Derpy was a virgin. There’s no dancing around the issue, Derpy Hooves was (and always had been) a virgin. It wasn’t that she was an unattractive mare, quite the opposite actually. The pony had a cute face, one which could barely attract stallions’ attention away from her curvy, squishy and just overall thicc cheeks, thighs and teats.

The problem however was that most ponies weren’t exactly fond of her antics, and it was her clumsiness and overall ditziness that warded the other equines off.

Basically, in all of her life, Derpy had never gotten laid. Somehow though, that would change today. Yep, the events of the day ahead of her would change her sex life for the better, and soon she’d be getting to fuck ponies at any moments notice, only not in a way she’d ever imagined before…

In the present, before the incident that sets off the lewd chain of events to come, the mare is sat at her desk, scribbling one last document up before her last shift of the day ends. Trying her best to focus, she was failing miserably. No matter how her mouth tried to make the pencil travel over the delivery form, Derpy has been dying of boredom and impatience, it refusing to let her concentrate enough for this.

You see, as of recent she’d been getting sick of the job. It wasn’t her fault that she was so clumsy, and sometimes a few bits of mail just got destroyed on the job… or a couple dozen. Either way she was starting to grow weary of mailing stuff and the shouting of her boss because of yet another angry customer, so to fix the predicament, she took the day off of work tomorrow. Maybe it would help her clear her mind from everything, and though she highly doubted that, she wouldn’t let her optimism be quelled so-

SLAM! With a hoof smashing down on the table next to her, the poor mare launched out of her chair like a frightened cat, shrieking. Being thankful her wings would hold her in the air as she tried recovering from her heart racing, she didn’t need to check who it was, knowing precisely who always did that to her. “DERPY!”

Wonkily descending to the floor of the communal office, she peered up at him, shyly greeting who’d just nearly given her a heart attack. “H-H-Hey b-boss…” Embarrassed, her eyes couldn’t meet his, them trying to look anywhere else. It wasn’t that she was afraid of him, only that she feared for her salary that was desperately needed if she wanted to keep living in her small house, him controlling that.

“Were you daydreaming on the clock again?” He’d used this irritated voice on her more than he hadn’t so she probably should’ve been used to it by now, but still the unspoken threat of her losing her job hung in the air. It wasn’t that it was the best job ever, in fact she’d actually rather have a different job, but this was the only one that’d put up with her clumsiness, so she NEEDED it.

“N-No Sir.” It being a blatant lie she knew he wouldn’t believe, but she’d blurted it out before thinking about it.

“…Good.” Fortunately though the sisters were looking down on her and let her luck prevail, the stern stallion uncharacteristically ignoring the mare’s lack of productivity.

That probably means he wants something though… In the clear, Derpy dared to look up at him, not meeting his eyes again as she spotted a package in the hoof that hadn’t frightened her terribly. What’s that? It didn’t look like any other package she’d seen before, too fancy. Where’s that from? Who’s it to? What’s going to-

Frowning at the mare spacing-out again, her higher-up cleared his throat loudly, grabbing her attention to make sure she was listening. “This right here is an insanely important package, one that I wouldn’t trust you with in a million years.” His eyes narrowing, from the way he spoke it seemed like there was a ‘but’ in there. “But… I don’t know if you’ve noticed but all your coworkers have gone for the day.”

Glancing around the room, it was true, every desk was entirely unoccupied, something very unusual on a day like this, but not impossible.

Closing the distance between the two of them, pretty much glaring at her, he made sure to stress the importance of the parcel that she’d apparently be delivering. “This box right here is from Princess Celestia herself, it apparently being too fragile to just teleport over to Princess Twilight, so you’re going to be more careful with this than you ever have been with anything else. EVER. Got it?”

Despite nodding her head, she was confused. If it really was of utter importance and urgency then why wasn’t he taking it? Plus she still had paperwork to finish off. “Wh-Why aren’t you-“

“I would take it myself!” Cutting in, the look of frustration with her turned into one of nonchalance. “But I’m lazy. So you’re going to do this, and at least if it’s damaged you can take the fall instead of me.”

All of a sudden, the pressure piled onto Derpy. This was it, if she messed this up then she may never be able to find a job again. It wasn’t like she had to pay for much, living alone, but still this job paid for everything she owned. “I-I-I…” Internally panicking, frozen in place, another miracle happened as her mind granted her an excuse. “I-I have paperwork to finish up. S-Sorry, I would but-“

“I’ll do that for you then.” So much for that plan.

Backed into a corner, she just nodded helplessly. This would be tough, but if she really put her all into protecting this apparently fragile and unimaginably important cargo then maybe she could do it without a hitch! Determinedly, her hooves grasped both sides of the cardboard. With Derpy nodding to herself, the stallion gave her a grunt in affirmation before swiping the sheet she’d been writing on and leaving.

And so, confidently, Derpy flew out the offices and out the door, not letting anything take her attention off of the box that wasn’t of some vague danger to it.

C’mon, you’re Derpy Hooves, you can do this! Hyping herself up, it was a struggle to be so optimistic considering how much she’d screwed up this kind of thing in the past, but she couldn’t afford to mess up now, slowly letting her wings carry her directly over Ponyville and to the Crystal Castle.

Without letting the precious package and how much was riding on this escape her mind, the mare flapped her wings, letting them carry her over all sorts of buildings to reach her destination. But as she tried focusing on the task at hoof, her head kept demanding answers that she didn’t need. She really wanted to drown them out and stay on target, wanting to shake away the thoughts, but like usual, Derpy was unable to stop herself, peering down at the mysterious mail as her eyes glazed over, the mare spacing out without stopping her flight.

So much could be in there though… If one of the Royal Sisters is sending it to Twilight then it must be important or powerful or something… It was unlikely anything would bother her up here, but not impossible, and she wasn’t watching for anything around her, so if something were to catch her off guard then the consequences could be disastrous.

Beneath her, the ponies of the village saw her with the item, nothing new happening and nothing to attract any attention coming from Derpy.

But what if it’s some magical artefact for Twilight to use against any bad guys in the future?! Maybe… but it is fragile apparently. Ooh, what if it’s just some princess thing? Like something secret to only share between other royalty? That isn’t very specific though. If only there was some way of knowing…

She was lost in her head now, oblivious to everything, and especially oblivious to the imminent danger heading her way.

Idly holding the box as she stares down at it, trying aimlessly to figure out it’s mysteries, Derpy couldn’t have been prepared for-

Thud!

“Gah!” Snapping her head upwards to find out what in Equestria had just smashed into her face, the last thing the pegasus expected was more of them heading for her face, her and a flock of birds having collided and them refusing to stop for her. “Woooaaah!” The winged pests, as if in spite, weren’t going all the way around her. They slipped past her body for convenience, not just uncaringly obscuring her view with feathers but flying under and above her wings too, leaving the mare disoriented as she flailed to stay airborne. “No, no, no, no, no!”

With Derpy’s body spinning repeatedly, the nuisances had all passed her without bothering to look back, her taking the available chance to straighten herself out and get back to what she’d been doing, not before being mad at the rude avians though.

That’s just my luck though, isn’t it? The pony had always thought she was cursed or something, her luck being as good as her eyes were normal, but now isn’t the time to fret over any of that, she still had a job to do before she could chillax on her day off. Those damn birds! They nearly made me drop the-

She glimpsed at her hooves, freezing as her face displayed her shock at their emptiness.

WHAT?! But- Wha- How did I…? Her mind going into overdrive, Derpy thought on the spot, readjusting her body to look down and successfully spotting the cargo… falling straight to the ground beneath her after she must have dropped it. Fuck!

A little amazed at her own quick responses during her panicking, she acted before thinking, diving down to snatch the fragile box up before it hit the ground.

Shit, shit, shit, shit, shit! The wind blowing on her fur, Derpy Hooves didn’t stop swooping down, getting closer and closer to what she was supposed to be protecting. C’mooon! Just a little more! Grey hooves nearly clutched onto the box, but it slipped out of her grasp before she could hold it. This may be the fastest she’s ever flown with her truly putting her all into this, so her speed, leg control, balance and every other important thing are likely off, but still, she’s so close to it, all she has to do is-

SMASH! But her best wasn’t enough, and the box smashed open on the ground.

Pulling back at the last second, the momentum ended up being too much for Derpy, sending her flying down the dim alleyway that her and the now destroyed parcel landed in. Dust among other things, got kicked up everywhere as she ‘landed’, her round bouncy body bounding on the dry dirt floor before ending in an unflattering finish that surprisingly hadn’t caused her much if any harm. After stopping however she wasn’t focusing on the slight ache in her body, her mind stuck on the sight of the broken and unfixable mess of the package over there. N-No!

Glumly, she sauntered over to it, her world crashing down as she did so. This was it. Everything in her life had built up to this failure, and now she’d have to face whatever consequences the most powerful mares in Equestria would send her way.

Wh-What’s going to happen to me?! On the brink of hyperventilating, she started pacing around what so much of her life of normalcy depended on. Th-They could lock me a-away! O-Or banish me to some scary place outside of Equestria!! Or m-maybe even lock me up in the place they banished me!!! Stopping and taking deep breaths in an attempt to calm herself, Derpy felt queasy, but surprisingly it wasn’t the normal kind of queasiness that this level of stress would cause in a mare. “W-What?”

So much is happening to her right now that it threatens to overload her brain with it all. First the news of the vitally important parcel, then those birds and her clumsiness making her drop and break it, and now there’s some weird smell around her making her feel… weird.

What is that smell? The banishment and imprisonment and all that she’d put to the side for now, because of course something else had to show up to make life even harder for her. It smells kind of… nice though. Tilting her head down at what she assumed the attractive aroma must be coming from, she turned out to be right as it came from the princess’s delivery, the smell taking the form of a pink mist rising up from the box.

Upon realising that she’d just been inhaling… whatever that was, Derpy investigated it’s contents, baffled that she hadn’t already out of curiosity. Inside the wreckage lay two things: a shattered circular potion bottle, and a note.

I just breathed in a random potion! That explained the weird feeling she was having in her body, one that was only getting more powerful as time progressed. I-I know need to apologise to the princess sometime, but first… Using her wing to snatch the note from Celestia to Twilight, she got to reading it, hoping it would say what exactly the gaseous concoction held in store for her.

It read:

Dearest Twilight,

I hope you are well, though I’m afraid this package hasn’t been sent to you to simply say ‘hi’. What came with this letter should be a delicate potion that I happened upon in the deepest part of my and my sisters’ old castle. I believe it is from the rule of a former alicorn of Equestria known as Libdinia, the alicorn of lust. All we know of it as of now is that it has some powerful effect over the body as well as an equally powerful effect on mares around whoever the potion was used upon. If you could devote time into researching it posthaste that would be preferable.

I apologise for this but as we do not yet know of the powers of this potion I have preferred to put my most trusted researcher on it.

Sincerely, Princess Celestia.

Even Celestia didn’t know what the potion would do. Fantastic. B-But, what’s going to- “Hngh!” A jolt shooting through her body cut off her thought. A potion that would do some mysterious thing to her she expected to be painful, but this had felt… really good, pleasurable even. I-I need to get back home! The pink mist had entirely disappeared at this point, all of it either gone forever into the open air or inside of her, changing her.

It could do so many unknown things, at least if she was at home it could happen in a place of comfort and privacy, rather than an empty alleyway between two random ponies’ houses.

Deciding she could come back for what remained of the box, Derpy sprinted off hurriedly, ignoring the feelings inside of her. Zooming out of the alleyway, not trusting her wings to carry her the short distance from where she was to her house, the mare wanted to attract as little attention as possible, nopony finding out about her massive mistake. For some odd reason though, the little attention she wanted evaded her, and though it was quite a normal thing for her to be rushing through the streets, it felt like everypony she galloped near turned to look at her.

Surprisingly, Derpy didn’t think about that that much. Her mind being far too busy dealing with the bizarre sensations down at her nethers, it fuelling her rush to get back home. And after what felt like hours but was only minutes, the mare spied her front door, making a beeline for it.

Diving in, Derpy locked the door as she leaned her back against it, hiding from everypony’s stares as the feeling erupted in her once more. H-Holy shit! She needed to sit down or something, not wanting to deal with this here and craving some way to figure out what was happening to her marehood. Stumbling over to the living room on her four hooves, she was able to bring herself to close the curtains, before collapsing onto the sofa.

Sat upright whilst leaning back, Derpy looked down worriedly, the feeling was the strongest it had ever been, but it was only because her body was starting to change before her eyes.

Moving down her body, her medium-sized teats began changing both inside and out, the nipples disappearing as they moved between her vagina and her ponut. She wasn’t focusing on the ridiculous strangeness of that however, instead looking at how her pony pussy changed drastically too. The clit revealed itself from under her hood first, but from there it’s form began changing too, and growing, a lot. Under her, the mare’s tits had been forcibly transformed into a pair of hefty and furry testicles a darker grey than the rest of her body, them both already getting to producing plenty of cum for her to shoot out of what else was appearing.

Above the two grey balls, the vagina of the mare reconfigured into the sheath of a stallion, her new genitalia being so real-looking that it was as if she’d had them her whole life. But they were real, all of a sudden, Derpy had just gotten herself some new male body parts to replace her female ones, body parts that weren’t going anywhere.

And it still wasn’t over. Kept within her sheath she could feel something else, something ready to make it’s grand entrance.

Worming it’s way out of the sheath, what her clitoris had become showed up, the pink clit having turned into the pink-ish red-ish flared tip of her new massive horsecock. With Derpy moaning at the feeling of her flaccid dick sliding out of her sheath, it kept revealing itself to her in all it’s glory. Firstly was the head, but after that her thick, veiny shaft made itself known, the pink skin of it turning into a hot dark-grey as it kept coming out. “Ahn! S-Sweet Celestia!” Slipping out, her erection only stopped once, but kept pushing, squeezing the medial ring out for the first time and letting the other third of her new dick escape.

Only able to sit back and watch, Derpy marvelled at the glorious appendage that began hardening and twitching until it grew fully erect, finally having a better idea of what ‘effects’ the potion would have on a mare’s body. So huge, so girthy, and if what she was smelling was coming from that monster of a cock then it was so musky too!

It was quite the contrast to her round and rather pudgy figure, but how it looked on her was the last thing on Derpy’s mind, everything else being more important to her right now, like- “Wh-What the fuck?!”

Hesitating to move, any movement just making that beast throb more, she kept sitting there, staring at it.

I… I g-guess I have a dick now… Pulsating between her legs, bobbing up and down as blood rushed through her wood, it demanded satisfaction. She wanted to refuse the needy urges, ignoring what her new appendage wanted, but with it at full-mast, the huge horsecock was sending waves of arousal through her body, making it near-impossible.

Twitching, the monstrous appendage and its horniness kept not make this easy on her, sending vivid and lewd images of the mares she was surrounded with every day to her mind. She’d never thought about them that way, but now, now she couldn’t stop, the village’s mare’s beautiful bodies even making a little precum dribble from her tip.

Constantly, everything bombarded her. The arousal, the images, the throbbing need of the dick under her. And it was too much for her. Breaking from the need, you could see the exact moment her will shattered. Like lightning, Derpy’s front hooves shot down, slamming onto her medial ring as she got to sloppily jacking off, pumping up and down on her massive maredick. “O-OH MY GOSH!” She’d been refusing to touch the thing despite every inch of her body pleading, begging for her to give in to the lust, and now she had the euphoria of it was crashing through her, the pleasure immensely gratifying.

Derpy had masturbated before back when she had a pussy, but this felt infinitely better, even making her moan loudly to herself whilst she panted breathily.

So, sat on her juicy ass on the sofa, Derpy didn’t allow herself to even think of stopping, preparing to have the time of her life here. But she couldn’t masturbate without anything to jerk herself off to, and so she laid back as the dirty and kinky images swarmed in again. Going through the many mares of the village she knew, Derpy imagined them in all sorts of positions she found ridiculously sexy. Some on their back with their legs wide open. Some on their front with their ass up and their cheeks stretched open. And some only standing, but her imagining what the view from underneath would look like. “AAH!”

This must’ve been her dick’s doing! It making her libido and lust suddenly soar! She'd never had even dreamt of doing something like this or even imagining them in this way, she respected them all way too much to. But she didn’t care now, it felt too good. In the privacy of her home nopony would or could stop her anyway, so why should she even try to stop herself?

Up and down and up and down. Like a blur her hooves wouldn’t stop travelling, rubbing frustratedly on the skin of the phallus, unrelentingly sending unending pleasure through her loins and the rest of her body. The more and more she thought of the mares she was constantly surrounded with, the more and more the exhilarating yet unfamiliar feeling of an orgasm built up in her dick. And now she’d felt it, Derpy couldn’t resist hungering for that climactic orgasm.

Somehow, despite her new permanent toy desperately wanting to, she hadn’t imagined herself fucking any mares yet. It had been tough, but the mare could at least resist that much of its influence. Everything else wasn’t off-limits however, pussies, ponuts and other pony parts very vivid in her excitable mind, just as long as she didn’t let herself imagine that she could ever get involved with them. Especially not with this thing beneath her legs making her even odder than she was before.

“A-AAAHH! S-Sweet Celestia!” Bucking upwards into her hooves, it was here, the long-awaited and elusive feeling rising in her crotch. Closing her eyes while her hooves moved at unseeable speeds, Derpy only moaned, even when her climax was forced out of her. “Ngh! AAAAAAHHH!” At the top of her lungs, Derpy girlishly screamed out. When opening her eyes with her hooves still going at it, she saw the first rope of her cum shoot out from within her. Already, Just from that one strand of cum she could tell it was abnormally large, but that wasn’t all as another rope shot out, flying through the air majestically before splatting on her living room floor. And after that came another, and another, and another.

When the time finally came for her to rest after a minute of pure ecstasy, Derpy Hooves could only collapse fully onto her sofa. Her head dropped backwards and her limbs all limp as she panted hotly.

“Th-That was… That was amazing!” It was true, this thing gave her feelings she couldn’t get enough of. M-Maybe… Maybe getting this thing wasn’t such a bad thing to happen after all… There was certainly a bunch of complications to sort out, like how she’d hide it in public, but if she could masturbate now and really enjoy it now (the mares in her mind helping with that) then she’d be happy to keep this new thing and ‘tend to it’ whenever necessary.

It certainly seemed demanding, her now having an insatiable libido, but at least Derpy knew that she’d try her best to keep this to herself, the memorable mares of Ponyville continuing to take little interest in her and letting her remain a virgin, even with this colossal cock she has.

“Ngh!” At the thought of such beautiful and… alluring ponies, Derpy’s dong couldn’t help but twitch. It had never gone down even after splurting her load all over the room, and now it hungered for more, something she wasn’t entirely against. So breathing heavily, she gave in, and her hooves wrapped themselves around her length once again.

Author's Note

He’s starting another story! Who could’ve guessed?! Everyone who’s new to my stuff, just keep in mind that I am incredibly slow and incredibly inconsistent with my updates, so I don’t even know if I’ll ever even finish this fic… Sorry!

I’ve had an idea: at the ‘author’s notes’ of every chapter I’ma put a code for a smutty pony pic depending on who the chapter’s about (crediting the talented artists of course).

So #1: Derpy Hooves (futa edition)
2939223 by cold-blooded-twilight

And apparently there’s some actual Derpy lore involving Dinky and Dr Whooves, but I’ma just ignore that.

To finish, tell me what you think about this fic, I genuinely have no clue how it’s going to be received.