Winter Quill and the Knotty Seamstress

by TheVClaw

Rating: mature
Tags: Alternate Universe, Diamond Dogs, Original Character, Porn, Fetish, Rarity, Sex, Profanity, Random, My Little Pony: Friendship is Magic
Length: 9728

After developing a more content mindset towards promiscuity, we well as enjoying the company of others in a more physical way, Rarity decides to generously provide her services to a stallion who wishes to feel something more intense~

Note: This story was a commission for Winter Quill from my Official Patreon page, and is a shameless clopfic involving M/M and M/F content; these include themes such as promiscuity, sluttification, Diamond Dogs, knotting, intense stretching (both vaginally and anally), glory holes, public use, and small penis humiliation. Reader Discretion is advised.
Also, this story is set in the same universe as Chronicles of a Sluttified Spike, so context might be necessary.

Due to her close friendship with Spike, who had recently morphed from a simple Royal Assistant to Ponyville's resident cockslut, Rarity eventually developed a similar mindset towards body acceptance and promiscuity. And before too long, Ponyville's posh fashionista was willing to provide more physical services to various stallions who came to the Canterlot Boutique. One of those stallions was a tan unicorn named Winter Quill, who was more than accepting of a casual romp with the mare when he showed up for a new dress; however, upon learning how open-minded Rarity really was, Winter decided to pique his curiosity about some indulgences himself...

Published 2020-06-16 06:00:01 UTC
Last updated 2020-06-16 06:00:01 UTC

AKA, Winter Gets All Tied-Up

It was a bright and sunny day in the land of Ponyville, and everything seemed to be perfectly normal as judged by the hamlet’s busy streets. Along most of the cobblestone roads, ponies from all walks of life were going about their days with cheerful smiles and friendly demeanors. Most of the town’s businesses were as busy as could be, since the lunch rush was leaving the outdoor marketplace packed with hungry ponies exchanging bits with vendors. Even Sugar Cube Corner was booming with an upsurge of customers, which included a line that went out the front doors while Pinkie Pie’s accordion music could be heard inside.

But despite how busy Ponyville may have been that day, there was one particular business that had a ‘Closed’ sign hung over its front doors. Even though the business hours posted at the side should’ve indicated that the place was open, it seemed that the town’s local clothing and fabric boutique was temporarily shut-down for some reason. Of course, considering how the Carousel Boutique was owned by Rarity, one of Equestria’s well-renowned heroes as the Element of Generosity, not many customers seemed too upset when they walked past the Closed sign. For all they knew, the posh unicorn mare was most likely hanging out with one of her friends, or even off to help solve a major friendship conflict somewhere in Equestria.

However, if any ponies were to lean in close to the front doors, they likely would’ve heard some muffled voices coming from inside. More specifically though, they would’ve overheard the faint, rapturous moans that were stemming from a mare and stallion upstairs.

“AAAAHHHH!!!~ Kee… K-Keep going!” Rarity’s eyes were rolled back blissfully as she clung to the headboard of her bed with both hooves, and tried to stay in place while being pounded relentlessly from behind. Sweat was beading down her blushed face while she wailed out in ecstasy, but it was doubtful she was thinking too much about her appearance when a thick, meaty cock was pistoning in and out of her. Her body was reeling in pleasure every time she felt the stallion’s hips colliding hard against her flanks, and she felt his cock sinking deep inside of her to titillate every inch it could reach. “Mnnnghhhh… Ohmigosh, YES!! YES DARLING, YES!!!~”

Meanwhile behind the cock-stuffed fashionista, a tan unicorn with white fetlocks was panting heavily while trying to maintain the veracity of his thrusts. Due to how heated their impromptu session was getting, his thick dark mane was starting to cling to the sweat dripping down his face. Not to mention, the stallion’s glasses were fogging up tremendously atop his blushed muzzle, which kept him from really appreciating the sight of Rarity’s tantalized state. However, due to how deep and alluring her belting moans sounded, the stallion could only shudder in delight while plowing that dripping pussy for all it was worth.

“Mnnnghhh!!~” Rarity’s head reeled back as she shivered elatedly, her marehood trying to clench around the girth of that thick and veiny cock. The added constriction caused him to groan out while his hooves clasped both of her plump, supple flanks in a tight squeeze. Meanwhile, his cockhead continued to slide across the mare’s sensitive folds to leave her writhing on the bed, while the sharp throbs from his shaft indicated how close he was getting. And with the way his thick, heavy balls were constantly smacking Rarity with every thrust he gave, it was hard for her not to reach climax first when her clit was being lightly tapped by his sac. “Aaaaahhhh! W… Winter, I… I’m about to!”

“Aaaahhhh!!” The stallion was groaning just as deeply as Rarity, and leaned himself back while shoving his cock as deeply as he could inside of that hungry cunt. “Nnnfff~ I… I’m gonna cum too!” moaned Winter as he throbbed more prominently between the mare’s puffy lips, and his balls started to ride upward with each pulsation that left his hooves quivering badly.

Rarity was still clinging to the headboard, but her lead loomed downward so that her muzzle was pointed to the satin sheets underneath them. Her state of mind may have been thoroughly frazzled due to how intensely she was being stuffed with hot, throbbing cockmeat; but as her eyes opened halfway to resemble a dream-like expression, the sight of the bedding below prompted her to moan out instinctively, “Aaaaahhhh!! D… D-Don’t try to stain the sheets, Mister Quill!! Ju… J-JUST DO IT INSIDE!!~”

Winter Quill’s eyes may have widened in shock from such a request, but the mare’s boisterous plea was hot enough to make him respond accordingly. His body froze up as he spasmed hard atop Rarity’s presented form, and his eyes clenched shut as he gave one final thrust into her. “Ahhhhh!! AAAAHHHH!! AAAAAAAHHHHHHHH!!!~”

The moment his balls pressed up tightly against Rarity’s throbbing clit, the mare shrieked out loudly enough to make the windows vibrate like the champagne glasses in an operahouse. But fortunately for the two fornicating ponies, her lustful cries of pleasure weren’t noticed by anypony outside the boutique. Because of that, Rarity was able to truly appreciate every hard, intense pulsation from Winter’s member as he unloaded inside of her. Her marehood clenched around the girth of his shaft like a vice, ensuring that every drop of his seed would flood her quivering pussy and leave her feeling tremendously full. And as Rarity felt those constant waves of pleasure coursing through her body to leave her nerves titillated all over, her hooves eventually let go of the headboard so she could slump down on the mattress with her ass still sticking up. “MmmmMMMMMMMnnnnngggghhhhh…”

“Aaaaaaahhhhhhh…” Meanwhile above the contentedly stuffed mare, Winter Quill could barely keep himself upright while shooting thick, heavy ropes of cum straight into Rarity’s deepest depths. Even though he had only shown up to the shop to get a re-fitting for his jacket, he wasn’t one to complain about the mare’s unconventional way of giving him a “tip” for his kindness. Even when the throbs of his stallionhood eventually receded, and he felt the last of his hefty load settling deep inside of the moaning mare, Winter still tried to hold her close as he hugged her barrel tightly with both hooves. And by the time both ponies were thoroughly spent following that raunchy session, the two could only pant in exhaustion while Winter was tiredly mounted over her back.

“Ho… H-Holy shit,” he muttered after a long bout of silence, which elicited a tired giggle from the mare below due to his unexpected expletive. Fortunately though, Rarity didn’t seem to mind the stallion’s language as she felt his thick cock twitching hard inside of her. When she finally felt his length beginning to soften between her quivering lips, she let out a pert sigh that caused Winter’s ears to perk up attentively. “Uhhhh… A-Are you alright, Miss Rarity?”

“Oh, absolutely darling~” To emphasize that point, Rarity only needed a brief stretch of her hooves before she lit up her horn, and caught Winter by surprise by floating him off of her back. While the stallion yelped out briefly, his cock could be heard exiting her well-used entrance with a wet pop. But despite how flooded he left her stretched-out pussy, Rarity was quick to cast an additional forcefield spell around her nethers as she pulled herself off the bed. When Winter was landed back on his hooves, with his semi-flaccid cock still slathered with a thick sheen of his and Rarity’s secretions, the mare was humming to herself contentedly while trotting to the bathroom. “Believe me, after the exhausting morning I had dealing with Spoiled Rich, you have no idea how badly I needed some release~”

Winter Quill could only huff with a confused-looking smirk, and shrugged to himself while scratching the back of his mane. Considering how many times he visited this shop over the years he’d been living in Ponyville, he never would’ve expected for somepony like Rarity to offer herself for a quickie. Even though he deeply appreciated the session, mostly since he was dealing with a taxing week himself, it was still jarring to think of a mare as high-class and dainty as her to carry such a casual demeanor in regards to sex. Of course, considering who else had developed a similar mindset within Rarity’s close circle of friends, Winter couldn’t exactly question where she may have developed her cavalier attitude from.

Like many, many other stallions in the Ponyville area, Winter Quill was fully aware of the shocking transformation that came from the town’s resident dragon Spike. Even though the pudgy little guy was a Royal Assistant for Twilight Sparkle (and looked young enough to be mistaken for a grade-schooler), he had somehow developed a sudden bout of maturity that didn’t affect his appearance, but his libido. And since Spike was technically a legal adult in Equestria, and had gotten approval from Princess Celestia herself, he had been servicing most of Ponyville’s stallions (including Winter himself on a couple occasions) as a genuine cockslut. The first couple weeks may have been weird for most of the town -- mostly since so many of them assumed he was way younger than he actually was -- but enough time had passed for most ponies to treat Spike just as they had before he returned from the Dragon Lands.

“Y-Yeah, I get what you mean,” said Quill as he nodded to Rarity’s remark. “And to be fair, sex really does help to alleviate stress. I read that in a study a while back.”

“Mmhmm. So have I.” Rarity kept her bathroom door wide-open as she bent herself over, and tried to look at her creampied pussy through the vanity mirror. “Not to mention, Spike really helped me to carry an open mind about appreciating such taboo things~” Not even caring that Winter Quill was standing right there to watch her, Rarity used her magic to float a washcloth across her backside to lap up the rivulets of cum trying to leak out. Of course, even when most of Winter’s load was either soaked up by the rag, or settled deeper inside of the mare without much urgency, it was obvious what had happened when he got a good look at Rarity’s loose and slightly sagging marehood.

“Unf~” Even though his own endowment probably made her gape appear more notable right after they fucked, Winter was willing to assume that Spike wasn’t the only one who was embracing casual sex with multiple guys. And with that well-used marehood looking particularly alluring in his line of sight, Winter squirmed a bit while blushing profusely. “I-I’m not gonna lie, I really wouldn’t have expected somepony like you to feel that way. N-Not that I’m complaining though! It really is great to be with a mare as loose as you~”

Rarity whipped her head back towards Winter with a wide-eyed look on her face. “Excuse me?!”

“W-WAIT!” Winter Quill instantly realized how she may have taken that comment, and threw his hooves up to add insistently, “I’m not saying that as an insult, I swear! S-Seriously, I… I honestly really prefer it~”

Even though Rarity herself wasn’t specifically upset about the state of her overused pussy, Winter’s insistence prompted her to raise a brow in suspicion. “... Really now?”

“Mmhmm~” Winter nodded with a more natural smile, even though his sheepish blush was still glowing across his cheeks. “I-I mean, like… Most of the time when I’m with a mare, they’re usually too tight for me to really enjoy it due to my, errr… you know…”

Since his thick cock was still hanging flaccidly between his legs, Winter only needed to motion down towards it without saying anything else. Rarity’s other brow rose before she gave an understanding nod. “Aaaaahhhhh… Well, I suppose that makes sense. You are very well-endowed, after all~”

Winter Quill tried to smile with a thankful nod to that compliment, since he knew that she meant it in the best possible way. However, the stallion couldn’t help looking away from her as his muzzle wrinkled a bit, almost as if he saw his endowment differently than she did. Fortunately for the stallion, Rarity’s attention to detail prompted her to take notice of his response, and then added with a sympathetic shrug, “Although, it’s also nice to know I was able to provide that kind of pleasure for you despite previous experiences~”

That comment got to Winter a lot better, and he looked back at her with a gracious smile. “Well, ummm… thank you, Miss Rarity.”

“Oh, you don’t have to be so formal, darling!” After waving aside his comment with her hoof, the mare exited the bathroom while her tail was still lifted, and her loosened marehood was proudly on display. “Honestly, after that rousing session, I think it’s safe to say our relationship can be more casual, don’t you think? Besides, the only gentlemen who refer to me as ‘Miss Rarity’ are my, err… Business Associates…”

Rarity tried not to falter too much when she said that last detail, but her hesitant tone caught Winter Quill’s attention. When he glanced back at her with narrowing eyes, he could see the brief bout of blush that deepened across the mare’s ivory cheeks. Not to mention, Rarity was quick to avert her eyes from Quill after mentioning her ‘Business Associates,’ which prompted him to grow a cheeky smirk and ask with a huff, “Let me guess… are your ‘Business Associates’ the ones who helped you to be more… accommodating?~”

Despite her embarrassment on the matter, mostly due to who specifically she was seeing as part of her business and pleasure endeavours, Rarity shot a look back at Quill with a warning smirk of her own. “You should be careful about what you may be implying, Mister Quill~ I might be comfortable enough to discuss more personal matters from time to time, but a Lady should still have some secrets~”

“Y-Yeah! Yeah, of course…” Winter quickly nodded to that point, not wanting to upset Rarity following that little quip. However, after seeing how stretched-out her marehood had gotten, the stallion couldn’t help blushing as he looked away from her and rubbed his foreleg with a hoof. “I-I was just asking out of curiosity, that’s all…”

“Curiosity?” repeated the fashionista as she eyed him with intrigue. “And just what might you be curious about, hmm? Were you wanting to know of any other mares who might be as ‘loose’ as myself?~”

Even though she wasn’t planning to actually name any particular ponies who had shared the same experiences as herself, Rarity hoped that her direct wording would prompt Winter to try and change the subject. But much to her surprise, even when the stallion shook his head in clarification, his blush was still rather deep while looking back at her timidly.

“I-It’s not that. I, uhhhh… I was kinda hoping to be looser myself~”

Considering what the two had just finished doing, Rarity’s eyes widened immensely in response to Quill’s admission. “Ummm… Y-You?” she asked before blinking a couple times in confoundment. She looked Winter Quill up and down without saying much, not expecting for him to give such a request. “You mean… yourself?”

“W-Well, ummm… Yeah, I guess…” Winter was looking rather flustered due to Rarity’s response, and he tried to chuckle nervously while looking away from her with a shaky smile. “I-I mean, I… I do tend to swing both ways, and I… I’ve been wanting to feel a stallion with a girth that matches my own, you know?”

Even though she was still rightfully surprised by Quill’s answer, Rarity only needed a brief moment before growing a more understanding smile. “Ohhhhhh… So that’s why you purchased all those dresses from me over the past few months~”

Quill’s blush deepened as he giggled with a bashful smile, and gave a light shrug in confirmation. “W-Well, it certainly wasn’t for any marefriends, that’s for sure. Heh heh heh…”

“Honestly, that’s quite a relief,” noted the unicorn as she lit up her horn, and trotted towards her dresser to look through her personal items. “I might be a lot of things, but I’d rather not be labeled as a ‘Home-Wrecker’ for sleeping with a stallion who’s already taken.”

“Yeah, no doubt,” he nodded while watching her look through her drawers, unsure of what she may have been searching for. “I heard about that Raspberry Mousse incident with Spike.”

“Ugh, do not remind me of that mare, please…” Rarity grimaced to herself while her magic opened up several of the drawers, and various delicates were floated aside so she could find her more hidden items underneath. “Now, let me see… Hmmm… Aha! Here we are…”

Rarity may have looked miffed for a brief second when he mentioned Raspberry Mousse, but her face lit up excitedly when she floated out something from her middle drawer. “I knew I had it in here~”

She then turned back around to face Quill, who was looking slightly confused while Rarity rummaged through her dresser. However, his eyes widened in surprise the moment he saw what was floating in her blue aura: A thick, bulging butt-plug that was made of glossy black silicone.

“Yes, this looks to be the right size~” she murred to herself while marveling at the sheer girth of that plug, which would’ve likely sent any virgin stallions running for the hills. But for Winter Quill, his gaping muzzle indicated a much different reaction to seeing such a dauntingly big toy. But before he could try to ask any questions, Rarity smirked at him while the plug floated in the air between them. “Now then… When you say you want to be made looser, is that something you truly wish to accomplish?~”

Winter had no idea how to respond to such a question, mostly since he wouldn’t have fathomed Rarity accepting it so easily. But as his cheeks became heavier with blush, and his eyes locked onto that girthy plug, he let out a weak shudder before biting his lip and nodding his head. “Ummm… Y-Yeah~” he said before growing a nervous smile. “I… I’ve really been wanting to get a good stretch, you know?~”

“Indeed I do~” Rarity then trotted up towards him, and also floated out a large bottle of lube to levitate alongside the plug in her aura. “And I also know of a rather… unorthodox means to achieve such a goal. But if you’re serious about doing this, I need to emphasize two important things…”

Winter tried to nod his head, but his brows rose up when Rarity walked right past him while holding her items. Without warning, the mare lifted up his tail with a hoof, and got right behind him while continuing to speak. “First of all,” she began while pouring a generous amount of lubricant to the tip of that thick plug, which dribbled down the length of the toy to make it shimmer brightly, “I need your word as a gentlecolt and as a friend that no matter what happens, you will not disclose our activities to anypony. This is just as big of a secret for me as it is for you, and I need to know that you won’t break my trust on this matter.”

It was hard for Quill to really focus on Rarity’s insistence when he glanced back at her, and saw how large that plug looked right beside his waiting hole. But upon seeing how tremendously big it really was, a guilty shiver crept across his back before he nodded his head. “A-Absolutely, Rarity,” he said without hesitation or insincerity. He even brought up a hoof to recite the famous, “Cross my heart, hope to fly, stick a cupcake in my eye. I promise this will stay between us.”

“Thank you~” she said, before she made a quick, “Oh, and before I continue with this, do you have any errands to finish today?”

Even though that question should’ve been asked sooner, Quill was happy to shake his head with a smile. “Nope. My schedule’s free today~”

“Marvelous!” She then elicited a sharp gasp from the stallion the moment she pressed that thick tip against his tailhole, and started to prod it with the aid of her magic. “N-Now then… Nnnghhh… In order to give you what you want, we would need to visit my ‘Associates’ at a discrete location. I’ll also need to blindfold you as well for your own safety, but this will be a fun addition to emphasize how seriously you want this~”

Since this wasn’t his first time getting his butt played with, Winter Quill was able to listen to enough of Rarity's words to nod accordingly. However, as the mare’s pushing grew harder to counteract the plug’s widening girth, it didn’t take long for Quill to start groaning through gritted teeth. He ended up bending himself downward while his tail was flagged up, and he kept himself in place while Rarity continued with her work. Even though she didn’t even ask him first before getting the plug in, Winter wasn’t one to complain about getting a good stuffing. Not to mention, despite how recently he finished inside of her, his cock was already twitching curiously to what the kinky seamstress was planning. “Mnnnghhhh… U-Understood, Rarity. I-Aaahhhh!!~”

“Sorry, Winter,” said the mare with a remorseful wince as she paused her pushing the tiniest bit. “I just wanted to make sure this got in before we went out. Would you rather I try something else?”

Despite how badly his tailhole stung from that last push she gave, Quill immediately shook his head while his eyes were clenched shut. “I’ll be fine, I’ll be fine. I-I just… It’s been a while…”

After taking a deep breath, Winter Quill tried to rest his chin on the floor while keeping himself presented. “Okay… Okay, keep going~”

Rarity grew an impressed smirk, and nodded accordingly. “Lovely~”

The mare made sure to keep note of Winter’s pained groans when she resumed her pushing, but was fortunate to see how strong his resolve really was. Even when Rarity used her hoof to press down on the base, which caused Quill’s puckering hole to stretch out even wider around the plug’s enlarging girth, the stallion’s strained grimace wasn’t enough to overpower his lustful moans. Not to mention, Rarity was able to get a good view of his cock growing erect with every push she made, which prompted her to keep going with an eager grin.

“Nnnnngggg… You like that, Mister Quill?~” she asked teasingly while sporting a seductive grin. “Because I can guarantee you that the friends I know are just as thick as that plug right now~”

“Aaaahhhh!!~” Winter trembled like a fallen leaf while convulsing on the floor, and had to cover his muzzle with both hooves to keep from moaning too loudly. But alas, before he could even think of giving an affirmative response to her statement, Winter’s fur stood up on end the moment he heard a distinct pop, followed by a strong feeling of relief that caused him to moan out eleatedly. “Ooooohhhhh~ Ohhhh, wow that’s thick…”

Rarity huffed with a satisfied smirk, and pulled back from Winter’s rump while that thick base was firmly lodged between his cheeks. She was surprised that he was able to take a plug that thick without much complaint, but she couldn’t have been happier with the end result either. “Well, hopefully that’ll provide you with some adequate preparation before we head off~” she noted with a cheeky tilt of her head. “Are you able to walk?”

Winter had to take a couple shaky breaths following that intense stretching, but he was able to nod weakly before pulling himself back on his hooves. His legs may have been quivering while that massive plug was stuffed inside of his hole, but his erect cock was still twitching antsily due to how hard his prostate was being hit. And as he looked back at Rarity, his smile couldn’t have been more reassuring as he said with a brief exhale, “W-Well, uhhh… hopefully ponies won’t notice how wide my gait is when I try~”

“Ohhhh, don’t you worry about that, Darling~” As she grew a more devilish grin, Rarity motioned for him to follow her as she went to exit the bedroom. Meanwhile, her tail was still lifted up to show off her gaping pussy, which prompted her to glance back at Quill and say, “As soon as we’re finished, I have a feeling ponies will be noticing you for how loose you’ll be~”

Even though that thought should’ve been seen as a warning, all that Winter could do was blush with a thankful smile, and a firm nod of his head. “I… I really hope so~” he said while grinning nervously, which caused Rarity to chuckle in delight.

True to her word, Rarity was quick to escort Winter Quill through Ponyville with a casual demeanor, even though the stallion had to waddle a bit with the thick plug in his ass. Fortunately though, Rarity’s presence helped to pull most of the focus away from Quill, as her natural beauty shone through on that beautiful day. The mare wasn’t shameless enough to keep her tail flagged up when they went outside, but she wasn’t against shooting a few lustful winks to various stallions the two trotted past. She even coaxed Winter Quill into doing the same, which was both embarrassing and invigorating at the same time.

As soon as the two exited Ponyville’s town limits, Rarity waited until they were alone to fasten a blindfold over his eyes. Because of that, Winter Quill was left completely at the unicorn’s mercy as she continued their trek with him closely in tow. He had no idea how long they walked across unfamiliar terrain, but he could feel the dirt road disappearing underneath his hooves to be replaced with grass. After a while, that grass turned to what felt like coarse rocks and unpaved dirt. Part of him wanted to ask where they were going, but the mare’s cheerful conversations with him helped to distract his looming worries.

The two eventually trotted through some old mining tunnels, with Quill growing more apprehensive when he felt the air growing more brisk around them. Fortunately for the two, Rarity wasn’t met by any looky-loos as she led the way through the tight, hidden crevasse of the Diamond Dog caverns. Ever since she began her business ties with them, she was given free access to one of their hidden tunnels in exchange for anonymity. Even though the dogs had no idea who she really was, the entryway towards her personal cavern/bedroom was always left open as an invitation for some carnal delights.

“Nnnffff~” Winter couldn’t stop fidgeting while waddling behind Rarity, mostly due to how intensely that butt-plug was rocking his insides with every step he took. His cock may have still been rock-hard (which he was shocked didn’t elicit any gawking stares back in Ponyville), but his expression was fairly uncomfortable beneath his mask. “Uhhh… Are we close, Rarity?” he asked in a meager tone of voice. “I’m not sure how much longer I can walk around with this thing in me.”

“Just a couple more steps,” chirped Rarity cheerfully, as she found herself right before the metal doors that lead to her room. She floated out a small brass key she had on a chain, and used it to unlock the door only she had access to. When she entered, she sighed blissfully upon seeing the lavish space untouched since the last time she was here. Even though the room was technically just a small cavern opening with rocky walls and no windows, the Diamond Dogs did a lot to make the space more accomodating for their breeding bitches.

When she finally undid his blindfold after closing the door behind them, she stepped back with a prideful smile while showing off her location. “Ta-daa!!~ I’ll admit it’s not the most standard lodgings, but I have a feeling you’ll appreciate it nonetheless~”

Winter really was impressed when he readjusted to the light from the various lamps across the walls. After blinking a couple times, his jaw dropped the moment he took in the sight of the secret room. It may have been a cave, but his eyes were immediately drawn towards the massive shelf of sex toys standing beside the king-sized (and thankfully clean) bed. There was also a row of closed shelf doors waiting at the other side of the room, each one carrying little knobs so the two could open them up.

“Wait a minute…” Despite how nice the underground sex-room may have looked, Winter had to look around before asking in surprise, “Is… is this the Diamond Dog caves?”

“Well, now you know why I wanted to keep this a secret, right?” Before Quill could nod his head, Rarity was already trotting towards those doors with an eager smile on her muzzle, “I’ve made an arrangement with these gentlemen in regards to my business. Their workers are in need of consistent relief due to the lack of females, so I offered them the services of an ‘Unnamed pony’ willing to visit them regularly for attention. And in exchange, I’m given a generous discount of their gems for my dresses!”

“Ohhhh…” Winter may have been surprised that somepony like Rarity was slutting herself for Diamond Dogs (especially since he knew she was once kidnapped by them), but her casual explanation of things prompted him to smile in understanding. “Okay, I think I get it now. Did you seek them yourself, or…”

Rarity paused a bit as she reached one of the cubby doors, and skewed her muzzle before answering, “Well… let’s just say that Spike can be very persuasive when it comes to overcoming prudishness. And it’s not just myself either~”

That detail caught Quill’s attention with a sharp raise of his brows; however, Rarity refrained from saying anything more than that, and he was smart enough to tell she wasn’t going to out whomever else had been down here like himself. So instead, Winter continued to look around the closed-off room while trotting up to her. “And… you seriously come here by yourself? I mean, I wouldn’t have guessed you’d step a hoof here.”

“Again, Spike has his ways~” she noted with a coy smirk back at him. “Not to mention, the Diamond Dogs really aren’t that bad. Their business dealings are completely professional, and all of their workers are regularly tested. These might not appear to be safe, but they’re safe enough for my approval.”

To emphasize that point, Rarity opened up the little cubby door she was at, which revealed a large hole large enough to fit Winter’s hoof. Of course, considering it was right at waist-level from the floor, Quill didn’t need to ask what that hole was meant for. Instead, he could only blush with a wide-eyed expression as he saw the fashionista turn herself around without hesitation. And as she faced the stallion with a confident smirk, she only needed to give the wall a couple hard kicks with her hoof before backing up, and pressing her marehood right up against the open hole. “Mnnnnghhhh… And with that, all we have to do is wait~”

Winter Quill’s face was deeply blushed as he saw Rarity pressing up against that opening in the wall, and shuddering anstily for whomever might come up to use her without question. Due to how surprising it was to witness the posh mare in such a raunchy position, the stallion almost forgot about his thick plug that was still imbedded inside of him. But alas, as his cock repeatedly smacked against the underside of his barrel, he ended up squirming a bit as he watched her with a bitten lip. Meanwhile, the mare was narrowing her eyes on him with a waiting smirk, and motioned her head towards one of the still-closed cubby doors beside her. “If you want,” she said with a lighthearted shrug, “I wouldn’t mind if you wanted to see how well I can handle these brutes~ If anything, it might help you better assess whether or not you wa--OOHHH!!~”

Since she was speaking out-loud, neither her or Winter were able to hear the low and lustful growl that emanated from the other side of the wall. Of course, as soon as the mare jolted up with her fur sticking out, Winter Quill’s eyes widened when he realized somebody had already taken notice of the available hole. His blush deepened when he saw how quickly Rarity’s eyes rolled back with a giddy expression on her face. And as she quivered with an audible moan, he could hear through the other side of the cave wall, “Oh, sweet! HEY GUYS, THE BITCH IS BACK FOR MORE!!~”

A strong shiver crept up Winter’s spine when he heard an uproar of elated howls and whistles through the wall, indicating that these Diamond Dogs were going to be eager to rut whomever has their orifices on display. And in the case of Rarity, who had to light up her horn so her magic could help brace her against the ground, her eyes clenched shut when she belted out a shivering groan. Meanwhile on the other side of the wall, the mare’s presented pussy was already being put to use as a random Diamond Dog’s thick, meaty cock went up to grind hard between her puffy lips.

“NNNGHHH!!!” As she felt that hot piece of cockmeat beginning to slip inside of her, undoubtedly becoming slathered with the remains of Winter Quill’s earlier load, her hooves clenched tightly against the carpeted ground beneath her. “Ohmigosh, that’s quick! Mnnnghhh… Oooohhhhh that’s nice…”

Even though the mare was still able to speak coherently, Winter didn’t need to look through the wall to tell that whatever was being shoved inside of her was hitting allllll of the right buttons. He had heard about the girth of Diamond Dog cocks, and even fantasized about it countless times on lonely nights; but at the same time, he never thought he’d get the opportunity to actually witness the action up close. Even as Rarity began to moan out louder, and her hind-legs trembled from every plump inch of that doggy cock working its way inside of her, it was hard for Mister Quill to keep his hooves still for long. Eventually, the stallion found himself moving forward without realizing it, and heading towards one of the available slots himself.

“AAAAHHHH!!” Rarity’s head reeled back after moaning from something especially tantalizing, which was apparently big enough to make her hips writhe against the wall. “Ohhhhhh, there's the knot!!~ Yes!! YES!!!~”

As Winter Quill paused to stare at Rarity in jealous awe, the mare’s loose cunt was being put through another intense stretching as that Diamond Dog knot pressed up against her waiting entrance. Even though the mare had established herself as a slut for a while, and was currently clenching around at least eight inches of throbbing hot cock, she was still leaking profusely around that meaty knot grinding up against her lips. Unlike most stallions back in Ponyville, the canine didn’t try to take it slow as he growled ravenously, and repeatedly tried to push himself through her previously tight crevice. And even with all the cocks she was pleased to service in the caves and back at home, that plump bulb of cockmeat still stretched her pussy out to its limits while the mare reeled in utter bliss. “AAAAHHHH!! Oh, YES!!~ Mmmmm… Oh Winter, you have to get in on this!!~ NNFFF!!”

Despite how nervous he may have felt about obliging, the stallion didn’t need to be given that suggestion twice. Instead, Winter Quill antsily trotted over towards one of the closed cubby doors, and went to unlock it while his butt-plug was still lodged inside his ass. Fortunately though, Winter seemed more keen on trying something else; much to Rarity’s surprise, the moment he opened that cubby to reveal a similar hoof-sized hole in the wall, Winter Quill let out an excited shudder before shoving his muzzle through the opening.

“Oooohhhh~” Rarity was busy straining around the girth of her knot, but she still smiled in approval at Winter’s boldness. “W-Wonderful alternative, if I say so mys--AAAAHHH!!”

Before she could finish her compliment, Rarity gasped with a pained shriek the moment that dog behind her gave an especially hard thrust of his hips. His knot may have been the size of a soda can, but he was able to cram it through the slut’s opening and leave her moaning in ecstasy. Meanwhile, one of the other Diamond Dogs was quick to take notice of the stallion’s muzzle that poked its way through one of the other available holes. “Oh shit, there’s another slut here today!~”

Winter could hear that gravely voice through the wall, but couldn’t see through the hole while his muzzle was stuffed through it. Because of that, he could only shudder in anticipation, not having any idea who would be using his mouth like a fleshlight. Part of him wanted to be worried about his identity being revealed too easily with having half his face exposed, or even being identified as a male and pissing off the dogs; however, considering what Rarity told him, he could only assume that they wouldn’t mind since they fucked Spike without complaint. So instead of worrying about homophobic panic, all that Winter Quill did was open his muzzle wide, and stuck out his tongue right before feeling a thick cock cramming itself between his lips.

“Mnnnghhh!!~” The burly canine thrusted his hips hard as he plowed himself inside of that open maw, not caring one bit about whether or not he’d choke the poor stallion. Fortunately for Winter Quill, his previous experience helped to prepare him as he took a deep breath, and kept his throat relaxed for that thick cock plunging towards the back. His eyes instantly rolled back when he caught the extremely strong musky flavor, which hit his tastebuds badly enough to nearly sting a little. Meanwhile, Rarity’s moans faltered the slightest bit when she caught sight of the thick bulge that protruded from Winter’s throat.

“O-Oh my!” exclaimed the mare while shivering hard, her hooves still curled up tightly from that plump knot pulsating inside of her. “Nnnnfff~ I would’ve guessed you… th-that you would take it from the other end first! Hehehe~”

Even though he caught enough of Rarity’s opinion for his ears to twitch a little, he still hummed contentedly while trying to suckle around the girth of that thick doggy cock flooding his muzzle. The canine’s plump knot was pressing up hard against his lips, but it was impossible for it to go into his mouth while his jaw was open at its widest. Still though, the stallion was rock-hard while sucking the Diamond Dog off, which caused his aching hole to clench hard around his plug. Even though he wanted to take it out to really get himself stretched-out, it was hard for him to focus when he heard the dog through the wall murr, “Mnnnghhh… You’re a good little cocksucker, aren’cha?~”

Due to how blissfully overwhelmed he felt from the heavy spurts of doggy pre shooting down his throat, Winter would’ve likely pulled himself back so he could beg for more. But even with how horny he was getting from the brutal treatment he was receiving, he couldn’t think to stop the onslaught for even a second to state the obvious. He was already down here with the fashionista slut beside him, and he wasn’t willing to let up after getting that first taste. So as he continued to let that meaty cock piston in and out of his throat, he could only let out a muffled “Mmhmm~” before lighting up his horn.

Rarity saw the base of Winter’s plug being enveloped with his aura, even though his horn flickered a bit from his tantalized state affecting his focus. Nevertheless, he still groaned hard around that cock in his mouth while his own member twitched helplessly underneath him. He tried to pull back as best as he could with his magic, but it was proving difficult for him to dislodge that massive plug while continuously clenching around its girth. Fortunately, even with how stuffed the mare may have been with her own helping of Diamond Dog D, Rarity was able to light up her own horn to assist in Winter’s dislodging. “Nnnnffffff… O-Oh, goodness this is difficult…”

Fortunately for the two unicorns, their joint efforts were more than enough to get a good grip of that plug. Unfortunately, due to how flustered both of them were getting while stuffed with cock, neither of them could yank on it with any subtlety or gradual movements. Instead, Winter’s butt-plug was tactlessly tanked out with a wet pop, as well as a muffled shriek from the cocksucking stallion. The stinging pain was intense enough to leave his eyes clenched tightly shut, but he was thankfully able to keep his muzzle from doing the same. Meanwhile, his tail was twitching antsy due to the cold air that brushed against the oversensitive flesh of his massive, throbbing gape.

“Aaaahhhh!!~” Rarity moaned out when she caught sight of Winter’s stretched-out hole, and her eyelids fluttered before feeling the Diamond Dog behind her beginning to thrust into her needy cunt. “M-My goodness, Winter! Mmmmm… Oh, you’re going to love those knots in you, I can already tell!~”

Winter already knew that fact himself, which prompted him to moan out while slathering his tongue all over that musky doggy cock. But as he heard Rarity’s lustful groans intensifying in tandem with her canine’s thrusts, it didn’t take long for the stallion’s envy to warrant a change of position. By the time he finally slipped that canine cock out of his mouth, thick strings of saliva and pre connected his panting muzzle with the dog’s pointed cockhead. And as the brute yelled out, “Hey, what gives?!” through the other side of the wall, Winter Quill quickly whipped himself around and pushed his rear up against the open hole.

“NNNNGHHH!!” Winter’s eyes shot wide-open the moment he pressed up against the wall, and his strained jolt caught Rarity’s attention promptly. When she looked over at his positioning, her brows rose up when she realized the stallion’s cock wasn’t visible from her position. Meanwhile, Winter was struggling not to wince in response to his accidental thrust backwards, which somehow shoved his cock and balls through the hole before his ass. Even though his gaping hole was sticking out the other side of the wall for open use, his throbbing horsecock was helplessly pulled back and twitching against the wall for whomever was there to see.

“Oh shit, this is a guy!” shouted a raspy voice from some canine on the other side of the wall. “You still gonna fuck it?”

“You see how loose that fruit is? I’d be stupid NOT to ruin it more~”

Winter wanted to moan out from that Diamond Dog’s foreboding line; however, his heart skipped a beat the moment he heard another voice chuckle with a teasing jeer.

“Heh~ Look at how measly that thing is! It doesn’t even have a knot!”

“Yeah, I know, right? No wonder ponies have to come down here for a good dickin’~”

“Dawww, look at the tiny thing trying to cum! It’s like a baby snake spitting up!”

“Ha! You think all stallions are that puny?~”

“Probably. I bet fags like him need to bottom just because of that~”

Rarity may have looked uncomfortable with the canines’ insulting remarks (mostly since she was willing to vehemently defend Winter’s equipment if asked), but she kept herself silent on the matter when she got a good look at Winter’s blushing face. The pony was wide-eyed with a deeply embarrassed expression, but the corners of his muzzle were curling upward to show a more bashful response to the dogs’ insults. Considering how well-endowed most ponies saw him, the idea of having his cock mocked by these grangly mutts was strangely refreshing for the stallion. In fact, as he heard three or four Diamond Dogs laughing at his cock, he could only throb hard through the wall while moaning out in dire need for a real cock to use him for a change.

“Welp, since the queer already got it nice and wet!”

“MMNNNNGHHHH!!!~” Winter Quill’s eyes shot to the size of dinner plates, and his body locked-up tightly in response to that thick cock skewering his gape without warning. The canine’s plump, meaty head sunk deep into his hole, and Winter was left reeling with a shaky groan as he tried to clench around the brute’s shaft. Even though that plug loosened him up enough to make his clenching worthless, it wasn’t until he felt the plump knot pressing up against him that he felt something substantial. His nerves were already tingling on end with every hot pulsation of that doggy cock grinding up against his sensitive walls; but the moment he heard a low and ravenous growl from the dog on the other side of the wall, he only had a second to take a quick breath before he felt that knot’s pressure beginning to build up. “Aaaahhhh!!!~”

Much like Rarity, who was already becoming lost in her own lust while enduring her canine’s hefty thrusts, Winter Quill was left reeling in ecstasy when he felt his tailhole stretching out further than before. Despite how much that plug opened him up, the pony’s eyes struggled to stay open while feeling how much thicker that first knot was. His loosened hole still showed a lot of resistance as the canine grunted with every hard push he made, which caused his cock to throb more prominently with the shaft already slipping deeper inside of Quill. But alas, despite how tightly his straining ring tried to resist the building pressure, Winter eventually belted out a deep and pained cry the moment he felt his tailhole being forced open with a hard pop. “GNAAAHHH!!~”

The stallion trembled and fidgeted like mad while braced up against the wall, unable to pull forward due to the knot and his own cock pinning him into the glory hole. The intense pain and discomfort from his backside was leaving his voice notably strained, but his stallionhood continued to throb and leak steadily among the sounds of the canines’ mocking jeers. And even with how badly his hole was stinging after being given such a brutal stretching, Winter could only moan out lustfully when he felt the Diamond Dog already thrusting into his soon-so-be-cumdump of a hole.

“Mnnnghhh~ Holy fuck he’s needy! He didn’t even flinch when I got the knot in~”

“Heh~ You really surprised? That little cock’s holding him in like a kickstand!”

“I don’t give a shit, I’m fuckin’ that hole next!”

“Me too!~”

Winter’s eyes rolled back as he grew a half-lidded expression, and his dreamy smile emphasized just how much he was loving this treatment. The Diamond Dogs may have been keen on ruining his hole while he was pinned against the glory hole, but Winter couldn’t have asked for anything different if he tried. Not to mention, as his body began to rock back and forth in response to the canine thrusting into his ass, it was hard for him to even think of resisting while moaning like a mare in heat.

“AAAAHHHHH!!!~”

Speaking of mares, Rarity’s contented shriek of rapture prompted Winter to glance over at her while moaning weakly himself. Even as he felt so much hot, pulsating cockmeat repeatedly tugging against the inside of his hole, his eyes widened the moment he saw Rarity’s climactic stance. The mare was reeling in pleasure while bracing herself as tightly as possible against the wall, and the elated shivers of her body made it obvious what had just happened. Meanwhile just between her trembling legs, Rarity’s stomach began to swell out a little as she felt a volley of hot, gooey canine cum flooding her insides and claiming her womb.

“Oh Goddess yes! Y-YES!!~” Rarity reeled her head back while shrieking to herself excitedly, with drool deeping from her open muzzle without a care in the world. Winter Quill had no idea how much she took from that first cock, but he bit his lip in jealousy when he saw how swollen she was getting past her barrel. Given how thick those Diamond Dog knots really were, he expected for the mare to be pinned against the wall for a while before the canine could pull out; but much to his shock (and unrelenting approval given his own desires), he gasped when he heard an audible pop through the other end of the wall, as well as Rarity’s strained cry in response to him pulling out his knot. “AIEEEE!! Ahhhhh!! Mmmnnnghhhhh…”

Rarity clenched her eyes shut and shuddered painfully, all while keeping her ruined pussy tightly braced against the wall. On the other end, many of the canines coming in were barking and growling in approval of the mare’s opening being severely stretched-open from that knot. And as heavy trickles of cum oozed out from her cunt and dribbled down the wall, her hooves could only clench the carpet beneath her while savoring their teasing cackles. “Aaaahhhhh… S… S-Sweet mother of Celestia that was--AAAAHHHHH!!!~”

Before she could even finish her exclamation, Rarity shrieked out once more as a different Diamond Dog went in and shoved his cock inside of her creampied hole. Even though she was wincing painfully, Winter Quill was able to see the elated look on her face as she went right back to being used. And as she started to moan out once more from the intense stretching that her cum-drenched folds were experiencing, her stallion was reeling right beside her while being rocked back and forth against the wall.

“AAAAHHHH!!” Winter Quill’s eyes were clenching as tightly as his teeth, and he could feel his cock throbbing close to the point of climax. Fortunately for the slutty stallion, he could also feel the distinct pulsations of that rigid cock inside of him to indicate that he wasn’t alone. He had no idea how much longer this Diamond Dog would be rutting him so mercilessly, or even how many others were waiting to use him as soon as he was finished; but at the same time, the idea of that canine ripping his knot out and leaving him completely gaped for public use caused his heart to thunder like crazy inside of his chest. And by the time that merciless mutt finally did reach his peak, the only way that Winter Quill was able to know was from how tightly those heavy balls pressed up against his own to churn all that hot doggy cum.

“AAAAAAHHHHH!!!~” Much like Rarity, Quill’s head pulled back as he belted out a heavy cry, and spasmed like mad from the blast of warmth that flooded his insides. His own cock couldn’t take it, and he ended up spurting multiple ropes of his seed over on the other side of the wall. Even though he could hear multiple canines cackling like hyenas and making remarks about his “pathetic” load, Winter could barely process anything while reeling from the sheer volume of cum that shot into his deepest depths. Even though his hole had been stretched out to an insane degree, the plugging from that meaty knot ensured that most of that first load settled in deep to help weigh down his slightly swollen gut. “Nnnnnnngggggg… Ohmigosh…~”

“I know, right?~” remarked Rarity between her heated breaths, already getting herself ready for another filling as she rocked back against the second knot with every thrust delivered to her. “Ahhh!!~ Just wait until you take your third or forth knot in a row~”

Winter shivered blissfully to such an idea, even though he had no idea how much more he could take after that one cock alone. “Ooooh, that sounds really ni--GYAAAHHH!!!”

POP!!~

As soon as that canine pulled out his knot with great force, Winter Quill’s gape almost turned to a blossom from how brutally his hole was stretched outward. A heavy torrent of cum was gushing out from his overused hole, and caused him to dribble like a schoolgirl pissing herself in front of a pack of bullies. But even as he overheard the mocking laughter from the Diamond Dogs pointing at his ruined backside, he wasn’t able to call out for more before his wishes were granted. He was barely able to focus due to the blinding pain that followed that merciless pop, but the euphoric feelings rushed right back in when he felt a new cock plunging itself inside to keep his bowels flooded in cum. “AAAHHHH!!~”

Winter wished that he could better process what was happening, just so he could appreciate every hard and relentless thrust that bombarded his hole from the pack of hungry mutts behind him. But as his eyes rolled back, and his muzzle hung open to begin drooling, the moaning stallion found himself becoming enveloped in a deep and lustful high he didn’t want to come down from. Rarity was appearing to slip into a similar state, as her voice became weaker and incomprehensible from the barrage of titillation her poor cunny was enduring. Part of Quill’s conscience wanted him to stay conscious for as long as he could, mostly so he could know precisely when his holke would be gaped enough to his liking; but as those strong poundings continued on, and the two pony sluts were left writhing in mutual pleasure from their orifices being wrecked beyond repair, Winter Quill’s state of mind only grew more clouded from every thrust he was being given, and every intense stretching that came from those plump doggy knots.

Winter Quill had no idea how many of the Diamond Dogs used his and Rarity’s holes that day, as he ended up blacking out by the time his third knot was being shoved into him. But much to his unbridled delight, the stallion couldn’t say he felt any remorse by the time he finally reemerged from his cock-drunk stupor much later in the day. Fortunately for himself and Rarity, there happened to be a private bathroom that they could use to clean themselves off following their multi-hour long session spent together. Even though the shower drain nearly clogged a couple times from the obscene amount of cum that matted their fur across their backsides, Winter still shivered in pure contentment by the time he saw how absolutely loose he had become in the mirror.

Even though he wasn’t exactly tight before, Winter would’ve sworn he could’ve taken an entire hoof up his ass when he looked back and saw that tremendous gape. His tailhole was sagging badly enough to look like a tube sock was emerging from beneath his tail, but he couldn’t have minded that sight any less. Not to mention, even after cleaning himself out for over half an hour, there were still the slightest trickles of Diamond Dog cum that seeped from his wrecked opening. He could only imagine how many loads he actually took, or how much more cum was pooled up inside of him to leave his gut still slightly swollen; fortunately though, even with how overused he may have gotten, Quill was happy to learn that Rarity’s butt-plug was still thick enough to remain firmly lodged in his ass to keep his belly nice and full of splooge.

“Aaaahhhh…” Rarity sighed blissfully to herself while slathering her mane with shampoo with the aid of her magic. While she and Winter shared the shower head to cleanse their bodies of their debaucherous acts, the mare didn’t seem to mind one bit how severely her pussy was sagging and leaking with cum. “It’s such a refreshing experience to share with somepony other than myself~”

Winter could only sigh with an affirmative nod, and tried his hardest not to shudder every time he felt his hole trying to clench around his plug. “Mnnghhh… Y-Yeah, I get what you mean, Rarity. And, uhhhh...”

Rarity glanced over at the stallion after hearing his brief pause. Meanwhile, Winter Quill was blushing hard before looking back at her with a warm smile. “... I just wanted to say… thank you so much for inviting me here~”

The mare gave an equally gracious smile back at him, before leaning in to give Winter a much-needed hug. “Dawww~ You don’t have to thank me, Darling. If anything, I should be thanking you for helping me out with all those dogs. Hehehe~”

Winter chuckled alongside Rarity’s enamored giggled, but he was still blushing while he and Rarity finished cleaning themselves up. Of course, by the time the two went back to the main room, their brows rose up in unison when they saw something had been left on the bed. Rarity went up to investigate the small wrapped box, and was quick to smile while saying, “Ooooh~ Oh, Winter…”

She lit up her horn, and floated the gift box towards him with a devilish grin. “I think you really made an impression back there~”

When Winter Quill opened up the box with his own aura, he gasped when he saw the two small items within: One was a brand new dog collar, which was colored a hot pink with black studs along the faux leather. And just underneath that collar, Quill found a small note that was crudely written with a pencil by one of the Diamond Dogs.

Enjoy your present, you little cock-sucker. If you come back for more, we’ll be sure to make a tag of your liking. ;)

Sincerely, Rover

Winter’s ass may have been hurting like hell, and his balls were aching from how many times he came from that afternoon alone; but alas, the stallion didn’t even hesitate to put his new collar on while saying, “Well… Hopefully I’ll have a good tag idea in mind by the time I come back tomorrow~”