Deal with a Hellhound

by Alphamon_Ouryuken

Rating: mature
Tags: Crossover, Sex, Anthro, My Little Pony: Friendship is Magic, Dark, Alternate Universe, Other, Porn, Fetish
Length: 5475

When faced with the fires of Inferno, becoming a lapdog doesn't sound all that bad...

Gingersnap's death should have landed her in the fiery pits of the underworld... but a certain Hellhound had a different use for her: she would be spared from the fires of the underworld and for an indeterminate amount of time, and in exchange she would give the Hellhound some useful information regarding possible targets.

However one faithful day, the Hellhound ended up adding in an extra term to their deal, and she has no choice but to accept...

Notes:

Triggers: Rough Sex, Femdom, Yuri, Futanari.

Gingersnap is a character from the IDW comics, not an OC.

Crossover with Helluva Boss.

All characters depicted are 18 or older.

My Entry for the Furry Foray Festival!

Cover art by CanaryPrimary.

Published 2023-03-27 15:20:01 UTC
Last updated 2023-03-27 15:20:01 UTC

Time to Pay Up~

Inside the Principal's office of Celestia's School for Gifted Unicorns, the lights were dim and the room was filled with the sound of soft moans. A full-grown anthropomorphic Unicorn mare with a long, curly deep-brown mane and tail, a deep orange coat, and turquoise eyes eagerly locked lips with her student; a mint-green Unicorn mare named Lyra Heartstrings.

"We-mmph, we g-gotta make this q-quick, Principal Gingersnap." Lyra gasped as their tongues danced together, and after a few minutes, she just barely managed to pull away from her Principal, her legs shaking as she gazed into the mare's alluring eyes. "My… m-my father's gonna be waiting for me outside…"

A perverse giggle escaped Gingersnap's lips as she wrapped her arms around Lyra's neck and gently ran her fingers through the mare's hair. Smirking, the Principal gently planted a kiss on Lyra's lips before taking a few steps back and sitting atop her desk, casually spreading her legs as she lifted her skirt to reveal her glistening wet pussy. "Well then, you better start licking, my little mynx~" She purred, beckoning her student closer with a 'come hither' gesture.

Biting her lip, Lyra knelt before the Principal and quickly closed the gap, pressing her mouth up against Gingersnap's marehood, enveloping her face between the Principal's legs.

"Make sure-mmmph, you do a thorough job-ooohh!!" Gingersnap cooed, placing her hand on the back of Lyra's head and pressing her face deeper into her crotch. Lyra wasted no time putting her mouth to work and ran her tongue up and down the length of Gingersnap's marehood. "Aaahhh… and r-r-remember what I… p-promised you~" She added, earning a muffled "Yes ma'am…" from between her legs. Gingersnap then started bucking her hips as Lyra continued to desperately lick her pussy with great vigor, earning a series of moans from the Principal.

As Lyra started to suck on her clitoris, Gingersnap was forced to bite her lip to keep her moans from getting louder, wrapping her legs around her student's head as the girl's tongue plunged deep into her slit. Gingersnap had to admit, out of all the students she'd seduced, Lyra was one of the best at oral stimulation, putting an immense amount of effort into pleasuring her without pausing to take a breath. That, plus her naturally submissive nature made her one of her favorite students to seduce. All it took was for Gingersnap to act comforting, gentle, and caring… and the girl was putty in her hands.

The Principal snapped out of her thoughts as a surge of pleasure quickly shot through her, the feeling of Lyra's mouth expertly pleasuring her, bringing her very close to an orgasm. She could feel her marehood pulsating around her student's tongue. "That's it! G-Good girl!" she cried out, bucking her hips against Lyra's face, getting closer and closer to the edge. "That's it, right there! Oh, yes! Oh yes! Yes! Yes! YES!!" Gingersnap gasped before quickly covering her mouth, praying she hadn't been too loud as pleasure overwhelmed her senses. The climax hit her with the force of a locomotive and shook her entire body, it took every ounce of restraint for her not to scream in ecstasy right then and there as her fluids splashed into Lyra's mouth.

Lyra, in turn, let out a muffled yet orgasmic moan as she relished in the sweet taste of her Principal's pleasure fluids, desperately sucking and drinking them down. She didn't stop until Gingersnap collapsed backward onto her desk. Snapping out of her daze, Lyra quickly pulled herself free from the prison between Gingersnap's thighs, gasping for air as she licked the fluids off her lips.

"W-Was… was I good… Principal Gingersnap?" The girl meekly asked, watching as the grown mare panted deeply while lying atop her own desk, sweating and shuddering with a blissful smile on her face.

"Y-You were... extraordinary…" Gingersnap sighed as she slowly sat up, taking a moment to catch her breath. "And of course... good students get the best rewards…" She added, reaching into her desk and pulling out a few sheets of paper.

Lyra's face lit up as she realized exactly what the Principal was holding. "My test scores!"

"Had to leave a few of the answers incorrect, just so it didn't look too suspicious." The Principal explained as she got off her desk and started cleaning up. "But trust me, these scores will be more than enough for you to pass."

"Oh, thank you, thank you, thank you!" Lyra smiled, gazing up at her with a mixture of joy and gratitude as the Principal finished getting her things together, wiping the girl's face clean with a white handkerchief and straightening out her sweater.

"Now, I suggest you get going. I'm sure your father is waiting." Gingersnap concluded before giving the mare a quick kiss on the forehead. The mare nodded as she got up and rushed towards the door. "And remember Lyra…" Gingersnap began, abandoning her soft, seductive tone and shifting to her 'stern teacher' voice, forcing her student to immediately stop in her tracks. "...you are not to breathe a word of this to anypony, understand?"

"Y-Yes… I-I understand..." Lyra stammered, her shy demeanor quickly returning as she hurried out of the room.

The moment she was sure the Unicorn was out of earshot, Gingersnap let out an exasperated sigh before she started cleaning up her desk, carefully straightening out her purple blazer and amber skirt and making sure everything in her office looked presentable once more. She then took out an air freshener and quickly plugged it in, hoping to air out any musky smells that may linger.

Of all the schools she'd been employed at, Celestia's School for Gifted Unicorns had to be one of her favorites. She always had access to an ever-expanding list of stallions and mares to pick from, each one having some type of vulnerability that she could exploit by using just the right words. All she had to do was offer a shoulder to lean on, give them just the right amount of attention to lure them in, play to their more naive sides and manipulate their affections to her benefit, or in certain cases, dangle a metaphorical carrot in front of them in the form of better grades, a chance to succeed and/or excel in certain subjects and events, or just looking the other way regarding their actions.

Oh, how she loved her little game of deception and seduction.

Of course, there was always the risk of her illegal escapades being exposed. Even though she made sure all of her "conquests" were past the age of consent, she'd still get into a lot of trouble and most likely lose her job.

Then again, the risk just made things even more exciting for her.

"Now let's see… who's next…?" The Principal mused to herself, and she took out a small folder, thumbing through the names of various students. "Hmm, Moondancer sure is cute, but she seems more fixated on that Twilight girl. Can't have potential secondary relationships getting in the way…" She casually put the folder back and went through a few more. "That Aurora Veil sure is handsome, but then again, his little friend is such a cutie-"

"Enjoying yourself?"

Feeling a chill run down her back the Principal quickly shut the folder and turned around to see another Unicorn standing in the doorway… although she didn't recognize this one.

She had crimson eyes, a deep grey coat, and a long silver mane styled towards the left side of her head while a portion of the right side was shaved. Her tail was of equal coloring with a few white highlights near the edge. She wore dark-gray eyeshadow, black lipstick, a piercing on her right eyebrow, and two earrings on her right ear.

Her attire consisted of a spiked black choker around her neck, a tattered gray crop top held up by several spaghetti straps attached to said choker that stopped just above her stomach, leaving her belly exposed, black shorts, fingerless gloves, knee-high socks, and high-top sneakers.

"It's been quite a while, Gingersnap…" She smirked and entered the office with a casual smile and a mischievous glimmer in her eyes.

"I'm sorry, but… who are you?" The Unicorn asked, carefully putting the folder away.

"Oh, we've met… a while back." The girl replied nonchalantly, inspecting her nails as she approached the Unicorn. "Although I guess you wouldn't recognize me, given how many students you've seduced-"

Narrowing her eyes, Gingersnap immediately took a more authoritative stance. While she'd indeed had her fair amount of secret trysts with numerous students, she'd always ensured to keep track of exactly who she had gone after, just in case someone tried to get one over her with vague accusations. "Listen here, young mare, I don't know what sort of outlandish rumors you've been told, but I will not tolerate being accused of such acts by-"

"Oh, drop the act already, after all…" The girl's eyes were surrounded by a haunting crimson glow. Gingersnap felt another chill run down her back as the door slammed shut, and what appeared to be some sort of symbol appeared right underneath the mare. "...it wouldn't be the first time I've caught you indulging yourself." She smirked before tossing her bookbag to the side.

Terror gripped Gingersnap's heart as the mare's body was suddenly engulfed in a swirling vortex of blue flames that erupted from the symbol, stripping away her Equine exterior to reveal something much more… feral.

In the mare's place was a much taller anthropomorphic wolf with white fur. The lower half of her face morphed into a pointed, dog-like muzzle with sharp teeth and a dark gray nose. Gray patches of fur grew around her face and on her shoulders while the colors of her eyes became inverted, with her white sclera shifting to blood red and her crimson irises shifting to white. Dark gray ears sprang up beneath her hair, and a long, bushy, gray, and white tail erupted from the base of her spine.

This girl… was a Hellhound.

One Gingersnap knew very well.

"L-L-Loona!?" The Unicorn gasped, backing away nervously as the beast approached her. "W-What are you doing here!? Why are you even here?! I-I should have at least five more years-"

"I thought I'd visit a little early this time." The Hellhound cut her off, licking her lips as she gazed into the Principal's fear-stricken eyes. "Y'see, my da-" She flinched, pausing for a brief moment before continuing. "My boss is looking to appease some vengeful souls holding a grudge against the living, but sadly business has been a little… slow."

The Unicorn blinked, and suddenly the Hellhound was gone. Upon taking another step back, she froze up at feeling warm fur against her back, the pupils of her eyes slowly moving to meet Loona's as the Hellhound leaned over her left shoulder. "...so I'm here to collect on our little 'arrangement'… and I'm sure I don't need to remind you exactly why I was generous enough to spare you from a trip to the fiery pit." She whispered into the Principal's ear, the very feeling of the Hellhound's breath on her skin sending chills down the mare's spine. "Trust me, I know a lot of Imps, Succubi, and Demons in the Lust Ring who'd love to get their hands on you."

Part of Gingersnap never wanted to recall that terrible day…

It all happened so fast, what she'd assumed was just a minor distraction while driving… and the next thing she knew…

Flames…

…the most unimaginable pain…

…and then, she appeared before her.

The Hellhound… nonchalantly staring down at her with the same amount of interest one would give an ant.

"Hey, you wanna live?" She asked casually, as if she were discussing the weather.

With her voice unavailable to her (she was pretty sure her throat had been torn open), a weak nod was her only reply.

"Cool, you work for me now." She replied with a coy grin.

And just like that, Gingersnap had been saved from her trip right into the inferno, all in exchange for giving Loona specific targets that souls of the damned would be more than eager to drag into the flaming pit for vengeance. Be it a simple jackass who slighted them, a business partner who gave them the short end of the stick, a cheating spouse, a gang who had you killed for knowing too much, etc.

And the more clients she landed the Hellhound, the more decades Loona would add to her time in the land of the living…

…but of course, on certain occasions, she'd ask for a few extra favors.

"…and who knows? If your intel gives my boss more clients, I might be persuaded to give you twice the amount of years in the land of the living." The Hellhound added, snapping Gingersnap out of her thoughts and barely giving her time to react as Loona turned the Principal around. "All that, plus I could use some stress relief. Now… open wide~" Loona cooed as she pulled her in close and kissed roughly on the lips.

While taken by surprise, she remembered their deal and gave in to her urges, leaning forward and kissing Loona back. Making out with someone with such a long muzzle was pretty awkward, but Gingersnap worked with what she had, wrapping her hands around Loona's waist while the Hellhound's moved up to her shoulders. "Now relax. Just pretend I'm one of your students." She added in a taunting tone, bearing her fangs as she roughly bit the Principal's lower lip, not hard enough to draw blood, but with just enough force to remind her who was in control. As she made out with the Hellhound, Gingersnap started unbuttoning her blazer, letting it slide off by rolling her shoulders a bit. Loona then grasped the bottom of the women's sweatshirt and pulled it over her head. After tossing it to the side, Loona broke the kiss and pushed the Principal back. "Now kneel." The Principal flinched at her tone but did as she was told. The Hellhound before her sat down on Gingersnap's desk as her crimson eyes examined the Principal's body. "Very nice… I can see why so many students dropped their pants for you." Loona chuckled… before proceeding to rest her right paw against the Unicorn's face. "Now then, why don't you share some of that info while you're cleaning my feet, pet?"

"Yes, Mistress…" Gingersnap replied, doing her best to maintain eye contact with the Hellhound despite her paw being pressed firmly against her face. Swallowing her pride, the Principal opened her mouth and dragged her tongue up Loona's black paw pads. "There have been… s-some rumors… surrounding R-Rich Corp… as of lately… a few… employees h-have g-gone missing… or w-were t-transferred to a branch… outside the city…" She explained between licks as she dragged her tongue up and down the Hellhound's foot, lathering it with her saliva.

Loona casually inserted three of her fingers deep into her moist slit, letting out a soft moan as the Principal worshiped her feet. "Oh? And what exactly would they be so eager to hide?" She inquired, her white eyes meeting Gingersnap's lavender ones as she removed her right paw and replaced it with the left.

"...m-money laundering… development of p-products using… illegal muh-materials…" Gingersnap explained as she kept licking the Hellhound's sweaty paws, doing her best to ignore the overwhelming taste and scent. "...employee abuse in some areas… and… and I think… I think the boss might be ch-cheating on his wife…"

"Interesting… gonna have to look into that later…" The Hellhound mused as she continued to play with her loose folds for a few more minutes, after which she lifted her feet from the Unicorn's face and snapped her fingers. "On your back, slut. We're skipping the foreplay." She stated in a firm tone as she pulled her shorts off, revealing that she wore no undergarments this time.

Shivering, Gingersnap complied and laid back, only slightly raising herself up on one elbow. The Hellhound quickly knelt down and grabbed her left foot, lifting the Principal's leg straight up and exposing her glistening marehood. "Oh shit, we aren't even fucking yet and you're soaking wet already!" Loona laughed as she sat down and spread her legs, taking a moment to angle herself just right as she inched her hips toward the Unicorn's until the lips of her pussy were pressed against her own. "Or is that just saliva from the last student you molested?"

Gingersnap flinched at this (accurate) accusation but said nothing, biting her lower lip as the Hellhound slowly gyrated her hips, as if looking for just the right spot… and the signal that she found it came in the form of a sudden pulse of pleasure shooting through the Principal's body. "Hhrrkk, gaaah!" Before the Principal knew it, the Hellhound had started to grind their crotches together. Gingersnap did her best to hold back a moan as Loona's rubbing became more of a bucking motion. Her own body instinctively started moving to the same rhythm, and her breathing got heavier.

"Aww, did that strike a nerve?" Loona taunted as she quickened her pace and ground herself harder upon Gingersnap's sensitive pussy, sending jolts of pleasure through her body. Said pleasure was also laced with a dual sense of pain because Gingersnap's pussy was still extremely sensitive, having recently experienced an orgasm during her "session" with Lyra moments ago.

"OH FUCK!" The Unicorn shouted as her stomach started to convulse, her whole body twisting and trembling. She tried to fight through the dull pain produced as the Hellhound rubbed her sex against Gingersnap's, but her moans only got louder, and her fear of being caught quickly lost its thrill factor. "F-FUCK! OH SWEET CELESTIA, W-W-WAIT, PLEA-MMPH!?"

…only for Loona's mouth to latch onto hers once more and force her into another sloppy kiss, their tongues becoming intertwined as their crotches continued to grind against each other. The Unicorn moaned into the kiss every few seconds, desperately keeping herself from screaming again as the pleasure was quickly eclipsed by a sharper pain from her sensitive pussy. She mentally prayed that the Hellhound was close to finishing, unsure of how much more she'd be able to take.

"Mmm? Surprised you're not getting into it more…" Loona cooed as she stroked her marehood against Gingersnap, noticing that the Principal's hip movements were becoming more sporadic and random, not matching her own rhythm and seemingly focused on desperately trying to make as much contact with the Hellhound as possible. "Did I catch you at a bad time? Was the green-haired chick that good?" She chuckled, knowing that Gingersnap was very close. Loona then leaned in, carefully positioning her lips right next to the Principal's left ear. "Well, you better hold out until I'm satisfied. Because if you get off before me, I'll have you begging me to drag you down to Hell." She growled menacingly as she continued to rub her slit against Gingersnap's as fast as she could.

A heavy sense of dread welled within Gingersnap's gut as her whole body started shaking. Her long legs instinctively tightened around the Hellhound's waist as her toes curled and her breaths became deeper and more ragged. "L-Loona… Loonaaahhh… pluh-plea-OOOOHHH!!"

Unfortunately, a few more thrusts from the Hellhound were all it took for the Unicorn's body to give out. Her moans turned into screams of agonized ecstasy, and her whole body stiffened as the unified rush of pain and pleasure took over the Principal's body, forcing her to experience the most mind-shattering orgasm of her life. "AAAAHHHH!!!!" She screamed as her fluids sprayed out onto the rug and Loona's marehood, her body writhing uncontrollably as she arched her back for a few seconds before finally tiring out and collapsing onto the rug.

"Oh, you little bitch!" The Hellhound snarled as she pulled away from the mare and grabbed her by her hair, forcing the Unicorn up to eye level with her fangs bared. "I warned you what would happen if you got off before me! You're my stress relief, not the other way around!" Loona growled in barely restrained fury before unceremoniously dropping her to the ground. The Hellhound quickly reached into her bookbag and pulled out a bottle of liquid and some sort of blue book with gold markings and symbols on the cover and a large red gem in the center of its spine; a Grimoire.

"Uuughh…" The Unicorn groaned as she came down from her orgasmic high and regained her composure. Turning her attention to the Hellhound, she heard her speaking in some sort of foreign language as she opened up the book and turned to a specific page her eyes started to glow. "Wh-what are you-"

A sudden flash of black flames erupted from the Grimoire, covering Loona's crotch and catching Gingersnap by surprise. As the Hellhound turned around, she glanced down at the Principal and gave her a coy grin before gesturing to her marehood… which now had a very noticeable sheath right above it. She barely had time to respond as Loona gently caressed it, coaxing her shaft out of its sheath with a few strokes, her sense of dread returning as she witnessed the slick, throbbing, crimson shaft emerge. 'SWEET CELESTIA!' The Principal thought, her jaw dropping as she took in the sight of the Hellhound's shaft. It was thicker than her arm! And much longer than any stallion she'd ever been with, practically making the biggest toy she'd seen look like a twig by comparison!

…and she was planning to shove that beast… that behemoth… inside of her?!

She couldn't help but feel a sense of terror grip her heart… and yet she also felt a small bit of excitement as she rubbed her legs together. She had taken plenty of cocks in her long life, and the thought of this thing penetrating her so fiercely…

"Turn over and raise your ass." The Hellhound demanded as she stormed towards her while unscrewing the cap on the bottle, snapping Gingersnap out of her thoughts.

"Oh… sweet Celestia…" The Unicorn breathed as her cheeks heated up, never taking her eyes off of the swinging, throbbing pendulum between Loona's legs. "It's s-so fucking big! Will that thing even fit?!"

"Oh, don't worry… I'll make it fit," Loona said with a wolfish grin, casually pouring the contents of the bottle onto her cock, revealing it to be some sort of pink lube. "Although if you relax and let it happen, it might not hurt as much… no promises, though."

Gingersnap gulped as she slowly turned around and obediently raised her hips… only to feel a sudden pressure on her back holding her down, followed by a vicious growl. "Hold. Still." Loona snarled, her eyes glowing as she pinned the Unicorn down.

The Unicorn could only wince at her tone and freeze in place, not daring to move as she felt Loona's hands firmly grasp her rear and force her cheeks apart. Gingersnap could only shudder with excitement as she felt the tip pressing against her anus, her back arching slightly as the pressure steadily increased. Gingersnap's breath then caught in her throat as her anus instinctively clenched in a vain attempt to stop the Hellhound from penetrating her… but to no avail.

"Just be grateful I'm not going in dry, and that's only because I don't want to ruin my toy." Gingersnap heard Loona whisper into her ear. The mare could feel the tip of her massive cock edging its way inside her asshole, slowly stretching it open. The Principal could only brace herself for the inevitable as the Hellhound angled herself in just the right position.

And with that, Loona slammed her hips down against Gingersnap's rear and forced her shaft deep inside her anus.

"FU-"

In an instant, everything around Gingersnap melted away…

…there was no office…

…no school…

…no Loona…

…and no sound…

…it was like the world had gone completely blank, filled with nothing, but white noise…

…and the only thing that mattered… was this powerful, unique amalgamation of pain and pleasure.

She wasn't sure how long she had remained in that void between the waking world and blissful unconsciousness, it almost felt like an eternity before she finally came back down-

"-UUUUUUUUUUUUUCK!!!"

Gingersnap didn't even realize she had started screaming until she felt the Hellhound roughly forcing her face down against the rug.

And then it all came back to her, the first thing her mind registered being the immense mixture of pleasure and pain shooting through her body from her rear. She could feel her anal walls clenching tightly around the massive intruder, desperately trying to cope with its size as they were stretched wider and wider, the Hellhound's massive shaft filling her up, forcing her anus into an 'O' shape, her inner lips skin tight against her vein riddled thickness stretched like nothing else in her life. Her throat almost went dry as she inhaled deeply, her whole body stiffened up, her fingers dug into the rug and clenched two fistfuls of fabric, her toes curled, her eyelids fluttered as her very eyes rolled back, and her back arched, all while the Hellhound viciously stretched her out.

Loona paid it all little to no mind as she forced her hips forward, pushing her shaft deeper and deeper, inch by agonizing inch disappearing inside the Unicorn and forcing her insides to part just for the sake of taking the Hellhound's cock. "J-Just be grateful... that I used… a-any lube during this…" She grunted, the mare's breaths becoming short gasps being the only response she got, not that she truly cared. The Hellhound paused before forcefully pulling her hips back, shuddering at the sensation of the Unicorn's insides dragging along her cock, her anal walls clinging to it as tightly as possible… and the moment she was halfway out, she slammed back in without any warning.

"G-GRAAAGH!! HNNNGGG!!" Gingersnap grunted, finally finding her voice as Loona plunged back into her depths, the feeling of every bump and vein on her shaft driving her wild. "SO G-GOOOOD, IT HURTS S-SOOO GOOOOOD!!" She screamed as she threw her head back, drool leaking from her mouth as she felt Loona thrust back into her, her anus contracting around her member as if it were trying to pull it back inside of her. "H-H-HOOOLY SHIT!! IT'S DEEP! IT'S SO FUCKING D-DEEEP!! AHH! AH-HAAAHH!"

As the Unicorn started hyperventilating, her eyes unconsciously slid over to a nearby mirror, her gaze focusing on Loona's hips… or, more specifically, the slowly inflating knot at the base of her sheath. Gingersnap's eyes widened in anticipation as said knot continued swelling in size, the Hellhound's sheath stretching wider until it slipped free. "Is… is that-AAAHH!" She yelped, the Hellhound gritting her teeth as she kept thrusting her hips, pistoning in and out of Gingersnap's writhing body, stretching her anus out more and more with each ruthless slam of her hips.

"Be glad I put some soundproof glyphs up before I showed up, pet," Loona whispered as she bit her lip, grunting just as her enormous knot collided with the wailing and thrashing mare's aching anus.

"HAHN! HAH! AHH-HAAAHH!" The Principal cried out in ecstasy as Loona's thrusts became even more aggressive, twisting and shifting her hips in an attempt to force the knot in bit by bit, sending Gingersnap into a spiraling screaming fit as her anus was forcibly expanded, slowly but surely spreading until it finally engulfed the knot, locking them together. "AHEEEEEEE!!!"

Gingersnap's mind returned to that void of white noise once more, this time slightly more aware of what was happening.

The Hellhound was actually inside her…

…she… she could feel the roughness of her knot scraping at her tightly stretched walls…

…she was being filled…

…and it felt really… really fucking good.

She… she wanted more…

She needed more…

More, more, mo-

"-OOOOORE!!"

Once again, Gingersnap realized she had started screaming before she came down from semi-consciousness. The face of the horny Principal was now a twisted mixture of pain and pleasure as she felt the Hellhound pounding her ass surprisingly easily despite the knot. Gingersnap had gone from screaming to moaning the very moment she registered an odd, slightly uncomfortable sensation of Loona's cock rubbing against her anal walls. The unrelenting jolts of pain and pleasure seemingly flipped a switch in her brain, causing the Principal to essentially fall in love with the feeling of being penetrated like this, her mind now shattered and hungry for more. "D-Duh… d-deeper… huah… h-harder…" She pleaded, unconsciously thrusting her hips backward onto Loona's cock, taking the last few inches into her all at once. 'S-So deep, so… so gloriously full~' Were Gingersnap's only thoughts as she slowly moved her hips back and forth slightly, adjusting to the feel of the Hellhound's hard cock now buried inside her.

Gritting her teeth, Loona withdrew just a little before pushing in again, basically humping her ass with each grunt getting heavier as she felt the mare tense up, a clear sign that she was reaching the peak of pleasure. "That's it bitch, cum. Cum from getting your tight ass raped, you slut!" She snarled as she wrapped her arms around Gingersnap's neck, pushing as deep into her ass as she could possibly go, making her wince in pain and pleasure.

And with one final thrust, the Hellhound came inside her, her hips bucking wildly as she pumped spurt after spurt of her thick seed into the Unicorn, all about letting out a long orgasmic shudder as she felt Gingersnap's anal walls tightening around her shaft as if it was trying to milk every last drop. "Hrrkkk! Grrrrkkkk!"

"Ah! I-I… I'm… I-GGGHHH!?" Gingersnap choked, her face twisted in bliss and her eyes rolling back as she felt her ass getting filled up with the seed of her Mistress. She could feel her legs going stiff and rigid as her own orgasm shot through her body, sticky clear fluid spraying from her womanhood in every direction as her mind melted into pure ecstasy.

After climaxing together in orgasmic unison, the two slowly calmed down while panting heavily. The Hellhound collapsed onto the Unicorn in exhaustion, and they stayed in this position for a few more minutes, basking in their euphoric high.

For just a few short moments, nothing existed outside of pure ecstasy.

"Uuuuuhhn…"

Loona was the first to come down, groaning as she pulled herself off the Unicorn. Then without warning, she slowly started pulling her shaft free of the Principal's anus, even now Loona could feel the anal walls desperately gripping at her softening cock as it slid over the top of her knot, feebly clenching around every inch until it finally slipped free with a loud *POP*, allowing her cum to leak out onto the rug. "Ahhh… now that was satisfying~"

"Ahhh… uuughh…" Was all Gingersnap managed to mumble between her deep breaths with her tongue hanging out of the side of her mouth.

Staggering to her feet, Loona shakingly reached for her bookbag and pulled out a pack of cigarettes, casually snapping her fingers to summon a lavender flame and light it. The Hellhound took a puff before gazing down at the quivering, shivering mess of a Unicorn on the floor with a smirk. "Congratulations, you've earned yourself five decades." Was all she said before she reached for her Grimoire and started chanting again, the symbols in place slowly dissolving away as a larger symbol appeared on the floor.

Fading in and out of consciousness, Gingersnap could only make out the blue flames engulfing the entire room, with the Hellhound's voice echoing through the wind…

When she finally woke up, the Sun was setting… and everything was gone.

The Hellhound, the symbols, all of the seed and fluids that had coated the rug…

The only thing that remained.. was that aching pain in her ass… and the memory of Loona's words.

'Five more decades, huh…?' Gingersnap thought as she staggered to her feet, her legs feeling like jelly as she slowly regained her composure.

After making sure everything was tidy and presentable for tomorrow, the Principal stepped out of her office and locked the door, already thinking about which Unicorn would be her next target as she walked down the hall towards the school exit.

After all, she had 50 more years until their next meeting… and oh-so-many students to seduce…

Author's Note

This Story was seen earlier on February 28th, 2023 by my generous supporters on my pay-to-write sites.

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