The mask was floating in the space where the creature’s head would be, still illuminated with unnatural yellow energy. As Rhys watched in horror, the cracked mask slowly descended onto the blackened stump of the creature’s neck. Flame suddenly blossomed from behind the mask, forcing a scared cry out of Rhys as he threw his arms up to shield himself from the sudden flash of sparks. He watched in terror as the flames started to coil, threading around themselves to form a knit of bone and flesh and skin and hair behind the grinning, evil expression of the mask. Two tongues of flame shot out from the top of the creature’s head, curling back besides his head in long, thick horns.

Rhys’ brain screamed at him to get up and run but his body would not respond, frozen by supernatural force or the weight of his own horror as he watched the demon reach up and crack its neck as if it were a boxer about to step into the ring.

“Well, well, well,” the sinister snicker that fell from that jagged pumpkin grin sent chills through Rhys’ bones, “what have we got here?”

Happy Mischief Night y’all! Have a special fic just in time for the actual day itself, in which prankster Rhys smashes the wrong jack-o-lantern 😉

Warnings for dubcon, spanking, demon sex, slight humiliation, and light cumflation near the end! And pumpkin spice blowjobs. 

The air was dry and warm, despite the fact that it was nearing midnight.

The light jacket clung close to Rhys’ body as he walked briskly through the dark neighborhood. Most of the lights in the windows of the houses were off, though many Halloween decorations were presumably set on a later timer, still lighting up and spewing fog all over people’s well-kept lawns and patios even as few were out and about to enjoy them.

He shrugged his backpack up on his shoulder, the contents jostling and clinking around inside. Rhys’ insides squirmed with excitement as his brain swarmed with plans—he had spray paint, eggs, silly-string, and toilet paper stuffing his pack to the brim. Usually he had Vaughn to share part of the load or double their artillery, but, well…

Vaughn said that they were too old to do this kind of stuff anymore. And that he had to impress his new professors and “study,” like okay? Rhys had midterms too, but he had been smart and studied beforehand so that they could still go out and wreak havoc, as was tradition.

But no. Vaughn had decided to be boring and try to pretend he was too mature for this stuff now that they were in college, and leave Rhys all alone. Which was fine! Rhys was enough of a badass to do this alone without Vaughn’s help, and once he showed his friend pictures of all the fun he’d missed out on, surely he would change his tune and be down to participate in the festivity again next year.

This neighborhood was fairly quiet, far enough from the main campus that it was populated mostly by families and other long-term residents, rather than raucous college students keeping the alcohol flowing all night long. Rhys had plans to party tomorrow night, on Halloween proper, but tonight—tonight was all about mayhem.

The first house—a nice, Spanish-style remodel—fell victim to a volley of eggs and several rolls of toilet paper. The second had its bushes coated in silly string and animatronic witch pushed over and splattered with the stuff as well. The third, he brought out the can of spray paint, in his favorite shade of acid blue, and marked the cheesy foam gravestones with a sloppy “Rhyz-Winz” and his own swirly, circular signature symbol that he hoped to get tattooed on himself as soon as he saved enough money.

Rhys had a spring in his step as he jogged across the street away from the pranked houses, casting a devilish look over his shoulder. Fuck. What a rush.

Vaughn had no idea what he was missing.

He laughed, giddily out of breath as he slowed to a walk, greedy little eyes sweeping over the rows of homes as he sought out another target. There were plenty of possibilities, many avenues through which to execute his mischief. He hummed, rubbing his chin as he rounded a corner—and immediately ran into his next victim.

Smack-dab in between the cheery, modern-looking houses was one that looked like it’d been ripped straight out of a classic horror movie. It was dark and old and vaguely-Victorian, surrounded on both sides by wide, patchy vacant lots. The windows were dark, curtains drawn, but its stoop was vibrant and glowing from the light of a single, large jack-o-lantern sitting on the front step.

A fiendish chuckle escaped Rhys’ lips as he raced up to the house, slowing down to tiptoes when he reached close enough. The place looked practically deserted but there was a carved pumpkin sitting on the stoop, so there was no harm in being careful.

Rhys braced his hands on his knees, crouching down to get a better look at the jack-o-lantern. It’d been carved on a pretty sizable pumpkin, bigger than Rhys’ own head. The face was sharp and grotesque, its smile jagged and wide and its eyes creased in wicked amusement. A vicious, V-shaped scar cut up through its forehead and down through its left eye. It even had eyebrows, arched downwards to finish the vicious, eerie visage. Who gave their jack-o-lantern eyebrows?

Oh well. It’s not like it mattered, Rhys thought, when it was seconds away from being smashed.

The jack-o-lantern’s flesh was warm, the light inside flickering as Rhys’ grabbed it, tilting it up to look right in its wicked face. He snickered as he lifted the pumpkin up, grunting for a second at the weight as he supported it against his chest.

Shit. This was easier with two people.

He managed to get the pumpkin up over his head, arms trembling slightly as he turned away from the house and looked back down the sidewalk. He grinned like a maniac before he heaved with his entire body, throwing the pumpkin as high up into the air as he could manage.

Its shadow cut across the glow of the moon for a brief second, falling in a slow arc before it smashed violently across the sidewalk, stringy guts splattering everywhere.

Rhys let out a silent cheer, hopping up and down as he skipped over to the destroyed pumpkin, flushed with pride. He grinned so brightly his cheeks almost hurt as he looked over the carnage.

Huh. Weird. The main body of the pumpkin had been smashed, broken into chunks and scattered amongst the gooey innards. But the jagged, roughly-hewn face that had bothered Rhys so much was still completely intact, like someone had taken scissors and cut the entire carved expression out and rested it atop the ruined pumpkin. If you changed around the colors a bit, it might look like a smashed head from a horror movie.

Rhys bit his lower lip, shivering against the cold feeling that cascaded down his spine. He kicked out at the intact piece.

Stupid pumpkin.

He stepped over the gross heap, grinding his sole down into the shattered jack-o-lantern before starting back off down the sidewalk. He had better things to do than think about a dumb, weird pumpkin with dumb, weird eyebrows.

Rhys had taken a couple of steps away from the house, already thinking about what pranks to pull next, when a sudden, dry gust of wind rushed at him from behind.

He froze in his step, hands fisting into the straps of his backpack. Leaves skittered around his feet. A sudden shiver ran up his spine, the hairs on the nape of his neck suddenly standing up. He turned his head slightly, his stomach churning as he finally looked behind him.

The smashed pumpkin was glowing.

Rhys jerked around to face it, eyes wide as the remains of the jack-o-lantern began to move, and not with the wind. His mouth grew dry as the huge piece of the pumpkin’s face sudden jerked up into the air, imbued with a bright yellow, ethereal light as it floated above the ground, trailing the strings of pumpkin guts behind it as it rose like a nightmarish wind chime. Rhys stared, barely believing his eyes, his heart pounding in fear.

Then one of the jack-o-lantern’s eyes winked at him.

Rhys screamed. He backed up away from the floating mask for a brief moment, before hightailing it and sprinting as fast as he could in the opposite direction. His sneakers slapped against the sidewalk, sending needles of pain ringing through his calves, but he ignored it. His heart thumped against his ribs, throat harsh with breathless gasps and sobs as he tried to run far, far away from the thing—but even as he sprinted, going as fast as he could, the houses in front of him seemed to stay in place, the sidewalk stretching out endlessly before him no matter how many times his feet slammed against the concrete.

He turned, trying to get a look over his shoulder when suddenly his toe struck a knobby bit of vegetation breaking up through a crack in the sidewalk, sending him crashing to the ground. He screamed out once more, crying for help as he tried to pull himself up. He rolled over onto his back, elbows braced against the sidewalk—but as he looked up towards the endless night sky, any further cries died in his throat.

A massive, bulky shadow cut across the inky navy and heather purple of the sky above. It was bigger than anything Rhys had ever seen before, far too large to be human. It seemed clad in heavy, trailing robes that rippled and shimmered despite the sudden lack of breeze.

The mask was floating in the space where the creature’s head would be, still illuminated with unnatural yellow energy. As Rhys watched in horror, the cracked mask slowly descended onto the blackened stump of the creature’s neck. Flame suddenly blossomed from behind the mask, forcing a scared cry out of Rhys as he threw his arms up to shield himself from the sudden flash of sparks. He watched in terror as the flames started to coil, threading around themselves to form a knit of bone and flesh and skin and hair behind the grinning, evil expression of the mask. Two tongues of flame shot out from the top of the creature’s head, curling back besides his head in long, thick horns.

Rhys’ brain screamed at him to get up and run but his body would not respond, frozen by supernatural force or the weight of his own horror as he watched the demon reach up and crack its neck as if it were a boxer about to step into the ring.

“Well, well, well,” the sinister snicker that fell from that jagged pumpkin grin sent chills through Rhys’ bones, “what have we got here?”

A strangled noise creaked from Rhys’ throat as new tears splashed down his paralyzed cheeks. The monster’s black wings stretched, blocking out the scant stars above.

“Are you the one who smashed my pumpkin?”

His voice was frozen, hardening like a lump in his throat. The creature snapped his fingers.

“Time’s-a-wasting, kiddo. Answer me. Are you. The one. Who smashed. My pumpkin?” The demon demanded, pointed a clawed finger at his mask.

“I-I—“ Rhys sobbed. He didn’t know the right answer, what to say to send the demon away. He wanted to go home. He wanted to see Vaughn. He wanted to be away from this….this thing.

So he told the truth.

“Y….yes….yes, it was me.”

Amused laughter rent through the air.

“There. That wasn’t that hard. Honesty really is the best policy, ain’t it?”

Rhys was far too terrified to reply. His legs and arms shivered as he tried to lever himself up, only for a large, booted foot to stomp just between Rhys’ thighs. The young man jumped as he heard the sidewalk crack.

Fire leapt from behind the monster’s pumpkin mask as the wicked grin split even further.

“Oh ho, just because you admitted it, kiddo, doesn’t mean you’re off the hook just yet. Jack’s gotta make sure you really learn your lesson.”

Rhys screamed as the demon suddenly descended upon him, expected his flesh to be rent and his blood spilled across the sidewalk but instead he was seized about the waist and lifted bodily in the air as if he were a bag of candy. Rhys flailed, kicking out at the air with his long legs. The demon’s laughter filled the night, biting him right down to the bone.

Rhys was flung across the demon’s lap as he took a seat in midair, the wind nearly knocked out of his lungs as his chest impacted with the creature’s rock hard thigh. He whimpered, scrabbling against the demon’s leg for purchase. He was both hot and cold to the touch, feeling changeable and uncertain, like smoke and wind caught up and ballooning inside discarded fabric. Rhys tried his best to crane his head, to look behind his shoulder and up at the demon to figure out what was going on, when something hard and sharp and solid connected harshly with his rear end.

“Ugh!” Rhys choked out, spit and snot flying as he was jolted forward in the demon’s lap. His stinging backside hammered home exactly what was happening to him as he stared blankly in horror.

The demon was…spanking him.

Rhys had never been spanked once in his life. His parents never believed in such archaic punishments, merely taking away his video games or hiding the ice cream if he misbehaved. In fact, no one had dared to lay a hand on him since he’d defended Vaughn from some local bullies when they were young. The sharp, heavy blows against his butt were a shock to his system, chill dripping down his spine even as his rear chafed and warmed from the brutal whip of this—Jack’s—hand.

“You’re real lucky this is all you’re getting,” the demon snarled, giving Rhys’ ass a harsh squeeze after he smacked the boy’s cheeks together so hard they wobbled like Jell-O. Rhys squirmed at the pinching, his delicate skin already puckering and swelling underneath the demon’s claws. Part of him prayed that Jack was through, but whatever god had allowed him to fall into the monster’s clutches clearly had no desire to let him off easy. And so he let out a mortified groan as Jack’s claws grabbed his waistband and practically ripped his pants down over his ass.

The spanking hurt twice as much now that Jack could freely rail against his bare skin. The demon’s hand was hot like a firebrand, bruising and burning his skin even with the quick swats he rained upon him. Rhys whimpered, tears again dripping freely from his eyes at the pain as he struggled to hold on, to stay in the demon’s lap as his punishment continued. He shut his eyes tight, teeth clenched as he tried to ride out the hurt, hoping that Jack would be satisfied soon.

But as blow after blow smacked against Rhys’ backside, something changed, much to the boy’s dawning horror.

The pain was still there, but his ass was practically numb from the amount of times he’d been hit. Yet, the lack of sensation in his butt was the least of his concerns as disgust twisted in his belly, mingling with the unmistakeable feeling of warm tension curled up in a pulsing ball just a little bit…lower.

He….he was hard. He was god-damn hard.

Rhys felt ill. His head spun. He couldn’t comprehend how he could possibly be getting horny from the brutal thrashing this terrifying creature was lashing across his ass. His entire body heaved on the next slap, his spine curling upwards like a ribbon as his hips thrusted mindlessly. The arousal in his loins wound tighter, yanking his crotch forward with every slap as if it was being pulled by a string.

Before long he started to rut proper against Jack’s thighs, hips now moving independent of the impact of the demon’s hand. He worried his teeth into his lower lip, eyebrows knit together as he rubbed his crotch against the demon’s lap. Unfortunately, it wasn’t long before Jack noticed the lack of pained screams breaking from Rhys’ lips, and the young man finally let out a yelp as Jack stopped spanking him, instead pinching the meat of his ass sharply between two claws.

“I think you’re enjoying your punishment a little too much. Filthy ‘lil brat, ain’t ya?”

Rhys didn’t bother answering, merely rocking his ass up against the demon’s hand. Jack’s palm rested gingerly against the boy’s behind, fingers occasionally pressing into his flesh as if he was judging the ripeness of fruit. A dark, musing hum trailed from Jack’s hewn teeth as Rhys panted from both pain and pleasure. He squeaked suddenly as Jack’s free claw dug into his hair and yanked his head back, the demon arching over his lap to stare down into Rhys’ watery eyes, his own blazing sockets considering.

Rhys let out a gasp as he was suddenly shoved from Jack’s lap, landing in a messy heap upon the dirty and grass of the vacant lot. He struggled to sit up, arms shaking, but claws quickly gripped into his hair again and yanked him forward, forcing him to sit up on his knees.  

“Congrats, kiddo, I decided to reward your trick with a lil’ treat. Besides, it’d be a shame to totally waste someone willing to get it on with a demon,” Jack cackled, reclining back in his invisible chair as he spread his large thighs open. Before Rhys’ eyes, a spark—much like the one that had formed Jack’s head—ignited the demon’s crotch, the sudden explosive bed of embers giving birth to a series of large, undulated appendages that twisted and writhed with an ungodly energy. And just as Rhys was wondering whether the demon planned on roasting him alive from the inside, the tongues of flame banded together, congealing until they formed something thankfully solid—and long, and firm, and shaped much more like the cocks Rhys had grown familiar with thanks to his nascent porno habits.

It was thick, and nearly the length of Rhys’ forearm, with bumps and ridges patterned along the shaft. It appeared textured and almost waxy, something undeniably organic sprouting from the infernal mass of the demon. It flexed slightly, pulsing with some unknown fluid as Rhys cautiously reached out to touch it.

“You….” Rhys touched lightly against the side of the demon’s shaft. A wide grin spread across Jack’s mask.

“Yeah. I know.”

“You have a pumpkin dick,” Rhys finished, looking up at the demon, a slight cheeky grin pulling at his lips. Jack’s fiery lips dipped in a frown.

“Watch it, or I’m gonna ram this through your frikkin’ skull,” Jack growled in warning as he grabbed the base of his shaft, stroking it up and down in rapid succession. Rhys watched as it stiffened, curving up slightly towards Jack’s belly as bright yellow, glowing fluid began to bubble up from the tip.

“Pumpkin dick….eat me, kiddo,” Jack grunted, his claws clenching tightly in Rhys’ hair as he tugged him forward.

“I mean it.”

Fear still pumped through Rhys’ veins, but a fire had been lit under him, sending his arousal and adrenaline boiling as he stared up at the solid, carved bulk of the demon. Now that he had a moment, not blinded by terror and disgust, to take him in, he noticed the nuance of his form. Shadows swirled and lifted about him like dry ice, and yet Rhys could see the sculpt of an undeniably human form in his chest and stomach and thighs. His skin, though washed in darkness, had a cold, blueish-tan tinge to it that hinted at mortal flesh, despite the demon’s other gnarled, otherworldly features.

To summarize. He was…kind of attractive, up close.

Rhys knew that was insane, absolutely fucking insane, but this entire night was equally so, and if Jack was insisting that something be done about the stiff, bubbling orange cock glowing in front of Rhys’ eyes like a single candle alight in a dark room, then Rhys might as well find something he liked about the demon he was about to pleasure.  

“All right, kiddo, time to open up and get a taste of your own medicine.”

Jack’s fingers dug into Rhys’ jaw, but the young man popped open his mouth willingly, tongue lapping out over his bottom lip as he eagerly allowed the demon to shove its thick cock into his mouth.

It was softer than Rhys had anticipated, flesh slightly pliable as he nudged his tongue up against the shaft. It slid heavily into his mouth as Jack thrusted forward, his fingers winding again in Rhys’ hair as he pulled the boy in close.

The tip of Jack’s cock tickled the back of Rhys’ throat, its end hard and slicked from the glutinous fluid constantly drizzling from it. It tasted strange, with a slight spicy-sweetness Rhys would expect more from a seasonal pastry than a monster’s dick.

His nose practically brushed up against Jack’s shadowy crotch, the smell of burning leaves and petrichor flooding his senses as the demon rutted into his mouth, so much glowing liquid now dripping from the tip that it started to bubble out of Rhys’ full lips. The young man’s eyes rolled, his hands shakily grabbing for purchase against the demon’s thighs. He gagged for a moment when the tip of Jack’s cock forced its way into his throat but made a smooth recovery, swallowing tightly around the shaft as it wound its way deeper inside of him.  

He allowed the demon to use him, his body wide-open and slack as pleasure once more coiled up in his belly, his own cock hard and leaking as Jack fucked his face. He came moments before the creature did, his throat tightening around the cock as his teeth bit instinctively into the soft orange flesh. He let out a muffled whine as the tip of Jack’s dick burst deep in his throat, warm, thick fluid suddenly flooding into him. The shaft pulsed and writhed like a snake, squeezing Jack’s full release into his submissive vessel.

It was so, so much and yet Rhys drank greedily, his eyes fluttering closed in decadent pleasure as more and more of Jack’s cum pumped into his stomach, filling it to the brim as if he’d just binged on a sackful of Halloween candy. He nails raked down Jack’s thighs as he sucked harder against the demon’s cock, selfishly craving more of the demon’s ichor.

“Gluttonous little brat, if I give you any more you’re gonna burst,” Jack cackled as he pulled Rhys off of his cock, leaving the young man gasping hoarsely, glowing cum gushing out from between his lips and splattering onto the ground below. Rhys whimpered, shakily rubbing his stomach, now slightly rounded from the sheer amount of sweet release Jack had flooded him with. He felt heavy and obscene, his clothes tight around his swollen and beaten body as he sagged to the side, barely able to hold himself up with a shaky arm as he looked through swimming vision at Jack.

The demon had risen, his dripping cock retreating back into the folds of his shadowy body. The infernal, jagged grin had narrowed into something more amused as Jack observed him, and suddenly Rhys felt himself being whisked up into the air, his exhausted body held by wispy shadow mist as he was brought level with Jack’s mask.

Rhys was already well on his way to blacking out when Jack’s fingers grasped his chin, and when the demon yanked aside his mask and pressed white-hot, ethereal lips against Rhys’ own the young man passed out completely, a cackling voice echoing in his head.

“Lesson learned, huh kiddo?”

---

Rhys was grateful no one saw him laying half naked amongst the lot’s tall grass when he finally came to. The sky above him was cloudy and deep purple, the fading stars and the fresh smell of dew quickly telling him it was still early. He shot up in place, looking around him in a panic to make sure neither human nor….anything else was watching him. He was able to hike up his pants and stumble to his feet as he limped back to the sidewalk, retrieving his backpack and slinding it over his shoulders.

The house was gone, with no sign that it had ever been there. Rhys blushed as he flattened a hand down the front of his stomach, disturbed to find it still slightly swollen. His ass stung, smarting every time it rubbed up against the fabric of his pants.

He didn’t want to think about this, and yet with every step the night’s events rang through his body, dogging him even as he raced past the houses he’d vandalized the night before, without paying notice to their clean exteriors and undisturbed decor. He ran all the way to the bus stop, stopping only to dump all his pranking tools in the dumpster.

Rhys had never been more relieved to enter the small dorm room he shared with Vaughn, a calm washing over him as he stepped over the threshold and slung his backpack down onto the floor. He expected his room mate to be locked away in his room studying, or out taking a midterm, but to his surprise he found him seated at the counter of the tiny kitchenette, carving a pumpkin.

“Jeez, what happened to you?” Vaughn laughed, setting the serrated knife down at the counter and shaking his hands free of pumpkin guts. Rhys shook his head, a weak, suffering chuckle leaving his lips as he walked over to his friend.

“Fuck, bro, you wouldn’t believe me even if I told you….what’s up with this? Getting into the holiday spirit after all, huh?” Rhys smirked as he grabbed the stem of the pumpkin, turning it around to face him.

A familiar, scarred grin leered back up at him, hollow eyes fiendish and piercing into the young man’s heart. He froze, expression a mask of horror.

“Rhys? Rhys?”

Vaughn had only a split second to jump and catch his friend as he fainted.