Double Booked

by Pillowfight

Rating: mature
Tags: Anon, My Little Pony: Friendship is Magic, Second Person, Alternate Universe, Romance, Porn, Sex, Comedy, Self Insert, Profanity, Derpy Hooves, Human
Length: 9113

An epic sexual duel between two reader insert characters, competing for the heart of the ultimate waifu... Derpy Hooves!

As the first human in Equestria, Anonymous enjoys a life of luxury and constant pleasure. Day and night, Twilight Sparkle’s virile and inexhaustable boytoy makes sweet love to her and her famous friends. It’s the best life you can possibly imagine...

Unfortunately, it’s not yours. You are the second human in Equestria.

As such, your task is to service Ponyville’s background ponies, the many mares who aren’t famous enough to warrant Anonymous’ amorous attention. It’s not so bad... after all, today you’re on your way to the home of Derpy Hooves, the cutest MILF in town. You’re looking forward to a memorable day of passion with the bounteous pegasus, but why has Anonymous started walking alongside you? He’s surely not going to Derpy’s house, too... is he?

Is he?

A silly comedy clopfic featuring meta humour, male jealousy, double penetration, massive mommy milkers, intense emotions, and a well deserved threeway for one needy mailmare.

Cover is by coldbloodedtwilight, 3218462 on derpi.

Published 2023-12-12 22:20:01 UTC
Last updated 2023-12-12 22:20:01 UTC

Double penetrated

“Ah, good morning, Mr. Human,” Mayor Mare smiled at you as you stumbled into her office. “I hope Roseluck let you get some sleep last night.”

“Roseluck was a perfect gentlemare,” you assured with a yawn, not wanting to speak ill of your latest lover. In truth, the flower pony’s caring facade had melted with a single glance into animalistic lust. As for “sleep,” it was a foreign concept at this point, a standin for whatever brief glimpses of the dream world you’d been able to grab as the cock thirsty Roseluck rooted her tiny pussy onto your crotch and rode you all night long. When it came time to make your daily report to the Mayor, only a double-triple espresso and a diabetes bomb of a Sugarcube Corner cinnamon roll had gotten your corpse moving once again towards Ponyville’s town hall.

“I hope you saved some energy for today’s assignment,” the Mayor stated with a wink, pushing the now familiar envelope over her desk towards you. “If you have anything left afterwards, why don’t you stop by my place tonight? I make a great risotto, and I’d love to show you how to ‘stuff the ballot box.’”

“It’s a date,” you agreed with a smile. Despite the exotic beauty and bubbling passion of every female you’d been “assigned to” so far, you’d found your mind occasionally wandering during your amorous adventures. It seemed that after a month of casual sex, you were starting to feel the need for emotional connection. An unplanned adventure, perhaps even a relationship with this sexy older mare... it could be just the thing to bring the pep back into your little soldier’s salutes.

On the surface, you lived a life many bronies would kill for. Whisked from a drab and meaningless existence in the real world, to the colourful land of Equestria... or at least one such land. This was a place much like the one seen in the cartoons you still secretly watched, yet with one not-so-minor exception: each and every mare here seemed to possess the beauty and grace of an equine supermodel, coupled with the body of a pornstar and the libido of a nymphomaniac!

The not so subtle difference between the Equestria you knew and this more ‘adult’ variant was quick to become obvious. You hadn’t been here for even 10 minutes before you were naked in Nurse Redheart’s examination room, sheathed deep in her clenching marehood while she called out your name and begged for your seed. Now that you’d settled in, it was rare that your cock went even one hour without an appreciative nuzzle or suck, each mare carefully cleaning the residue of your previous lover before adding a thin layer of her own saliva... and sometimes more!

Unfortunately, the ponies you most coveted, the Mane 6, were forever off limits to you. A few years before your arrival in Equestria, another reader insert character known only as “Anonymous” had preceded you. The other human had swiftly seduced Twilight Sparkle with his talented hands and totally not bigger than yours cock, and he’d spent the past several years in seventh heaven, destined to pleasure and pound the beautiful Elements of Harmony as they wailed and screamed with untold ecstasies.

Of course, the other mares of Ponyville had heard these echoing cries of joy, and grown most dissatisfied when Twilight refused to lend Anonymous out for the public’s amusement. Over the years, demand for big human cock had grown to a fever pitch, until Twilight had taken pity on her fellow ponies and summoned you from Earth. Now your daily task was to see to the needs of those mares who weren’t important enough to deserve Anonymous’ attentions... the background ponies, if you will.

You’d been adjusting to life in Equestria for a month, and in that time you’d given quite a few of Ponyville’s mares a hearty seeing to. You’d even made a trip to Manehattan to enjoy a sensuous romp with Saffron Masala and a private “fitting session” with Coco Pommell (she got it to fit, all right... right up her butt!)

It was all more enjoyable than your old life on Earth, and everypony seemed to be having fun. Married stallions like Mr. Cake happily opened their bedrooms to you, eager to sit beside the marriage bed and watch you plow their wives. Mothers and daughters stood plot by plot and lifted their tails in unison, turning what could have been a heated family rivalry into a wholesome bonding experience. Even couples like Vinyl and Octavia welcomed the occasional stiff prick into their bed, it seemed.

In this sunny land of friendship, only one cloud hovered on your horizon: that damned Anonymous, and his unlimited access to all that prime, main character pussy. Twilight’s royal lips, Fluttershy’s motorboatable teats, Applejack’s phat apple bottom, Pinkie Pie’s ginormous everything... why couldn’t it be yours? Why did you have to be the second human in Equestria? The intensity of your jealousy was enough to reduce your ramrod to a mere half chub... though a smile or a lick from a friendly mare soon stiffened it right back up!

As you left Ponyville’s town hall, you opened the envelope to learn of your “assignment” for today. Rather than writing down crass orders such as “pound Strawberry Sunrise til she squirts,” the Mayor preferred to discretely draw the cutie mark of your latest cutie on a small slip of paper, and let you deduce the rest. You smiled as you unfolded the sheet to see the picture you’d been hoping to witness for weeks: a line of bubbles seemingly rising up to heaven. These were the same bubbles you’d seen wobbling against the grey fur of a certain airborne dumptruck — the hottest ride in town!

Perhaps you’d never fulfill your fantasy of cumming inside Rainbow Dash, but Derpy Hooves was quite the consolation prize. You’d seen the mature pegasus hovering about recently, eyeing you up hungrily, eagerly awaiting her own turn with you. Now, today was the day you’d show her what human-style lovin’ was all about.

Ponyville was full of attractive older mares, but Derpy was a genuine, certified, foal bearing MILF — your favourite! You couldn’t stop from drooling as you pictured those perky nipples swelling under your fingers, that winking clit throbbing against your lips, that soft and motherly plot giving way to your penetrating prick, that cute face smiling up at you and ready for an application of freshly squirted cum!

You sighed with contentment as you practically skipped across Ponyville. Yes, let Anonymous hammer the same 6 pussies over and over until he grew bored... you lived the carefree life of a gigolo, with a different horse vagina slipped over your blissful meat each and every day! It didn’t even spoil your mood when you caught sight of Anonymous on the other side of street, cheerfully walking in the same direction as you were.

As Derpy lived not far from the Carousel Boutique, you surmised that Anon was headed off to enjoy some high fashion perversity with Rarity. You were so excited about finally plowing Derpy that you couldn’t even begrudge him his good fortune. You waved at your fellow human and smiled, which Anon unfortunately took as an invitation to cross the street, walk with you, and strike up a conversation.

“How’s life in paradise?” he asked with a grin. “Has the pussy gotten to ya yet?”

“Heh heh, some of the girls are pretty demanding, alright...” you admitted awkwardly.

“Fr, fr... but I can’t wait til Starlight Glimmer shows up! You know that crazy bitch gonna be freaky as hell!”

You silently grimaced as you listened to Anon’s entitled ramblings. This utter douche had no claim on Starlight! For one thing, the villainous unicorn had yet to make her debut in this world, making this a clear case of counting your horse-sluts before they’re hatched. Not only that, it ought to be your job to carnally “reform” Starlight, just as you’d done with the Wet and Satisfied (previously known as the Great and Powerful) Trixie.

The idea that Anonymous ought to be the one to break Starlight Glimmer’s ape cherry just because she eventually became a main character was beyond ludicrous! Yet if you brought the question to Twilight, you were certain she would inevitably side with her lover. Maybe you’d pay an early visit to Starlight’s creepy communist village, and get that evil cutie hooked on human dick, before Anon could get to her. Or perhaps that was a horrible idea...

At long last, you approached the street corner where Anonymous should have turned away to visit with Rarity. Yet Anon passed right by the intersection and continued to walk alongside you, chattering away about your shared interest in sexy equine bodies. You tried to think of a way to excuse yourself from this unwanted company... but before you knew it, the two of you were standing together on the very welcome mat of Derpy’s humble cottage!

As you reached to knock on the door, Anon put a friendly hand on your shoulder. “Thanks for walking me to Derpy’s house, friend,” he smiled, “but I’ve got it from here. Run along and make out with that dentist chick, or whoever the mayor sent you to give a pity fuck today. I don’t want to make you look bad in front of my shmoopy muffin.”

“Huh? Back off, pal! Derpy is mine today!” you fumed.

“You? No way! Derpy’s a classy lady and she deserves the main character treatment. By which I mean, it’s her turn to ride the big green monster!” The strangely coloured human gestured at the already visible bulge in his crotch.

“The mayor personally told me to come here and show Derpy the time of her life!” You took out the small slip of paper with your instructions for the day and held it out triumphantly — your ticket to the three holes of heaven that awaited you behind that door.

“Are you sure it wasn’t some other piece of ass?” Anon squinted at the slip of paper and turned it upside down. “Yeah, t-that doesn’t look like Derpy’s cutie mark,” he lied. “It’s sweet that you care about her, my guy, but the Derpster is a fan favourite and she deserves the best sex possible. She’s the symbol of the entire MLP fandom, and that makes her my responsibility!”

“Derpy’s in, like, two episodes! She’s totally a background pony! You just want that ass!”

“Can you blame me?” Anon countered. “It’s the biggest in town! It canonically crushed a building! Just think of what it’ll do to me...” he drooled.

“She’s a joke character! Hasbro can’t even decide on her name!”

“That’s why I’ll simply be calling her ‘Mommy...’” Anon smiled dreamily.

As you bickered, you heard the door before you creak open. Through the crack, looking up at you, you beheld the heavenly sight of Derpy Hooves herself! Your heart skipped a beat at the beautiful if unkempt mare, her plentiful form wrapped in a fluffy robe. She yawned and scowled at the world outside her home, rubbing her sleepy eyes with a perfectly formed hoof.

“Hey, what’s all the noise?” she muttered before catching sight of you and Anonymous. “This is my day off—whoa! Two humans? Did I win the lottery?”

Anon immediately dropped to his knees before the confused pegasus and swept off his fedora. “I’m sorry, my Queen, but this lesser male insists that he has the right to pleasure you. I’m afraid he won’t leave until you reject him personally.”

“Derpy, explain to this idiot that you barely ever have any lines and you only exist because of an animation error!”

“How dare you speak to my waifu with that tone!” Anon slapped your face with a glove. “I demand satisfaction — pistols at dawn, sir!”

“Hrm...” Derpy put a hoof to her chin and looked back and forth between you and Anonymous as you bitched and fought over her. At last she shrugged. “Well, I do like ’em full of testosterone.” The mailmare grabbed Anon’s belt buckle in her mouth and yanked him through her door, then gestured at you with her wing. “Get in here, STUD!” she demanded.

You instantly obeyed, of course! As the door slammed shut behind you, Derpy gave the two of you a lustful smile and growled hungrily. Behind closed doors, it seemed that her true inner self could be revealed — not the cheerful klutz known to all of Ponyville, or even the caring mother her daughter saw, but a sexually ravenous mare in heat!

“Drop those pants, boys,” Derpy demanded. As Anon’s hands fumbled with his belt, her mouth went to your crotch and her powerful teeth firmly snipped off the button of your jeans. She spat out the tiny brass disc before skilfully lowering your fly with her lips. “I don’t care about your little rivalry,” she explained. “Just give me those hard, beefy human fucksticks, and we’ll get along just fine.”

“Y-yes, mommy!” Anonymous assented.

“Of course, Derpy, anything for your pleasure,” you agreed suavely. You caught Anonymous’ eye and the two of you exchanged a knowing glance. It was time to put your competitive natures aside for the greater good — the enjoyment of one Muffins “Derpy” Hooves! You’d fight it out on the amorous battlefield of her beautiful body, leaving it up to her to decide which of you was the better lover.

You had it in the bag, of course, as you’d indulged a far wider variety of mareish fantasies than Anonymous had. When it came to busty MILFs with fat plots, you doubted Anon had brought even one to a squirting, adulterous climax! His obsession with those young and vivacious main characters was sure to be his downfall, now that he was faced with the sophisticated lust of a mature and experienced mare!

Two fat, swollen human cocks reported for duty, bobbing up as you and Anonymous pulled your briefs down in unison, their mushroom-like heads bouncing against Derpy’s muzzle. Like two friendly dogs licking her face, your dicks spat out droplets of pre to cover Derpy’s lips with shiny gloss. Her nostrils flared wide and a stiff wingboner popped into existence as she took a sniff of your combined masculine power.

“Oh, golly, they’re so BIG, and they stink like sex! Human dicks are so powerful... I just want to be the naughty mare who licks them clean! Mmm..” Hungrily, Derpy did just that, dragging her tongue up the underside of your cock with a moan, then twirling the fat and sloppy oral digit upon the head of Anon’s huge and purple prick-head. As Derpy slurped and teased, treating your manhoods like delicious lollipops, her tail slowly flagged over the twin moons of her ass, unmuffling the constant sounds of her squishy winks, and revealing an earthy scent not unlike the one your own members were giving off!

As horny as Derpy clearly was, these signs of arousal were merely a reflection of the burning desire you and Anonymous had begun to feel for her. Once raised, this primitive lust was not something that a human could control, nor that a mare could resist. As visitors to this peaceful land from a more violent world, you and Anon were distinctly out of place: as tall as any alicorn, and stronger than the most musclebound stallion. If you truly wished to take charge of a sexual encounter, no other outcome could be foreseen.

Of course, Equestria’s mares had nothing to fear from you, as you always let your partners set the mood and the pace. If the situation called for it, you would even act innocent and shy. Many days you blushed as an aggressive mare took the lead and “seduced” you, overpowering your flimsy and false objections with the force of love and friendship, until she had your cock buried down her throat and her chin nestled between your balls. Ponyville was home to many demure mares as well, tender souls who needed many sweet words and gentle touches to feel comfortable with such an alien coupling.

Yet there sometimes came a mare who with shameful glances, sly hints and unbridled pheromones, conveyed a need for a more primal treatment. It was then that you would unleash the beast within, using the full measure of your human strength to pry apart her hind legs and pin her body to the nearest mattress. Heedless of your size difference, you would forcefully claim her, over and over, till she was fully satisfied. Though this treatment was rough and punishing, mild smiles always prevailed when the manhandled mare finally fell asleep next to you, each of her holes contemplating a satisfying dose of human sperm.

How strange, then, that although Derpy was one of the most forward lovers you’d ever had, your lust for her was boiling over, and causing you to respond like a mindless beast! By rights you ought to be submitting to her wishes, yet instead you felt a surge of feral power with every teasing lick and kiss she left on her prick! You HAD to have Derpy, and it had to happen your way!

A clench of Anonymous’ teeth and a burning in his eyes showed that your companion felt the same way. With a shared and silent nod, you and Anon reached down, GRABBED Derpy Hooves in your powerful human hands, and hoisted her up in a parody of pegasus flight! Her wings outflung, she cried out with surprise as the two of you lifted her up above your heads, firmly gripping her by the barrel.

“EEEP! G-guys, what are you — OH, WOW!”

As much as Derpy craved your dongs, you and your fellow male desired the taste of her sopping mareholes even more... and it was two against one! The middle aged pegasus didn’t stand a chance against two young and virile human studs! Her ass cheeks clapped noisily, her hanging teats swayed and slapped against each other, as the two of you dove in and prepared to feast upon pony-holes!

You lifted your chin and pressed your lips against Derpy’s already dribbling mare pussy, licking up the heavenly juices and probing for more with a greedy tongue. Diligently you worked yourself deep into the warm and welcoming cunny, even as your face motorboated Derpy’s hefty teats and your upper lip stroked her clit. Meanwhile Anonymous buried his face deep between bubbly ass cheeks and gobbled the mailmare’s ponut, licking and slurping at the sweaty treat like there was no tomorrow. “Mmm, so salty and tangy...” he moaned.

“So juicy and sweet...” you countered.

Derpy was simply overwhelmed by the sensations in her well endowed lower half. “Oh, my goodness... all the young stallions really do love eating ass! I thought it was only a meme!” She flapped her wings, trying to escape this double pleasure, but you and Anonymous simply stood on tiptoes as she rose into the air, gripping tightly onto her broad hips and keeping your lips firmly sealed to her eagerly throbbing pleasure portals.

Derpy’s eyes rolled about in her head like two wheels on a slot machine about to land on a jackpot of pleasure. Every feather on her body trembled and every hair of her fur coat stood up on end. “P-please, guys, you don’t know what you’re doing to me... oh, gosh... how you’re making me feel... I’M C-CUMMING!”

This confession of pleasure was exactly what you and Anon wanted to hear! You grinned as Derpy’s vag clenched up, then relaxed and released, sending squirting juices to soak your face and fill your mouth with sweetness. Anonymous moaned as Derpy’s ponut clenched tightly round his tongue. You kept pressing your tongue fiercely into the inner core of the climaxing mare, until Derpy went limp in your arms and giggled happily.

“Oh, boys, that was so good...” she muttered. “Ooh, such a naughty tongue up my booty, and you on my clit...”

Her wings fluttering, the satisfied pegasus slowly slid down between your sweaty chests, overwhelmed by the aftermath of her pleasure. Little did she know that poking up to “greet” her were two stiff and sturdy human dicks! She startled as her large clit slid down the wide cliff face of your glans. Then she grinned dizzily and with an instinctive hitch of her hips, she slipped your tip between her squirming and drooling lips. With a hungry sigh she continued her sliding motion, even as Anonymous’ large flare prodded her ponut and made her gasp.

“Oh, gosh...” Derpy muttered to herself. “I’m really doing it! It’s really happening! Two at once!” The head of your cock slowly spread her open, making way for the thick shaft that followed. Meanwhile, Anon’s dick pressed into Derpy’s forbidden tailhole, stretching it wide and adjusting it to its new purpose. Derpy’s breath became slow and heavy, yet she never slowed her descent or asked to stop.

“Ummmph... two stallions... two cocks at the same time!” she moaned out. “It feels SO GOOD!”

“D-Derpy...” Anonymous gasped with agreement.

“So good, Derpy!” you echoed.

Down and further down she went, her fur brushing against you excitingly, her cunt and ass slowly gobbling up inch after inch of your proffered cocks. Your endowments were far superior to whatever inconsiderate stallionhood had burdened Derpy with a filly: just large enough to pleasantly clog a mare’s holes without inflicting pain. Derpy couldn’t fathom a reason not to continue her descent until she was completely full of dick. She deserved pleasure, and fat human dicks provided it — you didn’t have to be an egghead to solve that equation!

At last Derpy reached the base of your stiff pricks. Anon’s cock pushed deep into her bowels, pressing gently against you through her body. You felt the taut fleshy ring of Derpy’s cervix contract and wrap about your shaft, clenching gently as if nursing upon your head. For a human woman, such deep penetration would be painful. Yet for a tiny horse, the feeling of being completely filled was pleasurable in the extreme, a herald of breeding and a guaranteed maregasm in the making!

“Guys... I’m so full... oh, I want to fuck, I NEED to fuck them, it feels SO GOOD!” Though a younger mare would have been overwhelmed by this double sensation in her lower holes, Derpy Hooves now flung her front hooves around your shoulders and began riding you! Slowly, yet powerfully, up and down her vast hips worked. She impaled herself on your upturned prongs, expertly twisting to vary the angle and the pressure of her penetration with every downward thrust. She knew her own needs so well, you would have thought she spent all day mounted upon human cock, working herself to one climax after another. At any rate, it was a sensation you would happily offer her!

As Derpy’s cunt stroked you off with its tightness and heat, you began to feel a pounding in your heart to match the throbbing of your taut and ready balls. The tight hug of her front hooves about your shoulders was a taste of heaven that brought to mind not your recent weeks of kinky, attachment-free sex, but your plan for a romantic date tonight with the lovely Mayor Mare. You were DP-ing a slutty pegasus alongside your most hated rival — why did this somehow feel wholesome? Your answer came, and your doubts and misgivings dwindled to nothing in an instant, when with half closed eyes Derpy pressed her lips forward and KISSED YOU!

Hearts exploded in your mind as your entire world seemingly turned upside down. Most mares wouldn’t kiss you at all, regarding you solely as a toy to relieve their heats. Your more submissive partners offered their lips, but often bared their necks as well, in the hopes that you would indulge a strangely common “prey” fetish. This was a kink you always made sure to satisfy, with nips from your teeth and snarled promises to “gobble up little ponies like you.” Yet kisses offered in this spirit were mere signs of submission. In all of your time here, only Derpy seemed to understand the true value of a meeting of the lips.

From what lucky teacher had she learned such romantic secrets? In your lonely years on Earth you’d never felt such hunger, such passion. Even as her lower holes were being brutally destroyed by the frantic motion of her own hips, Derpy was capable of showing incredible sweetness and tenderness. Those soft lips were Equestria’s secret weapon, capable of converting the most evil villain into a shy and smitten lover! The effects on you were immediate, the fires of lust searing through your body and revealing the sensitive emotions you’d hidden beneath a cynical and callous exterior. After a month of the most casual horsefucking possible, you’d finally met your match, and fallen in love!

Your dick throbbed and you gripped Derpy’s broad hips, thrusting up into her as your tongues touched playfully. Her pussy was claimed as yours, her womb was your cockhead’s private residence. She spoke between shudders and moans, and you fantasized that the pleasure in her voice was all because of you.

“Oh, the girth... just one of you is thicker than any pony! This is AMAZING! I... only... ever... want HUMAN COCK!”

Such opinions from “converted” mares were common, and once upon a time they had swelled your ego, but now these same words rang hollow. You wanted to hear Derpy praise your personality, not your dick! To fuck her daily, hourly, was merely one part of the togetherness you wanted to feel with her. What about candlelit dinners, evenings spent cuddling on the porch, or the simple ritual of decorating the Hearths Warming tree?

You had to win Derpy’s heart! Yet you were no poet who could woo her with words, nor some wealthy merchant who could bring prosperity to her broken family. The only tools you had to earn this lovely lady’s love were your huge human shlong, and the billions of love letters swimming in your balls, each personally addressed to one of Derpy’s eggs. It would have to be enough!

“Oh, fuck,” Anon groaned as his passion broke. “I-I can’t last much longer! Tight, hot pegasus pooper — my one weakness!”

“Yeah, gimme, gimme, I need it,” Derpy moaned, the churning of her hips growing ever faster and deeper. “Please, boys, cum inside me... make me feel all warm and juicy! Give Derpy your seed, she knows what to do with it, just, please, CUM IN ME!”

Now entering the final stretch, you and Anonymous alternated pistoning into Derpy’s holes, deep dicking her until the three of you climaxed simultaneously. Crying out her name in unison, you and Anon jetted thick ropes of semen into Derpy’s eager body as she sprayed the fluids of her passion down your thighs. It was the nut of a lifetime, your balls clenching so hard you thought they might burst. Derpy’s womb clenched down on your dick, hard, trying to pull out every droplet of cum you had to offer. Anonymous cried out with half pleasure, half pain, as Derpy’s almighty plot claimed yet another victim.

At last Derpy smiled and lay her head down on your shoulder, drooling somewhat, yet still intensely sexy and desirable. The fire in her mismatched eyes died down to embers, without going out entirely. For one moment, this heaven sent mare was was content. From your experience with mares you knew that before too long would come a time to fuck again. Yet for now the afterglow reigned, a time for checking in and hydrating, refreshing body and mind while sharing sweet words of affection.

This was your time to strike, as Derpy silently cuddled you, suspended upon your dick. You and Anon had conquered her body, but the true prize remained up for grabs: her sweet and pure heart! As much as it pained you to betray a worthy adversary such as Anonymous, there could be only one winner in this competition. Lies, foul play, even wedgies... all of it was fair game. You lived by a code of honour, true, but that once respectable code had shrunk to one single principle:

Derpy Hooves would be yours!

Double trouble

Gasping for breath, Derpy Hooves finally slid down off of your dicks and slumped onto the floor, leaking seed from her swollen and well used holes. Freed from her two velvet dickholsters, you and Anonymous swiftly collapsed on Derpy’s couch. You lovingly looked down at the chubby sexpot as your juice covered member slowly softened.

Your mind worked frantically, seeking to take advantage of these few precious moments when Anon was exhausted and not a threat to your plans. What could you do to win Derpy’s love? How could you consign your fellow human to the status of a long forgotten fling? The mayor had assigned you as Derpy’s plaything only for the day, but if you proved yourself a better lover than your rival, she’d surely pick you as her boyfriend! You tried to stand up, to sweep Derpy off her hooves with a romantic gesture, yet your body was so fully drained by the vacuum strength of her pussy that you could barely budge from the cushion!

“Oh, gosh!” As she saw the two of you, quivering and tired, Derpy’s maternal instincts rose to the fore. “You two look pooped out... I guess I don’t know my own strength! How about a little lunch for my hard working stallions?” You and Anonymous muttered incoherently, yet agreeably. “Yes, I know just the thing...” she assured you.

Derpy trotted to the entrance to her small kitchen and pulled down a cute, floral apron from a hook. Easily lifting it over her neck, she then reached back with her wings and tried to tie the string around her pudgy waist. Yet she was foiled in this simple domestic task by the vast thiccness of her plot, not to mention those fat and heavy crotchboobs between her hind legs. The two largest teats in Ponyville swayed gently yet forcefully against the fabric of Derpy’s apron, making it a near impossible task to bring the two strings together behind her. Even Fluttershy or Pinkie Pie would have had no trouble donning this apron... well endowed as they were, their young bodies were immature twigs compared to the fertility goddess before you!

“Oh, darn these big ole things!” Derpy cursed mildly. “They’re always in the way!” The mega MILF turned to face you, her titties clearly visible spilling out past the sides of her apron. “C-can one of you please tie me up?” she asked with a blush, aware of her double-entendre only as she spoke the kinky words.

For a fraction of a second your brilliant mind planned to seize upon this opportunity as a chance to prove yourself a better and more helpful lover than Anonymous. Yet all such scheming thoughts were soon crushed by the overwhelming femininity of Derpy in this simple housewife’s attire: an apron which protected practically nothing, and only called attention to the oversized rack that overflowed it!

“M-mommy...” you moaned, your eyes glued to the grey expanse of tit before you.

“Mommy milkers...” Anon added thoughtfully.

“Big creamy mommy milkers!” you cried out in unison. Far from being able to assist with this simple household task, your attitudes now seemed to have regressed to adolescence, if not earlier. Your minds half gone, half crazed with tit lust, you crawled like needy foals across the carpet. Each of you ducked beneath Derpy’s apron, latched on to a massive crotchtit with your lips, and began to gently suckle to restore your strength.

Derpy blushed a deep red at the arousing sensations surrounding her sensitive nipples and diving deep into her stacked body. “Oh, geeze, you humans really seem to like big titties, huh? The other fillies used to tease me, I was always the bustiest girl in school... but look at me now!”

“Nonny nurse on mommy milkers...” Anonymous murmured reassuringly, his lips smacking against a fat nipple.

“Yummy nummy mummy titty...” you muttered, your mouth tingling as you took deep pulls of Derpy’s sweetly scented titflesh.

“Oooh, that feels so nice... I suppose lunch can wait!” Derpy flapped back over to the living room couch, dragging the two of you behind her with your lips firmly attached to her nipples. She lay on her back and spread her hind legs to let her teats wobble and sag beneath her now useless apron, her jubblies nearly touching the ground and very much within your reach. “Keep going, guys, who knows, you may even find some milk in there...”

The truth was that Derpy’s teats had long run dry of milk, yet you found suckling upon her to be a peaceful experience. As you knelt on the living room floor, happily nursing next to Anonymous, you began to regard your fellow human not as a rival for Derpy’s heart, but as a brother, weaned like you upon heavenly pega-titty and very much obedient to your loving pony mommy.

“Oh... oh, goodness...” Derpy lay back on her couch and gently stroked the backs of your heads with her wings, moaning quietly. At last she shifted and spoke. “Boys, I hate to stop you, having my boobies sucked feels really good, but could you... maybe... pay any attention at all to my pussy?”

You felt a sharp pain in your skull as your head collided with Anon’s, so eager were the two of you to instantly obey. Derpy’s suggestion had the force of strictest command — so irresistible that both of you had moved to pleasure the mare’s foal-hole the instant she hinted you were neglecting it!

“No, after you,” Anon told you, gesturing at the treasure hidden beneath Derpy’s heavy hangers.

“Please, I insist,” you returned gallantly. “I’ve already tasted this heaven.” Also I just came in there, you added mentally. You used both hands to hoist up Derpy’s massive crotchrack, exposing her leaking and well fucked marehood to Anonymous’ drooling gaze. Eagerly, he dove in and began to lick and kiss between Derpy’s chubby thighs.

“Oooh, such a sweet boy. Now, if you wouldn’t mind—eep! Yes, that’s it! Two sweet boys...” Gently biting one of Derpy’s nipples, you resumed your worship of her motherly attributes, squeezing her teat flesh as you nibbled and suckled. Derpy’s already heavenly smile broadened to an ahegao look of pleasure as you and Anonymous worked together to serve her.

“Mmm, yeah, this is so horny... I feel pampered, like a Queen on a throne! Whenever you guys can get hard again, I’d—ooh, you were already hard!”

Indeed, the moment Derpy expressed an interest in a fresh round of penetration, you and Anonymous leaped up as one, displaying your stiff and throbbing cocks, once again leaking fountains of precum and ready for mare-pleasure. “Mmm...” Derpy licked her lips and rolled onto her side, wiggling her plot seductively. “Take me, I’m yours!” she declared.

“Let’s switch holes!” Anon suggested. He dropped onto the couch and pulled Derpy up on his lap, passionately kissing her as she wiggled her crotch down onto his shaft. You tried to object, but Derpy’s opinion of a cuntful of man cock was immediate and loudly voiced.

“Oh, it’s so THICK! SO big... so good... but I-I need another one! I need you both inside me!” Derpy tried to reach back with her wings and spread her hefty rump cheeks, but her ass was so dummy thicc that she could do little more than press soft feathers into plentiful ass meat. That pudge just wouldn’t budge!

“Please, my cute studly humans — unnnghhh! I— can’t—” The only way to shift those massive buns was to shake them, so shake the frustrated MILF did! Anonymous writhed helplessly beneath the weight of the tiny, bottom heavy pegasus as she twerked at you, grinding herself deep into his lap with every wiggle of her hips.

As alluring as you found the sight of those clapping cheeks, you somehow resisted the urge to dive in. The crack of Derpy’s phat ass seemed a hazardous place to be. Any man who tried to step in to the midst of this whirlwind of plot would find his two hips wrenched in opposite directions, and his pelvis suffering a fate like the roof of Ponyville’s town hall!

It was Anonymous who came to your rescue, providing a path forward. The other human reached, reached, reached forward to grab hold of Derpy’s cutie marks. His fingers digging deep into the jiggling wall of flesh, he held her dangerous hips steady while spreading her chonky cheeks for you. The musky canyon before you slowly widened, its walls quivering mightily yet no longer a bone crushing threat. Like a pot of gold at the end of a rainbow, Derpy’s grey ponut winked naughtily from deep within her buns, eagerly inviting you inside.

“Here you go, dude,” Anon stated helpfully, even as he hungrily groped Derpy’s well padded plot. Though cooperative on the surface, you still considered each other competitors, and the reason he’d volunteered to help you out was all too clear. This was a prime opportunity to maul some MILF ass without getting slapped for his insolence!

“Thanks, man,” you responded, taking your cock in hand and venturing deep into grey furred crack. Winning Derpy’s heart would require that you eventually betray Anonymous, leaving him disgraced in your lover’s eyes... but for now, there was pony plot to be pounded! You pressed the mushroom head of your cock into Derpy’s cum dripping dumper, causing a noticeable and immediate effect in the mare whose bum you craved!

“Ooh, it’s in my BUTT! The flare’s so big... it’s in my butt and it’s HUGE!” Derpy let loose a long stream of juice all over her couch and Anon’s bare thighs as she clenched and quivered in silent maregasm, just from being double stuffed once again. “I feel like it’s my first time, all over again... fuck me, boys, and make me feel young!”

As the man on top, you set the pace of this second round, thrusting furiously into Derpy’s ass, cramming your dick in to the very root and letting her grind her crotch up and down on Anon’s filling meat. A surge of jealousy filled you as you watched Derpy kissing Anonymous with just as much love as she’d shown when making out with you... yet who were you to deny or judge the brightest star in Ponyville’s galaxy of beautiful females?

After all, Derpy had just accepted you into the most private part of her body, without a second thought. She was free spirited and giving, and if she wanted to smooch other guys, that was just something you’d have to negotiate once the two of you were married. Perhaps you would even allow your defeated rival Anonymous to drop by your house for a friendly game of tonsil hockey. Only on Derpy’s birthday, and other special occasions, of course!

In the meantime, Derpy’s ponut was everything you’d dreamed of. Hot and tight, it nonetheless widened to accept your girth without a trouble, expanding not a single millimetre more than necessary to stroke and firmly sheathe your prick. During your month in Equestria you’d introduced more than one mare to the joys of plot play, but it seemed you were a mere amateur, fumbling with a finger at a virgin pony pucker while Derpy acrobatically soared through the sky above you, her bum stuffed full of toys.

Humping quickly with plot shaking thrusts, you found that you couldn’t hold back! Derpy’s dirtiest of holes was as well trained in the nastiest pleasures, even as her kissing lips were skilled at providing the most innocent of joys! As her insides milked you, swiftly bringing forth your second orgasm, you realized just how much you had to learn from the sexually gifted mare — if she cared to teach you.

“DERPY, I’M CUMMING!” you cried out at last, unable to restrain the pleasure one moment longer. Your balls clenched, your cock seized up, and you began to fling thick hot ropes deep into the pegasus’ alimentary canal. Pressing your hips as close as you could fit them against her voluptuous cheek meat, you tried to get every bit of yourself inside her, sending your cum rocketing that much further into the core of the mare you loved.

“N-no, she’s making me cum, it’s not fair...” Anonymous whined, even as his own dick clenched within Derpy’s folds and spat its own copycat load. How Anon longed to outlast you, to prove himself the superior lover! Yet his stamina, like yours, had swiftly broken under Derpy’s sexual assault.

You silently chuckled even as your fellow human’s balls twitched and his sperm overflowed Derpy’s cunt. You had nothing to fear from Anon’s creampie, for your own potent seed had long preceded his into the welcoming depths of Derpy’s still fertile womb. If the mature mare were to end this encounter with a fresh pregnancy, the foal — and thus Derpy’s heart — was certain to be yours!

From your month of lustful adventures, you’d learned that bareback human-riding was quite safe for any mare, even one in the deepest and most desperate heat... yet who knew what miracles might occur, when true love was at stake?

Slowly pulling out of Derpy’s tight and juicy butt pucker, you collapsed onto the couch next to Anon and relaxed. With a satisfied grin, Derpy slid to the floor before you and tended to each of her good boys with her mouth. She carefully cleaned off every trace of her twice fucked holes before sucking the two of you stiff again. Even after you were both erect and throbbing, Derpy continued her hungry blowjobs, moving her muzzle back and forth from Anon’s cock to yours, plunging her lips down to your very bases as she stroked one set of balls with each wing.

“Mmm, I love making you feel good... human cocks, so strong and tasty... glmmmph, glkk, glurrk!” Derpy let out a series of loud gags from deep in her throat as she easily swallowed each of your dongs in turn, then looked up at the two of you with an evil expression.

“Do you boys like it when I make those sloppy sounds?” she giggled. “I know how the mares do it in those naughty movies you like... lots of spit and nasty noises! Do you want little ole Derpy to be your pornstar? To gag on you so loud the neighbours can’t help but hear what big, hung studs I have in here?”

“A-anything you want!” you burst out, thrusting your hips and making your cock bounce up and down before Derpy’s eager lips. Every moment your dick wasn’t inside your lover was purest agony!

“N-no...” Anonymous murmured his objection to Derpy’s horny plan. “Sweet mommy, not nasty mommy...”

Derpy pouted with an exaggerated frown, even as she licked your combined dicksweat from her lips. “Hmph, I guess I’ll just suck you off all quiet and dignified, like a true lady. Oh, you silly stallions never let a girl have any fun...”

Reaching a hoof back to rub her clit, Derpy resumed a slow, sensuous, and nearly silent double blowjob. All that messy gagging was just for show, it seemed. Despite Derpy’s tiny size compared to you and Anonymous, hilting your hoof-width lengths in her stomach was considered simple and natural, something she did almost without thinking. No matter how huge, human shafts belonged balls deep down mare throats — by Derpy’s thinking, that was just the way of things!

All afternoon, you and Anonymous competed to bring Derpy the greatest pleasures of her life. You ended your blowjob by shooting a thick load down Derpy’s gulping throat, feeding her a rich meal while Anon masturbated between the deep valley of her teats. The two of you then spit roasted the mature mare, whirling her around and around so that she could clean a stew of cum from Anon’s cock, even as you pushed your combined sperm ever deeper up into her womb. Her holes were constantly filled by stiff human prick, her clit was polished by your eager tongues, her teats and plot were simply worshipped. Countless kisses adorned her lips. Her wings stroked you, her mouth served you, and her body blossomed and opened to welcome both of her new lovers.

Far from tiring you out, after each and every round of lovemaking you found yourself shortly refreshed, and eager to go again. Just the sight of Derpy’s caring smile or the sound of her satisfied sigh made you stiff and ready to bring her more pleasure. This was more than lust... it was pure inspiration. Derpy was a muse of sex, her mere presence swelling the cock and turning the male mind to thoughts of passion. No longer a mere mailmare, indeed no earthly pegasus, Derpy had ascended to become your goddess of love, a sensuous sight to put Princesses to shame.

As evening came on, any thought of lunch long since passed, the three of you lay on the living room floor, your bodies soaked with sweat and puddles of cum, the results of an epic inter-species coupling like no other. In the silence and intimacy of this rare moment free of raunchy sex, you knew that the time was right to make your move, and begin a lifetime of happiness with your true love.

“Please, Derpy, marry me...” you murmured, kissing her lips eagerly.

Anonymous playfully left hickeys on Derpy’s furry neck, hugging her tightly from behind with his cock still buried up her sphincter. “No, Derpy, I love you, let me be yours...”

Briefly your heart raced fiercely, but all jealousy was behind you now. The choice between you and Anonymous was Derpy’s to make. At a single word from her lips, you would happily depart from her sight to live out your life once more in miserable loneliness. An eternity hung upon her next utterance. It was time for her to choose, once and for all!

“G-guys...” Derpy murmured, squirming uncomfortably in your shared embrace. Your still stiff dicks throbbed hungrily within the twin furnaces of her sweat soaked, furry body. “T-this is really awkward, but I...”

“Let us both worship you,” Anon suggested. “We’ll be your willing love slaves, day and night. I’ll renounce Twilight, and take you as my one and only Princess!”

“Yes, forget about those other mares, you’re all I need...” What a solution to the dilemma! Even half of Derpy’s wholesome love would be enough to fill your heart to bursting!

Yet your heart seemed to shatter as Derpy Hooves frowned sadly, looking back and forth between the two males who had her sandwiched. “Guys, please, I’m so sorry. I didn’t mean to string you along, but this was only ever meant to be a casual thing.”

“Derpy, I beg you...” the words came unbidden to your lips, til they were silenced by a sad yet gentle hoof to your lips. To be rejected by Derpy’s cruelty would have been a strangely exciting prospect. To feel such kindness and tenderness even as she let you down, was nothing but a stab in the heart.

“Think of our feelings!” Anon pleaded, his green cheeks dripping with tears. “How can we live without you?”

“Oh, golly, how to explain...” Derpy sighed as she found herself in yet another embarrassing situation. “You’re both very sweet, but I just don’t think my husband would understand if I brought two more guys into the relationship.”

“Your HUSBAND?” you and Anonymous screamed at once.

“Yes...” Derpy shrugged sheepishly. “I thought you knew...”

“Where is he?” you demanded. “How dare he cuck us by loving and cherishing you!”

“Let me at him!” Anon pummelled one hand with his fist. “He’ll regret the day he stole you from me!”

“Boys, no, please don’t make hubby angry. He’s so possessive...” Derpy’s eyes glazed over and she began to pant and whimper, grinding on your dicks as she thought about her dominant lover. “So demanding... so predatory... sometimes I’m afraid he’ll tear me in two! Oh, but that’s always when I cum the hardest...”

At this moment of despair, as if the mere discussion of Derpy’s husband had brought him hither, you heard the creak of the front door and a friendly voice calling out to his undeserved lover. “Honey, we’re back from the carnival, I hope you had—whoa!”

You and Anonymous looked up at the open door to Derpy’s cottage with expressions of utter shock. Unbelievably, it seemed that while you were distracted by making love to Equestria’s sexy mares, a third tall, handsome human had made his way into this magical land. He stood in the doorway, his mouth wide open with shock, wearing a muscle tee saying I’M NOT THE STEPDAD, I’M THE DAD WHO STEPPED UP. A tiny unicorn balanced herself upon the human’s shoulders, gleefully hovering a stuffed teddy nearly as large as she was.

“No, d-don’t look, Dinky!” The intruder quickly turned about and cupped his hands over the young unicorn’s eyes, shielding from the sight of her well fucked mother. “This is not for you to see.”

“Dad, what is Mommy doing with the other humans?” Dinky asked with a worried tone. “Why is she so sweaty?”

“Erm, these are Mommy’s yoga instructors. Hey, what if you go next door and play with Zipporwhill for a while? In fact, you can spend the night!”

“Yay!” With a flash of magic, the unicorn and her carnival prize vanished in an instant, her innocence thankfully remaining undisturbed.

The foul, homewrecking human knelt before his wife’s exhausted form and took up two overflowing armfuls of jiggling pegasus MILF, pulling her off of your embedded erections with a loud slurping sound. “Derpy, honey,” he scolded with a kiss, “you were supposed to be finished hours ago. You knew I’d be coming back with Dinky, and these two gentlemen have places to be!”

“I-I’m sorry, Pillowfight,” Derpy moaned, her eyes moistening at her broken promise even as her lower holes poured forth oceans of your spent nut. “It just felt so good to have two human cocks, all to myself. I couldn’t help it! I HAD to keep going!”

Pillowfight? you mentally groaned. You should have known! Even a reader self-insert can’t win against an author self-insert!

The hated mare-stealer known as Pillowfight gently brushed the tears from his beloved’s eyes. “It’s OK, baby. You work so hard delivering the mail, you deserve to relax on your day off.” With a steamy, tail lifting kiss that coupled muzzle to mouth, he restored Derpy’s spirits and lifted her heavy heart, only to belatedly notice your presence once again.

“Heh heh, thanks for warming her up for me, guys,” he stated gratefully. “You don’t know how my cuddle muffin gets when her heat hits — I barely survived last month!”

Derpy helplessly slapped her squishy hooves against the human’s chest, pouting and requiring his attention like a foal in the midst of a tantrum. “P-please, lover,” she demanded, “no more talking, I need you inside me, now!”

“OK, baby,” Pillowfight chuckled. He shifted Derpy’s bountiful form to the crook of one arm and stood to his full height, holding her to his chest. “One good fuck, and then you’re going right into the bath. You’re really stinky.”

“Yay, bath time with hubby...” Derpy murmured, snuggling against her husband’s chest.

The unbelievably fortunate third human in Equestria turned back to glance at you and Anonymous, as he opened the door to the holy sanctum of the bedroom he shared with Derpy. “Let yourself out, OK?” he told the two of you. “We always keep some muffins in the kitchen, if you need a snack. Thanks, again!” Carrying his bride across the threshold, he shut the door behind him with a horrible finality, forever banishing your tender thoughts of a life spent growing old with the mare you loved.

“Why? WHY?!!!” you wailed, pounding on the flimsy door that separated you from utter bliss. “Derpy, I love you! Please don’t leave me!”

Anon embraced his brother in despair, weeping upon your shoulder. “Oh, the tragedy! The pain! That my love should be — w-wait, did he say free muffins?”

With a broken heart you sadly walked down the streets of Ponyville alongside your good friend Anonymous, munching on slightly stale muffins and taking turns kicking an empty tin can.

“It’s like I’ve always said,” Anon grumbled. “There’s too many God damn humans in Equestria! They’re taking all the good mares!”

You sighed, remembering the sheer bliss you’d found inside Derpy’s clasping horse holes. Would you ever feel such pleasure again? “How?” you wondered aloud. “How can a man go on, once he’s tasted paradise?”

“We’ve just got to stay strong, bro,” Anonymous urged you. “We’ve still got work to do... so many ponies need to get destroyed by big human cock, we can’t let them down!” Opening a small notebook, he sadly crossed out Derpy’s name, then smiled as he saw the one written underneath.

“Here’s some good news,” he told you, attempting to cheer you up. “Applejack’s my next assignment, and I could definitely use some help with her.” Anonymous tossed the remainder of his muffin into a nearby bin. “What do you say, bud? She’s demanding as hell, but at least she’ll feed us right.”

“Hrm, alright,” you agreed. “After all, Applejack’s practically a background pony!” You found yourself excited at the very thought of Applejack’s well toned, smackable flank. It seemed your tryst with Derpy had restored your vitality and your lust for mares. Despite the countless cumshots you’d spilled into the mailmare’s beautiful body, your cock now felt as fresh and innocent as the very first time you’d seen a winking equine vagina. Or perhaps the second time... that first time had been a little bit weird!

“Then I’ll race you to Sweet Apple Acres!” Anon announced cheerily. “First one there gets first choice of her holes!”

“Haha, you’re on!”

As you ran through Ponyville alongside your new comrade, your thoughts turned to the date you’d set up for tonight with the intelligent and well preserved Mayor Mare. The earth pony MILF’s beige fur wasn’t far from Derpy’s grey, and you already knew she dyed her mane. Maybe she wouldn’t object to going blonde for you...