The Puppetmaster

by XSomeGuyX

Colt in a Conundrum

Previous Chapter

Colt in a Conundrum

                It was the start of a new morning for Cloudsdale and the start of the workday for the Cloudsdale Couriers. Their jobs involved making deliveries all over the cities, villages and even lone cottages of Equestria. There was nowhere too obscure or extreme that they would not deliver to. Unfortunately, this also meant their workday would always start early in order to ensure that the sterling reputation of the Courier Service stayed intact with their promise of next day delivery. This, of course, included the beige stallion, Cloud Slider.

“And… Cloud Slider…” the manager—or as a few of the couriers jokingly called her—their “Wrangler” said. “Looks like it’s your lucky day, you have only one package to deliver today.”

“Where to?” he asked.

“To…” the mare paused and stared wide-eyed past the beige pegasus. “Derpy!?”

“Hi, Miss Wrangler!” the grey pegasus greeted the manager.

Derpy had made it a habit to accidentally visit the Cloudsdale Post Office every now and then. The higher-ups of the office were always lenient on her and chalked up these visits as a force of habit from her days of living in Cloudsdale. Even if she occasionally made a mistake or two, they could not deny she more often than not got the job done. However, her visits were always thought to be ill omens, whether that meant she would do something to physically harm the office or just bad luck would follow the deliveries for the day.

The two other couriers working that day had taken off as soon as they heard the Derpy’s voice. Unfortunately for the Cloud Slider, he had not received the location of his delivery for the day nor the package itself, and could not just leave as easily as they did. He waited for his manager to regain her composure as she attempted to deny Derpy entrance into the office. Unluckily for her, Derpy was deceptively strong and busted through the doors that the manager attempted to barricade with her body.

“Ready for my mail for today!” Derpy exclaimed with a smile as she looked down at the courier’s manager. “The doors didn’t wanna open again? Don’t worry, I think I fixed them!”

“Yes… ‘fixed’,” the managerial mare sighed. “As we’ve told you before, Derpy. You don’t work here anymore. You work at the Ponyville Post Office!”

“Oh yeah!” Derpy said, after taking a moment to register the thought. “I always forget!”

“Too often, if you ask me,” the mare whispered under her breath.

“Whatcha say, Miss Wrangler?” Derpy asked curiously.

“Oh nothing!” the manager faked a smile and waved the question off. “Now, where was I? Ah, yes! Cloud Slider, your delivery is listed right here and it is in Canterlot. Please take Miss Derpy here and point her in the right direction back to Ponyville.”

“Wait, why do I have to…” Cloud Slider began.

“You will take Miss Derpy with you and you will go on to make your delivery for the day!” the “Wrangler” ordered as authoritatively as the young courier ever heard her. “Did I make myself clear?”

The frightened stallion could only nod as he shook violently.

“Now, Derpy,” the manager continued. “Please follow Cloud Slider, if you will.”

“Ok!” the carefree mare boomed as she followed the stallion through the damaged front doors. The manager sighed and went on to find a cloud-shaper to repair the office’s doors.


The six mares and Spike had waited an entire day after visiting their knowledgeable zebra friend to go off and find this “Cloud Slider” who, Spike claimed, knew a pony that was currently researching dragons. Not only was the trip to Cloudsdale a long one, but Twilight had quite worn herself out in her attempt to fix Spike’s age and simply did not have the energy to cast the cloud walking spell or even make the trip. They had decided to set off early to have the best chance of catching the courier before he left to make his deliveries.

“Are you sure about this, Spike?” Twilight asked the dragon as the ground bound ponies climbed into the hot air balloon. Due to his size, they were forced to leave him behind.

“Yeah, he said he knew a pony that was researching dragon, but he didn’t tell me where,” Spike answered, . “He did tell me that he worked for the ‘Cloudsdale Courier Service’. You might still be able to find him there.”

“Ugh… he’s one of those overrated delivery colts,” Rainbow Dash commented.

“What do ya know about the Cloudsdale Couriers, Rainbow?” Applejack asked her.

“All I know is that they go around and deliver packages and if they don’t report back in on time, they get in trouble,” Rainbow Dash answered. “At least on the Weather Team, as long as I got my work done, they didn’t care when I got it done.”

“Fluttershy?” the rest of the mares turned to the other pegasus in their group for clarification.

“She’s just a little cranky… they got mad at her for losing a lot of packages when she practiced her tricks and sleeping on the job,” Fluttershy explained softly.

“Hey! I gave them a show with their delivery!” Rainbow Dash snapped. “Not my fault if the packages couldn’t take on my level of awesome! And after a long day, I think I deserve a little nap!”

“Let’s hope that this courier is a little like you then, Rainbow, and doesn’t show up on time for work,” Twilight laughed.


“Ok…” Cloud Slider stopped as the two pegasi reached the outskirts of floating city.  “Ponyville is that way… ok, Derpy?”

“Alright!” Derpy nodded.

“You got that, right?” he asked. “Just fly that way and you should find Ponyville in no time.”

“Ok!” she exclaimed.

“Ok…” Cloud Slider paused for a second. “Bye, Derpy.”

“Bye!” Derpy waved.

Flying through the open air above the plains that separated Cloudsdale and Canterlot, the young stallion could not help but feel as though he was being followed. However, every time he would turn around to try and catch his stalker, there was never anypony there, only the occasional bird or cloud. About half way through his journey, the feeling became unmistakable and unshakeable, but not matter how often he looked behind him, he found no one. Not until his flight slowed to a paranoid pace did he finally receive a tap on his head from above. It was, of course, none other than the very pony he thought he had guided home, Derpy Hooves.

“Why are we flying so slow?” Derpy asked.

“I… what…” Cloud Slider found himself at a loss for words. “Derpy, why didn’t you go back to Ponyville!?”

“But Miss Wrangler told me to follow you…” Derpy answered, her smile drooping after his scolding.

“I-I’m sorry, Derpy,” he apologized with an exasperated sigh. “I didn’t mean to scream. I just thought somepony else was following me.”

“Like who?” the grey pegasus asked, perking back up.

“I don’t know,” he replied. “But I’ve been hearing stories about sky-pirates stealing stuff from ponies wandering around the plains like this.”

“Oh…” Derpy said.

“Let’s just get you back to Ponyville,” the stallion said as he changed directions.

“Or we could just ask them for a ride!” Derpy shouted as she pointed towards an airship hovering above them. Cloud Slider’s ears drooped as he saw the skull and cross bones that the ship had imposed on their black flag. Before they knew it, the two pegasi were surrounded by the ship’s raggedy-clothed crew.

“Bring them aboard! A courier should have booty aplenty! ARRR!” a large hatted, dirty bearded pony told his subordinates.

“See!” Derpy exclaimed. “Told you they would help and we didn’t even need to ask!”

In the blink of an eye, the two mail handlers found themselves stripped of all their belongings, securely tied up and being brought into the lower deck of the ship. Cloud Slider did not bother trying to explain what was actually happening as both were dropped carelessly on the floor.

“This is all he had on him, Cap’n!” one of the crew ponies handed the dirty bearded pony the courier’s saddlebags. “The mare had nothing to plunder!”

“ONE MEASLY PACKAGE!?” the captain yelled. “ARRR! It matters not! We shall fetch ourselves a mighty price from the ransom of these two ponies!”

“Wanna sing a song while we wait?” Derpy asked her fellow captive. “OH! One hundred barrels of cider on the wall, one hundred barrels of cider! Take one down, pass it around, ninety-nine barrels of cider on the wall!”

“This is going to be a long kidnapping…” Cloud Slider moaned as he hit his head against the floor.


“Alright… it should be right around this corner…” Rainbow Dash said as she led the group through Cloudsdale.

“Ya said that the last three times,” Applejack complained.

“Uh… darlings!” Rarity stopped the group as she turned her head side to side. “It seems that we have lost Twilight.”

“Where did she go?” Fluttershy asked.

“She’s over there!” Pinkie gestured as she happily took a bite from an inexplicitly obtained snow cone.

“If there is anything else you need during your visit, Princess,” a stallion dressed in well-pressed suit and tie began. “Please do not hesitate to ask. We are at your service, Princess Twilight Sparkle.”

“Actually… could you point us to the Cloudsdale Post Office?” Twilight asked the bowing stallion. “We’re a little lost…”

“Of course, Princess! If you need a guide as well, one can be arranged,” the stallion answered.

“No, no,” Twilight shook her head. “We just need directions to the Post Office.”

“As you wish, Princess,” the stallion bowed once more as he led the alicorn to a street and pointed out the city’s mail center. “It is right there, Princess. Straight down Nimbus Boulevard.”

“Thank you very much,” Twilight replied as she took the lead of her group.

“What was that all about?” Rainbow Dash asked.

“Well, it started when a few ponies noticed me and wanted to shake my hoof,” the purple alicorn began. “I didn’t mind. Did a lot more hoof-shaking back in Canterlot, but then the mayor’s assistant found me and wouldn’t let me go unless I asked for something. He wanted to apologize about not welcoming their ‘new princess’ properly.”

“Whatcha ask for, Twilight?” Applejack inquired.

“Pinkie was the one actually asked for something,” she answered.

“Yup!” Pinkie backed up Twilight’s story as she swallowed what remained of her snow cone.

“Do be careful with cold foods like that, darling,” Rarity advised. “They can easily give you a brain freeze.”

“A what freeze?” the pink pony asked as giddy as ever.

“Somethin’ tells me that she ain’t gotta worry about that, Rarity,” Applejack said, sharing a light laugh with the dress maker.

“Come on, girls!” Twilight called. “We’ve already wasted enough time with our little tour of Cloudsdale.”

It was short walk to the post office, and as they approached, they noticed a few pegasi working on the entrance of the office with a mare overseeing them. The mare had a very authoritative voice and it made her seem to be the one to ask about such matters as finding one of the couriers that worked for the office. However, as the group closed in on her, they realized that the mare was not in the best of moods as she barked angrily at the pegasi to work faster and gave a stern look to any pony who dared approach her. After one extraordinarily brave pegasus pointed behind her, the mare turned around and immediately relaxed her furrowed brows when she saw Equestria’s newest princess behind her.

“My apologies, Princess!” the mare immediately fell to the ground with a bow. “Is there something I can help you with?”

“I’m likin’ the new perks that comes being a princess, Twilight!” Rainbow Dash said, smiling cockily and elbowing the purple alicorn.

“Uh… Yes,” Twilight coughed. “We are looking for a courier that works here.”

“But as a Princess, you have access to the Royal Courier Service we provide to those in the royal family! You did not need to come all the way to Cloudsdale to find a courier!” the managerial mare told her.

“Well… I’m not looking to send anything,” Twilight explained. “We just needed to speak to a specific courier.”

“Oh… if that’s the case, I believe I can help you,” the mare said. “Do you know the name of the courier you wish to speak to?”

“Uh… yes… I think Spike said his name was…” Twilight paused, trying to recall the name. “Nimbus Rider…?”

“No! That wasn’t it! It was… uh…” Rainbow Dash interrupted. “Tornado Dancer…?”

“That wasn’t his name, silly Dashie!” Pinkie said as she cut in front of the blue pegasus. “It was Sky Walker!”

“Oh don’t tell y’all forgot his name already!” Applejack scolded.

“Ok then, why don’t YOU tell us what his name is!?” Rainbow Dash shouted back, pushing her forehead against that of the apple farmer.

“I… can’t remember either…” Applejack said, hiding her embarrassed face under the brim of her hat.

“Rainbow Dash, there’s no point in fighting about it,” Twilight intervened. “No pony can remember his name, only Spike knows it. Unless…”

“Yes, Twilight?” Rarity asked.

“Unless, either of you remember,” Twilight continued, looking to two members of the group that had stayed quiet until that moment. “Rarity? Fluttershy?”

“Hmm… let’s see,” the unicorn thought out loud. “I do believe Spike had said something about ‘clouds’.”

“Uh… I think it was…” Fluttershy spoke. “Cloud Sl… Slammer?”

“Well, we have a ‘Cloud Slider’…” the mare finally interrupted their desperate name search. “Is that the pony you were looking for, Princess?”

“Yes! That was it! That was what Spike had told us!” Rarity confirmed.

“Unfortunately, Princess, he has not checked in yet,” the mare admitted after checking a nearby clipboard. “He only had a single package to deliver today. He should be back soon enough, Princess. That is, if you feel like waiting.”

“I think we can wait,” Twilight answered for the group. “If it means helping Spike.”


“One barrel of cider on the wall! One barrel of cider! Take it down pass, it around! No more barrels of cider on the wall!” the crew and Derpy finished the last verse of their hours-long song.

“Is it finally over?” Cloud Slider asked, letting out a sigh of relief.

“Are we there yet?” Derpy whined. “I didn’t think Ponyville was that far away. If I don’t get back soon, who’s going to give Dinky her muffins!?”

“I don’t really think they were planning on taking us to Ponyville, Derpy,” the courier told her.

“Oh… Oh well!” Derpy smiled. “I can just fly back home!”

Just before he was about to explained how their wings and bodies were cocooned in rope, the binds that held her simply slipped off her body with no effort at all. It had become quite clear that they had not tied Derpy’s ropes and she had in fact been able to leave at any time she chose. She could have even quietly left for help or even untied Cloud Slider herself and helped him escape without the pirates being any the wiser. However, through her own aloofness, she had stayed in the ship for nearly half the day and, consequently, kept Cloud Slider there as well.

“YOU…” he shouted but immediately adjusted his voice to a harsh whisper. “You weren’t tied up all this time!?”

“Nope!” Derpy continued smiling. “Why?”

“Okay… listen carefully Derpy…” Cloud Slider whispered. “Try and untie these ropes… we can sneak away from one of these windows.”

The cross-eyed pegasus ambled over to the still trapped courier. Fumbling with the ropes’ ends, it became painfully apparent that she had no idea what she was doing. Instead of freeing him, she only managed to increase the tightness of the ropes around his body, causing his eyes to nearly pop out their sockets from the sheer pressure.

“S-sto-op…” Cloud Slider struggled to say as the blond pegasus released her grip on the ropes. “Ok… new plan! Go to Cloudsdale and tell Miss ‘Wrangler’ that sky-pirates kidnapped me! You got that?”

“‘Kidnapped’?” Derpy echoed. “That’s silly! If anything, they ‘coltnapped’ you! You’re not a goat!”

“That’s not the poi-” Cloud Slider sighed. “Can you just go and tell Miss ‘Wrangler’ that I’ve been ‘coltnapped’ then?”

“Ok!” Derpy replied.

For a moment, the courier felt relieved, finding hope in the form of the clumsy mailmare. However, that feeling soon faded as she flew to the deck above and began to bid everypony farewell. By some stroke of luck—or more accurately—stroke of stupidity on the part of the pirates above, Derpy was able to casually fly away from the airship without so much as order to stop as most were busy returning her farewells with their own goodbyes. Eventually, though, the captain realized their mistake.

“Arrr! You bunch of knaves let the airheaded lass get away!” the captain shouted at his crew.

“But captain, she did keep us entertained while she was here,” one of the crew spoke up.

“AH! That be true…” the captain agreed. “Then we shall let the young lass go, me maties! We still have the courier lad down below in the bilge! I’m sure we can still bring a hefty ransom for his return!”

“Bye, guys! It’s been fun!” Derpy said as the crew gave a final wave goodbye to grey pegasus.

“I’m doomed…” Cloud Slider said to himself as he banged his head against the wooden floor once more.


“This is taking forever!” Rainbow Dash finally broke the silence.

“He’ll be by shortly! I assure you!” the courier manager told her. “I am very sorry for the inconvenience, Princess!”

All of the mares had been waiting hours for the return of the courier that Spike met, but they had received no sign of him. Both other couriers had returned and were surprised to be suddenly interrogated by the princess and her entourage. After neither arrival turned out to be the stallion they were looking for, most of the group had had enough of waiting and wanted to either return to Ponyville or look for him themselves. However, Twilight chose to follow the advice of the manager of the couriers and wait for him to return. Nevertheless, Twilight could see the distress in the mare’s eyes over the long absence of the courier even as she instructed them to wait.

“Is everything alright?” Twilight asked the anxious mare.

“Yes! Everything is quite alright, Princess!” the mare said, giving her an half-hearted smile.

“Maybe we can help…” Twilight told the mare.

“Surely you have other, more urgent matters to attend to, Princess, than finding a missing courier,” she replied.

“Well, we do but they have to do with that courier,” Twilight answered. “So finding him would help both of us out!”

“Well, if that is your choice, Princess,” the managerial mare gave in. “Firstly, I’ve been having a bad feeling from the start of the day, ever since Derpy came to pay us one of her ‘visits’…”

“Derpy was here?” Rainbow Dash raised an eyebrow to that comment.

“Yes… as you can see, she left quite the impression on the front doors,” the mare answered. “Anyways, I had instructed Cloud Slider to show her the way back to Ponyville. But Derpy’s visits always seem to signal some bad luck to come for us. Most of the time it is some physical damage that is done to the office, usually by her, other times it can be missing packages. This time, however…”

“Yes…?” Twilight asked.

“Cloud Slider is not the fastest of our couriers, but he is one of our best,” the mare continued. “He has always reported in on time and has never failed to deliver a package. Him being late is rare, but this is very late already. We’ve also been receiving warnings of sky-pirates out in the large open area between the cities of Equestria. At first, they were just taking things from traveling ponies, but they’ve been growing a bit bolder as of late. They’ve been kidnapping ponies as well, holding them for ransom. Cloudsdale has made appeals to Canterlot for more guards between here and the cities, but the expanse is huge and it also seems that the ship the pirates have their hooves on is very advanced and has some sort of boost to it that allows them to leave the scene quickly after they’ve been identified. I was afraid that it was only a matter of time before they took one of our couriers as we often deliver to rather important and affluent clients.”

“So you think they kidnapped Cloud Slider?” Twilight asked.

“It’s possible,” the mare replied. “I am often quite hard on my couriers, but it is always in their interest. This time, I seemed to have ordered my courier into a net.”

“So what’re we waitin’ for?” Applejack asked. “Let’s go find him!”

“It is not quite that simple,” the mare said, stopping the group from leaving the post office. “As I’ve said already, the area where we believe them to be is very large. One lone ship is hard to find out there.”

“So there’s no way to find them?” Twilight asked.

“Maybe not. I won’t stop you from searching for him but none of the guards Princess Celestia has sent have been able to pin down these pirates,” the mare said as she stepped out of the group’s way.

“What should we do, Twilight?” Rarity asked.

“Well… Princess Celestia said that we are the guardians of Equestria, right? So I don’t think there should be a question about what we should do then!” Twilight answered confidently. “Besides, how else are we going to find out about the pony who’s researching dragons? Let’s go rescue us a courier, girls!”

“But how are we ever going to find those… pirates?” Fluttershy swallowed hard.

“With our eyes, silly!” Pinkie said as she rushed off. “Besides, it gives me chance to finally wear my eye-patches. Twilight got to wear one last time, now it’s my turn!”

“How do you have eye-patches planted up here in Cloudsdale, Pinkie?” Rainbow Dash asked.

“Oh silly Dashie, I brought them last time we were here!” Pinkie said, bouncing happily away. “I have plenty! Since you’re extra cool, you can have two!”

“AGH!!! Stop it, Pinkie! I can’t see!” Rainbow Dash said, trying to rip off the patches planted on both her eyes. She managed to remove them just in time to see a familiar face flying at her at a dangerous speed.

“Oh! Hi, Rainbow Dash!”  Derpy greeted the pegasus being firmly squeezed into the clouds below under her weight.

“Derpy?” Rainbow Dash managed to ask before disappearing below the clouds.

“Not to sound rude, but what are you doing here, darling?” Rarity asked.

“Hmm…” the grey pegasus rubbed her hoof against the underside of her muzzle. “I can’t remember?”

“Then maybe you should head back to Ponyville, Derpy…” Twilight suggested. “Before you cause anymore damage.”

“But… I think I had to do something… important…” Derpy strained herself to remember but gave up quickly with a smile. “Nope! Can’t remember!”

“Well, let’s head out, girls!” Twilight told the rest of her group. “We’ve got a long day of searching ahead of us if we want to find those sky-pirates…”

“WAIT! Sky-pirates!?” Derpy interrupted. “Hmm… No! Still can’t remember!”

“Ugh… I guess that means I have to skip my afternoon nap…” Rainbow Dash groaned as she broke through the clouds below the group’s hooves.

“Do you wanna come with us, Derpy!? We’re going to go battle some sky-pirates and rescue a damsel in distress!” Pinkie asked the grey pegasus.

“He’s a stallion, Pinkie,” Applejack corrected her.

“Then what am I supposed to call him!?” Pinkie shouted.

“I dunno, but he ain’t a ‘damsel’,” Applejack answered simply.

“Anyways, you wanna come with us, Derpy?” Pinkie invited the blond pegasus, hoppinh all around her.

“Sure!” Derpy answered as she followed them.

“Should we really have Derpy, of all ponies, tagging along, Twilight?” Rainbow Dash whispered to the purple alicorn.

“She was the last pony with Cloud Slider before he disappeared…” Twilight reluctantly answered. “Besides, we can use the extra wing power while we’re looking for the sky-ship.”

“Wait! Cloud Slider… Sky-ship…?” Derpy said suddenly as if the name triggered her memory. “Nope! Can’t remember a single thing!”

“Let’s hurry up and get this over with already…” Rainbow Dash said. “Can’t believe we’re going to all this trouble to save a delivery colt!”

“Oh come on there, Rainbow!” Applejack said. “It ain’t that bad. How about I give you a mug of cider from our first barrel of the season when we get back? On the house!”

“Now that’s something I can look forward!” the blue daredevil said as she licked her lips..

“Cider!?” Derpy gasped.

“Don’t worry, Derpy,” Applejack reassured her. “Ya can have some too.”

“No! I remember now!” the grey pegasus shouted. “Cloud Slider said to tell Miss Wrangler that he was being kidnapped… but I told him that he was silly. Kids are baby goats. He was being ‘coltnapped’!”

“He thought he was a goat!?” Pinkie laughed.

“You know where Cloud Slider is, Derpy?” Twilight asked surprised.

“I think so… last time I saw him, he was in this big ship with a whole bunch of nice ponies…” Derpy answered. “Their clothes were all torn up though and they smelled kind of bad. They couldn’t sing either!”

“What kind of ship was it?” Twilight inquired further. “What did it look like?”

“I think… it had a black flag… and some bones on it!” the grey pegasus answered. “It was all torn up too!”

“Do you remember where you saw it last?” Twilight continued her line of questions.

“Uh… maybe…” Derpy replied.

“That’s not much to go on…” Twilight said, a bit saddened by the dead end of Derpy’s memory.

“It ain’t much, but it’s all we got,” Applejack said with a strong pat on back for her alicorn friend.

“Perhaps if we bring her along, something else might jog her memory, Twilight,” Rarity told her.

“Well then, we don’t have any time to waste,” Twilight said with more confidence.


“It was this way!” Derpy shouted as she pulled the balloon in a sudden change of direction. “No, wait… This way!”

“Derpy!” Rainbow Dash snapped. “You’ve been making us change direction every two seconds!”

“Yes, darling!” Rarity yelled from the balloon’s basket. “Can you please try to remember where you last saw the ship?”

“Ooooooooh! You want me to take you to the ship?” Derpy asked. “Why didn’t you just say so?”

“ARRGH!!! It’s like having two Pinkies around!” Rainbow Dash screamed. “I… don’t know how long I can take this!”

“Uh… Derpy…?” Fluttershy said, panting heavily from their relentless journey all over rural Equestria.

“Sorry, Fluttershy,” Derpy apologized, momentarily losing her smile. “I was just having fun hanging out with all of you!”

“It’s fine, Derpy… but we’re on an important mission right now,” Twilight cried from the balloon. “So can you please take us to where you saw ship?”

“Sure! This way!” Derpy answered loudly, regaining her wide smile as she pulled the balloon all by herself further away from any town or city.

“What’s that?” Applejack said, spotting a small dot along the horizon.

“Avast! It be the scallywags that plundered our courier!” Pinkie yelled from the top of the balloon, looking through a small telescope she produced seemingly out of thin air. “Full speed ahead, buckos!”

“I think we’ve gone and lost Pinkie…” Applejack commented.

“But we found the ship!” Twilight interrupted. “Hurry, Rainbow Dash!”

“Already on it!” Rainbow Dash said, taking the lead.

“Ya ok there, Fluttershy?” Applejack asked the yellow pegasus who was plastered against the outside of the basket.

“Ready the cannons, lasses! Take no quarter!” Pinkie ordered, tying an Equestrian flag to the balloon.

“Pinkie, darling, I know you’re having fun playing a pirate and all but we don’t have any cannons!” Rarity yelled.

“Arrr! The strumpet be correct!” Pinkie said, sliding back down to the basket. “Then we shall board the enemy vessel!”

“What did you just call me, Pinkie!?” Rarity glared at the pretend pirate.


“Cap’n!” one of the crew yelled out from the crow’s nest of the ship. “We have a small craft coming our way.”

“Throw me the spyglass, matie! Let me see this ship!” the captain replied, spotting a hot air balloon proudly the Equestrian flag. “It be privateers, but they sail with a balloon, me maties!”

“What are yer orders, Cap’n?” the crew stood ready.

“Raise anchor,” the pirate leader told them. “There’s no need for a fight here, me hearties! A balloon can never hope catch the Rocket Wing!”

“Uh… Cap’n?” the lookout called out once more. “We might have a problem! The balloon is closing in on us!”

“Yer eyes be losing their keenness…” the captain said, taking another look through the handheld telescope to find the balloon being accelerated by only two pegasi. “Impossible!”

“They will be upon us any second!” the crew said, also observing the balloon from over the ship’s railing. “Cap’n?”

“We have no choice!” the captain shouted. “Man the helm! We will use the Rocket Wing’s secret weapon!”

“Alright, Rainbow Dash!” Twilight cried from the balloon’s basket. “Just a little closer and I can teleport everyone onboard safely!”

“No problem!” Rainbow Dash responded, speeding up her pursuit with Derpy surprisingly keeping up with her pace. “Al… most… there…!”

“What’s that!?” all those aboard the basket, minus Pinkie the Pirate, said in unison as they witness the ship apparently grow two large, red tubes on either side of its rudder.

“It appears to be a pair of rockets! ARRR!” Pinkie answered.

“Rockets?” Rarity repeated.

“Now, how in the hay do ya know that?” Applejack asked the pink pony, who simply smiled and shrugged.

“Hurry, Rainbow!” Twilight yelled out.

“It be too late, lasses!” the captain laughed as he signaled his crew to pull a lonely lever near the ship’s helm.

Just as the two pegasi pulled alongside the ship, it gained a sudden burst of speed, sending the entire balloon and the pegasi guiding it for a whirl. Those in the basket screamed as they held on to the basket for dear life, its violent spinning threatening to hurl them to the ground. Through her training—her training mishaps more so—Rainbow Dash was able to quickly regain her bearings and began attempting to stop the balloon. However, the two scatterbrains of the group seemed to be enjoying the uncontrollable spin.

“WEEEEEEEEEEEEEEEEEEEEEEE!!!” Derpy squealed happily as she allowed herself to ride out the whirl.

“HAHAHAHA! This be nothing compared to the storms I have braved on the high seas!” Pinkie laughed as she fearlessly stood on the outside of the basket.

By the time the blue pegasus finally slowed the balloon’s rapid rotation, the ship that was once with a stone’s throw was now a mere speck on the horizon. The group looked dishearteningly as the ship’s far off dot. However, Rainbow Dash narrowed her eyes at the slowly shrinking dot as she slipped free of the ropes binding her to the balloon.

“Guess that’s what the manager meant by ‘an advanced ship’…” Twilight said, finally regaining her composure.

“Rainbow?” Applejack asked, noticing the determined look on the mare’s face.

“They’re not getting away that easy!” Rainbow Dash said. “Come on, Derpy, Flutter…”

“I don’t think she’s feeling up to it right now, darling…” Rarity stated as they dragged the worn and dizzy yellow pegasus onboard.

“Well, if you can slow them down, Rainbow,” Twilight told her. “We can catch up as soon as Fluttershy has had some rest.”

“Then I guess it’s just me and you, Derpy!” Rainbow Dash said, grabbing hold of the grey pegasus. “Let’s get ‘em!”


The courier in the lower deck finally peeled off the wall as the ship regained a manageable speed. Throughout the boost, he had been pinned, face first, against the splintered wood of the inside of the ship’s hull. After hearing the ruckus from the deck above, he had wished it to be some sort rescue squad sent to retrieve him and stop the pirates. However, hearing the crew cheer and seeing one of them check up on him quickly diminished the only glimmer of hope he had of being liberated.

“I told you, buckos! As long as we have the Rocket Wing, no pony can ever hope to catch us!” the captain told his crew, all taking a swig of some mugs they had. “She’s the fastest ship around!”

“Cap’n!” the crow’s nest crew member called out. “Two pegasi approaching quickly from behind!”

“Arr! These lasses just don’t know when to give up!” the captain laughed.

“Should we use Rocket Wing’s secret weapon, Cap’n?” the crew asked.

“No need for that, me maties!” the captain shouted. “It be only two mares!”

The captain immediately gestured his pegasi crew members to gather the rope and prepare for the capture. The raggedy crew patiently waited for the two pegasi to close in and allow them a chance to incase them in rope, ideas of adding to their haul of hostages rushing through their heads. However, all instantly lost heart and became wide-eyed when they realized the speed at which their attackers were approaching. Unfortunately, they had no time to rethink their strategy as the duo blew past them, enwrapping them in their own bindings.

“Eh? She be a fast one!” the captain said to himself. “All hooves on deck!”

“Finally, some action!” Rainbow Dash smiled cockily. “I might just get to my afternoon nap after all!”

“Ooooo! Ooooo!” Derpy exclaimed, twirling in the air. “What should I do, Rainbow Dash!?”

“Uh…” Rainbow Dash stuttered, trying to find a task for the clumsy pegasus to do that would not cause some sort disaster for her. “You can… get the wheel!”

“I’m on it!” Derpy saluted playfully.

The blue rainbow easily outmaneuvered any and all of the floor-bound crew on board the ship. Not even the remaining pegasi not trapped in rope could even come so close as to touch her. Unfortunately, all she was able to do is keep them distracted. Were she to land and try to fight them herself, she would undoubtedly be overwhelmed by their sheer numbers. However, this was more than enough as she kept their attention from grey pegasus who whimsically approached the ship’s helm.

“Arrr! I’ve had just about enough of this little lass!” the captain yelled as he removed his large hat, revealing his glowing horn underneath.

A gasp escaped Rainbow Dash’s mouth as the captain shot a powerful magic blast. She just managed to dodge the short burst of magical energy but a quick follow up blast knocked her out of the air.

“I must say, lass! You are quite the flyer!” the captain told the downed pegasus. “Why don’t you come and join my crew? Be me first mate with all the freedom that you can ever want! No responsibilities, just open skies and booty aplenty! What do you say, lassie?”

“You’re kidding, right?” Rainbow Dash asked.

“No, lass! You’ve made quick work of me boys!” the captain remarked as he offered his hoof. “With your speed and the Rocket Wing, we’ll plunder all of Equestria’s treasures and the landlubbers will never know what hit them! What do you say?”

“Ha! In your dreams, pal!” the blue pegasus answered sassily, slapping away the captain’s hoof. “It’ll take a lot more than that for me to ever betray my friends like that… Besides, I don’t think that they let pirates into the Wonderbolts!”

“I see…” the captain said as he hung his head. “What a shame! Oh well, boys take…”

“I got it, Rainbow Dash!” Derpy interrupted the pirate leader, waving the ship’s wheel above her head.

“Cap’n!” some of the crew shouted from behind the blond pegasus as they attempted to grab hold of the broken wooden rod that the wheel once attached to, only to have their hooves riddled with splinters. “We’ve lost control of the ship! We’re headed to straight to Canterlot!”

“I didn’t mean literally get the wheel, Derpy!” Rainbow Dash told her, quickly taking flight once more.

“Lower the sails! Kill the propellers! Drop the anchor! Slow the ship!” the captain manically ordered. “We must not reach Canterlot! The guards will swarm us within seconds!”

It had seemed that in trying to escape the small balloon that chased them, the crew had inadvertently steered the ship into a direct course for Canterlot. The few pegasi crew members that remained immediately moved to the ship’s bow and pushed against it with all the power their wings would muster. However, even with the ship’s engines dead and sails down, the ship still retained much of its momentum and it was more than enough to resist any attempt made by the pegasi to slow it down.

An idea quickly formed in Rainbow Dash’s mind as she thought over the last sentence the captain had yelled. Should the ship reach the boundaries of Canterlot, the guards will be able to help in apprehending the pirates and save her and her friends the trouble. She quickly began to interrupt the pegasi in front of the ship and the grounded crew members heading for the anchor release with quick tackles and powerful kicks from her hindlegs. Her speed and agility made it easy for her to stop any and all their efforts to slow the sky-ship as well as avoid the captain’s magical blasts. Soon the regal city came into clear view and so did the guards. Unfortunately, Rainbow’s plan worked a little too well and the ship abruptly rammed through the guards that attempted to stand in its way.

Soon the seemingly unstoppable ship swept over the city, damaging the rooftops of many shops and homes with its hull as it passed by. The pirates found their ship on collision course with the royal castle of Canterlot. With no way to steer it from its current path or slow it down, most, including the captain, began abandoning the ship and jumping into the custody of the waiting guards below, leaving only the two mares onboard. Many of the guards began joining the pirates at the bow of the ship, attempting to stop the ship before it reached the regal structure. Seeing the effectiveness of her plan getting out of hand, the blue pegasus also lent her own wing power to stop the flying vessel.

The patrols along the castle’s walkways seemed almost oblivious to the ship headed right towards them; their usually boring and uneventful jobs had dulled their senses over time. Two guards in particular were more concerned with their conversation and remained ignorant to outside world. However, their little chit-chat was promptly cut short as they noticed a shadow darkening their surroundings. Turning their attention towards the skies ahead of them, they saw the ship slowly headed right towards them. Both instantly went into a shaky embrace as they clenched their eyelids and waited for their demise. Luckily for them, the Princess of the Sun had noticed the impending disaster they had not and immediately intervened, using her magic to slow the ship to a halt and save the terrified guards meant to protect her and the castle.

Both guards and pirates alike dropped out of the air, exhausted from stopping the ship from crashing into the castle. Rainbow Dash hesitantly looked below to the relieved Princess and fear-paralyzed guards. She wiped her brow and gave a deep sigh. Unfortunately, it seemed that her troubles were still far from over.

“Hey, Rainbow Dash!” Derpy called from the deck of the ship. “I found the break!”

“The break?” Rainbow Dash asked herself.

Flying back onto the deck and looking towards the airheaded pegasus, she saw that she was gripping a lever near the location of the ship’s former helm. A memory of the pirates pulling the same before the ship gained its rocket boost flashed through her mind as her eyes widened and pupils shrunk.

“DERPY, WAIT!” Rainbow Dash called. “DON- ”

It was too late. Derpy had already pulled the lever. The ship gave a quick jerk forward before slamming into the castle with the full force of the rockets. Thanks to the quick reflexes of Princess Celestia, her and her guards were magically flashed far from the impact point. No pony seemed to be hurt from the crashed, but the same could not be said about the once beautiful castle. That is except for the poor courier below the deck of the ship who was hurled out of the destroyed hull and ricocheted against the debris of the castle, eventually landing on a walkway below.

“I-I’m alive!” Cloud Slider cried as he bounced against the floor in joy. However, his happiness was short lived as an anchor soon came crashing in from above and crushed him under its weight.

“HI, PRINCESS CELESTIA!” Derpy waved from the half-destroyed ship’s anchor release, while the other pegasus aboard struggled to remain conscious.

“Princess!” Twilight called from her balloon’s basket as the remainder of the group finally caught up with the ship. “Uh-oh…”

“Oh my…” Rarity commented as the rest of the group saw the accident.

“Aww… I didn’t even get to say: Prepare to be boarded!” Pinkie whined.