Apple Brandy stood on his porch and waved, watching his siblings and grandfather steadily move away from the homestead, until his family had disappeared behind a hill - at which point he wheeled around, dashed inside, locked the door, and bolted upstairs. It wasn’t like he typically enjoyed having the house to himself, since that meant he’d have to do all the farm work on his lonesome, but this was a particular case. As he reached the second floor, lingering by his big sister’s room, he slowed.
While he deeply respected his eldest sibling, and would never breach the privacy of her or Sugar Belle’s rooms without approval, he was desperate. He hoped - no, prayed he wasn’t about to rummage through her things for nothing, unsure if she even owned what he was looking for, yet he had to look, if only to make sure. Cracking the door and peeking into her chamber, he sneaked inside.
As he sneaked to her dresser, the most likely place she would keep something so intimate, he cursed beneath his breath. If it hadn’t been for Rainbow Blitz and the stupid bet he’d made, he wouldn’t be skulking about and acting in such an unseemly way - then again, he couldn’t change the past and he was not about to throw in the towel. Opening the top drawer of her dresser, blushing at the sight of her unmentionables, he carefully began sifting through her garments.
Not even two weeks prior, he’d had a silly conversation with his Blitz about the so-called No-Nut-November challenge; while hadn’t heard of it until then, a great many stallions would refrain from any sort of masturbation or sex, keeping themselves from blowing a load for the entirety of the month. He’d thought the notion was silly, seeing no point in it whatsoever, until his friend had laid down a gauntlet - whoever could overcome the little test, abstaining from cumming for the duration, would win a hefty amount of bits from the loser.
Never one to turn down a challenge, especially one which involved his companion, he’d immediately agreed to the wager. The rules were simple enough - he and Blitz would each buy a chastity cage for themselves, ensuring neither could get erect, and then give one another the key to their cages. If or when one of them asked the other to be unlocked, without a darn good explanation, the victor would be declared.
Unfortunately for him, the little gamble had metamorphosed from novel to extraordinarily frustrating within mere days. He’d tried - sweet, merciful Celestia, he’d tried to ignore his stallionly urges, but they inevitably became too much to bear. Desperate for some relief, unable to concentrate or even think clearly, his libido had ultimately led him to the library to distract himself.
While he was far from what he’d describe as a bookworm, surrounding himself with literature typically got his mind off stressful matters - ironically enough, shortly after arriving at his destination, the polar opposite happened. Just as he’d found and sat down with an agricultural journal, he overheard one of the patrons whispering to his friend, or possibly lover, about something called a dry orgasm. Keenly interested in the subject, sensing his cage get tighter with every salacious word, he changed tactics and looked up some literature on the subject.
He’d heard that stallions could get off without cumming, but he’d never really given much thought to the subject - that was, until he found himself suffering through lustful thoughts day in and day out. After a bit of research, done in the dead of night and in the privacy of his bedroom, he ultimately found the information that he’d been looking for. Apparently, if what he’d read was right, a stud could experience something called a dry orgasm solely from prostate stimulation.
His forehoof brushed against something hard buried amongst the silken garments, snapping from his stupor. Cautiously grasping the object and lifting it from the drawer, his heart skipped a beat. He hadn’t been sure his sister even owned a sex-toy, yet there it was; hewn from glass-like crystal, complemented by a ruby band around it’s length, and with a little gemstone apple at its base, the dildo was just what he needed to scratch his itch.
Without waiting another second, uttering a silent apology to his absent sister, he scampered out and to the bedroom. Though he’d ever played with his butt before, it wasn’t like he hadn’t extensively read up on the activity. Excited and more than a little nervous, he briefly stopped in his chamber, left the toy on his mattress, and galloped off to the lavatory to prepare for the occasion.
It was only after he’d thoroughly washed himself, both inside and out, did he return to his bedroom. His brief stint in the restroom had definitely been strange - not because it was the first time he’d ever cleaned himself in such a fashion, but because the thrill of what he was about to do grew tinged with hesitation. Though he tried to convince himself that ass-play wouldn’t inherently make him gay, a nagging shred of doubt wouldn’t leave him be.
Stopping by the bed, he knit his brow and glared at the dildo. The dong wasn’t that big, roughly comparable in size to the average stallion, so it probably wouldn’t be that difficult to use - he hoped. Crossing to his nightstand, retrieving a bottle of lube he usually used to stroke himself off, he crawled onto the mattress, rolled to his side, and got comfortable.
“A…all right, Brandy, just nice and slow,” he whispered to himself, attempting to quell his mounting anxiety.
Taking the dildo in one hoof, he gently bit down on the bottle of lube, flipped the cap, and drew a line of the slick substance along the sex-toy. He really didn’t have any reason to be so nervous, considering he’d seen a fair share of smut involving foreign objects, but he couldn’t shake his persistent hesitation. Closing his eyes and slowly exhaling, doing what he could to calm his frazzled nerves, he leaned to the side and brought the dong to his tush.
The second the cold, unfeeling crystal touched his pucker, he tensed. Had he thought about it beforehand, he would have warmed the infernal thing in the shower several minutes beforehand - alas, the idea hadn’t occurred to him at the time. Steeling his resolve, knowing that the lewd toy was his best and possibly only chance to get some sexual relief, he steadily sank the dildo into his winking backdoor.
The sensation of having something going inside him was odd, but not what he’d describe as unpleasant. As he bent at the waist, curling into a ball to better reach his behind, his thoughts began to wander. He knew there were plenty of stallions who were into bottoming - heck, he knew a couple such studs himself, although he genuinely couldn’t say what the appeal was. The dong didn’t feel bad, but it definitely wasn’t as good as stroking his…
“Mmmmph,” he spontaneously whimpered, as a wave of pleasure coursed through him.
Totally unprepared for the blissful sensation, he paused. He knew good and gosh darn well what a prostate was, but he had no earthly idea having it stimulated would be as awe inspiring as it was. Withdrawing the toy, which he’d only managed to take roughly half of, he depressed the sensitive little love-button a second time; once again, a rapturous surge set his nerves alight.
Moments after the sensation struck him, it felt as though his cage constricted; he realized that there was no way that the chastity device was actually getting smaller, simply keeping his stallionhood from growing erect, yet it was a reminder that he may have struck gold with his lascivious plot. Holding the toy still, playing with the angle just a bit, he gave himself a minute to acclimate to the feeling of being penetrated. If his little scheme worked, he’d definitely be able to win his little wager with Blitz!
As pleased as he was with the discovery, he wasn’t done yet - not by a long shot. Momentarily straightening back up, he fumbled for a pillow beneath the headboard, pulled the cushion under his head, and made himself comfortable. It wasn’t like he had any experience doing something so scandalous, yet he knew enough that staying relaxed would make the endeavor all the more enjoyable.
His eyes drifted closed, his racing pulse slowed, and he sighed in contentment, resting his head on the downy pillow. Moving at a snail’s pace, still adjusting to the wondrous and alien sensations the toy afforded, he gradually started fucking himself in earnest. He’d be lying if he said using one of his sister’s dildos didn’t make him slightly ashamed, but it felt too darn good to stop.
On and on he went, fixating on the sensitive spot in his rear, until an ugly issue raised its head. Situated as he was, on his side and with a foreleg reaching behind himself, a cramp in his flank grew too intense to ignore. Though he’d had no intention of stopping, since the dong had finally warmed from his body heat, the situation left him at an impasse. Unable to comfortably continue, he lifted his hind leg and peered down at his groin.
His eyes widened in shock, spying a copious amount of pre-cum leaking from his caged stallionhood; the sheer volume of the stuff was shocking, seeing it slathered over his balls and inner thigh, yet it did little to deter him - if anything, it was more proof that the anal was working. It hadn’t taken him long to realize anal play had felt good, yet he’d failed to nice just how worked up he’d been getting from it! Scrunching his snout, determined not to quit, he surveyed his surroundings and attempted to find a solution.
The dong he’d purloined definitely seemed to be doing the trick, although it came with two clear setbacks; for starters, it was made of crystal and, if he had to guess, couldn’t endure any sort of severe abuse - secondly and more annoyingly, the decorative apple at its base, while cute and quite fitting, meant he couldn’t simply plop it on the floor and ride the darn thing. On the cusp of simply flipping over and hoping he wouldn’t develop a mirroring cramp, he noticed something on the floor - something he’d likely seen dozens or hundreds of times without giving it any thought.
Situated between the door and his bed, mere feet from where he lay, a knothole rested in the center of one of the thickly cut floorboards. The hole looked as though it might be big enough to fit the rounded bottom of the sex-toy lodged in his backside, but there was only one way to find out. Pulling the dildo from his tush, feeling the cold air briefly grace his insides and slightly gaped pucker, he pushed himself up and hopped down from the mattress.
Balancing on three legs, with a rope of pre-dangle from his groin, he squinted from the tiny opening to the toy in his grasp. Even if the thing did fit in the knothole, he wasn’t guaranteed a solution. Should the toy break, he’d have to either lie and feign ignorance to its damage or, if he felt like being crucified by his family, fess up to borrowing it to sate his hedonistic needs. Mulling his options over, he leaned forward and fitted the base of the toy into the cavity.
As the dong dropped perfectly into place, with the entire usable section standing like a tiny, depraved monolith, he grunted in consternation. “Consarn it…”
Spinning around and placing his forehooves on the bed, he gathered up both the pillows on the mattress. Playing with his ass had been amazing, far, far better than he’d anticipated, to the point where, had he kept it up, he felt as though he may have gotten some relief. As he turned and sandwiched the toy between the cushions, knowing full well he may risk breaking his sister’s marital aid, he stepped over the dildo and slowly sank to his haunches.
It wasn’t the most natural thing he’d ever done, carefully squatting down to impale himself on a dildo he’d borrowed from his sister, but it was the best solution he could think of given the circumstances. Bending at the waist and watching himself sink towards the little crystalline pillar, he kept his metaphorical hooves crossed. As the tip kissed his entrance, a thrilled shiver up his spine.
Lowering himself further and further still, taking the dong deeper than he had on the bed, his ambitions soared. He’d presumed the spiral band around the toy had simply been for decoration, making it appear not dissimilar to a candy cane, yet the raised band delicately caressed his p-spot with every inch he slipped into his quivering depths. All but hilting himself, with only an inch left unsheathed, he languidly began raising and lowering his hips.
One benefit of his newfound arrangement was that, aside from being more comfortable than he’d first assumed, he was able to use his hind legs to control the depth and angle of his plunges - that being said, he felt even more compromised than he had on the mattress. Should anypony see him or, Celestia forbid, walk in on him, he’d die of embarrassment! Glancing to the door, yet continuing to bounce in place, he ensured the lock was turned.
Once he’d ensured that nopony would barge in on him, he continued wantonly bucking himself. His caged stallionhood and ripe balls swung beneath him, slathering the floor in sticky ropes of pre, while he moved faster and faster still. As shameful as it was to admit, he quickly lost himself to the pleasure of the kinky act, yet he swiftly realized how he could enjoy himself even more than he already was.
Slowing to a halt, he leaned back, threw his forelegs back, braced himself, and bucked his hips. The pressure on his prostate skyrocketed, drawing a whorish and very unbecoming moan from him. If he’d known using a dildo would be as fun as it was, he would have purchased one ages ago! Closing his eyes and focusing on the bliss of having his p-spot crushed with every plunge, he did what he could to assure himself that he wasn’t gay.
His chaste cock drooled uncontrollably, making a grand mess beneath him, while it struggled against its confines. Though the ache at his crotch was overshadowed by his bliss, the metal cage strained against his too. Completely ignoring his package, he subconsciously increased his pace.
He’d never thought he’d end up doing something so indecent, but the exhilaration of the moment eclipsed his higher functions. Slowly but surely, an odd sensation welled within his lower abdomen; it felt somewhat akin to a building climax, sending his heart rate through the roof, but this was different. Gnawing his lower lip, he unabashedly flailed his hips and reached a fevered pitch. He just needed a little bit more, just a final nudge to get some sweet relief, and he’d be darned if he was going to stop until he got what he needed.
Sweat beaded his coat, his breath fogged the air, and the seemingly endless tide of clear, sticky juices dribbled from his locked cock, while he flew into a frenzy. He was so close, so very close to cumming, yet it somehow eluded him. Growing increasingly desperate, leaning back further, he raised his waist, steadied himself, and slammed his ass down on the toy, hilting the entirety of the exposed shaft.
With that final descent, he was granted his wish. His eyes flew open in shock, as a tsunami of ecstasy overtook him. Braying out like a claimed mare, with his thighs trembling uncontrollably, cum gushed from his chaste package. Without so much as touching his stallionhood, he’d cum harder and quite possibly faster than he had in his entire life.
Awash in the euphoria of his release, he lowered his head and took stock of the aftermath. The floorboards, pillows, and even one of his thighs were covered in the gooey aftermath of his good time, though he wasn’t overly concerned with the mess. Seeing as how he had the house to himself for at least a few hours, he’d have plenty of time to get everything cleaned up and stash his sister’s toy before his family returned.
He could have stayed where he was for ages, if only to recuperate and regain his strength, yet a sound from the balcony caught his ear. Wearily turning his head and looking to the side, fully expecting to see a bird outside, he froze. The turquoise coat and cerise eyes were unmistakable, belonging to only one particular pony.
The glass door cracked open, as the blushing pegasus stuck his head inside. “Having fun?”
“B…B…Blitz?” he stammered, watching the stallion open and crawl through the balcony door.
Walking in with a very unsteady gait, Blitz bashfully smiled. “Hey…”
Brandy was stunned. Not only had his friend decided to spy on him, seeing him shamelessly riding a dildo, but the prismatic pony had seen fit to come in and talk to him! Unable to move, feeling very much like a young fawn, he threw one foreleg between his thighs to cover his shame. It was bad enough that he’d lost the bet, having inadvertently blown a load, but the last thing he wanted was to be seen in such a humiliating state.
“I…if it makes you feel any better,” Blitz sputtered, extending a foreleg to display the shattered remnants of his cage. “I - uh - I couldn’t help it - after seeing you in here, I just…”
Looking past his friend and to the balcony, Brandy noticed exactly what the pegasus had meant. Ropes of spunk covered the veranda, with a few strands clinging to the glass door, firmly marking his companion’s defeat. While it was a small consolation that he’d won the wager, he was less than pleased with the sticky situation he found himself in.
The pegasus trailed off and rubbed the back of his neck, while Brandy tried and failed to wrap his head around what was happening. Staring at the shattered remains of Blitz’s cage, he scrunched his snout. A part of him was thankful that he’d purchased a metal chastity device, since his friend had opted for a cheaper, less durable plastic model, yet that did little to comfort the indignity of being found with a dildo lodged in his behind.
The revelation that Blitz had not only watched him but gotten off to him was jarring. He’d often assumed that the pegasus had a preference for studs, but that assumption was proved true in a very awkward way. Throwing his weight forward, reassuming his squatted position, he clamped his tail over his backside.
“So - um -” Blitz began, his cheeks going an even darker crimson, “since the little competition is out the window, do you wanna try that with something else?” Flexing his groin, sending blood rushing into his growing length, he waggled his eyebrows.
Even the hint of doing something gay with his friend snapped Brandy from the afterglow. It wasn’t like he had anything against stallions who preferred guys, but that was the last thing he’d consider doing - especially with Blitz. Pursing his lips and looking the pegasus in the eye, he got to his hooves, unsheathed himself from the dong, and turned to face his companion.
“Ah’d rather fuck Grampa Smith than you,” he huffed, gathering up his sullied belongings and trotting to the exit. As he crossed through the threshold and into the hallway, without so much as looking back, he cleared his throat. “How about you go get those bits you owe me, since Ah won…”
