Skater Boy

by Wiz Ahmad

Rating: teen
Tags: Gilda, Scootaloo, Adventure, Princess Celestia, Alternate Universe, Human, Main 6, Princess Luna, My Little Pony: Friendship is Magic, Comedy, Romance
Length: 8188

While running from bullies, Harry skates down a tunnel and ends up in Equestria.

EDIT: THIS STORY WAS BADLY PRODUCED, HORRIBLY PACED, AND HAS BEEN CANCELLED. IT ISN'T WORTH YOUR TIME. GO READ SOMETHING ELSE. (also, take it as an example of how NOT to write a human in equestria fanfic)

Harry wanted one thing in the world: to become a pro at street skating. But after months of practice, he lands an epic fail while skating with a few pros. A mean gang of rival skaters laughs at him and then takes a step to bully him for failing. In an attempt to escape, he skates down a tunnel and falls into a teleportation pit, ending up in Equestria.

Will he be able to return home? Will he make friends? What will the ponies think of him?

Rated T for language and some romance. My first HiE fic as well so go easy in the comments please.
I KNOW these types of fics are overrated but I wanted to have a shot at making my own.

Published 2016-07-04 00:10:01 UTC
Last updated 2016-07-06 17:31:59 UTC

Down the Tunnel

Author's Note

First chapter! Some parts I may need to rewrite though. Hope you like it!

Down the Tunnel

It was another long great day at the graffiti-lined slopes next to a busy railway line in the industrial depths of San Francisco, with three professional skaters having landed three sequential tre-flips and two 900s.

“You guys are like gods,” Harry remarked as they slapped him high-fives. “I might as well be in the little kids’ department of sorts.”

“Ah, don’t put yourself down, kid,” said Jack, one of the pro street skaters whom Harry admired. “I was even clumsier than you at first. Just keep going and boost that practice time.”

Harry nodded, trying to look confident. And he was – to a degree. Most of his time had been spent indoors playing with his Xbox (until it was stolen). His mother then took it as a sign that he needed to get outside more and keep a reasonable distance from technology at large. Recalling his childhood Harry decided to relive the moments he had as a 5-year old wanting to skateboard and watching gazillions of Tony Hawk and Rodney Mullen videos.

Over time he’d built up some experience and could ollie, kickflip, heelflip, and grind fairly well, in addition to a few other unnamed tricks. Even so, he was nowhere near the skill and precision of the local pros.

Merely getting to this special arena wasn’t easy either. Harry visited this spot only on the weekends, and relied on what little allowance he had to take the bus down to a specific industrial area of San Francisco – his hometown – to play in an abandoned lot which had been converted to a street skating arena.

“Be back by 7:30 sharp!” The stern reminder of Mom rang in Harry’s head as he took up his position amongst the pros to try and see what he was capable of. It was kinda hard with twenty other players watching.

Gulping at the snap of fingers, Harry slid down the ramp and popped a well-formed ollie. Unfortunately, he’d forgotten to take into account the short distance between railings. A misjudged kickflip threw his legs onto the metal rail with a bang, and his body and head hit the concrete ground with a thud.

It was hard for Harry’s body and spirit to choose which brought greater pain – the grazed skin and aching, banged-up, slightly bruised body, or the roar of the mocking hyenas in the background.

“You okay, Harry?” Jack rolled up. He reached down but Harry blocked him. “It’s okay guys. You can go. I’ll be fine, honest.”

Jack’s lips twisted. “You sure?”

He nodded seriously, trying not to show the emotional pain from the humiliation arrows the mean spectator skaters had shot him with. Jack walked away and joined the rest of his group. As they walked to their cars, Harry slowly got up, carefully sliding his legs into position to stand up.

The other skaters stood up as well, and started to approach. It didn’t take a double thought to realize they didn’t have nice intentions in mind.
Not good, Harry thought. Rubbing his left forearm, his hand came back with a red smear. The skaters’ walk had quickened to a brief jog. Thinking fast, Harry glanced around for an escape route and located it – a small tunnel leading under the train tracks near the bottom of a slope adjacent to the far end of the skating arena.

“Sorry to bother you, but I gotta skedaddle,” he told the skaters who’d mocked him for his fail. Easing to his feet, Harry stepped back up onto his board, rode to the top edge, grabbed his small knapsack, and skated down the ramp towards the far end as fast as he could.

“GET HIM!” the other skaters all shouted, and Harry quickened his pace. They all ran after him, easily catching up due to their larger size and greater muscle. But Harry had one advantage – agility. Nearing the end of the skate park, he ollied over the short fence and jumped down into the wet valley below.

Scampering to his feet after a hard landing, Harry threw on his knapsack, picked up his board, and ran into the tunnel – just as the other skaters jumped down into the valley after him.

“Damn, you guys are determined,” Harry said, shaking his head in frustration. Running under the train tracks, he noticed another tunnel leading off to the side.

“Okay,” he thought, glancing back at the hounds on his tail. “If I can’t get out of this one, then I’ll simply turn ‘round and smother them with karma.”

Slowing down, Harry spun to the left, dropped his skateboard onto the ground, and skated into the tunnel, the skater hounds following close behind. His plan seemed less and less reasonable, however, as the tunnel appeared to go on to no end, leading into nothing but pitch blackness. At least the tunnel’s circular shape meant he could go a little faster, whilst his chasers would have it hard running on a rounded surface.

The chase, while a bit one-sided, was now becoming boring, with no ending. All Harry could do was keep going and hope there was something for him at the end – if there was an end, that is.

An answer came sooner than any of them expected, as the wheels of Harry’s skateboard hit a bump, which caused a large metal panel to flip up.

BAM! Harry’s pursuers got hit hard in the face. Harry himself, however, had it worse. All of a sudden, there appeared to be a white light at the end of the tunnel. Instead, just as the light seemed to come within reach, the world beneath him opened up.

Too frightened to even scream, Harry grabbed his skateboard and held it tightly as he fell down, losing all consciousness of the world around him.

A New World

Author's Note

Rewritten slightly for all you critics. If it still ain't right for you then please point me in the direction of someone who can help me in this regard or knows how to write a good HiE fanfic. Because this being my first one, I sure as heck don't. :trixieshiftright:

Thank you. :ajbemused:

A New World

Harry blinked. Twice. Nothing felt realistic anymore. By whatever calculations his painful brain could make, he’d fallen at least four thousand feet. Yet here he lay, still alive and well. But the weirdest thing was that he was still in a tunnel – only this one was a lot shorter and did have a believable exit with actual light coming in from it.

Picking up his achy body, Harry felt more uncertain and distressed than ever, his grazed arm throbbing. “Screw you bloody skin,” he muttered, walking to the exit.

Coming out of the tunnel’s end, Harry found himself in a totally different landscape. In fact, the “tunnel” was more of a cave, and plants of all kinds surrounded it. Scanning the surrounding area, he figured he was now in a forest of sorts, with tall trees, interestingly shaped bushes, and…a trail.

This ain’t San Francisco at all, he instantly realized. I must be lost. But what about my home? My mother, my…

For the next few minutes Harry’s brain was in a total frenzy, as it was overloaded with questions, panic, and uncertainty.

“If there existed such a thing as teleportation via falling into a black pit, then I sure as heck have experienced it,” Harry thought, as he finally chilled out and picked his way through the foliage and started to walk down the trail, hoping it would lead him to a town or house of some sort where he could figure out everything.

If it wasn’t such a serious situation of figuring out where you were, this would be the most relaxing and peaceful walk Harry had had in a long time in his life. The flowers, bushes, and trees, along with the birds, squirrels and rabbits moving about reminded him of Bambi – one of his favorite childhood movies.

After a good fifteen minute-walk, Harry came upon a small stream, and heard the sound of a few animals – chickens, various small birds, rabbits, and even mice. As he continued on the sound became louder and more significant.

“Sounds like a farm,” he thought. “But who in God’s name would have a farm right next to a forest?”

Shrugging, Harry kept walking, slowing his pace due to tiredness. But as he came up a small gradient, the sight of what lay just ahead fascinated him.

A small house – like a round-topped cottage – stood at the forest’s edge, with a fenced-in area next to it. Within the fenced area stood several animals which he’d heard earlier.

“This doesn’t look human-like to me at all,” Harry scoffed. “Am I in a childish dreamland or something?” A hard self-knock to the head proved his theory wrong.

“Okay, dude, you need to stop hurting yourself,” Harry snapped to himself. “You’ve failed on your skate trick, fallen down a pit, and now you’ve almost knocked yourself over doubt of the realism of the present surroundings. Get a grip and figure it out!”

Leaving the trail behind, he walked through field of trees, towards the cottage. Maybe its owner had some answers to all the questions he had, the biggest one which was WHERE AM I?

After a good party at Sugarcube Corner, Fluttershy was looking forward to a nice afternoon picnic with her animal friends.

“There you go, Mr. Mousey,” she said kindly, handing the little mouse some cheese. Soon everyone was eating happily…except for one: Angel Bunny. As usual he was up to his stubborn charades and demanding behavior, and it was up to Fluttershy’s special animal communication capabilities to decipher what he was trying to tell her.

“You’re still hungry?”

Angel Bunny shook his head.

“You want some food from the EverFree Forest?”

Angel Bunny shook his head again, harder this time. To emphasize his point, he jumped over to the window and pointed, poking the glass. Fluttershy finally understood and looked through the window, only to spot a tall, two-legged creature walking out of the forest towards the house.

“Aaaah!” Fluttershy gasped, pulling back from the window and gathering all her animal friend together.

Harry wasn’t sure what to make of the cottage at first. It looked like a quiet, happy, serene place to live – unlike the noisy, cold, claustrophobic place he called home.

Taking note of the dainty little mailbox and the stack of birdhouses, he approached the entrance, and gave a few quiet knocks.

“H-hello?” A soft voice came, and Harry could tell whoever it was, she was shy and anxious. “Anypony there?”

Harry’s eyes widened in surprise. It wasn’t a person who lived here – it was a pony. A pony who was shy and could talk.

“Is that you, Rarity?”

Rarity? Harry wondered, a myriad of questions flooding his mind. Who’s that? So this pony had another friend? How many of them were there? Was it just those two, or was this a whole land dominated by talking ponies?

The door opened and Fluttershy jumped back in shock at the sight of a human at her doorstep.

“Wait!” Harry pleaded, still trying to contain his own shock at the sight of a talking yellow pegasus. “It’s all right. I won’t harm you, I promise.”

Fluttershy carefully crept out from behind the door, and Harry’s patience was really tested.

“Relax,” he whispered. “This is your home, right? You should feel at peace here.”

Fluttershy looked down, then up, shooting him a strange look. “I’ve never seen you before,” she said.

Harry smiled back at her, starstruck by her cuteness and beauty. “I could say the same. May I come in please?”

Fluttershy, now feeling at ease in Harry’s presence, ushered him in. But as she did so, her eyes caught a glimpse of the graze on his arm.

“Omigosh we better get you cleaned up!” she exclaimed, helping him to a couch in the living room.

Harry took off his knapsack and set it down on the cottage’s wooden floor beside his skateboard while Fluttershy ran upstairs. In an instant she was back down with a first aid kit, rubbing alcohol, a pink towel, and a bowl of warm water.

“Thank you very much,” he told Fluttershy as she washed, cleaned, and bandaged his arm. “You’re…very kind. And very beautiful.”

“Oh…thank you,” Fluttershy replied, blushing. “What’s your name by the way?” she asked, putting the final layer of sealant on the bandage.

“Harry. And you?”

“I’m…Fluttershy.”

Harry nodded. The name explained pretty much everything about her behavior the first time they saw each other. But there was one other thing that was nagging his mind.

“When I knocked, you mentioned Rarity. Who’s Rarity?”

“She’s one of my friends,” Fluttershy explained, handing Harry a glass of juice. “She’s a fashionista and a dressmaker – the only one in Ponyville, in fact.”

“Wait a minute.” Harry held up his hand. “So there’s like a whole group of ponies who live in a village near you?”

Fluttershy nodded, before asking a question herself. “You’re a human, right?”

Normally if someone were to ask Harry that question he’d slap them right over the head for asking such a dumb question when it was plainly obvious. But this was a land of ponies, not humans. So he remained calm. “Yes, I am. How did you come across such a term, and how did you know of humans when this is a land of ponies?”

Fluttershy giggled. “One of my friends, who is highly educated and informed of other universes and dimensions read up about them, and passed the info on to me.”

I hope these ponies don’t think badly of me, Harry thought worriedly. As if she scanned his mind, Fluttershy said, “But no worries, we ponies are a friendly bunch. In fact, why don’t I tell my friends to come over for a meet and greet? Sounds good?”

“Yeah…sounds great,” Harry replied, trying not to sound sarcastic. While Fluttershy was calm and collective, the behavior and mannerism of her other friends was still unknown to him.

“Feel free to make yourself comfortable with my animals. I have a sandwich in the kitchen if you’re hungry. See you in a bit!” With that, Fluttershy dashed out the door and ran down the pathway towards Ponyville.

Meeting the Residents

Author's Note

Another chapter. I'm sure it's gonna need some editing at some points. Give me your criticism, I'm braced for it. :ajbemused:
I'll have you know one thing I learned about myself: I'm not good at writing HiE fics :twilightsheepish:

Meeting the Residents

Harry leaned back on the sofa, relaxing to rest his tired and stressed muscles. The sandwich had vanished instantly, as well as a bit more of the juice. To occupy his spare time, he placed a few pieces of cheese on his skateboard and moving the mice around on it when they jumped on to eat the cheese. Thankfully Angel Bunny just ignored him for the most part, and kept to himself in a far corner of the cottage.
The pain of his arm and the aching of his body soon took over and he nodded off to sleep, aided by a singing yellow canary and a couple finches.

His sleep was soon interrupted by the squeak of the door’s hinges. Upon instinct he stretched awake with a groan, rubbed his eyes, and sat up, only to be greeted by not one, not two, but six ponies. They all looked different, each appearing to reflect certain traits or talents within them.

“Hello there, my name’s Twilight Sparkle,” a purple one said in a positive, slightly excited tone. She had straight-cut purple-and-pink bangs, along with large wings and a horn atop her head – a clear blend of an alicorn and a Pegasus. “You must be Harry. Welcome to Equestria.”

Equestria? Ok so that’s where I am, Harry realized. “Thank you, Twilight. So these are your friends, right?”

Twilight nodded.

“Fluttershy, is this guy your coltfriend or something?” Rainbow Dash interrogated rather harshly.

“Oh no, Rainbow Dash, this is someone I met. He came from the EverFree forest,” Fluttershy explained.

Then it was the turn of the pink girl. “Hi! I’m Pinkie Pie! Are you lonely? Do you wanna be friends? How about a party? You want a party?”

“Hold it, hold it!” Harry exclaimed, putting his hand to her lips. “To answer those questions and a bunch more I’m sure you have…well, I guess a party would be nice. Haven’t had one in a while and could definitely do with some good humor to lighten me up after all the crazy crap I’ve been through.”

“Thank you thank you thank you thank you thank you thank you thank you!!!” Pinkie Pie exclaimed and zoomed out of the house in a flash to prepare the party. In spite of this, Harry still looked sad and distraught.

“What’s the issue?” Twilight Sparkle asked.

“I…I’m lost,” Harry admitted. “I don’t know really where I am, how I ended up here, or how I’m going to return home – if that is possible. It is, right?”

Twilight’s face twitched in doubt. “Yes, it might be, actually. Tell me, Harry, how did you end up here?”

Fighting back tears, Harry told them the whole story – how he’d been chased down the tunnel, how he fell down the pit, crawling out of the tunnel, and ending up in the EverFree Forest. He also described what San Francisco looked like, and how it wasn’t anything like Equestria.

“Seems like you’ve ended up in one of those random portals,” Twilight said, nodding slightly. “I’ll need to look into it later. In the meantime, you have us, Harry. We’ll be here for you always no matter what.”

“Thanks a lot,” Harry replied, embracing Twilight in a hug. Her fur felt extremely soft and unique – softer than any fur he’d felt back on Earth. The warmth from her body also made him feel relaxed and content.

“Now for names,” he said, noticing one of them with a cowboy hat on her head, pointing at her. “You look like a cowgirl. Farm worker much?”

“You know it, sugarcube,” Applejack replied. “Name’s Applejack, owner and worker at Sweet Apple Acres, grower of the best apples in Equestria.”

Harry’s eyebrows raised slightly and he licked his lips. “Sounds sweet. I’ll be sure to stop by sometime.” He turned to the one with a curly mane that was combed and brushed to impossible perfection. “You must be Rarity. Fluttershy here has told me about you.”

“Why yes, I am Rarity, Ponyville’s resident seamstress and fashionista. If you need anything textile don’t be afraid to ask me.”

Harry was frozen in awe. Fluttershy was a shy, peaceful girl, but Rarity’s appearance was on another level. Her flowing purple mane, bright expressive eyes, and merry little mouth made her hotter than a match under the summer sun. Rarity sensed this and briefly struck a beauty pose.

“Cut it out, Rarity!” Rainbow Dash snapped, tapping her hard on the flank. “We’re not at Sapphire Shores’s doorstep, you know!”

“Rainbow…” Harry began.

“—Dash,” the blue Pegasus finished.

“Makes sense,” Harry added. “I can tell you’re a girl meant for speed.”

“You can stay at my house if you wish so,” Twilight offered, but Harry shook his head.

“Thanks Twilight, but I prefer to stay here with Fluttershy. It’s a lot quieter and I think I’d feel more relaxed. Besides, I like being distant from the masses.”

Twilight felt a little put off with him declining her kind offer, but accepted his decision. And she could see why – Fluttershy did have a nice home with a calm, almost therapeutic atmosphere to it.

"It's been great knowing you all," Harry thanked them. Then he leaned back on the couch to rest.

“Wait, why you laying back, darling?” Rarity asked. “Don’t you want to see the rest of Ponyville and meet its inhabitants?”

Harry nodded, but explained to them the ordeal he’d been through, and also showed the injury on his arm. “So yes, but just not at the moment. Give it another few hours.”

Twilight and the others agreed, and left, promising to meet him just outside the town in the afternoon. While Harry napped, Fluttershy went about her business, tending to Angel Bunny and helping out a few mice, before heading off to Froggy Bottom Bog to assist a few salamanders in crossing a particularly tricky portion of the bog.

The ringing sound of a kitchen timer snapped Harry out of his doze. With the late afternoon here, it was time for his Ponyville tour. Stretching awake, he washed his face in the bathroom sink and took a brief drink of juice, before picking up his skateboard and heading to the front door.

“Well, if it ain’t you again,” he huffed, glaring at Angel Bunny as he tied up his shoes. “At least we have an agreement of sorts.”

Outside, Fluttershy was patiently waiting, holding a bouquet of exotic flowers she’d picked on her way back.

“How was your sleep, Harry? What’s that?” she asked as Harry set down his board and hopped onto it, gliding down the path.

“It’s called a skateboard,” Harry explained. “I travel around on it and perform tricks with it, too. And why yes, I slept well. Your birds were really helpful in getting me to sleep.”

Right at the pathway into Ponyville, Twilight and the team were all waiting, looking rather surprised to see Fluttershy flying alongside Harry.
“Hi there!” Fluttershy called, waving. “You all ready?”

“Ready as ever!” Rainbow Dash declared, and they all walked into Ponyville, Twilight leading the way.

While the quizzical looks of many of the ponies was more than expected, it still made Harry feel uneasy. Twilight, Fluttershy, and the others, however, were totally unfazed. Rainbow Dash pointed to a tall, circular building at the center of the town. “That’s the town hall.”

"Lovely formally crafted building." Harry then noticed a certain building that looked a little like a gingerbread house. “Is that…”

Pinkie burst out of the building’s front door and came bounding over.

“Hi, Harry! How’s your stay in Ponyville going? The Cakes at Sugarcube Corner just baked some super delicious cupcakes! Do you wanna try some? Do you? Do you?”

Damn girl, you speak as fast as hell, Harry muttered under his breath. “It’s going…well, so far. Cupcakes? Sure!”

So Harry skated down the path towards the bakery, his new friends in tow, while the rest of Ponyville looked on in bewilderment.

“Well, who do we have here?” a sweet voice came from behind the counter, and Harry stuck his hand out in greeting.

“Harry here, a new visitor. Nice to meet you. Great bakery, by the way.”

“Mrs. Cake. Nice meeting you too.” The kind pony stuck out her hoof and exchanged a handshake with Harry.

After a nice chat with Mr. Cake, Harry sat down to eat some of the cupcakes which Pinkie had mentioned earlier, while Rarity asked a brief but thought-provoking question.

“Have you considered that we haven’t informed the rest of Ponyvile formally about Harry, let alone told the Princess?”

Harry’s ears snapped to attention, his mouth still full of creamy frosting and soft sweet cupcake. “Princess? You guys have a ruler here?”

Twilight nodded. “Several, in fact. Two sisters rule over the whole of Equestria at large, and one other rules over the Crystal Empire up north.”

Harry’s heart skipped a beat. “I never really got to travel much, but now that I’m sure, I might make the most of it in due time. I’m a bit nervous about the Princess though – should I just mingle about here in Ponyville, or inform your noble rulers of my presence in your world?”

“I’ll be honest with ya here, Harry, the latter is the wiser decision,” Applejack advised.

In the Castle

Author's Note

A new chapter for Eid!! :pinkiehappy:
I'm gonna keep writing this no matter what you critics throw in my face. *cough* JINX *cough* *cough* :ajbemused:
This fanfic is probably gonna be a not-THAT-good HiE fanfic that will be personal (i.e. for me to read in my free time much later on when I've improved and can look back at all my old stuff). Enjoy this chapter anyways :twilightsmile:

In the Castle

“So how long have you had trains here in Equestria?” Harry asked, sitting down on one of the seats in the second last car of the train heading to Canterlot.

“They’ve been around for almost as long as Equestria itself,” replied Rarity.

“When Equestria was first formed,” Twilight explained, “the engineers and constructors of the (back then) newly formed empire had trouble transporting materials back and forth across long distances to build up a large town that became what is now Canterlot. So they invented the train to help move materials more quickly and in larger amounts.”

“Interesting,” said Harry. “Much like how in the early days of America, we humans invented the same thing – the steam engine – to move silver which me mined tirelessly for. Sad to say that one shiny metal consumed our hearts like the Nightmare, resulting in a lot of violence, battles against native residents, and fights over possession of well-kept land. Much like Appleloosa and the buffalo – only with lots – LOTS – of bloodshed.” Harry sighed sadly, and his face fell.

“That’s pretty sad,” Applejack added. “I never knew the human world was so cruel and conflicting.”

Harry nodded. “Yeah, it is. Thankfully the intensity of it is a lot less than it used to be.”

“Wait a second, darling,” Rarity asked as the train pulled into the station. “How did you get all the info on Nightmare Moon and Appleloosa?”

“Fluttershy’s got some interesting books at her house,” Harry replied with a wink.

Twilight led Harry down the refined streets of Canterlot, advising him not to ride his skateboard this time to avoid catching excessive attention, in addition to potentially dirtying or damaging the city’s “clean and dignified” roads.

“I get into scuffles with the public almost all the time,” Harry scoffed, trudging behind Twilight as they neared the royal castle. “But this is your ponies’ land I gotta respect ya.”

Twilight shot him a pleased smile, satisfied that the human had dignity and respect. Maybe popping over to Celestia’s house for a quick visit wouldn’t be so hard.

“Who is this?!” the palace guards exclaimed. “A…human?”

“You know it,” Harry replied with a mocking wink.

“I’m Twilight Sparkle,” Twilight said politely and clearly. “May we enter please? I have come here to see Princess Celestia, with prior request.”

The guards rubbed their chins, and Harry wore a pouty face to give them the edge. “You all may enter. But keep an eye on that human, and make sure no trouble arises.”

Why would you think that? Harry thought angrily, tempted to flip them off. Damn, I thought you ponies were less judgmental than this.

The castle was surprisingly complex, and whilst Twilight led him to the throne room, Harry used every moment he had to construct a mental map of all the halls and door positions they travelled down or passed by.

As usual, Princess Celestia was in the throne room, waiting for orders. Princess Luna and Cadence were there too. The doors gently swung open and in walked Twilight with Harry, Applejack and Rarity bringing up the rear.

“Princess Celestia!” Twilight Sparkle exclaimed. “It’s good to see you.”

“Twilight Sparkle! My faithful student,” Celestia responded, walking off the throne and embracing Twilight in a comforting hug.

“Damn, teacher and student? More like mother and daughter,” Harry whispered under his breath, but Celestia heard it and instantly turned to face him.

“Ah, Princess Celestia is it? It’s a pleasure to meet you,” Harry said, bowing before her and keeping his voice in a low, respectful tone.

The princess didn’t reply; instead, she walked over and examined him closely, the way a cop would look at a suspect in the interrogation room. Her stare was intense, and Harry had to force himself to observe the stained glass walls to avoid sweating from mere fear. Finally, when he could take it no longer, he shut his eyes, stiffened his legs, and slowed his breath.

“I’ve been told about you by Twilight Sparkle here and Fluttershy,” she then spoke, shattering Harry out of his petrified trance. “You entered the property grounds of Fluttershy without permission. Is that true?”

“Y-y-yes,” Harry stuttered, still recovering from his fearful state. “Um, not exactly. I came upon her house from the EverFree Forest, but of course I couldn’t approach it from the pathway. So I approached from the back, walked around to the front, and knocked respectfully. I never touched anything of her property, unless she said I could do so.”

Princess Celestia stood silent for a few minutes. “I see. So you ended up in our world by falling down a pit and you crawled out of a tunnel…and ended up in the EverFree Forest. You’re also unable to find a way back home. Is that true?”

“Yes, your Highness,” Harry replied, half-bowing. “I am also grateful for the incredible generosity, kindness, courtesy, and friendliness of your student Twilight Sparkle and her friends. I honestly have no idea how I’d fare in this land without them.”

Princess Celestia was amazed at Harry’s respectful behavior, but his overtly anxious deposition still bothered her. He looked like he was about So she looked at him head-on with a calm expression.

“You’re…so beautiful,” Harry whispered, feeling soppy all of a sudden, and he fought back against his love feelings.

Why did you say that to a ruler, you idiot? he angrily thought to himself. But in a sudden turn of action, Celestia stepped right up to him, wrapped her right wing around him, and gave him a loving snuggle. “It’s okay if you love me,” she whispered. “Hug me if you wish.”

“Thanks, Princess,” Harry replied, lovingly throwing his arms around Celestia’s neck and dropping the skateboard in the process. It rolled down the carpet towards the throne.

“Oops,” Harry realized. “Now I’ve got the royal red carpet dirty! What have I done?”

The quizzical looks on Princess Luna and Princess Cadence were absolutely priceless as they stared at the skateboard. Harry released his love grip on Celestia and ran after his skateboard, lifting its dirty well-worn wheels off the red carpet.

“It’s all right,” Celestia said, walking up behind him. “I’ll get it cleaned up later today. Just try to be careful next time, okay?”

My God, Harry thought as he thanked her again. I just met the ruler of Equestria and now she’s acting like a mix of a friend and a mother.

“What’s that?” Princess Cadence inquired, pointing at the skateboard.

Harry looked up and smiled. Never in his life would he imagine that such powerful and regal rulers would look so adorable and inquisitive. Then again, he and his possessions were still strangers in this new world. “Nice to meet you, Princess…”

“—Cadence,” the pink alicorn replied.

“I love that name, it’s adorable,” Harry complimented. He turned to the other alicorn, whose mane and tail looked like a sky full of sparkly stars, and who had a royal necklace with a crescent moon on it.

Harry didn’t have to guess her name twice. “Princess Luna?”

“How did thou guess thy princess of the night name right first time around?” Luna replied in a voice that sounded comforting, yet seemed to have a hint of longing. “Wait a minute…” Harry thought, and it soon clicked. “You used to be Nightmare Moon before you returned to normal.”

But revealing a redeemed criminal’s past in front of everyone else was never a good idea, and so Harry kept his mouth shut on the matter. Instead, he returned to Cadence’s question.

“Princess Cadence, this is a skateboard,” he began, holding it up for her to see from her sitting position on the side of the throne. “You have the deck, which is flat for me to stand on, then you have the trucks, which are fastened securely to opposite ends of the deck. In turn, the wheels are then attached to the trucks. On top of the deck is a black, self-adhesive gritty wrap called grip tape, which gives the skateboard a good, clean top look and more importantly, it ensures my feet don’t slip.”

“I like it,” Princess Luna complimented with an excited look, and Harry had a feeling of what she wanted, so he cut to the response to the question he was positively sure she’d ask next. “I’m sorry, Princess Luna, but you can’t ride it. You’re too heavy – it’ll snap.”

“Oh.” For a princess, the sad look on Luna’s face was undeniably adorable, and it made him jump back to his previous thought that she was alone after her criminal actions. Harry made a mental note to ask Princess Celestia for permission to hang out with her sometime.

“Enjoy your stay in Equestria,” Celestia told Harry as he exited. “And if Twilight isn’t able to send you back, you’re more than welcome to stay here…”

“…with me and Luna,” she added, whispering sneakily. “I’ll get Cadence to pop by now and then if possible.”

Really? Living with the princesses? Harry was so shocked his kness twitched violently.

“I’d be honored,” was all he could reply in a quick whisper back before Twilight turned her head in suspicion.

“Were you privately making out with Celestia?” she snapped.

“N-no!” Harry replied quickly, trying not to blush. “She was just informing me of something…important, that’s all.” A blissful smile appeared on his face, but Applejack and Rarity caught sight of it before he could wipe it off.

“Do you…” Rarity began, a slight smirk playing across her lips.

“Shut it, guys, I’m feeling hungry already,” Harry retorted, attempting to use a sudden change of temperament to quickly switch direction. But his “friends” weren’t giving up.

“You did hug her…” Applejack said suggestively.

“She was the one who embraced me first,” Harry pointed out. “Now can we please leave? My stomach is growling. I don’t wanna sound like a moaning bear amongst all the dignified beauties of Canterlot.”

Skateboard in hand, Harry glowered as Applejack and Rarity whispered and exchanged chuckles all the way to the train station.

A Rare Surprise

Author's Note

Harry gets a rather unpleasant upon checking out his newly made clothing, and helps out Applejack at the farm.

I may go back and elaborate a few parts near the ending, as well as the chapter ending itself.

WARNING: This chapter contains some crossdressing.

A Rare Surprise

After slipping out of his friends’ rather mean and hurtful comments and suspicions about having a crush, the first thing Harry wanted was to visit Sweet Apple Acres and sample some of its delicious apples. But Twilight insisted on getting new clothes for him, even though his current clothing wasn’t even torn and only had minimal wear-down.

“Don’t you want to look presentable when you turn up in front of the Apple Family?” Twilight said, as they approached Carousel Boutique.

“Yes, but what’s the point of new clothes if I’ll be ruining them with all the running, jumping, apple picking, and heel-flipping?” Harry protested.

Twilight laughed. Harry was more concerned with clothing than she’d originally thought. “You may wear them down a little, but they won’t get tattered unless you’re really reckless, and I know you aren’t, right?”

Harry nodded, a serious and confident expression on his face.

“What’s heel-flipping?” Twilight asked.

Harry hopped onto his skateboard, briefly glided down the path, away from the door.

“Where are you—” Twilight began, but stood in awe as Harry approached, jumped off the board and lightly hit it with his heel, causing the board to rotate mid-air. The instant the board turned right side up, Harry aligned his feet and jumped back down on the board – all in a mere moment.

“Wow, that’s amazing,” she breathed. Just then, the door opened, and Rarity stepped out.

“Hello, Twilight,” she said welcomingly. “Harry? You in for some new clothes?”

Even after being in her presence twice before, Harry was still awestruck by the white unicorn’s beauty. “Uh…yes. Gotta get prepped for my day at Sweet Apple Acres.”

“Come in then!” Rarity replied, urging Harry inside.

Harry didn’t even have to say much, as Rarity knew every detail in the book.

“Could you, um, strip so I can get some accurate measurements, please?” she asked him.

Are you crazy? Harry was close to yelling. But he bit his lip and kept a cool composure. “At least I can keep my underwear.”

Behind a curtain, Harry removed his sweater, shirt, cap, and sports trousers. For extra privacy, Rarity took his measurements behind the curtain as well, away from the eyes of her friends.

“There, all done, darling,” Rarity declared happily, pulling back the curtain as Harry pulled on his sweater and adjusted his cap. “So, what do you have in mind, exactly?”

Harry put his hand to his chin and thought for a moment. “I’d go with at least three fresh pairs of underwear – sorry if that was offensive.”

“Oh, no worries,” Rarity replied kindly. “Anything else?”

“A good blanket for the night at Fluttershy’s cottage would be nice, along with three shirts, a secondary pair of strong lightweight pants, and two special articles of clothing.”

“What’s the special clothing?” Twilight asked instantly, eager to find out what Harry had in mind.

“Anything – I repeat, anything – you wish, Rarity, so long as it fits me. Thank you very much, my lady, and I won’t ever forget your generosity and caring nature. How much do I owe you?”

“Absolutely nothing, darling,” Rarity replied with a warm smile. “This is no tailoring business – this is from my heart to yours.”

Harry blushed. He wanted to hug and snuggle Rarity, but held back as she set off to resume her busy work. How could such a charming, fashion-obsessed lady be so thoughtful and so generous as to make her new friend clothes – for free?

“You’ve got to find a place for that heart of yours,” Twilight remarked as she led him back to Fluttershy’s cottage as the day ended.

Harry’s eyes narrowed, and his mind flashbacked to the hug he and Celestia shared earlier in the afternoon. “What’s that supposed to mean? You’re not saying I’m…romantic with any of you, am I?!”

“No! Not really,” Twilight replied, jumping aside slightly, startled by Harry’s sudden offense. “Like you…you always seem to be in awe in us ponies’ presence. Like, every time we come by and be kind, loving, caring, generous and all that with you, you have that dreamy look – a little. A little.”

Harry sighed. How he wished there wasn’t absolute truth to that. “It’s just…I’ve never experienced such emotion and positive, optimistic, and loving behavior and attitude to this extent in my life before. And I must admit…you ponies, you have a certain charm to your natural appearance. Like, your big, loving eyes. I can’t stare at them without my heart melting like butter in a pan. And your colorful hair and soft, fine fur – it’s so soft and comforting to touch.”

“So you are in love with us,” Twilight huffed. “I thought so.”

Harry sighed again. “Not exactly. I just find you ponies…different. I am calmed and enjoy being the presence of creatures and people who are cute, innocent, and loving. I still think about my mother though.”

After a bit more explanation on why he felt the way he did about Rarity and a few other ponies, Harry left Twilight and headed inside Fluttershy’s cottage to sleep on the living room rug amongst her birds.

Harry was up a few hours later, being awaken by the loud chirping noises of the birds. He rubbed his eyes and glanced out the window. It was just a few minutes after daybreak, and Fluttershy was already outside, tending to the chickens and other animals.

“Aaaah, another great day,” he proclaimed, sitting up and washing up in the bathroom.

“And hopefully a step closer for Twilight to find a way to get me back home…” he added sadly, eating up a nice breakfast of soup and eggs Fluttershy had made for him.

“You all ready for a good day on the farm?” Fluttershy asked, re-entering to wash the dishes and sweep the floor, while Harry wiped up the table and fed a few of the birds as common courtesy.

“I sure hope so,” Harry replied hopefully. “Once the clothes that Rarity’s made for me fit and look well, I should glide through the day fairly easily.”

“Oh Harry, you’re funny sometimes,” Fluttershy replied with a slight chuckle, and Harry blushed. “Have a good day!”

“You too, Fluttershy,” Harry called out, already skating down the path towards Ponyville. After entering a main street, he headed down southeast towards the Town Hall, where the Carousel Boutique was also located – and also where Harry was headed.

“Hello?” he called, gently knocking on the door. Moments later, it opened. But instead of Rarity, Harry was greeted by a much smaller pony, who had a bubbly mane and a sweet, girly voice – who gasped and shut the door upon seeing Harry towering over her.

Harry shook his head. But then again, Mom always taught him never to answer the door to strangers. He knocked again, this time adding some gentle dialogue: “May I come in, please? I’m Rarity’s friend.”

The door opened again, and it was the same little pony as before. She opened the door fully and let him in – although by her trembling legs she was still scared.

Harry smiled, knelt down, and looked solemnly into the little filly’s big anxious eyes. “Relax, it’s all right. I won’t hurt you, I swear. I’m just here to pick up a few items I ordered previously. What’s your name, little one? Where’s Rarity?”

“I’m Sweetie Belle. Rarity's out buying some supplies, she'll be back soon,” the little filly replied. Her voice, now sounding positive and happy, almost made Harry’s eyes water from her intense cuteness.

“C-can I…hold you?” he asked, him now being the one shaking.

Sweetie Belle extended her front legs out, and Harry picked her up. She wasn’t heavy – about the weight of an older puppy – but she was soft and delicate.

“Awww, your name fits your looks perfectly!” he said, hugging her. For a while, they shared a moment of affection, snuggling and exchanging cheek kisses. Then Harry had a quick theory, so he asked her. “Is Rarity your mother?”

Sweetie Belle shook her head. “Nah, she’s my older sister.”

Harry nodded. “I see. So you do help her out with her sewing and stuff?”

“From time to time, although I tend to only mess up the place,” Sweetie Belle replied, sighing sadly. “I can just be so clumsy sometimes.”

Just then Rarity came running down the road, a saddlebag full of thread spools and small rolls of fabric on her back. “I’m so sorry I took so long, Sweetie Belle! I’ll try not to be late like that again.” She then noticed her little sister was in Harry’s lap. “Harry?”

Sweetie Belle ran up to greet her sister, while Harry apologized for scaring her.

“No worries, Harry. I forgot to tell little Sweetie here about you before,” Rarity said, pulling back a cover on a small clothes rack. “Here are your new outfits, I hope you like them.”

What the actual hell? Harry wondered, sifting through the articles of clothing. Sure, she had made some incredibly well-crafted shirts – one even had an abstract green-and-blue design printed on it –and she’d also made some plain, properly-sized underwear. What disturbed him were the “special articles of clothing.” Instead of making something like a fashionable scarf or a pair of pink-striped socks, Rarity had made him a long-sleeved leotard with a beautiful color design pairing blue, pink, and light green, and a dress. A frickin’ DRESS, with tons of frilly lace, clear rhinestone-lined trim, pink bow ties, complete with a two-tone petticoat of blue and smoke white.

“Why did you make me a dress?” Harry demanded, a look of serious concern on his face. “I’m a guy, not a fashion-loving girl like you!”

“Y-you don’t like it?” Rarity replied, looking as if she was about to cry.

“It’s not that I don’t like it,” Harry said, his tone underlying dissatisfaction. “You did an amazingly detailed job on it. It’s that you made a dress for me, but I’m a guy. Dresses aren’t for guys to wear, neither are leotards.”

Rarity’s face fell. “I…I…I didn’t think of that. I just wanted to surprise you with something unique, and I ended up going with what I specialize in and make the most frequently – dresses. Can you forgive me?”

“It’s alright, Rarity. You’re an amazing seamstress and I admire all the designing, hard work, and dedication you put into everything you make,” Harry said softly, consoling her. Even so, Rarity still looked glum.

A small smile played across Harry’s lips as a plan formed in his head. While Rarity quietly moped, Harry shook off his shirt and pants, snatched the dress, and quietly slipped behind the changing screen.

Getting into the dress wasn’t easy, as Harry obviously hadn’t worn one before. Undoing the zipper, he spread the back apart and while sitting down on a small bench, carefully slipped his legs into the appropriate openings. Then he slowly shimmied his arms through the super-short, puffy sleeves, reached behind, and pulled up the zipper.

“Rather tight on the chest, but its fine,” he thought. Then he pushed back the curtain and walked back over to Rarity.

“Want a little dance before I go?” Harry whispered.

“Really?!” Rarity was shocked. No one ever asked her to dance before.

For five unrealistic minutes, Carousel Boutique looked out of the ordinary on the inside, with a Rule 63 teen boy and an excited, blissful fashionista dancing together like it was the official Grand Galloping Gala ball. Sweetie Belle was lost of words but enjoyed their dancing anyways. Rarity slid out of line a few times due to Harry’s crooked moves, but he soon refined them. Watching Cinderella during a babysitting session had taught him well.

After the dance was over, Harry was more accepting of the dress, though he decided to wear it only during the occasions when he’d visit Princess Celestia.

“At least I’ll wear the leotard, he declared, sliding into the skin-tight suit. “The pants and shirt I’ll reserve for the laborious tasks. Thanks again, Rarity! I’ll pick them up later.”

“You’re welcome,” she replied, waving goodbye as he rode off. “Have a good day at the orchard!”

With shirt and pair of pants slung over one arm, Harry skated back down the road and headed down a southern path that was slightly rougher than Ponyville’s roads, resulting in a rather bumpy ride. Soon the rows of apple trees came into view. And boy, were there hundreds of them!

Harry rode right up to the entrance, where Applejack and several ponies were already busy harvesting apples from a few trees. The country girl soon noticed him from the corner of her eye.

“Howdy, Harry!” Applejack said, halting her apple cart pulling and trotting over to greet him. “Glad you could come.”

“I hope I can be of some good help here,” Harry replied with a chuckle.

“Why are you in a leotard?” a young filly with a dark red mane inquired.

“That’s ‘cause he chose to, Apple Bloom,” Applejack answered.

Harry’s lips twisted in thought. “I’ve seen another filly, little just like you, without a cutie mark. Her name’s Sweetie Belle.”

“She’s my friend, along with Scootaloo,” Apple Bloom said excitedly. “Together, we’re the Cutie Mark Crusaders, and we’re trying our best to get our cutie marks and prove ourselves as fine, talented fillies of Ponyville!”

It must really suck to be the odd ones out from everybody else, Harry thought. “Well, good luck with that. But don’t you guys have like a clubhouse of some sort?”

“They sure sugar do,” Applejack replied. “It’s in the far northeast of the orchard, you can check it out. For now, though, we got some serious apple-picking to do! Granny Smith’s got a long line-up of delicious deserts to make, and she needs these apples ready for baking lickety-split.

“Not hard on my watch!” Harry boasted, gripping an apple cart. Together, he and Applejack, along with Big Macintosh, pulled the carts of apples from the orchard to the barn, where other members of the Apple Family would prepare them further for Granny Smith’s recipes.