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Cloudcover in: The Shipping Crusades

"Okay students, settle down!" Miss Cheerilee sang as she trotted into the classroom.  "You all know what today is, right?  It's time for another Family Appreciation Day!"

A few of the foals in class perked up upon hearing the announcement.  After all, Family Appreciation Day meant a guest speaker was coming, which in turn meant the day's lecture was cancelled.

Cheerilee smiled.  "Good, I see I've gotten everypony's attention," she said.  "So today, we'll be meeting a family member of one of our newest students, Pipsqueak."

At the back of the class, Pipsqueak flattened his ears shyly against his head.  "Um, Miss Cheerilee?" he piped up hesitantly.  "I'm sorry, but… my uncle's going to be a little bit late.  He dropped by this morning as I was on my way to school and told me he had to take an assignment from work, so…"

Pipsqueak trailed off, but Cheerilee did not seem perturbed.

"Well, that's fine Pipsqueak," she said.  "One's job does come first.  Besides, this will give us time to finish yesterday's math lesson!"

The class groaned collectively and Pipsqueak shrank back in his chair a bit as several glares were directed at him.  Slowly, the students rummaged through their saddlebags and retrieved their math textbooks.

Over the next hour, Pipsqueak tried to listen to Cheerilee's lecture, but he found it hard to concentrate.  His mind was too full of thoughts about the class's reaction to the guest he had selected.  After all, his uncle had a somewhat unusual occupation.  

A rapping at the classroom door startled the colt out of his thoughts.  Most of the class looked up expectantly.

"Oh, that must be our special guest!" Cheerilee said.  "You all may close your books for now while we turn our attention to our speaker."

Cheerilee opened the door, and smiled pleasantly as a white pegasus in a green beret walked into the classroom.

"Hello," Cheerilee said.  "You must be Pipsqueak's uncle.  It's a pleasure to have you here for Family Appreciation Day."

"It's a pleasure to be here," the pegasus responded.  "Where is Pip, anyway?"

He glanced around the room, spotting his nephew in the back row.  "There he is!  How are you doing, Pip?"

Pipsqueak smiled.  "I'm just fine, uncle Cloudcover!"

"Great," Cloudcover said.  "So sorry I'm late; the boss had another assignment and the others were all already busy.  But now that that's cleared up, we can get started!"

"Wonderful," said Cheerilee.  "Mr. Cloudcover, why don't you tell us all about your occupation?"

Cloudcover grinned.  "Well, of course," he agreed.  "As Pip knows, my job is a little different than that of most ponies.  I don't work at any normal business; my job is actually different every day.  I travel all over Equestria helping various ponies in need-"

"Like a superhero?" Scootaloo asked excitedly.  "Do you save ponies in awesome ways, like Rainbow Dash?"

"No, not quite like a superhero," Cloudcover laughed.  "My job is a little harder to explain, but I've been talking with my boss and my wonderful coworkers, and figured out how best to explain it to you all."

He took a deep breath.  "You see kids, I work at a small, Ponyville-based establishment called Equestria Speedy Shipping Services…"


To Pipsqueak's relief, Cloudcover really had spent a fair amount of time preparing for his speech, and his method of describing the shipping profession to the students was not unlike the one Ditzy Doo had used to explain it to Dinky.  The whole class seemed riveted by the idea of such an unusual job; even Diamond Tiara and Silver Spoon seemed to be listening respectfully.

"…and that's basically how it works," Cloudcover said, bringing the explanation to a close.  "A small group of us are given assignments almost every day to help ponies bring their relationship ideas into reality.  It's a lot of work, but it's a great feeling to see the ponies you helped starting off on a whole new relationship."

Cloudcover finished his speech, Cheerilee and the students applauded.  A few fillies in the front row exchanged excited glances.

"Wonderful!" Cheerilee said.  "Thank you for joining us, Mr. Cloudcover, and thank you Pipsqueak for choosing such an interesting guest for us today."

Cloudcover smiled humbly.  "Thanks, ma'am. It was a pleasure to be here."

Cheerilee nodded.  "Okay, students, it's time for recess!" she announced.

Cloudcover leapt into the air to avoid the stampede of foals beneath him as they all charged outside.

"They're so full of energy," he commented.

"Well, you know how foals their age can be," Cheerilee said.  "You'd better go outside and say goodbye to your nephew before you head back to work."

"Ah, right," Cloudcover said.  "Thanks again for letting me visit."

The pegasus turned and trotted out the door, unaware that his otherwise average day was about to descend into chaos.


"Did ya hear that girls?  Did ya?" Applebloom giggled, jumping excitedly around her friends.  "That stallion's got a job as a shipping pony!  We gotta go talk to him; I reckon that this is an opportunity we aren't gonna find anywhere else!"

"Who cares?" Scootaloo groaned.  "Who would want a job like that anyway?  Helping ponies with their namby-pamby lovesick fantasies?  Yuck.  Besides, haven't we had enough of that after what happened with Cheerilee and Big Mac last Hearts and Hooves Day?"

"This is different," Applebloom argued.  "Pip's uncle helps ponies who actually want help with their relationship… unlike Miss Cheerilee.  And he does it with methods that don't involve brainwashing love potions."

"We should at least go talk to Pipsqueak," Sweetie Belle said.  "I mean, do you girls remember that time we were helping Dinky and Twist spy on Dinky's mom?  That paper we found mentioned Equestria Speedy Shipping Services… the same place Pip's uncle works!"

"Hey, you're right!" Applebloom realized.  "We need to at least ask Mr. Cloudcover if he knows Dinky or Mrs. Doo."

"Oh, alright," Scootaloo agreed, "but just because we haven't heard much about Dinky lately."

"That's the spirit, Scoot," Applebloom said as she led the crusaders across the schoolyard.  The three fillies hesitantly approached their classmate, who was still in conversation with his uncle.

"Hi, Pip," Sweetie Belle greeted.

"Oh, hi girls," Pipsqueak replied.  "Did you like uncle Cloudcover's presentation?"

"Did we ever!" Applebloom said.  "Your uncle has a really cool job, Pipsqueak."

"Yeah, if you like that sort of thing, I guess," Scootaloo said.

"Actually, Mr. Cloudcover," Sweetie Belle continued, "we wanted to ask you something.  Does Mrs. Doo work at the same place as you?"

"Oh, you mean Ditzy," Cloudcover laughed.  "Yes, Ditzy is actually our most successful employee.  Her daughter used to go to this school, or so Pip tells me."

"Yep, but I only get to see Dinky on the weekends now," Pipsqueak said.

"So that was the big secret," Sweetie Belle said to her friends.  "Dinky's mom was trying to hide the fact that she was working at Equestria Speedy Shipping Services for a while."

Cloudcover nodded.  "Yes, but that was all sorted out eventually, of course," he said.

"So, do you really travel all over Equestria to help ponies in love every day?" Applebloom asked.

Cloudcover smiled proudly.  "Yes, there's a lot of adventure and strategy in this line of work.  Being a shipping pony isn't as easy as it might sound; you have to be ready to work with any kind of pony, and to deal with a new situation every day."

Applebloom and Sweetie Belle exchanged glances.  "Are you thinkin' what I'm thinkin'?" the earth filly asked her friends.

"That maybe we don't have our Cutie Marks because we're actually meant to be shipping ponies?" Sweetie suggested.

Applebloom grinned.  "I think it might be time for the next Cutie Mark Crusade."

"Whoa, whoa, hold it!" Scootaloo interrupted, wedging herself between her two friends and forcing their huddle apart.  "That would be the lamest thing ever!  What kind of pony would want a cutie mark for a job like that?  You girls know I hate all that gushy lovey-dubby stuff."

"But Scoot," Applebloom countered, "they mentioned adventures!  We wouldn't just be helpin' ponies… we'd get to go to parts of Equestria we ain't ever seen before."

"And the helping ponies part isn't as mushy as that," Sweetie Belle added.  "It sounds like fulfilling the other pony's request takes a lot of skill.  You might even have to spy on the target pony to find out some crucial information.  And we both know you like spying, right Scootaloo?"

Scootaloo shifted her weight.  "Well… yeah, but-"

"Besides," Applebloom interrupted, "you always get to pick what we do to look for our Cutie Marks.  We've been all over Ponyville, and done all sorts of crazy and dangerous things just because you suggested them.  Can't Sweetie and I pick what we're doin' for once?"

Scootaloo sighed.  "Fine, we'll give it a shot," she agreed, though she didn't look happy about it.

"Now hang on there, kids," Cloudcover said nervously.  "I know you all have big plans in the works here, but you can't exactly just walk into town and expect to find a pony who needs relationship help."

Applebloom nodded.  "Believe it or not, we've already learned that lesson…"

Pipsqueak's eyes lit up as he was suddenly struck with an idea.  "Hey uncle Cloudcover!" he began.  "What if we all go to Equestria Speedy Shipping Services!  Do you think your boss would let the four of us come on an assignment with you?"

"What?!" Cloudcover gasped, backing up slightly.  "Now Pip, I'm not sure that's a very good idea…"

"Aw, come on, Mr. Cloudcover!" Applebloom said.  "The three of us won't be any trouble!  Honest!"

"And if you let us come along, we might finally be able to find our Cutie Marks," Sweetie Belle added.

Cloudcover turned his head, glancing back and forth between the four eager foals.  Finally, he hung his head in defeat.

"…Fine.  After class we'll walk over and see what Dr. Candyfloss says."

I'm in the clear now, Cloudcover thought to himself.  There's no way Candyfloss will think sending four foals along on a shipping assignment is a good idea!


"I think that sounds like a wonderful idea!"

Four foals smiled in excitement, and one pegasus buried his face in his hooves in sheer disbelief.

"But boss," Cloudcover attempted to argue, "just think about this.  Shipping can be a very delicate profession.  Do you really think sending four completely untrained foals along on a shipping assignment is a good idea?"

Candyfloss chuckled.  "As I recall, Mr. Cloudcover, we all have to start somewhere," he pointed out.  "When I sent you out on your first assignment all those years ago, did you have any prior experience?"

"Well, no… but-"

"And I believe your nephew has seen you at work in the past, so if anything, he's more prepared then you were on your first day!"

"But what about the others?"  Cloudcover asked.  "These three fillies… they don't know a thing about shipping!"

"What does it matter?" Candyfloss asked calmly.  "It's not like we're sending them on their own assignment.  They'll be chaperoned by an employee, of course."

"But they're only foals-"

"Yes, but foals are not inherently inept," Candyfloss argued.  "They are often just in need of the right guidance.  I'm confident that even foals could benefit from an experience like this, provided they are shown the proper process by a calm, level-headed instructor, such as you."

Cloudcover was unable to come up with a response.

"It's only one assignment, my friend," Candyfloss added softly.  "It's not like we're hiring the lot of them permanently or anything, although I daresay if one of them turns out to have some natural talent for this, we could definitely make them a future prospect!  But for now, it will provide a rich and educational experience for them."

Cloudcover sighed.  There really was no way to win an argument with somepony like Candyfloss.

"Okay.  I'll let them tag along."

"Excellent," Dr. Candyfloss said, beaming as he noticed the smiles on the faces of the four foals.  "I already know Pipsqueak, but you three are Applebloom, Sweetie Belle, and Scootaloo, correct?"

The Crusaders nodded, and Candyfloss scribbled something briefly onto one of his records, and then tucked it away into his overflowing file cabinet.  "I hereby dub the four of you temporary interns at Equestria Speedy Shipping Services.  Cloudcover is your direct superior, and you shall do whatever he says in regards to your shipping assignment.  Is that clear?"

"Yes sir!" the Crusaders and Pipsqueak all chanted in unison.

"Very good," Candyfloss said, scrawling the address of the next client onto a sheet of paper and passing it to Cloudcover.  "I wish all five of you the best of luck on today's assignment."

"Thank you, sir!" the four foals giggled as they trotted out of the room.

"Yeah… thanks a lot, boss," Cloudcover mumbled.

Candyfloss winked.  "Don't be such a spoilsport, Cloudcover," he said.  "You've been an employee here longer than any of your coworkers.  I know you can handle this."

Cloudcover just nodded and trotted from the room.


Cloudcover trotted up the steep pathway leading to the address Candyfloss had indicated, listening to the chatter of the four foals behind him.  His stomach knotted as he thought of the potentially disastrous events that could come to pass once they reached their destination.  The young ponies trotting along behind him seemed as eager as ever, unaware of his uneasiness.  There was clearly no way out now; he would just have to trust Candyfloss's judgment and hope the four of them didn't completely ruin the assignment.

Cloudcover arrived at the house.  "Well, here we are kids," he said uneasily.

The house seemed average enough, but it was situated near the edge of a steep cliff.  Below was a vast valley, mostly hidden in shadow, since the city of Cloudsdale floated directly above.

"Cool," Scootaloo said, looking up at the cloudy citadel.  "I wish the assignment was actually in Cloudsdale."

"Then what would the rest of us do?" Sweetie Belle asked.  "You and Mr. Cloudcover are the only pegasi here."

"Oh, yeah," Scootaloo replied with a sheepish smile.

"The four of you just stay back there and let me talk to the client," Cloudcover instructed.  "Then you can help."

Cloudcover reached up and pounded on the door with a hoof.  A few seconds passed, and then suddenly the door was yanked open, revealing one of the most intimidating mares Cloudcover had ever laid eyes on.

The resident of the home was a pale purple pegasus with a wild, spiky, whitish mane and a shooting star as a Cutie Mark.  Her purple eyes were outlined in a bit of dark makeup, which accentuated the glare she was giving her visitors.

"What do you want?" the mare asked irritably.

"Erm…" Cloudcover began, trying to regain the composure he had lost when he encountered the somewhat frightening mare, "…hello, ma'am.  Did somepony at this address contacted Equestria Speedy Shipping Services?"

The mare's face contorted into barely concealed rage.  "Excuse me one moment, sir," she said, quickly closing the door.

Cloudcover waited.  Despite the fact that the door was now closed, the mare's voice was still clearly audible.

"Flitter!  I told you not to call those guys!  For the last time, I'm not in love and I don't need a stupid shipping service!"

There was a high pitched giggle.  "Oh, stop pretending sis," came another new voice, which sounded considerably friendlier than the first one.  "You're completely head over hooves for that stallion.  Since you weren't going to do anything about it, I went ahead and did it for you.  Now let the poor shippers in."


"Fine, then I will."

Hoofsteps sounded behind the door, and it opened once again, this time revealing a much less disgruntled-looking pegasus mare.  She had the same pale purple coat and eyes as the first mare, but her mane was a light aqua color and neatly brushed.  Her Cutie Mark was a trio of dragonflies, and she wore a rather large pink bow atop her head.

"Ooh, hi there!" she said sweetly.  "You must be from the shipping service!  Come on in, and don't worry about what my sister says; she's just a little grumpy."

The other, more irritable mare, who was standing some feet away, narrowed her eyes.

The friendlier of the two glanced behind Cloudcover and noticed the presence of the foals.  "Um… are they with you?" she asked.

Cloudcover nodded.  "It's a sort of trial program," he explained.  "I get to show my nephew and his three friends the ins and outs of this job."

The mare smiled.  "Well in that case, why don't the five of you sit down in the living room, and I'll bring you some refreshments."

That got the attention of the Crusaders and Pipsqueak, and they darted past Cloudcover and into the house.  A few moments later, the five of them were seated comfortably inside, as the cheerful mare approached with a fresh plate of cookies.  She grinned as the foals dug in to the pile of sweets.

"My name's Flitter, by the way," the mare mentioned.  "I actually called on behalf of my sister.  She claims she doesn't need your help, but she does."

"I do not," came the sister's voice from the next room.

"Nice to meet you, Flitter," Cloudcover responded politely.

Flitter giggled.  "Ooh, I love your accent," she laughed.  "Wait, don't tell me… you're from Trottingham?"

"Why yes," Cloudcover replied, pleasantly surprised that another one of the locals recognized his accent.  "Anyway, you can call me Cloudcover."

Flitter blinked in surprise.  "Huh?  You're name's Cloud…cover?"

"Yes… why?"

"Well, this might get a bit confusing," Flitter laughed.  "My sister's name is Cloudchaser."

She frowned.  "Speaking of which, why don't you show some common courtesy and get in here, Cloudchaser?" she called.

Cloudchaser walked slowly into the room and sat down across from her sister.

"So," said Applebloom through a mouthful of cookie.  "Can you tell us any more about the assignment you called us over here for?"

"Sure," said Flitter, ignoring her sister's scowl.  "Cloudchaser here really has it bad for this stallion named Thunderlane."

"You're acting like I'm obsessed with him!" Cloudchaser argued.  "I just think he's cool, alright?"

"Whatever," said Flitter in a singsong tone.  "So the problem is, Cloudchaser here is a little afraid to make a move and ask Thunderlane out herself, and now if might be too late."

"Too late?  What do you mean?" Cloudcover asked.

"Well, recently Thunderlane's been spending a lot of time with this other mare who moved into Cloudsdale a few months ago named Blossomforth," Flitter explained.  "There's no evidence that they're a couple yet, but they probably will be if Cloudchaser doesn't toughen up and ask him out first!  But now she's even more worried because of the potential competition, so it's not likely that she'll work up the courage to ask him any time soon."

Flitter grinned mischievously.  "Isn't that right, sis?"

Cloudchaser pushed her bangs out of her face.  "Well… yeah, but so what?  I just get a little nervous around Thunderlane.  But who wouldn't?  I can't help it that he's so fast and strong and suave and… uh…"

"And totally hot?"  Flitter asked.

Cloudchaser blushed furiously.  "Well… kinda…"

Flitter laughed again.  "So, that's why we called you guys," she concluded, turning back to Cloudcover and his assistants.  "Do you think you can set Cloudchaser up on a date with Thunderlane before Blossomforth steals him from under her nose?"

"Perhaps," Cloudcover answered.  "But first we have to-"

"Oh, oh, I know this part!" Pipsqueak interrupted.  "We can't take the assignment unless the actual client agrees, right?"

"Correct, Pip," Cloudcover said.  "Miss Cloudchaser, I realize you are hesitant to accept our help, and we will not pursue this if you don't want us to, no matter what your sister says.  Policy is policy, you know."

Cloudchaser sighed.  "Well, you did come all the way out here," she admitted.  "And I'm sure the little interns you have there would be disappointed if I rejected you.  So… since Flitter is technically right about everything she said, I guess there's no harm in letting you-"

"Cutie Mark Crusader Shipping Ponies, YAY!" the Crusaders cried suddenly, startling the other assembled ponies.  The three of them crowded around Cloudcover, and Scootaloo yanked Pipsqueak into their huddle as well.

"Okay, boss," Sweetie Belle said, "what's the plan?"

Cloudcover admired the eagerness of his interns, at least.  "Alright, here's what I think we should do," he said.  "Some of us are going to need to go to Cloudsdale and try to find out a little bit more about Thunderlane, as well as this Blossomforth we keep hearing about.  We can't all go, since most of you can't walk on clouds, and I can't exactly carry the whole lot of you around on my back."

Cloudcover glanced over at Flitter, who was still standing across the room with her sister.  "By the way Flitter, what can you tell me about this Blossomforth?  What does she look like?"

"Oh, she's kind of a cutie," Flitter said.  "You know, a little white pony, pink and green mane, flowers as a cutie mark."

"She sounds a bit more… uh… feminine then your sister," Cloudcover observed.

Both Flitter and Cloudchaser nodded.

"Maybe Thunderlane is more attracted to the more girly mares," Cloudcover suggested.  "That gives me an idea."

He turned to the group of ponies gathered around him.  "Girls, why don't you three stay here?  I need you three and Flitter to, uh… give Cloudchaser a bit of a makeover."

Cloudchaser's eyes widened in panic.

"Nothing too extreme," Cloudcover said hastily.  "It's just that currently, she's a bit… oh, how do I put this…"

"She looks like a total punk," Flitter said, ignoring her sister's glare.

"Well then, we just need to make her a bit less, um… punkish," said Cloudcover awkwardly.  "You can handle that, right?"

Applebloom and Sweetie Belle nodded, but Scootaloo looked irate.

"Hang on there, buddy," the pegasus filly piped up.  "There's no way I'm gonna sit here and help these two turn that awesome-looking pegasus into a pretty princess while you two go to the greatest city in Equestria without me!  I'm coming to Cloudsdale too!"

Cloudcover put a hoof to his chin.  "Come to think of it, having another pegasus along could be useful," he admitted.

"Exactly," Scootaloo said.  "I can help you guys get some good dirt on Thunderlane and Blossomforth!"

"Alright, it's settled then," Cloudcover said.  "Applebloom, Sweetie Belle, and Flitter will help Cloudchaser get herself looking a bit more presentable, while Pipsqueak, Scootaloo, and I head to Cloudsdale.  We'll meet back here later."

"We've got everything under control here," Flitter said, winking slyly in Cloudcover's direction.  "Just take those two and go do what you need to do."

Cloudchaser glanced rapidly between her sister and the shippers.  "Why do I suddenly have a bad feeling about this?" she asked uneasily.

"Too late for second thoughts!" Flitter giggled.  "Operation Thunderlane is underway!"


"You two are... whew... heavier than I thought," Cloudcover gasped as he beat his wings furiously to try to lift himself and the two foals on his back up to the edge of Cloudsdale.

"I can get off once we get there," Scootaloo pointed out.  "I can walk on clouds just fine!  I just… can't fly."

Cloudcover sighed with relief at the thought.  A few strenuous minutes later, he finally landed on the fluffy outer rim of the city, where he collapsed for a few moments to catch his breath.  Scootaloo hopped off and looked around the city in awe.

"Aw, yeah!  This place is every bit as cool as I'd hoped!" she said excitedly.  "I've wanted to visit Cloudsdale for ages!"

"No time for sightseeing, I'm afraid," said Cloudcover, groaning slightly as he staggered to his feet with Pipsqueak still on his back.  "We need to find this Thunderlane fellow."

He frowned.  "Unfortunately, I'm not exactly sure what he looks like," he admitted sheepishly.

"Oh, I know who he is!" Scootaloo announced, hopping around excitedly.  "I've seen him around Ponyville before.  He's easy to spot."

Scootaloo ran off toward the center of town, and Cloudcover, with no other real option, trotted along behind.  The filly stopped very suddenly, and he only just barely managed to avoid crashing into her.

"Shh!  There he is!" Scootaloo whispered.  "I don't have any good disguises in my saddlebag, so these will have to do for now!"

Scootaloo handed two pairs of ridiculously large sunglasses to Cloudcover, motioning for him to pass one along to Pipsqueak.  Cloudcover decided it was better not to question the filly's logic for now.

Once he had donned the 'clever disguise', Cloudcover looked at the pony Scootaloo was indicating.  He was a very athletic looking pegasus indeed, with a dark coat and mohawk-style mane.  He looked tough and headstrong; a strangely perfect match for Cloudchaser, at least in appearance.  But yet, this stallion was supposedly spending time with a much more ladylike mare.

"What do we need to do now that we've found him?" Pipsqueak whispered to his uncle.

"I'm not sure," Cloudcover responded.  "It would be more useful if we could see what he does when he encounters the other mare in question."

"Oh, hey Blossomforth," Thunderlane said, smiling at a cheery-looking mare that had just exited a nearby market.

Cloudcover blinked in surprise.  "Well, that simplifies things, doesn't it?"

"Hi there, Thunderlane!" Blossomforth giggled.  "So, are you ready to hang out tomorrow?"

"Am I ever!" Thunderlane said enthusiastically.  "We're gonna have a whole day of fun, I promise!"

"I can't wait," Blossomforth replied.  "I just hope you're not planning to make me pay for you again."

"Come on, Blossom, what do you take me for?" Thunderlane said, feigning offence.  "I told you I'd pay you back.  So I'm paying for everything tomorrow.  I'll even buy you dinner."

"Aw, that's so sweet," Blossomforth replied.  "So… see you tomorrow morning then?"

"Totally," Thunderlane agreed.  "Later Blossom."

"Bye," Blossomforth called as she and Thunderlane trotted in opposite directions.

Cloudcover and his two assistants stood in the shadows, watching their target disappear down another cloudy causeway.

"Um… are we too late?" Pipsqueak asked hesitantly.  "It kind of sounds like those two are going on a date tomorrow."

"Yes, it would seem our client has waited a little too long," Cloudcover agreed as he removed the ridiculous glasses Scootaloo had insisted he wear.  "It's regrettable, but we should probably just go tell Cloudchaser to give up on this one."

"What?  Give up?  Already?!" Scootaloo cried suddenly.  "I thought you shipping ponies were tougher than that!"

"But Scootaloo, you heard that conversation," Cloudcover sighed.  "Don't you think it would be a bit strange to set Cloudchaser up with a pony who has a date with a different mare tomorrow?"

"Do you know it's a date?  I didn't hear the word date!" Scootaloo insisted.  "I know I said you shipping ponies have kind of a lame job, but it's even lamer if you don't at least try to fulfill your client's request!  If there's one thing Rainbow Dash has taught me, it's that you should never give up, no matter how bad the outlook is!"

Cloudcover stepped back, a bit shocked by the filly's fortitude.  For a moment, he was unable to reply.

"Maybe Scoot's got a point," Pipsqueak added.  "We don't know for sure that Thunderlane wouldn't even consider it.  We could try, at least."

Cloudcover laughed softly.  "Well… alright," he agreed.  "I suppose we are giving up too easily here.  Cloudchaser is willing to go for it, so we should be too.  Let's go leave an anonymous note for Thunderlane; that should get him to show up for a date with Cloudchaser tonight.  Then we'll just have to leave things to fate; if he's already together with Blossomforth, then it will become apparent when he arrives."

He sighed, despite the grins of approval from Pipsqueak and Scootaloo.  "I just hope this isn't going to be completely pointless," he added.  "I wonder if Flitter and the other fillies are doing a good job down there."

Cloudcover turned around and began to trot back toward the edge of Cloudsdale.

"Hey Scootaloo?"

"Yeah Pipsqueak?"

"Can I keep these sunglasses?"


"Is it too late to change my mind about all this?" Cloudchaser asked weakly.

"Yes," said Flitter, smiling devilishly.  "I have been waiting a long time for a chance to make you look less ridiculous.  I'm not letting you get away from me this time!"

Cloudchaser rolled her eyes.  "Glad to hear you approve of my fashion sense, sis…" she grumbled sarcastically.

She shifted uncomfortably, but was unable to make any move to escape; Flitter had anticipated her sister having second thoughts about the situation, and decided the best way to deal with that was to simply tie her to a chair.  

In retrospect, it was probably a smart move on Flitter's part, Cloudchaser realized.  If I wasn't bound, I definitely wouldn't still be here.

"Relax, Miss Cloudchaser," Applebloom said absently as she unrolled some ribbon.  "It ain't gonna be all that bad.  We're just gonna make a couple of changes to your mane and tail to make you look a little more respectable-like.  And Sweetie Belle's sister is a fashion designer, so she's prob'ly got an eye for that sort of thing.  I bet she can pick out somethin' lyin' around here that'll look great on you!"

"Um, Applebloom?" Sweetie Belle cut in.  "Rarity hardly ever lets me even get near most of her fashion supplies, remember?"

"Well, let's get started," Applebloom said, ignoring Sweetie Belle's argument entirely.  "Now, where's those scissors?"

"Wait, you're going to be actually cutting my mane?"  Cloudchaser asked, clearly panicked.

"Naw, I'm not that confident," Applebloom replied.  "I jus' need the scissors for this here stubborn ribbon."

The filly yanked on the colorful strand a few more times before Sweetie Belle finally managed to locate the scissors.

Cloudchaser's view of the fillies' antics was suddenly obscured as Flitter applied a wet bit of cloth to her face.

"Hey!  What're you doing?"

"Hold still," Flitter said crossly.  "I'm just trying to get that dark makeup around your eyes off of you.  Now stop squirming or it's gonna smear."

Cloudchaser snorted and sat still, trying not to fidget as she felt Applebloom tying some part of her mane with the now neatly cut ribbon.

"Sweetie Belle," Flitter began.  "My closet's in the next room.  Why don't you see if you can find something nice for Cloudchaser to wear?"

"Well… okay" said Sweetie hesitantly as she trotted into the next room.  She opened Flitter's closet and stared up at the array of dresses.

Okay… Sweetie thought, tapping a hoof against her chin.  I need to think like Rarity here.  If I was making a dress for a pony like Cloudchaser, what would I want it to look like?

Sweetie Belle scanned the rack, her eyes eventually settling on a simple, pale yellow outfit.  It was not particularly frilly, but then again, she assumed Cloudchaser would probably not appreciate something too elaborate anyway.  Hoping she'd seen enough of her older sister's work to trust her own judgment, she grabbed the dress and scurried back to Cloudchaser's room.

"Oh, that's perfect!" Flitter squealed as soon as Sweetie entered.  "Here, let's put it on her."

Cloudchaser was finally released from the chair.  She just sighed as her sister forced the dress over her head.

"There!" Flitter announced, standing back and admiring her handiwork.  "Look in the mirror.  What do you think?"

Cloudchaser turned around and glanced into the mirror.  For a moment, she wasn't even sure it was her own reflection staring back at her.  Her spiky mane had been carefully groomed so that the usually unruly bangs now formed a nicely rounded style.  The spikes on top had been flattened down as well, and the back straightened.  Even her tail had been groomed; it looked longer and silkier than she had remembered it, and the ribbon Applebloom had tied near the tip caused it to curl up at the end.

The dress fit nicely, and the removal of her heavily applied eyeliner had indeed softened her usually harsh appearance.  Cloudchaser tried, but she couldn't quite bring herself to hate the new look.  It was definitely different then her usual appearance, sure, but she felt strangely attractive nonetheless.

"This… this isn't bad…" she mumbled, wincing slightly at her sister's resulting arrogant grin.  "You think Thunderlane will like it?"

Flitter scoffed.  "Sis, I think you'd be hard-pressed to find a stallion that wouldn't like it."

The sound of several sets of hooves approached, signaling the return of Cloudcover.

"Okay, ladies," he said as he trotted into the bedroom.  "We've set up a blind date for Cloudchaser and Thunderlane tonight at the… dear Celestia, you look different."

Cloudchaser nodded.  "Yeah, thanks for noticing," she said curtly.  

Cloudcover blushed.  "I… perhaps that came out rather disrespectfully," he stammered.  "You look great.  Your sister did a fine job."

Flitter giggled.  "Aww, thanks!" she chirped.  "But the girls were a big help too."

"Yes, you're all good at feeling awesome about yourselves," Cloudchaser deadpanned.  "Now what was that about Thunderlane?"

Cloudcover collected himself.  "Yes, um… we slipped Thunderlane an anonymous note.  He's expecting to meet a date tonight at that trendy place in town called The Corral.  But you should be aware that we overheard him speaking with Blossomforth, and it sounds like the two of them may already be in a relationship."

Cloudchaser sighed.  "I thought something like that might have happened," she admitted.  "Maybe it is too late."

"Don't worry, sis!  He'll forget all about Blossom once he sees you!" Flitter said.  "Come on, let's go!  And don't worry, we'll be right behind you!"


"This is really uncomfortable…" Sweetie Belle remarked.

"Shh," Applebloom said.  "I know it's a bit cramped, but we have to deal with it if we want to keep an eye on Miss Cloudchaser!"

Cloudcover, Applebloom, Sweetie Belle, Scootaloo, Pipsqueak, and Flitter were all crammed into a small booth in the back corner of The Corral, where they could discreetly watch Cloudchaser's date.  Unfortunately, the tiny booths were not meant for quite so many ponies.  Cloudcover shifted uneasily as Flitter's flank brushed against his.

"So now what do we do, uncle Cloudcover?" Pipsqueak asked quietly.

"Nothing, really," Cloudcover replied, glad for some actual conversation to lighten the awkwardness.  "We've done our part.  Now we have to wait and see if Cloudchaser's date is successful."

He stared across the restaurant, where Cloudchaser sat nervously at another table, waiting.  After a few moments, Thunderlane entered the restaurant, and looked toward the table indicated on the note he had received.  He raised his eyebrows in surprise.

"This is it," Cloudcover whispered.  "Let's see what he says to her."

Thunderlane approached the table as if in a trance.  The two ponies stared at one another for a few rather awkward seconds.

"Hi," Cloudchaser finally managed.

"Hey Cloudchaser," Thunderlane said.  "So… you're my dinner guest?"

"Yeah," the mare responded.  "I mean, if that's cool with you…"

"It's cool," said Thunderlane, sitting down.  "I just thought… I mean, it was kind of a surprise, that's all."

From their vantage point, Cloudcover and the others were unable to hear most of what was said, but judging by appearances, the date did not appear to become any more comfortable with time.  Cloudchaser appeared to be attempting to start a conversation again and again, but each time, Thunderlane's curt answer would instantly settle the matter, and the pair would decline into silence once again.

"This isn't going well at all, is it?" Flitter whispered.

"I don't think so," Cloudcover replied.  "But then again, if Thunderlane is actually dating Blossomforth, having dinner with another mare he knows must be at least somewhat awkward for him."

"I guess it really is true," Flitter said wearily.  "I thought maybe he and Blossomforth weren't actually together yet, but judging by how he's acting…"

Flitter quieted suddenly as Cloudchaser and Thunderlane, having finished their meal, stood up.

"Well, uh… thanks for the meal," said Thunderlane, plastering a fake smile across his snout.  "We'll have to do it again sometime."

Cloudchaser stared at her date for a few moments, and then shook her head.  "Nah, forget it," she said.  "I can tell you had a lousy time anyway."

"I didn't have a lousy time!" said Thunderlane defensively.  "Dinner was great.  Really!"

Cloudchaser laughed darkly.  "Nice try.  You spent the whole meal trying to end the conversation.  You're desperate to get away from me.  So go ahead."

Thunderlane shook his head.  "No, it's not like that!  I was just a little distracted."

"By what?"

Cloudchaser mentally prepared herself for the moment when Thunderlane spilled the beans and admitted to his relationship with Blossomforth.  Surprisingly, he said something totally different.

"I've known you for a long time, Cloudchaser," he continued, "…so, no offence, but I was kind of surprised to see you in public looking, uh… well, like that."

Cloudchaser's mouth dangled open slightly.  "Wait, so… does that mean you like it, or…"

"It looks great," said Thunderlane quickly.  "It's just, y'know, I'm more used to seeing you looking a little… tougher, I guess.  It suits you better."

Cloudchaser's eyes widened.  "I uh… I gotta agree with you there," she admitted.  "I just kind of thought you were more into the girly look, so I got dressed up a little."

Thunderlane raised an eyebrow.  "Where'd you get that idea?" he asked incredulously.

Cloudchaser bit her lip.  "Well uh… I heard some stuff about Blossomforth, and-"

"Blossomforth?" Thunderlane asked.  "What's she got to do with anything?  Just because we're cousins doesn't mean we have to have the same ideas on style."

Cloudchaser gasped.  "W-wait.  Blossomforth's your cousin?"

Thunderlane nodded.  "Yeah," he admitted.  "Since she moved into the area, she's been hanging with me since she doesn't know a whole lot of other pegasi yet.  She's pretty cool though; the two of us are going to the amusement park tomorrow."

He frowned.  "Although, I gotta pay for both our admissions, since I forgot to bring any money the last time the two of us went anywhere."

His expression brightened.  "Say, since you thought this dinner was kind of a bust, maybe you could come along too to make up for it?  , and Blossom totally wouldn't mind the extra company."

Cloudchaser actively worked to prevent the huge, dopey smile that was attempting to spread across her face.  "Sure, sounds like fun," she replied, managing to retain a calm tone of voice.

"Awesome," Thunderlane said.  "You and I can hang out for real, then."

His smile shrank for a moment.  "You, uh… you are ditching the new look, right?" he asked.

Cloudchaser responded by tearing the ribbon out of her hair and shaking her mane until it resembled its original state.  "Better?" she asked.

"Better," Thunderlane agreed.  "See ya tomorrow, Cloudchaser."

"Bye," she called after the stallion as he trotted out the door.

A few seconds of silence followed, and then the sound of several sets of hooves approached.  Cloudchaser turned around and came nose to nose with her beaming sister.

"See?" Flitter said.  "I told you this was a good idea!  If you hadn't gone and tried something, you would still think Blossomforth was Thunderlane's marefriend, when really, she was just his cousin!"

"I have to admit, I hadn't expected that outcome," Cloudcover added.  "But I suppose this means the assignment was successful after all."

The Cutie Mark Crusaders all gasped at the word 'success' and quickly checked their flanks.  Alas, there were still no cutie marks to be found, but at this point, they were hardly deterred by that result.

The seven ponies exited the restaurant, trotting out into the late afternoon sunlight.  Cloudchaser hesitated before turning to Cloudcover and the foals.

"I… want to apologize for being such a jerk," she said.  "I haven't been very cooperative, but if you guys hadn't persisted, I never would have gotten a first date with Thunderlane, let alone a second one tomorrow."

"Think nothing of it," Cloudcover insisted.  "As always, I'm glad I could help, and I think the kids were just as thrilled to be a part of it."

"Yeah, I guess," said Scootaloo.  "I still think this whole business isn't for me though."

"Me neither," Sweetie Belle added.  "It's too stressful."

"That makes three of us," Applebloom said.  "C'mon girls, let's go try something else for our Cutie Marks!"

"YAY!" the other fillies chanted, and together, the three of them took off down the streets of Ponyville.

"Don't worry, uncle Cloudcover," Pipsqueak said.  "I still think you've got the best job ever."

"Thanks, Pip," Cloudcover said.  "You're a bright young kid; maybe you'll grow up to be a shipping pony someday, too."

"Maybe!" Pipqueak agreed.  "But for now, I've got some homework that needs to get finished.  See you later, Uncle Cloudcover!"

Cloudcover watched his nephew disappear, leaving him alone with Flitter and Cloudchaser.

"By the way…" Flitter giggled sauntering up next to Cloudcover, "while we're still on the topic of shipping, I can't help but wonder… are you doing anything tomorrow, Cloudcover?"

Flitter fluttered her eyelashes flirtatiously.  Cloudcover blushed, and Cloudchaser just groaned disbelivingly.

"Really, sis?"  Cloudchaser remarked.  "You're hopeless sometimes."

Flitter stuck her tongue out at her sister.  "Hey, at least I can be direct when somepony catches my fancy!" she argued.  "If you could do that, we wouldn't have had to go through all this trouble."

Cloudchaser snorted.  "Whatever.  Go ahead and flirt then," she grumbled.

Flitter ignored her, instead turning back to Cloudcover.  Her flank bumped into his again, and this time, he was quite sure it was intentional.

"Well?" she asked him.

Cloudcover chuckled.  "You know what?  Why not?  I'm not doing anything tomorrow."

"Great, see you then," Flitter said with a laugh, before turning and flying off with her sister.   Cloudcover watched them for a moment before taking off himself.  Candyfloss would be expecting a report on the new couple, but he'd probably be delighted to hear about this little development as well.

Cloudcover flew in the opposite direction, listening to the barely audible conversation between the two sisters.

"There, now see how easy that is, Cloudchaser?"

"Shut up, sis."
Cloudcover's Bonus Chapter

This is what happens when I try to write a bonus chapter about a one-dimensional OC.

This is pretty much unquestionably my least favorite chapter in S&H. Hopefully you guys get at least a little enjoyment out of it though.

MLP and all related everything (c) Hasbro
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zapemaster Featured By Owner Aug 13, 2012  Hobbyist
ljol3 Featured By Owner Aug 12, 2012
This was your least favorite chapter? I liked it better than the candy floss chapter and the imagination land one.
Okay, that's fine with me. I'm glad there are different opinions on which chapters are the better ones.

I just found this one dull, no matter what I did to try to spice it up, but I guess others enjoyed it more.
ljol3 Featured By Owner Aug 12, 2012
block1431 Featured By Owner Aug 11, 2012
Flitter blinked in surprise. "Huh? You're name's Cloud…cover?"

Not to be a grammar Nazi or a nooblord, but shouldn't in be 'your'? Or maybe you meant 'You're Cloud...cover?,' but added in a bit extra? Whatever it was, I loved this bonus chapter, so have a muffin :3.
That is a typo, and I thank you for pointing it out.

Glad you enjoyed it!
block1431 Featured By Owner Aug 14, 2012
You're welcome.
LottaPotatoSalad Featured By Owner Aug 11, 2012  Hobbyist Digital Artist
Another amazing chapter! Flitter is hilarious!
pj202718 Featured By Owner Aug 10, 2012
Ah, well. He works better as a foil anyway.
EmperorJewel Featured By Owner Aug 10, 2012
Random question, due to me forgetting lots of things. Did Ditzy end up dating anypony from the compony? I thought it was a pegasus called Cloud Kicker, but I suspect he doesn't exist.
Ditzy ended up with her coworker Breeze at the end of the story.

Cloud Kicker is a background character from the show who was not featured in Shipping and Handling.
EmperorJewel Featured By Owner Aug 10, 2012
Ah! I knew there was somepony, I just couldn't remember who. Thank you very much!
Flutterknight Featured By Owner Aug 10, 2012  Hobbyist Digital Artist
Another fine chapter! ^_^

(Even if you don't like it yourself. =P)
Well, it's... decent.
It's more that I don't like Cloudcover. I really failed in making him into a well characterized element of the original story.
Flutterknight Featured By Owner Aug 10, 2012  Hobbyist Digital Artist
True, he didn't exactly get a lot of pagetime (wordtime? I dunno) in the original story like the other characters, but I think he works fine. ^_^
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