Filthy Rich watched as nightfall blanketed the garish cityscape of Las Pegasus from the half-open curtain of his Sunrise Inn hotel room, the soft-yellow radiance of the budget suite's obnoxious neon sign bathing the darkening parking lot below in a facsimile of morning light. Yet, the grinning sun welcoming guests to the establishment could never hold a candle (in both the witticism and candlepower sense) to the radiance that Las Pegasus showcased when day faded into night. Rich stood spellbound at the window, waiting for that artificial sun to spark alight.

Gradually, stars in the night sky twinkled out as their earthbound counterparts erupted into life; first the spotlights of the forebodingly-shaped Prism resort reflected off its glossy exterior, followed immediately by the sparkling illumination of its arch-rival, Morpheus. Treasure Island glittered against the darkness like a chest overflowing with pirate doubloons, making it the business-savvy earth pony's clear favorite; though Rich held a love-hate relationship with the casino following his last less-than-profitable visit. One by one, the City of Sin's centerpieces awakened in their shared glow, a sight the country-born stallion always found overpowering, beautiful as any sunset even.

"Celestia's sun might be the brightest light out there; but Las Pegasus sure gives her a run for her money. Hah, surprised Luna doesn't sue; this city eclipses her moon most nights," Rich mused with a tired smile, winding down a day fraught with business conferences centered around brokering deals for the newest branch of his Barnyard Bargain's department store.

Granted, he'd been lucky enough to attend a stage show at Treasure Island as a free interlude during lunch, but the entertainment spectacle became an awfully tense distraction for the mature stallion. Rows of slender, handsome and athletic college-age colts, dressed up in pirate garb and gyrating across a ship-shaped stage in harmonious thrusts...It took all the earth pony's willpower to keep his attention focused on his blathering assistant rather than the rising part of his anatomy pressing up against the underside of the table! If only he'd borrowed Diamond Tiara's camera for the trip; he'd have saved every moment of that showcase, under the pretense of showing his family what they were missing! At least, perhaps, it gave him a reason to return to Treasure Island someday...

For now, the frustrated stallion sought to dull the ache of the day's grind with the distant sights, the remains of his room service, and a few shots of Appleloosian Standard whiskey to keep him company. Though, with the slightest bit of fortune, he'd not have long to linger in solitude this evening.

The stallion sipped at his whiskey mixed with soda, the bubbles feeling ticklish against his scruffy lip, Rich having forgotten to shave that morning. His oiled jet-black mane wore the frazzles of travel, but he'd grown to like seeing it slightly wild; it reminded him of younger, more daring days, before the weight of adult obligations, a successful business, and the unexpected surprise of a filly entering his life tamed those cravings. Tamed, however, did not mean terminated; far from it, actually. Things corralled had a habit of riding free, once the gate of responsibility was left unlatched... Where better to pry open that gate than Las Pegasus?

Before another sip reached his lips, Filthy Rich's cell phone flared to life on a nearby coffee table, a satisfying cash-register chime marking the arrival of an email into one of his many inboxes. The earth pony hastily departed the windowsill, grasping his phone and swiping through his email accounts with an anxious tremble; his personal account stood bare, and his business one, while overstuffed with quarries and offers from suppliers, could wait. A red "1" hovered over a third account, one kept a secret from his associates,, friends, and especially his wife.

The account header read "MarriedMustang45," a name that still made Rich chuckle from how silly it read in his head, but one that got his intentions across to anypony glancing at the ad he'd placed online right after that incredibly distracting pirate dance show:

"In town on business, wanna strike it rich? 40+ year old earth pony stud looking to host a colt for some fun while I'm away from home. Younger guys on the slender side who can follow orders are a plus. Ponies only please, but I don't care if claim that you've got the wings of an angel, a horn that's hard as I am, or know what to do with your hooves; reply with pics and be ready to meet in my hotel room. If I like what I see, I'll text you back my place and room number. I'm a busy stallion with little time to play, so let's keep things simple, sane, and DISCREET."

Rich's gaze lingered on the new email, its title simply reading "Still looking for company, Mustang???" and containing a trio of attachments. Lifting the whiskey back to his muzzle, Filthy downed the rest of his glass, leaving the booze-laced ice cubes hovering in the puddling remnants. Opening the message, Rich's old cravings made themselves readily apparent, the surprise awaiting inside stirring the stallion's loins into attentiveness, his dark blue eyes transfixed on a single line of text:

"Just got off work and I'm ready to play; still looking for a hookup tonight, Daddy?"

A line like that alone fed Rich's fantasies for days, even more so than seeing his wife in her high-priced lingerie the night before he'd left Ponyville, but the three attachments sold it better than most deals the stallion ever hoped to make. All were photographs freshly snapped with a smartphone camera; the first showed a smiling blue-furred muzzle snaking a tongue suggestively around the tip of one of those sweet starfish-shaped lollipops from Treasure Island's gift shop, lapping at the point of the star in a suggestive fashion.

The second captured a full-body shot of a lean pegasus stud, whose face was wreathed by his wings to preserve anonymity, the stud's fluffy chest-fur poking out from underneath the unbuttoned jacket of familiar, gaudy pirate costume. Was it one of the sorts they'd sold at the gift shop, or even better, the genuine article?

The final, and most explicit snapshot, nearly stole the breath from Rich's pattering chest; the rear of the pegasus' costume was pulled down to his ankles, presenting the swell of two weighty dark-blue testicles and an unclothed sheath, the very faintest trace of hardness beginning to take shape and lend it a slight firmness.

Filthy's eyebrow twitched, the entrepreneur's lower lip feeling the light press of his teeth. Old cravings awakened anew, stronger than he'd last recalled them, their grasp shuddering across his hardening, hungry stallionhood. In a few clicks and swipes across the screen, Rich saved the three photos into a password-protected stash named "Closed Deals," and began typing a reply with one hoof...the other was far too occupied fawning along the underside of his ebony shaft.

"You've got just what Daddy's been missing. Sunrise Suites, Room 244. Wear that same costume you seem to like prancing around in. The door will be open for you." Rich tapped out onto the screen, patting the "Send" key and pouring himself another fizzy mixed drink. Half the glass sat empty in the minutes leading up to the pegasus' reply, Rich's phone chime almost making him jump.

"I'll be flying over ASAP. Give me ten minutes, Sir," Rich read. The capitalization spoke volumes, harkening back to a time when every stud he'd wanted called him that. "Sir." Too many forgot the authority such a title implied, but this young colt hadn't.

"Don't keep me waiting flyboy, I can't wait to see you up close without those wings in the way. The stage doesn't do your body justice, but I will." Rich's reply vowed, the stallion's workaholic persona giving way to one who traveled the rougher roads of Equestria in his youth, leaving broken hearts and satisfied colts in his wake. His lucky visitor would get to see and feel that return to form personally soon enough, but the ten minutes seemed to pass like one of the rare slow days at Barnyard Bargains.

Rich's mind wandered to the family of cheer vacationers staying in the next room over, a husband and wife and their children, all of whom wore the trappings of tourists; cameras, oversized-sunhats, and the more "family friendly" city guide pamphlets that steered clear of the dens of debauchery. They reminded him of his own family back in Ponyville, and how he sat on the verge of betraying their trust for selfish pleasures...or, where they really all that selfish? Years of faithfulness, financial stability, and a pleasant-if-unexciting married sex life; wouldn't it be more healthy to satisfy these urges now, when it couldn't hurt anypony, than keep them bottled up?

The second drink passed down his throat quicker than he'd expected, so Rich poured himself a third shot, leaving the amber-filled bottle flanked by a few cans and the ice bucket on the coffee table. A cartoon sun smiled back at him on the bucket, the edges of its rays fuzzy from the whiskey's influence; but the blurred outlines of his vision brought Rich comfort, a reminder of dingy side-road dives and the soft-furred colts lined up inside them, all easy pickings for a mysterious sweet-talker with a greased jet-black mane and rugged leather jacket.

How many of those giddy broncos had he broken in behind the bar, or left a satisfied mess in a roadside bathroom stall?

Most of them probably shaped up to be a lot like him once they'd grown out of those "wandering years" on the road; family stallions with loving wives and foals, working for every bit they earned. Rich wondered if they ever thought back to him; if they'd spent time alone in the shower remembering how he'd felt behind them, what sort of pleas that dark-haired earth pony stranger made them scream underneath the rock of his stout hips. Celestia knew, his hardening cock certainly couldn't stop thinking about every single one them, at least those whose faces and moans stuck out. Rich left behind quite a trail of walls scraped with hoof-marks down the highways for them to follow.

Maybe he'd take a trip that way again, see if he still had that suave spark? That, or start a new trail in hotel rooms, far from home...

A gentle knock at the door roused the earth pony from his fantasies of old escapades, as he stood on the brink of turning them into reality once again.

"Come inside, lock it behind you, and stand in front of me." Filthy bellowed, not bothering to approach the door or cover himself up for modesty's sake. Why hide nature's ideal tool for attracting loose studs towards him for the breaking-in they needed?

"Yes, S-Sir," came the effeminate reply, hesitant to enter, yet excited for what he might discover inside. The door swung open and shut just as briskly with the clink of the lock turning, revealing a beautiful stallion, one whose angelic countenance alone almost made the decade-long gap between same-sex interludes worth the wait for Filthy.

The grainy, low-resolution photos sent in the email did his intrepid young guest a stark disservice, as they'd failed to showcase not only the limber curves of the pegasus' trim figure, but also the softness of his gentle, alluring violet eyes. The stud's periwinkle-blue fur shined with carefully-groomed luster even in the distant lights of Las Pegasus, wearing a trace of sweat from the hasty flight over. Rich sized up his prize, guessing that the colt was in his early twenties, clearly less than half his own age. Was he even old enough to drink yet? That thought aroused him greatly, as he imagined leading the pegasus down a trail that started with a few drinks, and ended in ecstasy.

The pegasus stood slightly smaller than the earth pony in both stature and bulk, his figure that of a dancer's and clearly meant for all the motions demanded onstage; yet, its supple contours were accentuated, rather than hidden, by a snug-fitting pirate costume. Kept in place along his midsection by a dark-green sash, the white sleeves of the costume billowed out to allow ease of motion, nothing on the outfit risking an interuption of fast-moving hooves or flapping wings as part of an ensemble cast. A green tricorn hat sat upon the stallion's long, wavy, two-tone purple and white mane, decorated with a trio of colorful feathers from a variety of tropical birds.

"Ah, so I was right then; I remember you," Rich said coolly with a stroke of his scruffy chin, appraising the prancing pirate's enticing eyes with his own stern blue stare. The stud's tentative guest glanced down briefly, as if from nerves, but Filthy knew exactly where the colt's attentions were actually fixated; or rather, what they were interested in. The thought drew a twitch of appreciation from his weighty shaft, relishing his visitor's interest with a knowing growl. Times, tech, and fashions might change, but what colts wanted most always stayed the same."You know, I saw your show this afternoon, over lunch. Couldn't get my mind off it."

"Y-You were there?!" the limber pegasus yelped with a sharp whinny, one wing flicking so abruptly that he very nearly knocked the hat right off his own head. "I-I take it you really liked our Pirate Promenade song number then, Sir?"

"Oh, it was a fine show; but truth be told, it wasn't the music that kept me at enraptured to the point that I just about tipped the table over with this," Rich admitted with a suggestive sneer, his erection standing at full-mast as living proof of that lewd predicament earlier during lunch, of which this colt and his prancing coworkers shared some responsibility. The earth pony lifted his bottle, pouring his guest a fresh, cold glass of whiskey-and-pop to match his own. "First Mate High Tide, is that right? It's easy to remember a character with such a distinctive hat and a memorable sway to his hips. Your sky-dancing on the bow of the ship-stage in particular was quite...distracting."

"I'm happy you noticed! I-I really get invested into our routine sometimes, the music just works its way through me like a trance... But, if you think that performance was suggestive, you clearly haven't seen the late-night show on the weekends! We go all-out for that," the pegasus reported with a jittery chuckle, the pegasus cheeks adding the shade of a pink blush to his wardrobe as he approached the table, though perhaps with trouble walking with his own growing "mast" pressing up from underneath those seafarer clothes.

"You don't say? It's too bad I'm only here for a few busy days, I'd love to see it..." the earth pony remarked, making a mental note to snag a recording of the later performance online, certain he'd find a few more colts he'd like to meet onstage. "Then again, having the hottest star of the show all to myself for an entire night is more than most can say, so I'm happy regardless."

"V-Very true! I-I don't do this kind of thing very often, honestly," the colt confessed sheepishly, a statement made fact by his inability to stop chattering or gawking at Filthy Rich's brazenly-displayed stallionhood, its dark girth transfixing his gaze. If only his wife were so excited at the mere sight of his erection; Diamond probably wouldn't be an only child, if that were the case.

"High Tide is just a stage name though, I'm actually call-"

"Stop," Filthy interrupted, waving a hoof to command silence from the colt, who complied without protest. "No real names in this hotel room, "High Tide"; discretion is the name of the game, remember? As far as I care, you're a pretty pirate stud, and I'm the elder, wiser, and well-hung salty sea dog who you're going to serve without question tonight. Are we clear on that?"

"Uhm, yeah, crystal-clear Sir," the first mate nodded with an energized swish of his short-styled tail, recognizing who called the shots and packed the real heat in the room. Colts always fell in line when push came to shove, and Rich intended to do a whole lot of both to the cute pegasus before the night was done.

"That's "Daddy" to you, First Mate; after all, that's what you called me in your message, wasn't it?" Rich rumbled back, patting the empty space on the couch next to him with a expectant hoof, the other kneading the base of his rigid cock and pressing its length against the slightly rounded pudge of his stomach. "Why don't you dance your way right here on this deck and have a drink? I want to see those beautiful feathers of yours again, up close this time."

"Aye-aye, Daddy! You'll find I'm quite good at following any orders I'm given," High Tide chimed with feathered salute, flexing his wings and daintily hovering over to the designated perch next to his earth pony host. Timid at sitting so close to somepony so casually aroused, but no less turned on himself, the pegasus aimed to muffle his nerves with the offered alcoholic drink. Clutching the icy beverage with a wing, High Tide closed his eyes and leaned his head back, downing the hearty booze with a prolonged chug. Satisfied and sated, he set down the glass, fluttering those purple eyes open again. "Thanks! I really needed that to get in the-hah-Mmmphh!"

Seizing the initiative that was rightfully his to take, Rich's muzzle darted forward to shut the colt's own blathering mouth up with a passionate, rough kiss. The dark peach fuzz of his unshaven chin added a harsh friction to the earth pony's heated lusts, a remarked contrast to the freshly-brushed smoothness of his newest boy-toy's lustrous blue fluff. The sweet aftertaste of whiskey-and-pop roamed between their intertwining tongues, a familiar flavor that Filthy chased right into the surprised pegasus' yielding muzzle.

"Rrragghh, sorry for interrupting stud, but Daddy really needs this a whole lot more than you'd believe, mmphh..." Rich gnarled ravenously as he continued the sloppy kiss, High Tide's flicking wings grazing the earth pony's shoulders as they flapped on their own accord. Impatient and wanting to feel more of what his soon-to-be conquest had to offer, Rich used a firm hoof to root the fly-boy to the couch, while the other groped underneath his silken costume to free that tell-tale hardness pressing up uncomfortably against his trousers.

"Sir, what are you-Aahh?!" High Tide yelped sharply, a genuinely adorable cry letting Filthy know that he'd found his mark; not that he'd need to search for long, given how desperately his guest's maleness strained for liberty underneath the pegasus' trousers. The two stallions sat side-by-side, exploring each other eagerly once whatever tentative barriers between them vanished in the boozy kiss. Coaxing a colt into action really was like riding a bike; a skill not lost with age, and one which Filthy had no intention of ever forgetting his mastery.

"It's about time we both started brandishing our "cutlasses," stud. Graagh, that's it, show Daddy how riled up he gets you!" Rich demanded, breaking the hot kiss as his hoof tore away High's sash, freeing a dark-blue shaft splotched with a dab of white just along the pegasus' already-swelling tip.

Something about seeing a younger stallion turned on so much from just a wet kiss and some dirty talk aroused Rich to his core; as if at any moment he'd only need to turn his suave "salespony charms" honed at Barnyard Bargains towards enticing a few of the cuter clerks working his chain of stores, and he'd never want for some action in the secluded storerooms. It'd certainly make negotiations for raises much less repetitive, if he'd get his own "raise" in return. The idea was something to consider on his return home; for now, it was all about breaking in High Tide.

"Oh y-yes, I'm so hard for you, Daddy; I-I could barely fly straight all the way here, I was so riled up thinking about it!" the First Mate uttered, nuzzling the older stallion affectionately, enjoying the gentle scrape of his host's unshaven cheeks. Recovering from the kiss, the timid stallion's quivering hoof reached down towards Filthy's lap, tenderly stroking just below the head of the earth pony's rigid shaft. "H-Hah, guess nothing about me is "flying straight" tonight, right Sir?"

"Damn right," Rich agreed, returning the nuzzle with a suckling kiss across the colt's supple neck that was sure to leave a lingering mark under his fur, while the earth pony's hoof kept busy fondling the pegasus' warm testicles. "You're not done flying yet, First Mate. Hover onto Daddy's lap; it's about time these sabers of ours crossed."

"A-Aye, but I think it's kinda obvious just from looking whose got the bigger sword to play with," High Tide conceded his defeat in the "saber" size department with a giddy wink, grudgingly removing his fawning hooves from the earth pony's ebony stallionhood before jolting off the couch. The flight proved nothing more than a brief hop, and with a pause only to secure his feathered hat, the lithe pegasus found himself sitting square on his handsome host's accommodating lap. Try as he might, High's wings refused to fully close upon his back, the colt's twin heavenly features half-open and wreathing his smile. "This little eagle has landed, Sir! Much littler, actually; it's true what they say about earth ponies, huh?"

"Oh, it's all true. Sure you didn't fall overboard from an airship hovering up in heaven?" the earth pony prodded back, but not only with a cheesy pickup line; Rich's hooves firmly clutched the pegasus' developed hips, pressing the colt closer and lining up both their cocks into direct contact with each other. Dark blue and jet-black felt equally-hard against each other despite the size difference, Filthy's earlier stimulation leaving him already slick with precum, the earth pony's thickness and length outmatching that of his companion by several solid inches all around.

" Those feathers really suit you High; on the hat, and those ticklish fairy wings," Rich complimented before thrusting himself against High Tide's body with a grunt, the two stallions so close together than both of their throbbing cocks occupied the only space between them, their flared heads poking up against each of their chests; or in High's case, his stomach. Rich and High began panting in concert, their frotting shafts heated by mutual body warmth and sweat.

"Show me they're not just there to look pretty, put them to work for Daddy..."

"J-Just for you, Daddy," High Tide nodded, flexing his wings and putting those practiced dancer's hips to work, the pirate's gyrating motions resembling those of a slutty pole-dancer worshipping their client in a backroom show.

Rich knew more than one hunky pegasus with a few fancy wing-tricks under his belt; hell, he'd felt several pairs of particularly-talented wings around his dick over the years! Still, he'd be be hard-pressed to recall one so eager to earn his stud's approval, so desperate to grind out an appreciative shudder from the earth pony's dripping cock. The straddling pegasus' member leaked its own warm pre, smearing his excitement across the rubbing heads and swelling each of their flares to readiness, heat and perspiration gathering between the pair of horned-up stallions.

"I'm loving how much bigger you are, Daddy! Mmm, bigger than all the other dancers in the dressing room, and way thicker than my last c-coltfriend's cock," the pirate praised with a smile, leaning towards Rich's clenched muzzle with his own, the lingering scent of the whiskey heavy on his breath. "Please Sir, won't you bend this buccaneer over and break in his tailhole tonight?"

"Don't you worry your pretty little head about that. When I'm good and ready, pegaslut, I'll break that "booty" in," the earth pony vowed harshly, reaching for his glass on the end-table and swigging down the half-melted ice cubes laced with whiskey within. Closing the difference between their mouths, Rich joined his young lover in the kiss they both craved, shoving the flavorful bits of ice between their tongues for each of them to share. "Mmmm..."

High Tide's enjoyment of the older stud's muzzle meeting his own devolved into muffled bleats, the dancer surprised at a sweetened, chilly substance rapidly melting between their coupling tongues. The succulent ice cubes transitioned seamlessly into richly-aged whiskey that loosened up inhibitions and inspired a welcoming purr from High Tide's accepting muzzle; not too unlike Rich himself, "richly aged" but possessing all the potency of a stag on the prowl for a coy doe flapping up their tail, or in this case, wings.

Not content to stay idle, Rich put his burly earth-pony hips to use grinding himself back with the dancer's graceful motions, their frotting cocks dripping with pre-cum and pulsing in the all-encompassing heat of motion and fur. Friction robbed the pegasus of his grace, but certainly not pleasure; in fact, High Tide's wings stood on end, as if straining to reach for that imperceptible "high" of release. The pirate stud squeaked into their kiss, his moans sharp and girlish in the intensity of the moment, each mew accompanied by a tell-tale shudder from the colt's needy cock. Before long, the pegasus' "dancing" looked more like mindless humping as he relaxed into his host's grasp, content to let Rich do whatever he pleased and go along for the bull-ride.

"That's it, bounce that sweet little ass for Daddy, show him a damn good time," Rich snarled into the stallion's yielding muzzle, ending the kiss with a flicker of his tongue underneath High Tide's trembling ear, his suave voice raspy with lust. "You're about to pop off that dinky little "cannon" of yours, aren't you?"

"Yes, yes Daddy!" came High Tide's shameless reply, a scream that could surely be heard through the cheap hotel's paper-thin walls, putting a damper on the neighboring family's vacation as those embarrassed parents scrambled for an explanation on what their children heard.

"I-I'm almost there; please keep grinding with me Daddy, let me cum on your cock!"

"Grrraagh, yeah! Tell me how badly you need Daddy's fat dick breakin' in your ass, let me hear you scream for it!" Rich ordered impatiently, lifting a hoof to tug down High Tide's trousers completely to the floor and expose the pegasus' cutie-mark; a dark-blue ocean wave standing at full crest. A fittingly-energetic cutie-mark indeed, one he intended to leave his own "high water mark" upon.

"P-Please plunder my slutty ass with your superior cock, Daddy! I want to scream so hard the management kicks us out, so we'll just fuck in the parking lot instead! I-I want to b-blow my load all over your cock, so it'll be nice and wet when you shove it inside my tight pegaslut asshole!" the breathless pirate announced for all the world (and even that crestfallen nice family of thrifty tourists staying in the next room over) to hear, but especially to Rich, indulging the mature stallion's swelling cock and ego.

"Make me cum, make me whimper, make me yours tonight-Ahh!" High began to plead again, before Filthy's hoof delivered a sharp smack across the colt's bare rump, striking the colt's exposed cutie-mark like a wide target. Nothing left quite an impression the day after than seeing his hoofprint on a slut's well-used hindquarters!

"Such a cute ass you've got, so firm from all that slutty dancing," Rich appraised with a sneer, grinding himself hard against High Tide's trembling cock, milking out the last vestiges of resistance keeping his whining colt from erupting under his touch. "I can't wait to loosen it up so much that you'll never keep in step at tomorrow's show; I'm gonna fuck you harder than I'd ever screw my wife, and you're gonna love it. Cum for your Daddy, now!"

"Ha-aah-ah, Aaahhh! D-DaaAAaaaddy!" High yelled to high-heaven, and came so hard the angels probably heard the chorus over their blaring trumpets; the family next door certainly did, ruining whatever flimsy excuse the couple had come up with for their children. The colt's blue cock twitched with a shiver that ran throughout his lithe form, his passion throbbing against the imposing rigidity of Rich's unmatched maleness. High's flare swelled to full size, his testicles tightening against Filthy's own, until the first stream of gooey cum erupted across their chests.

"That's a good First Mate, cum all over Daddy's dick," Filthy encouraged with a leer as a jet of off-white seed streaked across his nose, the earth pony pushing the pegasus back and aiming his pulsing cock slightly lower, to bath their rubbing shafts in the colt's jetting cum. High Tide's climax proved brief, but intense, robbing the colt of breath and gushing several sticky rivets of cum across Rich's massive length. The pegasus' white jizz contrasted with the earth pony's black cock, which High stroked with a hoof, smearing his essence across his Daddy's equipment until he'd oozed the last of the leaking spunk into their laps.

"Waste not, want not, First Mate. Get Daddy's cock nice and wet with it; cause it'll be inside you very soon."

" H-How soon, Sir? I can't wait..." the colt huffed weakly, the pirate's feathered hat sitting crooked on his mane. The white-dotted head of his half-hard cock dribbled cum all along his lover's length, coating almost every inch with warm, sticky stallion-produced lubricant, as yet more trickling across their bellies. The colt's "enthusiasm" for Daddy kept him hard enough for more action, still ready to present himself at a moment's notice and allow Rich to give him the rutting they'd been craving the moment he slipped into the mature stud's hotel room.

"Soon as I finish my next drink. Speaking of which," Filthy reassured in a manner meant to disarm High's expectations rather than enlighten them, his hoof gently fondling the pegasus' still-swollen flare , earning a squirm from its lingering sensitivity. "Pour me a new one with a bit more than a shot in it, and lift your tail up nice and high while you do it. Your Daddy wants to get a good view of that sexy ass while it's still pristine, before he gets busy wrecking it."

"O-Oh, of course, Sir. Thank you for letting me cum on you, Daddy," High offered his submissive gratitude, sighing as he begrudgingly dismounted the older earth pony to stand on wobbling hooves, his floppy blue cock slipping free from the strands of warm semen clinging between their cum-covered shafts. The pegasus staggered to the coffee table, using a wing to pour the Appleloosian Standard while a hoof emptied some ice into the glass, his idle wing quickly adjusting the gaudy hat upon his head. "I'll get that drink ready right away!"

"You do that," Rich stated, his eyes intent on taking in the sight he'd been yearning to relish; High Tide's two-toned tail rising straight up, lending Rich a perfect view of his faultless tailhole. Underneath that bothersome tail sat a dark-blue, puckered circle of pleasure slightly glistening with sweat, perfectly tight and about to get the affection from a stud it truly deserved.

"Hmmm, actually, why don't you take that drink instead? I've got something a lot tastier in mind."

"Oh? Like wh-A-Aaahh!" The colt questioned, until Rich made the answer quite clear with his tongue. The earth pony rose from the couch, his muzzle slipping casually underneath High's swishing tail to deliver a very different, but no less intimate kiss. Rich's tongue swirled around the circular entrance to High's tense tailhole, slathering that enticing orifice with spittle before lapping into the actual opening itself.

The earth pony's strong hooves held the colt's rump in place while Rich drove his tongue deep inside his colt's asshole with the same gusto he'd given during their make-out session, slathering the surprised stud's insides with his tongue and enjoying its softness; after all, that same sensation would wrap itself around Rich's dick soon enough, he might as well give the pegasus something to help accommodate the length that aimed to make him whimper.

"Pah!" Rich puffed as he withdrew his tongue, repeating the circle around High Tide's pliant hole, leaving it glimmering with saliva and damp to the touch. High Tide's wings flapped, lifting the pegasus slightly off the table, but Rich held his quarry down to earth. No way he was letting such a fine piece of booty slip away!

"Mmm, it's been awhile since I've dined on such a fine ass. Did you like that?" Filthy asked plainly, as if lapping his tongue across another stallion's asshole were the most natural thing in the world to do. High Tide's rear hooves quivered; if his forelegs weren't mounted on the table or clutching the half-spilled glass of whiskey, he'd likely have fallen down from the rush of sensations lathering that welcoming hole.

"I'll take your amazed silence as a yes."

"O-Oh! Sorry Sir, I-I was just surprised is all; I-I've never had anypony do that before, not even my colfriends! It was, ah, new, is all," High admitted with a hesitant grin as he glanced back at his older lover, the colt's cheeks wearing a stark shade of red. "I'm not your first, that much is for certain..."

"Back on the road, we didn't have all those fancy lubes to work with like you young guys do. Sometimes, spit was all we had, and we made the most of it. Still...you didn't answer my question. Did you like it?" Rich prodded further with a raised brow, darting out his tongue to lick at High's ass once more, drawing out a wanting swish from the colt's inpatient tail.

"Yes! Ah, I love how it feels, and I w-wish all the guys in the dressing room I've fooled around with took the time to tease my ass like you, Daddy," the pirate encouraged cheerfully, genuinely thankful for his experienced host taking time to loosen him up during their foreplay. After all, he'd likely need every bit of help to accommodate the earth pony's impressive girth.

"You'll have to introduce me to a few of those studs whenever I'm back in town, so I can give them a personal introduction to rimming. For now though, you're the only colt on my mind. It's about time you got off my thoughts..." Rich replied with a playful sneer, before rearing up and placing both his forelegs on High Tide's rump, his cutie mark nearly covered by the mature stallion's hooves as Rich lined himself up to the sloppy hole he'd just finished lubricating. "...and onto my dick."

"Oh, Celestia, finally, yes!" High Tide whinnied like a mare desperate for cock, his forelegs pattering at the table with worried anticipation for the rock-hard stallionhood slipping between his taut flanks. Having unlatched the buttons of his costume shirt, High Tide's fuzzy chest heaved deeply upon submitting to Rich's initiative, accepting the earth pony's stout weight settling upon his back. The soft-blue pegasus glanced back at the older stud mounting him, his violet eyes arresting Rich's ice-blue gaze with their beauty, the sighing plea arousing the earth pony's long-buried passions.

"I'm ready for you, daddy; please, won't you take me?"

Rich grimaced, the handsome pirate's plea drawing a greedy twitch from his cock, the mounting stallion's hips moving on auto-pilot to jam his length between the colt's firm ass-cheeks, exploring what would soon be his. It took all Rich's willpower to keep from thrusting right into that tantalizing tailhole at the behest of those eyes alone, but the colt didn't know what he was asking for; young bucks were always in a rush. Shoving himself inside so abruptly, no matter how much he desired to do just that, would leave Rich's lover screaming in all the wrong ways! Blessed as Rich was in the cock department, such a size demanded slightly more preparation...

"I'll take you alright, when I'm good and ready, bitch. This is daddy's ship, not yours; so don't you dare think of mutiny, or I'll have to get rough," Rich chastised, delivering a sudden smack across the insolent colt's fine flank, forcing another delightful chirp from the subservient pegasus. Rich took his time, making sure that their leftover cum and the fresh saliva coating High Tide's tight hole properly slathered his member, until their mutual luster coated every ebony inch. Just to be safe, Rich withdrew his hips briefly, making High moan underneath the thorough lashing of his tongue once more, until the pegasus' jiggling "booty" proved too tempting to delay claiming any longer.

"Daddy's ready to break you in now, buccaneer."

"Celestia! You feel so s-strong on top of me," High huffed underneath the earth pony, wigging his rump invitingly to grind himself along Rich's probing cock.

"Just wait until I'm inside of you, then you'll see how a real mustang ruts; oh wait, guess it's your lucky day," lining up at that offered hole, Rich's hooves latched the pegasus' hips firmly, rooting the colt in place to keep the excitable stud from slipping out of position in his giddiness to be claimed. Growling lustfully, Rich began pushing forward, watching the black head of his cock press, prod, and finally, fantastically, slip into the heavenly slut's taut tailhole. "You don't need to wait!"

"F-Fuck!" The colt squeaked shrilly, his beautiful lavender eyes and tantalizingly-tight tailhole each widening in tandem as Rich's flared head gingerly slipped inside, the first few inches the most difficult to accept. High's whole body tensed up, his neck and shoulders trembling so much the his cute hat almost fell off!

"J-Just a little more-Rrragh! There, that's a good bitch..." Filthy snarled, pausing to recuperate as the full width of his flare popped into High Tide's ass, the thickest and hardest part of his dick finally enveloped within the pegasus' incredibly warm body. Rich's powerful heartbeat throbbed through his shaft, and he could feel the same thumping reverberating through the colt underneath him, bottom and top equally astonished at the fulfilling pleasure of taking, or being taken.

"It's been far too long, argh, too long since I've broken in a slutty colt," the earth pony groaned, treasuring the sensation of a dancer's trim body snug around his needy stallionhood more than any sparkling doubloons. Rich was thankful that something so big managed to fit into a young hole so warm, one that squeezed him tighter than any cunt could hope to, even the one belonging to his beautiful wife. Oh, if only Spoiled saw the wolfish grin on her husband's muzzle as he mounted a colt half his age; her jealously towards the lucky stud would never end!

"Celestia, y-you're so big, Daddy. The biggest c-cock I've ever had, e-ever seen, ever felt i-inside me..." the pegasus murmured in pleasure, relaxing his forehooves on the table and breathing deeply to ease further penetration, grateful that Daddy lent him a moment to prepare for the rutting Rich surely aimed to give. That moment of pause passed quickly, as Rich steeled himself for the action.

"Is that so? How can you really know that, when you haven't even taken it all yet, my little pegaslut?" Rich questioned with a raspy growl, roughly hiking up on the table and wrapping his hooves around the joints of High Tide's open wings, using them as leverage to drive himself deep into the squirming colt impaled on his shaft. "Grraagh! That's a lot more like it! Feels a whole lot bigger now, doesn't it?"

Even back in Rich's road-roaming days, excitable pegasus studs like the one moaning underneath him always proved the easiest to entice into some raunchy backroom fun; though they never realized that they were easy prey for the savvy stallion. Their fine wings served not only as a handy gauge to determine if Rich's practiced charms piqued a colt's interest, but also made for a convenient set of handlebars for when the flirting eventually turned into fucking. Rich's hooves appraised the inviting, flicking feathers splayed across High Tide's slender back, the base of those pillowy appendages inspiring fantastic memories of those old encounters. What better way to relive them than pound the pegasus into quivering mush?

"Old habits die hard," Rich huffed in a barely-audible snort, thrusting his strong earth pony hips forward and slamming himself up to the medial ring into the tight little slut's tailhole. The motion drew a high-pitched squeak from both the colt and the table alike, Rich's unyielding cock's midsection nestling his newest conquest's puckered entrance. Steadying his thrusts using his first mate's wings, the stallion pulled himself back just slightly, before sliding that ring and a few more inches of his girth into the simpering colt's incredibly-snug asshole.

"Daddy, g-give it all to me, please! Oh Celestia, I want all of your big cock in my slutty c-colt cunt!" the colt whined pathetically, his loud cries a perverse music to Rich's lustful ears, the call of an enraptured siren surrendering himself to the moment. How could he ever hope refuse such a plea, even if he wanted to? Heck, if Spoiled and Diamond themselves walked into the room at that very moment, Rich doubted he'd be able to stop himself from pounding High Tide into high heaven!

"Take it, take all of your Daddy's dick! G-Gah, fuck yeah, here it all is!" Rich huffed through gritted teeth, the entire length of his black shaft vanishing deep into High Tide's wanting tailhole right up to the base, his swollen flare growing so engorged as to leave the slightest outline of its heft in the lean colt's lower tummy. Rich marveled at the pegasus' fit body squeezing his entire stallionhood, the earth pony's large testicles nuzzling the much smaller pair swaying underneath his subby First Mate's own half-erect cock, which constantly leaked precum all over the coffee table.

Without delay, Rich tugged his hips back and hammered his shaft into the pegasus bitch sharply, forcing a rapturous scream from the young lover quivering underneath his mighty frame; another rocking thrust, and the same effeminate shriek followed, sharp and clear enough for ponies on both floors of the dingy hotel to hear. Rich didn't care, he simply couldn't care anymore, not after so long; Tartarus claim his soul, he'd fuck this colt for days if that's what it took to satisfy his urges!

"Daddy-? A-Ah, a-aaack! Fuck yeah! P-Please don't stop, oh, d-don't ever stop!" High Tide stammered breathlessly under the earth pony's relentless rutting, Rich's body straining to act on an automatic instinct of conquest, long-neglected impulses unleashing themselves into a weighty blur hammering at the colt's accommodating tailhole.

This was a different kind of sex; not the tender lovemaking he'd enjoyed with his wife, but something more basic, raw, and supremely intense that marital conjugation ever hoped to be; in moments, Rich found himself addicted to it, washing away guilt with pleasure.

The stud latched his muzzle onto the lucky pirate's twitching ear, coaxing him to remain docile underneath a superior male and earning yet-another submissive serenade in reply, telling him that High knew his place. Digging his teeth into that ear with enough force sure to leave it sore, the earth pony's forelegs tightened their grip and pulled backward, dragging High Tide right up against his waist to ensure that his swelling cock spent every moment it could tearing into the young buccaneer's rump.

"Remember slut; this is the dick that's gonna ruin your sweet little ass for any other stallion from now on, the one you'll be wishing you had inside every time you raise that tail! Gragh! Hah, Daddy's gotta fuck that cute little hat right off his slut's empty head, right after he's done plowin' his brains out!" Rich snarled upon releasing High Tide's ear, only to latch onto the colt's supple neck instead, keeping him mounted down underneath him without any chance of wiggling free, even if the colt wished for such an escape.

"Yes, please don't stop! R-Ruin my ass, make it yours; all I want fucking me from now on are big earth pony cocks!" High squeaked in rapture, his own stallionhood swelling with arousal but hanging somewhat limply between his legs, as if conceding defeat to Rich's supreme maleness. The periwinkle dancer's floppy cock rocked at each thrust, dribbling pre-cum all along the floor underneath them and certain to leave quite a strange mess for the maid to clean up in the morning.

"With any luck, the maid be another colt for me to pound raw. Hah, I'd be sure to give him the biggest "tip" of his life," Rich mused with an aggressive huff, his mind turning briefly to future escapades until he found himself uttering a near-feral groan, the familiar sense of mounting pleasure ringing through his entire stallionhood. The earth pony's flare grew fatter, harder to control, and High Tide's eyes fluttered with rapture underneath, a silent plea on the colt's lips. Who was he to refuse what came naturally for both of them?

"Daddy's gonna cum in your ass soon, pegaslut," Filthy ground out from clenched teeth, his hips rocking forward in jerky, sharp motions, spreading the whimpering pegasus underneath wide and deep in his final moments. "Let me hear you whine for it..."

High Tide's eyes widened, finally aware of the older stallion's flare growing so wide inside his ass, leaving the dancer with a satisfying, calming sense of fullness that he'd only felt before with his biggest partners and toys, none of whom matched "MarriedMustang45's" proportions! Frazzled wings shuddering upon his back, the pegasus glanced up at his panting lover, his greased-back mane and scruffy chin a portrait of a rugged stallion whose words and deeds could coax anycolt to his whims. High Tide spoke in a cracking voice, yearning for that final reward threatening to spill inside him at any moment.

"Daddy, keep on pounding me, I-I want your flare to fill me up! Your wife doesn't know what she's missing; If I could, I'd be your ass on the side, so you could fuck me every day after work! Please, can I be your secret-slut Daddy, your faggot fuckhole-away-from-home? B-Breed my tailhole hard, I want to walk funny tomorrow so all the boys in the dressing room will be jealous when I tell them all about my Daddy's dick!"

Rich responded in a gleaming shark's smile as the words left his First Mate's muzzle, returning gentle nuzzles across the colt's soft neck, a moment of affection for this handsome bottom before the rugged rutting began again. The earth pony's lips parted, and he latched onto the back of his lithe lover's neck with his teeth, shy of breaking skin but certain to leave slightly-sore bite-marks underneath the once-pristine fur. His quarry mounted in place and rendered a docile wreck at the firm display of dominance, Rich's hips crashed heedlessly into the wanting, wet hole on offer, unleashing almost a decade's worth of pent-up lusts into the poor pegasus' supremely-snug ass.

"Spoiled would never let me do her like this, not with how much she fusses on her fur; no, but I need this," the humping stallion thought as he snarled violently, any softness in his blue eyes flaring out into a mounting fury of encroaching climax, the black flare of Rich's cock mushrooming out to its full splendor. The forceful thrusts finally send the gaudy tricorn hat flying off High Tide's head, but neither pony seemed to notice its ignoble fall, intend only on feeling and pleasing each other's heat and hardness.

"Daddy, oh fuck, you're makin' me cum!" High Tide yelped in a shrill bleat, the colt's entire body seeming to clench around Rich's conquering cock as he hilted a final time. The rough thrust had forced the colt to peak, High Tide's half-flaccid dick meekly spewing a trail of watery jizz down the pegasus own thighs, its weak force and potency sure to pale against the load building up to properly breed his ass.

Hardly noticing the pegasus' feeble ejaculation, Rich continued without pause, the earth pony's massive balls nestling up against High Tide's smaller, cuter set, eclipsing them from view before tensing abruptly. Rich's entire stallionhood pulsed, rocking inside the colt's ass on its own accord in three mighty twitches, each heralding a hard day's worth of spunk saved just for that night, and the lucky pirate who earned that glorious treasure. At last, the moment came; and came hard.

"I-I feel it! Oh Celestia, it's so damn hot! Fill me up Daddy, breed your bitch with your big cock; oh my gosh, i-it's still going?!" High mewed his praises as blissful, sticky heat blasted straight out of the bucking bronco's flared head, bathing the pegasus' well-rutted ass in the raw heat of stallion seed. Rich kept his mouth latched on High Tide's neck, pressing his weight onto the colt's back to hilt himself right up to the base, aiming to break in the dancer's tailhole so fully that he'd never forget just how far he'd been taken. Relaxing in the haze of orgasm, Rich allowed High to milk out jet after jet of his ample seed, the colt's surely-loosened ass still tight enough to coax out more cum than his wife's pussy ever could.

They shared that quiet moment of release together, enjoying each other's warmth and the lazy afterglow that followed a good rut, each recovering their breath and wits between the sparks of lingering pleasure. Rich's broke his hold, planting a rewarding kiss on High's neck, before breathing in the scent of the pegasus' soft mane. High's wings nestled up along Rich's flanks in a ticklish embrace, while Rich's lengthier black tail found and intertwined with his visitor's own white-and-purple counterpart with an affectionate tug. In the distance, a siren wailed somewhere in the city, but an agreeable silence lingered between them for a time, with a speech of only moans and sighs.

"Wow," High finally whispered in awe, earning a bemused chuckle from his stud.

"Worth the flight over here, I take it?"

"Oh, more than worth it! Don't think I'll be doing any flying soon though, hah," High admitted softly, reaching his wings along the table to grab his cup of whiskey, before it teetered off the edge of the table. "Phew, crisis averted! I don't think I'll be able to stop thinking about tonight in, like, maybe forever..."

"Ground-Pounder for life now, huh? Yeah, I used to have that effect on you fly-boys; glad I've still got the old touch," Rich observes with a nostalgic swagger to his tone, reaching for the cup High had saved and stealing himself a sip, lending the rest to his partner. "Not many guys can beat us earth ponies in the stamina department, but it's so fun to hear you pegasluts try. Always ends the same way though..."

"With an ass full of cum and a smile on our faces?"

"More or less," the earth pony affirmed, stroking High's mane with a caring hoof. He'd taken a huge risk, and felt a pang of guilt afterwards for betraying the vows of marriage...Yet, it wasn't Filthy Rich, business-savvy family pony, whose dick had just dumped its load in a stranger's ass; no, it was that nameless drifter wandering the roadside dives, getting back in the saddle. "But, who says this has to be the end?"

"Oh? Maybe it doesn't have to be...Y-You still feel hard inside me Sir; are you going to pull it out?" High questioned with a hint of worry, flicking a few fresh ice cubes into the glass to wash them in whiskey. "I mean, we made a real mess of this table; shouldn't we clean up a little?"

"Oh, don't worry your pretty little head, First Mate. When my flare's small enough to not get stuck on the way out, I'll hop off. We can clean up with a nice, hot shower together," the older stallion dismissed the pegasus' fretting as if he had nothing to fear, growling a further promise into his hear. "I hope you don't have any plans on leaving tonight; I'm not even close to being spent."

"I-I gotta fly to work tomorrow morning, but I'm free as a bird tonight...I wanna spend as much of it as I can with you inside me, Daddy," High replied earnestly, looking up at the lustful stud mounting him and closing the distance between their lips, his ears lowered in anticipation for what the night promised. Sharing that feeling, Rich's muzzle slowly parted, the familiar taste of whiskey and coke an old a companion, just like the feeling of another stallion's lips.

"I've needed a colt like you for way too long; I might be "MarriedMustang45" in the morning, but tonight, consider me single and on the prowl," Rich affirmed as their muzzles parted, intent on feeding the rekindled fire in his loins with abandon, his angelic visitor flying along for the ride.

"All yours..."

* * *

As the night went on, the lights on the Las Pegasus strip glimmered brightly, before twinkling out as dawn began to encroach upon the sky. Most of the Appleloosian Standard whiskey vanished, the sheets and pillows on the bed found their way all around the room, and more than a few ponies lodged noise complaints about Room 244 that could easily be "forgotten" by lending the hotel manager a hefty tip for discretion.

As Celestia's sun blanketed Las Pegasus, the door to that steamy hotel room creaked open, and a weary, wobbly pegasus trotted out with a dazed smile, his tricorn hat laying crooked upon his wild mane. Rich stood in the doorway, clad in a golden-accented blue bathrobe to conceal his now-sated maleness, which stood half-erect and covered in a mixture of spittle and cum from their final morning romp.

"T-There's a few guys in the dressing room who'd really like to meet you sometime, Sir. Are you going to be in town again?" High Tide stammered, whipping a stray bead of cum from his muzzle, a "protein-rich breakfast" to send him off to work.

"Maybe in a few months. Business is picking up here, might have a few more meetings to get things finalized. I'll send you a message whenever I'm around." Rich replied coolly, patting the colt on his tender rump with a winning smile. "Keep that ass toned up for me to ogle on the dance floor, that's an order!"

"Aye, aye, Daddy," the pegasus agreed with a short wing-salute, before taking a very unsteady leap into the air and gliding off, more-or-less straight towards the city, his blue fur melding with the morning sky.

"I'll be counting the days, flyboy," Rich said under his breath, knowing that an old addiction had come back into his life, like a long-lost friend that was a terrible influence, but whose company proved intoxicating all the same. The cocksure stance, a slight drawl to his voice, and even that habit of a prowling glance all came back to him; low and behold, they were already paying dividends!

"Well, I'll be a brass bit, if it isn't..." Rich blinked, just to make sure a mostly-sleepless night laced with booze hadn't addled his vision too much. Just at the end of the walkway sat a housekeeping cart, the maid on duty intending on getting an early start on the rooms vacated during the night or earlier that morning.

Normally, such carts wouldn't earn anything more than a passing glance, but the maid on staff that morning drew Filthy's hungry eyes quite readily; he was a small unicorn stallion, smaller than than most mares Filthy had seen in fact, with a light-pink coat and wavy mane holding two shades of blue. Sharing the colors and bounciness of an energetic ball of cotton candy, the young unicorn gaily pranced out of the room with various cleaning articles hovering about him, his emerald eyes soft and unburdened by sleepiness.

Rich watched the unicorn trot to the next door, knock, and slip inside with a key, unaware that a stallion twice his age was licking his lips, eager for a taste of that cotton-candy colored colt; he only noticed his returning erection when it poked out from underneath his robe into the warm desert air, bobbing at his foreleg with awakened urgency.

"Maybe some room service is in order? I've got a few hours to recharge before he gets this far, and a few more besides, until checkout time. Might as well get my money's worth out of my lodgings," Rich mused, pulling his robe back into place and shutting the door behind him, the trailblazing tycoon beginning to set a little trap for the adorable, clueless maid drawing ever-closer on his merry rounds.

"When opportunity knocks, be sure to answer the door; a saying as true in business as it is in pleasure..."

Author's Note

Filthy Rich is a really underrated stud; I imagine he was a real ladykiller in his youth, with that greased-back mane and winning smile. I thought of him as more of a wild, wandering fella during that time, breaking hearts across the back-roads of Equestria until settling down with Spoiled. He still loves his family, but there's a desire in his trailblazing heart that'll never truly fade; especially now!

I wanted to get this out before the end of Pride Month, so if you're reading this, I hope you've enjoyed it! Next up, we'll take a peek back at Shining Armor, see how he's holding up after wobbling out of that stall...