Derpiween Part 1/2

Derpiween Part 1/2 by Writeslut_The_Anon
Note that “BREAK” signifies where the document was separated for 4chan.
Will be revised as progress on the second part is made, as the first part was slightly rushed for Halloween.


Derpy Hooves could barely contain her excitement. She had planned, designed, purchased and crafted the best costume of Princess Celestia in Equestria’s history. Now, with only a few hours to spare before Nightmare Night officially began, all she had to do was put it on…
>”Look out Ponyville! Derpy’s competing this year!”
After a quick strip out of her everyday outfit, the ditzy mailmare began putting on her costume.
On went the armbraces, the shoes, the panties, the bra, the tiara and the little cardboard horn. Now it was time for the final step. Grabbing the small canister of compressed air, Derpy Hooves took the hose, slid aside her panties and inserted the nozzle into her slit. She shivered a little at the coldness of the metal, but nevertheless she turned the handle of the canister, perhaps a bit too fast. Derpy moaned softly as the air poured into her, filling her out into the form she envisioned. Her soft breasts began to grow fat and full, billowing out into a sensitive pair of pillowy flesh. Meanwhile, her once slender thighs, hips and ass all became round and plump as the hissing air filled them. The grey pegasus bit her lip, trying to dull the growing flames of pleasure that had risen from her inflation. She couldn’t lose herself in her glorious body yet, lest she forget to prevent herself from growing TOO big…
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A little more…
A little more…
Perfect!
Finally satisfied with her figure, Derpy Hooves took a moment to admire herself in the mirror. She smiled. She really looked like Princess Celestia, her costume was perfect. A quick glance at the clock revealed that she still had an hour to kill, which she smirked at the idea of. A squeeze of her breast elicited a pleasurable buzz that grew a blush on her face, and a dampness to her nethers. With a klutzy sort of grace, Derpy hopped into her bed and explored her immense new figure. Her watermelon-sized bust became a playground for her fingers as she pushed aside her golden bra and prodded at her swollen nipples. Every little rub was worthy of a moan or gasp from the ballooned mare, accompanied by a thin stream of air escaping from the stimulation. Eventually, her hands found their way to her dripping pussy, which was plump and filled with air as well. She began to stroke and tease it in earnest, turning the burning lust into a roaring blaze as she went wild. Her legs bounced in stimulation, grinding together against her pussy and hand with a pleasant squeak. Sweat began to bead down her forehead as she slid her fingers into her puffy vulva, teasing and stroking against its sensitive walls. Derpy’s breath began to come short, her tongue hung from her mouth as she gasped and squealed in pleasure. She was drunk with heart-pounding lust, her hips began to buck as she neared orgasm, before she squeezed against herself finally coming to a climax.
Derpy finally let out a breath of pure satisfaction, simply lying there and collecting herself.
Wait, what time was it?
>”Oh no!”
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Derpy Hooves trotted merrily along Ponyville main street, drawing practically every eye and lowering every jaw. To be fair, though, she was showing more skin than every underwear commercial in existence, sporting an enormous grey rump that simply refused to be covered, threatening to burst out of her flimsy panties and squeaking with every happy stride, and a huge pair of breasts that oozed out of her bra, nopony could look anywhere else.
The fact that she stood a few heads taller than anypony else helped too.
Nevertheless, Derpy Hooves was oblivious to it all, her head clouded with thoughts of this year’s festivities, and her friends that were waiting for her.
Derpy’s eyes suddenly widened
>”Oh no! They’re still waiting, and I’m still late!”
With that, the curvaceous pegasus broke into a sprint, zipping away from the gaggle of costumed ponies that watched her until she was completely out of sight.
One by one, the gaping ponies closed their mouths, shook their heads and got back to setting up for Nightmare Night.
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Meanwhile in Carrot Top’s house, a group of ponies sat in the living room, awaiting the last member before they would begin planning for the night. Cookies and punch had been provided, but nevertheless, one pony was grumbling.
>”Uuugh, she’s always late! Why is she always late!?”
>”She’s only a few minutes late, Lyra.”
>”I know Bon-Bon! It’s just that we’re already missing Vinyl and Octavia! This barely feels like a party!”
Bon-Bon nodded slightly. The musical duo had been called away to set up for the dance off, leaving only herself, Lyra, Carrot Top and Berry Punch. Berry had, of course, shown up drunk and passed out on the couch, so she really only counted as half a pony. Carrot Top sighed.
>”She’ll be here soon. She never misses our Nightmare Night get-togethers.”
As if on cue, the doorbell rang.
Every (conscious) pony sat bolt upright, and was at the door at an instant. Carrot Top, being the gracious host, opened the door to reveal-
>”Hey guys!”
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By some miracle, Derpy Hooves was able to fit through the door. Despite this hardship, the grey pegasus remained as jolly as ever. From there, it was a bumpy walk to the living room. Most of the group’s effort was directed into moving furniture out of the walls, as the immenseness of their friend scraped clean against the cramped hallway walls. Finally, the group arrived at the living room. Derpy took the sofa, which hugged her rump quite snugly. Bon-Bon, Carrot Top and Lyra got out folding chairs, while the snoring Berry Punch continued to occupy the easy chair.
And for a while, that was it.
Everypony was content to sit in stunned silence barring Derpy, who munched on a cookie while she waited for the others to fill her in on whatever she had missed.
It took Berry toppling out of her seat, waking up, violently swearing something about “fucking vampires”, subsequently deciding not to care and falling back to sleep to snap the gang out of their trance. Carrot Top was the first to speak
>”Oh, um… How do we start this thing again?”
Derpy was all too happy to answer.
>”We usually show off our costumes, Carrot!”
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>”O-oh, um… Well then, uh… Lyra? Care to explain your costume?
Lyra stood, presenting her chosen outfit for the night.
It consisted of a white toga, white paper wings and a golden halo. She also carried her trademark lyre.
>”I’m going as an angel pony. I’ve got my wings, halo and ‘harp’, pretty simple really. Your turn, um, Bon-Bon!
Bon-Bon rose from her seat. Her outfit was made up of the standard witch affair, with a black, pointed hat and robe. She also carried a broom for the added authenticity.
>”I’m a witch. Not much else to be said. Your turn Carrot Top.
Carrot Top stood. She was dressed as a carrot.
>”I believe my costume speaks for itself. D-Derpy? What are you dressed ass- I MEAN, AS!”
The grey pegasus stood up with a squeak. Her glorious rear end casting a shadow over the curious ponies that had dared to inquire of its origins. As Derpy did a little twirl to show off every angle, her backside loomed above the heads of her peers, inadvertently showing off the lips of her pussy, clearly defined against the stretched out fabric. Her heaving breasts were larger than her head, jiggling and swaying with every movement she made. Aside from her physical form, Derpy was wearing plastic replicas of the royal regalia, and a cardboard horn. Breaking out into a tiny giggle, then a calm smile, Derpy Hooves spoke as royally as she could:
>”I’m Princess Celestia!”
And she said no more.
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After the informative cop-out, the group set about planning. However, a strange jealousy had taken root, and whispering amongst the normal-sized mares took place when the immense pegasus wasn’t around. Between kitchen expeditions and bathroom breaks, a little conspiracy began to grow.
>”How!? Just- How!?”
>”I don’t know! Do you think it’s some kind of implant?”
>”I doubt she’d do something that drastic for Nightmare Night. It can’t possibly be fake!”
>”Then what is it?”
>”I just said I didn’t know!”
>”I got a good look! It’s massive!”
>”No shit sherlock!”
>”But I’m dressed as a carrot!”
>”That’s fine and all, but could you tell us something we don’t know?”
>”U-uh, ok, ummm… Oh! The fur looked really real, but the skin behind it looked shiny! Every other implant I’ve seen had it the other way around!”
>”That just makes narrows it down to a really fancy implant or every other option doofus!”
>”GIRLS!”
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The trio of bickering mares closed their mouths. Berry Punch was on the scene now, the purple earth mare seemingly striding in from nowhere. Despite being a deadbeat drunk, Berry tended to command a certain respect from her peers.
>”Sounds to me we have a mystery on our hooves.”
Lyra cautiously opened her mouth.
>”Um, Berry, I know we, uh, have hooves on our legs, but isn’t the colloquialism-”
>”PONIES EVOLVED FROM QUADRUPEDS, NO MATTER WHAT THE GOVERNMENT AND THEIR SO-CALLED SCIENTISTS SAY!”
Berry removed her hands from around Lyra’s throat.
>Now, as I was saying, we have a mystery. I’m guessing you guys want me to solve it?”
>”Preferably in a discreet manner.”
>”I don’t normally do ‘discreet’, but for you girls? Sure.”
So, the four began to plan their secret plan, to discover just what, was up with Derpy’s butt.
>”I gotta say Berry, you’re really nailing the whole conspiracy-mare thing. That costume just screams ‘the heliocentric model is reality’!”
>”What costume?”
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The plan was simple. Berry Punch would travel out of sight, following Derpy, Carrot Top, Lyra and Bon-Bon and using discrete methods to learn as much as she could about the grey pegasuses rear-end. It was a quick plan, but sure to be effective. As the four returned to the living room, they found their target sitting patiently. Berry froze, drawing in a sharp breath as she laid eyes on the immenseness of her friend. As a result of this awkward breath, Berry began coughing.
>”Hi guys! Hi Berry! I saw you sleepwalk down the hallway! Are you alright?”
>”*cough cough*... Just peachy!”
At least it would be easier to fake being sick now.
>”You girls were in the bathroom for a loooong time, and it’s almost time for the festival to start!”
>”I know Derpy. C’mon, let’s get going. I can’t wait to bob for apples.”
>”I’m gonna win a spider plush!”
>”I’m gonna stay here. I’m not feeling well.”
>”Aww, that’s a shame. Oh! Time to leave! See you later Berry!”
Derpy and co. left Carrot Top’s a good twenty minutes early, most of which was dedicated to squeezing through the door. Nevertheless, the group was in high spirits, giggling excitedly, sharing stories of what they hoped to do over the night and all the while clutching their pumpkin-themed goodie baskets as they hopped down the street. Meanwhile, Berry Punch peered through binoculars, hidden within a bush. She would find out the secret behind the ass, or die trying.
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The first diversion to catch the eye of the group was bobbing for apples. Other, more modern attractions tended to draw the numerous colts and fillies away from it. The line consisted of mostly middle-aged ponies who were out for some dumb fun, so it was rather short in comparison. As the group neared the front of the line, Carrot Top volunteered to go first. As she stepped up to the washbasin, she deftly leaned in and plucked an apple out. Next up was Lyra, who somehow managed to impale an apple on her horn, which she tried to pass off as intentional. After a quick giggle fit, Bon-Bon took her turn. She had some difficulty, but was able to snag an apple nonetheless.
Finally, it was Derpy’s turn. The speechless stallion who was running the stand backed away nervously as she wobbled her way to the washbasin. Heads turned, drawing an audience as she prepared herself, removing the cardboard horn from her head, as to not ruin it in the water. Finally, after noting the positions of the few remaining apples, Derpy Hooves took a deep breath, and-
>”Sweet Celestia…”
Derpy bent over.
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While normally a pony would only bend over slightly to bob for apples, Derpy’s case was a little different. Her height meant she had to bend over even further, letting out a drawn out squeak as her panties were stretched thin around her gargantuan hips, pussy exposed to all who chose to look. As everypony watched, eyes and mouths wide, they realized that the grey pegasus’s face had been in the water for quite some time without coming out for air. Ironically, the spectators failed to realize that they hadn’t been breathing either. A few were beginning to turn blue, but fortunately what happened next managed to snap everypony back to reality.
Something whizzed through the air, striking Derpy’s left asscheek. Surprised by this, Derpy practically exploded from the water, dampening passerby with a tiny splash. Confused and gasping for air, Derpy promptly lost her balance and tumbled into the basin, while inside a nearby bush, a snickering purple earth pony set aside her slingshot and pulled out a pad of paper.
>”Buoyancy: Very Buoyant. Visual of impact shows that projectile caused a sizable dent in the material but was quickly bounced in the opposite direction, suggesting an elastic or spongy composition.”
Berry Punch quickly pocketed the notepad and peered through her binoculars at the scene. Her friends had helped Derpy out of the basin, and the stallion who ran the stand had passed out some towels, presumably kept on hand in case such an event happened.
>”Sorry about that Derpy, but sometimes sacrifices must be made in pursuit of the truth.”
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Thankfully Derpy’s costume was mostly waterproof and shed the water easily, however getting the Derpster dry herself was quite an undertaking, due to the “enhanced area” if you catch my drift. Fortunately getting her dry didn’t turn out too awkwardly, as her friends mostly kept their eyes shut and Derpy was a little too chilly to get aroused from all the touching. The group then decided that it would be best if they participated in the costume contest before their getups were ruined by similar accidents or, heaven forbid, Rainbow Dash. As they began their journey to the community center, idle chat ensued.
>”Thanks for helping me out back there girls. I don’t know what happened, but it kinda felt like a bee stung me, and I just fell over!”
Lyra coughed.
>”Well, I don’t know either, but last I saw, there was no sting on- uh, back there. Honestly I didn’t quite catch what went down at all, it just went by so quickly.
Carrot Top cut in.
>”To be fair Derpy, you were leaning over quite a bit. That probably didn’t help things.”
>”Yeah! And, uh, isn’t it a little awkward to, y’know, be a few heads taller than normal?”
>”Um, I guess it’s a little weird, but it’s for the costumes sake. I really wanna win the contest this year.”
Bon-Bon, Lyra and Carrot Top hearts stopped. Each taking a slow, shaky breath, they slowed their pace and slipped behind the grey pegasus’s behind. They began to whisper, voices laden with panic.
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>”Oh no.”
>”She’s actually competing this year!? She usually just watches!”
>”Princess Luna herself is judging the costume contest this year! She’ll flip if she sees that costume!”
>”She’s gonna kill her!”
>”Worse, if Luna sees us with her, she’ll think we’re in on it and kill us too!”
>”I don’t wanna die!”
>”We need to get out of here.”
>”We can’t abandon Derpy though! If we do, it’ll be really super awkward for everypony.”
The group silently agreed that social awkwardness was a fate worse than death.
>”We compromise then. If everything starts going wrong, we skip town.
A quick nod from everypony present, and the group hastened their pace towards the Ponyville Community Center. Berry Punch trailed along, deciding to wait outside the community center. It would be too busy inside and she would likely be caught snooping around.
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>”Uuugh…”
I was bored. Pony after pony piled into the auditorium, all vying for my attention and, obviously, the trophy.
I’ve seen it pop up on E-neigh a couple times. How that hunk of molded plastic manages to get bids in the thousands still eludes me. Nevertheless, the look of achievement on a pony’s face when I handed it to them was priceless.
Oh hey, there’s a creative one! Of course, I’ve seen it before over the years, but it’s nice to see a pony think they’ve done something truly unique.
My heart sinks a little as I see a bunch of ponies wearing the exact same store-bought costume enter the building. I can practically write off who’s not winning the second they walk through the door, and I find myself mumbling into my arms.
>”Store-bought. Nope.”
>”Store-bought. Nope.”
>”Store-bought. Nope.”
>”Ooh, that one’s nice.”
>”Store-bought. Nope.”
>”Oh hi Twilight Sparkle. Guess what? You lose.”
>”Store-bought. Nope.”
>”Store-bough- wait, what?”
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I’m looking at the door, and all I can see is a huge grey blob shoved halfway through the door. The way it’s pulsing makes me think that somepony on the other side is trying to push it through. I have absolutely no idea what’s going on, but I’m at least interested.
Moments later, the grey thing slides through the door with a loud pop, and collapses on the floor, immediately followed by a couple of mares (Regrettably wearing store-bought costumes) who stumble and fall down. The ponies and the blob all rise to their hooves, clearly a little dizzy, but they soon catch sight of me behind the judge’s table, their eyes locking onto mine.
Except for the grey-blob. I’m fairly certain that one eye was focused elsewhere.
Hold on a moment, I recognize those eyes!
I’ve seen that pegasus before on Nightmare Night. She usually wore some sort of hastily made costume. I recall one year she wore nothing but paper bags. But, how she had changed! I’ve never seen a pony’s posterior reach such sizes in such short time! And her enormous bosom! If I were male I would envy her partner. She appears quite scantily clad, but legal, however I cannot quite place my finger on her costume...
I realize that I’ve been staring. The grey pegasus gets up and waves at me with a smile on her face before hopping on the stage and taking a (good deal of) space. The other three mares, on the other hand, look like they're about to die of a collective heart attack. A couple of helpful ponies managed to help them onto the stage.
Well, that was a little odd, but seeing that no other ponies are showing up, I suppose it’s time for me to judge these costumes.
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I’m looking over these costumes sequentially, but every time I try to pick out details or give a proper rating, I find myself thinking of or looking at the large grey pegasus. To be fair, she stands out the most, due to her size, but it’s getting in the way of the other contestants, so I decide to do her out of order. It’s a silent judgement, so nopony will know anyway.
 I start to analyze her costume. I’m mostly ignoring the drastic change in her proportions because I am here to judge costumes, not physique.
Hmm, overall it gives off quite a unique feeling. It doesn't have the “scare” factor present in many costumes, rather it seems welcoming, a degree of familiarity but also royalty, as evidenced by her golden regalia and fake hor-
I have a sneaking suspicion of what, or rather, who, her costume represents. I just need confirmation.
>”Could the grey pegasus contestant with the yellow-orange eyes please turn to the left?”
The mare in question did so, bumping aside a few nearby contestants. As expected, pasted over her massive flank was an image of a blazing sun, my sister’s cutiemark.
My eye twitched.
I could not ignore this. I stood up, and called out to the pony.
>”Please come with us.”
Ponies in the crowd began to murmur as she stepped down from the stage. The three mares that had come with her began to sweat bullets as I led their friend to the side room where I would address this issue. I shut the door and lock it, placing a silencing ward around the room. I don’t want the good ponies outside to hear this…
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>”AHAHAHAHAHAHAHAHAHAHAHA!”
Derpy didn’t exactly know what Princess Luna was doing, but the term “epileptic fit” came to mind. The Princess convulsed on the ground, kicking her hooves in the air and tears streaming down her cheeks, while she was consumed in bout of laughter. It looked like she was having trouble breathing…
>”Um, Princess? Are you-”
>”AHAHAHAHAHAHA! C-Celestiahaha! You have OBLITERATED your public image! HAHA!”
>”Um-”
>”We told you that ALL that CAKE would straight to your ASS but you kept on eating! Now they all see you like this!”
The Princess was going red with laughter, obviously out of breath, but she stood up anyway and trotted behind Derpy. Derpy gasped as she felt a pair of hands grasp her ass and squeeze.
>”HAHAHAHA! Oh-h sweet mother Faust, you even got the consistency right! I can’t believe it!”
A hearty slap to the colossal rump sent it jiggling wildly, along with a surprised squeal from Derpy and a slight blush. The Princess at least seemed to be calming down. She levitated a pair of chairs towards them and offered one to Derpy, who accepted and sat. Finally, Luna managed to clear the last of the giggles from her system and took a seat for herself.
>”Hehe, we are going to be absolutely clear with you; you are the winner of this years costume contest. Congratulations!”
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Derpy’s misaligned eyes lit up. She opened her mouth to cheer in joy, but she quickly caught herself. She was in front of THE Princess after all. Luna wasn’t done speaking though.
>”It’s been far too long since ponies have shown how they really think of my sister, and I thank you for pioneering this part of free speech that criticizes my sister’s unhealthy lifestyle in such a creative and humorous way. Hopefully this will get her eating properly again. Do you mind if we took a picture?”
Derpy nodded, and Luna quickly snapped a photo with a camera she had on hand for the occasion.
>”Now, about your trophy. Unfortunately, we cannot give you the trophy now, for various reasons. Ponies would begin to make jokes and rumors about ‘nepotism’ and ‘incest’ or even question our own sexuality! Can you imagine?”
Derpy couldn’t really imagine…
>”So here’s what we can do. We shall mail you a real trophy in secret, one made of gold from our own pockets and inscribed with your name, and I shall go back and judge a ‘winner’ from the ponies outside to receive the plastic trophy. Does this satisfy you, miss…?”
>”Hooves, Derpy Hooves! And yes it does!”
>”Excellent! Now, you should leave from the exit in this room and await your friends outside. If you were to return it might get awkward.”
With a nod, Derpy squeezed her way out, and Princess Luna returned to the stage.
>”Hoo, we haven’t laughed like that since- where is everypony?”
Not a single soul remained on the stage.
>”Curious…”
Outside, Derpy Hooves shook her head.
>”Well, It’s great that I won, but what was the Princess going on about with ‘free speech’? I just used a magazine for reference!”
END OF PART ONE