• Published 6th Nov 2018
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Scootaloo's Best Sleepover Ever - Matt11



Scootaloo spends the weekend with Windy Whistles when the filly's parents have to go in to work. Windy will try her best to be there for the filly she sees as a second daughter.

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Nopony Sleeps

Scootaloo brought her scooter to a careful, skidding halt and stepped down, removing her signature blue helmet. With her wings only good for short bursts of flight just above the ground, her trusty scooter was the only reliable method of transportation.

She looked up at the familiar pillars that defined the front doorstep of her house. A modest structure even by Ponyville standards. Ordinarily she wouldn’t be home at this time of day, it was still quite early and Scootaloo usually longed to stay out until almost sundown. But her mom had insisted she come right home from school today, and considering her mom was often away due to work (the same held true for her dad) Scootaloo knew it had to be important.

Carefully wiping her hooves on the welcome mat (as not to drag dirt or mud into the house) the filly trotted inside after retrieving the key that lay hidden under the mat. She’d been used to doing this for a long time because of her parents’ work schedule. And immediately she was greeted by the familiar pale amber coat of her mother, Dizzy Twister.

Dizzy’s moderate rose eyes fell upon her daughter and she smiled. “Thanks for coming home on time, Scootaloo.”

Scootaloo just smiled back. “Well, you’re my mom. I know that whenever you call me home early it’s for a reason. So what is it this time? Am I in trouble? If this is about my last test, Miss. Cheerilee said it was a pretty tough one for the class.”

Dizzy shook her head and tried not to giggle. “You’re not in trouble, my little pony. It has nothing to do with you,” Then she cleared her throat. “The reason why I called you home, is because I have something very important to tell you. Scootaloo, sweetie, I’m afraid I have to go in to work this weekend and so does your father.”

Scootaloo tried her best to keep a straight face. She’d been looking forward to a fun weekend with her parents, telling them all about what she’d been up to in their absence. It seemed like with every year her parents were away more and more often. Of course she knew why, they were working to ensure they could afford to keep living in Ponyville. But a part of her still couldn’t help but wish her parents weren’t so absent in her life. Even before she’d started attending grade school, it seemed like her parents weren’t as prevalent in her life compared to her Aunt Holiday and Auntie Lofty.

Dizzy could sense that her daughter was unhappy for she had quite a knack for picking up on non-verbal cues (though she wasn’t quite the mind reader her sister-in-law was, Holiday seemed to know what Scootaloo needed before she could even say it). So she quickly stroked her daughter’s mane with a hoof. “I’m so, so sorry, Scootaloo,” She sincerely apologized. “But this is very important and it was a last minute thing. We’re going to be working with Rainbow Dash’s father, the weather factory in Cloudsdale is calling up every able bodied pegasus available to fill a big order.”

“Alright,” Scootaloo sighed before her mood picked up a little. “But that just means Aunt Holiday and Auntie Lofty can come over to foalsit. Holiday always makes the best cookies!”

Dizzy shook her head again. “I’m afraid they won’t be available this time, Scootaloo. They’re out of town all week to celebrate their anniversary, remember?”

“Oh, yeah, yeah,” Scootaloo suddenly remembered and became a bit more downtrodden. “Well, maybe I can just… stay home alone all weekend? Apple Bloom’s family lets her do it all the time now, especially since she started working in the fields.”

But Dizzy frowned at the notion. “I’m afraid I can’t do that, Scootaloo. Apple Bloom’s situation is very different from yours. You’re a good filly, but you do have a tendency to get into trouble when nopony’s watching. And after what happened with The Washouts, I’m a little bit concerned,” Then she decided to sweeten the deal a little. “Besides, wouldn’t you rather have a sleepover at somepony else’s place?”

The tomboyish filly buzzed her wings in excitement at the idea! “Yeah, that’s a great idea! I can stay up late telling scary ghost stories, reading Daring Do, and playing all kinds of fun games! But, who am I gonna be staying with?” She wondered.

“Somepony you’re already very familiar with.” Dizzy responded.

Scootaloo started to ponder who that somepony could be. Maybe it would be Sweetie Belle’s place, or maybe a double sleepover at Carousel Boutique? Or perhaps she’d stay the weekend at Sweet Apple Acres? She even thought about the possibility of staying with the Cakes, even if that meant having to put up with the Cake Twins (they were adorable, but also quite the hoofful. They were getting to that age where they would wander around and poke and pull at anything that caught their intention).

She shuddered at the possibility of it being Diamond Tiara’s family mansion. It was true that the two had patched things up since the former bully had turned over a new leaf, and Filthy Rich couldn’t be happier that his daughter was making new friends. But Diamond’s mom was still very bitter and nasty, it was no secret she despised Diamond’s new friends and blamed them for “corrupting” her daughter. A weekend spent having to avoid Spoiled Rich would be a nightmare for the filly.

Fortunately, it seemed Dizzy already had an idea in mind as she cheerfully explained. “You’ll be staying at Rainbow Dash’s foalhood home. I know Windy Whistles will be glad to see you.”

“Cool! Rainbow Dash’s old home is amazing!” Scootaloo happily exclaimed. “Will Rainbow Dash be visiting too?”

Dizzy giggled at her daughter’s enthusiasm and lightly responded. “I’m afraid not, my little pony. Rainbow Dash is busy with the Wonderbolts. But she specifically told me that she knew she could rely on you to be there for her mom when she can’t. And you’re not going to let your big sister down, are you?”

“Absolutely not! I still owe her for setting up my own fanclub!” The filly eagerly replied! “A sleepover with Windy Whistles will be the coolest thing ever!”

Dizzy smiled. “I knew you’d like it, Scootaloo. Now come on, we need to get everything ready. Your father will be home soon, and I’d like to drop you off at Windy’s place before then.”


Approximately half an hour later, Scootaloo found herself at the front doorstep of the magnificent house that Rainbow Dash had lived in as a foal and then a filly. Her mood was a strange mix of excitement and also nervousness. This would be her first sleepover without any of her friends or her big sister by her side, and much as the filly wouldn’t admit it she always felt a little safer with them around for company.

Windy Whistles would fill that void easily though. She’d become almost like a second mom to Scootaloo (third mom if you counted Aunt Holiday and Auntie Lofty).

Windy greeted the filly (with bulging saddlebags containing everything Scootaloo deemed necessary for a sleepover), wrapping a wing around the young pegasus who had come into her life unexpectedly about a year and a half ago. In a lot of ways she reminded Windy of her own daughter when she was this age. So young and so full of excitement. “Oh hello, Scootaloo!” She cheerfully greeted. “How’s my favorite little filly doing today?!”

“Great, Mrs. Dash!” Scootaloo eagerly replied. “I can’t wait for an awesome sleepover with you! This is going to be the best sleepover in the history of all sleepovers!”

Windy chuckled. “I don’t doubt that one bit. Come on inside and I’ll show you to your room. It used to be Dashie’s, but I managed to clear up some space for a filly on your level.” And she ushered her charge inside.

Scootaloo immediately bolted for Rainbow’s old bedroom, allowing for Windy and Dizzy to converse briefly. Dizzy exchanged a wing shake with Windy. “Thanks again for agreeing to look after Scootaloo for me. You’re a lifesaver, Windy.”

Windy just smiled. “Think nothing of it, Dizzy. Scootaloo and Rainbow Dash are practically family, so by extension you and your husband are a part of my family as well.”

“I’ll be back on Monday by the time school lets out,” Dizzy went on to add. “I assume you’ll have no trouble making sure Scootaloo makes it to school on time?”

Windy nodded. “I’ve been there for Family Appreciation Day, I know the location. You don’t need to worry your pretty little head about Scootaloo, she’s in good hooves with me,” Then she added. “Be sure to say hi to Bow for me, and tell him I miss him very much. I’d have gone to help him, but somepony needs to watch over the house while he’s away.”

Dizzy gave a salute. “Will do, Windy. And thanks again for all your help. If there’s ever any way I can repay you, you let me know,” And when Scootaloo came back into the main room just a second later, she pulled her daughter close and gave her a kiss on the forehead. “Okay, Scootaloo. Be a good little filly for Windy. Make sure to brush your teeth and be in bed by ten, nine on Sunday. And don’t think you can pull a fast one on Windy either.”

Scootaloo couldn’t help but blush a bit even though she didn’t mind the affection. “Mom, stop it, you’re embarrassing me.” She protested.

Dizzy tried not to giggle. “That’s just my way of letting you know how much I love you. I’ll be thinking of you the whole time I’m at work. Now I’d better get back home before my husband starts to worry.” And with a flap of her wings she was gone. Scootaloo and Windy waved at her until she was out of sight.

Although Dizzy was a little further away now, she knew she was going to miss that foal. “I sure hope she does okay without me. I promise when I get back I’ll spend as much time with her as possible, give her so much attention that she won’t want anymore!” Dizzy thought and headed back home.


Once Scootaloo had gotten settled in and had unpacked her things, Windy approached her charge and asked her. “So, Scootaloo, what do you usually like to do for fun at your sleepovers? Truth or dare? Makeovers?”

Scootaloo made a gag face upon hearing the word makeovers. She didn’t mind it so much when she was around Sweetie Belle or Diamond Tiara, because she trusted them enough not to go overboard. “Maybe we could just play some board games?” She suggested. “I’ve got a whole bunch of ‘em.”

Windy smiled. “That sounds like a great idea, Scootaloo. Fair warning though, I play to win.”

“So does everypony else, but my mom and Auntie Lofty are the only ones I’ve ever lost a game against!” Scootaloo boasted. She decided to leave out the time she’d taken a dive during a match against Diamond Tiara, largely because Spoiled had no so subtly instructed her to do so.

The pegasus filly brought several board games to the kitchen, selecting the first one from the stack and carefully unfolding the board as she placed it on the kitchen table. It was Rainbow Dash’s favorite game, the one where you put pieces on a board and took turns with your opponent trying to find and remove them. At least it was easier to understand than the game her aunts liked to play where you went around buying up properties and trading with other players. Auntie Lofty always seemed to know how to give herself an unbeatable advantage there, regardless of what she started with.

“I see you have good taste,” Windy grinned as her moderate cerise eyes set to work on planning where to hide her pieces. “Rainbow Dash loved to play this game all the time as a filly, especially because she won way more often than she lost. She had some pretty clever hiding spaces, I’ll tell you that.”

“Oh yeah?” Scootaloo boasted. “Well I’ll bet I can find even greater hiding places than her! And I know all her secrets! Prepare to lose, Mrs. Dash!”

“Please, you can just call me Windy. We know each other well enough,” Windy corrected as she placed the last of her pieces on the gameboard. “Since you’re my guest, I’ll let you make the first move. Best of luck.”

The tomboyish filly just grinned. “I don’t need luck! You’re going down! Sky Nine.”

“Nope,” Windy said with a grin. “Now it’s my turn. Cloud Five.”

“Hey, no fair! How did you know that’s where I hid my seagull?!” Scootaloo protested and pouted.

Windy giggled. “When you’ve played this game as much as I have, you start learning to think outside the box. Now I’ll go again. Rainbow One.”

“You zapped my weatherpony!” Scootaloo pouted. “Go again.” She resigned herself to the possibility that she would lose without ever getting to take another turn. Windy was too good at this game.

But in fact, Windy missed when it was time to find Scootaloo’s last piece. And that gave Scootaloo an opening. She found two more of Windy’s pieces before she missed. But on her turn, Windy missed again. A few more turns back and forth passed with neither pony finding a piece, until Scootaloo tied it up by stinging Windy’s bumblebee. In the end though, she missed and on Windy’s next turn she found Scootaloo’s last piece and won the game.

“You’re really good at this, Windy,” Scootaloo commented as she put the game away. “Seems I underestimated you.”

The older pegasus flashed a smile. “I did warn you, my little pony. I played this game a lot. Who do you think taught Rainbow Dash all the best hiding places?”

“You mean that was you?!” Scootaloo gasped in realization!

The pegasus mare giggled. “What, did you think she learned all by herself?”


The two pegasi passed the next few hours playing board game after board game. Windy proved to be a more formidable challenger than Scootaloo had expected. The filly narrowly won most of the games. And in the final game, where you put down tiles and spelled out words, Windy beat Scootaloo quite easily.

“I used to be a teacher before I met Bow and settled down to have Rainbow Dash.” Windy had told Scootaloo afterward.

The younger pegasus put the last board game away, just as the clock struck the hour. Six chimes.

Windy knew what that meant, it was time for dinner. And so she set to work on preparing a meal for her guest, while Scootaloo occupied herself by playing with her plushie of Rainbow Dash.

“Scootaloo,” Windy cheerfully and motherly called a short time later. “Dinner is ready. Come and get it before it gets cold.”

With newfound excitement, Scootaloo put down her plushie and raced to the kitchen, climbing into the chair she’d sat in earlier for board game play. She sincerely hoped for her newfound favorite, a pasta and potato sandwich on sourdough. But when her plate was presented to her, she frowned upon seeing a distinct lack of pasta and potato, and certainly no sourdough. Heck, she’d have even settled for a peanut butter and zap apple jam sandwich.

Instead, the filly saw herself staring down a plate of freshly prepared veggies. She stuck out her tongue. “Can’t I have something nicer?” She asked Windy.

Windy shook her head. “I’m sorry, Scootaloo, but you’re a growing filly and you need your nutrition. Your mother was very strict about not letting you fill up on stuff like pasta and potato sandwiches on sourdough. Besides, even Rainbow Dash eats her vegetables. She’s not a picky eater.”

“Do I really have to eat all of this?” Scootaloo complained.

Windy nodded. “I’m afraid so, my little filly,” But then she got an idea. “But I’ll tell you what. If you eat your veggies and don’t make a fuss, I’ll fix you something nice for dessert. My treat.”

“Really?! You’d do that for me?! Mom and Dad aren’t really big on dessert, and Aunt Holiday always insists on not spoiling my appetite.” Scootaloo exclaimed as her eyes lit up with wonder.

“Of course I would, Scootaloo,” Windy happily replied. “But only if you hold up your end of the bargain.”

That did the trick, Scootaloo eat her vegetables without any fuss. Windy just winked. “Works every time.” She thought, remembering how she had used similar tactics with her daughter when she was growing up.

But Windy couldn’t help but be appalled ever so slightly by Scootaloo’s sloppy table manners. “Goodness, Scootaloo. How can you be such a messy eater?” She remarked as she fetched a rag to clean the filly’s face.

“Sorry,” Scootaloo apologized. “I’ve been trying to work on that, especially since Aunt Holiday started giving me lessons. I just got carried away. Those veggies were so good!”

“I’m sure they were, Scootaloo,” Windy replied as she wiped her charge down. “Now, as promised, I’ll make you something extra special for dessert. No peeking though! Shut your eyes, please!”

Scootaloo obliged, covering her face with her hooves. She was thrilled when she was allowed to open her eyes and was presented with a big bowl of chocolate ice cream, topped with chocolate syrup, whipped cream, and caramel. Windy had even put a cherry on top.

This time, the filly made sure to eat more carefully so as not to make so much of a mess. She still got traces of ice cream and caramel all over by the time she was done though. But in her defense that ice cream sundae was really good!


After dinner, the two cuddled up on the couch to look through the photo album. Scootaloo couldn’t help but feel a little bit guilty for browsing through Rainbow Dash’s baby pictures, but they were just so adorable and funny. She got a real kick out of the one that showed a Rainbow Dash no more than two or three years old, who had managed to tie up her mother.

“That’s Rainbow Dash for you,” Windy chuckled a little. “Even back then she was full of energy. Never wanted to sit still. It’s no surprise she wanted to become a Wonderbolt, she was a born athlete.”

“Yeah.” Scootaloo nodded and sighed a little as she unintentionally recalled the trouble she’d been having with her wings. She still wanted to hold out hope that she could find a way to make them work, or find some other way to achieve flight. But for now, her options were more or less limited to hovering just above the ground or riding her trusty scooter. Corrective surgery or transplants were too expensive.

“Oh, what’s wrong, Scootaloo?” Windy innocently asked. “You know I can’t stand to see my favorite filly so down in the dumps.”

“It’s nothing, really,” Scootaloo sighed again. “It’s just that, I want to fly as well as Rainbow Dash someday. Or at least, close to that kind of level. But my wings just don’t seem to want to work no matter what I do.”

Windy wrapped a wing around her charge for comfort. “Scootaloo, I’m sure a filly like you will find a way! Take it from a teacher who had a lot of students with flying problems, there’s always a way to soar above the clouds. And knowing you, I’m sure you’ll find a solution and join the ranks of the Wonderbolts alongside Rainbow Dash! Heck, Bow was the weakest flyer in his class, but you’d never know that from the way he flys nowadays.”


After that little pep talk the rest of the evening past uneventfully until roughly nine o’clock, half an hour before Scootaloo’s scheduled bed time.

Something nagged at Windy’s mind and she put a hoof to her chin. A fact that did not go unnoticed by Scootaloo. “What’s wrong, Windy?” She inquired.

“Scootaloo, when was the last time a filly like you had a bath?” Windy bluntly asked.

Scootaloo massaged the back of her neck with a hoof. “I… don’t know. I don’t really keep track of that kind of thing. I usually take one or two a week, maybe three if I get really dirty. Most of the time I’ll just hose off at Sweet Apple Acres before I come home.”

“Well that settles it then,” Windy declared. “You’re getting a bath tonight, my little pony. I want to make sure you’re nice and squeaky clean.”

“Can it be a bubble bath?” The tomboyish filly pleaded.

Windy shook her head. “No, just a regular bath, I’m afraid. But maybe you’d like a few toys to play with?”

At that, Scootaloo replied. “Just give me a rubber duck and a toy ship and I’m good. It’s a good thing Mom made me pack that special wing shampoo. The last time I washed without it, my wings got all slippery and took forever to dry.”

“Very well then, you go fetch that shampoo and I’ll get the bath started,” Windy instructed. “It might also be good to use the bathroom at this time.”

“I’m not four,” Scootaloo protested. “I haven’t wet the bed or had an accident in years.” But she still obliged. She was Windy’s guest, and it was a rule at sleepovers that the guest respected the wishes of their host (even when said host was a pony like Spoiled Rich).


After using the bathroom and washing her hooves Scootaloo stepped gently into the tub, delighting in the warm water as it made contact with her fur. At least unlike at home she didn’t have to worry about somepony else using up all the hot water (as often tended to happen).

Windy scrubbed Scootaloo’s coat and hooves thoroughly, making sure to get every trace of dirt and grime off. Once that was done she allowed her charge to soak in the tub and splash about for a while (fortunately, Windy had had the foresight to place a few towels around the tub for just such an occasion), before she eventually pulled the plug and helped the filly out. Scootaloo didn’t need any help to dry off though.

When the bath was over it was time for Scootaloo to go to bed, much to her protests. “I’m not tired.” She protested even as a yawn betrayed her statement.

Windy just kissed Scootaloo lightly on the forehead. “Well it is your bedtime, Scootaloo. And it’s not a sleepover if nopony sleeps,” She pulled the bed sheets up to the filly’s neckline and then trotted over to the bedroom door. “If you need anything, my room’s just down the hall. Want me to leave a nightlight on for you?”

“No,” Scootaloo yawned again. “I can sleep just fine without one.”

“Alright then, no nightlight,” The elder pegasus acknowledged and then she sweetly called. “Sweet dreams, Scootaloo. See you in the morning.” And with that she closed the bedroom door and left. She decided to stay up for a little while longer, just in case anything might come up. But then she too grew tired and decided to call it a night.

Author's Note:

Thought I'd try something new, I don't see many fics with Scootaloo and Windy much so this collab idea was something I thought could work.