The Caretaker

A Halloween Tale


This is a work of FICTION for ADULTS only.  Do NOT read this if you are under 18 or if you are not an adult according to the laws of your State or Country.  Do NOT read this if you are easily offended or if you are not interested in fantasies involving young boys.  This file contains sexually EXPLICIT material.

The author does not condone any of the acts in this file.  

This story was not written to advocate sexual activity with minors. 

Please support free speech and stop censorship.

Codes: (m/b - oral, anal)


" Masquerade, masquerade. Grab your mask and don't be late. Get out get out well disguised. Heat and fever in the air tonight. " -H


   Shall we begin boys and girls? Cum closer and immerse yourself in the tale of a lucky boy named Luke. A kid just like you maybe, who loved Halloween because of all the goodies he got for free!

   And so, on that special evening... 

   ...his bag was heavy with candy. It had been quite a fruitful jaunt! Luke was happy about that, as would any other easy-going pre-teen boy with a sweet tooth! Yet he trudged on the sidewalk with a worried expression crumpling his angular face.

   The streets were getting dark. Most folks had turned off the lights on their houses to indicate the end of the Halloween celebration. It was as if everybody shut out the rest of the world at the same time. Here and there, a lonely Jack-O'-Lantern stared at him with its candlelit smile.

   Luke looked at the morbid decorations differently now that the thrill of ringing people's doorbells was over. Taking a shortcut on a deserted stretch of road, he mused that a small town under the cloak of an autumn evening could be quite spooky when you're alone... If only his buddy Steven had not been ill and accompanied him trick-or-treating, things would seem less scary... His heart thumped faster as he scanned the area praying to spot other kids.

   There were none. 

   From out of nowhere, a cold wind started whistling an eerie tune in his ear. He walked faster, his little fingers tightening on the straps of the oversized bag. 

   Suddenly, a black cat dashed in front of him. Luke inhaled and jumped back, nearly losing control of his bladder. The slick feline with shiny yellow eyes crouched down to hiss menacingly.

   "Arh, you're only a stupid kitty," Luke chuckled, welcoming the return of his composure. He kicked in the direction of the cat, banishing the four-legged beast and mocking his irrational fear. After all, he was eleven-years-old now! Not a little kid anymore! Besides he should be the frightening one on the account of his skeleton costume! 

   It was so neat and creepy! 

   The two-piece outfit made of black spandex enveloped his body entirely like a glove. Only the fluorescent white bones designs and the plastic skull mask glowed in the dark. The fact that he was skinny really helped to give him the appearance of a child's skeleton walking in the night! The disguise was without a doubt the coolest one! A perfect choice! 

   However, he couldn't say it had been love at first sight... 

   Initially, when his mom had purchased the skeleton suit on sale, Luke hated it. It was so snug that he couldn't possibly wear any underwear. The idea that everyone would see the bulge of his privates bothered him. But he had reasoned himself and figured that if he jerked off prior to putting it on, he could at least avoid popping an embarrassing stiffy. 

   So, an hour before going out, he bounced under the warm spray of the shower to play with his balls and rub his butt. He pulled on his rigid little pecker fast and steady, aroused by the anticipation of being naked underneath the tight fabric. The slippery friction of the soap summoned increasingly more violent doses of pleasure. His fingers flew along the sturdy erection. 

   Much to his surprise, the resulting orgasmic burst of bliss was unlike any other in the past, causing him to yip out loud. In the end, he had looked down at his penis just in time to catch three tiny globs of boy juice shoot out of it so powerfully that they hit a tile on the wall! 

   Of course, that enjoyable moment was the last thing on Luke's mind as he passed in front the gloomy cemetery of Mellovale. He'd often played there after school. But in the darkness the place looked ominous. 

   Visions of ghouls and zombies flooded his head. A black crow perched on the iron rail of the gates croaked loudly seemingly inviting him to visit its gruesome domain. 

   Luke glanced at the foggy pathways between the burial mounds, thinking he could prove to himself he wasn't a coward if he took a stroll in there. Wouldn't Steven be impressed? And there was something he'd wanted to do for a long time too... Something wickedly fun! 

   The crow flew away while he wiped his sweaty palms on his thighs bracing himself to face his fear. Gathering his courage, he entered the graveyard hesitantly, looking all around at the macabre scenery. The bare trees were grey under the moonlight. They all looked dead. He pictured their branches coming down on him, like gnarled and twisted fingers reaching for his throat. He ran. 

   His short legs carried him to the bronze cherubs adorning a pedestal. The motionless group stood on one foot looking up at the sky. With no sun shining on them, they were sinister. He wondered again why anyone would want to sculpt statues of chubby toddlers with wings? Sometimes, during the winter, teenagers used wet snow to turn them into obscene little figures. Luke chuckled remembering the big white boners sticking up between their podgy legs. 

   Still grinning behind his mask, he trotted further, reading the names of the dead aloud while a breeze scattered leaves amidst his footsteps. Some of the tombstones had eroded. Luke hoped it wasn't the case for Virginia Lanston's monument. The rumor amongst his schoolmates was that if you made a wish while peeing on her grave, it would come true the next day. They had repeated that on many occasions. So it couldn't be a lie? 

   Thankfully, her gravestone remained in good condition. When Luke found it, he quickly pulled down the front of his spandex pants, releasing his limp weenie from the confining fabric. He retracted the foreskin to expose the little pink knob and mumbled "Sorry, lady." as the arch of urine landed on the slab of concrete marking her resting place. 

   The ritual was so silly that he almost forgot to make a wish. Watching the stream of steamy pee dwindle, he recalled the purpose of his visit. 

   "Oh shit! I wish - I wish I were RICH!" he shouted.

   "Is that so?" someone said behind him with a cheerful voice.

   Luke hurried to pack his dick and balls back in his pants. He turned on a dime to face the approaching man. The tall stranger looked younger than his dad, perhaps in his early thirties. He was handsome like the invincible heroes Luke had seen in so many action movies. Despite the dirty denim overalls, a certain charm emanated from him. Not enough to convince Luke that he could let his guards down. 

   "STAY THERE or, or I'm gonna SCREAM," he barked, holding his bag of candy like a shield. 

   "Don't be scared," the man said. "My name is Gilbert. I'm the caretaker here, you know, the groundskeeper? I mow the lawn and make sure everything is tidy. What are you doing here in the dark? Pissing on Virginia's grave I suspect?" 

   Luke nodded sheepishly, still in a defensive stance. 

   "I bet you don't even know how this idiotic tale came about?" the man inquired.

   "Not really," said Luke. 

   "It doesn't surprise me," the man shook his head. "It's pretty grotesque. You see, Virginia Lanston died of a mysterious illness right after she exchanged her wedding vows. They buried her here three days later. Her husband - who was madly in love by the way - became insane. One night, he dug her up and consumed their union. You know what that means, huh?" Gilbert looked down with a sly grin. "Yep, he fucked a corpse!" 

   "Whoa, that's sooo sick!" Luke tooted gleefully, stamping a foot on the ground. 

   "Sick indeed... Over the years the legend was transformed so much by people wanting to preserve Virginia's dignity that she is now perceived as a wish granting saint..." 

   "How come you know all this, Mr. Gilbert?" 

   "Oh, I know everything about this cemetery," the man sighed, trailing off into an awkward silence. He regained his zest after an instant and clapped his hands. "Hey, how about you take off that mask so I can see who I'm talking to?" 

   "Erh, okay," Luke said, removing it carefully and storing it in his bag. 

   "There you go! I knew you'd be pretty," the man remarked. "It's a crying shame you have to hide this cute face at Halloween." 

   Luke blushed brightly and looked away. It was the first time a grownup had uttered a compliment about his physical appearance. Oh, his mom always reminded him how gorgeous he was. But it was his mom... 

   In front of a mirror, Luke considered himself 'plain'. His eyes were brown. His head seemed like a big balloon above that slim neck. On top of it, the mop of blond hair never stayed put even though he combed it regularly. And the horrendous freckles across his nose were like dirt stains in his opinion. 

   "Come with me, I'll show you where wishes come true." Gilbert announced. "Virginia can't realize them. If one of your friends says so, tell him it's a big pile of bullshit!" 

   "For real?" Luke piped, jogging behind the wise caretaker. 

   "Yes. There's only one place where wishes come true." Gilbert reasserted. "You came at the right time because it only works for children on Halloween. How old are you?" 


   "Hmm, back where I come from, you'd be almost a man! But I think it's gonna be fine." 

   Side by side, the improbable couple walked deeper into the vast cemetery. They reached a wooden shack and the man opened the door. "Come in, I live here," he gestured. 

   Luke hesitated an instant. The caretaker seemed like a nice enough adult to merit his trust. And he knew he would regret it for the rest of his life if he didn't grasp the opportunity to have his wish come true. Strangely, almost on their own, his feet stepped inside the modest home. 

    The cozy dwelling was dimly lit by a couple of gas lamps. On one side, there were a few pieces of furniture and a bed. On the other, a fire burned in a cast iron stove. The intense heat warmed Luke's frozen toes. He dropped his bag on a shabby table and took a seat in the only chair. 

   "In here, your wish can come true," said Gilbert. 

   "In here?" 

   "I know, it's not all that creepy now, but a murder happened on this spot a long time ago. Do you wanna hear the story?" 

   "Yeah, sure!" Luke said, chewing his index finger. 

   "It happened in the late 1700s. There used to be a house right where you are sitting now. A painter lived in it. And he loved little boys very much. Whenever they came by, he gave them candy and made toys for them. With time, a few grew fond of the friendly man and agreed to pose for his portraits...even though they had to be naked..." 

   "Naked!" Luke giggled. "Why is that?" 

   "He thought they were the most beautiful creatures in the world when they had no clothes on. So he only painted nude little boys." 

   "That's weird!" 

   "A lot people thought so too. They started calling him a warlock. They said he was stealing the souls of the children each time he painted one. On Halloween night, a group of villagers disguised themselves to commit a most heinous crime. They tied the painter to a beam inside his house and set fire to it. He burned to death and all his paintings were destroyed." 

   Luke froze, startled by the monstrous conclusion of the tale. "And, and there's a - a curse?" he asked. 

   "No, he wasn't evil," Gilbert smirked. "You see the rug on the floor? This is exactly where he died. For all the little boys who come here on Halloween, the spirit of the painter will grant them their wish. You still want to be rich, right?" 

   "YES!" Luke said, rising at once, bolting to the spot his host had pointed. 

   "Hold on now. It's not that easy," Gilbert laughed. "There are things you need to do... First, you have to take your clothes off." 

   "All my clothes?" Luke demanded, his shoulders slumping. 

   "Yes, don't tell me you're a prude?" the man frowned. "You have no reason to be shy. I'm sure the spirit of the painter will like you." 

    Luke chewed his finger again. Other kids had done this? There was nothing to worry about, right? And he was no prune! 

   "Are you sure?" he asked.. 

   "Hey, rules are rules and you have to follow them," Gilbert smiled. 

   "Okay, if if I have to... I'll do it!" Luke said aloud to embolden himself. 

   Turning his back to the man, he began to undress. The sound of buttons unsnapping clicked behind him, but he was too busy to give it any attention. Off came his top and his black runners. The tight spandex pants gave him trouble. As he tugged on them to free his legs, his heart raced. He was naked now! Alone! In a cemetery! The stranger could see his butt! 

   When he pivoted, a gasp escaped his lips.

   The caretaker was sitting on the edge of the bed stark naked as well. Between his muscular thighs, a fat penis with an exposed plump head dangled over two large hairy testicles. Suddenly very conscious of his own nudity, Luke bowed his head, looking down at his pale frail body, at his flaccid appendage hanging from the hairless slope below his bellybutton. His hands moved swiftly to cover the evidence of his immaturity. 

   "You are a beautiful boy," Gilbert stated softly. 

   Luke blushed again, fidgeting in front of the husky adult. "What do I hafta do now?" The question resounded in the shack, the high-pitched echo of it almost pleading. 

   "I'll show you," Gilbert said. "Look at me." 

   Luke raised his chin and stared into the man's deep blue eyes. A series of tingles tickled his bare skin. Something odd was happening...

   When the caretaker advanced to cuddle him, his legs turned into jell-o. He felt the heat of the wiry body blanketing him. Large hands roamed all over his forms and his dick twitched. Gilbert's pectorals were at the level of his mouth. For some reason, Luke felt compelled to nibble the man's nipple while his buttocks were kneaded. He suckled and chewed the rubbery nub. Then his own little hands extended to grab the broad shoulders, to escalate the front of the adult and bask in his warm virile embrace. 

   "Hold me," he whispered. 

   Gilbert cradled him gently and lowered him onto the rug. The next moment, their limbs were tangled up and their lips locked in a kiss. Again, the man's hands caressed him, in a way no one had ever touched him before. Everything was happening so fast! Luke pondered nervously what he was doing or why? Was this sex? Even in his wildest fantasies he had never pictured himself doing it with a big hairy stranger! 

   By then, Gilbert had grasped one of his ankles and pinned his dainty leg against his chest. 

   "I'm feeling weird," Luke said, looking down quizzically at his crotch where the man's energetic tongue licked his nutsac. A voice inside his head told him to leave, flee from the attractive fellow's seductive pull. But the brief lapse of reason vanished as fast as it came, replaced by a peaceful vertigo. 

   "You have to let go." Gilbert said. "Surrender yourself. I promise you'll have fun and be very rich." 

   "Okay," Luke nodded. 

   "Play with your dick. I bet you love doing that. It's all stiff and throbbing. Isn't it?" 

   Luke produced a shy grin, gripping his tender organ with two fingers. Meanwhile, Gilbert's tongue migrated lower and swirled in the cleft of his butt. Ohhhh! The big wet tongue wiggled and poked at his poop hole. It stayed there teasing the puckered ring again and again. Luke titled his head back, drowning in the new sensations. 

   "Do you like it when I lick your butt hole?" Gilbert asked. 

   "Yessss," Luke answered, panting. 

   "How about this?" Gilbert said, diving onto his small erection. 

   Luke giggled then flinched from the surge of bliss. The man's lips slid up and down his boner, up and down, up and down. They paused at the top to stimulate the small mushroom head. Luke watched the tip of the tongue flicking at his glans and let out a plaintive moan. 

   "Ooohhh this feels nice!" he sang. 

   The man's mouth engulfed his little dick again. His toes curled up and his thighs quivered. He grabbed himself under the knee, granting the stranger access to do whatever he pleased with his genitals, all the time watching, and feeling the pleasure become unbearable. 

   "Uhhh, I'm gonna cum," he whimpered. 

   "Not yet," Gilbert shifted sideways, head over his taut boyish belly. 

   Luke's focus alternated between his crotch where the man's tongue licked softly his boner and the unavoidable engorged manhood pointing at his chin. The eight inches of hard flesh looked like a giant ballpark frank. Luke felt the urge to touch it, put it in his mouth and taste it. 

   At once, the animalistic impulse got the best of him and he pounced. His small fist wrapped around the hot flesh, his lips kissed along the length of the bloated tube. He opened wide and stuffed a great chunk of the meaty stick in his mouth, immediately slurping the leaking juices. 

   "Uhhhh," Gilbert groaned. "Yessss, suck my cock! That's it. You can be a lil' whore tonight. No one's gonna know. Go ahead, suck that big cock all you want." 

   Luke grunted, bobbing his blond head faster. He had never felt so naughty and excited. The immense piece of meat stretched his lips but he continued to siphon it, eyeing the patch of curly dark pubes. 

   After a few minutes, he ran his tongue on the underside of the member to the top of the head and let it dance on the silky smoothness, collecting the pearls of liquid trickling out of the slit. Once in a while, his eyes veered to Gilbert's face to confirm he was doing it right. 

   "Ohhhh, you're driving me nuts! That's it boy! Come on, suck that cock," Gilbert said, slipping a hand behind the nape of his neck and pulling his mouth onto the steely erection. 

   Luke smiled and leaned forward letting the man abuse his mouth at a brisk pace. The knob of the hard rod banged against the back of this throat. Drool seeped from his lips and oozed down his chin. He grabbed Gilbert's huge balls in the palm of his hand and thrust his face to meet the upward lunges. Suddenly, the big cock popped out. Luke licked his gummy lips looking up with glazed eyes. 

   "You're into now, huh? Do you know what a man does to a horny boy like you?" Gilbert asked, flaunting his glistening manhood. 

   "He fucks him!" Luke heard himself say, his eyes widening. 

   "Yes. You wanna feel my cock inside you, huh? I bet you want it up that tight lil' ass of yours? C'mon, turn around."

   Luke crawled on all fours over the magical rug like a restless dog. The man kneeled behind him and smacked his buns. "You have a great ass, boy!" he said, smacking it again. "I bet you don't even know how much it's worth!" 

   "Noooo," Luke whined, feeling his buttocks parted and the thick meat rub in the crack. The large head grazed his poop hole. The pressure intensified there. He winced as the tight ring of his anus yielded painfully to the intrusion. 

   "Uhhh, it's too big!" 

   "Just relax my angel," Gilbert said. 

   With that, Luke felt the scorching rush of the erection pierce into him. His body stiffened right away. A shriek soared out of his lungs. The man's hands grasped his waist and the big cock slipped further inside him. 

   "Orhhh, it's been so long!" he heard the man cry out and immediately thrust into his bottom. 

   For several minutes, Luke cringed, getting accustomed to the mass lodged deep inside his guts. Usually that channel was a one-way street. It seemed like the huge penis would split him in two! He bit his lower lip. The rhythmic ploughing slowly numbed his brain. The hard manhood slid back and forth, in and out of his butt, again and again. His own little dick, which had shrivelled, stiffened again. 

   "Unnnghhh, I can feel it good, unnggh, in my butt!" he said. 

   "Yes, you will remember this Halloween night!" Gilbert exclaimed, fucking him at a faster pace. 

   Luke tried to find something to hold on to, but there was nothing there. The man started shaking him with powerful jabs. The brutal outward strokes made him collapse forward then the hands dragged him back onto the erection. 

   "Annggh!" Luke wailed each time the caretaker rammed his hard-on into him. "Annngh Annggh!" 

   "Ohhhhh, I knew you could take that cock up your butt," Gilbert said. "You're no sissy boy? Are you?" 

   "Nooo," Luke said shaking his blond head. The man's hands moved to grip his shoulders. The big cock slammed hard inside him, its wide shaft straining his bum hole even more. He pulled on his stiff pecker, faltering on one arm, his knees pinned to the ground supporting the weight of the man pounding his butt. 

   "Annnngh! Annggh!" he wailed again, fisting his boner. 

   The repetitive stabbing was relentless. It turned into sheer ferocity. Gilbert's heavy balls slapped against his behind. 

   "ARRGGGGH! AARRGH!!" Luke yelled, his small bottom banged mercilessly by the hips of the man. His entire body was rattling like an old school bus. 

   "Ohhh YESS! OH FUCK YES!" Gilbert screamed. "Take it to the hilt! YESS Oh FUCK YES!"

   "ARGHH! Pleeze, yes ARGGH! Pleeze" Luke babbled, entranced by the violent ravaging of his defeated bum hole. Jolts of pleasure shocked the defenseless orifice, the same for his testicles. A big one swelled up his boner and tiny jets of milky jizz squirted out of it. The man stopped fucking him while he came. His vision blurred and he sobbed out of joy, paralysed by his orgasm with the big cock still planted firmly inside his rectum. 

   "Unnnngh! Unngh! Unggh! Unnnnggghhhhh!" he whined. 

   "Yes, that's it, savour it," Gilbert repeated. 

   Luke shivered, feeling the pleasure rise and descend, fade and go away. He glanced back at the man, catching his breath. 

   "You got a good cum there," Gilbert said, pulling out of him carefully. 

   Luke grinned shyly and sat on his heels, still dazed by the intensity of the copulation. His fingertips furrowed in the crack of his butt to rub out the itch of his sore anus. "Ouch!" He could easily stick four of them in there! 

   "Don't worry about that," Gilbert reassured him. "It happens the first time. Tomorrow that cute lil' poop hole will be good as new." 

   "I shot a lot of jizz this time," Luke smiled and looked down at his softening pecker. 

   "You did, huh. But there's one last thing you need to do to get your wish. Open your mouth real wide." 

   Luke obeyed the request. The man stepped closer and began masturbating in front of his gaping mouth. He stared intently at the bulbous head of the organ. It was purple and the pee hole open. The first explosion of cum splashed on his palate. Then the thick white ropes erupted randomly around his lips. 

   Some of the spurts shot up to his forehead and he closed his eyes. It seemed like the blasts of cream would never end. Eyelids shut tight; he felt his face get covered with the sticky sauce. And his mouth filled up completely. When the shower ceased, Luke heard the man rejoice. 

   "Now, drink up! Mmm. Yes, eat that load." 

   Luke swallowed the wad merrily in one big gulp, without as much as a slight grimace. For sure, his wish had to come true now! He wiped the gooey mess off his face and opened his eyes, finding himself alone. 

   An icy breeze caressed his nude body and the stench of decay wafted up his nostrils. Around him jagged wooden planks projected out of the ground where the shack had been. He stared up at the starlit sky then down again at the ruins surrounding him. His Halloween costume lay on a patch of undergrowth. 

   "Mr. Gilbert?" he called, looking all about. "Where are you?" 

   No one answered. 

   Realizing the horrible seriousness of the situation, he scurried to put his clothes back on, grab his bag of candy and go home. Tears streamed down his freckled face as he ran in the empty streets of the sleeping small town. The sharp stinging pain of his violated asshole a constant reminder of how stupid he had been. 

   When he walked inside the house, his parents were waiting there, arms crossed. 

   "Where have you been? Do you know what time it is? It's after midnight!" his mom screamed. "That's it! You're never going trick-or-treat alone ever again!" 

   Luke bowed his head, trembling, unable to even consider fabricating a plausible explanation. 

   "What happened out there?" his dad snickered to ease the tension. "You look like you've seen a Halloween ghost!" 

   Before Luke could say anything, his mom screamed again. "Go to bed, now! I'm so angry, I can't deal with this!" 

* * *

   The next morning, Luke woke up with a piss boner tenting the front of his pajamas pants. 

   He jumped out of bed. 

   Instead of going to the bathroom to relieve the urge, his bare feet walked to the bag of candy resting on the floor. A pressing task was at hand. He needed to hide the good stuff before his mom confiscated it! All the chocolate bars and the Tootsie rolls. 

   Turning the bag over, eyes sparkling, he watched the content fall on the floor. An object made a loud thud as it landed. 

   Luke focused on the unexpected find amidst the gumballs, caramels and other candy. The small painting with an ornate frame was of a blond boy. His head shone in the middle of an angelic aura. The way the light hit his bare shoulders and accented the delicate features of his face made it seem like he was three-dimensional, almost holographic. Strangely, the model looked very much like him. 

   Luke's eyes shifted to the small golden plaque nailed at the bottom. It read 'The portrait of Luke'. 

   Shivers ran up his spine. The work of art brought back memories of the previous night's adventure with the caretaker that he'd already chosen to dismiss in a corner of his mind. And he failed to see how it meant he was rich? 

    He scorned at the painting. 

   However, as much as he wanted to destroy it with his fists, he couldn't find the will to do so. The hypnotic beauty of the boy mesmerized him. Taking to his feet, he ambled to the closet and put it in the box of dusty board games they never played with anymore, where his mom wouldn't think to snoop... 



   It would take twenty years before Luke, now a man, stumbled upon the odd gift he'd received as child. 

   "Get rid of that junk," his wife said when he showed it to her. "I can't believe you've kept this portrait of a little boy all those years. Don't you think that's perverted?" 

   Luke agreed it was time to part ways with the unusual objet d'art, to clear his mind of the repressed secret he'd carried for so long, achieving closure in a way. 

   Out of curiosity, he went to an appraiser, just to see if it was worth anything. 

   As it turned out, it was the sole intact creation of the colonial painter Gilbert Sutcliffe who died in 1798. There were some charred remnants of his other works in the warehouse of a museum, but Luke owned the only complete piece of the elusive artist. 

   Upon the recommendation of the appraiser, Luke submitted it for auction at Sotheby's. 

   And so, on October 31st, he sat in the New York auditorium waiting for the bids on his lot. It was with a pleasant shock that he heard the ludicrous amounts at the opening of the sale. Each new bid that the auctioneer shouted brought wave after wave of excitement, almost of a sexual nature. 

   In the end, his lips were contorted into a crooked grin. 

   'The portrait of Luke' sold for 1.8 million dollars. 


THE END     

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