Derpy Delivers

by Sollace

Rating: everyone
Tags: Random, Derpy Hooves, Slice of Life, My Little Pony: Friendship is Magic, Comedy
Length: 4404

Whether rain, sleet, snow, or a devilishly handsome three-headed hell hound, the mail must go on.

Whether rain, sleet, snow, or a devilishly handsome three-headed hell hound, the mail must go on. That’s the promise Derpy (Ditzy) Doo made when she joined the delivery mares’ association of Equestria, and that’s the oath she’s determined to keep.

Even if it means she has to, literally, slog through the hidden depths of hell.

Inspired by A thread by BoltStrike58 (spoilers)

Proofreading by Mulberry

Published 2024-10-31 19:10:01 UTC
Last updated 2024-10-31 19:10:01 UTC

1. To Tartarus, And Beyond!

A writhing, pulsating, menacing aura vibrated through a dense fog. The very air hung heavy and buzzed, alight with the dark energies of an unknowable evil. Swirling enigmas, creatures of unnatural shape and form, hidden by the mists, revealed themselves.

They lurked in the farthest reaches of reality with piercing red eyes, glowing in the grey void as they watched their prey. Their claws, gnarled and broken, bending and twisted like the fingers of an ancient elm. They scraped against space, leering, and lurching, twisting with their owner as they sought release from the restricting confines of their ancient tomb.

Like a blackened obelisk, hewn from a single black rock and thrust into the face of Mt. Marelympus by some equally ancient and powerful deity, the doors to Tartarus vibrated and emanated a deep-seated hatred for everything around them as the lone figure of a small mare traipsed up into the small, dimly-lit clearing in front of them.

Far off, far from below the surface of the rock, muffled to nothing but a faint whisper and yet loud enough that if one were to stop and listen—The rushing of the wind turned to a multitude of whispering voices. The cursed souls of the damned, thousands of them, the husky, rabid remains of past adventurers and the like, of everything that must remain unknown, all of their sounds writhing agony as they fought against each other to be heard.

Go back

They whispered, repeating unto themselves, rolling as one in unison. Run. Save yourself. Do not enter this place.

Over and over, the voices of the damned repeated their warnings to the mare that approached, never halting, never breathing or resting. Always pushing and pulling, like the constant beat of a monster’s head. They turned into a blazing, cacophonous avalanche of screaming, howling agony as the doors themselves seemed to grow.

The sunken eyes of misshapen skulls, and blackened bones moved with almost a life of their own as the hidden forces that be turned their attention all at once to the lone fool that saw herself approaching the one place in Equestria no living creature may dare be. Their doom.

As the howling subsided and the mystical wind gave respite, Derpy (Ditzy) Doo straightened her mailmare cap and shuffled her wings, bringing the saddlebags to lie straight against her sides once again. She had to crane her neck all the way back to take in the full height of the blackened doors, and even then, she struggled to focus onto both of them at once, they were so large and threatening.

She could almost see the menacing nature that hung in the air around her as the voices, the echoes in her head turned into a cacophonous scream. Eventually, she had to pull her eyes away from the black obelisks, breaking their spell on her the moment after.

She dipped her head into her saddlebags, putting the doors behind her for a moment. Not soon after, a ghostly wail and spectre swooped through the floor behind her, and phased into the door, where it vanished without a trace.

Derpy turned back around, pulling a small letter out of the bag and flipping it over into her hooves. “Okay, let’s see here…” she whispered to herself. Squinting, and sticking out her tongue, she held the paper almost against her nose as she struggled to make out the—appropriately large—lettering in front of her.

She read the lettering, then read it again, glancing to the doors momentarily to confirm her suspicions, then tossed the letter back into the bottom of her mail carrier bags. “Eeyup! Looks like this is the place!”

She almost did a little clippy-clop as she cantered towards the door, and laid a hoof onto it with a quick little rap.

TAP, TAP, TAP

The doors rumbled. A deafening shudder rang out through them, and all at once the echoing voices fell silent. The twisted creatures scurried away in fright, and the very fog itself seemed to stop its swirling, as if in anticipation of what might happen next.

There was a long and slow creak; the tapping and scurrying of motion on the far side of the doors, and then a soft clack as a tiny slot opened up in the right door, just above eye-level, and then silence.

Derpy frowned. She shuffled her wings against her back, then, looking over her shoulder, she inched forward and pressed her body against the door, getting up onto her hind hooves to give herself just enough height to see into the slot. “Um…” she said, confusion in her voice. She stuck out her tongue as she pressed her muzzle up close to the tiny slit. “Hello?”

There was no response.

And when no other answer came, she leaned in closer still, putting her face almost entirely against the surface of the blackened stone. It was chilling to the touch, vibrating with a dim rumble that pushed back against her hooves, like the rolling thunder of a waterfall. She shouted again, calling into the black void as she squinted after. “Is anypony in there?”

There was a movement on the other side—an appendage, grey and discoloured, flitted out of view. It was barely perceptible. She would have missed it completely if her right eye hadn’t been looking that way when it did, but since it was, and it did, it was clear that it was there.

She was about to call out again when all of a sudden, between blinks, the glowing chartreuse eyes of a stranger appeared before her as if by magic. “Who goes there!?” they boomed, shaking the very foundation of Mt. Marelympus.

“Wh—Woah!” Startled, Derpy tottered away from the door, stumbling back and almost tripping over her own tail. She almost caught herself on her wings for a moment, before landing into a backwards gait.

She settled back into her original position, facing the doors in front of her. Adjusting her cap to make sure it was still on straight, Derpy righted herself and flashed a smile from ear to ear. “Hi!” she chirped, waving her arm like a noodle. “I’m Derpy!”

The voice grumbled. Low and garbled, it spoke, “What dastardly deeds, Derpy, brings you entry to the dark realm?”

Stopping her waving, Derpy lowered her hoof, then transitioned into a thinking pose. She glanced at her saddlebags, momentarily considering digging into them with her muzzle. She shoved her hoof under the flap and fished to the bottom of her left-most pocket, brow furrowed as she looked.

She then stuck out her tongue as she reached the bottom, then shook her head with a chirp, pulling her hoof free to show that it was empty. “Nope, sorry! I don’t have any deeds today. Only letters.”

Silence.

The figure on the other side of the door coughed. “I mean—” It took him a second to recover, but upon contemplating a moment—his eyes dimmed and flickered—the hidden figure resumed: “What demonic dealing have you dealt to gain entry to the darkest pits of hell?”

Derpy tilted her head and scratched behind her ear with a hoof. She inadvertently pushed the cap off-centre as she did so, but the shaking of her head was more than enough to put it straight. “Naaah… I don’t think I’ve done any of that.”

The figure’s eyes narrowed. He repeated, changing his wording slightly. “What heinous horrors have you—”

“What’s that?”

“What despicable diatribe, malicious malignance, violent veracities, selfish sins—What evil ends have you wrongfully wrought to perilously pursue?”

The eyes pulsed with a violent glow as it spoke that last word. Derpy merely stared on in confusion with a blank stare. She raised her hoof, opening her mouth as if to speak, but then, thinking otherwise, she pressed the tip of her frog against her chin as her brow furrowed in thought.

“…No, no…I don’t think I’ve done any of that either.”

The eyes shimmered, going dim for a second. The voice behind the door sounded increasingly annoyed as it hissed. “Then why are you here?”

Derpy’s ears perked up at that. Emitting a short and cute “oh!”, her hoof dove back into her saddlebags to fish out the letter she’d had earlier, and she held it up over her head, waving it clear to see as she proudly proclaimed, “I’m delivering the mail!”

The figure’s eyes showed no emotion, merely stating as a matter of fact: “Tartarus does not receive mail.”

If Derpy had been listening carefully, she might have noticed the slightest hint of annoyance in the demonic being’s voice. Just a little. But since she didn’t really care, she didn’t. She instead waved the letter at the doors in blatant defiance, tittering smugly. “If Tartarus doesn’t receive mail, then what do you think is this?” She smiled, coyly.

It wasn’t often they got a difficult customer, but when they did, Derpy always knew exactly how to handle them. Or was that how not to handle them? Honestly, she had a difficult time getting that straight at times. One day Rainbow Dash might be scolding her for destroying the town hall, and the next they’re praising her as the hero of Ponyville for ridding them of the evil town hall menace that is—

The hidden figure grumbled, waking Derpy from her momentary lapse in concentration. Her eyes straightened, bringing the four doors back into proper focus as he sized her up and down.

When it was becoming evident that he wasn’t going to answer, Derpy snatched the letter back to her side, stuffing it back into her saddlebags as she puffed her cheeks out with a grin. “It’s a letter, of course, silly!”

If she wasn’t mistaken, she could have sworn she saw the monster’s chartreuse eyes roll in their sockets. “Fine—” he hissed. “I will play your foolish games. To whom and where is the letter addressed?”

Derpy’s smile widened. Her wings almost popped open with excitement, but luckily, she had the composure to contain herself as she recited the address from her impeccable memory. “24 South Deville’s Drive, East of the Dragon Lands, at the base of Mt. Marelympus, T.Tartarus. Number 3.”

The eyes narrowed as the figure went silent for a moment. Just then, it was quiet enough for the distant wails of the damned to sneak their way through from behind the slit. “…One moment,” the figure said, before turning away from the slit.

There was a trundling of hooves as he trudged away from the door, followed by the hurried whispers of multiple voices, then a clatter of a stool, and finally the returning clomp, clomp, clomp of hooves as the pair of eyes re-emerged in the middle of the slot. “How did you get that address?”

“Well I am a mailmare,” Derpy said.

That was apparently enough, as the mysterious figure then glanced away from the slot, as if looking at something underneath. “To whom is the letter addressed?”

This, now, gave Derpy pause. She was great with addresses. Everything else? Not so much.

She held up a primary feather, motioning him to wait. “Just one second—” she spat out, then shoved her hoof back into the saddle bags to, once again, fish out the letter she had. Holding it in front of her face, she squinted at the massive lettering, trying to focus both eyes to read enough to make out who it was for.

“It’s…erm…” She turned the letter around, then flipped it upside down and smiled, exhaling as she relaxed suddenly. “It’s for a mister… ‘T’.”

“Mr. T?”

“Yeah.” She nodded. There was more, but it was smudged and too small to make out clearly with her crooked eyes, so she merely smiled and nodded, hoping he wouldn’t press further.

The chartreuse eyes turned down some, possibly checking a register of some kind as the flipping of pages could be heard through the slot, mixed in among the screams of the damned and the pulsating red glow that had just sparked behind his back. “We do not have any souls by the name of ‘Mr. T,’” he said.

Derpy’s shoulders slumped. “…Oh,” she said, but then she quickly brightened as she took a step towards the entranceway to literal hell. “Well… maaaaybe if you let me in, you could—”

There was an uproarious laughter that shook the massive doors and the mountains beside them. Stones and pebbles rained down all around Derpy as the hidden figure laughed and wheezed. “YOU!?” he shouted, his words broken by a fit of laughter. “You cannot enter Tartarus, little pony.”

“Wha—” Derpy was taken aback. She stomped her hoof, pouting as she reared onto her hind legs and flew up to the slot. “Why not?” she shouted back.

“Many warriors and adventurers have dared face the horrors of this land, and all have fallen into agony. Those who did not die surely went insane from the horrors that they faced.

His eyes glowed extra bright as he seemed to lean against the door. There was a clamouring of claws, paws, and something… else against the other side of the entranceway as the hidden figure threw himself against the barrier between them, to bring him if not that much closer to Derpy. “Do you honestly believe that you can face that, for what? A letter?”

Derpy nodded. “Eeyup.”

Another uproarious laughter, and another shaking of the mountain accompanied it. The eyes of the figure were blazing, shining as its hidden dimples were turned up by a twisting smile. “I will let you pass to deliver your little letter, mortal. But mark my words: you were warned.”

The slit slammed shut with a shudder. Its seams melted away into the throbbing surface of the doorway, and almost immediately the doors around them started to shake. The movement started slow and gradual at first—a creaking groan like the horrendous suffering of an arachnid monstrosity howled from the hidden depths as a tiny crack in the doors widened and grew.

But then it picked up, and—a seal broken as a rancid stench wafted from inside, revealing a black void staring at the doors and stretching beyond into infinity. The dark figure, with the chartreuse eyes, the nice pony Derpy had been speaking to, seemed to be nowhere to be seen.

She trotted into the doorway and looked around the edge, hopeful that she might see him, but was met with nothing but more cosmic abyss. Upon seeing that the stallion was gone, Derpy’s ears drooped—she was hoping she’d be able to at least thank him for his kind assistance, but seeing there was no point, she shrugged and pushed on further.

Taking her first steps into the depths of hell, the doors creaked and groaned, slowly closing behind her and plunging Derpy into the darkened abyss.

2. The Gatekeeper

The voids between Equestria and Tartarus were steeped in a broiling black—dark ooze that seeped from the walls stuck to everything it touched, permeating through every space and cranny, threatening to burn away the very air with its acrid, acidic stench.

Silhouetted in the darkness, a shadow watched as Derpy strolled into his realm—Beelzebub was his name. His chartreuse eyes were etched like stars into the darkness, framed above a widening, toothy smile of an infinite twisting and contorted razor-sharp teeth.

He knew not what fate had blessed him so as to have a defenceless pony such as this walk so easily into his web, and with such a careless manner of doing so, too. It was like an insult to the carefully-crafted reputation he had so meticulously cultivated through the millennia.

But, no matter.

A chittering rattled in the darkness as an unseen carapace slid, plate on plate, between each other. There was a slight manic gleam in his eyes as a second pair split open on either side, adding their ethereal yellow glow to the rest.

For his gate-keeper shall take care of this.

~ ~ ~

“Everypony Smile; Smile; Smile—Mmm-Hmmm-mmmm….!”

Derpy hummed a little tune to herself as she fluttered forwards through the dark void. Gliding on the continuous streams of screams and shattered dreams, she would pause between every chorus to give her wings a gentle flap and to correct her heading.

The ground was oddly soft and sticky, and the sludge had only deepened since the moment she’d stepped through the front doors, so she’d eventually opted to give her legs a rest and fly the rest of the way through.

Pulling a deep breath, Derpy pumped her wings, propelling herself forward as she belted out the next line. “…And I know you’re my very best—And I know you’re my very best—And I know you’re my very best—Ooof— ”

The wind was knocked out of her as she collided head-first into what felt like a massive, fuzzy, tree trunk, then she slid down the trunk and landed butt-first atop a pair of equally as fuzzy giant toes.

Derpy squeaked. “…Friends?” she said as her eyes darted around in random directions but never landing in the same direction. She huffed, “Oh, Celestia darn-it.” Frowning with a huff, she bonked herself on the head and immediately brought the spinning to a halt, and looked up at what she’d just landed against.

Now what was this thing she’d run into this time? She silently hoped that it wasn’t something breakable, or valuable, or Filthy Rich—His wife was scary.

Instead, what Derpy found wasn’t either of those things. The giant furry trunk—and really, there wasn’t a better description for it—stretched upwards into the darkness. It was wider around than her entire body, and, seemingly, it wasn’t alone.

Glancing to the side—though unintentionally—Derpy’s other eye spotted a second trunk that stood a few feet to the right of her, identical right down to the toe.

Wait.

Derpy did a double-take, making sure to focus both her eyes on the same thing at once this time. How does a tree have toes?

A large glob of something thick and viscous landed on the ground behind her, causing Derpy to jump and just barely miss the splatter. There was a deep rumble, like the rolling of a thunderstorm that drew her attention up, up, and all the way to the top of the tree as a monstrous beast made itself known.

The titan almost resembled an Ursa, except it was entirely black and covered in a thick fur that glistened like freshly-cleaved flesh. Atop its shoulders— Derpy had to take a step back, or rather a flap as she hovered into the air, jaw hanging open as her eyes widened.

Raising her right hoof, she flew backwards and almost fell off of what she knew must have been its paws as not one, not two, but three heads emerged out of the darkness, each distinct in their nature but all resembling a border collie with their long, toothy, snouts and gnarled angry scowls.

The monster’s giant back arched like a mountain in the distance as it loomed over Derpy, a thunderous growl roaring in the pit of its stomach.

Derpy had to pick her jaw up off the ground, but when she did, she wiped the startled look from her face and waved, smiling and squeaking, “Oh, hi, Cerberus!”

The growling stopped. All three heads froze in place, their expressions changing one after the other to a look of confusion. The left head shared a glance with the middle, and the right head’s ears perked and dropped as its nose twitched.

The middle head glanced down at Derpy, before sniffing, and the three of them shared a few barks before all three of them barked one after the other—the giant monster crouching in front of the tiny pony.

“Bark! Bark! Bark!”

Taking flight, Derpy went in for the kill. She swooped onto Cerberus from the right and unleashed an unyielding assault of hoof pats and belly rubs, all the while cooing and fawning over Cerberus like the giant puppy that he was. “Who’s a good boy?” She grinned. “Who’s a good boy? You are! Yes you are!”

Cerberus responded by rolling over onto his side, revealing his delicate underbelly to the pony’s murderous rampage. Tickles rained down supreme, eliciting a volley of giggles and drooling, panting laughter. Leg kickies and tail waggies resulted, but before baring down on her prey, Derpy pulled back her hoof and came to a halt, hovering over her prey.

“Oh!”

Suddenly remembering something, Derpy alighted on Cerberus’ chest and dug a hoof into her other saddlebag, fishing around as she searched. “I almost forgot…” Derpy’s brow creased as she reached all the way to the bottom. The saddlebags had almost claimed her entire foreleg to the shoulder as Derpy leaned and twisted her back, all the while trying to keep Cerberus on his toes, metaphorically speaking. “Whoooo’s getting you a treat?” she whispered.

“Arf!” Cerberus responded by wagging his tail. The thundering roar and the waves of foaming sludge kicked up around them just about threatened to tear apart the entire hellish realm. Just when Derpy was just about ready to pull her objective out of the bag, she stumbled on her hooves and lost track of it.

She waggled her eyebrows, her voice going a little higher as she teased. “Who’s getting you a treat? I’m getting you a treat!” she squealed, just about breaking down into laughter as she narrowly avoided Cerberus’ second wet nose from tickling her ear—“Specially delivered from Auntie Applejack—”

One of Cerberus’ other heads nudged into Derpy’s side, shoving its nose into her saddlebag. Just his breath alone was enough to almost bowl her completely off of her hooves.

“Ahaaahaa—” Derpy squealed. Her wings popped open on impulse as she struggled to keep her balance against the giant dog’s assault as a second nose prodded at her other saddlebag. Her mane and feathers had been completely ruffled and she couldn’t help but giggle as the middle head, presumably the leader, nuzzled its way under her hoof and into her mail carrier bag.

“H-Hey?” Derpy swatted at the dog’s nose, though her attempt was half-hearted and even less successful. She couldn’t help but stop grinning. “What are you doing?”

Forcing back the giggles, she made a show of force by bonking him on the nose, and Cerberus promptly retreated. Nose scrunched and eyes crossed, the other two heads looked to the middle one with their own two halves of a smirk. “Bark! Bark!” the other two heads said.

Derpy pulled the letter she had from her bag, holding it up over her head for the two heads to see. “‘What’s this?’” she interpreted.

“Bark!”

“Nope…!” She stuck her tongue out at him. “You can’t see it, silly. You’re not the recipient.”

“Arf!”

Derpy puffed her cheeks and waggled a hoof at the naughty puppy. “Don’t you lie to me, mister!” She stuck the letter back into her saddlebags, giving Cerberus a little eye wiggle. “I know you’re not the intended recipient because I’m the mailmare!”

Cerberus’ ears dropped—all three heads miming the other as they joined in unison to give Derpy the triple threat: three full sets of puppydog eyes, with sad little “Hmm-Hmmm-Hmmm” whines.

“Don’t even think about it—” She waggled her hoof even harder. “As the mailmare, I have to follow the sacred code to deliver this letter to the intended recipient. Unopened.”

The puppydog eyes lingered for a second, but as Cerberus grew to understand, each of the heads slowly retreated and returned to normal. Cerberus growled a short little grunt, and one of the heads stuck out its tongue—though Derpy wasn’t sure what that meant, if anything.

They started panting, and the leader of the bunch turned to make a pointing motion with his nose at a spot directly behind Cerberus, where a plain door stood on its own. There was a plastered sign above it that, when Derpy managed to focus both eyes, clearly read “Dante’s Inferno” across the top.

Derpy glanced at the door, and then back to Cerberus—the other two heads had joined the first in pointing at the door and looking at Derpy expectantly.

“Oh.”

She looked at the door again, and then back to Cerberus. Then, lighting up, she replied. “Oh! Thank you!”

The giant dog barked—“Arf!”—and started panting.

Derpy did an about-face and took into the air again, poised to glide back to the ground and to the mysterious door, but before she did, she paused, pointing a hoof into the air. “Oh! I almost forgot!”

She shoved her hoof into her bags and flipped a tiny dog biscuit into the air, which was promptly snapped up by the first of the heads.

“Thanks!” she shouted, before darting off towards Dante’s Inferno.

~ ~ ~

Not long after Derpy’s departure, Beealsibub slunk out of the shadows to find Cerberus reclined on the ground, happily munching on something. At first he smiled, knowing that the deed had been done, but upon getting closer, he became suspicious. First at the lack of blood, and then at the lack of… anything, really.

Cerberus wasn’t the kind to leave remains. Not unless—

Spotting the open door to Dante’s Inferno, Beealzibub’s eyes widened, and his smile turned into a scowl, which then promptly deepened into a more threatening frown. He snapped. “What the bloody hell was that!?” Glaring up Cerberus, Bealsibib slithered through the slime in front of him. “You were supposed to stop her, not help her, you mangy mongrel!”

All three heads of Cerberus snapped to attention as their eyes focused on Bealzibib. An otherworldly roar, like the impending crash of a hurricane mixed with a landslide had a baby with an avalanche, broiled in the beast’s throat.

The monster that was Cerberus moved with a threatening aura, muscles the size of train cars becoming taught and fur sharp as razor blades tightening and pointed. Beulsibub gulped. As the shadow towered over him, he felt the chitin on the back of his neck become cold and clammy.

Taking a step back, he stuttered. “Wait—Wait—I’m Sorry. I didn’t mean th—AAAH-AAAAAH—AAAAAAAAAAAAAAHHHHHH!!!!”

~ ~ ~

“Everypony Smile; Smile; Smile; Sunshine, Sunshine, I just want to make my friends”—There was a loud, blood-curdling scream that echoed out of nowhere—“Smile.”

Derpy stopped in her tracks to look around, but upon seeing nothing, she shrugged and kept going. “My name is Derpy Doo, and I am here to say…”