The train clattered down the tracks toward the town of Ponyville. Sat in one of the seats was Jackboot, and with him were his cousin, Sophisticata and her coltfriend, Perfect Pace. Actually, he was with them. The couple was on their way to Ponyville for the Summer Sun Celebration that was set to take place there. Jackboot’s reasoning for tagging along with them was that the day before, he had come to a shocking realization that, according to a book on Predictions and Prophecies, more specifically about a story called “The Mare in the Moon”, for told that Nightmare Moon would return on the longest day of the thousandth year. He had voiced his concern to the Princess herself, but only gotten a response saying that it was merely a story.

As a result, Jackboot decided to take matters into his own hooves and was on his way to Ponyville to, in any way possible, prevent what was bound to happen, or in the very least to see what will happen. But that wasn’t his only goal in Ponyville as he had to deliver some packages to a mare named Rarity, due that her packages had arrived at his mother’s boutique by mistake.

The train finally came to a screeching halt at the train station.

“Ponyville!” The conductor shouted. “All out for Ponyville!”

Had Jackboot had not have been restrained as he was, he would’ve knocked several ponies out of the way. But thankfully he didn’t, but casually used his magic to levitate the four boxes along with his suitcase. He was dressed differently as he was wearing a brown suit jacket with the chain of his pocket watch visible, white shirt with cuffs with black buttons, a red bow tie, and a straw boater hat with a red and black ribbon.

“Such a lovely town!” Sophisticata said. “Where’d you say the Inn was again?”

“I think it is several blocks down to the right.” Perfect Pace explained, carrying their suitcase on his back. “Then we’ll just need to keep an eye out for a sign that says ‘Soft Pillow’s Bed and Breakfast’.”

“Sounds good.” Jack said. “After we get signed in I’ll drop these boxes off.”

Suddenly Jack’s suitcase was surrounded in a pale green aura and was taken from him. He looked and saw that it was Sophie.

“We’ll take care of your suitcase, Jack.” Sophie said. “You go on ahead.”

“Seriously?”

The couple nodded.

“We’ll just go around and see the sights and meet up at Town Hall around say, two o’ clock.” Perfect explained. “And then we’ll go over to this place he heard about called, ‘Sugercube Corner’ for lunch.”

The two parties then agreed and went their separate ways. Jackboot made his way down one street away from the train station. He looked around as he trotted down the street, until he finally came to a stop and look around.

“Where is the Carousel Boutique?”

“I worry about him sometimes.”

Sophie and Perfect were now in their room at the Bed and Breakfast. Fortunately, the two had their own room while Jack had one of his own. While unpacking and sorting their clothes, Sophie couldn’t help but think about her cousin.

“What’s there to worry about?” Perfect asked as he shut the dresser drawer. “He’s grown stallion who has a formal education, a well-paying job, and has the determination to complete tasks given to him. He seems to be doing well. If you ask me, there isn’t really any problem.”

“I know that much.” Sophie said as she approached the door. “Come on, we’ll talk on the way out.” Perfect then followed his marefriend out of the room, locking the door behind him. “Where was I? Oh right, anyway, that isn’t what I’m worried about.”

“Then what is it?” Prefect asked as the two made their way down the hall toward the front entrance.

“It’s his social skills I have an issue with.”

“I see.” Perfect nodded. “But doesn’t he talk to ponies every day at work?”

“Yes, but that’s not what I’m talking about.” Sophie said. “He’s pretty much required to talk to ponies when it comes to his job. I’m referring to when he isn’t working. He’s either at the library or at the park by himself with his muzzle in a book.”

“Reading is good, isn’t it?” Perfect asked as the two stepped out into the sunlight. “But, I do understand your concern. But don’t think you might be worrying a little too much?”

Sophie stopped, causing Perfect to do the same.

“I know.” She said with a sigh. “With having gone to school with him before he got into Celestia’s School, you’d know why I’m so concerned.”

Perfect put a hoof on Sophie’s shoulder.

“Worrying about it isn’t going to solve it.” He said. “Besides, this whole Nightmare Moon thing might actually help him out. Why do think your Aunt encouraged him?”

Sophie smiled.

“You’re right.” She said. “And those packages that my Aunt received might help as well. As far as we know, meeting this Rarity mare might help.”

“That’s the mare I know!” He said. He then kissed her on the cheek. “Now come on, let’s go and see what this fine little town has to offer.”

“Alright, maybe I should have gotten a map.”

Jackboot trotted through the streets of Ponyville, caring the four packages. It had been almost half an hour since he parted with Sophie and Perfect and he had yet to have found the Carousel Boutique. Right now he contemplated doing something he had tried to avoid: Asking for directions.

“Maybe I could ask somepony for help.” He said as he looked around at ponies that were trotting here and there. “”But I don’t want to bother them.” He then looked at the packages. “But I do need to get packages delivered.”

He looked around again and caught sight of two mares. One was a light green unicorn with a lyre for her cutie mark, while the other was a beige earth pony with three wrapped candies as her cutie mark. Jack thought they were rather pretty, but that was not important.

“I have to ask somepony.” He thought with a shrug. “Might as well be them.”

He trotted toward the mares.

“Excuse me, ladies.”

The two mares looked over and smiled.

“Hi, there.” The earth pony said. “Can we help you?”

“Yes, I was wondering…”

Before he could fully answer the earth pony, the unicorn let out a gasp, catching Jackboot off guard.

“Jackboot?” She asked. “Jackboot, is it really you?”

Jackboot cocked an eyebrow.

“I’m sorry, have we met?” He asked.

“It’s me, Lyra!” The unicorn said joyfully. “Remember, from Celestia’s school?”

Jackboot thought for a moment until it clicked.

“Okay, now I remember you now.” He said as he set the packages down. “You’re that mare who kept talking about those human…”

Lyra then interrupted the stallion by pulling him into a hug, catching him off guard. He then returned the hug before the two parted.

“So how have you been?” Lyra asked. “I haven’t seen you since we graduated!”

“I’ve been working at father’s metal shop.” Jackboot explained. “How have you been?”

“I’ve been doing alright.” Lyra said. She then looked over at her companion. “Oh, where are my manners?” He then put a front leg over the earth pony and pulled her close. “This is my best friend, Bon Bon.”

Bon Bon then extended a leg, of which Jackboot shook.

“Nice to meet you, miss.” He said.

“You too, Jackboot.” Bon Bon said. “What brings you to Ponyville? Are you here for the Summer Sun Celebration?”

Jackboot was about to answer but noticed the packages.

“Well, yes.” He then levitated the packages. “And I am here to deliver these packages. They accidently came to my mother’s boutique by accident. Do you know where I can find a mare named Rarity and where her business is located?”

“Yeah, follow us.” The Lyra said, waving for the stallion to follow.

Jackboot followed the two mares through the streets of Ponyville, which were busy with activity.

“So, Jackboot. I was hoping I would see you yesterday at Moondancer’s birthday party.” Lyra said as the three trotted. “Were you busy?”

“I was helping my father with a large order yesterday, so I couldn’t go.” Jackboot said. “I did mail her my gift ahead of time. Did she receive it? It was a typewriter I restored.”

“Yeah, she told me she loved it.” Lyra said. “She wished she could have thanked you herself.”

“Well, I’m just glad she likes it.” Jackboot said as he looked around. “I…”

“Here we are!” Lyra said. “Carousel Boutique!”

Jackboot looked and saw that they had arrived at a rather festive looking building. It was tall and had the appearance of a carousel, which made the name a tad obvious but also gave the business some identity.

“I thank you two for showing me the way.” He said.

“It’s no problem.” Bon Bon said. “Will you be there when Celestia raises the sun?”

“I will, yes.” Jackboot answer. He would have told them about Nightmare Moon’s possible return, but it was unlikely that they would believe him.

“Then we’ll see you then.” Lyra said before pulling Jackboot into another hug. “Again, it’s great seeing you again!”

“And you as well.”

Lyra then let go and left with Bon Bon.

Jackboot then turned to the building in front of him.

“Alright, let’s get these packages delivered.”

Jackboot opened the door and entered the shop, welcomed by the frilly interior.

“Hello?” He said. “Is somepony here?”

“Coming!” Somepony answered from another room.

Jackboot heard hoof steps coming from the stairs, assuming that this pony is Rarity, the mare he heard so much about. Upon seeing who came down the stairs, it seemed that for Jackboot, time slowed to a complete halt as her hooves made contact with the floor. Time may have stopped, but Jackboot’s heart didn’t get the message. At this point, one wouldn’t need a stethoscope to see how high his heart rate was as he saw the pony’s perfectly styled, indigo mane bounced as the mare strode across the floor.

“Welcome to Carousel Boutique.” She said as she approached. “How can I help…?” The mare then gasped. “Oh my Celestia!”

She then trotted toward Jackboot. Suddenly time fast forwarded.

“I absolutely love your outfit!” She said as she looked up and down the stallion with the twin sapphires that were her eyes that glistened in the light. “I must know who designed it. Can you give be the ponies name?”

Jackboot didn’t know what to say at this point. The most beautiful mare he’s ever seen, with a voice that rivaled the best musicians in the kingdom, was a foot away from his face.

Suddenly, the mare produced a look of concern.

“Are you alright?”

Finally Jackboot snapped out of it.

“Oh, yes!” Jackboot said, unintentionally answering loudly. “I’m sorry, what were you asking?”

“I was asking who designed your outfit. It’s absolutely lovely!”

Seeing that mares smile made Jackboot almost melt. But he didn’t want to melt just yet, as he had to answer her question.

“Actually, I designed them.” He finally answered.

The mare’s eyes almost popped out of her head upon hearing his answer.

“You made them?”

“Yes, ma’am.” Jackboot said. “Even the hat.”

“That’s incredible.” She said. “I must say, you and I will get along perfectly.”

She then stuck her hoof out.

“I’m Rarity.”

Jackboot shook her hoof as gently as he could.

“Jackboot.” He said. “It’s nice to meet you ma’am.”

Rarity’s smile almost made Jackboot melt yet again. This was the mare that he was looking for and now, looking at her, he might as well be delivering packages to a Princess of a foreign land.

Oh right, the packages.

“I also have these packages for you.” Jackboot said as he brought Rarity’s attention to them. “They accidently arrived at my mother’s boutique so I brought them here.”

“That is very kind of you, darling.”

Darling. That word alone made Jackboot’s heart go further into overdrive as Rarity took hold of the packages.

“Oh good, it’s the ribbon I ordered!” Rarity said after opening one of the packages. “Thank you again for bringing this to me.”

“What is all the ribbon for, exactly?” Jackboot asked.

“I am using it to decorate town hall for the Celebration.” Rarity explained. “By the way, where is your mother’s boutique?”

“It is in Canterlot.” Jackboot answered. “It…”

Rarity let a loud gasp.

“You’re from Canterlot?!” She asked. “I am absolutely envious of you! The glamour, the sophistication, it has been my dream to live there!”

Jackboot’s heart rate slowed down as he mentally face hoofed.

“Oh no, she’s one of those ponies!” He thought as Rarity went on about Canterlot. “She’s in for a big surprise when she somehow finds her way there.”

“You and I will most certainly get along.” Rarity said gleefully. “Now tell me, what’s it like living in such a place?”

Jackboot thought that he was the last pony to ask about Canterlot life. A quiet, metal-pounding, shut in and she was asking him? He needed a way out and then saw the boxes of ribbon.

“Don’t you think you should get that ribbon set up?” He asked. “You know, so you’re not late for the Celebration?”

Rarity thought for a moment.

“You’re right.” She said as she took hold one of the packages. “And again, I thank you so much, darling. I hope to see you again.”

Just before Rarity could make her way toward the door, a thought came to Jackboot’s mind.

“That might take a while to decorate town hall.” He thought. “She may be naïve about living the upper-class life. But that doesn’t mean she doesn’t deserve help.”

He then made up his mind.

“Excuse me, Miss Rarity?”

“For a country town it’s bigger on the inside than on the outside.”

Sophie and Perfect trotted their way down the street.

“You can say that again.” Perfect said, agreeing with his marefriend. “It feels like we’ve been through this street already.”

As the pair walked, they spotted a pony walking that looked rather familiar. She was a light purple unicorn with a purple mane and tail with a pink and dark purple line through them. She was a followed by, to their surprise, a small purple and green dragon carrying a piece of paper.

Sophie recognized her immediately.

“Twilight!” She called over as she waved her hoof frantically. “Twilight Sparkle, over here!”

The unicorn looked over and saw Sophie waving and approached with the dragon in toe.

“Hi, Sophie.” Twilight said. “I haven’t seen you in a… …whoa!”

Twilight then found herself in a tight hug from the brown maned mare.

“Sophie, it’s good to see you too but could you not squeeze me so tight?” She groaned. “I ate a little too much earlier.”

“Oh, sorry.”

Sophie then let go of the purple mare. She then spotted the dragon bringing up the rear.

“And is that Spike?”

She then approached the small dragon and hugged him.

“How have you been, little guy?’

“I’ve been doing well.” Spike said. “Just following Twilight around again.”

Twilight rolled her eyes.

“So Twilight, what brings you and Spike here to Ponyville?” Perfect Pace asked. “Did you come for the Summer Sun Celebration as well?”

“We did.” Twilight answered. “We were sent by Celestia to make sure the preparations were in order.”

“We just gotten done making sure the food is ready.” Spike said. “Right now we’re looking for a pegasus named Rainbow Dash. She’s supposed to be clearing out the clouds right now.”

Everypony looked up at the sky and saw that there were clouds still left in the sky.

“It appears she is slacking off.” Sophie said. “You would think that somepony with ‘Dash’ in their name would get the job done rather…”

“Watch out!”

Perfect lunged and practically tackled his marefriend as a light blue blur zoomed past, missing everypony a few feet.

“What was that?” Twilight asked after dodging out of the way. “And where did Spike go?”

The three ponies looked and saw that Spike had fallen in a large mud puddle. With him was a light blue pegasus with a rainbow colored mane. The winged mare looked down at Spike.

“Uh, excuse me?” She said with an awkward chuckle, knowing full well she was at fault. “Hold on let me help you.” The mare then flew away and returned with a dark cloud. She got on top of the cloud and proceeded to jump on it, causing rain to fall from the bottom. She looked down at Spike saw that the mud had indeed come off, but he was now soaked. “Oops. I guess I over did it, I know!” She then kicked the cloud away and proceeded zoom around Spike. “My very own, Rainbow Dry!” She shouted as she created a whirlwind around the dragon. She then stopped, causing the whirlwind to disappear, leaving behind a now dry dragon.

“Hey, thanks!” Spike said.

“I assume you’re Rainbow Dash?” Twilight asked.

“The one and only!” The blue mare said as she landed. “Why? You heard about me?”

“Yes I have.” Twilight said. “I’m Twilight Sparkle and the Princess sent for me to check on the weather. But from what I’ve seen, you seem to be slacking.”

“Oh please, slacking?” Rainbow Dash asked. “Don’t’ worry, I’ll get it done. Just after I’m finished practicing.”

“What are you practicing for?” Sophie asked.

“The Wonderbolts!” Rainbow said, pointing at a post on a wall. “They’re going to be here for the Celebration tomorrow, and I’m going to show them what I got!”

“The Wonderbolts?” Twilight asked. “I’m pretty sure that they won’t take somepony who isn’t able to keep the sky clear for a day.”

Rainbow Dash produced a look of offense.

“Are you kidding me?” She asked. “I can clear the in ten seconds flat. Just watch!”

Rainbow Dash then flew into the sky and proceeded to kick each cloud in the sky in what felt like the time she had claimed to achieve.

“What did you think of that?”

Perfect looked over at the clock tower in the distance and saw that barely any time had passed.

“It appears you are a mare of your word, Miss Dash.”

“I ain’t going to let Ponyville hanging!” Rainbow said before looking at Twilight, seeing that her jaw had dropped. She let out a laugh. “You should see the look on your face!” She said before letting out another laugh. “You’re a laugh, Twilight. We should hang out sometime!”

The rainbow maned pegasus then flew away.

“Well she was certainly, friendly.” Perfect said. “What do you think, Sophie?”

“I agree.” Sophie said. “And you Twilight?”

Twilight shook her head, causing her focus to return.

“She knows how to do her job.” She said. “Anyway, it was nice to talking to you two again. Right now Spike and I need to get to Town Hall to make sure the decorations are in order.”

“We are actually looking for Town Hall.” Sophie said. “Mind if we tag along?”

Jackboot carefully used his magic positioned a banner above a window on the second floor.

“Is everything alright up there?” Rarity called from the ground floor.

Jackboot trotted over to the railing.

“Almost finished up here, Miss Rarity!” Jackboot said. “I only have two banners left to hang up here.”

Rarity smiled.

“That is good to here!” She said. “Just come down here when you’re finished!”

Jackboot returned to his work. After putting up the last banner, he heard doors to the entrance open, catching his attention, and trotted over to the railing to see who it was. He saw three ponies and a small dragon carrying a list enter. He recognized two of them as his cousin and her coltfriend. The other pony and the dragon really caught his attention.

“Twilight Sparkle?” He thought. “What’s she doing here?”

He then trotted down the stairwell and into the main room. Where she saw Twilight now speaking to Rarity. The latter spotted him as he approached.

“Oh, Jackboot.” She said before returning her attention to Twilight. “This is the stallion that helped me make this possible.”

Twilight looked at the gray stallion.

“Jackboot?” She asked. “I haven’t seen you in a while. How have you been?”

“I’ve been well.” Jackboot answered. “Just piddling.”

“This seems to be a tad more than piddling.” Sophie said. “I see you delivered the packages as promised.”

“Well when given I task I see through its entirety.”

Jackboot then glanced over at Rarity.

“Oh, this is Rarity. The recipient of the packages.” He said. “Miss Rarity, this is my cousin, Sophisticata, and her lover, Perfect Pace.”

Rarity first shook Sophie’s hoof.

“It is nice to meet you.” The former said. “I must say your cousin is a very sweet stallion for bringing me my ribbon himself.”

Sophie smirked at her cousin as he scratched the back of his head while partially looking away.

Rarity then shook Perfect’s hoof, who of which gently kissed hers in return.

“It is nice to make your acquaintance ma’am.” He said. “We would like to stay but we’re going to have lunch. Do you know where we can find a place called, Sugercube Corner?”

“Why, yes.” Rarity said. “You go outside and then you take the right side road and continue until you see a building that looks like it is made of deserts.”

“Okay, thank you.” Perfect said.

Rarity then turned to Jackboot and put his hoof in hers.

“Thank you so much for the help Jackboot.” She said. “I really do appreciate it.”

“It was nothing really.” Jackboot said. “I’m just glad to help.”

“It looks like you’ve been busy.” Sophie said to Jackboot as they looked for Sugercube Corner.

“I was just doing what I was told to do.” Jackboot said. “And she seemed like she needed some help.”

“And help her, you did.” Perfect said. “What was her name again?”

“Rarity.” Jackboot answered.

“She was pretty wasn’t she?” Sophie asked, giving Jackboot a look.

“Yes, she was rather attractive.” Jackboot agreed, hiding how he truly felt.

“I think she might be single.” Sophie said, causing Jackboot to look at her, now knowing what she was getting at.

Before the conversation could continue, a pink blur suddenly landed in front of them out from no where. This blur turned out to be a pink earth pony with a puffy pink mane and bright blue eyes. What’s more is that she had possibly the biggest smile they’ve ever seen on a pony.

“Hi!” She said. “I’ve never seen you here before!”

It took a moment for Perfect to find his voice.

“Uh, yes. We just got here from Canterlot.” He said before clearing his throat. “I am Perfect Pace, and this is my marefriend, Sophisticata, and her cousin her, Jackboot. We are here for the Summer Sun Celebration.”

“It’s nice to meet you!” The pink mare said. “I’m Pinkie Pie! I know everypony here in Ponyville. I was in the middle of inviting everyone to a surprise party for the new pony in town! Do you three want to come?”

The three looked at one another. Sophie had a look in her eyes that said she want to go while Jackboot merely shrugged. Perfect then looked back at the earth pony.

“I don’t see why not.”

Author's Note

Sorry it took so long for this to come out. I've been busy.

By the way, this is what Jackboot looks like:

Either way, I hope you enjoyed!