Discord's Tournament of Champions: Round One - Fluttershy vs. Loona

by TheVClaw

Rating: mature
Tags: My Little Pony: Friendship is Magic, Other, Fluttershy, Porn, Sex, Fetish, Profanity, Random, Crossover, Narcotics
Length: 9011

Discord's twisted plans have just begun, and his best friend is about to face off against the Hellhound Loona from 'Helluva Boss'. How will Fluttershy face off against a literal canine from hell? Well... let's just say that Loona should watch out~ ;)

Fluttershy, as well as all her fellow Element friends, have all agreed to take part in Discord's unconventional mission. In order to protect their friend's virginity, the five mares plan to square off against the pre-selected 'Waifus' Discord warned them about. If they succeed, then Twilight would remain safe while staying at the top of the Multi-Dimensional ranking known as "R-34". None of the details made much sense to any of them, but that didn't matter when it came to protecting their Alicorn friend.

Because of that, Fluttershy decided to show her courage by going into the first face-off. Much to Discord's shock and intrigue, the animal caretaker decided to square off against Loona, a literal Hellhound beast from the universe of 'Helluva Boss'. She had no idea what she would encounter in Discord's pre-made and neutral world, but she was determined to give everything she had for Twilight's sake. Luckily for the pegasus, it seems that Loona is just about to need a quick Pit-Stop out in the middle of nowhere...

Note: This story is an official entry in the Furry Foray Festival Contest on FimFiction. This story is also featured on my FurAffinity account here: https://www.furaffinity.net/view/51168624/

Published 2023-02-26 21:30:02 UTC
Last updated 2023-02-26 21:30:02 UTC

The Not-So Itsy-Bitsy Spider

Meanwhile, in a completely different unknown location…

“GAH!! Fuck me with a rusty fucking screwdriver!”

Her long muzzle clenched into a viscous-looking sneer, while her blood-red eyes narrowed down at her device with pure rage. If looks could kill, her phone would’ve been completely vaporized and left as a pile of dust on the ground. Unfortunately, despite how pissed off she may have looked, it wasn’t enough to find even a single bar for her wifi to pick up. Even when her paw swiped down on the screen ten times in a row, each refresh indicated that her web browser wasn’t able to load up.

“GOD FUCKING DAMMIT!” She threw up her arm in frustration, but paused before following through with destroying her phone. Even though she was seething furiously, she refused to drop or unclench her paw. After a couple seconds of strenuous groaning, the canine sighed in defeat and lowered her arm. She took a moment to glance down at her phone, and pouted when she saw the deep scratch line that went down the middle of her screen; apparently during her frantic refreshing, she forgot to retract her claws.

“Aww, shit,” she muttered with a more regretful tone. She cringed and pinched the bridge of her muzzle so she could calm herself down. “Oh man… This is the third screen this month.”

She took a moment to turn her phone on and inspect the damage. Luckily for her sake, the phone itself was still fully functional (aside from the nonexistent wifi), but that scratch was impossible to ignore. She groaned once more before turning off the screen, not wanting to see that any more than necessary. Since her tight spandex shorts had no pockets, she tucked the phone inside the waistband in the front.

“Nnnghh!!” She shivered hard enough for the silver fur on her shoulders to stand on end for a moment. She may have been used to placing her phone there for emergencies, but she clearly forgot that she decided to go commando that day. The cold plastic of the phone’s back covering pressed up particularly hard against her crotch, but not enough to make her try a different option. After shuddering from the slight discomfort, she sighed with a grimace and looked around with her arms crossed over her chest.

Fortunately the Hellhound, the back of the rest stop was still completely empty, save for a few trashcans and a nearby dumpster. She had hoped that she could get some reception outside the building, but that ‘No Signal’ sign on the front proved to be telling the truth. With her contacts still over an hour away, all she could do was groan and lean her head back as she walked around to the front again. “Fuck…”

The “rest-stop,” which was literally just a small brick building with two bathrooms and a locked closet, was out in the middle of nowhere with no other amenities nearby. The worn-down road seemed to scan out for eternity from both sides, which made the region feel far more isolated. The only positive was that there were a few vending machines on the side of the building; but even then, the canine only had enough spare change to buy a pack of gum. She sat down on the wooden bench at the front, and dug into her shorts to pull out her phone. After wiping the back with her paw, she decided to check her messages for any updates:

‘Loona, you there?’

‘... hello?’

‘Where did you go?!’

‘Blitzo is getting angry’

‘... now Millie’s angry too!’

‘LOONA, WHERE THE F*CK ARE YOU?!’

‘LOL, you censor your texts?’

‘WHERE ARE YOU?!?’

‘van broke down’

‘FOR REAL?’

‘HOW?!’

‘I dunno’

‘YOU DON’T KNOW???’

‘I’m not a mechanic, dipshit’

‘lOONA, i NEED AN ANSER’

‘Check your caps lock’

‘*Answer’

That was the last message she received from the contact labeled ‘Cuck Bitch’. Since there were no updates, she could only assume that Moxxie had to pull away from his phone. She then went to check the messages between herself and Millie

‘Moxxie is crying. What did you do?’

‘Nothing’

‘Alright, just checking :P’

‘Okay, Blitzo read the texts and has your location pinged’

‘What actually happened with the van?’

‘I said I dunno’

‘Well, where were you when it happened?’

‘A few miles from the gas station’

‘It just started smoking and the engine turned off’

‘...’

‘Loona, did you pump the gas?’

‘Yeah. Why?’

‘What color was the pump handle?’

‘How the fuck should I know?’

‘Uhhh, green I think’

‘Why?’

Once again, that was the last message she received while walking down the side of the road. By the time she arrived at this rest stop, the signal was completely dead. Even turning her data on did nothing, so she can’t even watch hydraulic press videos while waiting for the Imps to arrive. She may have had a couple games installed, but that scratched screen was too big of a thorn in her side. She once again shoved the phone back inside of her shorts, which left a distinct rectangular bulge through the spandex to hide any potential cameltoe. She leaned back against the bench with her legs spread wide apart, and she sprawled out so she was taking up most of the space. Loona closed her eyes for a moment, and tried to relax with a couple of calming breaths. It actually worked for a few minutes, as she could feel a lot of her stress and frustration slipping away with each second.

However, her ears eventually perked up when she heard the faint sounds of… hooves?

Loona opened her eyes and blinked a couple times while staring up at the cloudless sky. The hoofsteps were starting to get louder, which prompted her to pull her head forward and see who was coming up. She wasn’t sure what to expect, but she had to do a double-take when she saw a yellow figure trotting down the middle of the road. Since there hasn’t been a car down this road for over an hour, the little pony was just walking down the yellow line like that was its intention. She sighed with a relieved smile when she saw the rest stop, and she quickly walked towards the ladies’ room.

“Oh, hello there!” She made sure to give Loona a friendly wave when she walked past, not noticing the baffled look on the canine’s face. Loona was not subtle when it came to her stunned, wide-eyed gawking on the clothless pony-thing. If it wasn’t for that ridiculously thick tail, which almost looked like a big hunk of cotton candy from how pink it was, there’s no doubt that Loona would’ve received a faceful of nonconsensual horse pussy. Meanwhile, the pegasus cheerfully skipped through the ladies’ room doors while humming a little tune. “Hmm, hm hm, hm hmm… La, la la, la laaa…”

When the doors closed, the mare’s tranquil voice could still be heard as she sang softly with the aid of the bathroom’s acoustics. Outside the building, Loona remained seated with a confounded look on her face. “... That… That can’t be right…”

Loona reached into her crotch to pull out her phone and check the time. Much to her shock, it was just past twelve-thirty; she distinctly remembered it being 12:21 when she popped those tabs, but there was no way they’d kick in this soon. Whatever that creature was, she was most likely real.

Her ears twitched when she overheard the singing inside, which made her grow a muddled sneer. “What the… is she actually singing while taking a piss?!” She couldn’t help staring back at the ladies’ room door with a scoff. “Hmph… Does she also beat-box while taking a shit?”

She huffed to herself with a barely audible chuckle, and settled back in her bench to re-check her connections. Despite how neon-colored that thing inside the bathroom may have been, she wasn’t radioactive enough to generate a usable wifi signal. She tried refreshing her pages a couple more times, but made sure to retract her claws and avoid more damage. She hoped to focus on her phone and ignore her scratch as much as possible, just in case that pony thing tried to talk to her when she exited the bathroom. However, before she could think to find her earbuds, Loona heard when the mare stopped singing.

“Ooh, hello there, Missus Spider! You have such a pretty web. I know you’re over the trashcan, but… would you mind if I threw this paper towel away inside of it? I really don’t want to litter.”

Loona dropped her phone, which thankfully didn’t break since it fell onto the bench seat. The hellound sat wide-eyed with her lips tightly pursed shut, but struggling to hold it in. After only a second, she clenched her eyes shut and hunched over her seat.

“Pbbbbttttt…. HAAAAAAHA HA HA HA HA HA HAAAAAAA!!!”

Loona couldn’t take it. Hearing such a corny statement (especially from such a cutesy voice) was more than enough to throw the canine into instant hysterics. She fell to the floor and rolled to her side, unable to care in the slightest that she was literally lying on a rest-stop floor. She continued to howl and laugh in complete mockery, reaching the point that she nearly ruined her makeup when she reached close to tears.

“HA HA HA HA HA HAAAAAAAA!!!” During the hellhound’s uncontrollable laughter, the pony emerged from the bathroom to see what was going on. She was surprised to see Loona cracking up so loudly, since she clearly had no idea what jostled her funny-bone. Unfortunately, she was given her answer when the canine pointed a claw at her and kept laughing. “Pbbbt, hehehehehehe… ‘Daww, could Aww use oor twashcan?!’ Oh my fucking GOD! HA HA HA HAAAAA!!!”

Loona’s face fell back to the floor, leaving her unable to see how quickly the pony’s smile dropped. The mare gave a faint scowl that showed slight annoyance, but not anger just yet. She may have been offended, but it wasn’t hard for her to take a deep breath through her nostrils in silence. Fortunately, that provided Loona just enough time to collect her breath and sit upright.

“Whoooo… h-holy shit…” She was still sitting on the ground as she wiped her cheeks, thankfully not smearing any of her gothic makeup. When she glanced back at that yellow pony thing, the two were now basically at face-level in Loona’s new position. Despite how cutesy she looked overall, the firm stare she pointed at Loona was definitely meant to be direct. But alas, all it did was make the canine snicker with her muzzle clenched.

“Gnnghh… What?” Loona quickly widened her red eyes to return the pony’s expression. “You need help talking ‘Mistah Spidah’ out his widdle web?~”

“I was just being polite.” The mare kept a calm and unoffended look on her face as she stood before Loona. However, even with how smooth and tranquil her coat may have looked, her muscles were tightly tensed in worry. Regardless, she breathed out silently while watching the canine’s brows perk up in surprise. The pony maintained her firm tone of voice as best as she could. “A-And… for the record, Missus Spider was actually very nice. And unlike you, I actually washed my hooves. She told me herself.”

That remark stirred quite the turn for Loona. Her smile instantly went away, and was replaced with an offended stare back at the yellow creature. It took her a moment to process the utter gall of that statement, which made her tilt her head bemusedly. “... the fuck did you just say, glitter-shit?!”

“It’s Fluttershy, actually.”

Loona’s head tilted in the other direction, but it did nothing to change how puzzled she was looking. Her muzzle hung agape for a moment, while her eyes blinked repeatedly. Fluttershy rolled her eyes with a bored-looking sigh, having already dealt with creatures ten times as intimidating back in Equestria over the past decade. Due to her surprisingly strong bout of bravery, she took that moment of stunned silence to point a hoof back towards the door. “And another thing! Missus Spider told me that you tried to squish her while you were in there! Why?! What did she do to you?!”

“Okay, that’s it.” Loona immediately got up and stuffed her phone in her pocket. She walked straight towards the bathroom with her paws clenched into fists. “One second…”

Loona kicked the door open, and stomped straight towards the dingy trashcan in the corner of the room. The unclean bathroom looked like something more appropriate for a horror movie, but the flickering fluorescent lights helped to hide a lot of the dingy tiles or handprint stains. Unfortunately, the large spiderweb above the bin was fully visible with an adorable spider smack-dab in the middle. Seeing the hellhound’s murderous glare, the spider went wide-eyed in fear; a long, continuous stream of her webbing began to come out of her which just draped down to the floor. Loona took that moment to take a big step, and throw up one of her legs to line up for a kick. “GNAAAAHHH--MPHH!!”

Loona was just about to stomp Missus Spider into the wall before she felt a pair of forelegs strongly holding her from behind. The sound of fluttering wings buzzed in her ears like a swarm of furious hummingbirds -- mostly silent, but still incessant enough to be impossible to ignore completely. Loona wasn’t able to move an inch forward, which meant the bottom of her hindpaw was less than a foot away from the wall and Missus Spider’s terrified face.

As for Fluttershy, she held the canine in a dead-lock from behind while hovering in the air.

Loona was rightfully stunned for a moment, her pupils shrunk to the size of pins. She blinked before glancing back at the mare, who was mere inches from her face with a very disapproving scowl. Fluttershy tightened her grip around the underside of Loona’s shoulders, which helped her hooves to better latch around her slender chest. Before the hellhound could try to protest, she was pulled back by the force of Fluttershy’s wings so her other paw skidded across the ground a couple feet.

“Don’t. You. Dare.”

Despite sounding like Jennifer Tilly on helium, Fluttershy’s tone of voice was nothing short of serious.

“What the?!” Loona was absolutely done by that point. She tried to quickly thrash out of the pegasus’ grasp, but Fluttershy responded by tightening her hold. Her hooves clasped both of Loona’s breasts, and pulled at her crop-top hard enough to tear open some of the larger pre-existent rips. She yelped out in shock, before gnashing her fangs and growling murderously. Loona tried to spin herself around several times, but the pony remained latched onto her back like a jockey. “GnnnNNNAAAHHH!!! GET THE FUCK OFF ME!!”

With a primal growl, Loona’s rage took over when she lunged back-first towards the row of sinks and the mirrored wall. Fluttershy was lucky enough to get the split-second needed to see the wall behind her, and she gasped in a panic. She may have not been the most skilled flier in Equestria, but Fluttershy knew enough about evasive maneuvers to instinctually crane her wings in opposing directions. With a couple frantic flaps, the pegasus miraculously spun herself around so Loona was thrown back to the front of the impact zone. “AAAAHHHH!!!”

*WHAM!!!*

Loona smacked the mirror face-first, leaving a nasty crack pattern in the broken glass that ironically resembled a spider’s web. Thankfully, despite how brutal that crash may have been, it was unlikely it did the slightest bit of long-term damage to Loona’s health. Nevertheless, such a strong crash certainly knocked her head around enough to leave her woozy. Fluttershy took advantage of that moment to remove her hooves from Loona’s breasts, and tightly grasp the sides of her head.

“GAH!!” Loona’s head was forcefully pointed slightly upward, and facing an unbroken shard of the mirror directly in front of her snout. She groaned and tried to thrash out of the pony’s hooves, but her eyes quickly made contact with those massive blue orbs in the mirror. Due to Fluttershy’s significantly larger eyes, it was surprisingly easy to catch the canine’s focus through that reflection. And much like many dangerous creatures and foes in the past, Fluttershy only needed to widen her eyes to their most intense degree…

“Mmmphhhh!! D-Dammit!” Loona tried to resist, but her body quickly froze the instant she saw Fluttershy’s pupils dilate so distinctly. She had no way of describing the feeling of paralyzing shock that struck her so badly, but she was unable to move a muscle while in Fluttershy’s control. That infamous Stare, which had claimed many canines years before Loona, quickly made her snarling muzzle lessen in tension. “Nnnnghhh… Mmmmmnnnnn…”

“That’s right,” stated Fluttershy in the firmest, but somehow also the warmest tone Loona ever heard in her life. “Just take a deep breath… and settle down, please…”

Loona’s head was completely blank, mostly due to how startled she felt from the pegasus keeping her in this head-lock for so long. But at the same time, her eyes never blinked as she stared up at Fluttershy’s Stare with her pupils widening slowly. She could feel her body moving on its own accord as she nodded her head slowly, and her claws retracted into her paws. She could also feel the distinct wags of her tail from behind, which smacked loudly against the sides of her hips.

‘Plap!’ ‘Plap!’ ‘Plap!’ ‘Plap!’ ‘Plap!’ ‘Plap!’

“Heh~” Fluttershy didn’t want to feel too cocky just yet, but hearing those tail-wags helped her to smile wider in confidence. She decided to lift one of her hooves away from Lonna’s cheek, and carefully reached back to start scratching behind her ear. “Therrrrrreeeee you goooooo… Is that better?~”

Normally, hearing such a cutesy infantilizing voice would’ve made Loona want to toss a grenade into a full maternity ward. But accompanied with the mare’s neck-scritches, which were… ungodly titillating to the canine’s nerves, it took everything in her not to start fidgeting her right leg in response. Her muzzle still opened up the slightest bit, but she was lucky not to have her tongue stick out as she exhaled deeply. Her eyes went half-lidded in instantaneous pleasure, but they refused to blink while staring up at Fluttershy’s unwavering Stare. “... AaaaAAAAaaahhhh~”

“Good girl…” Fluttershy’s smile widened even more, and her hoof slowly went down to scratch along the nape of Loona’s neck. Another long, shivering sigh came out of that fanged muzzle as she stood in place with her paws grasping the sink to hold her weight. Fluttershy took another moment to really get the hellhound settled, and smirked when she saw Loona’s head crane back the tiniest bit to invite that hoof further down her neckline. That was when the pony leaned in with a sensual lick of her lips, and whispered into her twitching ears, “You’re being such a Good Girl, Loona~”

Loona moaned and rolled her eyes back, shuddering from that praise when it was accompanied with the Stare so intimidatingly well. Fluttershy’s neck-scratches were so effective in quelling Loona’s anger, that she didn’t even notice that the pony knew her by name. Fluttershy took another minute to dig her hoof deep into that bushy neck-fur, noting how soft and unkempt it was while smelling of stale vape juices and discount whiskey. Normally in cases like Loona’s, the first thing Fluttershy would insist on doing is giving the mangy mutt a well-deserved bath. However…

… In this particular circumstance, the Element of Kindness knew that it was better to go a little dirtier first.

“Now then…” Fluttershy kept her tone firm and direct, but still comforting enough to keep Loona’s focus on her Stare. All she had to do was stop petting her neck for a second, which was more than enough to jolt Loona’s eyes back open. Her pupils quickly dilated upon returning to the pegasus’ control, once again leaving her body entranced and under new management. Fluttershy’s huge eyes did most of the work while she smirked more smugly. “Are you ready to act like a Good Girl some more?~”

Loona had no idea what came over her, but she couldn’t feel the slightest bit of an urgency when it came to dislodging this twisted pony off her back. In fact, she barely had a second to realize what was going on before feeling her head nod blankly again. Not even the smug huff from Fluttershy’s smirking muzzle could throw Loona out of her paralyzing trance. Although, the mare still needed a second to take a calming breath before pushing the envelope further.

“Well, in that case…” Fluttershy brought her other hoof down so it was no longer cupping Loona’s right breast. She gently grasped the underside of that dingy crop-top, and stated, “Loona… how about you take those clothes off for me?~”

Off in the corner, Missus Spider slowly backed away from the action with a newly unnerved look on her face. While the arachnid disappeared into the trash can, Loona slowly lifted up both of her arms without any resistance. With her eyes still pinned to the pony’s stare, she barely even flinched when she felt Fluttershy’s hooves grab her shirt and lift it off her torso. In less than two seconds, Loona’s chest was completely bare to expose her Size-B breasts for the broken mirror. Her black nipples stood out quite perkily, especially with her pentagram necklace and other jewelry helping to emphasize her slender figure. She breathed out shakily while standing on wobbling knees, her fur tingling for a moment from the cold air stimulating her nipples. However, even when Loona lowered her arms, she kept staring into her eyes as her thumbs locked around the waistband of her shorts.

“Those too.” Fluttershy’s voice rang through like a megaphone in Loona’s head, driving her to do as she was told. The canine obediently slid down her shorts, which still had her phone inside the crotch with the screen lit up. If she wasn’t so transfixed on Fluttershy’s beautiful blue eyes, she likely would’ve noticed the new message notification on her start screen. But alas, by the time her ankles kicked off her remaining clothing, and she was left standing naked in the dirty restroom, the screen eventually went to black without any notice. Meanwhile, Fluttershy nodded with an approving grin as she marveled at her creation through the reflection. “Good Girl~”

Loona’s muzzle opened even more, but her eyes strained a little as they struggled to stay open. Her whole body quivered in its newly exposed state, with her knees shaking badly enough to try and cross in closer together. Of course, the hellhound’s paws refused to pull inward and cover her crotch from the pony’s sight. Even as she stood mindlessly naked, she knew better than to hide her pussy from view. “Mnnnnghhhhh…”

“Oh my…” Fluttershy couldn’t help looking down from the mirror to see the hellhound’s waiting pussy. Since the fur around her nethers were as pale as an anime fan, Loona’s pink lips looked absolutely supple as they glistened in budding arousal. Fluttershy could see a couple thick droplets clinging to Loona’s fur around the sides, while her clit bulbed out ever so visibly with each heated throb. It may have been drastically different from her own marehood, but Fluttershy knew that the lady was getting riled up. Her smirk became a tiny bit more wicked as she perked up her brows.

“Hmmmm…” Since she had already gone this far, Fluttershy kept her Stare on Loona’s red eyes and commanded, “Play with yourself for me. Now~”

Loona once again nodded her head, this time with a slightly tingled moan. The canine kept her eyes right where they belonged, and stared right back at Fluttershy as her claw slid down towards her crotch. Without even questioning it, a couple of her digits tenderly dug between her wet folds to disappear into her slit. Her muzzle opened up wider, just before she let out a gasping moan from the sudden titillation. “Aaahhh!!~”

Loona had no idea what was coming over her, nor could she comprehend what the fuck Fluttershy was doing to her. But regardless, she had to cling onto the sink with her other paw while getting more intimate with herself. Her pawpads dug more diligently inside of her dripping cunny, causing her toes to curl up and her muzzle to snarl intensely. Fluttershy may have still been hugging her back like a novelty backpack, but she was clearly in control as she toyed with the hellhound like her own personal puppet. Of course, even with how foreign and scary Loona’s figure may have appeared, seeing a demonic entity masturbating under her obedience was unsurprisingly hot for the pegasus as well. She had to tighten her grip on the canine to hold herself in place, even as she felt her own arousal begin to trickle down Loona’s back.

“Nnnnfffff… T-That’s a Good Girl~” Fluttershy watched with more fervor the longer Loona played with her pussy in the middle of the room. The scent of Loona’s arousal was remarkably strong, with the estrogen-laden musk wafting throughout the restroom and flooding Fluttershy’s senses; although, compared to how the restroom smelled earlier, that change was quite the improvement for both of them. Loona hunched down even more while rubbing her folds, stimulating them relentlessly enough to begin drooling at the corners of her maw. She was still staring up at that pony’s reassuring face, with the dopiest grin beginning to appear just above her trickling saliva…

“Mmmphhh~” Seeing the canine’s elatedly lust-drunken smile was too much for Fluttershy to handle, and she blurted without thinking, “Aaahhh~ Sh… S-Show me your paw!”

Her expression froze up with a particularly heavy blush; however, since her eyes were still wide enough to maintain her stare, Loona groaned when she dislodged her digits without question. She moaned out like a little bitch when she held up her paw, allowing the sticky and glossy pads to be seen mere inches from the pony’s snout. Fluttershy tensed up with her muzzle clenched, but her nostrils instantly flared out when she caught a direct whiff of that sweet, syrupy secretion so close to her lips. She breathed out shakily through her nostrils, before her muzzle opened with a weak-sounding moan of her own. “Oh… O-Oh my…”

Fluttershy knew that she had to maintain her composure, especially against someone as large and scary as this demonic figure. But with the scent of Loona’s pussy coming off so ripe and mouth-wateringly thick, the mare couldn’t resist indulging so carnally. She grabbed hold of the canine’s wrist, and moaned out when she lunged in muzzle-first. Her lips wrapped tightly around one of those sticky digits, allowing her to get a proper taste of Loona’s drooling juices straight from the source. The flavor was unbelievably sweet, like concentrated citrus that nearly stung the back of Fluttershy’s throat. But at the same time, the jolt to her senses was far too stimulating for her to be satisfied from one taste alone. She eagerly sucked down that first digit with absolute vigor, while Loona leaned back from the sink and used her other paw to keep masturbating. “Mmmmphhhh!!~”

By that point, both ladies had their eyes closed in sensual pleasure in each other’s embrace. Loona was too lost in her own pleasure to pull herself from that lingering Stare, so she didn’t seem to care in the slightest about publicly schlicking herself in the nude like a common Floridian. She also didn’t pull her paw away from the hungry pony clinging to her shoulders, ravenously licking up every drop of her syrupy secretions like it was the sweetest nectar. She could even feel the pegasus literally humping her back, which grinded that equally wet horse-pussy hard against the small of her back and soak into her fur.

“Mmmphh!!~” Fluttershy’s lips slid off that last digit with a wet pop, leaving nothing but a freshly-cleaned paw-pad. The inside of her mouth was coated with a thick sheen of Loona’s dripping juices, but the pegasus couldn’t help swallowing up as much as she could. She let out a greedy moan as she exhaled weakly, undoubtedly hungry for more. But even with Loona so lost in her own pleasure, her rolled-back eyes quickly shot back into Fluttershy’s control when the mare needily tapped her shoulder. “Aaahhh!!~” The mare struggled to maintain her Stare as she moaned out direly, “P-Please! G… G-Get on your back for me!”

Loona complied as best as she could; unfortunately, that was by falling straight to the floor like a trust fall. Fluttershy gasped in a panic, but quickly flapped her wings to counteract the force pushing against her chest. She was thankfully able to stop herself from smacking on the dirty floor, and she kept herself hovering in the air when she carefully lowered Loona down in her place. Although, as soon as the canine made contact with the ground, Fluttershy frantically rushed around to her front so she could get herself between those long anthropomorphic legs. She grabbed both of Loona’ plump thighs, and yanked them wide apart so her pussy was completely exposed. Those glistening pink lips opened up so invitingly, with a couple thick strings of her arousal connecting her folds like the drooling maw of a hungry beast. But from Fluttershy’s perspective, whose nostrils strongly flared out upon catching the hellhound’s pent-up scent, that sopping-wet pussy was making her tongue feel particularly wet…

“Aaahhh!!~ S… Such a Good Girl!” Fluttershy dove right in between those thighs, and devoured the canine’s snatch with absolutely no mercy. Her little muzzle disappeared from sight, while her lips sloppily made contact with the ones between Loona’s legs. Her tongue plunged through her soft, warm folds as her tastebuds were set ablaze. The ripe, untamed flavor of Loona’s pussy was absolutely divine, and caused Fluttershy’s eyes to roll back in pure bliss. Of course, with Loona already lying on the floor with her eyes clenched tightly, she barely gave two shits when she grabbed the back of Fluttershy’s head with both paws.

“AAAAHHHHH!!!~” The hellhound’s back arched up from the dirty floor, which in turn shoved more of her hairy pussy straight up against Fluttershy’s mouth. The pegasus refused to hold back, and her lips remained widely parted so more of those syrupy juices could gush through to her waiting maw. Her tongue shoved itself even deeper, until she could feel Loona’s tight pussy literally trying to cling to it with each throb. The canine was absolutely reeling in her prone and exposed state, but her snarking muzzle kept an enticed grin while keeping Fluttershy pinned against her snatch. “Nnnnffffff… Awww, fuck yeah! Ge… Get in there~”

Fluttershy didn’t need to be told twice. Her eyes closed with total contentment, while the sweet tang of Loona’s pussy juices kept her tongue furiously flicking between all those folds. Her lips could be heard hungrily smacking between her rapid breaths, which came out in sharp huffs right against Loona’s clit. All that stimulation was keeping her mind helplessly clouded in lustful inhibition, and her body totally complacent in Fluttershy’s care. Eventually though, the mare’s eyes reopened the tiniest bit to glance upward, and see that petite little nub beckoning for some personal attention.

“Mmmmm…” Fluttershy’s eyes closed for a moment, she spent another minute or two savoring the taste and texture of such a unique anatomy. She made sure to spend a good amount of time tenderly suckling on the canine’s clit, leaving her an absolute wreck as she moaned and writhed against her face. She even made sure to flick the nub with her tongue for added measure, just to keep Loona’s toes curling. Her tongue swirled and explored every inch of the canine’s supple pussy, licking up every drop of the delectable arousal which dribbled off with every hair-raising shiver. Soon enough, thin rivulets of those pussy juices could be seen trickling down the sides of Fluttershy’s muzzle, and clinging to her neckline before soaking into her chest-fur. By the time she finally finished tasting her little pet, with one final drag of her tongue that went looooong and lingering against Loona’s sensitive lips, she was able to get a proper howl from the hound as she moaned out in tantalized rapture.

“GnnnnNNNAAAHHH!!! Mmmmphhhh!!~” Even though the cold air brushing against her wet pussy was enough to make her shiver, her lips were winking hard in anticipation for something more fulfilling than that tongue. She was still drooling obscenely between her legs, soaking a good amount of her fur; meanwhile, Fluttershy’s muzzle was already matted from cheek to cheek. But unlike the pony, who merely used the back of her forearm to wipe her muzzle and bring back a lustful grin, Loona was still lying on her back and panting like a hungry dog. “Haaaahhhhh… Nnnnnffffff…”

“Now, stay~” Fluttershy emphasized that command with a quick Stare down at the canine, who was quick to reciprocate when she took notice. As she laid naked on the restroom floor, her wet pussy now slightly gaped and convulsing for attention, it was hard to believe she was taken down so effortlessly by the meek pony. Although, to the hound’s credit, Fluttershy was definitely proving her capabilities far better than anticipated. And since Loona was still temporarily down for the count, she took her shot when she reached into the back of her mane. “Alright, where is it… Nnnghh, come on!”

It took Fluttershy a moment to fumble with the small hair-pin, which was discreetly placed along the very back of her mane-line for easy access. It served no purpose for her hair itself, but the glowing ornament attached made its significance clear. Along with transporting the pegasus to this unfamiliar world, Discord also made sure to include a small “present” to add to the experience. Despite never being informed of its presence directly, Fluttershy already seemed to be aware of its abilities when she unpinned it from the back of her head. She held it up for a moment with a curious smile, and hummed to herself before growing a wide and devious grin. “Hmmmmm… Oooooh, I know what to do with you~”

As soon as a flash of inspiration went across the mare’s eyes, the ornament on her hairpin flashed brightly enough to make it morph before her eyes. The pin floated up in the air for a second, before instantly transforming into a much larger item. Now a small travel bag with Discord’s initials on the front, it landed right in Fluttershy’s extended hoof like it was weightless. However, the mare’s face lit up excitedly when she saw what was inside. “Oooooohhhhhh~”

“Awww, fuck…” Since her pussy was still out and not being eaten, one of Loona’s paws went back down so she could keep masturbating. Fluttershy allowed her pet to continue playing with herself, since she needed a moment to get the costume and accessories out of her bag. During that time, the hellhound didn’t try to pull herself out of her tantalizingly lust-added state. With the image of Fluttershy’s insistent Stare drilling down to the deepest recesses of her conscience, all that Loona could do was obey her eyes and give in like a Good Girl. “Mmmmnnghhhh…”

Since her eyes were still closed, she could only hear the pony’s voice when she spoke up. “Mmmm… Who’s a Good Puppy, hmm?~”

“Mmmphhh… Aaahhh~” Loona kept digging deeper into her pussy, even though her digits weren’t able to reach all the places that tenacious tongue of Fluttershy’s could. Her muzzle opened right up without even thinking, and she moaned out like a slutty little pup. “AAAHHH!!~ I… I am…”

“Say it~”

“Nnnnghhhhhh…” Loona reeled with a strong shudder against the floor, which kept her from hearing the buzz of her phone inside of her panties a few feet away. Nevertheless, her eyes remained tightly clenched when she gave in and writhed between her eager schlicks. “Aaahhh!!~ I… I’m a… i-i-imagoodpuppy, mnnnghhh…”

That admission may have made her muzzle sneer in embarrassment, but it also made her heart race excitedly. Her hips began to thrust against her wriggling digits while she kept toying with her hungry pussy, which made her bare ass smack against the floor repeatedly. Fortunately, less than a minute of strenuous fingering was needed before Loona’s attention was diverted with a purposeful cough. Fluttershy cleared her throat, and stood with an especially confident smile before Loona’s prone form. “Oh, Loonaaaaaaa~”

“Mnnnghhh… Wh… Wha…” As soon as she reopened her eyes, they went as wide as dinner-plates in shock. However, her head also reeled back with an expression more akin to alarm than arousal. “W-WHAT THE FUCK?!”

Fluttershy may have not liked Nightmare Night, but she knew how to make a creative costume when needed. The mare was standing in a full-bodied outfit that covered her head-to-hooves in what looked to be shaved black wool. The hood over her head completely covered her mane, and was replaced with six oversized fake-eyes above her real ones. Along with the four identical sleeves of hairy fabric wrapped around her legs, there were four more connected to fake limbs hanging from the sides of her torso. From first glance, it was obvious that she was dressed up like a large spider; however, all that black fabric also allowed for Loona’s eyes to naturally draw downward towards the bright red accessory underneath. And from there, the hellhound’s eyes and muzzle widened with a heavy blush that spread across her cheeks…

“Hmph~ Not much of an ‘Itsy-Bitsy Spider,’ is it?~” Fluttershy shivered with an antsy giggle, but she tried to keep herself composed enough to remain in control. With even the slightest twitch of her hips, her whole body quivered from all the thick silicone pressing up against her. “Nnnnfff…”

Loona didn’t hear a word of what Fluttershy said, and just stared in awe at the massive horsecock planted between her legs. Looking as thick as a rolling pin, the veiny appendage nearly touched the floor because of its thirteen inch length. Fluttershy bit her lip with a groan each time she felt that thick, heavy rod of silicone bobbing underneath her torso; of course, that was more because of the other end of that toy, which was firmly lodged inside of her own marehood with the aid of Discord’s strapon. Sure, the spider costume was a weird addition alongside the bright red dildo, but Loona was too horny and inhibited to pay much heed. All she could do was look up at Fluttershy’s face with a couple heated pants, her blush still as pink as her pussy lips.

Fluttershy was ready for that to happen, and was already giving a fresh Stare to keep her little pet in check. With another harsh shudder, Loona was once again entranced under that infamous Stare to overlook the spider costume completely. Meanwhile, Fluttershy didn’t even blink when she spoke with utmost authority:

“Now… If you want to be a Good Puppy, you’re going to learn to like Spiders more. Understood?~”

If the draconequus was here to see her doing something this ridiculous, he likely would have proposed to her on the spot. But since it was only Loona, who was basically helpless beneath the spider-clad pony and her devious grin, the only response she could give was a brief moan as she tensed up. Her pussy winked hard enough for the pegasus to see from above, and she licked her lips with great anticipation. When she moved in closer to Loona, all that the canine did was part her legs apart invitingly. The mare accepted that gesture with a thankful nod, and came in between her legs until she was standing over that bare waistline.

Fluttershy’s domineering smile widened even more, and she reached behind her back for one last surprise: A thick, solid chrome chain that matched Loona’s collar perfectly.

“Turn over.”

Loona immediately did as she was told with a heated whimper. The naked hellhound rolled around on the dingy floor, until she was on all fours underneath the little pony’s frame. Fluttershy made sure to reposition themselves the slightest bit, so that Loona could be facing one of the unbroken mirrors across from them. Luckily for the pony, Loona didn’t try to fight back when one end of that thick chain was latched to the back of her collar. In fact, she let out quite the slutty moan when Fluttershy gave a teasing yank to pull her head up from the floor. “Aaaahhhh!!!~”

“Good Girl~” Fluttershy leaned down and kissed the top of Loona’s head as a reward. She then reached into a discreet side-pocket sewn into her costume, and pulled out a convenient bottle of lubricant. The mare quickly poured the entirety of that bottle onto her new toy, shivering when she had to rub the glossy gel across every inch of the rigid silicone. Even the smallest movements stirred the thick bulb plugging up her own marehood; but at the same time, that fake horsecock was planted inside firmly enough for the strapon to stay right in place. If the daunting girth of her end wasn’t so distracting, Fluttershy would’ve been impressed by how realistic the phallus appeared; from the flat and crowned cockhead, all the way back to its plump and heavy balls, Discord truly crafted a marvel piece of equipment to spear this surly mutt.

“Mmmmm…” After ensuring her tool of choice was safely prepped, Fluttershy wrapped her hooves around Loona’s waist so she could get her in a proper mounting pose. The hellhound moaned with an eager shudder, but remained on her paws and knees with her ass sticking up. She groaned when she felt Fluttershy’s weight press down on her lower back, but she gasped the instant she felt that distinct press of something hard and wet against her needy slit. The pony refused to relent, even when she made Loona let out a barking yelp with the first push of her hips. Her drooling lips pressed up tightly against that cold silicone, and tried to part open so all that hefty girth could give her a proper filling. It may have not been real, actual throbbing cockmeat trying to work its way past her folds, but it certainly reached all the buttons Loona needed pressing. Fluttershy’s tongue may have been stupendous in its own right, but nothing compared to a proper member guaranteed to stretch out all of her walls.

“Aaahhh!!~” Loona wasn’t able to grab onto anything while Fluttershy’s crowned head tested her resolve. Thankfully, her paw-pads provided just enough friction against the tiled floor to keep herself in place. She tried her best to brace her weight against that pressure, but that was easier said than done when she had to counteract against the strength of a literal horse. Fluttershy was relentless when it came to making use of her freshly-lubed toy. Even when Loona’s cries of pleasure became more strained, and then began to quiver under the pressure, that thick silicone kept prying open her snatch without mercy. By the time part of that thick outer ridge started to slip its way inside, Loona had to struggle not to pass out from how intensely her flesh was being stretched apart. “GnnnnnNNNNNAAAAHHHHHHH!!!”

Thankfully for both ladies, Fluttershy’s head managed to slip through that opening entirely during Loona’s primal shriek. Of course, with such a wide girth holding the hellhound’s snatch open like a soda can, Loona definitely needed a moment to adjust to such a thickness. Fluttershy was perfectly fine with waiting, since her own marehood was quivering tightly around her bulb and making her leak in her spider-suit. Her fake appendages could be heard scraping against the ground, which was unsettling enough to make Loona’s fur stand up across her back. Her head hung down for a moment, completely hiding her panting face from view beneath her thick silver hair. Of course, a hard yank from Fluttershy’s chain made sure she didn’t slouch down too low. And even beneath all that booze-soaked fur, Loona’s voice bellowed out the instant Fluttershy gave that first hard push of her shaft. “AaaaAAAAIIIEEEEEEEEE!!!~”

“There’s a Good Girl~” Fluttershy kept up her praise while staring Loona down through the mirror. When their eyes were transfixed on one another, the canine felt much more compelled to give in and take more of that cock. The mare took full advantage of that mindset as she kept plunging inch by inch, waiting until Loona breathed in to thrust hard into that dripping cunny. Each time she did, the hellhound could only belt out another hefty moan as she took every inch with absolute glee. “Mnnnghhh…” Fluttershy shuddered hard as she leaked more profusely around her bulb, which made it sink in deeper against her winking pussy. “Aaahhh~ I-I-I… I h-hope this makes you like spiders more, Little Pup~”

Loona couldn’t think clearly enough to dispute that point, and merely nodded while squealing like a little piglet. Her eyes were glued onto the spider-mare’s intense and unrelenting stare, which helped to make each thrust feel indescribably better. Her eyes nearly rolled back each time the dildo sunk deeper inside, until both girls felt the distinct resistance of Loona’s stomach. The thick bulge of Fluttershy’s cockhead pressed out beneath Loona’s bellybutton, before disappearing from sight when the mare pulled her hips back.

“AaaAAAaaaahhhh…” Loona moaned out while yearning for that cock to shove its way back in. But much to her perverted delight, the pegasus wasn’t done yet either. She delivered another harsh thrust into her, allowing that bulge to protrude from her gut once more. “AAAAHHHH!!!~”

“Mmmffff!!~” Fluttershy shivered after that thrust as well, since she felt that impact just as intensely as her pet. Both of them may have been stuffed with hard silicone between their legs, but the insides of both their thighs were thoroughly soaked with the remnants of their shared arousal. The spider-pony breathed in when she pulled back, causing Loona to whimper out for more; and when she thrusted back in to make the hellhound moan out, Fluttershy let out an equally hefty cry of pleasure herself. She repeated her actions once more, causing both of their voices to belt out in a lustful symphony in tandem with their smacking hips. Of course, that lovely combination of noises emerged a bit sooner the next time Fluttershy pounded into that demonic pussy. “Nnnnghhhhh… Y-Yeah, take it like a Good Girl!”

Loona could only cry out like a feral beast, while her body fully relished each and every thrust from the tenacious pony. Fluttershy may have kept her eyes wide and in focus, but even she was starting to feel lightheaded the longer her marehood clenched around her end of the toy. Their moans became louder. Their voices turned more rapid with each gyration of thrusts. The smacks of their bodies became lewder each time, as their matted fur were causing each impact to sound sloppier each time. Both of them were convulsing hard around their ends of the toy, and leaking all over the floor as their messy fuck-session grew more intense. Loona no longer needed to stare up at that spider-pony-thing to keep herself in place, as her eyes rolled back in sheer bliss from the overwhelming sensations that surged endorphins through her veins. As for Fluttershy, who was finding it harder to maintain dominance herself, she was perfectly fine with clenching her eyes shut while pounding Loona’s pussy for all it was worth.

The nude hellhound and spider-clad pony became totally lost to the pure, physically demanding crossover that left both of them moaning between heavy breaths. Loona was trying to push her ass back against Fluttershy’s toy, but it was clear from the thickness of that strapon that she was at the silicone’s mercy. Fluttershy wasn’t too far behind when it came to the race for who’ll climax first; however, despite how red the pony’s face was starting to get, she still had a determined scowl while devastating that demonic cunt.

“Aaaahhhh!!~ Who… W-Who’s my good little puppy!?~”

“MMMPHHHH!!~” Loona’s head reeled back when Fluttershy tugged on her leash to get her to talk. “I-I-I’m a good l-little puppy!! I… I-I’m YOUR good li… l-l-little puppyyyyYYYEEEE!!!~”

Fluttershy made sure to reward her pet with a harsher thrust into that hungry cunny. While Loona groaned in elation and pushed down hard against the floor, the bulge of that fake horsecock stood out even further through her stomach. Fluttershy strengthened her stance while mounting the canine, and doubled-down to really give that pussy a moment to remember. Her hips worked as hard as they could as she delivered an impressively quick barrage of thrusts, which rippled against Loona’s ass and smacked loudly enough to overpower her piercing moans. And with the pegasus thrusting into her like a jackhammer with so much thick cock, Loona was quickly set over the edge while her head was being rocked back and forth. “Aaahhh!! AAAHHH!! AAAAIIIEEEEEEEEE!!!~”

Her pussy clenched hard around Fluttershy’s toy, finally able to lock her in place despite all that lube. As soon as the mare’s hips stopped moving, Loona writhed hard on the ground and roared violently loud. Fluttershy tensed up and felt her own orgasm looming in, but she had to cover her ears with both hooves when Loona cried out louder than a literal Siren. All the mirrors in the bathroom shattered impressively from the hellhound’s voice, and even cracked some of tile flooring underneath her. Her orgasm ended up lasting much longer than the pony’s, as Fluttershy was able hump herself to completion with a few harsh grinds against her bulb. While the mare hugged her tightly from behind, finally succumbing to her own climax with a long and winding moan, Loona had to press her head down against the floor after yanking her chain out of Fluttershy’s grip.

“HAAAHHH!!! Haaaahhhh… Hrrrrmmmmm~” By the time Loona was able to stop panting like a bitch in heat, she let out a deeply relieved sigh as the post-coital feeling of satisfaction sank in. Fluttershy’s horsecock was buried up to the medial ridge inside of her; although, even with the thick belly-bulge she was sporting, there were still a few inches of exposed silicone between the girls’ exhausted bodies. Fluttershy had to cling to her backside while breathing heavily, her legs twitching hard while soaked in the aftermath of her own arousal. Not to mention, her spider-suit turned out to be a bitch to wear after such a grueling workout session.

“Haahhh!!~” Fluttershy used the last of her strength to yank herself off the hellhound’s back. Loona’s eyes shot wide-open as she made a startled and sputtering cry; although, that was definitely warranted when Fluttershy fell backward, and the gravity forced all thirteen inches of that hosecock to slide out without preparation. The canine’s poor cunny was nearly prolapsed from how brutally that toy was yanked out, which temporarily left her just as mindless as when they started. Loona fell face-first onto the dirty bathroom floor, her face plastered with a dopey grin while her pussy was fully gaped and convulsing hard.

“... ohmigosh… o-ohmigosh…” Fluttershy was slightly more conscious than Loona, despite feeling like she was baking inside her woolen suit. However, before she could think to get out of her spider costume and strapon, she gasped when she heard the bathroom door opening up. As soon as a bright red figure appeared inside the room, Fluttershy froze up while holding the hairpin in her hoof; luckily, one hard squeeze to the ornament caused it to light up brightly for a quick escape.

“Loona, you here?” A pissed, timid-looking Imp with a bow-tie, curved black horns and a bright red complexion poked his head through the doorway. “Do you have ANY idea how much it’s gonna cost to--”

Moxxie froze in horror. His law went agape and nearly touched the floor. Before him was the sight of Loona sprawled out completely naked, covered in lube and pussy juices after being given the most brutal fucking that week. Beside her was the terrified expression of Fluttershy’s, although it was hard to focus on her face while she was dressed up like a nine-legged spider. As soon as Moxxie got a good look at the mare’s costume and strapon, a bright flash of light caused her to completely disappear from view. All that was left was the moaning, drooling hunk of hellhound that could barely move an inch from her exposed position. “Aaaaaaaahhhhhhhhhhh…”

“... Uhhhhh…” Moxie could only stand in stunned silence for a moment. His blush was near-impossible to see through his demonic complexion, but the small bulge in the crotch of his slacks indicated he saw more than enough. Regardless, he now looked quite concerned as he turned his eyes away from the incapacitated canine. “... Loona?”

She may have been fucked to near-exhaustion, but she still had enough strength to lift up a paw and flip off Moxxie’s voice.

“OH, FUCK YOU TOO!!!”

Author's Note

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