Double Booked

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...