Tell others about this story! Over 300 choices.“Grandpa, tell me a scary story.”
It was bedtime, and Timmy sat huddled under the covers as his grandfather tucked him in. It might not be the best time for a scary story, Grandpa thought. There were nightmares to be had in a darkened bedroom such as this. But the boy so loved his stories.
“I don’t want you to have bad dreams,” Grandpa said.
“I won’t have bad dreams. I promise.”
“That’s something you can’t promise. Bad dreams happen whether we want them to or not.”
“But tomorrow’s Halloween and you always tell me a story at Halloween.”
Grandpa knew when he was licked. But what story could he tell? It had to be new. It had to be about Halloween. But above all, it had to be scary. Looking around the room, Grandpa’s eyes found the pumpkin sitting on Timmy’s windowsill. Its face had been carved into a smiling Jack-O-Lantern, its insides dark because Timmy wasn’t allowed to have any candles in his room.
“Have you ever heard the tale of Stingy Jack?”
“No.”
“Well then. Lean back, my boy. If it’s a scary story you want, a scary story you shall get.”
* * * *
A long time ago, in the far off village of Withered Branch, there lived a man named Jack. The other villagers knew him well for he had a nasty reputation as a drunkard and a cheat. He was tight with his money, would never give to others, and could talk a bargain out of even the most stoic shopkeepers and pub owners.
On one dark evening, Jack found himself in the local pub, thirsty for a glass of ale. He had no money, of course, but that never stopped Jack.
At the end of the bar sat a lone stranger. He was a dark sort of man, dressed in a black cloak and hat as if to shield himself from the hard Irish rains. The man was keeping to himself, sipping from a mug of brew. Jack made his way to the stranger and perched himself on the seat next to him.
“How are ye, sir, on this here fine evening?”
The man said nothing.
“Cat got ye tongue, boy’o?”
Again the man kept silent.
Shrugging, Jack turned from the stranger to address the pub owner. “Bar keep. One of your finest ales, please.”
“You know the rules, Jack. Cash only.”
“Me credits always been good before.”
“Not anymore, Jack. No money. No ale.” The pub owner turned and walked away.
“Why, the Saints preserve us,” Jack declared. He turned to the stranger. “Can ye believe such a thing? What strange Devilry is at work here that a thirsty man can’t even get a pint of drink on a cold night such as this?”
“Devilry?” the stranger finally said.
“Aye,” Jack answered. “It’s the work of Satan, I tell ye.”
“Is that so?” the stranger asked. “Tell me. Why would the lord of the underworld conspire to keep a fine gentleman such as you from enjoying his nightly ale?”
Perfect, Jack thought. He had the stranger talking. Now it was only a matter of time before he would taste the sweet joy of drink at this man’s expense.
“That’s the way of his trickery,” Jack lamented. “The devil will conspire to keep the thing ye most desire from ye in the hopes that ye sell your soul in exchange for that very thing. Like myself, for instance. I’m not asking for much, just a tiny taste of ale to warm me bones on this cool dark evening. But Satan won’t allow it. I’ll have to sell me soul, I tell ye.”
“And would you?” the stranger asked.
“Would I what?”
“Would you sell your soul for a glass of ale?”
“At this moment, I believe I would. But I don’t see any buyers around here.”
The stranger smiled, downed his last swallow, and regarded Jack with a sly expression. “Would you consider selling your soul to me for a good drink?”
Jack had the stranger right where he wanted him. Obviously the stranger was the superstitious type who gave into believing in nonsensical ideas. This was going to be easy.
“Why, sir,” Jack declared. “If ye were in the market for a soul, I believe that ye would find mine in excellent condition, and quite the bargain. Shall we say, a full flagon of ale?”
Just then, the stranger produced a sheet of paper. On it there were markings in a language Jack did not recognize. At the bottom was a dotted line. “If you’re a man of your convictions, then sign here and the ale shall be yours.”
Taking the man’s pen, Jack signed his best signature.
Suddenly, as if out of nowhere, a full flagon of ale appeared.
“Drink up,” the stranger urged.
And drink Jack did.
* * * *
He couldn’t remember how he got home, but the next morning he remembered the pub, and the stranger, and the drink quite clearly, for his head felt like a drummer’s kettle, thumping and pounding with a colossal ache.
The knock at his cabin door felt amplified tenfold. Flinging it open, Jack stood tall in the threshold, ready to repel whoever dared disturb his mighty hangover.
It was the stranger from the night before. Jack instantly knew that something was amiss. The stranger had tracked him down. Why? Perhaps he had come to his senses and realized that he had been duped. Perhaps he was here to demand his money back for the ale Jack had drank last night.
“Sir, I think I know why ye are here. But before ye speak, I think it me duty to say that we had a legal contract. Ye agreed to supply me with ale in exchange for me soul. Now, I understand that ye may have been tipsy last night, and in no condition to barter a sensible deal, but that is not me problem. It’s not me fault if ye agreed to purchase something that didn’t exist.”
“On the contrary,” the stranger said. “I’m not here to argue the validity of our deal. You bought your ale fair. But I must disagree with one thing; your soul does exist. And now it is mine.”
Just then, the winds came out of the sky and the clouds blackened. The stranger, once normal in appearance, began to grow horns, and sharpened teeth, and red skin. His tongue, like a serpent’s, slithered and curled over his now grotesque mouth.
“Saints preserve us,” Jack muttered. “Ye are….”
“Lucifer. The Devil. Satan. Take your pick.”
“But it can’t be.”
“Oh but it is. I came here today to remind you of our contract. I upheld my end of the bargain. Now I own your soul.”
Panicked, Jack suddenly realized the gravity of the situation. When trying to trick the stranger, the stranger had, in fact, tricked him. Not believing in the existence of a soul, Jack had sold it off for a mere pint of drink.
“Enjoy this life,” the devil said. “For when it’s over, a new one awaits.”
As he turned to leave, Jack spoke up. “Wait. Don’t leave. Not yet.” Trying hard to hide the desperation in his voice, Jack continued. “If ye think me soul is valuable, I know of something else that is far more precious.”
“Like what?”
“Ye don’t expect me to just give it away now, do ye? Like me soul, this particular item will come with a price. But I’ll tell ye what I’ll do. I’ll show ye the item, and then ye can make me an offer. How’s that sound?”
The devil, always searching for a bargain, agreed. “Where is it?”
“I like to keep me valuables far from prying eyes. Ye see that tree next to ye? It’s up at the very top. All ye have to do is climb up there and look.”
The devil did as Jack suggested and climbed the tree to the very top. But when he got there, he found nothing. “What is this? There’s nothing up here.”
In a flash, Jack whipped out his trusty pocket knife and carved a cross in the bark of the tree. Furious, the devil shrieked his contempt at Jack, but there was little else he could do. With the cross carved into the tree, the devil was stuck and could not come down.
“Now,” Jack said. “I’ll make ye a new deal. Ye tear up our previous contract and agree to never visit me again and I will remove this cross and let ye down.”
The devil’s anger was enormous and he cursed Jack for his trickery. Never in his existence had anyone fooled him. But in the end, he knew that Jack had won. Taking the contract from his pocket, the devil set it aflame.
When Jack was sure of his success, he took his knife and scraped away the cross.
When the devil descended from the tree, he stood before Jack and acknowledged that he had been bested. “But hear this,” the devil warned. “A day will come when you’ll regret your transgressions, Stingy Jack.”
With nothing more, the devil departed, leaving the skies to clear, and the winds to fade, and Jack to revel in his victory.
* * * *
“Did Jack live happily ever after?” Timmy asked.
“No,” Grandpa assured him. “Jack did not. He lived the rest of his life having never met the devil again. But after he died, and found himself before the gates of Heaven, God would not let him in. For his wicked, sinful life, Jack was cast away from Heaven, never to return. With nowhere else to go, Jack’s soul descended into hell. But when he got to the underworld, he found that he wasn’t welcome there either. For his trickery, the devil cursed him to walk the earth in continual darkness for all time. To light his way, the devil gave him a single burning ember, then banished him to an endless night on earth.
With only his ember to guide him, Jack roamed the night, alone, lost. Needing something to carry his ember in, he found a hollowed out turnip and carried it like a lantern. When that turnip eventually rotted away, he found another, and then another. In time, his wandering took him far from his native land. He wandered many lands, and crossed many seas, and eventually made it to this country where he found a new fruit that grew only here: a pumpkin. It was the perfect lantern for his ember. In time, the people stopped referring to him as Stingy Jack and began calling him Jack-of-the-lantern. Or as we know it…”
“Jack-O-Lantern,” Timmy finished.
“That’s right.”
Timmy turned to the carved out pumpkin on his windowsill, and regarded it with wide-eyed wonder.
“They say that Jack is still out there, roaming the night, carrying his ember in a hollowed out pumpkin. It’s believed that on every Halloween, he chooses a new pumpkin to be his lantern. Who knows? Maybe this Halloween, he’ll choose yours.”
With the story over, Grandpa said goodnight and turned off the lights. Alone, Timmy lay in his bed, the covers up to his chin, watching the windowsill. He could still see the pumpkin there, its outline clear in the moonlight.
In time, Timmy fell asleep. In his dreams, he was haunted by the image of a dark stranger walking down a lonely trail, carrying a carved out pumpkin with a single burning ember inside to light the way. As he tossed and turned in his sleep, he could see the outline of his own pumpkin, its carved out faced suddenly glowing from a light within.
When he woke up that morning, it was Halloween.
And his pumpkin was gone…
The End
George Ebey is the author of the novels Broken Clock, The Red Bag, Widowfield, and the short story collection, Dimensions: Tales of Suspense.
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