This standalone story is based on the English fairy tale Jack and the Beanstalk as well as the 2009 film adaptation written by Flip Kobler and Cindy Marcus, starring Cloin Ford in the lead role. It's also based on the 2014 film version of Stephen Sondheim's 1986 Broadway musical Into the Woods, with Daniel Huttlestone as Jack.
I was inspired by psychologist Bruno Bettleheim's Freudian analysis of the fairy tale in his book The Uses of Enchantment (1976) to write this story, as it explains how the story (particularly the symbolism of the beanstalk) illustrates a boy's emergence into sexuality and adulthood. I just decided to add a tentacle erotica theme to it.
I own no rights to the original tale or any of the film versions. If it is not permitted to read any fiction of this type where you are, stop now.
Thank you.
Questions/comments: JamesJenkins4253@proton.me
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Jack & the Bawdy Beanstalk © James Jenkins 2023
Jack stared at his candlelit ceiling, upset, and bored. The chorus of nightly forest dwellers sung on, some kind of late-night lullaby urging him to call in right now and forget how his mother scolded him earlier, and the sound of the flowing stream by their house where she tossed the magic beans just audible enough to be hurtful. The 12 nearly 13-year-old sighed and rolled onto his side to stare at the wall, glancing at his handmade clock to check the time. Nearly three in the morning. He already knew the next day trying to make money at the market was going to be hard, even if he were to fall asleep now. Swiftly an idea came to him, though. If he was going to go hungry anyway, why not go out for a bit and find something worth his mother slapping him in the head about? Jack wondered if his friend, Red, would be at home. Without even thinking if he'd be disturbing her sleep first, he slipped from bed and headed for the window. Fortunately, his room was a safe drop to a hay bale outside. Sneaking out was exactly what that window was meant for!
The sly youth climbed through the window into the warm moonlit night, struggling a bit to get his legs to fit. While it might have been ideal for sneaking out, but he learned from past attempts how not to do it.
The walk to Red Riding Hood's house was relatively short, but a small thicket of trees separated the two and it was much faster to just go through them than around them. He'd even braved through the woods in the daylight and used his late father's axe to cut a small path through them so the prickly weeds wouldn't be able to scratch his skin as badly. Jack was brimming with anticipation, his heart thrummed almost unrestrained rapidly in his chest as he navigated his way over the muddy unfirm ground. In his head, he then recalled. It was Red, she'd told him yesterday she wasn't going to be back from her granny's house for another few days and that she'd visit him once she returned home. Jack's heart sunk and despondency fell upon him in a cruel gust. He was already halfway to his house, too. Yet an idea nudged the back of his mind. Red's dear friend Jillian Squarejaw would be home, and he'd not overlooked how she had a habit of staring at him when he was visiting. The lean blonde grinned and at the same time felt foolish for not having thought of it before. Ben and Jack had a difficult, on again off again relationship that was riddled with infidelity, mostly on Ben's part, and so he thought of it as a bit of payback. What goes around comes around.
The bold boy stuck his axe back in his pocket and realized he was a little lost. He'd been so immersed in his fantasies he hadn't been paying attention to where he was going, and now he couldn't see the path or his house anymore. He sighed despondently and shone a shard of reflective mirror at the dirt path, retracing his steps as well as he could remember. Just as tears were beginning to sting the corners of his eyes and fear coursed up on him, a gripping pain in his instep had him fall to the dirt-covered ground. He'd been caught on a stray tree root, and it was already turning black. The boy really started to cry then, loud, and panicked sobs that only someone who was sure they suffered greatly could make. Not fitting a man? Perhaps, but Jack was a sensitive boy after all.
Drawing himself onto his hands and knees with a strained grunt, only to feel something frigid wrap itself around his movable instep. Jack howled and defiantly kicked his leg, but with a sudden forceful tug he was being dragged along the ground on his front, his black-gray striped shirt was rolling itself up over his head in the fight and in a hopeless attempt to keep his dexterity he jostled out of it and tried to reach down and punch at whatever had him. The unseen attacker on his instep was smooth and felt sort of like an enormous root, but no amount of scratching his nails into it seemed to harm it. Jack screamed for help and thrashed, but there was nothing he could do as it pulled him toward a hollow at the base of the beanstalk's trunk, and then into its depths.
No amount of kicking and screaming helped, and it ended up making his stinging joint feel like boiling water. Jack wept as the tendril dangled him as a slain rabbit in the air, the sound of slickly moving...things moving under the disturbed earth biting his ears. A few seconds later another tentacle came along and wrapped itself around his right leg, fortunately avoiding his sprained instep, and then two more for each arm and one around his waist. It raised him in a prostrate manner, and he suddenly felt better without a sharp pain racing through his limbs. Surprisingly, a fifth one appeared from the darkness and caressed his white face, wiping away the rivulet of water salt hot tears. All the green creepers felt oddly crisp and smooth, like they were alive in a more dragon-like way rather than being a mere root, and eventually Jack steadied himself and his cries quickly lessened to whining.
It was moor dark and silent aside from the wet sounds of whatever weeds he was caught in... swerving around him? He never believed roots could move, but it didn't seem like it was an animal either. He waited for several minutes in silence and just as he was about to call out, a tiny version of the big strong stems holding him crept along his crotch, coursing, and twisting around it like it was a tree trunk to be used for the base. His skin electrified with tingles, and he panted frightfully as it slid up his left leg, to his thigh and began to poke around at the end of his pants leg. Teeth gritted, he whined and tried to kick his legs free, but the beanstalk was far too strong. What was more unbelievable than anything was the strange, nectar-like substance the rising stalk thing was coated with, almost like a honeycomb.
The first normal sized vine was joined by another one the size of an oak branch that joined in the prodding and yanking on his other leg, and within three minutes it discovered how to pull his pants off. Jack's mouth went dry, and he wished he hadn't neglected wearing underwear tonight. The stunned boy bent his legs at the knees and brought them together as much as the beanstalk would allow, but the cool underground air still prickled at his sparsely hairy hole. Heart pounded sporadically and he clenched his blue eyes shut, encouraging himself to calm down. Whenever Jack was very nervous or excited, his dick grew tingly. This moment was no different.
It was as though the stems and leaves could breathe in his scent, and even as he locked his knees together, they wouldn't be challenged. The larger tendrils around his legs pulled up toward his slim chest and let his legs closed shut, although the embarrassing position only served to make him more defenseless. Two tiny creepers, the same ones from before he assumed, explored around his trembling ass cheeks like a thief looking for a way in. As soon as the wet tip of one caressed his untouched asshole, Jack wailed and tried to escape only to find himself completely bound.
The beanstalk seemed to be drinking in knowledge, because the second tendrils needed no help finding his now steaming sweaty ass. It was considerate in its jabbing, never doing anything more than soft caresses on his exterior rim. Heavenly it felt, and Jack felt himself settle into the touch a bit. No person or sensation had ever paid so much attention to his ass before- they were too emmeshed within their own appetites.
Eyes bulging, he felt his shirt being tugged on and then pushed up to expose his chest, which were promptly attacked by two more branch-like members that attached themselves as leeches onto his nipples ravenously. Somehow, they sucked like a newborn to a tit, and Jack moaned loudly both in fear and pleasure. His ass was more loose now, some of the oily lubricant running down between his ass cheeks, and the stems down there squirmed and wriggled happily in the liquid. Jack's cock grew harder as he became hornier, and within just a few minutes the firm shaft outstretched just about as if sprouting from between his tightly shut anal lips. His bowl-cut head flung back, and his mouth hung agape, and now instead of wanting to keep his legs sealed shut, he was fighting to pry them open.
"Shit...please," he moaned, yet was met with no response.
The small, merciful tentacle that'd been playing with his anal lips drew back, and he nearly cried out at the deprivation, but the sensation of something larger and stronger made him shut up. It poked blindly at his inner thighs, leaving strings of thick liquid on his wet skin anywhere it touched, before finding its target. Jack's anal gates parted easily for it, but he quickly realized it was far too powerful for him. Situating its tip just between his hole, save the very imposing head of it wherever fitting enough to hold at the opening of his ass, and Jack grew afraid. It was almost as if it was planning its next move.
Five smaller vines came back, snaking along the shaft of the main one until they too settled just at the entrance of his hole, and he fidgeted his hips down onto them just to try and get some sensation back. The giant stem withdrew, disregarding its lesser vines behind which wanted their turn with their prey.
One, and then the other slithered slowly into his ass. They were only the thickness of cooking utensils and so he couldn't feel them much at first, but then he felt them begin to swell. A deep moan broke him, and he wanted so badly to lower his hand between his legs to him brutally, begging penis. To no avail, as the stems still held him rigidly.
The boy's hips bucked and he cried out in frustration as the two creepers inside him grew slowly from twigs to rolling pins, eventually to the size of an axe handle. Why wouldn't they just churn him like butter? Jack cried out for them to fuck him, which earned him nothing but a jolt from the limbs inside him as they pumped. His orgasm was so close, and it was like this deviant beanstalk was mocking him.
"Oh my...my God...Please!" The boy roared, bucking his hips against the writhing stems deep in him.
The beanstalk apparently heard him this time, and they began to pump in and out of his raw leaking ass one at a time, in stages. Jack was nearly lost at this point, moaning and squirming and imploring for more, and when he felt something firm, hot, and rough flick his cock he nearly cried with aroused joy.
The branches holding his legs together finally relaxed and let him stretch them apart, and just as he felt the warm thrills of orgasm at the back of his mind begin to increase, one of the tendrils in his cave closed in and began to wriggle around at his ass. Tongue jutting through his lips, he gasped and wailed a "AHH!" into the darkness, his orgasm still growing even as he tried to tense his asshole to deny entrance. The vine wasn't having it, though, and it's massive bulk of nectar saw its fluid entrance into the lad. It didn't hurt as much as he imagined, and within a few facile strokes he was growing to enjoy it. All that mattered was the stimulation on his dick built up, and so far, it was indescribable.
Again, the limbs began to grow. With a shamelessly loud moan, Jack felt his passes expand with them until finally it was so mighty within him it was beginning to sting. Pushing him back slightly hairs breadth on the edge of release, but the lubrication from him and the tentacles made a new assault and soon enough his throat and ass were welcoming their besiegers with submissive...um, gates. Imagining Red and Jillian in his place while he was the growing root enveloping them.
"Yes, fuck, more," he moaned quietly, repeatedly. The vine on his dick increased its speed and he bucked his hips madly, desperate to finally cum. In a beat, his toes began to curl, his aching legs contracted, and senses frozen. He was no longer a boy, but a man.
The stem on his cock pumped away fiercely, and the ones in his mouth and ass retracted so quickly there was an unmistakable sucking sound from his flesh as it tried to keep them there. Jack cried out, fighting for his left arm so he could finish pleasing himself. He lacked the vigor of a knight, though, and his dick and stinging ass thrummed bitterly, the soreness in his holes and cock were already taking hold, and yet he wanted nothing more than to have those humongous vines, back inside, defiling him.
As his heart rate was slowing and the thumping between his legs began to ease, he felt something slithering back between his legs. It prodded at his backdoor, and he recognized it at the first colossal member, and this time he wasn't as scared. Instead of revulsion, he panted hard and tried to thrust his hips toward it. Jack's mind was clouded with lust and feverishness, and yet the beanstalk that held him prisoner behaved like there was no need to rush the joy of the coupling.