Everyday I'm Hustlin'

by Jabbie

Rating: mature
Tags: Dark, Romance, Slice of Life
Length: 4325

Rainbow Dash and Derpy Hooves need to raise money.

Derpy and Dash must come up with a way to help rebuild the destroyed roof of town hall. However Rainbow's methods for gathering the bits might put her and her friend in a much worse situation than she was originally in.

Published 1970-01-01 00:00:00 UTC
Last updated 2012-09-23 11:55:47 UTC

Chapter 1

Rainbow Dash and Derpy Hooves sat in Mayor Mare's office. Dash was clearly disgruntled and resisting the urge to leave. Derpy couldn't possibly be more nervous, knowing she was to blame. Moments later the mayor walked in and looked them over.

"Well, it seems your friend didn't raise the money like you thought she would, did she?" Mayor took a seat across from them and crossed her hooves.

Rainbow rolled her eyes and Derpy spoke up. "No, I guess she didn't."

"That's right, she didn't, and my town hall still has a collapsed roof that needs fixing before your next scheduled rain. That's five thousand bits this city doesn't have to spare. Who do you think's going to give me the money to fix it?" Mayor placed a hoof on her desk and tapped it impatiently.

"I'll tell you who: you two. Next rain is in eight days, so you'd better not disappoint me."

"Whoa! Why do I have to raise the money, I didn't do anything!" Rainbow snapped in her own defense.

"You should have supervised Derpy more carefully. You of all ponies should know the dangers of messing with storm clouds." Mayor held to her decision.

"And if I don't pay?" Rainbow stared her in the eye.

"Well, we'll just see what happens then won't we." Mayor narrowed her eyes and moved closer to the pegasus until their noses were nearly touching.

"Fine! Let's go Derpy!" Rainbow grabbed her less than comprehensive friend and dragged her out by the wing.

The two headed down the street and Rainbow continued dragging her friend although it wasn't necessary.

"So Rainbow Dash, how're we gonna raise the bits?" Derpy looked down at her hooves as she tried to keep her balance while being dragged.

Rainbow let go of her friend's wing as a thought entered her mind. Anytime anypony needed quick bits they always knew where to turn: Rarity. The proud blue pegasus, however, wasn't about to lower herself to the point of accepting the shady unicorn's dirty money. There had to be another way...

"I got it! Come on Derpy, we have a race to hustle." She jumped into the air, quickly taking flight, and the confused gray pegasus followed as closely behind as she could.

As she caught up to Rainbow, she decided to try and figure out exactly what was going on. "What's hustle mean Rainbow Dash?"

"It means we're going to scam 'em out of their bits. Trust me, I got this." The confident mare pressed forward and Derpy followed closely.

They soon landed in Fluttershy's meadow. "Wait here while I grab Shy to help us out."

The attentive gray mare did as she was told as Rainbow made her way to the door and knocked. She was soon greeted by a welcoming yellow pony.

"I'll explain on the way, but I need your help and I need you to follow me right now. We don't have a lot of time before the races start." Fluttershy took a moment to process what she had just been asked to do, then nodded and hesitantly followed Rainbow as she began to lift off.

As they flew into the air the cunning pegasus began to describe to her friends exactly what she needed them to do.

"Alright guys, listen up because this is important and if we're not careful things could get ugly. You two are going to watch and bet on the races, I'll be participating. Make sure you stay far apart from each other and no one sees you talking or anything like that; same goes for staying away from me. Fluttershy, you'll bet a hundred bits on who I signal you to bet on, you'll know who when I brush my tail across their back or side. Derpy, you bet fifty bits on me every time no matter what okay? Even when ponies start telling you its a bad idea, keep cheering loudly for me and betting just because I'm your friend. Got it?" Rainbow kept a slight distance ahead of her friends while she explained.

"Got it." The happy-to-help yellow mare answered quickly.

"Um, I got it too Rainbow." Derpy was less confident in her reply, but her friends were sure she knew what to do.

"One quick stop here - I have to pick up some bits for this." Rainbow swooped down to the ground and landed in front of a large windowless building.

She trotted in while Fluttershy and Derpy waited patiently outside, hovering a safe distance above the unfamiliar ground. Rainbow returned shortly with two bags of bits around her shoulder.

"Alright, take these, five hundred each, and remember the plan. I don't need you guys wasting these, this is all I have left. Now I'm about to tell you the most important thing of all, so listen close. I won't be able to know what my odds are set at, but when I'm five to one, casually combine whatever's left and have Derpy place everything on me. When you do that, Fluttershy, make sure you fly up and stretch or yawn in the air; that'll be my signal to win the race - alright?" The usually confident mare flew a little ahead of her friends, throwing a slightly nervous glance back over her shoulder.

"Alright, you can count on me Rainbow." Fluttershy was quick to promise her support.

"Me too Dash." Derpy followed suit.

Rainbow Dash's mind cleared once they saw the track in the distance. It was surprisingly large considering the poor community on this side of town, just beneath Cloudsdale but outside Ponyville city limits. Here the blue pegasus prompted her friends to split up and take different routes inside. They did as they were told while Rainbow made her way through to the center, pushing straight into the track lineup. Several other pegasi were warming up and doing stretches while they waited for the first race. Rainbow immediately sought out an older gray stallion who she knew was in charge. Given her reputation, she had no problem in being allowed to participate despite missing the signup deadline and tryouts by several days.

She began trotting around her competition, introducing herself and sizing each of them up. She glanced over the crowd to spot her two patiently waiting friends. Fluttershy was easy enough to distinguish from the large group of ponies with her bright pink mane and vivid yellow coat. Derpy on the other hoof was blending in surprisingly well, not that it mattered too much for now. Fluttershy was the one Rainbow needed to communicate with. As soon as she locked eyes with her gentle friend, she began to make her way to the starting line, casually brushing her tail across a dark green stallion's back as she passed.

The nervous yellow mare caught the signal and made her way to the ticket booth. She did as Rainbow Dash had instructed and placed a hundred bits from her bag onto the counter in front of a small window.

"Number seven please." She stated, hiding in her hair a little as the stallion in the booth stared at her through the glass.

"Here's your ticket kid - don't lose it. No refunds." He hoofed her a small marked card through a gap at the bottom of the window before calling to the next gambler in line.

Fluttershy looked down the line of dozens of similar bookmaker booths and noticed Derpy waiting in a queue at another one. She smiled when she realized everything would be going to Rainbow's plan; she was just happy to help in any way she could.

The excited gray mare happily trotted up to the window as the stallion ahead of her moved out of the way. She placed her bits on the counter and slid them beneath the window's gap. "Rainbow Dash!" She announced.

"That's great kid, but I need a number." The bookie informed her, impatiently moving a cigar around in his mouth and tapping on the counter.

Derpy thought for a moment - she had no idea. "Um, I'm not sure."

She looked over her shoulder and down at the pegasi lining up at the starting line, but Rainbow was too far away for her to clearly see the number she wore on her side. Just then a stallion tapped her on her shoulder, the same one who had been in front of her in the line.

"Rainbow Dash is fifteen, just so you know." He smiled and closed his eyes.

"Oh thank you sir. Fifteen then!" She cheerfully shouted at the bookie and received her ticket.

After having determined the potential skills of her fellow racers, Rainbow decided that the greatest challenge in this race was going to be losing it and making it seem like an unintentional loss. Scoping the track, she saw that there were no obstacles, only one sharp turn, and worst of all, the last hundred meters was a straight shot. It'd be way too easy to simply zip past anypony that was by some strange chance ahead of her. This was definitely going to be tricky, but she could do it. She'd done it with worse competition.

The precariously positioned pegasus knew she was going to upset a lot of ponies in the stands when she lost this race, and if it didn't seem legitimate, there'd be hell to pay. The countdown began, Rainbow lowered her head to her leg as she stretched one final time.

"GO!" A silver mare shouted as a flag dropped in front of the lined pegasi.

Rainbow took off with her expected display of rapid acceleration. She easily left all her competition far behind and heard the entire crowd cheering for her. She knew nearly all of them had bet on her and this was definitely going to play a key role in rapidly increasing her payout within the next couple races. She rounded the first wide corner with ease, deliberately slowing down as she turned but not letting it show. Another straight shot allowed her to regain her speed, but not before another pegasus caught up. He was a large brown stallion, while the much more slender green pegasus she intended to have win was close behind. As they reached the final turn, Rainbow pushed ahead, immediately gaining a good distance between them and herself. She took the turn hard, and nearly hit the wall as she fell to a very slow speed. She kicked off the wall and flew into the center of the track straight away. Just as she made it there, the brown pegasus smashed into her, not able to control his course of flight while taking the sharp turn.

Rainbow tumbled down towards the ground for a moment, then grabbed and kicked the brown pony away from her before she returned to the track. The green pegasus crossed the finish line first, Rainbow Dash a close second. The crowed exploded with rage, cursing and shouting at the brown pegasus who had crashed into Rainbow. They angrily crumpled and threw their losing tickets to the ground.

Fluttershy along with a few others returned to the booth to claim their prize money.

"You wanna let it ride kid?" The bookie asked, almost assuming she would.

"Oh, um... no?" Fluttershy insecurely answered, not exactly sure what he meant.

"Your call."

To the yellow mare's surprise, she was hoofed a bag marked for three hundred bits. Not questioning the actions, she took the payout and realized that's what Rainbow must have meant by five to one. The green pegasus was marked at three to one. After tucking the bits into a large bag, she returned to see what Rainbow would do next. The blue pony was clearly arguing with the brown stallion who crashed into her. She gave him a forceful push and two others made their way in between them to prevent a fight. Rainbow played her part well. She then made eye contact with Fluttershy and smiled before trotting over to a white mare and brushing her tail across her back. The mare looked over at Rainbow and gave her a subtle smile then winked, making the blue pegasus blush. That was not the reaction she had anticipated.

Fluttershy and Derpy placed their bets again. Before long, the six racers were off. Derpy stood at the edge of the stands, shouting and cheering for Rainbow Dash. She was accompanied by plenty of others, as Rainbow's odds were pushed from one-and-a-half to two to one. The shy yellow pegasus remained completely calm and simply enjoyed the show. As the pegasi neared the end of the race, the clearly spiteful blue pegasus made a point to cut off the brown stallion, causing him to quickly swerve to the left and over-correct into the wall. She did a good enough job making it seem like an accident as she rounded the last curve that she wasn't called off the track for it, but she would still be penalized for it. Rainbow crossed the finish line first, the white mare followed a couple seconds behind.

The crowd cheered wildly until the announcer spoke.

"Racer fifteen will be penalized five seconds for reckless maneuvers. Racer eleven wins first place, fifteen second place, seven third place, two fourth place, nine fifth place, and eight wins sixth place."

Once again a horde of angry ponies slammed their losing tickets into the ground. The bookies had already made quite the profit off Rainbow Dash today, and so paid no mind to the money Fluttershy was making. She quietly collected another three hundred bits and calmly walked back to the stands.

Another race went by, and this time Rainbow flew slowly and calmly made her way to the finish line in fourth place. It would seem to anypony else that her spirit was broken due to the recent losses. Once again the pony she signaled won and Fluttershy took her payout. She now had over a thousand bits sitting in her heavy pouch. Derpy was down to three fifty. This time when the yellow mare looked to the leader boards, she saw Rainbow's odds being pushed down to one in five, signifying a five to one payout. This was it.

Fluttershy quickly trotted to the stands and made eye contact with the waiting racer. There were only two races left and Rainbow was getting worried as she brushed her tail across the green stallion once again. However, that no longer mattered as soon as she saw her excited friend fly into the air and let out a long yawn with outstretched hooves. It was lucky the stands were well lit since the sun was setting and natural lighting was becoming more obscure.

Fluttershy casually made her way over to where Derpy was and bumped into her, placing her bag of eleven hundred bits into her chest. The gray mare subtly grabbed them and made her way to the booth.

"Fifty on fifteen again?" The bookie asked with a smile.

"Nope, all of it on fifteen." She dropped all her remaining bits on the counter: all one thousand four hundred fifty of them.

"Whoa, are you crazy kid? Well hay, it's your money right?"  The bookmaker took and placed the large bet, sliding over her ticket carefully. He'd be lying if he said he didn't feel bad for the obviously slow mare throwing her money away.

Derpy took it with a smile and trotted down to the stands. "Thank you!"

The blue pegasus was beyond relieved. Losing these races had begun to take its toll on her ego, something she couldn't easily let go. She know that she couldn't just blow the competition away like she wanted to however, so sadly she'd have to take it slow and at least make the race seem close. She lined up, and as soon as the flag dropped, she was off. She zipped past the competitors and into the front. As she reached each turn she took it slow so as not to make a scene. The racers slowly caught up, but Rainbow easily kept them behind her, and in a matter of moments she had secured first place without having gained too much of a lead.

Derpy trotted back up to the booth with a bright smile. The bookie was stunned, but he realized they had still made good bits off Rainbow Dash today.

"Here, take your payout and get out of here before someone catches on to what you're doing. I'd hate to see you get hurt kid." The bookie looked her warningly in the eye and slid a large sack across the counter.

The gray mare happily took the heavy bag and trotted off. She wished she could go fly down to Rainbow and celebrate, but knew it'd be impossible with one race left to fly. Instead she just waited and watched from near the exit. Fluttershy had received a complementary drink from an admirer and was clutching it between her front hooves while she watched her cocky blue friend mock her competition.

Once again Rainbow won the race without a hitch. Everything seemed to be going better than expected. She laughed and taunted her rival racers some more before flying off into the crowd. She passed directly over Derpy and stared down at Fluttershy. The three made their separate ways out of the track and eventually met up back near the Ponyville city limits.

"So how'd you guys do? How much did we make?" Rainbow excitedly asked.

Derpy Hooves dropped the heavy bag on the ground and prompted Rainbow to open it. At a five to one payout, they found themselves carrying just over seventy two hundred bits. Plenty more than they had hoped for.

"Yes! This went better than I thought it would, and look! Neither of you got killed." Rainbow playfully wrapped her forearms around her friends' necks.

She then reached into the bag and gave Fluttershy her fair share, five hundred bits.

The sweet yellow pegasus silently but gladly accepted the money with a tentative smile. She'd be able to treat herself and her animals to something special. For that she couldn't be more grateful.

"Thanks for your help, couldn't have done it without you Shy." Rainbow offered her a hug and turned to Derpy.

"You too Derp, you did good back there."

The three took turns sharing hugs and saying their goodbyes. Fluttershy flew off towards home, but Rainbow Dash urged Derpy to wait a moment.

"So, I was wondering. Maybe we can celebrate tonight's success before we give all our bits away to the stupid mayor tomorrow." The usually confident pegasus looked down and kicked the ground as she spoke.

"Celebrate like how, Rainbow?" Derpy smiled at the thought.

"Well, lets see. We can go grab dinner or something... together." The apprehensive blue pegasus looked over her shoulder and scratched her mane, not sure why she suddenly felt so shy around her old friend.

An equally nervous mare searched for a reply. "Um, that would be good. I like that idea."

"Great, I like that idea too! So... follow me, I know a great place." Rainbow slowly lifted off the ground with the flap of her wings, making sure Derpy was following closely.

As the two flew side by side in the night, the gray mare decided to try and make small talk to ease the awkward silence. "I'm glad we're friends again Rainbow, and I'm sorry I keep messin' stuff up."

"Haha, don't mention it Derpy, you didn't mess up at all today. Still, I'm sorry I get so mad at you so easily. You're pretty annoying sometimes though." Rainbow was often hard around the edges and she let it show as she joked and pressed an elbow into her sincere friend's ribs.

"Ouch, Dash, quit it!" The playful mare smiled and took Rainbow's taunts as a sign of affection, because she knew that's exactly what they were.

Derpy decided to fight back simply to take part in her friend's playful form of flirting, casually bumping her rump into Rainbow's side and causing her to lose her bearings for a moment. After a few seconds of over-correcting, the vengeful pegasus caught her stability and retaliated with a playful yet forceful rump bump of her own. The clumsy gray pegasus wasn't so quick to regain her stability, tumbling down and landing forcefully on a large cloud that luckily just so happened to be beneath her.

Rainbow quickly dived down to see if she was alright. "Sorry, I didn't mean to knock you out of the sky like that."

The cocky blue pegasus laughed as Derpy tapped on her own head to stop her eyes from spinning, half of her body stuck inside the large cloud. "That's alright Dash, you didn't mean it - right?"

"Of course not, here, let me help you up." As Rainbow pulled her friend out of the soft white fluff, Derpy lost her balance and fell back over, dragging the helpful pegasus down on top of her.

They lightly bumped noses as the rainbow maned pegasus tried to catch herself before crashing down on her friend. Their eyes met, and the pair wondered exactly how they had ended up in this awkward yet comfortable position. Rainbow Dash leaned in further until their lips were nearly touching. The young gray pegasus was torn between nervousness and excitement. She couldn't deny that she wanted to be with this sexy pegasus: there wasn't a pony in Equestria who would pass up a chance to hit the hay with Rainbow Dash. But this meant more to Derpy than that, this was something deeper than being simply sexual to her. It was easy to realize that as she felt her heart throbbing with joy while the mare she cared so much for was staring into her eyes. The warm breaths on her cheek and the soft mane dangling in her face lit her heart on fire, she wanted to stay here with Rainbow Dash forever as they stared deeply into one another's eyes.

Derpy knew what to do. She wasn't as dumb as everyone made her out to be - she was simply a little ditsy at times, especially around Rainbow. She was completely aware of what was happening and welcomed it. She did, however, suffer from performance anxiety, and not only that, she was extremely self-conscious of her eyes. Eye contact like this always reminded her that she was different in that sense. Not sure whether or not Rainbow even cared, she decided to put it behind her and fall into the moment.

Their lips touched and each mare closed her eyes to savor every second of their fist kiss together. Rainbow's thoughts were a mystery even to herself as she took in the sweet sensations of warmth and comfort her friend had to offer. Her mind raced between different scenarios and ideals: she thought she knew what she wanted, but she wanted so many different things at the same time. Derpy lifted her head to try and hold onto the kiss as Rainbow pulled away. She let herself fall blissfully back onto the cloud and began to look over her hesitant partner, who was showing an unusual weakness in her eyes, as her mane dangled across one side of her face and a deep blush rested on her nose. The normally strong blue pegasus looked down at the subject of her latest infatuation, who was by all means, very beautiful. Her golden blonde mane shone brilliantly in the moonlight and her gorgeous yellow eyes reflected the thousands of stars above.

"I'm sorry Derpy, I didn't mean to just... just kiss you like that. I don't know... why I..." Rainbow failed to complete the thought as she once again became captivated by the loving mare beneath her. Her flushed cheeks and lidded eyes took her breath away.

They blushing gray pegasus didn't reply. She knew her friend had meant to kiss her and was only saving herself form any potential rejection, even though there was no chance of that happening. Knowing Rainbow Dash, the ditsy mare figured in a minute or so she'd regain her confidence and begin pressuring her into having sex. Before Derpy could make a move of her own, she was met once again by a soft pair of blue lips pressing tightly against her own. She wrapped a hoof around the pony's neck and pulled her into the tender kiss. Rainbow pulled her passionate friend over on her side, wrapping a leg and wing around her. They continued to kiss, sharing their tongues while they discovered the soothing warmth radiating between their bodies. In the heat of the moment, the normally shallow blue pegasus felt something she'd never felt before and stopped, pulling her friend's head into her chest while she caught her breath.

"Why'd you stop Rainbow?" Derpy took this chance to catch her breath as well, although she'd gladly go the rest of her life without another breath as long as it meant she'd be kissing this amazing mare.

Rainbow pressed her chin down on her friend's mane, stroking it with her hoof. "I just don't want to take this too fast is all. Ya know?"

Derpy was shocked, but even more so, she was relieved to hear that. "Yeah Dash, I know."

Rainbow rolled over onto her back to face the stars while her loving friend tightly hugged onto her. The still excited gray pegasus began to nibble on her friend's ear with a smile.

"Hey, easy there." The ticklish pegasus giggled and turned to share another kiss.

"So how about that dinner then, huh?"

Rainbow Dash gave her friend a long uncomfortable lick across the cheek then quickly flew away. Derpy wiped her face and chased after her, disappearing into the night, having just found a new, deeper kind of friendship than she could ever have hoped for.