luna?”

Hearing Twilight’s voice, the stallion opened his eyes. He was sitting on the sled in front of the cabin. The rest of the group came back from town, watching the show that was happening before their eyes.

He immediately let go of Luna. “I thought I was going to die! I can explain…well actually I can’t. I should be a pancake right now.”

“We were out on this wooden contraption here” Luna was pointing at the sled she had shared with Laughing Stock. “Then we lost control and careened off a small overhang no more than ten feet off the ground. Laughing Stock was afraid to finish our activity, so I transported us home.”

“So how was town? Buy lots of fun stuff?” Laughing Stock desperately changed the topic.

“We bought food, so we could have a homemade dinner” Celestia announced. “Then I thought we could all play a game together. Sound like fun?”

Laughing Stock agreed that it sounded like a fun night. “Is there anything I can do to help with dinner?”

“No the four of us have it under control” Cadance raised a hoof to the east of the cabin. “Shining Armor went that way to collect firewood; maybe you could go help him.”

Laughing Stock began trotting in the direction Cadance referenced. He found the unicorn gathering kindling. He noticed Shining Armor was having a hard time carrying the supplies, this gave Laughing Stock an idea. He returned a few minutes later with the toboggan.

“Hey Shining Armor, need a hoof?”

“No” Shining Armor grunted. “I got in under control.”

As soon as he said those words, he proceeded to drop very piece of wood he was holding.

“Well, I brought this sled with me. I figure we can put the wood on it and pull it back to camp.”

Shining Armor was stunned to say the least.

This nimrod actually had a good idea…

As the two stallions loaded the wood on the toboggan, Shining Armor broke the silence.

“I’m sorry if I upset you, I really am. I want to make sure Twilight is with somepony that can provide her with everything she has ever wanted.”

“What a coincidence!” Laughing Stock finished loading the rest of the firewood, so he was able make eye contact with Shining Armor. “I have done everything to your sister!”

Laughing Stock immediately realized his mistake. He started cursing quietly to himself.

FOR you idiot! You have done everything FOR his sister…

“What did you just say?!”

“I meant to say FOR your sister, not TO her.” Laughing Stock tried back peddling in order to save his flank. “I would never tell you about our bedroom activities!”

“Why would you even bring that up?” Shining Armor couldn’t believe he was having this conversation with his sister’s boyfriend.

He is either really ballsy or a complete moron.

To say Laughing Stock was a nervous wreck would be a massive understatement.

“I don’t know!” The stallion started panicking; he couldn’t keep his mouth closed. “I would never intentionally tell you Twilight likes putting her mane in a bun, putting on a pair of glasses and scolds me for not turning my books in on time while she...”

Laughing Stock threw his front hooves over his mouth to prevent himself from talking, he said way too much already. Shining Armor placed his head on a nearby tree.

“I think you better leave” the unicorn suggested. The earth pony took his advice, but not before putting his hoof in his mouth once again.

“I don’t know if it makes you feel better, but your sister is a very dedicated librarian. She always makes sure I learn a lesson if my books are late.”


Laughing Stock sprinted back to the cabin. Avoiding the mares in the kitchen, he made his way to his room and climbed into bed. Princess Cadance came up a few minutes later; she wanted to know how it went.

“It started off good, the ending didn’t go so hot” Laughing Stock explained while hiding under the covers.

“It couldn’t have been that bad.” Princess Cadance tried cheering up the distraught stallion.

Laughing Stock told Cadance everything he said, including the sexy librarian spiel.

“Laughing Stock, you dog! I never knew Twilight had it in her.” Cadance smiled at her friend, trying to make him feel better.

The stallion poked his head out from under the covers.

“Hearth’s Warming Day is six days away, how am I going to get his approval in time?”

“I’m not sure, but Celestia and I will do our best to help out” Cadance said reassuringly.

“Why do you care so much Cadance?” This question was at the back of Laughing Stock’s mind since the two ponies met at the fountain the day before.

“Because if it wasn’t for Twilight, I wouldn’t be here with my wonderful husband” Cadance explained. “The way I see it, helping you with your relationship with Shining Armor is my way of repaying the debt I owe her.”

While leaving the room, Cadance told Laughing dinner would be ready in a few minutes while making her way out the door. Before heading down, Laughing Stock took a moment to think before heading down. Tomorrow he would have to start being serious about trying to get Shining Armor to like him.


After dinner, the group made their way into the living room and gathered around the coffee table.

“Are we ready to play a game?” Celestia asked, making her way to the hall closet.

“I don’t know if I want to play with you guys” Laughing Stock said with a grin. “You guys have a distinct advantage.”

“Whatever do you mean?” Princess Celestia wasn’t sure of the advantage Laughing Stock was talking about.

“Well, I’m the only pony here who can’t use magic” Laughing Stock pointed out. “Three alicorns, two unicorns and an earthpony…wait hold on…there’s a joke here somewhere.”

The room erupted with laughter as Celestia laid the game on the table. Laughing Stock looked to see what game Celestia brought down.

“Monopoly?!” Laughing Stock was excited, Monopoly was his favorite game.

“Should we select out tokens now?” Cadance was eyeing the small silver figurines. There were many to choose from.

“Great idea Cadance” Celestia said with a nod. She turned to the earthpony sitting across from her, “You pick first Laughing Stock.”

Laughing Stock looked at the different pieces. The horseshoe, pot of bits, carriage, small dog, and riverboat all looked really neat, but the small statuette of a particular white alicorn caught his attention.

“Dibs on Princess Celestia!” Laughing Stock pulled the token toward him, but Shining Armor put his hoof over the earth ponies’ hoof.

“Celestia is always the Celestia token; you’ll have to pick another one.” Shining Armor insisted, but Princess Celestia moved the royal guard's hoof. “It’s perfectly fine, Shining Armor. I am quite fond of this little doggie here.”

After unanimously voting Twilight Sparkle to be the banker, the group began rolling to see who would go first. Cadance rolled highest; Laughing Stock patiently waited for Cadance to roll. Laughing Stock watched the pink alicorn move 4 spaces, which would make her land on the tax square.

“Alright Cadance, two hundred bits please!” Twilight placed her hoof in front of Cadance, and the princess reluctantly paid. Twilight placed the money back in the tray with the extra bits that had not yet been distributed.

“Whoa, Whoa” Laughing Stock shouted. “That money goes in the center.”

“What do you mean?” Twilight summoned the slip of paper with the rules on it. “I don’t see anything in the rules about the putting tax money in the center.”

“Yeah, it goes there” Laughing Stock insisted. He went on to explain if a pony landed on free hitching, they would win all the money in the center.

“The rules say nothing about it, they say that the free hitching square is just a space nopony can buy” Twilight Sparkle said, the rules still in front of her lovely face.

“Right, I’m sure they say we can buy property on the first go around as well” a sarcastic Laughing Stock jested.

The room fell silent.

“We CAN buy property on the first go around?”

“Even we knew thou could do such a thing” Princess Luna teased.

Taking his turn, Laughing Stock rolled the dice. The five he received brought him to the first railroad square called the Friendship Express. Making sure to capitalize on his mistake from earlier, he bought it right away.

The game moved at a steady pace. Everypony had circled the board at least once, and majority of the property had been purchased. Laughing Stock was on a roll; he owned all the railways, the Lightning and Raincloud factories, and his personal favorite: Pony Place and Boardtrot! Once he was able to develop hotels on the two blue squares, he knew his friends would be in a world of hurt.

“Oh, we have rolled two doubles in a row!” Princess Luna picked up the dice and rolled again.

“HAHA double four!” Luna shouted with delight, but the delight soon faded as Celestia picked up Luna’s riverboat and placed it in jail.

“WHY HAVE WE BEEN IMPRISONED?” Luna shouted in the traditional Canterlot voice. “WHAT INJUSTICE HAVE WE COMMITED?”

“If you roll doubles three times, you get sent to jail.” Celestia explained, Luna was still beside herself with worry.


Twilight rolled her eyes and placed her head on one of her hooves.

A few minutes later, Shining Armor landed on an Opportunity card. He read the card to himself, and then looked up at the board. He sighed heavily as he moved his token to the square the card mentioned, which was Laughing Stock’s Boardtrot.

“Alright, Shining Armor” Laughing Stock was trying his hardest not to smile as he did the math. “With three houses, it will cost you…eleven thousand, one hundred bits!”

Shining Armor grumbled as he gave Laughing Stock the money.

Laughing Stock looked at his fellow players to see how long before he claimed victory. Everypony was almost out of money, with the exception of Princess Celestia. Her fortune was growing steadily as everypony fell victim to her side of the board. With the exception of the railroads and Raincloud factory, she owned every piece of property, with a hotel on each of them.

“I had a question. The way I have always played, we made our own Opportunity cards” Laughing Stock explained. “Anyway we could make our own?”

“Interesting…” Cadance thought that this idea could spice up a game that had turned rather dull. “What kind of homemade cards?”

“Well we always had a card that allowed somepony to rob a bank.”


“Luna, you have one turn left in jail” Celestia reasoned. “Until then, could you be quiet?”

Luna continued to pout as the game went on. The first pony to run out of bits was Twilight. While her properties were auctioned off, she moved along side her boyfriend. She gave him a kiss and told him he had to win to avenge her loss.

“Wipe the floor with them, Stocky” Twilight cheered!

“Yes, Twiley” Laughing Stock responded as play continued.

With the acquisition of Twilight’s Marediterranean and Bridle Avenue’s, Laughing Stock had the six spaces that surrounded Go. He knew his victory was eminent.

Cadance rolled a seven. When she approached the seventh square, she hung her head. It was Canterlot Gardens, one of Celestia’s spaces.

“Cadance sweetie, do you have twelve hundred bits?” Celestia knew her niece did not have the funds necessary to keep playing.

Candance levitated her piece into the box and took a seat next to her husband.

“I AM FINALLY FREE!” Princess Luna eagerly rolled the dice, desperate to escape the confines of the evil square. Her roll caused her to land on the first Opportunity square. Picking her card, Luna went ballistic and threw her card on the board.


Laughing Stock picked up the discarded card. He wanted to see what made Luna so mad.

Go directly to jail, do not collect two hundred bits for passing go.

“My turn, right?” Shining Armor asked as he grabbed the dice. He threw the dice, which landed him a double four. As he moved his token eight spaces, he landed on Pony Express railroad, which was owned by Laughing Stock.

“Two hundred bits please” Laughing Stock said with an outstretched hoof.

Shining Armor forcefully placed the money in the outstretched hoof. He rolled again, this time he received a double five. The unicorn moved his piece ten places and cleared his throat in anger. He had landed on Equestria Railroad.

Before Laughing Stock could open his mouth, two hundred bits flew at him.

For the third time in a row, Shining Armor threw the dice. They seemed to roll in slow motion as he bit his bottom lip. Would he join Luna in jail, or end up paying Laughing Stock more money.

When the dice finally stopped, it landed on eleven. Shining Armor let out an audible sigh as he moved his piece to the Opportunity square next to Shortcake Railroad and Pony Place. As he picked up his card, he grew very silent. The game board was suddenly surrounded by a rose light and was launched into the air, as Shining Armor stomped away. A worried Cadance followed her angry husband.

Celestia picked up the card that Shining Armor had received and read the message. She began to quietly snicker as she passed it around. By the time Laughing Stock got a hold of it, he just shook his head, with a grin on his face. The card read:

Catch a ride on the Friendship Express.

“Shining Armor knew that Laughing Stock owned all the railroads. He was down to his last two hundred bits” Celestia explained.

“Didn’t he know that he had to pass go in order to reach the Friendship Express? He would have had an additional two hundred bits!” Laughing Stock, Twilight and Celestia stopped giggling for a moment to look at Princess Luna, who was on the ground, collecting all the bits she could grab.



“What a day!” Laughing Stock climbed into bed, with Twilight right behind him. She took her usual place beside her boyfriend.

“Tell me about it” Twilight responded, lying down beside her stallion.

“Well, we woke up early, took a long ride in a carriage, I went sledding with Luna an-“

Twilight kissed Laughing Stock good night before asking him a very important question.

“Do you ever shut up?” Twilight teased as she placed her head between Laughing Stock's neck and shoulder.

"Twilight, does your brother hate me after the way the game ended?"

"No, you should be fine" Twilight yawned. "He has always been a poor sport.”

He smiled as he held his girlfriend and went to sleep. Once again, he couldn’t help but think about how lucky he was to have somepony like Twilight.

This mare is definitely worth fighting for, was his last thought before falling into a peaceful slumber.


A/N: I do not own the rights to Monopoly or My Little Pony. Thank you Hasbro for not suing me.