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.