It's not gambling if you can't lose

by Charm3d

Rating: teen
Tags: Rainbow Dash, Fancypants, Comedy, Rarity, Random, Wonderbolts, My Little Pony: Friendship is Magic
Length: 3105

Rarity and Rainbow Dash win tons of money by betting on the Wonderbolts' races.

It's no secret that Rainbow Dash knows everything about her idols, the Wonderbolts. But, when a tip from Rainbow puts a nice chunk of change in Rarity's back pocket during her stay in Canterlot, the pair try their hands- or, in this case, hooves- at a rather unconventional means of making a living.

Rated Teen for gambling, mild use of alcohol, and other Vegas-related themes.

Comments welcomed and appreciated, let me know what you think.

Published 2013-10-26 14:00:02 UTC
Last updated 2013-10-26 14:00:02 UTC

1. AND IT'S FLEETFOOT BY A NOSE!!!

"Listen, I have a VIP box reserved at the Wonderbolts Derby this afternoon. Would you be so kind as to join me and a few of my companions there?"

Rarity was shocked. No, she was utterly stunned that Fancy Pants was even talking to her after she had been so rude to him by slamming into him in the middle of the street. Come on, Rarity she scolded herself. Can't you even walk down the street without making a fool of yourself? Fancy Pants was, after all, one of the most iconic faces in all of fashion! Becoming friends with him could mean big things for her boutique in Ponyville; alternatively, he could make her life very difficult if he saw fit to do so. She did not want to give him a bad impression by being rude or even... uncouth. The little fashionista inside her head was screaming at her to get a grip:

WAKE UP, MORON! FANCY PANTS JUST ASKED YOU A QUESTION!

Rarity simply could not function today. Any suave or class she once possessed had escaped her body the moment she ran into Fancy Pants. She could only respond to him with a pathetic whimpering of "m-me?"

Fancy Pants seemed amused. "But of course, my dear!" he replied kindly.

Rarity was dumbfounded. This scene between her and Fancy Pants was playing out incredibly well for her, despite the fact that she had wronged him. She could barely contain her excitement; not only had she met the Fancy Pants, he was offering her an opportunity to socialize with the Canterlot elite! Even if it was for just one afternoon, It was a dream come true!

Play it cool, Rarity she thought to herself. Just say yes. Y-E-S. Three little letters. Two consonants, one vowel. One measly little syllable.

Wait, isn't the letter "Y" a vowel though....?

The importance of the consonant-vowel-letter-thing seemed to swallow all of Rarity's thoughts in an instant. She lost focus, and was only able to give Fancy Pants a very unintelligent, "Well I...uhhh..umm... not sure."

You, my dear, are pitiful.

"We'd love to see you there, um...?" Fancy Pants fished for the young pony's name.

"Rarity."

"Rarity..." Fancy Pants echoed, the name rolling off his tongue as the two ponies parted ways.

It really was all too kind of Twilight to arrange for me to stay here; I'll have to find some way to make it up to her. Rarity reflected as she approached the castle. I could always make her a delightful new gown to wear.

Rarity had planned this trip to purchase rare jewelry for a client in Fillydelphia, but it was Twilight who made it possible for her to stay in the castle. At first, she was only supposed to stay for a day or two, but she decided to stay a few extra days to enjoy the city of Canterlot itself. This was the first time in her life she had ever ventured to the capitol city of Equestria, and she really wanted to get out and play tourist for a few days if she could find the time. Of course, that was all before she bumped into Fancy Pants.

Rarity couldn't believe her luck. Not only had one of the most, if not the most, influential ponies on all fashion matters in Canterlot asked her to join him as his guest, they were to be attending The Wonderbolts Derby. Rarity chuckled to herself; Rainbow Dash will be immensely jealous when I tell her this juicy bit of information she speculated.

The guards to the castle let her through the main gate without hesitation; after all, one does not easily forget someone as eye-catching as Rarity. Especially after a trainee accidentally tried to bar her entry to her suite and was met with a half hour of "HOW DARE YOU" delivered over one hundred different (and incredibly creative) ways. Fortunately, the princess heard Rarity's outburst from across the castle grounds when the young mare's scolding reached the ultrasonic level, and the issue was quickly resolved.

Rarity's suite was in its own private tower, adjacent to Princess Celestia's living quarters. As the doors to her secluded suite at Canterlot Castle opened, Rarity's pet cat, Opalescence, hissed maliciously. Upon realizing that the doors opened for her master and not a vicious hose-bearing intruder, however, she ceased her hissy fit.

"Opal-Wopal!" Rarity exclaimed with glee, "You will never believe who I just bumped into!"

To which the cat replied with a licking of its cat-parts.

"I just bumped into the one and only Fancy Pants, and he invited me to be his guest at the Wonderbolts Derby!"

Disinterested, Opal switched from her cat-parts to the backs of her paws.

Supplies and suitcases littered the floor of the suite. Not being known for packing light, Rarity had brought upwards of twenty bags and purses to hold all of her precious sewing equipment, fabrics, designs, and of course, pet care products for little Opal. While the suite itself was magically maintained to prevent dust, dirt, or insects from gathering, nothing was preventing Rarity's belongings from cluttering the rug in the center of the room. To pass the time until the Wonderbolts Derby, she decided to do a little tidying-up.

Rarity arranged all of the materials required to create Twilight's new birthday present, an incredibly elaborate new dress, in the corner of the room next to her bed. She laid the fabrics over a mantle adjacent to the window, and then she opened the window to let in some light. Next, she assembled her sewing machines and placed them on the table near the fabric. Satisfied with her creativity-corner, she unpacked her clothing. The closet was massive, as one would expect the closet of a castle to be. In fact, it was so massive that the closet was subdivided into smaller closets for each article of clothing!

"I think I'm in love!" Rarity squeaked, sounding oddly like her sister, Sweetie Belle. Never before had she gazed upon such closet space. She adored the thought that each shirt, coat, hat, dress, and shoe would have its own little room to itself. She was absolutely enthralled with the lifestyle of Canterlot royalty.

The starstruck dress-maker spent the next hour showing each individual piece of clothing that she owned its new temporary home. Before she knew it, the time had come to prepare for the Wonderbolts Derby, so she took out an adorable light-green chapeau out of its little home and placed it atop her head.

"Opal, darling, this hat will surely win over Fancy Pants and his friends, don't you agree?" Rarity asked her closest companion.

Opal replied by coughing up a hairball.

After changing hats, Rarity made her way towards Sky-High stadium. The weather outside was absolutely wonderful, and there was not a cloud in sight, probably due to the Wonderbolts clearing the skies as a part of their warm-up before the race. Even though Rarity was not one for sports in general, even she understood the significance of the Wonderbolts Derby. Ponies from all over Equestria flock to Canterlot each year to see the race because it is the first out of three races to determine who will be the fastest flier in all of Equestria. In this highly-competitive environment, even amateur fliers can rise through the ranks of the Wonderbolts Professional Racing Circuit to earn the coveted title. Of course, entry fees into the races are steep, and few pegasi make it to the professional level without losing thousands of bits first. A Wonderbolt has earned the title of best flier in Equestria almost every year.

Thinking on this, Rarity realized that must be why Rainbow Dash applied to the Wonderbolt Academy. Someone like Rainbow Dash could not possibly stand the thought of another pegasus being a better flier than her. Rainbow wanted to learn from the best of the best, and maybe even become a professional someday.

Sky-High stadium was unlike anything Rarity had ever seen. The track itself was traditionally donut shaped, made entirely of clouds, and managed by a small team of highly-trained Canterlot weather ponies. But that wasn't the interesting part.

The track hung over the side of a massive cliff, and the seats were physically attached to the cliff face. The only way to access the stadium was via a slim trail that ran parallel to the cliff face and made Rarity positively queasy when she looked over the side. Fortunately, the weather ponies always kept the area completely wind-free to prevent anyone from getting blown over the cliff, and there were enchanted clouds below the trail to prevent anyone who had a little too much to drink from taking a deadly fall.

The sun peeked over the side of a cliff such that the track itself was bathed in an orange tint, while the seats and VIP boxes attached to the cliff itself were shaded from the sun. The teal flags placed at both ends of the track appeared purple in the sunlight, but the spectators themselves were hidden from the sun. Rarity was glad she wouldn't need the sunglasses she'd left in her suite.

Rarity approached the ticket office at the front of the stadium, and she was greeted with a gruff "ticket please" from the stallion behind the counter.

"Oh, well I don't have a ticket, you see. I was invited here by someone..." Rarity began.

"What'd you say your name was?" the stallion asked unenthusiastically.

"Rarity."

Upon hearing her name, the stallion straightened up and immediately looked apologetic.

"Oh! Of course, Ms. Rarity, I have your ticket right here!" He handed her the red ticket stub which was stamped "VIP" on the back.

Puzzled, Rarity replied "Thank you very much," and proceeded past the ticket office and into the stadium itself.

As she entered the stadium, Rarity noticed parade music being played from a band on a stage separate from the bleachers and VIP boxes. Recognizing the tune, she began to hum quietly to herself as she looked around the inner stadium. As usual, gift shops blocked immediate entry from the seating area, cleverly placed to lure ponies' wallets. Closest to her, however, was a rather large stand labeled "Bets" at the top. She walked over to the stand to investigate, and, just as she suspected, she found ponies betting on the upcoming race.

Now now, Rarity, let's not get too hasty here... she thought to herself.

Recently, the young mare had gotten into a little bit of gambling trouble back in Ponyville. After her friend Apple Jack taught her a card game called "Blackjack" Rarity had gone and thrown half a month's salary down the drain at Sugarcube Corner's semi-annual "Las Pegasus night".

Still, some unstoppable force drew Rarity closer and closer to the counter...

"Put it all on Fleetfoot!" she found herself shouting as she shoved twenty bits at the stallion collecting bets.

Somepony behind her sniggered. "You sure you want to do that, Lady? Rapid Fire is gonna win, no doubt about it!"

Rarity really didn't know that much about racing; but, recalling something Rainbow Dash once told her about Fleetfoot, she decided to stand her ground.

"Well we'll just have to see, now won't we?" she replied curtly.

"Rarity! Jolly good to see you, so glad you could make it!" Fancy Pants exclaimed as he greeted her at the entrance to the VIP box.

Not knowing what to say, she smiled sweetly at him and the pair made their way to the viewing area, striking up a conversation about the race as they climbed the stairs together.

When looking up the word "classy" in the dictionary, there should be a picture of Fancy Pants' VIP Box. From the outside, it appeared to be just an ordinary box with a window slit for ponies to watch the race from. From the inside, it was an explosion of fancy. Fancy wall art, fancy lights, fancy plants. There were even fancy odeuvres to snack on before the race!

As soon as the two ponies reached the viewing room, Fancy Pants was swallowed by an entourage of several ponies. Rarity was taken aback as each pony tried to strike up a conversation with Fancy Pants at exactly the same time.

"Everypony, this is Rarity!" he nearly shouted over the other ponies. "She's staying at the Canterlot Castle."

That got their attention.

Several of the ponies gasped and a few tried to speak directly to Rarity, but they were interrupted by the loud hiss of static over a microphone as the race commentator began to speak:

"Fillies and Gentlecolts! Welcome to the Wonderbolts Derby! Our competitors are taking their places at the starting line, and the race will begin momentarily!"

Excited, Fancy Pants exclaimed "I'll be rooting for Rapid Fire, of course. He's sure to take home the grand prize!"

Several of the ponies surrounding him nodded their heads in agreement.

"I don't think he stands a chance against Fleetfoot," something that sounded oddly like Rarity exclaimed.

Why ON EARTH would you ever say something like THAT?!

Fancy Pants' companions were completely shocked that anypony would ever dare to contradict him like that. Rarity smiled awkwardly to try to defuse the tension, but, fortunately for her, a trumpet blast signaled the race was about to begin.

Everypony gathered at the window to watch the start of the race.

A quick whistle-blast and the five Wonderbolts were off, whizzing around the track at incredible speed! The race was 25 laps, but at the speed the Wonderbolts were flying, the race was over in about eight seconds, making the race nearly impossible to follow.

"AND IT'S FLEETFOOT BY A NOSE!" The commentator roared as the first pony crossed the finish line.

Images of diamonds, rubies, emeralds, sapphires, and mountains of golden bits flooded Rarity's mind. "WOOHOOOOOOOOOO!" she shouted in spite of herself.

The other ponies in the room seemed not to notice, but Fancy Pants was impressed; "Bravo, Rarity!" he cheered. "I say, how did you know Fleetfoot would be victorious?"

Forgetting where she was, Rarity rambled, "My friend Rainbow Dash talks about her all the time! She says what Fleetfoot lacks in size, she makes up for in speed."

Somepony nearby was unimpressed, however. "And who is this Rainbow Dash?" she asked aloud.

"Oh, well.... She's... She's the Wonderbolts Trainer, of course!"

I HAVE GOT to get out of here. My money is calling my name! she thought.

Thinking fast, she called out, "Would anypony care to join me for a drink? I just have to go get something first..."

That night, there was a fire at Donut Joe's Bar.

This is what Princess Celestia's investigators were able to piece together from the incident:

At approximately 6:00 PM, several ponies dressed in formal attire arrived from the Wonderbolts Derby to have a drink. One young mare in particular, who has not yet been identified, was witnessed throwing a large bag of bits on top of the bar and shouting "Free drinks for everypony!" which was met with plenty of cheering. Typical party antics ensued, but several ponies reported the clearly well-to-do mare trying to "pin the tail" on everypony at the bar that night, including herself. After about six hours of partying and plenty of drinking, the owner and proprietor of the bar attempted to get the young mare and her friends to leave. The mare tossed a full glass of cider at the owner, which launched an extremely out of control brawl throughout the bar. A candle was knocked over in the chaos, igniting the wooden table it rested on and causing everypony to flee the scene.

All that is currently known about the suspect is that she was wearing a dress almost entirely studded with diamonds.

"T-t-twilight?" Rarity asked, stumbling towards the purple unicorn in the street.

It was well past midnight now, and all the heavily inebriated Rarity could think about was getting home. But, she couldn't possibly sleep well in her suite without telling her friend Twilight about her wonderful day first, now could she?

"Um, who do you think you are?" the clearly disturbed pony replied.

Placing a hoof around her dear friend, more for support than affection, Rarity was about to reply to the unicorn when a very odd sound came from her mouth instead:

BLAAAAAAAAAAAHHHHHHHHHHH

"OH MY WORD!" the terrified and vomit-covered pony screamed in horror. "GET AWAY FROM ME!"

Rarity couldn't understand why one of her best friends was behaving so strangely. Maybe she's just had too much to drink tonight she reasoned.

Aside from "Twilight," Rarity didn't run into anypony else on the way back to her suite. Even the guardsmen at the gates to the castle avoided her as she fumbled her way through the courtyard, around the keep, and up the hundreds of stairs to her bedroom. Though her stomach was feeling much better than it had been, Rarity's head still felt like it had been driven through a wall, and every footstep sounded like a violent explosion in her mind. The moonlight was absolutely blinding, almost causing Rarity to pass out from the pain alone. Every single fiber of her body ached in some way.

Nevertheless, it was the best day she had had in months, or even years for that matter. Everything about her day had been exhilarating, from meeting Fancy Pants, to winning 400 bits at the Wonderbolts Derby, to having a party at Donut Joe's Bar (how did that end again?), everything about her day was awesome.

And she owed it all to Rainbow Dash. Well, maybe not the bumping into Fancy Pants part, but winning a small fortune was 100% due to her Wonderbolt-obsessed buddy.

Her fuzzy brain struggling to formulate an idea, Rarity took out a piece of paper and wrote a letter to Rainbow before she passed out on her bed:

Rainbow, my dear, we need to have a serious conversation when I return to Ponyville. I won't say too much right now, in case somepony else sees this and gets the wrong idea.

But I just remembered I really like money, and you and I are going to get it. A lot of it.

Your friend,

Rarity.

Author's Note

Mostly exposition, but I really wanted to tie "Sweet and Elite" into the foundations of this story. I really think a Rarity-Rainbow Dash back alley partnership would be an interesting read, and I'll definitely be bringing RD into the fray soon. Thoughts in the comments below, please!