Azurala's 30 Day Derpy Whooves Challenge

by Azurala

Rating: everyone
Tags: Random, Derpy Hooves, Crossover, Doctor Whooves, My Little Pony: Friendship is Magic, Romance
Length: 3783

Could 30 days and 30 prompts of Derpy and the Doctor ever go wrong? Never.

Thirty days, thirty prompts, thirty scenes, all with our favorites: Derpy and the Doctor!

Every chapter will be labeled with the prompt.

Published 2015-05-06 19:30:06 UTC
Last updated 2015-11-17 04:00:30 UTC

Holding Hooves

"How are you doing that?" The Doctor asked as he stumbled along on three hooves, one hoof currently being held by Derpy.

"Doing what?" Derpy cast a sideways look in the Doctor's direction, ruffling her wings up against the crisp morning air.

"Walking and holding my hand-- my hoof? Aren't equines supposed to walk on four legs?" He stumbled over a rock, and the two of them would've gone down if it wasn't for Derpy's impressive strength and response time. "Oof."

Shrugging her shoulders, Derpy lifted the Doctor up off the ground. "I dunno. I guess it's just a thing everypony knows how to do. Except," she mutters to herself, "Except you apparently."

"Except what?" The Doctor asked, finally balanced again on three hooves.

"Oh, nothing." Derpy lied, opening and closing her wings in a sort of fidget. "Let's just keep going." She pulled him along, making it up over the hill they'd been working on for probably a good ten minutes before the Doctor spoke up again.

"Where are you taking me, anyways?"

"Oh!" Pomfing her wings open, Derpy skipped once , nearly making the Doctor fall flat on his muzzle. "It's the Hoof Holding Celebration today! Didn't I tell you? I thought I did..."

"No, ah, you didn't. Uh-- hoof holding? Oh, oh, of course! Hand holding! Yes." The Doctor thought about it for a moment, and would've blanched if not for his fur. "Wait... Hoof holding? Why are we holding hooves?"

Derpy's smile folded down. "Aren't we friends?"

"I-I mean, yes, we are friends, miss Hooves, I just thought.... Doesn't hand hol-- hoof holding mean something here?" He tried to pull his hoof away, but the pegasus had a grip of steel.

"What do you mean? Mean something? It means we're friends, right? Don't friends hold hooves?" Derpy's eye went lazy as she lost her concentration, tugging on the Doctor's hoof in earnest.

"Well, miss Hooves, I know we're friends, but hoof, or hand, holding, where I come from, means... Means more than just being friends. Does that make sense?" Unthinkingly, the Doctor stood up on his hind legs to brush back his mane nervously before setting his hoof back down.

"You just stood on your back hooves!"

"Wha--" The Doctor looked down at his hooves and frowned. "I guess so! Huh! How odd... How did I do that?" Rearing up too far to do it again, he fell backwards onto his back and brought Derpy down on top of him.

"Oh... I'm sorry, Doctor, let me help you up!" Derpy scrambled off her strange friend, shaking dirt off her coat and beating her wings. She offered a hoof to him, but he stared at it blankly.

"I... Really still don't know how to grab anything with these hooves. Let me get myself up." He rolled side to side on his back pitifully, trying to gain enough force to turn himself over. After a minute of trying, he covered his face with his hooves. "I can't get up."

Derpy cocked her head and twitched her ears. "What?"

"I said," the Doctor muttered around his hooves, "I. Can't. Get. Up."

"You're ridiculous."

"Yes, thank you, miss Hooves. Please help me."

"Oh, yeah. Ok." She grabbed one of his hooves and pulled him up with one beat of her wings, dumping him hooves-down onto the ground. "There you go!"

"Thanks. Now...." He shook out his fur, poofing out his coat and mane in agitation. "Where were we? Ah, yes. Where I come from, holding hooves means, uh, being in love, I guess? I don't... Really know. I mean... I would always hold Rose's hand while we ran, but... That's different, I think..."

"Oh..." Landing softly on the ground, Derpy closed her wings and looked away from the Doctor, hoofing at the ground. "I guess holding hooves means the same thing here in Ponyville, and I just... I'm sorry, Doctor."

Eyes going wide, the Doctor stuttered in response. "Well, umm. Miss Hooves, yes, I concur, it is probably the same here as there, and... Oh. I. Umm. Don't know what to say, Derpy. I'm... Sorry, too."

Silence settled over the odd pair, the Doctor still puffed up and Derpy preening her wings nervously. The sun moved a little in the sky before either spoke again.

"So... I guess we should get going, then, yes?" The Doctor stood back up onto his hooves, craning his head back to lick some fur down.

"You... Just licked yourself, Doctor."

"Yes, so I did."

"...Ok."

Silence again for a moment. "Would you like to hold han-- hooves, miss Hooves?"

Derpy's wings pomfed out uncontrollably. "Y-yes."

The Doctor offered his hoof with a toothy smile. "Then lead on."

Fumbling for a second, half due to her clutziness and half due to the Doctor's inability to grab anything with his hooves, Derpy took his hoof in hers and pulled him along again, over the crest of the hill. "You'll love the celebration! All sorts of ponies will be there, holding hooves! Rarity and Fluttershy, Cheerilee and Big Mac, the Mayor and her husband! Ooooh! We'll be there, too! Everypony will see us holding hooves!"

The Doctor blushed furiously under his coat. "Yes, of course... Uh, miss Hooves--"

"Can't you just call me Derpy? We are holding hooves, after all."

"Umm, yes. Derpy." The Doctor cleared his throat. "Are you sure you want to be seen holding hooves with a strange pony?"

"Doctor." Derpy wheeled on him, eyebrows crooked down and both eyes fixed onto his. "We're both strange ponies. Unique ponies. Does that bother you?"

"N-no, no! Of course not, Derpy! I'm only worried about you!"

Derpy shrugged. "It wouldn't be the strangest thing that's ever happened in Ponyville."

The Doctor could clearly recall the strange "Nightmare Moon" he'd seen cause trouble the first time the TARDIS had brought him to Ponyville. "No..." His smile returned brightly. "I guess not."

Cuddling Somewhere

The Doctor sighed contentedly, taking in the blueberry scent of Derpy's mane in a slow inhale, his nose buried in her flaxen locks. "You are quite the marvelous creature, Derpy Hooves."

"Thanks, Doctor." Derpy turned her head to nuzzle their noses together, big golden eyes half-lidded with sleepiness. "You're pretty great, too. Kinda weird, though."

He snorts. "We are both wonderfully unique. Saying we're weird is just... Well, weird. Nobody--"

"Nopony." Derpy interrupted casually.

"Right. Nopony is actually weird, you see. Weirdness is just an illusion created by social norms and a pony's opinions. When you look at somepony and think they're weird, you're actually wrong, because this pony is exactly how the universe intended to create it, and you're just thinking backwards of everything the universe knows is right."

Derpy stared into the pleasantly flickering fire in the hearth, slowly processing what her coltfriend had said. "No."

"No! No?" The Doctor went agape and spluttered when hair got into his mouth. "You're saying the universe is wrong! And if there's anything I've learned in all my travels, it's that the universe is always right and sometimes we just can't see it because it's on such a grand scale that is unable to be perceived by such small, totally inconsequential organisms like ourselves... You can't really--"

"No, Doctor. You're definitely weird." Derpy pushed herself over so she splayed out on her side, her head resting on the Doctor's outstretched front legs. "The universe was wrong this time."

Half an indignant whinny escaped the Doctor's mouth before he realized that this was an argument he would never be free of. "Fine. I guess I am a little weird, huh?" He laid his head down on her shoulder, catching another whiff of her blueberry shampoo. "Not knowing how to pick things up with these hooves and whatnot."

Derpy only made a small, contented noise, half asleep already.

Gaming/Watching a Movie

"Derpy!"

Turning around, Derpy sees the Doctor at the TARDIS door, a cable in his mouth. "What did you find in there this time?"

Prancing back and forth on all four hooves, his eyes bright, the Doctor motions for Derpy to follow him. "I forgot about this room that a companion of mine filled with these devices..." He turns around and dashes off into the blue box.

Hurrying to follow, Derpy trots on behind him and down the stairs. "Devices? Like what?"

Following the cord back, past multiple doors, and down another flight of stairs, the Doctor stops short in an archway. "I think they are entertainment systems, video games and such. Rose used to spend a lot of time down here..."

"Video... Games?" Derpy cocks her head to one side. "Like those arcade games at fairs?"

"Yes! Yes, like arcade games. You press buttons and things bleep and bloop and...." Flipping a switch on the wall, systems and TVs power on all around the large room, whirring to life. "Ahah! There we go. Now, let's take a look..."

Rose had showed him years ago how to operate each game system, and to turn them on using the controllers, but when he went to grab the first one he saw, a realization came crashing down upon him. "Wait... We can't use these things, can we?"

"What do you mean, Doc? "

Fumbling around with the controller, and nearly dropping it a few times, the Doctor gives an irritated huff. "These damned hooves, Derpy! You need hands to play video games! Hands!"

"'Hands'?" Derpy's nose scrunches up in confusion. "But nopony has hands, Doc. Monkeys have hands, I guess, but, I mean..." She trails off, scratching behind her ear.

"Yes, well, I've met a lot of talking monkeys in my day and none of them ever told me that one day I'd wake up in a universe where I have hooves." He grumbles under his breath, tossing the controller aside. "But, that doesn't matter now. There has to be something here that we can do, miss Hooves, and I'm going to find it!"

Taking his screwdriver from where it perches behind his ear, he points it at the closest system. After changing the frequency a few times, it beeps once and the TV flickers on. Rather upbeat music (not unlike what Derpy can sometimes hear coming from her neighbor's house) starts playing, and panels on the floor light up and flash. Examining them, the Doctor gives a little hop of elation. "Oh, this is marvelous! This little game was so fun! And, with some practice, I bet we could play!"

"What does it do?" Derpy trots over, tapping on the lit squares with her hooves experimentally.

Clicking the screwdriver a few more times, the Doctor gets the game to select something on the screen. "You start the music like this..." A new song starts with a swell of guitar. "And you stand on these things," he tugs Derpy over onto one of the squares, helping her to position her hooves, "and then, you watch the screen. See, it tells you which arrow to step on to get points to win the game-- each arrow moves up the screen, and when it reaches the top, you press it with your foot-- err, hoof."

Watching the screen curiously, Derpy sees an arrow pointing upwards move to the top and, looking down, she presses the up arrow with a hoof. 'Great' flashes on the screen for a second before another arrow comes up, this time pointing left. Moving her hoof, she taps at the left arrow. "I don't know, Doc, this is weird."

"You have to get into it, Derpy! Really play the game! The arrows will get faster and there will be more, so use all of your hooves to hit the panels on time, and it's like dancing!" The Doctor, eyes glued to the screen, starts moving his hooves to hit each arrow as the screen shows. "You'll get the hang of it!"

Trying to watch her hooves and the screen at the same time, Derpy slowly begins to pick up pace until she's bouncing along with the Doctor to the beat of the strange music. "Haha! This is fun, Doc!"

Once the song ends, a voice on the TV announces player two as the winner. The Doctor's jaw drops. "You beat me! Miss Hooves, you won!"

"Yay! I can't believe I got something right!" Derpy flutters her wings in elation. "I want to play again! Oh, Doc, can we play again?"

Laughing at his newest assistant's enthusiasm, the Doctor points the screwdriver at the screen. "We can play all day, miss Hooves."

Kissing

"How does, you know, kissing work, in this world?"

Derpy turns her head over her shoulder to look at the Doctor where he's splayed out on the couch, narrowing her eyes. "I mean, we have lips and tongues and stuff, I guess... I just... I've never, you know... Kissed anypony."

Bolting up from his spot, face comically shocked, he clears the space between them in one bound. "How can you have never been kissed, Derpy!? You even have a little one!"

Pursing her lips, Derpy flips her hair over her lazy eye out of habit. "I, ummm... Don't like to talk about it, Doc."

"Oh." Biting his lip now, the Doctor knickers under his breath. "I'm sorry, Derpy. I guess I just don't think about these things that I say, and--"

"No! No, Doc, you're ok, I just don't want to talk about it." Giving him a small, nervous smile, Derpy taps her hoof on the coffee table next to her love seat. "I've never dated anypony or anything, and I just... Guess I've never felt the need to kiss anypony, either."

Scuffing his hoof on the carpet a few times, the Doctor huffs a sigh. "Well, I'm sorry, Derpy, if it makes any difference. I didn't mean to bring up anything uncomfortable and-- mmff..." He would've continued to apologize, if it wasn't for the lips on his.

Derpy pulls away, sitting back on her haunches on the couch. "Sorry, Doc. I know it wasn't too good, but it was my first kiss."

"I-- uh, umm, well, yes. *ahem*" He fans himself, unhelpfully, with a hoof. "Yes. Umm. Very good, miss Hooves."

"Derpy."

"Yes."

Wearing Each Other's Clothes

"Is this how it works, Doc?" Derpy looks up from where she'd been working on tying the silky fabric into an unrecognizable knot.

The Doctor didn't even look back over his shoulder, too focused on his work. "Probably not. I'm not even sure how to tie a bowtie with these blasted hooves! Do you want me to do it for you?"

"Please?" Derpy sits back on her rump in frustration with a pout on her face, her lazy eye fallen to the side. "I just don't understand how you wear these all the time! Do you tie them every day?"

"I did," the Doctor mutters, "back when I had hands!" Pushing away from the TARDIS' console, he rolls effortlessly over to Derpy in his rolling chair. "Let's take a look, shall we?" Undoing the silken knot Derpy had tied, the Doctor fumbles a bit with the strands. "Let's see... Under and over... To the right, the left, and under again..." He tugs on the lapels and stands back to admire his work. "There! Now, uh... Why did you want to wear a bowtie again?"

Derpy prances over to the mirror to take in herself, all prettied up in her bowtie. "It's Nightmare Night tonight, and I wanted to look mysterious!" She picks up a tweed jacket and slips it on over her shoulders, tucking her wings underneath. "And I figured that you're the most mysterious pony in Ponyville. Besides," she picks up a pair of glasses and pops them on her face, "You're very fashionable, Doc."

"Ha! Well, if you're looking for mysterious," he bounces off his chair and rummages in an old, Gallifreyan labeled trunk beside the mirror, "I would suggest this!" He produces a long, khaki colored trench coat from the depths of the trunk, along with a brown suit vest and blue tie on a hanger. "I wore this in my... Let's just say, 'emotional' period."

"Ooooh-ing" at the outfit, Derpy shrugs off her tweed jacket and tugs at the bow tie, but only manages to get her hoof stuck at the hollow of her throat. "Doc-- help, please..."

Expertly untying the bow tie, the Doctor slowly pulls the silk strip from Derpy's neck. "Now, I can definitely tie a regular tie with these hooves..." He slips the striped tie over Derpy's neck, about to start on knotting it when he's pulled forward, bumping his snout into Derpy's.

Derpy draws back from the impromptu kiss, giggling at the Doctor's red face. "You totally fell for that one, Doc. Everypony knows it's easy to rope you in with a tie."

"Oh, yeah?" The Doctor smirks, tugging on his end of the tie to bring Derpy closer, bumping snouts a little more elegantly this time and making lip contact for a short moment. "Two can play this game!"

Giggles turning incensed, Derpy gives another, slightly too overzealous pull on the silken fabric, falling backwards in glee onto the floor and bringing the Doctor down on top of her. "Well, the two of us can play another game, too, Doc."

Nuzzling at Derpy's neck, the Doctor knickers under his breath. "We sure can."

Author's Note

Needless to say, Derpy only barely made it out of the TARDIS dressed and ready to take Dinky Doo out for Nightmare Night.

Cosplaying

The Doctor stops short in his tracks at the entrance to the TARDIS, his mouth agape. "Derpy, what is that you're wearing?"

Derpy turns to face the Doctor with a flourish of the white dress she wore, the gems on the breast piece glinting in the light of the TARDIS' instruments. "Isn't it pretty, Doc? I found it in one of your closets! I hope you don't mind?"

Stammering, the Doctor trots over to examine the dress. "W-well, I," he lifts up the material of the train, holding it to his nose and catching the faintest scent of her, "I haven't seen anyone in this dress in a long, long time, Derpy. It... Meant quite a lot to the two of us."

Frowning, Derpy begins to slip the top off. "I'm sorry, Doc, I guess I shouldn't be rummaging around in here, especially if it brings up bad memories..."

"No! No, it's fine, Derpy, I just---" He caresses the fabric gently before letting it slip from his hooves. "--It brings back more good memories than bad, but even the best of things can make a person sad sometimes."

"A pony." Derpy corrects him.

"A-- what? Oh, yes, a pony. They can make a pony sad. Just to remember the good times shared between Ms. Noble and I, so many adventures..." He trails off, shaking his head. "But! You're missing a piece, my finest assistant, something what makes the dress even more perfect!"

Watching the Doctor gallop off to a keepsake box he keeps perched meticulously on the TARDIS' console, Derpy bites her lip pensively. "I don't have to wear it, Doc, if it's gonna be a problem..."

"Oh, it's no problem at all, dearest! If you're going to wear it though, you might as well have," he pulls out a pristine, white, sheer fabric, attached to a headdress of some sort, "the veil! The most important part of any woman-- mare's wedding dress!"

Derpy's eyes go wide at the sheen of the pearls on the tiara, and she nearly trips over her dress to get to it. Arranging it behind her ears to flip the veil over her face, Derpy flutters her eyelashes from where their hidden behind the sheer fabric. "Am I pretty, yet, Doc?"

Stifling a whinny, the Doctor reaches up to flip the veil back from Derpy's face and places a kiss on each blushing cheek. "You are more than pretty, miss Derpy. Beautiful, I'd say."

Flushing from v-line to ear tip, Derpy swats a hoof at the Doctor playfully. "Stop it you, you're making me blush."

Smiling genuinely, the Doctor traces a hoof from the crest of the tiara to the dip of the v-line. "Good, good. A pony deserves to be flattered every once in a while."

On a Date

Sitting quietly at the table he'd grabbed for him and Derpy, the Doctor sipped his cuppa nervously. Surely this cant be a date, he thought. Derpy's not the kind of girl to take a strange pon-- person on a date, right? Does she think I'm weird? Does she have parents? Do I have to MEET THEM? Oh Gods, oh Gods, oh Gods--

"Doctor?"

Startling out of his thoughts, the Doctor looks up to see that Derpy had obtained her coffee and was now sitting across from him. Oh Gods, how long has she been there? "What did you get?"

"Oh," Derpy smiles down at the red cup, "I always get a peppermint mocha this time of year. Peppermint is my favorite flavor, but I can never put it in a muffin so I never get to have it."

"I-- uh, got some sweet grass and lemon tea with a pump of timothy hay flavor. It's, well... It certainly tastes like hay and grass."

Derpy giggles. "Still getting used to pony food, Doc?"

"Certainly." Scratching behind his ear nervously, the Doctor gives her a small smile. "So, umm... Well, Derpy, I have to ask, but I hate to, if it makes it awkward, and, umm, well, are we on... No, is this...? I just..." He trails off and whinnies under his breath, his cheeks warm under his fur.

Across the table, Derpy breaks out into a laughing fit. "Oh, Doc, haha--" She takes a few breaths between her laughing, trying not to double over out of her chair. "Doc, Doc, oh-- oh, Celestia, that's great! You can't even ask!"

The Doctor feels his whole face go hot. "Well, I don't want to make things awkward if it isn't, I mean, I don't know Derpy, I've never been on one and I just don't know what to do, and..."

"Oh, Doc, you're so wonderful." Derpy's regained herself now, and plants her hooves on the table, leaning over to give the Doctor a quick kiss on his flushed cheek. "Yes, this is a date."

Touching a hoof to his cheek, the Doctor's smile grows wider. "Well-- uh-- I guess that answers that. Thank you, miss Hooves."

"Derpy, Doc. Just Derpy now. No more Hooves."

The Doctor is even more flustered now. "Right, well, miss Hoo-- Derpy. Thank you for bringing me on this date."

"You're welcome, Doc."