Running a successful business selling exotic goods was a pretty promising lifestyle for Anon. Creating and selling treats from back home, of which ponies had no idea how to recreate, meant he had a booming business, constant orders, and something to keep him busy most days. Backordered for months, his delights were a rare delicacy to grace the palettes of most ponies. True, these were common name-brand candies and such back home, but for these ponies it was astounding. His stock was essentially always out, and he had oftentimes found ponies on his doorstep pleading for him to make an exception and squeeze in an order for them; he’d do his best to politely deny their request, but lately some of the citizens of Ponyville have been getting creative.
It actually just was petty theft.
As of late, he’d come to find multiple pieces of his stock missing. It didn’t take long for him to figure out why things were disappearing. Having heard a loud bang in his storage room, he had gone to check it out only to find a handful of ponies scurrying out and through his shop. Diving out windows, going through the back door, some even ran by him in a blur - yet it seemed like their go-to was a literal hole they had made in the wall. At first it bewildered him, but after that first encounter, it had become downright annoying. Finding no other option, he began restructuring the room to pony-proof it. Firstly, he removed the windows, then he had added extra locks to the backdoor, and finally sealed off the hole. He had assumed the security measures would’ve been enough, and from the looks of it, removing the windows and upgrading the locks worked wonders, but the issue of them literally breaking into the room remained. Seemingly uniting their efforts, these ponies continually weaseled their way into his home through more holes they worked together to make.
At the very least, only two or three ponies at the maximum would break in at a time, but even then he wasn’t satisfied. Having his goods pilfered was as frustrating as it was detrimental to his sales, and he had to put a stop to it. Finally though, he had found a true countermeasure for the nefarious, yet adorable, thieves he had to deal with on a near daily basis. Spotting yet another breach in his defenses they had made, he installed a trap. Whenever ponies would trigger the sensors he’d set up in the room, bars would drop down and seal off the hole - as long as one wasn’t going through it. Now that he had a proper trap in place, luring in a thief with a false sense of having an escape, he would finally be able to give his next unwelcome visitor a stern talking to for their insistence on not waiting for their proper turn.
With his trap set and ready, he went about his day. Reflecting on his plan, finding himself satisfied with the new development within his store, Anon sorted through his orders. Various candies and order numbers littered the paper he held in his hand, dictating the workload that soon awaited him. Squinting his eyes, inspecting it carefully, he placed it down and got to work. The job came naturally to him, and even with such a high demand, he’d manage it with relative ease more often than not. Walking over towards his cabinet, scooping up some exotic, imported cocoa beans from the higher shelf, he turned and made his way to his countertop.
Clang! Eep!
He paused mid-step, raising a brow and glancing over his shoulder towards the back of his shop. A mischievous grin split his face, knowing full well that was the sound of his trap going off. The surprised yelp of a few mares followed soon after, and from the sound of it it meant his harmless, yet effective, device had worked wonders. Snickering to himself, he placed his ingredient down on the countertop and made his way to his storage room. He’d be lying if he said he wasn’t a bit smug about his ingenious countermeasure working wonders, and now he’d get to lecture whomever was the poor pony who decided to steal from him.
Reaching the room, he heard a pair of voices, ones he recognized with ease. Going for the light switch, he caught sight of a pair of rumps squirming near the hole, clearly attempting to escape. His trap had worked wonders, seeing as it deployed a set of bars to block the exit off - ones that these two culprits tried to squeeze through. Already knowing just who was trying to steal from him, he sighed to himself, walked back into his kitchen, exited his front door, and made his way over towards the other end of their predicament.
Rounding the corner, he came face to face with the pair of ponies who had attempted to escape. Stuck between the bars of the exit, side by side, were none other than Pinkie Pie and Derpy. Both caught sight of him, nervously sweating as they seized their struggles to escape. The earth pony was a clear culprit, sheepishly looking up at him as candy littered her hair and she had a freshly made sweet stick in her maw. Beside her, cracking an innocent smile, Derpy hesitantly raised a hoof and waved over at him.
“H..hi, Anon…” she shyly mumbled, her smile showing the clear muffin crumbs around her lips.
Anon sighed, face palming from the sight before him. Of course the day he had fresh candy and muffins, these two would be the ones to siege his stash. Not only that, but they were two of his closest friends, and he’d feel pretty bad if he gave them a harsh talking to regarding stealing his stuff. He had to assume they had initially broken in from this very hole, but were unable to use it properly again due to the bars that had dropped down.
Not saying a word, he slowly walked up to them, watching as their eyes followed him carefully. Inspecting his trusty security system, he fought back a chuckle. The two of them had managed to squeeze their head and torsos between the bars of the makeshift barrier, but their hips were just wide enough to restrict their escape. From the front, it looked like they could possibly squirm through after some time, but their efforts certainly weren’t fast enough to evade being caught. He felt a tinge of arousal bellowing within him, eyeing up those wide hips of theirs and the curvy rumps they had, but he was quick to refocus on his objective.
“Hello, Derpy,” he replied, raising a brow and glancing over at the other culprit. “Pinkie.”
The pink party pony let go of the candy straw in her mouth, looking up at him with a blush. “H-hey, Nonny…”
“So,” he started, placing his hands on his hips. “Care to tell me what you two were trying to do here?”
The two of them exchanged brief glances, a nervous sweat running down their foreheads as they looked back and forth between him and each other. Seemingly thinking to herself for a moment, Pinkie sighed, pouting her lips.
“We were - um - borrowing some of your candy is all!”
Derpy perked up beside her, nodding her head. “Y-yeah! Borrowing! That’s all we were doing!”
Anon gave them a deadpanned look, rolling his eyes. “Borrowing…right. So eating my stuff is considered borrowing now.”
Pinkie Pie harrumphed, scrunching her muzzle. “Okay fine, we were stealing some.” She furrowed her brow, looking up at him. “But you can’t blame us! Your snacks are super duper good! They’re even better than Mrs. Cake’s marzipan mascarpone meringue madness!”
He should’ve taken that remark as a very touching compliment, being Mrs. Cake's signature dessert was nothing to scoff at, but the matter at hand came first. “I’m glad you like them, Pinkie, but you can wait like everypony else does!” He pointed at Derpy, leaning down. “And you! C’mon, Derpy! You’ve got so many muffins back home!”
“Y-yeah but nopony makes them like you do!” she blurted out, wiping her muzzle clean from the remnants of her edible crime.
Pinkie glared over at the pegasus. “Hey! You told me my muffins were the best!”
Shaking his head, Anon let out an annoyed groan. As much as he was looking forward to taunting whomever he had caught in his trap, he simply didn’t have the heart to do so with these two. They were some of his closest friends, and absolute sweethearts to him all the time. If anyone was going to get a pass, it’d be them.
“Listen, I get that you two like my stuff, but, c’mon.” He reached out, scruffing both their manes with his hands, earning a happy coo from Derpy and a short, surprised gasp from Pinkie. “You two are some of my closest buddies. I’d make an exception for you two and make you one of something.”
Pinkie pouted, staring at him with pleading eyes. “B-but only one?! There’s so many choices! So many flavors! A-and who could stop at eating one of anything you make! I mean, they’re just so so so so sooooo good that no sane pony could ever be satisfied with one! I mean, maybe Rarity since she’s adamant on keeping slim but -”
A finger to her lips silenced her rant, as Anon shushed her with haste. “I get it, my stuff is good, thanks. Still, being given a treat or two, exclusively, every once and a while is still something nopony else gets the option of. I’m sure lots of ponies would pay plenty to take up the offer I’m giving you two.”
“Well, getting one of your signature muffins is better than nothing…” Derpy mumbled, looking over at Pinkie.
“Let’s not glaze over the fact you two were literally robbing me two minutes ago,” he bluntly added.
Pinkie sighed, giggling soon after. “Ooookay ~ I guess you’re right…” She smiled over at him, beaming. “If I can at least get one of your kat kit thingies, or whatever you call them, here and there I guess I won’t resort to petty theft!”
“That…was an awfully blunt way to put it,” Anon sighed, rolling his eyes. He looked between the two, and then the bars they were lodged between. “You two…uh, can go.”
“About that…” Pinkie muttered, squirming in place. “We’re kinda stuck.”
Derpy tried as well, attempting to pull herself forward and free. “Yeah! Our flanks are too big to get through!”
Anon gnawed his lip, her blunt honesty about their predicament, and more so their flank sizes, sending a surge of heat to his groin. Again, he looked past them, eyeing up their plump rumps. Even without having a rear view, he could easily make out just how juicy their rumps were. Shaking his head, pulling himself away from his lustful thoughts, he countered.
“Do you want me to help you get out?”
The two gave him a nod and a quick ‘mhm’, affirming his assumption. Inspecting their predicament, doing his best not to ogle their curves, Anon did what he could to assess the situation. From the looks of it, he just had to dislodge them, so, assuming he could handle it simply, he reached down and grabbed Pinkie’s forelegs.
“I’m gonna tug ya ~ okay?”
“Okie dokie lokie,” she mumbled, a blush forming on her muzzle as he held her hooves in his hands.
Both of them strained, as he attempted to tug the mare forward, her plump rump pressing against the bars and preventing her from slipping through. After a few seconds of struggling, grunting, and pulling, they split apart and both gasped for air. Taking deeper breaths, having strained himself from the pulling, Anon rubbed the back of his head.
“Hmm - that isn’t really working out,” he stated, earning an unamused look from Pinkie.
Derpy perked up, putting her forelegs out and trying to catch his attention. “Okay! Try me now!”
Figuring there was no harm in trying, Anon waltzed over towards the pegasus. Grabbing her forelegs, he repeated the same process he did with Pinkie, earning an identical result. He watched as her flanks pressed against the bars, her hips too deliciously wide to permit passage with ease. Seeing them squeeze and jiggle with each tug sent even more warmth to his groin.
Releasing her, taking a sharp breath, he rubbed his chin. A few passing ponies had been giving them curious or suspicious looks as he tried to free them. With how they were stuck, their fronts were outside, meaning any ponies traveling around could see them. Opting to not draw a crowd from him trying to pry them loose, he had to find a different approach. Thinking to himself for a moment, he glanced over at the edge of the bars. They had made this hole near the floor, meaning they were able to place their forelegs on the ground outside and their hind legs on the ground inside - so, trying to shove rather than pull might yield better results.
Looking their predicament up and down, Anon nodded his head. “Hold on, I’ve got an idea.”
The two stuck mares watched him exit their view, left briefly with only one another and a few curious looks from passing ponies. They each strained, attempting to slip through the bars and failing once again. Groaning, they both gave up their efforts, having worked up a decent sweat from their failed attempts. They each exchanged looks with one another, catching the faint traces of a blush within each other’s muzzles, yet neither thought it wise to press the other as to why they adorned a crimson hue.
A minute or so passed, but finally Anon called out from behind them. “Alright! I’m gonna try pushing you two instead, okay?”
“H-huh?!” Pinkie stammered, her blush growing deeper. “Like…our flanks?”
Anon paused, looking over at the trapped mares. Truly, the only thing he could realistically push was their asses. He gnawed his lip, drinking in the sheer plumpness of their flanks. Pinkie’s ass was fat, arguably the thickest one in the entire town. He couldn’t lie, he often found himself ogling her cheeks whenever she walked by him; the way they jiggled and even occasionally clapped as she bounced throughout town was fuel to his ever growing fantasies about these colorful creatures.
Derpy wasn’t too far behind the party pony. Those bubbly cutie marks felt rather fitting for the bubble butt on the pegasus. Her ass was definitely a fair bit thicker than most ponies, and he had eyed her up plenty whenever she came by his store for a delivery. Her cheeks were curvy, yet bouncy, making for a delicious sight. He could envision the sight of them clapping before him vividly in his mind - only sending him further down this lustful tangent.
Sweat streaked down their bodies, from what he could only assume was their struggles to escape, and it added that much more to the sight. Their fur shimmered in the faint traces of sunlight that crept through the gaps of the bars, and between it only highlighted their sumptuous bodies all the more. Their tails flicked behind them, allowing him to get small glimpses of their perky ponuts and enticing cunts.
“Y-yeah…” he mumbled, drooling at the sight of their rumps as his imagination ran wild.
They both looked back at him, giving him rather unique looks. Pinkie was red in the face, seemingly incredibly flustered over something, while Derpy had a far more subtle blush, but gnawed her lip as she eyed him.
Positioning himself behind the pegasus, Anon called out to her. “I’m gonna push you now, alright?”
“O-okay, Anon!” Derpy blurted back, shifting herself as she prepared.
Anon leaned down, growing ever closer to those beautiful, gray buns of hers. Steeling himself and keeping his libido in tact, issuing a silent prayer to keep his composure, he reached out and cupped her flanks. His hands pressed into those fat asscheeks of hers like he was touching a pillow - his hand sinking slightly into her plump flesh with ease. His heart skipped a beat and his cock throbbed as he began to push.
He grunted, pushing into her pillowy flesh gingerly. He heard her uneven breaths, as she tried to wiggle forward and failed to escape. Pulling away, he tried again - both to try and free her and to satisfy the desires welling up inside him. With each subsequent attempt to push her, he indulged himself in feeling her up more and more.
After a few tries, he started to outright grab her ass, sinking his fingers into her asscheek and feeling just how fat it truly was. Finding his lust only growing, he went further. After a handful more tries, he began spreading her flanks apart a bit, giving himself a crystal clear view of her goods.
Each push ended with him spreading her, and each time he looked on in awe at the perfect set of holes Derpy had on her. From the fact that her grunts of struggle sounded like they were morphing into quiet moans, and how she wasn’t really trying as much anymore - he had to assume she had gotten worked up a bit from his efforts, likely unintentionally.
Her pussy confirmed his suspicions, as he spread her cheeks again on yet another push and saw it drooling with her arousal. Craving to see more, he pulled back and tried to free her again, this time eyeing up her backdoor as he spread her. Her asshole winked with what he could only assume was unwanted desire, yet the sight of the tight hole sent his heart aflutter.
He gave it a few more tries, before finally surrendering his efforts and forcing him to calm down. “Gah - sorry, Derpy. You’re definitely stuck in there.”
“I-It’s…okay…Anon!” she stammered, her tail flicking above her rump. “I really e-enjoyed you - er - appreciate you trying!”
Anon licked his lips as her tail twitched, giving him even more looks at her now winking marehood. He was certain she had no sexual desires with him as of now, but having her ass teased and groped still made her body respond appropriately. A bead of her essence ran down her thigh, the scent of fresh muffins filling the air as her arousal became a fragrant aroma filling the air.
“My turn.”
He blinked wildly, looking to his side. Greeting him was a stern stare from Pinkie Pie. Her face had gone nearly entirely red with her blush, she puffed her cheeks out, and her countenance was a clear look of…jealousy?
Anon was sure he was reading her wrong, but he shrugged it off. “What? If Derpy’s flank was too big to get through then -“
“I don’t care how fat my ass is!” Pinkie blurted out, eyes going wide as she covered her mouth. Shaking her head, her blush somehow deepening further, she sheepishly looked up at him. “Just - uh - try to push me out just like you did Derpy?”
Coming up behind her, already drinking in her fat, plump flanks, Anon shrugged. “Sure, Pinks, but I doubt it’s gonna work.”
“Oh! And, Anon?”
“Yeah?” he replied, looking her in the eyes as she looked back at him.
“I said just like you did Derpy.” She giggled, catching sight of Derpy’s flushed expression. “Okay? Let’s try and get me outta here!”
He hesitated for a moment, watching as she bounced her hindlegs in a way that made her ass jiggle. He could’ve sworn she had done that intentionally, but he passed it off as him imagining things. He and Pinkie were close friends, even sometimes making a lewd joke to one another here and there, but neither had ever done anything even close to genuinely sexual with one another. Chalking it up to either her being her usual excitable self, or maybe intending to mess with him with intent at a laugh, he gnawed his lips and bent down.
His hands loomed over that balloon butt of hers, thick, juicy flanks just dying to be groped. Her ass was absolutely to die for, and Anon silently thanked the stars above for his trap working in such an unintended way that it allowed for him to be blessed with what was to come. Drifting his hands closer, he pressed his fingers into her asscheeks.
His cock throbbed intensely the second he made contact with her rear, dying to be released and pleased before it became too much. Her ass was definitely a bit fatter than Derpy’s, being his hands sunk into her flanks a little bit more since she had more gib. Nearly enthralled in the moment, he snapped himself out of it before she’d get suspicious. He was supposed to be getting her out of her predicament, not losing himself in the wonders of feeling up such a divine posterior.
“Ready?” he asked, steadying himself.
Pinkie gnawed her lip, nodding. “Y-yup! Push away!”
Pushing his legs against the ground, Anon shoved her forward as forcefully as he could without hurting her. They each grunted as they struggled, with her pawing at the ground outside and him shoving her from behind - yet once again their efforts were in vain.
Taking a few, quick breaths, Pinkie giggled. “Whoops! Guess you gotta try again! C‘mon ~ Put some extra oomph in it like you did Derpy!”
The subtle, sultry tone she had used almost went unnoticed by Anon - almost. He couldn’t help but think she had an ulterior motive, and perhaps that his hunches weren’t actually skepticism but truthful. Still, he didn’t want to assume such a lustful and risky thing, so, he simply got ready to push her again - bar a few changes.
Like he did Derpy, he pushed against her with a fair amount of force, though this time he indulged himself in outright grabbing her ass during his efforts. Those pink mounds of glory were thick enough that he could genuinely grab onto them with relative ease, and it was a struggle to let his grip go each time he had to stop shoving. She seemed to have completely stopped squirming on her end, looking like she wasn’t even trying to get free anymore. She leaned down, biting down on her lip as he kept pushing - seemingly indulging herself as he fondled her.
Still, he had his role to play, and now he went further. If she wanted him to do exactly what he did to Derpy to her, he’d happily oblige. Shoving forward, he graced himself with the sight of her goods as he spread those buns of hers apart. A drooling, winking snatch met him, her clit engorged and showing the clear signs of arousal. Had he any doubt of her excitement, this had swiftly confirmed his assumption. She was digging it, and, as she flagged her tail up high and giggled, he quickly realized the turn of events that was now occurring. Licking his lips, lust overtaking him, he slowly pulled back and looked over the two.
Derpy’s tail had risen high above her flank as well, leaving them both openly presenting themselves to him. Their marehoods were both winking wantonly, and the scent of cotton candy mixed in with that fresh muffin smell from before. Their drooling snatches sang a song to his deepest desires, and his dick strained against his pants as it was reaching unbearable levels of lust.
“So, Pinkie, looks like you’re stuck too~” he cooed, waggling an eyebrow at her.
She threw him a sultry look, swaying her hips. “Oh no ~ How awful!” She couldn’t help but giggle as she heard herself talk, winking at him before she spread her hind legs further apart. “Though, from the look of your pants right now…I think you could help me with a different issue~”
Anon glanced down at himself, a clear tent in his pants resting below him. He had picked up on her arousal, and she had his, and it seemed like his afternoon was about to take a drastic turn. He hadn’t thought Pinkie was into him like this, but she was sending him signals even his dense self couldn’t miss.
“Anon? What’s gonna happen now - o-oh!” Derpy gasped, glancing back at him as well, her eyes focusing right onto his groin.
There the two stood, stuck between the bars and both looking back at him - blushes deep in their muzzles. Derpy gave him a rather curious look, mouth hanging open as she gasped, yet she didn’t tear her eyes off the tent in his pants. Pinkie playfully stuck her tongue out at him, her eyes half-lidded. Both their tails flagged themselves even more, moved to the side so he could see every part of their nethers and asses alike. Two wonderfully presented mares, who were both astounding ponies in their own right, was the stuff of any guys’ dreams - but this was Anon’s reality.
He slowly gripped his waistband, beginning to pull his pants down ever so slowly. The pair’s eyes never left his groin, with Derpy gulping nervously as it grew closer to being freed from his pants. Pinkie’s eyes danced with excitement, her tail wagging above her rump as her anticipation was becoming unbearable for her. He drank in the sight, enjoying the power he had over them for the time being as well as the idea of working them up more. Pinkie being into him was one thing, but it seemed clear as day that Derpy was craving him just as much - though she was too sheepish and nervous to make it as obvious.
Finally, he swiftly moved his hands down, freeing his cock from his pants. It sprung up, hard, long, and absolutely ready to pound some pussy - and it seemed he had a more than eager earth pony right in front of him. Pinkie licked her lips, shifting her hind legs even further apart and swaying her hips. She couldn’t stop giggling to herself, but even through her adorable laughter he knew what she was desiring.
“Sooooo~” she dramatically began, furrowing her brow and glaring right at him. “Wanna really spice up this party?” She bounced her hind legs, making her flanks jiggle. “Help me out, Nonny ~ I promise I’ll give you a proper apology for trying to steal your super duper yummy candy!”
Anon didn’t need to be told twice, stroking himself as he walked over behind her. The entire time, Derpy’s eyes trailed along, glued to his member as she gnawed her lip. He felt a portion bad about leaving her to watch, but he was confident watching and hearing Pinkie getting rut senseless beside her would push her beyond any hesitation. He pursed his lips, peering between the bars and outside, noting how only a few ponies were out and about. Plowing Pinkie here and now meant there was a good chance of one of the town’s citizens catching sight of it, but the idea of garnering a crowd only excited him further.
Coming right behind Pinkie, Anon slapped his cock right between her asscheeks, slowly beginning to grind against her. She gasped, shuddering intensely as she felt his shaft touch her, but soon after she started returning his efforts, grinding against him as he did her, letting out a light moan as she went. Her lust coated his cock, slickening it with her essence as he felt her ponut pulsing against him with desire. He struggled to decide which hole he wanted to go for, but eventually came to the decision that her pussy simply was begging to be filled. It winked over and over again, her juices cascading down and out of it, coating her thighs and the floor below in the sweet scented lust.
“D-do it, Nonny ~ H-help me out!” Pinkie clamored, her voice shaky.
He nodded in response, grabbing onto her hips. He steadied himself, pulling his hips back, lining himself up with her cunt. He prodded her entrance, biting his lip as he felt her lower lips winking against him. He hadn’t fathomed ever doing this with her, but now it was time to savor it all. Hearing her take a deep breath, readying herself, he grit his teeth and plunged straight into her. His length was graced with the warmth of her depths, her walls caressing around him like an angel’s embrace, massaging every last inch of his shaft and sending his nerves alight with pleasure.
Pinkie let out a deep, guttural groan, pressing her hips back into his own while he was hilted inside of her. Her walls clenched down on him, tightly gripping onto him as if they were desperate to not let him go. Yet, they were only just beginning. Gripping down on her hips harder, Anon pulled back out. Nearly entirely out of her, his tip the only part of his dick still within her walls, he thrusted back and with immense force. Her entire ass jiggled from the plunge, another moan escaping her lips, and he set to ruin her.
His thrusts grew rapid, slamming into her over and over as he lost himself to his lust. Rutting her with reckless abandon, he leaned his head back and let out a groan of his own. He didn’t care for any of his previous reservations, a border being crossed and opening the floodgates for both his and her enjoyment. He heard Derpy hitch her breath to his side, only reminding him that he had an audience - and he wanted nothing more than to be a crowd pleaser.
His tempo increased, his force intensified, and the cacophony of his grunts and Pinkie’s moans grew louder. He managed to glance between the bars and to the town outside. Nopony had stopped to gawk at them - yet, but he was sure at least one pony would stumble upon them after he was done. The rhythmic clapping sound of his groin slamming against her ass rang out, her cheeks bouncing wondrously with each titanic plunge he made. The scent of cotton candy began to overtake that of Derpy’s muffin-esque aroma, Pinkie Pie’s arousal skyrocketing as she started to inch closer to her climax. Their pace didn’t slow, with her now routinely slamming her ass back into him - eager and desperate to feel him push her depths to their absolute limit.
His tip poked her womb every time he drove into her, sending surges of delight through her every last inch and rocketing her closer and closer to the brink. His balls slapped against her clit, as he guided a hand lower and grabbed onto her ass. Her eyes fluttered, the world around her fading away as she was engulfed in a thick miasma of carnal delight. Moans crept past her lips with absolute ease, and every time she felt him slam into her her entire body lurched forward from the sheer force he used. Her desires were being sated and then some, and she couldn’t help but voice her delight.
“Ahn ~ Y-you’re s-so good, Nonny!” she stuttered, trying and failing to compose herself. “T-this is - nngh - so much f-fun!”
Her adorable, pleasurable words sang a song to Anon’s desires, as he began to swiftly ascend to his limit. His thrusts grew wild, disorderly dives into her tight depths as he was keen on filling her to the brim. Her entire body began to shake, telling him she too was mere moments from finding her own release - and thus he prepared for the finale of their rut. Steeling himself, grabbing onto her hip and ass hard, he grit his teeth and prepared to finish himself off.
“Inside! You gotta do it inside!!!” she wailed, tensing her legs as she prepared to slam herself back with everything she had.
Her words were the cue for them to go, as she pressed back and he slammed forward with everything they had. They held their position, both nearly going stiff as their orgasms hit them with the force of a dying star. Anon’s legs shook, Pinkie’s entire body shuddered, and they both threw their heads back and let out the rawest groans of pleasure they had ever released. He leaned his head back, looking up to the ceiling as his vision blurred. He had given himself a countless amount of climaxes in his days, but this was pushing the limit and entering realms he hadn’t thought possible.
Rope after rope of his cum shot straight into her depths, flooding her womb with ease as he pumped her full. The sensation of his molten essence coating her walls nearly undid Pinkie at a psychological level, elevating her climax beyond the gates of nirvana itself. Her tongue lolled out, her eyes rolled back, and she threw her head back in a silent scream - teetering between reality and fantasy both as the moment felt almost impossible to fathom. Her walls clenched down on him like a vice, milking him for every last drop he could provide, and her belly bulged a portion from the sheer volume he had dumped into her.
They each gasped for air, coming down from their orgasms and returning to the realm of sanity. Sweat streaked down them both, chests rising and falling as they took in each breath deeply. The last vestiges of his seed poured into her pussy, leaving her thoroughly filled and pleased alike. Gradually, he pulled his hips back, his cock inching out of her as her walls tried to greedily keep him inside. With an audible pop, his cock escaped her depths, cum spurting out of them and falling to the ground below.
“A-Anon?”
The two of them perked up, unable to even utter a word to one another before they were firmly reminded of the mare to their side. Blinking wildly, they glanced over at Derpy. Her blush had spread across her entire face, nearly red as an apple now as she looked thoroughly flushed. She scrunched her muzzle as they met her eyes, taking shaky breaths as she looked between them.
“Hah ~ What’s up, muffin head?” Anon cooed, resting his hand against the wall and recovering from his recent release.
“I…well…I…” Derpy stammered, hesitating to get her words out.
Pinkie nudged her shoulder, giggling to herself. “You want some ‘help’ too, dontcha?” She leaned over, whispering into the pegasus’ ear. “His cock is super duper good ~ Don’t be shy~”
Derpy shivered at her words, feeling Pinkie caress her shoulder with a foreleg. The mere touch of another creature sent the pegasus’ mind for a whirlwind, her tail flicking nonstop behind her. Feeling her marehood give an especially enthusiastic look, looking into Pinkie’s eyes and seeing her give a playful wink, she gulped and glanced back at Anon.
“C-can you help m-me too?”
Anon’s cock shot straight back to being rock hard upon her request, ready to go once more. He looked down at Pinkie’s ass, seeing the result of their carnal embrace, then glanced over at Derpy’s plump rump. Her flank was absolutely tantalizing, but it’d look even better with his cum drooling out of her depths.
Giving Pinkie’s cheeks a parting slap, earning a yelp from the earth pony, he came up behind Derpy. “You sure?~ You don’t sound all too confident!”
“I…I am?” Derpy replied, shying away as she was getting far too flustered.
Pinkie lifted her chin with a hoof, making her look right into the mare’s eyes. “C’mon ~ Tell him how much you want him to stuff your pussy full with his super cock! Let him know just how much you want it! It’s fun!”
Derpy took a deep breath, smiling over at the party pony before glancing back at Anon. Spreading her hind legs apart, she swayed her hips like her partner did earlier, and threw on her best sultry look. “Please ‘help’ me like you did Pinkie! I’m - uh - really good at making things up to ponies too! I can show you! While you - erm - ‘help’ me!
Anon and Pinkie exchanged looks, both chuckling to themselves.
“Eh ~ Good enough!” he declared, coming up behind her.
Grabbing her asscheeks, earning a eep from the mare, he adjusted himself and slapped his cock right between those bubble-marked flanks like he did Pinkie Pie. Just like the earth pony, he began to grind against her, feeling her essence begin to coat his shaft and balls.
“Pssst ~ hey!” Pinkie not-so-quietly whispered, gaining the thoroughly embarrassed pegasus’ attention. “You gotta push your booty against him! Grind against him like he is with you! Trust me, it feels so good!”
“O-oh?! Ahn~” Derpy gasped, shuddering and moaning as she felt him teasing her holes. She glanced back at him, nodding her head. “Okay!”
She took a moment, but eventually she caught onto his rhythm and began to grind against him. Every time he moved up, she moved down, and vice versa - ensuring every part of her holes felt him throbbing against them. The warmth of his member sent her lust into overdrive, becoming impossible to ignore.
“D-did I get you ready enough?” she nervously asked, avoiding looking him in the eyes. “This is way more complicated than delivering ponies’ mail…”
Anon pulled his hips back, lining his tip up with her snatch. “How’s this for an answer?”
“Huh? But you didn’t even answer my - nnngh! O-oh wow!”
Her reply was morphed into a pleasurable exclamation of wonder, as Anon drove into her. His cock was already thoroughly slickened with the mixture of her and Pinkie’s juices, allowing him to plunge balls deep into her in one swift swoop. Staying still for a moment, he bit down on his lip.
Pinkie had been snug, but Derpy was downright tight. Her walls contrasted with her hesitant nature, clenching down on his member with endless desire and need. They gripped his entire rod, already trying to milk him dry of everything he was worth - and they hadn’t even started yet! He knew full well he’d come fast with how snug she was, which meant he had to go all out from the get go.
Barely giving her time to recover, he pulled his hips back, winked at her, and began to pound into her. She had been thoroughly unprepared for the spike in pleasure and speed, a sea of moans flying out of her lungs and out for all the world to hear. Her wings tried to unfurl, desperate to stiffen at her sides as she was overwhelmed with his carnal fury.
“W-woah! Nnngh! This feels amazing!” she cried out, her sheepish nature seemingly extinguished as she was being plowed.
Pinkie snorted to her side, licking her lips. “Toooold ya ~ He’s gotta make that tushie of yours bounce while he ruts you! I’d know, after all!”
And bounce it did. With each thrust into her, her ass jiggled and clapped in harmony with his body pressing against hers. She might’ve not been as thick as Pinkie, but Derpy was still packing quite the set of flanks on her. Those cutie marks of hers rippled as he rutted her with reckless abandon.
“O-oh, wow! Unf! Nnf! You’re really really big!” she moaned, eyes fluttering with delight.
Besides the subpar dirty talk, which Anon appreciated her even trying - though a part of him thought it was just naive commentary from her in actuality, she was an incredible fuck. Thick ass, tight pussy, and an absolutely adorable voice to give to her moans - it blended into an amorous experience that certainly rivaled Pinkie’s.
Having just had the arguable best fuck of his life, and now dealing with a worthy competitor for the title, Anon was already beginning to ascend to a climax. He was worried he’d actually manage to underperform for the mare, but as Derpy’s moans grew more frequent and her body quivered beneath him - his worries were alleviated.
He kept his motions going, feeling her begin to throw her ass back into him as he thrusted forward. Even with how adorably naive she was, her marish instincts directed her, guiding her to more pleasure and closer to what her body yearned for - a climax.
She began to lose the little composure she had, blurting out the only thing she could properly feel. “I…I feel - haaa - s-so warm!”
Anon tensed, clenching his eyes shut as his balls began to strain - mere moments from his climax.
“Do it inside her.”
He cracked open an eye, catching a glimpse of Pinkie’s face. He had never thought he’d see her looking so fierce - so determined yet so lustful at the same time. Her eyes had a fire of passion and excitement in them, dancing as she looked right back at him.
“Trust me, it’s always more fun inside.”
As if her words worked magic on him, Anon came. Throwing his head back, letting out a deep groan, he slammed into Derpy and held himself in position. His nuts pulled up, his cock flared, and the first ropes of his release shot into the pegasus’ depths.
The world around Derpy morphed into a blur, the only things she could register being the pleasure she was experiencing and the two friends she had with her. Her eyes rolled back, her tongue hung out of her mouth, and she cried out in absolute bliss.
“W-woooooooah!!!”
Not the best line for an orgasm, but nevertheless her climax struck her with the force of a tsunami. Her body seized up, nerves going alight with a pleasure unbeknownst to them. It was as if she crossed into a realm that encompassed the very concept of bliss itself, yet she was still in Equestria, still stuck between these bars, and still having his cock lodged deep inside her - and that only made it all the more amazing.
She felt his seed flood her womb, gushing out of it and coating her walls thoroughly. Every rope Anon pumped into her pushed her body to new limits, her belly subtly bulging as he gave her an equally impressive load as to that of which he gave Pinkie. The seal his cock made on her pussy acted as a barrier, locking his essence deep within her and letting her bask in the sensation of her body being shown new heights of pleasure.
The feelings accosting her only furthered as she felt him slap her ass, losing himself and forgetting to have any kind of reservations. She hadn’t expected it, but the mixture of pain and pleasure awoke something unknown within her, coaxing a silent scream of bliss from her lips. She shivered intensely, feeling the final gushes of his spunk exit his cock. Only when his flaring member began to calm did she start to come down from her orgasm.
The world slowly took shape around her again. Her eyes fluttered, she breathed heavily, and her front half nearly collapsed. Beside her Pinkie smile, looking her up and down, eyeing her rear.
“Oooh ~ And here I thought Nonny gave me special treatment! Guess he just gives every mare all the cum in the world! That’s so sweet!”
Derpy giggled, a satisfied look spreading across her countenance. The heat within her had faded, for now at least, and the feeling of being stuffed with Anon’s cum gave her a sense of relief. She let out one final moan as he pulled out of her, his cum soon streaming out of her pussy and down her thighs.
“T-that…was the bestest thing ever…” she dopily cooed, a smile forming on her muzzle.
Anon stumbled back, looking over the sight of two throughly fucked mares before him. He leaned down, putting his hands on his knees as he recovered from his two back to back climaxes, smirking as he felt pride welling within him. He had performed more than well, bringing both of them to what he could only assume was some of the best orgasms of their lives, and with that he couldn’t feel any more complacent.
“Oh - hi, Twilight! Hi, Rainbow Dash!”
And his sense of tranquility was sundered in an instant.
Darting forward, he glanced between the two ponies and out the bars, catching sight of what he worried he’d see. Standing a fair amount of feet away, Twilight Sparkle and Rainbow Dash gawked at the three of them, a look of shock, surprise, and even jealousy spread across their countenances. He had thought he wouldn’t have been worried about any ponies stumbling upon them, but those two were also some of his closest friends, and now he was thoroughly embarrassed.
“Well, now we can get outta here!” Pinkie laughed, looking back at him. “Twilight can teleport us riiiiight out!”
Anon hastily began to redress, worried he’d get an extensive lecture from the Princess about the difference between friendship and friendship with benefits. “That’s…that’s great Pinkie.”
“But there’s also another teeeeeny tiiiiiiny problem…” she continued, nervously chuckling.
He stopped midway of pulling his pants up, eyeing her suspiciously. “Uh…what?”
“Yeah, what’s the matter?” Derpy asked, looking over at a blushing Rainbow Dash. “Oh! Hi, Rainbow Dash!”
Ignoring the fact that the pegasus took that long to realize they had an exterior audience, Anon pressed Pinkie Pie further after seeing her awkwardly smile. “Pinkie, what is it?”
She sighed, rubbing the back of her head. “Remember you told me about that potion you were having Zecora make?”
“In case I found a special somepony?” he asked. “Yeah, why?”
Pinkie winced, once again laughing awkwardly. “And you said it’d let you…y’know, knock up said special somepony if they were in heat?”
Anon nodded. “Yeah! Zecora can make a potion for anything! It’shonestly insane just how much she can -“ His eyes went wide, his heart skipped a beat, and he looked over at Pinkie with shock. “Wait…you aren’t…”
“In heat?” Pinkie replied, adorned with a wide, forced smile. “I kiiiiiiiiiiiiinda am…”
He gave a defeated sigh, standing upright and putting his hands on his head. Pumping a foal into Pinkie, as the potion should’ve made him compatible with them and not vice versa, was definitely not on his agenda - ever. It wasn’t that he didn’t like the idea of starting a family with the mare, hell he knew she’d make a phenomenal mother, but it felt sudden, and was absolutely unplanned. He liked Pinkie, a lot, but this was an unprecedented development in their relationship as friends.
“O-okay, that’s well, not really what I wanted to hear, but at least it can’t get any -“
“Oh? I’m in heat too!” Derpy cheered, before blinking as she came to a realization. “Does that mean Nonny got me pregnant too?”
A loud thud rang out behind her, ushering her and Pinkie both to look behind them. Laying on the ground, unmoving, was Anon. The news that he had knocked up Derpy as well had been too much to bear, and he had fainted before he even had time to register just how insane everything had become.
Pinkie shook her head, rolling her eyes. She hadn’t planned to get knocked up today, but the spontaneity of it all only made it all the more fun. She was always one to put a positive spin on things, and she knew she’d be more than fine with Anon. With Derpy mixed into things, it looked like she was going to be part of a herd - which was every mare’s dream!
Looking away, seeing Rainbow and Twilight still gawking in shock, she giggled and flagged them down. “Hey! Mind getting us out of here, Twi?” She looked back at Anon, scrunching her muzzle. “Oh, and we might need Nurse Redheart too…”
Six Months Later
Anon fumbled with a rolling pin, carefully using it to press against some dough he had laid out before himself. Life had been mostly normal as of late, besides two things.
Ponies had once again begun stealing from his stash, which forced him to reinstall his trap, and two, he now had two eager assistants working with him in his shop.
Humming to herself, carrying a baking sheet in her maw, Pinkie trotted past him. Her body had turned into a clear indication that she was carrying Anon’s foals, and she wore the look with pride. A round belly, stupendously fat ass, plumper tits, thicker thighs, and a libido that seemed to be unending - she indulged herself in her new motherly form plenty. Wearing a cute apron that hugged her form, still as bouncy as ever, she placed the tray down and got to work.
Thanks to their newly formed herd, Pinkie had insisted Sugarcube Corner and Anon’s shop form a partnership. Now supplying his goods to the parties the other shop arranged, Anon allowed Pinkie Pie to assist him in his day to day work. She had been more than happy to do so, and outside of taking breaks to get fucked senseless by him, she was rather efficient.
Derpy however…tried her best at least.
A loud crash rang out behind him, and he didn’t even have to turn around to know what happened. An adorable ‘oops’ met his ears, yet he couldn’t even be mad. Derpy too had developed into quite the motherly figure. Her ass was a fair bit plumper now, her tits had ballooned, and her thighs got all the more tantalizing. Not only that, but she had become much better at dirty talking and sex overall - which was bound to happen with Anon plowing her at least three times a day.
Even with impending fatherhood on the horizon, Anon found himself at relative peace. Derpy and Pinkie had proven to be lovely partners both romantically and sexually, and he was certain they’d raise wonderful families. The only thing truly concerning him nowadays was the return of thieving ponies, but his trap was once again in place. Seeing that they had made a hole in the exact same spot he had originally found Pinkie and Derpy lodged in, it was only a matter of time before…
Clang! Woah!
It finally got sprung.
“Welp,” he started, dusting his hands off, “guess we should go see who -“
Pinkie Pie stopped him from continuing towards the back door, a sudden mischievous look spreading across her face. “Y’know ~ Maybe it’d be better to check outside first? Who knows…maybe the two of them got stuck too!”
“The two of them? How would you even know -“
“Just go, Nonny!” she interrupted, puffing her cheeks out. “It’s no fun if you keep them waiting!”
Nearly pushing him towards the front door, he surrendered and heeded her request. Turning the door, he slipped outside.
“What was that all about?” Derpy asked, curiously looking over at Pinkie.
Pinkie snickered, winking at the pegasus. “Oh, y’know, I might’ve told some friends about his trap being back…”
Anon peeked his head back into the house, having not left yet. “Did you say something?”
“Nope,” Pinkie replied, deadpanned. “Go.”
He sighed, turning away and leaving. “Fine. Those hormones sure have made you more demanding...”
He continued to grumble to himself, thoroughly confused by why Pinkie was acting the way she was. He knew mischief when he saw it, especially on her, and she reeked of it right now. Turning the corner, he froze in place, spotting two ponies stuck between the bars, just like Pinkie and Derpy had been. He couldn’t mistake that prismatic mane on the first one or that lavender coat on the second with anyone else.
“Oh, it looks like we’re stuck!” Twilight blurted out, her voice sounding forced and absolutely acted out.
Rainbow threw him a look, fiery lust in her eyes. “Guess you’ll have to ‘help’ us out, Anon ~ We can definitely ‘repay’ you for the stuff we stole!”
There wasn’t a piece of candy on them, and he knew full well they hadn’t taken anything. Still, peering past their faces and to the bars, he saw two fat, juicy flanks just waiting to be plowed. He thought to himself for a moment, before his dick already began to strain in pants and made his decision clear.
No herd should only have two mares anyways…
