Overwhelmed and Overthrown

Chapters

Chapter 1
Chapter 2
Chapter 3
Epilogue

Chapter 1

Tossing moving a pillow to the corner of the sofa, Sombra eased himself down and stretched his legs. Digging into his pocket, as his feet hung over one arm of the relatively small couch, he retrieved his phone and made a note for himself. His furniture, much like his cramped apartment, was hardly suited for a King, although things could certainly be worse.

Twilight Sparkle, after being crowned as the Princess of all Equestria, had apparently been stricken with a change of heart. She’d resurrected Sombra, apologize for vanquishing him twice, and given him a pardon for his crimes, so long as he agreed to play nice and integrate with society. He’d leapt at the chance, of course, yet he’d been left as an ordinary citizen.

His castle had been replaced by an inglorious single room apartment, his riches and fineries had all been confiscated and redistributed to the ponies of Equestria, and he was left with a temporary bit of unemployment money, his crown, and his cape. It was beyond demeaning but, alas, his torments didn’t stop there.

Being stripped of his regal title had been bad, but having to live as just another pony had been far, far worse. He’d tried working ordinary jobs, at first, although each and every one was downright awful. It was only when an effeminate young stallion, one of his previous coworkers at the Hay Burger, had commented on his physique did he have a eureka moment. Even if he was no longer considered a true royal, that didn’t mean he couldn’t be worshiped.

Abandoning his position at the fast-food restaurant, he applied for employment at a local strip club - the Princely Pole. Making his way to the establishment, after purchasing and donning a pair of leather pants and a skin-tight tank top, he’d walked in like he owned the place and politely asked to speak with the proprietor. After waiting for a few minutes, the owner showed up, took one good look at him, and hired him on the spot.

He was and always had been an absolute stud. Tall, astonishingly well built, and with damn near adonic features, Sombra never failed to draw the attention of mares and stallions alike - even if he only had any interest in the latter. Regardless of his preferences, his stunning good looks, charming smile, and immense endowment quickly made a rather favorable, albeit salacious name for himself.

The best part about becoming an adult entertainer wasn’t the money or the attention - no, it was having open access to any number of his adoring fans. If someone caught his eye, it was a simple affair to chat them up, get their number, and woo them into his chamber. Sweet stars above, in the few weeks since he’d started stripping, he’d already bedded no fewer than half a dozen young stallions!

This very evening, he was awaiting on a twinkish suitor to come knocking at his door. The lad, named Thumbtack, had paid for a private dance on two separate occasions and had gone so far as to offer him money for additional services; he’d declined, of course, but exchanged numbers with the stallion. After texting back and forth for a few days, with a fair bit of flirting and sinful promises flying between them, they’d settled upon a time for him to appear at Sombra’s apartment.

The phone in his hand vibrated, followed by an announcement popping up on the device. Smiling, realizing his guest was just outside, he pushed himself up and sauntered to the entrance. Brushing his mane back, making himself slightly more presentable than he already was, he opened the door and put on his best wolfish grin.

“Hey,” the stallion greeted, smiling sheepishly at him. Short, slender, and relatively plain looking, the little twink wore a simple t-shirt and jeans. His short, unkempt mane, a dark grey, complemented his stone blue hide and brilliant yellow eyes wonderfully.

“Please, come in,” Sombra intoned, stepping aside and baying his guest to enter. As the twink walked by, he noticed a book bag slung on the stallion’s shoulder. “Brought something fun for us?”

“Well,” Tack began, turning as Sombra closed the door, “I did bring something that I thought you might like - then again, I’m not sure if you’re into that sort of thing…”

Sombra chuckled, amused at the lad’s timid demeanor. He had little doubt that Tack’s reservations would soon melt away, as soon as they were undressed, but only time would tell. More than ready to entertain, he waved towards his open bedroom. “Perhaps we can discuss this little notion of yours somewhere more comfortable…”

Tack’s jaw flapped for a moment, before he nodded. He really was cute - so small and inexperienced looking, half of Sombra’s size, and only just having reached adulthood. The lad was like a deliciously ripe fruit, just begging to be plucked. As the King walked past, leading the way, he followed closely behind his host.

Strolling into his room, with his guest right on his heels, Sombra smoothly pulled his shirt up and over his broad chest. Considering what he did for a living, and what he planned to be doing shortly, he saw no reason to stay dressed. Reaching the bedside, he turned towards the stallion and cast the garment aside.

Slowly, sensually, his hands wandered to his crotch. Unbuttoning his pants and leisurely unzipping his fly, he smoothly pulled the article down his sculpted thighs. As the waistband of his slacks passed over his groin, inch after vascular inch of his stallionhood appeared. Even semi-flaccid, the thing was well above the usual size.

Whereas most stallions sported erections averaging six or seven inches, his tool hung limp at a staggering eight. When fully aroused, the thing was nearly a foot long and thicker than a beer can. Unfortunately, his immense endowment was a bit of a double edged sword - in that, he’d met a relatively small number of boy-toys who weren’t able to fully accommodate someone of his size.

Releasing his pants, letting the article fall to the floor, he chuckled. “Your turn…”

Setting his book bag to the side, Tack hastily disrobed. His build, much like the rest of him, was nothing terribly remarkable - then again, he’d assumed as such. Covered in lean muscle, sporting a moderately impressive cock, the lad was just what he’d been hoping for. The young stallion was already rock hard, likely dying to get the cum fucked out of him, which made the moment all the more savory.

Stepping closer, Sombra brought their groins together. The contrast of their equipment was jarring, to say the least. Even soft, his stallionhood was nearly double the size of his guest’s equipment. Though it was by no means necessary, he wanted his visitor to feel the slightest bit of intimidation. They both obviously knew who the superior stallion was, but showing off a bit always served to wet his carnal appetite.

“Quite the exquisite little dish, aren’t you?” Sombra purred, tracing a finger up his guest’s chest.

“I...I try,” Tack gulped, glancing down at his bag.

Sombra piqued a brow, curious as to what in Equestria could have held the lad’s attention. Leaning in, breathing hotly on his guest’s ear, he smirked. “There must be something awfully splendid in there, for you to take your eyes off of me.”

“I...It’s actually something for you,” Tack admitted, awkwardly retreating and leaning over to fetch the bag.

The remark threw Sombra further off guard, leaving him silent. It was rare for someone to bring him a gift, especially before he’d thoroughly ruin their throat or ass - still, he wasn’t opposed to humoring the lad. Stepping back, crossing his arms over his chest, he watched the stallion rummage about in his satchel.

“I brought these,” Tack murmured, holding out a french maid outfit and several accoutrements.

“Oooooooooooh,” Sombra hummed, his smile broadening, “I think you’d look quite charming in that.”

Tack rubbed the back of his neck and averted his gaze, as he extended the uniform towards his host. “They’re for you…”

Sombra blinked, wondering if he’d misheard his guest. “Excuse me?”

“Ok, not to gush, but you should really consider including a few feminine articles in your acts. Your glorious mane, those bewitching crimson eyes, that succulent ass of yours. Trust me, with a body like yours in an outfit like this,” Tack fawned, peering down at the uniform, “you’d have even more stallions throwing cash on stage.”

Eyeing the costume, Sombra weighed his options. He had entertained the notion of wearing something a bit more marish, yet he’d never actually given it a try. He did keep his nails painted scarlet, but he’d adopted that habit ages ago. While he was extraordinarily masculine, with slabs of chiseled muscle heaped about his frame, his rump was relatively large and pillowy. His pecs, if pressed together, were undoubtedly large enough to fill a small bra and, although he wasn’t too fond of such a look, he knew there were a great many who were.

“You don’t have to, if you don’t think you’ll look good in it,” Tack sighed, shifting uncomfortably.

“Give me a moment,” Sombra grunted, walking past and snatching up the apparel.

The mere mention of not looking good was the straw that broke the camel’s back. He felt sure that he could pull off virtually any look imaginable, such was his self-confidence, so he was effectively goaded to prove it. Strutting into his restroom, he closed the door behind himself. Since he’d never tried on such garments before, he’d rather his guest not see any potential struggle with donning the getup.

Within the confines of his bathroom, he gave himself a moment to study the outfit. It was, for all intents and purposes, a mockery of a proper maid uniform; the dress was too short, there was a large opening over the chest, and the entire garment reeked of obscene appeal. He couldn’t say he was terribly surprised, given the depraved nature of its intent, though it did manage to give him a small chuckle.

Slipping into the outfit was, to his surprise, a relatively simple affair. Either Tack had a damn good eye for guessing measurements or, more likely, he’d asked some of the Princely Pole’s staff about his clothing size. WIth the main article clinging to his torso, giving his massive pecs and almost breast-like look, he completed the look by putting on the accompanying fishnet leggings and gloves. The hardest thing to wiggle into, by far, was the pair of panties he’d been given.

The mare’s undergarments simply weren’t designed to house a stallion’s equipment - let alone a package of Sombra’s mammoth caliber. After minutes of toil, adjusting and readjusting the laced fabric of his loins, he eventually gave up. The titanic swell of his flaccid length and barely restrained nuts were laughable, yet the delicate material held. With the final piece of the ensemble in place, he looked to the mirror to appraise himself.

His reflection stared back at him and, of course, was just as resplendent as he’d imagined. The uniform, while a bit odd for a stallion of his build, somehow accentuated the few marish features he had to nigh unfathomable levels. His long, luscious mane, the way his chest filled out the top, how the skirt draped over his thighs and tush was strangely captivating. He was still quite obviously a male, yet his masculine appeal was blunted substantially by the uniform.

In the end, he wasn’t bothered by his new look. As he opened the door and proceeded into his chamber, he hummed proudly to himself. Soon, he’d have Tack bent over and impaled on his mighty stallionhood - doubtlessly mewling like a mare who’d been claimed. Putting a bit of swagger into his step, he paused in the doorway and cleared his throat.

“I hope I’m just as ravishing as you’d hoped - then again, I know I am,” he conceitedly snickered.

“Sweet Celestia,” Tack reverently breathed. Walking over to the titan of a stallion, he gently rested his hands on the King’s hips. “You’re just beautiful,” he sighed, pressing his face against his host’s chest.

“Why thank you. Now, if we could…” Sombra trailed off, as the lad’s hand wandered under his skirt and to his backside. The sensation of his guest’s fingers slipping into the cleft of his ass snapped him back, leaving him to softly push the stallion away. “That’s cute, really, but usually it’s the bottom who gets that sort of treatment.”

“I thought you were going to bottom,” Tack admitted, a wounded look crossing his face.

Sombra recoiled slightly, caught woefully unprepared by the assertion. “And you presumed that I’d allow you to top me because…?” he let the question hang.

“Well, you’re just so beautiful and talented that I expected you to be a switch. Even if you’re not, every top I’ve ever met bottoms sometimes - you know, just to scratch that itch,” the lad explained matter-of-factly.

The King pursed his lips, forcing himself not to say anything. He had, in fact, never bottomed for anyone, but he couldn’t freely confess to that. His exile had been long and the world had changed, so he couldn’t say for certain if Tack was being honest with him or not. Regardless, he simply couldn’t admit to being ignorant of such things!

He was King Sombra, the King Sombra, lascivious lord of all he surveyed! If mixing things up with some mere peasant would further bolster his experience and renown, so be it. Staring at his guest’s erection, he stifled a laugh. Tack’s endowment wasn’t the smallest he’d ever seen, but he doubted it would give him any trouble. Hell, given their sheer differences in size, he probably wouldn’t even feel it!

A predatory grin split his features, as he looked to his visitor’s face. “How about a friendly wager. If you cum before me, I’m going to fuck you until you can’t stand straight.”

Tack looked to the floor and rubbed his chin, but it only took him a second to reply. “Alright. But if I win, you have to wear that outfit Friday Night at the club.”

Sombra laughed darkly at that, unable to contain his amusement. The thought that some commoner could make him climax from being rutted was ridiculous. Extending a hand, imagining how best to absolutely demolish his guest’s hole, he stepped forward. “So be it…”

Tack positively beamed, briskly shaking the King’s hand before pointing to the bed. “If you want to get comfortable, we can start.”

“Hmmph,” Sombra huffed, sashaying to the mattress.

Leaning forward, crawling onto the blanketed surface, he presumed an all fours position. Even if he had allowed himself to get serviced by some plebeian, that didn’t mean he had to look his partner in the eye throughout. With his knees resting on the edge of the bed, he awaited the trial to begin.

“Ok, I’m gonna get started. Just give me a sec,” Tack called out from behind him.

“My thanks,” Sombra grumbled.

To think he would ever find himself in such a scandalous situation was absurd. Dressed in some slutty mare’s uniform, with his barely concealed ass and package presented like he was some common whore, it was as if the world had gone mad! The funniest part was that the lad actually thought he had a chance of winning this silly competition - well, it would be funny, if it wasn’t downright pathetic. After all, how on earth could painfully ordinary pony ever dream of -

Sombra’s eyes flew open, his arms went rigid, and he gasped, as something slipped into his backdoor. The move had been so sudden that he hadn’t had any time to react. Tack had simply tugged his panties to the side, exposed his taut pucker, and thrust into him. He slowly exhaled, shivering slightly, as the intrusion worked deeper.

It was a strange sensation, though not an unbearable one. Growing accustomed to the feeling, he relaxed to a degree - that was, until something peculiar happened. It was almost like the twink had pressed a button inside him, sending sparks of pleasure surging through his frame. Tack stopped, fixating on the particular spot within his rump.

“There it is,” the lad hummed, massaging the tender area.

“What are you - Mmmmn,” Sombra half growled, as something else pressed into him.

“Just warming you up a little. You seem pretty tight,” Tack nonchalantly responded.

The statement caused Sombra to look back, for a fleeting moment, before hanging his head. He shouldn’t - no, couldn’t let his guest see his surprise. What he’d assumed was a dick was, in actuality, only his partner’s fingers. It made sense, in hindsight, but the digits in his chaste derriere felt far more substantial than they actually were. Steeling himself, he allowed Tack to loosen him up.

One small saving grace was that his visitor had brought a bottle of lube with him, making the experience marginally less taxing. As degrading as it was, allowing some peasant to toy with him, he kept silent. Soon enough, he’d wreak havoc on the young stallion and leave him a gibbering, cum filled mess.

“Alright, that should do it,” Tack began, withdrawing his slickened fingers. “You ready?”

Hearing his guest move, feeling a hand rest on his hip, Sombra kept his eyes averted. “Just remember our little wager.”

“I’ll do my best,” the lad humbly replied.

The warm, blunt tip of what could only be Tack’s stallionhood pressed against Sombra’s entrance. Despite the absurdity of the situation, he couldn’t bring himself to be submissive. Scowling, refusing to be used like some ordinary harlot, he seized the initiative and rocked back. The move sent the battering ram-like head into his backside.

His impulsivity and domineering streak instantaneously dealt him a crippling blow. Either he’d grievously underestimated the lads size or overestimated his body’s ability to cope with the penetration - either way, he swiftly realized his mistake. He shuddered, as his guest’s stallionhood ground into his depths.

“You ok?” Tack asked, drawing to a halt.

“I...I’m fine,” Sombra stammered, doing his damnedest not to tense up.

“I just wanted to be sure. Almost halfway there,” the twink sighed, gently driving his hips forward.

Sombra swallowed hard, taken aback by the admission. He’d only managed to take half of the stallion’s length, yet he felt positively stuffed. Bracing himself, feeling the hot length of pony meat worming into him, he grit his teeth. It was only when something immensely fat and girthy pressed against his hole did he the lad relent.

He thought he’d earned himself a breather, presumed that Tack was too enrapt with the divine sensations his body afforded, but he’d been dead wrong. Without saying a word, the twink withdrew slightly, tightened his grip, and started thrusting. Subconsciously, he grasped at the blankets, as the pleasure from before redoubled in strength.

As shameful as it was, the blissful sensations accosting him were slowly taking a toll. Setting his jaw, his body was jostled ever so slightly by the impetus of his partner’s steady movements. What little discomfort there was bled away, gradually dissolving under his Tack’s ministrations. Realizing he’d been holding his breath, he exhaled.

“You don’t know how long I’ve dreamt of this,” Tack admitted, softly bucking away.

Sensing an opportunity to drive the lad closer to his limit, Sombra seized the moment and struck. Throwing his ass back, fully hilting his guest, his recklessness was his undoing. Tack’s medial ring popped into him, crushing his tender prostate and causing his semi-flaccid cock to smear the interior of his panties with pre-cum. Despite himself, a throaty groan escaped him.

Almost immediately, presumably taking his move as a sign of enjoyment, Tack began rutting him harder and faster than before. It was all he could do to hold himself up, desperately clinging to the linens for support. He’d unwittingly signaled the twink to pull out all the stops, causing the lad to pound his ass like a beast possessed - or so he thought.

Tack shifted, altering the angle of his plunges to more directly stimulate the delicate organ in his rear. Screwing his eyes shut, he bit his lip to stifle himself. There was no denying how infuriatingly sublime it felt, though he couldn’t show weakness. It wasn’t his fault that his body was unused to such deplorable treatment! Blindly reaching for a pillow, hoping to muffle any unseemly noises he may make, his balance was upset by a particularly forceful thrust

Having balanced himself on one arm, while he grabbed for a cushion, his stability was compromised. His chest crashed to the mattress and his legs parted slightly, as the carnal assault continued. Tack was uncaring, either too incompetent or too selfish to notice his plight, as he plowed him like a mare in heat. Suffering the full brunt of the twink’s assault, he desperately pulled the pillow to his face.

“That - Huff - good, huh?” Tack jeered, above the sound of their bodies colliding.

Sombra couldn’t respond, with his muzzle buried in the cushion - even if he could, he wasn’t sure he’d be able to speak properly. To say it was an odd situation would be a complete understatement. His frustration and annoyance over being so wantonly used was clear, yet some part of him pined for more of the maddening pleasure coursing through him.

As disgraceful as it was, the sensation of being rutted was unparalleled. Whether or not it was due to his waning control or the skill of his partner, he couldn’t be certain - nevertheless, he felt as though he was losing himself. Sinking his teeth into the cushion, feeling his stallionhood drooling within his lacy undergarment, he struggled to maintain composure.

The sound of Tack’s heavy breathing, paired with the rhythmic Plap Plap Plap of his rump slapping against the lad’s waist was a sinful symphony. He had little doubt that, without the pillow against his face, it would take every ounce of his concentration not to make a noise. His only consolation was that he knew it would be over soon and that he’d be able to reap sweet vengeance upon the stallion who had dealt him such a shameful blow.

Sadly, fate conspired against him. The lad movements ground to a halt, moments before he felt the warm length of stallionhood being hauled from his abused tush. There was simply no way Tack had finished up that abruptly, so he turned his head and glanced over his shoulder. Peering past the obsidian strands of his luxurious mane, he spied the svelte stallion applying yet more lube to his turgid dick.

“Roll over,” Tack politely instructed. “If it’s ok, I really want to see that gorgeous face of yours.”

The flattery stroked his ego and spurred him to comply, even though his confidence had been shaken. He simply wasn’t accustomed to being treated in such a lascivious manner and, as much as it pained him to admit it, the twink’s skill was undeniable - still, like it or not, he’d made a wager. Shuffling up the mattress, relinquishing his saliva streaked pillow, he acquiesced.

Easing himself down and rolling onto his back, he looked down his frame. Tack crawled onto the bed, between his parted legs, and smiled graciously down upon him. Sombra didn’t need to be told or asked what to do, so he quietly lifted his legs, braced his feet on the mattress, and lifted his waist; he doubted the lad would be able to lift him, given their difference in size and strength, leaving him to give a bit of assistance.

Easing himself back into the massive stallion’s confines, Tack set to plowing Sombra like a field in spring. Unlike when they’d first began, the twink wasted no time in falling into a fast, savage rhythm. With his hands resting to either side of the King’s broad torso, he leaned forward and rested his cheek on the former tyrant’s pec.

Sombra thought it was cute - that was, until the lad sprung the trap. Biting down on the fabric over his chest, drawing the cloth down to expose one of his onyx nipples, he craned his neck and latched his lips around the sensitive bud of flesh. Completely unprepared for the affection, he whimpered and reflexively bucked his waist up to meet Tack’s pounding hips.

It was bad enough that he was quickly succumbing to the enjoyment of being railed out, but the unexpected attention to his teat elevated things to an entirely new level. Cracking one eye open, he gazed at his guest. There was something disturbingly arousing about watching the small stallion rut him - sure, it wasn’t what he was used to, but the sight and sensations were beyond reproach.

Lying there, being fucked like a filly on prom night, Sombra was at a loss. It felt good - no, better than good - it felt amazing. Synchronizing their movements, raising his waist to meet his partner’s plunges, he wasn’t sure if his motions were for Tack or for himself. Since they’d shifted to a missionary position, his prostate was accosted with every thrust.

Opening one golden eye, meeting his crimson gaze, Tack gave his nipple a parting kiss and withdrew. Slowing to the smallest degree, the twink leaned back and grabbed ‘hold of the King’s knees. Wondering what the lad was up to, he got his answer all too swiftly. In a feat of herculean strength, his legs were lifted and pressed upwards.

Sombra shouldn’t have been too surprised, considering his visitor was an earth pony, yet the mighty action left him stunned. Contorting him like a pretzel, Tack inched closer to his upturned rear. The small stallion’s arms slipped behind his knees, as he found himself peering up into the lad’s bewitching eyes.

As jarring as the repositioning was, nothing could have prepared him for the abject rapture which soon met him. Without preamble, Tack started screwing him with the unrelenting force of a war machine. Pinned, bearing the full brunt of the little stud’s carnal might, he mewled uncontrollably.

Everything in the world was drowned out by the unfettered pleasure that threatened to rob him of his sanity. A pressure and heat was welling up within him, unlike anything he could describe. Without having so much as touched his stallionhood, he felt as though he was a hair's breadth from release. Each plunge caused Tack’s thick medial ring to crush his overly stimulated p-spot, pushing him closer and closer to the edge.

Faster and faster, harder and harder, the lad mercilessly pounded his ass like a jackhammer. Clamping his eyes shut, thrashing his head from side to side, he fought with every fiber of his being to resist the urge to succumb - until it was too late. In one flawed move, hoping to see some sign of his partner’s imminent release, he peered upward.

Framed by the ceiling light, lovingly staring down at him with a quaint little smile, Tack’s brilliant eyes met him. He opened his mouth, drew a breath, and uttered three fateful words. “Cum for me…”

The request was Sombra’s undoing. His toes curled, his ass spasmed around the throbbing stallionhood filling him, and he howled to the heavens. A torrent of seed gushed from his tool, slathering his barely contained loins in his scalding, viscous essence. Awash in ecstasy, teetering on the brink of madness, the unthinkable happened.

With a triumphant snort, Tack slammed his waist forward and hilted. Sombra’s voice cracked and every muscle in his body tensed wildly, as the stallion’s hot seed surged into his depths. As impossible as it seemed, his own climax redoubled in strength. Braying out, with tears streaking his cheeks, he lost himself to the maelstrom of bliss.

He had no way of knowing how long their bodies had stayed entwined, teetering on the brink of consciousness, but the moment finally came to an end. Releasing his legs, letting them flop limply down onto the mattress, Tack retreated. With the softening length unsheathed from his battered and slightly agape pucker, his hole ineffectually grasped and winked at the void. Seething spunk leaked from his backside, coating the cleft of his tush and dribbling to the bed sheets below.

“I...I guess that settles that,” Tack croaked, flopping down beside the substantially larger stallion.

As the lad turned to face him, lovingly draping an arm over his chest, Sombra stared blankly at the ceiling. Not only had he lost, but done so in spectacular fashion. He’d been humiliated, plain and simple, having suffered through possibly the most powerful orgasm he’d ever had. Beyond unbelievable, the experience was a revelation - albeit an exceptionally humbling one.

Tack hummed contentedly, amorously stroking the King’s bare and sweat streaked chest. “So I guess you’ll be wearing that costume next Friday...”

Rubbing salt in the wound, mentioning that he’d have to wear such a slatternly outfit for the masses, pushed him to act. He simply couldn’t parade about on stage and show himself off in such an unseemly getup; it would ruin his regal image and the air of domineering superiority he’d worked so tirelessly to cultivate. Licking his lips and drawing a breath, he did what he had to do.

“A rematch,” Sombra coughed, unwilling to look his guest in the eye.

“I...what?” the lad sputtered, cocking his head.

“A rematch,” the King repeated, only then stealing a fleeting glance at the lad’s face. “In two weeks, you will give me a rematch - double or nothing odds.”

“If you say so,” Tack purred, snuggling up against the titanic stud. “Just don’t be mad if you lose again.”

Sombra didn’t reply, too focused on the thoughts dancing around his head. Unmindful of the fact that bottoming had made him cum without even touching himself, he had his pride to account for. Reluctantly, he wrapped his strong, muscular arm around the lithe stallion’s back and accepted the embrace.

Though he’d been undone by his own hubris, he wouldn’t let the same mistake happen a second time. Replaying the events in his mind, dwelling on what techniques he could employ to best his twinkish foe, his cum-slick pucker hungrily seized upon itself. So long as he could wrestle control of his body’s budding urges, and possibly acquaint himself with the damnable sensation of having his backdoor used, he would be victorious...He hoped…

Chapter 2

Standing before the counter, adorned in a snug polo and pair of jeans, Sombra nonchalantly browsed the impulse items by the register. Travel sized bottles of lube, gift cards, condoms in various sizes, and mints lay neatly arrayed in a number of trays, but they weren’t what he was there for. Glancing over at the adult novelty shop employee, just as she finished ringing up his items, he smiled.

“Anything else?” the mare chipperly responded, gazing up at him.

“I’m afraid that will be all for today, thank you,” he intoned, preemptively fishing into his pants to retrieve his wallet.

“That’ll be one hundred and thirty two bits,” she chirped.

Handing over his card, Sombra sighed. He hadn’t intended on hemorrhaging that sort of capital on such a frivolous purchase, but desperate times called for desperate measures. Taking the opaque black back from the employee’s hands, after signing the receipt, he nodded farewell and saw himself out.

Hopping on one of the many buses that ran through town, he found himself back at his apartment complex in less than twenty minutes. One of the few benefits of living in a larger city was that nearly everything was accessible via public transit, allowing him to procure whatever he needed with relative ease. He had been saving up to get a car for himself, if only to make things a bit more convenient, which exacerbated his frustration with spending his hard earned money.

Casually strolling up to his unit and letting himself inside, he locked the door behind himself. Though the chances of anyone coming to pay him a visit were extraordinarily slim, the last thing he wanted was for anyone to see what he was about to do. Moving to the bed, he neatly arrayed the items he’d bought and studied them each in turn.

The first items, assorted within a clear plastic case, were a series of differently sized butt plugs; each was larger than the last, with the biggest being nearly two inches wide. Next up was a bottle of spare lube, which would eventually be used for some endeavor or another. Lastly, and most shamefully, was an average dildo - average in that it was substantially shorter and less girthy than his own colossal stallionhood. Despite its relatively humble dimensions, it would get the job done.

Considering he had slightly less than two weeks to prepare for his rematch with Tack, agreeing to meet the stallion in a contest of carnal prowess, he needed to prepare himself. Only a few short days ago, he’d been topped by the modestly sized lad and, much to his disgrace, been thoroughly rutted into submission. Swearing vengeance, with the promise of double or nothing odds, he’d challenged his slender nemesis to a second confrontation.

Under normal circumstances, he wouldn’t stoop so low as to buy paltry sex toys or marital aids - for heaven’s sake, he was a walking sex machine - but, sadly, he knew what needed to be done. His encounter with Tack had been profoundly demeaning, catching him ill prepared for the rutting he had received - as such, he would do everything in his power to prepare himself for their impending clash. He would not lose a second time...

Ferrying his purchases into the restroom, he made ready for the first of many trials. Fetching two small cameras from under his bed, which he typically used to film his exploits with fans and worshipers, he moved the small devices into the lavatory. It wasn’t like he wanted to record to record himself exercising his once pristine ass, yet he thought it was the best course of action.

Besides acquainting himself with having his wonderfully taut pucker used, there was the matter of his technique. Though he knew he’d be bottoming for the twink, that didn’t mean he couldn’t maintain control of the situation and dominate the lad - therefore, he would need to hone his skill to a razored edge. Once all his preparations were complete, with the toys washed, cameras tactically positioned in and beside the bathtub, and having given himself a thorough cleaning, he steeled his resolve.

Without toweling himself off, spying himself in the large mirror above his sink, he paused. Beads of water rolled down his brawny frame, following the contours of his sculpted and superbly massive musculature. It was a shame, really - there he was, a literal Adonis, about to flagrantly debase himself by despoiling his ass. Flashing his reflection a devilish grin, he flipped the wetted mane from his face.

“Don’t worry,” he chuckled, reassuring himself, “after you win - and you will win - you’ll wreck his ass so badly that no other stallion would be able to satisfy him.”

Tapping the cameras, setting them to record, he eased himself down onto the edge of the tub. Everything was ready, with the implements of his practice resting on the floor, so there was no need to delay the inevitable. Snatching up the bottle of lube and slathering one hand in the gooey substance, he shuffled his behind backward.

With his rump hanging over the basin, he reached behind himself. It was a bit awkward, given his sheer bulk, but his digits soon delved into the cleft of his tush. Questing deeper, between his well developed buns, his efforts were soon rewarded. As he felt his silken, ebony pucker, a shiver ran up his spine.

Sombra took a measured breath and closed his eyes. Exhaling slowly, he sank his middle finger into himself. The sensation was odd, yet not nearly as intense or demoralizing as having that infernal stallion’s tool plunging into him. Discovering the feeling of being penetrated wasn’t some unfathomable weakness was reassuring, to say the least, so he continued onward.

Loosening his hole for a moment, emboldened, he sank a second digit into himself. He smiled, while he experimentally probed his interior - sure, it wasn’t like he had penetrated himself with anything too girthy, but it was hardly as mind-bendingly pleasurable or ruinous as he had anticipated. Arching his back, he delved deeper.

Only a few inches into his exploration, he inadvertently stumbled upon what had to be his point of weakness. A bolt of pleasure shot through him, as his prostate was stimulated. While he had some experience with the organ, having fingered the occasional paramour to warm them up, this was different.

Arching his back, he prodded the delicate bulb. His size and the position he’d chosen made the endeavor nearly impossible, leaving him at an impasse. He was simply too burly to easily play with himself in such an embarrassing manner; fortunately, he’d planned for such a potentiality. Withdrawing his hand, he got to his feet, bent over, and plucked the medium sized plug and dildo from the floor.

Removing his shampoo and conditioner from the inbuilt shelf in the shower, placing them on the floor, he set the sex toys down and squeezed a hefty amount of lube onto each of them. Leaning forward, while moving the slickened plug to his backside, he braced one hand against the wall. The cool, molded plastic against his backdoor wasn’t nearly as welcoming as his fingers, yet he was undeterred.

Closing his eyes, attempting to stay relaxed, he pressed the plug into himself. Having a gradual taper, with a pronounced well at its midsection, the toy wasn’t terribly difficult to manage. Unable to see his progress, the thickest portion item pressed to and into his tail hole. With an all but audible Pop, having passed the girthiest point, the remainder almost instantaneously slid into him.

Reflexively, caught unawares by the sudden intrusion, the monstrous stallion clenched his ass. The plug’s base was lodged firmly against his pucker, causing the unintentional flex of his meaty backside to send the toy directly into his prostate. His knees buckled, the breath hitched in his throat, and the barest whimper escaped him. In spite of his mental fortitude, he was not prepared for the contemptibly wave of pleasure which swept over him.

Giving himself a moment to adjust, he peered downward. As his gaze wandered over his chest, between his tremendous pecs, he froze. His enormous, semi-erect stallionhood hung before his chiseled thighs. A lone strand of pre-cum dangled from the dip of his length, languidly creeping down to the basin below. His lip curled in disdain, angry that his body would betray him.

Straightening up, with the toy trapped within his rump, he grunted in frustration. He’d only just begun, yet the insidious joy of such depravity was already tempting him. Like a damnable siren’s song, some part of him pined to do nothing more than to masturbate. Squashing the thought, he rebelliously clamped his tush around the toy.

Drawn deeper, forced against his tender p-spot, the plug sent a second jolt of bliss coursing through him. Dauntless of how banefully good it felt, the stallion flexed a second time, then a third and a fourth, until he was rhythmically working the toy in his ass. It was akin to torture, albeit a despicably enjoyable one.

Clamping his eyes shut, trying his damnedest to concentrate, he had little doubt that the pair of cameras were dutifully recording the outrageous display. Subconsciously, as if attempting to sabotage his efforts, his hand wandered up his frame. Tracing the peaks and valleys of his abs, working up towards his chest, his digits drifted to his pecs.

Without realizing it, too fixated on battering his insides with the toy, a finger grazed one obsidian nipple. Willing his body to obey, moving his arm away from his torso, he scowled. As his left hand blindly extended outward, hoping to place it on the adjacent wall, something soft and slick toppled into the tub. Cracking one eye open, wondering what he’d knocked off, his brow furrowed.

Lying in the basin was the dildo he’d set on the shelf. The damn thing virtually taunted him with its meticulously crafted silicone length and served as a reminder of his failure to be a god in all carnal affairs. Bending forward and retrieving the dong, he sneered. When, not if, he vanquished Tack, he’d be sure to leave the wicked marital aid jammed in the lad’s tush - for now, he needed the vile thing.

Reaching behind himself, grabbing hold of the plug’s base, he pulled. Wrenching the conical toy from his backside, stifling a groan as it cleared his hole, he let it fall to basin. Surely - surely he was ready to handle something a bit closer to the genuine article. He was Sombra, King of all he surveyed and an unmatched paramour of renown! With his hauteur renewed, he wetted the dildo’s suction cup base and turned.

Affixing the toy to the tiled wall behind himself, eyeballing its placement, he faced away and seized one glute in each hand. Prizing his buns apart, guided mostly by feel, he shuffled backwards. The vascular toy glided between his legs, nudging his pendulous nuts. Scrunching his snout, he readjust his positioning.

He squatted slightly, lowering his waist, before making his second attempt. His next try was met with success, leaving the dildo’s blunted tip pressed against his entrance. Steadying himself, taking a metered breath, he rocked back. The battering-ram like head ground into him with little effort, likely because of the slightly thicker dimensions of the plug he’d just used.

With the utmost care, he backed up and steadily impaled himself. Though it may not have been as broad as the other toy, the dong was nearly double the length. As his depths were filled with the silicone shaft, the resistance progressively grew. Much like an actual stallionhood, the dildo grew fatter towards the base. He shuddered, as the medial ring wormed into his confines and over his prostate. Realizing he only had an inch or so left, he tenaciously hilted the tool.

The cold touch of tile on his rump, paired with the abject feeling of fullness the dildo afforded, was a small triumph, but he was far from finished. Simply having something lodged in his backside could hardly be considered training, since there was no movement involved. Placing his hands on his knees, lest they stray to his chest or groin, his legs tensed.

Thrusting his hips, allowing a few inches to slip from his behind, he languidly began working the sculpted shaft. Gently moving forward and back, he pistoned himself on the dong. Every backward motion caused the ass to press against the wall, as he sluggishly screwed himself. As he acclimated to the sensations accosting him, the wretched feelings of delight once again found him.

Attempting to distract himself with thoughts of anything but his current situation proved fruitless. Despite his best efforts to ignore the growing warmth and tingling from deep within him, his movements quickened. Though his conscious mind was hellbent not to relish the experience, his anatomy had other plans.

His stallionhood swayed between his legs, leaking copious amounts of his pre-cum to the basin as a testament to his unwanted enjoyment. Looking around, while he humped back upon the dong, he searched for something - anything to divert his attention; this was practice and he wasn’t trying to have fun. Peeking to his right, noticing an askew towel on the nearby rack, he straightened up and reached for it; the subtle shift, while small, altered the trajectory of the dildo.

He gasped aloud, as the sensitive organ in his ass was pummeled. Acting on impulse, standing to nearly full height, he clutched the towel rack and continued rutting himself. It felt astounding, far better than the plug or his fingers, and caused his subconscious urges to wrestle control of his body away from his higher thoughts. His free hand dangled limply for a fleeting moment, before meandering up his side.

Throwing his ass back harder and faster with every passing second, a blissful fog settled over him. It was almost as if he was acting on autopilot, wantonly pumping the dong in and out of his pucker. His annoyance bled away, as did his strength of will, overwhelmed by a singular thrill welling up within him. Before he realized what he was doing, he was pinching and twisting one of his onyx black nipples.

Confused, excited, and with the fires of passion burning brighter than ever, he persisted. Unabashedly fucking himself on the toy, while he teased one teat, his motions grew frenzied. A pervasive heat spread through him, causing his legs to tremble slightly, yet he did not slow. Panting, compelled to persevere, he crossed a threshold.

Ramming himself back, jackhammering the dildo’s girthy ring over his p-spot, the world seemed to explode around him. The most marish, effeminate moan of delight slipped past his lips, as he climaxed. Though his stallionhood was far from at full mast, a veritable tsunami of seed erupted from his cock.

His toes curled, his backdoor needily convulsed around the toy, and his eyes rolled to the back of his head. Suffering through one of the strongest orgasms he had ever known, his existence was drowned out by pure, unrefined rapture. Desperately holding tightly to the towel rack, lest his legs fail him, he dragged air into his lungs.

The hormones raging through him slowly subsided, the ecstasy dulled to a pleasant haze, and his higher functions steadily returned. For the second time in less than a week, he’d cum without so much as touching his dick. Unsteadily stepping forward, hauling himself off the slickened shaft of silicone, he wearily peered through his bathroom door towards his wall-mounted clock.

One small consolation was that he’d lasted for longer than he had with Tack, yet he was less than pleased with his performance. If nothing else, he considered it a small accomplishment and a reassurance that he could improve his endurance. Turning on the shower and pulling the curtain, he washed the lube and spunk from himself.

With over a week left to make ready for his showdown with Tack, his confidence swelled. So long as he doggedly trained, honing his body and refining his techniques, he would surely succeed in besting the twink. Dwelling on his past defeat, and imagining how he could best make use of his soon to be subdued foe, he finished his wash down and gathered up the pair of cameras.

The remainder of his evening was spent begrudgingly reviewing the footage of himself, reading articles on how best to bottom, and scheming on what his next steps would be. Practicing in the bathroom, while convenient for cleaning up, wasn’t exactly ideal or all too realistic, so he jotted down a few notes. Since he didn’t have to work tomorrow, he planned another trip to the adult shop.

Through his studies and research, he came to the conclusion that he had two more purchases to make: a larger dildo and a weighted base to affix his toys to. He wasn’t exactly thrilled with having to spend more of his hard-earned bits, yet he felt it was necessary. Buying a phony stallionhood that was bigger than his adversary, and having a means of using it in various places around his apartment, would surely give him the edge he needed.

After many hours of investigation and reflection, as well as a simple meal, he crawled into bed for the night. Once all of this nonsense was finished, and the score was settled, he’d discard or gift his small trove of sex toys to an acquaintance - after all, it wasn’t like he’d ever willingly entertain himself with such things. Resting his head on the pillow, pondering about his future conquests, he drifted off to sleep.

…

Sadly, the former villain’s slumber wasn’t quite what he’d consider restful. Throughout the night, his dreams were plagued with all manner of licentious, wholly unwanted illusions and fantasies. Wild thoughts which his conscious mind would want no part of assailed him, seemingly from the moment he closed his eyes, although he couldn’t fathom why.

He’d dreamt of being used by countless stallions, of various sizes, in all manner of unimaginably lustful ways. Licking them, sucking them off, flagrantly displaying his ass for them to use; things that his alert self would never allow. The most troubling thing about it all wasn’t how he’d acted, nor the inconceivable physical pleasure which he derived from zealously servicing and being used by them - no, it was the fact that he loved it which haunted him.

It was almost as if the universe was conspiring against him, pushing him to embrace the role of being a bottom. Shaking his head, throwing off the covers, he went to swing his legs over the side of the bed but paused. A cool puddle of his jizz rested beside him on the sheet, clear evidence of his somnambular transgression.

Gathering up his linens and cramming them into his laundry bag, he rinsed off and got ready to start the day. Once dressed, after setting a pot of coffee to brew, he marched downstairs and started a load of laundry. His early morning, while regrettable, gave him plenty of time to tidy up before the adult shop opened. Shunting his frustrations in a more useful direction, his lamentable night bolstered his resolve.

The following hours flew by, as he cleaned his home and finished with the laundry. While the occasional musings of girthy stallionhoods stuffing his backdoor were vexing, he managed to finish up with everything before the bus was scheduled to arrive. His wait at the stop was a short one and, before he knew it, he was trundling along in one of the massive vehicles.

His trip to the shop would be quick, so he kept himself occupied with his phone. Dallying away the time, checking his social contacts and inspecting the work schedule for the upcoming week, he sighed. Someone had apparently shuffled his days around, leaving him with only the upcoming Thursday and Sunday to relax. The bit of bad luck wouldn’t affect him all that much, and it meant a bigger paycheck, but it would rob him of opportunities to develop his mind and body.

As the bus rolled to a stop, he approached the driver and offered his most charming smile. “I hate to be impolite, but could you give me just five minutes? I just need to run in for one thing, I promise,” he intoned.

The operator, a rather wizened and portly mare, immediately blushed and dismissively waved at him. “Just don’t take too long,” she snickered, peering into his crimson eyes.

“My good mare,” Sombra murmured, sweetly taking her hand and giving it the daintiest kiss, “I’ll be back in a flash.” Seeing her cheeks go a bright shade of crimson, hearing her giggle like a little filly, he briskly departed and made for the shop.

There was no need to dally, since he already knew what he needed. Jogging into the shop, snatching up the weighted base he’d seen the day before, he moved to the startling array of insertable toys. Browsing over them, looking for one which would fit the bill, he paused. There, resting at the top of the rack, had to be one of the most impressive dildos he’d ever seen.

In clear plastic case, with the name Mare Breaker emblazoned beside the price tag, it appeared to rival his endowment at full mast. Reaching up and taking the box in his grasp, he moved towards the register. Though the dong was a touch larger than what he’d intended, he was inspired; if he could master taking something comparable to his own magnificent cock, Tack’s pitiful tool would be little more than a joke.

Setting the items he’d gathered on the counter and presenting his card, he smiled cheerfully at the employee. “If you could be quick, I’d be most appreciative.”

The nondescript stallion working the register nodded, rang up his purchase, and handed him a receipt. Snatching up his purchases, without waiting for them to be bagged, he rushed back out towards the idling bus. Leaping onboard and offering a hasty thanks to the driver, he found a vacant seat for himself. He couldn’t care less what anyone thought about his somewhat impulsive acquisition, but that didn’t stop a mare sitting across the aisle from commenting on it.

“Don’t hurt yourself on that, Big Boy,” she snickered, grinning cheekily over at him.

Sombra’s temper flared, spurring him to toothy smirk in her direction. “I assure you, I’ll have no trouble,” he boastfully chuckled, setting the items on the empty seat beside himself.

The rest of his round trip was made in silence, leaving him at his apartment complex well before noon. Scampering upstairs and to his door, with his investments tucked under one beefy arm, he fumbled for the keys and unlocked the door. His heart raced, as he locked up behind himself. Yes, of course this was the best plan! If - no - when he’d thoroughly broken in his ass with such a prodigious toy, the twink wouldn’t stand a chance!

Swiftly clearing the floor in front of his sofa, he linked his laptop to his television. Watching his attempts from the night before while tackling the behemoth he’d just bought would kill two birds with one stone. Not only would he make the use of his time by working out his pucker and acquainting himself with something which vastly surpassed Tack’s size, but by analyzing the recording of himself. He was an absolute genius!

Setting the base he’d purchased in front of his TV, he ripped open the box of his new dildo. Feelings its heft in his palms, he appraised the meticulously crafted length. Traced with a long, angry vein, dark as midnight, and adorned with a set of meaty, sculpted nuts, it could almost double as a clone of his own equipment - almost. Unlike him, it had several flaws which were hard to overlook.

It wasn’t quite as large as him, it lacked any of his sublime body heat, and the glaring absence of any natural musk were all detractors, not to mention it wasn’t attached to a divine form like his own. There was no conceivable way a mere simulacrum could ever challenge everything he had to offer, yet there was nothing he could do. The thing would serve as an implement to his further progression to perfection, so it would have to do.

Licking the heavy-duty suction cup inbuilt in the bottom of the toy, he affixed the dong to the heavy platform on the floor. Weighing nearly fifty pounds, the base unit was a rather clever device; with a wide foundation, it had attachment points at various angles along the four sides and top. He’d be sure to put the hefty unit to good use, plowing himself in different positions using a variety of techniques.

Surveying the arrangement of his living area, approving of the space he’d left for himself, he walked to the laptop and set the videos of himself on loop. He’d already positioned his two cameras to document the event, in the hopes that further information could be gleaned from the recordings. With everything in its place made, there was only one thing left to do. Stripping from the simple shorts and t-shirt he’d donned for his brief mission to the store, he reached back and massaged his backdoor.

Warm, supple, and surprisingly juicy, the velvety ring of flesh compulsively winked at his touch. Some of the lube from the evening before must have remained within him, because he was able to slide a finger in with relative ease. Just for good measure, realizing that there could never be an excess of lube, he fetched a bottle from his entertainment center and squirted a liberal amount on his hand.

Bending over, he smeared the dong with the slippery goo, stood, and applied the remainder to his behind. Stepping over the towering toy, he took a wide stance and began to squat. Getting himself properly aligned had been easier than doing it in the shower, since he’d been unable to actually see if he was on the right course. As he descended, lowering himself further and further, the battering ram-like tip nudged his entrance.

Reaching between his legs, holding the toy steady, he gradually applied more of his weight. In spite of the mounting pressure on his pucker, his body seemingly refused to yield. Snorting, getting increasingly frustrated with his disobedient backside, he heaved his body-weight downward. The impetuous move, while met with success, had a devastating effect.

Brute-forcing the gargantuan dildo into his rump caused his heart to skip a beat. It wasn’t painful, per se, but the unmitigated intensity of it left him breathless. Craning his neck downward, his eyes widened in disbelief. In one fell swoop, he’d managed to bury half of the dong in himself.

The sound of a whimper snapped him from his amazed stupor, drawing his attention to the television. On the screen, displayed from two different angles, he stood in his bathroom and bucked back against the dildo in his shower. Sweat and water glistened on his immaculate hide, accentuating his godly physique. Truly, if there was one being which never failed to entrance him, it was himself.

Resting his hands on his head, as a number of twinks had done while they’d ridden him, he started to move. Flexing his legs, raising himself from the floor, he unsheathed himself from a few inches of toy, breathed, and lowered himself. The affair was a laborious one - not because of his balance or of how abjectly stuffed he was, but because it felt heavenly.

The same awe inspiring and exotic sensations from his trials less than twelve hours ago were magnified several times over. Keeping his eyes glued on the screen, seeing just how much he had enjoyed screwing himself in the bathroom, his nostrils flared. He tried to tell himself it was revolting, that he hadn’t taken amusement from it, but it was painfully obvious that hadn’t been the case.

Mesmerized by the sight of himself, continually moving up and down the formidable length of faux dick beneath, he leaned back. The change in positioning, while slight, increased the pressure on his abused p-spot - however, unlike his first attempt at training, he accepted the extraordinary sensation and didn’t slow in the slightest. Depressing his hips, sending yet more of the silicone shaft into his depths, the speed and power of his movements went unhindered.

With one particularly vehement plunge, the dong’s medial ring sank into his satiny interior. The detonation of pleasure which hit him sparked something, shaking the very foundation of his being and causing him to move even faster than before. Fiercely pumping his waist, working the toy like some wanton neophyte, he balanced himself on one hand.

Pawing at his chest, enthusiastically tugging at one nipple, he couldn’t look away from the television. Past his bucking hips and madly flopping cock, he was transfixed by what he saw. It didn’t matter that his stallionhood was slinging pre-cum over the carpet and his exquisitely defined abs, he simply needed more. He could stop any time he liked, simply get up and leave the pathetic dildo alone, but he didn’t want to.

He was the architect of his fate, the King of himself and anyone he saw fit, and this was all part of his grand design. If he took some small sliver of joy from elevating his prowess, so be it. Unleashing his full might, working his body like the angelic machine it was, the muscles about his frame were a symphony of movement.

Throughout it all, one fanciful thought persisted. He imagined that he was the stallion being serviced. Perhaps whispering hushed words of encouragement, tenderly stroking his bosom, or lavishing him with praise. He was the apex of lovers and, although he’d never considered it before, the notion of pleasuring himself in such a way drove him absolutely wild.

Breathing heavily, with his reservations crumbling under the ceaseless tide of bliss, he succumbed. Throwing his head back, his fanged maw flew open and he howled to the heavens. Shot after shot of roiling foal-batter flowed from his mighty stallionhood, like some ancient geyser, spattering him from head to toe. His limbs shook, in a fit of ecstasy, leaving him to crash to the floor and fully hilt the toy.

Crumpling to the carpet, in a murky state of consciousness, his mind struggled to comprehend what he’d done. He could feel the heat of his essence dotting his face, pecs, and abdomen, leaving him to assume the carpet in the surrounding area was thoroughly coated in the virile substance. His pucker feebly twitched, hungrily seizing upon the toy he’d sheathed himself upon, but that was a trivial concern.

There was one thing he clung to, one undeniable fact which shone through and eclipsed all others - he’d done it. He’d managed to handle something vastly greater than the tool Tack wielded. He would need to clean himself and his apartment, of course, yet those were minor details which would be dealt with shortly. So long as he devoutly committed to his practice, sharpening his skills with the monstrous dildo, he knew he’d be triumphant. Savoring his victory, heedless of his clandestine appetite for pleasuring himself in such a fashion, he rested and mused on how he would next sate himself…

Chapter 3

Sitting on his couch, leaned forward with his elbows resting on his knees, Sombra steepled his fingers and kept his crimson gaze fixed firmly on the door. On any other night off he’d be relaxing, socializing, or indulging himself with one of his many devout fans made lovers, yet this was a special occasion. It had been two weeks to the day since his inauspicious encounter with Tack and, true to his word, he was ready to settle the score.

Goaded by pride and the promise of subjugating the lad, he’d bottomed for the twink and lost in spectacular fashion. Humiliated, filled with the young stallion’s seed, and having been brought to climax purely by having his impeccable rump wantonly plowed, he’d been forced to dramatic measures. Offering double or nothing odds, promising to entertain at the Princely Pole while wearing slatternly marish outfits for two concurrent Friday evenings, if he lost, a pact had been forged.

The prior two weeks had been utterly grueling. Ceaselessly practicing his bottoming techniques, screwing himself in all manner of compromising positions, his backside had been well and thoroughly put through its paces. His onyx pucker, nestled firmly between his muscular glutes, could now easily accommodate even the most colossal stallionhood.

Though arduous at first, the routine he’d adopted had been a total and resounding success. He’d trained physically, studied on how best to pleasure a top, and more than acquainted himself with the feeling of being fucked. He couldn’t fathom being more ready, yet his self discipline hadn’t gone without leaving a mark.

Imaginings and daydreams of studs would creep into his thoughts, often inspiring him to practice with his toys at odd or inconvenient hours. Beyond the mental torment, his body had been left unmarred - well, almost. His once taut tail hole had developed noticeably, becoming more pronounced and pliable with the regular use; it didn’t bother him much, if at all, reminding him that he was just one step closer to physical perfection.

Knock Knock Knock-Knock Knock

The sudden sound caused him to blink, abruptly shaking him from his ruminations. Without moving a muscle, he glanced over at the clock atop his entertainment center - eight pm, right on time. Heaving himself up, flexing his back, he leisurely walked over to his door. As he undid the lock and reached for the knob, he took a breath.

Pulling open the door, he peered down at the slender grey stallion. Roughly half his size, with a relatively slim build, the pony didn’t look like anything impressive, yet Sombra knew better. The vile incubus had bested him, permanently tarnished his faultless carnal record and wounded his pride. Smiling at the lad, cleverly concealing any scorn he held for the twink, Sombra stepped aside and bid his guest enter.

“Looking sexy as ever, I see,” Tack warmly greeted, wiping off his shoes and stepping into the colossus’ apartment.

“As always,” Sombra began, locking the door behind the lad and giving them the privacy they’d be needing. “I trust you’ve been well?” he inquired, turning to appraise his visitor.

“Oh yeah, totally. How about yourself?” the twink countered, smiling up at his host.

“Well enough,” the King murmured, fixating on what lie strapped to the stallion’s back. There was nothing extraordinary about the book-bag the pony bore, although he definitely recognized it; his suitor had brought him a lustful parody of a french maid outfit to wear in the accursed sack, when they’d last met, so he couldn’t help but wonder what horrors it currently held. “Let me guess,” he flatly stated, leveling a finger at the piece of luggage, “sling bikini? Sexy nurse?”

Tack chuckled, shrugging the bag off his shoulders and unzipping one side. After thrusting his hand into the sack and feeling around for a moment, he produced what looked like a shoe-box. The thing was taped shut, with shipping labels over one side, yet there was no clear sign of what it contained. Holding it out to his host, he smiled.

“These just arrived yesterday. I’m gonna be honest, I was sweating bullets that they wouldn’t get here in time,” he explained, as the gargantuan unicorn daintily plucked the parcel from his hands. “I...if you want me to spoil it, I will, but I figured you may like the surprise. I know you’ll look amazing in it.”

“My dear,” Sombra sighed, hooking a finger under his guest’s chin, “someone would have to try to make me look bad in anything.”

The lad blushed and fidgeted, doubtlessly smitten with his sonorous tone and commanding presence. Sombra couldn’t help but smirk, more sure than ever that he would thoroughly despoil the little pony and leave him ruined for any future lovers. With the brief pleasantries over, and the small package in his hand, he turned and strutted off to the bathroom.

“Feel free to make yourself comfortable,” he intoned, slowing as he crossed the living room towards the lavatory. “And feel free to strip for me, I’m more than eager to have you,” he added, closing the door behind himself and disappearing from view.

Leaving his guest to entertain himself, he ran a polished fingernail along the box’s top seam. He couldn’t care less what he would be wearing when he subdued his lithe foe, so he pulled back the cardboard and peered inside. A sea of pastel hues met his eyes, as he gazed at the wardrobe he’d been given.

Digging into the package, the first thing Sombra discovered was a rather whorish school girl’s outfit. Folded within a cellophane package, with an image of the getup on the exterior, it looked positively debauched. An extraordinarily short skirt and a matching top, each a pale pink with white accents, were the main part of his getup. Digging deeper, he discovered the rest of his attire.

A pair of striped turquoise panties rested beneath the ensemble. Though they were clearly modeled after a mare’s underwear, the tag clearly displayed that they were meant for stallions. Big Bottom Bitches lay emblazoned on the waist band, above a rather generous banana hammock of material in the front of the garment. Noting the spare room, unlike with the maid outfit he’d worn prior, he realized he may be able to fit his enormous package in the area.

Fishing the second piece of clothing from the box, something rattled against the cardboard. Peeking within, he discovered a rather sizable teal cock ring resting at the bottom of the parcel. Hooking his finger on the item, bringing it to eye level, he appraised it. At a glance, it appeared as though it would fit on his girthy length, although he wouldn’t be completely certain until he tried it on.

Opening the packaged outfit, as well as removing the tag from the undergarment, he arranged the attire on the rim of his sink and began to disrobe. Folding his shirt, slacks, and boxers, he set his clothing on the towel rack and began to dress in the depraved uniform he’d been gifted. Everything fit him like a glove, as he’d expected, if only barely. After slipping the cock ring down his stallionhood, seating it against his sheath, he pulled up his panties and gazed at his reflection.

As silly as it sounded, he had to admit, he did look rather fetching in the outfit. The top, which happened to have a large bow directly over his breast, clung tightly to his torso, while the waistband of the skirt pinched into his waist. Being cut ludicrously short, the lower garment gave a teasing view of the obscenely bulged panties containing his package. All in all, he could easily be mistaken for some desperate tramp or street walker, yet he felt a peculiar thrill at seeing himself adorned in such a fashion.

Like some deviant warrior, he was ready for the impending erotic contest. The licentious ensemble was his armor - his unparalleled physique, his arsenal - and his unshakable resolve, his bulwark. He was ready, nearly a month had led to this moment, and he would soon mend his wounded pride. Sauntering out of the bathroom, sensually swaying his hips from side to side, his ego was a roaring inferno.

As instructed, Tack had stripped down and was sitting on his sofa. The slate colored stallion’s eyes widened, as he watched the adonic King drawing nearer. The lad’s tool, resting between his legs, twitched at the sight of him. Without breaking stride, Sombra walked to his guest and squatted down to the floor.

Splaying his legs wide and arched his back, he gave a sublime view of his scarcely concealed nethers the seated twink. Though he was fully aware that he must have looked like some degenerate, it was part of his plan. Getting his prey worked up would be the first step to achieve his victory.

“Enjoying the view,” Sombra purred, fondling himself while balancing on one arm.

Tack’s mouth flapped for a moment, before he nodded enthusiastically. Reaching for his groin, grabbing his hardening member, he started stroking himself like a randy school colt. The giant unicorn before him smiled and launched himself forward. As his legs were tenderly pried apart by his mountainous host, he gulped.

Even though Sombra had trained his ass to the utmost, he wasn’t above giving himself a slight handicap. Grabbing the lad’s wrist, pulling his hand away from his rigid stallionhood, he leaned in and breathed hotly upon the throbbing length of flesh. Gazing into the lad’s golden eyes, without the slightest bit of hesitation, he wrapped his lips around Tack’s cock.

Sombra didn’t consider it cheating, per se, since oral was almost always the opening act before someone got fucked. Contentedly humming around the tool, he watched his rival’s face contort in pleasure. Resting one arm on his knee, maintaining a deep squat, his free hand reached down between his thighs. Pulling the panties aside, he kneaded his backdoor.

He’d thoroughly cleaned and lubed himself less than an hour ago, yet getting himself a little warmed up wouldn’t hurt a thing. He certainly wasn’t getting excited about having the hot, wonderfully hard shaft in his muzzle - no, he was just ready to assert his superiority over the cur. Slipping two fingers into himself, he slathered his guest’s dick with saliva.

Bobbing his head, breathing in the smaller stallion’s surprisingly heady musk, his nose repeatedly bumped against the twink’s groin. As his digits caressed his well-worked p-spot, he closed his eyes. He almost felt bad for what he was about to do - not for himself, but because the svelte pony would never again get a piece of tail better than him.

“Gods,” Tack groaned, lightly bucking against the titan’s snout, “you really are amazing in every way.”

The compliment, paired with the first salty taste of pre-cum on his taste buds, caused Sombra to withdraw his head. Drawing his tongue up the sensitive underside of his lover’s length, giving it a parting lick, he stood to his full height and swung one knee onto the sofa. Grabbing the back of the couch, to either side of Tack’s head, he straddled the stallion and got into position. It was time for the true contest to begin.

Given his rather extensive practice, he’d become quite proficient with impaling himself on something by feel alone. Lifting his tail and swinging it to the side, he lowered his waist. His aim was perfect, allowing his tush to effortlessly transfix himself on the first attempt. Tack gasped, doubtlessly overwhelmed by the warmth and snugness his flawless body afforded.

“Tell me,” he began, peering down at the lad, “how amazing is it?”

“S...so good,” Tack murmured, burying his face against the Sombra’s midriff.

Their difference in size was rather striking, with the King utterly dwarfing his paramour. Riding his guest in a seated cowgirl position, Tack’s head only reached Sombra’s solar plexus. The lad’s small stature didn’t bother him in the slightest - in fact, he found it rather cute. The disparity of their scale was, after all, a rather fitting exhibit of their inequity of grandeur.

Merrily wiggling his rear, which rested heavily upon the lad’s lap, Sombra began to bounce. Using the furniture to stabilize himself, he steadily raised and lowered his waist. Beyond moving his monstrous frame, he clamped his pucker on the upward movements and relaxed on the descents. The angle spared his prostate from much stimulation, although the stallionhood plunging into him was just enough to tickle the delicate organ.

Reaching upward, Tack deftly unfastened the button securing Sombra’s top over his chest. The article swung open, gloriously displaying his obsidian hide and perfectly sculpted pecs. Having giving himself a better view of the King’s bare flesh, the twink grabbed the unicorn’s waist and began bucking his hips.

Sombra had to admire the lad’s tenacity, boldly remaining defiant in the face of a demigod. He chuckled, synchronizing their movements and savoring the pleasurable havoc he doubtlessly wreaked on his guest. Just as he’d found his rhythm, the little earth pony hit him with a surprise move.

Pressing his feet to the floor and sliding his behind forward, Tack altered the angle of his thrusts. The change caught Sombra off guard, increasing the pressure on his weak point and sending a shockwave of euphoria surging through him. Staring down in surprise, just as the lad’s lips wrapped around one of his nipples, he bit his lip.

While the dimensions of the twink’s tool weren’t the problem, especially since he could accommodate something more than double the lad’s size, he found himself wracked with unforeseen pleasure. Besieged by sensations he’d had no earthly way to prepare himself for, he did what little he could to cope. Sadly, it was all infuriatingly compelling.

The heat of Tack’s body, his lilting praise, how his hands wandered, the way his lips suckled, they were like a debased feast for the senses. In spite of all his training, dealing a cacophonous blow to his arrogance, he found his resolve wilting. His body paid his railing mind little heed, bending to the small stallion’s will.

Rocking his ass back and forth, trying his damnedest to figure out if he was doing it to push Tack to his limit or to sate himself, his movements hastened. His gigantic stallionhood excitedly swelled, sneaking past his panties and skirt to sandwich itself between him and his partners’ torsos. Growing faster with every moment, stimulated by their moving bodies, the glistening, pre-cum slickened head wormed up to his chest.

Peering down, watching his mate kiss and nibble his teat, he spied the tip of his length trapped between his prodigious pecs. From his vantage, it almost looked like he was giving himself a tit job. As jarring as the concept was, it paled in comparison to how maddeningly wondrous it felt. Try as he might, he couldn’t cease his perfidious body from indulging.

Virtually every part of him was worshipped in some form or fashion, from his formidable cock to the depths of his ass. The only experience he’d had like it was on his first encounter with Tack, although this was far worse. Either his exercise and study had been for nought or he’d made a woeful miscalculation about choosing the position. It wasn’t until his lover bit down on his nipple, eliciting an effeminate squeal from delight to pass his lips, did he regain some semblance of control.

“P...perhaps a change of change of a...arrangements are in order,” Sombra sputtered, only barely maintaining his composure.

Mercifully, Tack’s thrusting drew to a halt and the lad looked up at him. Reclining fully, releasing his grip on the King’s lower back and tush, he nonchalantly took to stroking Sombra’s stallionhood. “What’ve you got in mind?” he cheerily inquired, fixating on the sensitive underside of his paramour’s glans.

“The bed,” Sombra immediately replied, wanting little more than to flee.

“Of course, my Master,” Tack humbly intoned, curtly bowing his head forward. Dragging his tongue over the blunted tip of unicorn cock before him, he honored his King.

Sombra was only just able to stifle a whimper, as he laboriously pushed himself up and unseated himself from the lad. With as much grace as he could muster, he strolled around the sofa and towards his mattress. Since he hadn’t planned on being rutted in more than one position, he was left to improvise.

Placing one knee on the bed, he crawled onto the padded surface and eased himself onto his stomach. Lying prone, with his legs parted slightly, his length came to rest between his thighs. Though there’d be nothing stopping Tack from battering his behind from above, at least his chest and stallionhood would be left largely unmolested. Grabbing a pillow and dragging it under his head, he invitingly waggled his backside.

It was a precarious situation, to say the least. He was far from throwing in the towel, yet his limits were already being tested. With his confidence shaken, he reached back and prized his glutes apart. There was no way he could afford to lose a second time - not only because of his reservations about parading around in marish garments on stage, but because his dignity wouldn’t allow him to do otherwise.

“You know,” Tack purred, growing nearer, “I’m a little jealous.”

The statement caught Sombra by surprise, causing him to look back at the stallion. “Of what?”

“Of not being the first to top you. Sweet stars above, I wish I could claim that title,” the lad admitted, scaling the bed and moving between the King’s legs. “Whoever was the first stallion to claim you,” he whispered, drawing one hand up the unicorn’s calf, over his muscular thigh, and to his presented tush, “must have been the luckiest pony ever…”

Sombra’s heart skipped a beat, hearing the twink’s words. The adulation was, in a word, exquisite. If Tack had known the truth, that he was the stallion to despoil his behind, he’d surely be elated beyond belief - still, he couldn’t concede that bit of information. While possibly pushing his lover closer to the edge, divulging that the twink had tainted him in such a way could just as easily backfire.

“You’re just so...perfect,” Tack continued, bringing his face the colossus’ ripe, heavy balls and grandly displayed stallionhood. “Every part of you is divine and I’m honored that you would allow me such a privilege,” he reverently muttered, breathing in Sombra’s scent. Continuing to move on his hands and knees, passing over his immense lover, he brought his rigid length to the unicorn’s behind.

As Sombra was mounted from above, he released his buns and steeled himself. Sure enough, as Tack got into position, he felt the hot length of cock brought to his loosened entrance. Pawing at the bedsheets, with his eyelids fluttering, the twink slowly and sensually sank into his ass. His small paramour’s tool was left sheathed in his rump, allowing him to savor the heavenly heat and fullness.

Draping his face over the King’s mountainous shoulder, Tack began bucking away. Angling his thrusts like a professional, making sure to grind his medial ring against Sombra’s prostate, he satiated both himself and his partner. It was not unlike a tale of David and Goliath; while the size and build of the two were worlds apart, the smaller stallion was clearly a force to be reckoned with.

Gnawing upon one thumb, rhythmically raising his waist to meet the lad’s plunges, Sombra was awash in bliss. Although it was true that parts of him were spared rapturous harassment from his mate, it was impossible to deny that his willpower was waning. He had next to no freedom of movement, he was being loving rutted, and he was slowly going mad with lust.

“No,” Tack lovingly tutted, reaching up and gingerly seizing his wrist.

Sombra’s hand was pulled away from his face, leaving him with nothing to stifle himself. He could have overpowered the stallion a dozen - no, a hundred times over, yet his strength was all but gone. Confused, frightened, and profoundly aroused, he acquiesced to his lover. Peering back at the lad, a hushed whimper crept past his lips.

“There we go,” Tack cooed, looking fondly down at the Adonis. “Let me hear that beautiful voice of yours…”

WIthout skipping a beat, his mate forcefully plunged into Sombra and struck a direct blow against his p-spot. Almost on instinct, his eyes closed and a throaty, marish groan of delight cut through through the air. He could barely comprehend that he’d made the noise, before his guest started brutally pistoning his ass.

“So wonderful, so divine, I’ll remember this for the rest of my days,” Tack huffed, his hips becoming a blur. “I hope you’ll remember me too.”

“Y...yes,” Sombra bleated, albeit hesitantly. Throwing his ass back, ensuring their bodies slammed together, he did what he could to please his guest.

Casting his arms wide, Tack’s hands wormed around the King’s giant chest. As he continued to pound into his host, moving harder and faster with each passing moment, he found what he was looking for. His fingers seized upon the unicorn’s teats, firmly twisting the buds of flesh.

A piercing howl cut through the air, as Sombra’s voice raised an octave. It was impossible to think, as his existence was consumed by his primal and carnal needs. Clenching and relaxing his pucker, holding onto the bedspread for dear life, his limits were tested beyond reasoning. Pre-cum dribbled and weakly gushed from his shaft, smearing the sheets as his stallionhood began to flare.

He wasn’t going to be able to hold out for very long - then again, neither was his pint-sized paramour. Tack’s movements were becoming frantic, losing their steady rhythm and devolving into wild, nearly panicked bucking. It was coming down to the wire, they were neck and neck, and he honestly couldn’t tell which would outlast the other.

Stricken by divine inspiration, acting on impulse, Sombra threw his head back and brayed to the heavens. “Breed me!”

His desperate plea was the finishing blow for Tack. Hilting, crying out, he bathed the giant’s interior with his essence. Fitfully bucking his hips, huffing and grunting above his lover, he pumped his seed deep into the King’s depths.

Sombra’s breath caught in his throat, his heart thundered in his chest, and every muscle about his body seemed to tense. In a singular moment, feeling the heat and pressure of the lad’s cum flooding into his deepest depths, marking parts of him that no other ever had, time slowed. The stars aligned, the heavens parted, and he came with all the force of a collapsing star.

All his senses went into overdrive, flooding his mind with every conceivable form of pleasure he could imagine. Spunk cascaded from his stallionhood, seeping into his blanket and spattering over the edge of the bed. His pucker hungrily clenched and milked the cock inside of him, as if yearning for every drop of the lad’s rich cream. It was at that moment that an epiphany struck him, as his body lay in the throes of rapture.

Why couldn’t he relish all aspects of being a sexual tyrant? The words top and bottom were just that, words; neither inherently conveyed any sense of control or or supremacy. Just because one was being rutted didn’t mean they couldn’t be the one dominating their partner! The light of truth shone through his ecstasy, as his consciousness teetered on the brink.

Tack’s weight bore down upon him, as the lad lie atop his back. Sombra breathed, grappling to comprehend everything that had happened. He truly couldn’t say if he’d won or not, having climaxed at practically the same time as his guest; it was, in a very real sense, a photo finish. Shakily reaching back, cradling the twink’s ass and holding him in place, he rolled onto his side.

“H...holy hell, that was even better than last time,” Tack rasped, gleefully spooning with his oversized paramour.

Sombra nodded and hummed, unsure of what to say. Even if he had definitely won their little competition, he was no longer concerned. As strange as it may have sounded, the climax of their endeavor had been cathartic. He was at peace, with his own foolish preconceptions of bedroom preferences vanquished.

The stallion against his back wiggled about contentedly, lovingly stroking and kissing his neck. “Too bad that I lost, I was really hoping to-”

“How much were the outfits?” Sombra interrupted, his lilting voice quieting the lad. With the clarity he’d achieved, his commanding presence had returned forthright.

“They weren’t much, maybe fifty bits for each, why?” Tack countered, craning his neck to look at the unicorn’s face.

“I’ll compensate you for them. After all, given their somewhat used state, I doubt you’d be allowed to get a refund,” the King intoned, smiling to himself. “We’ll consider the matter a draw. Don’t worry about me destroying your ass, for now.”

Propping himself up on one arm, as his softening length slipped from his host’s rump, Tack beamed. “So you’ll wear one?”

“Mayhaps,” Sombra lovingly growled, rolling over to face the lad, “on one condition…”

Tack’s pupils dilated and he shrank back, faced with the fanged maw the monster before him. “W...what c...c...condition?”

Leaning in, smiling ominously at the lad, Sombra’s eyes went alight with carmine light. “That we aren’t finished until we’re both limping into the bathroom…”

Epilogue

“Shake it, you magnificent bastard!!!” some nameless voice raucously yelled over the din of the crowd.

Hooking his leg around the chrome pole in the center of the raised dias, Sombra leaned back, extended one arm, and spun around the polished shaft. The snow white pleated skirt fluttered about his waist, giving the throng fleeting glimpses of his alabaster panties. Emblazoned with a scarlet cross, similar to the extraordinarily snug and shortly cropped top he wore, his outfit was nothing less than an obscene parody of a slutty nurse.

His piercing gaze swept over the crowd, as he halted himself at the center of the platform. Twirling around, he took a broad stance and brazenly presented his rear. Sinking to the ground, in the crimson toe-less heels on his feet, his obsidian cheeks peeked from beneath the sheer petticoat around his waist.

The hoard went ballistic, whooping and hollering like mad. Beneath his surgical mask, he smirked to himself. As he leaned one shoulder to the pole, he looked back at his adoring fans. Stallions of all shapes and sizes, as well as a handful of mares, watched his performance in awe. Yes, making the decision to flaunt himself in feminine garb had definitely been a wonderful idea.

After his apocryphal second encounter with Tack, his eyes had been opened. His problem hadn’t been with bottoming - no, it had been his misinformed and ignorant concept of the matter. He’d wrongfully assumed that any stallion who was being fucked was submissive, bending to the top’s will and prowess, but he couldn’t have been more wrong.

Taking a dick in the ass didn’t mean he was beneath anyone, metaphorically speaking - if anything, it allowed him to have even more control in carnal affairs. Any stallion could wantonly buck their hips and sink their length into someone, only a true sexual god could force another to submit with their backside and zeal.

His second bottoming experience was followed less than a week later by a third, then a fourth and fifth, until he’d triumphed over half a dozen stallions. Something about riding them, or bucking his backside against them and making them pop, was supremely gratifying. He still got off, of course, but only at the very last minute.

As time passed and his skill grew, he relished such experiences with increasing intensity. He still topped quite frequently, rutting svelte partners into oblivion and oftentimes giving them more than they’ve ever had, yet he’d opened himself to a whole new world of experiences. If anything, his newfound tastes had brought him one step closer to divinity and perfection incarnate.

Surveying the multitude of ponies, as well as the small number of other creatures present, his eyes settled upon a particularly brutish changeling. Nearly a head taller than everyone else present, with a jagged horn atop his head, the muscular bug-horse noticed his attention and blushed.

Sombra’s mouth began to water, and his pucker hungrily clenched within his thin undergarment, as he shot the stag a wink. His show was almost concluded, the stage was littered in bits, and he was covered in sweat. He had little doubt that he’d be able to find the stud after his exhibition, so long as the shapeshifter didn’t abruptly leave.

Yes, perhaps he would treat the changeling to an exclusive show, one which he reserved for those who caught his baleful eye. Those chosen few who found his favor were forever changed, usually begging for more time or repeated engagements. Whether or not the hulking stallion was a top or a bottom was of little consequence - either way, he’d be sure to give the devotee an experience of a lifetime…