Another Halloween Dare

Another Halloween Dare

Coverart by Queenchikkibug

This year's Halloween story, based on two suggestions on Tumblr and a sequel to "A Halloween Dare" which you can read HERE

Contains: M/F, tentacles, huge breasts, big ass, vaginal sex, double vaginal, anal, blowjob, deepthroat, hotdogging, excessive cum.

Enjoy!

Another Halloween Dare

‘Man…How do I manage to keep getting myself into these kinds of situations?!’ Jacqueline “Jackie” O’Mara complained as she carefully made her way to the outskirts of town. ‘I’m starting to feel kind of ridiculous now that the booze is wearing off…’ She hissed to herself while the cold October wind whipped around her bare, shapely legs.

Jackie quickly pushed the bedsheet she was wearing down, but was a little too late and her meaty, freckled buttocks were briefly exposed for the world to see. Jackie quickly whipped her head around but nobody, aside from her, seemed to be there. At least, she thought so. The holes in the bedsheet were rather small and it was difficult to see in the dark.

Jackie readjusted the sheet to fit more comfortably over her red fauxhawk and, more importantly, to peer a little easier through the holes cut in the bedsheet with her big blue eyes. After she finished pulling the sheet down over her ass she pulled her hand away, seeing as the wind had died down. Instead, she crossed an arm over chest in an attempt to hide the way in which her thick nipples were making her “costume” tent out even further than her huge, heavy breasts already did.

‘I think Rosie was a little too excited to use those scissors.’ Jackie grumbled as she used her free hand to tug the ragged “hemline” of her sorry excuse for a costume down over her broad hips again.

Last year, Rosie Jacobs had dared Jackie to go home topless. Her breasts covered in nothing but bodypaint. Due to circumstances out of her control, Jackie had lost both the paint covering her chest and the Daisy Dukes Rosie Jacobs had loaned her. So she had walked the rest of the way home in a bedsheet. Somehow, word had reached Rosie and as “punishment” she and some friends had dared Jackie to go to one of the abandoned farms on the outskirts of town and bring back the biggest pumpkin she could find.

‘Sounded easy enough,’ Jackie grumbled when she recalled the proposed punishment. ‘Of course, there was a catch!’ The redhead continued to grumble.

Since she liked running around naked underneath bedsheets on Halloween nights, Rosie had a little gift for her. It was then that she handed Jackie her current costume. Already being quite drunk, and having done something similar the year before, it wasn’t all that difficult to convince the short, curvy redhead. Of course, now that her Dutch courage had started to fade Jackie started to regret her actions.

‘Let’s just get this over with.’ Jackie murmured to herself as she noticed a collapsed farmhouse with an overgrown field and, fortunately, a pumpkin patch. ‘Geez, this town sure has a bunch of abandoned homes and stuff…’ The redhead thought aloud, thinking back to the villa she had used as a shortcut a year ago.

Sadly, the pumpkin patch was overgrown with weeds and seemed to have gathered a significant amount of junk over the years. A few small pumpkins had managed to grow in these conditions, but Jackie doubted Rosie would be satisfied with one of them and she didn’t like losing. Not even when it was about something as silly as a dare like this.

‘Come on, there’s gotta be something here!’ Jackie muttered to herself as scanned the pumpkin patch for any of the bigger plants. But with how small the holes in her sheets were, combined with the overall darkness, it was hard to see.

‘Ah, screw it!’ Jackie cursed, as she threw off her “costume”. ‘It’s not like anyone’s around to get a good look anyway.’ She muttered to herself, though her cheeks were bright red as she said it.

‘That’s…’ A voice suddenly called out. ‘…where you’re wrong!’

Whipping her head around Jackie suddenly noticed a pumpkin that was nearly twice the size of her head. One she was pretty sure wasn’t there before. As she watched a series of triangular holes started to appear, resembling eyes and a nose before a sinister jagged smile appeared below them a moment later. Now, a jack-o-lantern was looking back at Jackie.

‘Boo!’ The voice shouted as an eerie green light filled the jack-o-lantern, and Jackie shrieked and jumped in the air.

Laughter emanated from the jack-o-lantern as it rose up from the ground. It just kind of floated there as it continued to laugh while Jackie looked on in a mixture of confusion and horror. Then, a body started to manifest underneath the floating pumpkin. A body dressed in noble attire. Noble attire that looked vaguely familiar to Jackie…

‘Looks like I got you again!’ Daniel chuckled as he lifted the jack-o-lantern up to reveal dark, sparkling eyes, a mischievous smile and sharp, youthful facial features framed by long dark hair.

‘W-what…the…hell?!’ Jackie yelled at the ghost. ‘How? Why?’ The redhead stammered in confusion. ‘Aren’t you supposed to be haunting that villa?’

‘I can move around.’ Daniel mused as he stuffed the jack-o-lantern underneath one of his arms and began floating around the short, but stacked, redhead. Observing her huge, heavy breasts and large, freckled behind as he circled her. ‘Nothing’s tying me to that place.’

‘So what, you decided to go and stalk me?’ Jackie asked with a raised eyebrow while folding her arms underneath her breasts, making the freckled globes look even larger in the process.

‘Now what gives you that idea?’ Daniel asked, laying his free hand on his chest as if offended.

‘Come on, don’t try to tell me you possessed a pumpkin in a place like this for fun?’

‘Well, it was always a fun way to scare someone.’ Daniel replied with a shrug. ‘Though, thinking about it, I might be the reason nobody’s tending to these pumpkins anymore.’

‘Sooo? Why are you here?’ Jackie asked with a mischievous grin. Wiggling her hips. Partially from the cold and partially to tease the ghost.

‘Guess you’ll find out!’ Daniel said, ominously, as he donned the jack-o-lantern again.

As he did, the jack-o-lantern began to swell. Larger and larger until his body was completely swallowed by the now giant jack-o-lantern. Jackie looked on in a mixture of confusion and excitement as she remembered her encounter with the young ghost a year ago. And her excitement was well founded as glowing green roots shaped like tentacles of various shapes and sizes poured from the jack-o-lantern’s jagged smile and edged closer and closer to the short, curvy redhead.

‘Last chance to run!’ Daniel’s voice came from the jack-o-lantern in a teasing tone, though it sounded deeper than usual and echoed faintly.

‘Hell no!’ Jackie replied, smiling fiercely and showing her teeth. ‘When will I ever have the chance to try something like this again?’ She asked as she spread her arms, seemingly welcoming the tentacles. Having completely forgotten about the reason why she came here in the first place.

No reply came from the giant, floating jack-o-lantern. Instead, it let its tentacles speak for him. The thick, glowing appendages snaked their way across Jacqueline’s bare legs and up her thick shapely thighs. The short redhead shuddered slightly at the sensation, it was like a dozen different tongues slowly licking their way up to her crotch. The imagery alone made her pussy clench in anticipation. Unfortunately, the roots pouring from the jack-o-lantern stopped when they had completely encased Jackie’s legs. Their tips waving back and forth just a few inches away from the redhead’s, now moist, labia. As if to taunt her.

‘Oh, fuck you!’ Jackie swore at Daniel as she uselessly tried to lower herself onto the tentacles. But the possessed jack-o-lantern’s only response was to make a green light shine brightly from the carved mouth. As if to indicate that it was laughing at her.

Since lowering her hips was clearly impossible, Jackie hoped to bring herself over the edge now that Daniel had gotten her this excited. The jack-o-lantern clearly sensed her intent, however, as glowing tentacles whipped around her arms encasing them in a similar fashion as her legs. It tickled as they trailed down her arms and underneath her armpits, leaving a sticky trail of ectoplasm in their wake. But the strange vines did not stop at only her arms, several of them slipped past her armpits to instead cup her huge, freckled tits. Not that they were very successful, as Jackie’s chest threatened to spill out of their grip almost immediately. But at least the jack-o-lantern had a better look at the slight pudge of her stomach now.

‘Now, isn’t this a sight?’ Daniel mused, his voice remained deep with that faint echo to it. ‘It’d be a shame to not share it with anyone else…’

‘What?!’ Jackie squeaked, but Daniel was already spinning her around.

Jackie didn’t attempt to struggle. Not that it would be any use with all those tentacles wrapped around her anyway, right? Slowly she was spun by the giant jack-o-lantern, and he didn’t stop until she was faced completely away from him and then…nothing. The road she had taken to get here was completely deserted. She released a breath she didn’t realize she had been holding, but her relieve was short lived as a thick tentacle suddenly forced its way into her dripping gash. Another squeak passed Jackie’s lips while the enormous jack-o-lantern behind her released an evil chuckle.

‘Got you!’ Daniel said mockingly. ‘But what’s this?’ He asked, as two tentacles that were wrapped around Jackie’s legs creeped a little closer to her crotch to prod and poke at her plump, soaked pussylips. ‘Could it be you were hoping that there was someone there, watching?’ The enormous jack-o-lantern wondered aloud while forcing his tentacle deeper into Jackie’s muff, causing the redhead to release a shameful moan.

‘Don’t be ridiculous!’ Jackie snapped, rather weakly. She had, after all, been walking around naked save for her sneakers and a bedsheet before running into Daniel tonight. And the year before she was topless save for the paint coating her tits. So maybe Jackie did have a bit of an exhobitionist streak in her. Not that she’d tell Daniel, he seemed like the kind of pers-… ghost who’d never let her live it down.

‘My, aren’t we defensive?’ Daniel mused in that deep, echoing voice. ‘Maybe that has something to do with how honest your body is?’ The giant jack-o-lantern cooed as he slowly slid the tentacle inside of Jackie back and forth, causing lewd squelching sounds to come from her dripping gash.

Jackie could only blush and suck on her bottom lip at that. She was happy Daniel couldn’t see her face, but the ghostly chuckle that came from behind told her he was very much aware of her embarrassment. Instead of teasing her further, however, Daniel seemed to have decided to start fucking her in earnest. The tentacle that had been gently moving back and forth in Jackie’s cunt, teasing her sensitive pink folds, began to pick up the pace. Meanwhile, the two tentacles teasing the redhead’s pussy lips were joined by a smaller third one that sought out her stiff pink clit.

‘My oh my, this form is quite amazing!’ Daniel muttered to himself as he watched the stream of lubrication that poured down Jackie’s legs. ‘Let’s see how much more you can handle!’ He growled in that deep, ominous new voice of his.

A moan passed Jackie’s lips, but if it was one of protest or pleasure Daniel didn’t know. Hell, Jackie didn’t even know herself! The slick tentacle thrusting in and out of her cunt reached deep and twisted and turned at strange angles. It was even better than Daniel’s tongue the year before and the whole ordeal made stars dance in front of her eyes. She dimly noticed as more tentacles spilled from the jack-o-lantern’s smiling mouth to pry her meaty, freckled buttcheeks apart.

‘Now, isn’t this a sight for sore eyes?’ Daniel chuckled as he watched the two pale, ballooning orbs jiggle and bounce as he clapped them together. Getting the occasional glimpse of the redhead’s tight, pink asshole and her pussy which was stretched around his invading tentacle.

With another chuckle a tentacle disappeared between Jackie’s big, soft buttocks and slowly began to rub against the redhead’s winking asshole and stretched pussy. Soon after, the freckled globes were pushed tightly around the tentacle that was hotdogging Jackie by its brethren and within seconds, the short, curvy lady’s meaty asscheeks were shiny and sticky with the ectoplasm that leaked from the glowing green tentacles.

‘Oh, I did miss this softness.’ Daniel mused wistfully in that deep, echoing voice of his while the tentacles cupping her huge breasts pushed them tightly together while the two tentacles teasing her labia slowly inched their way up.

Jackie shivered as the tentacles made their way up her plush stomach, coating her body with even more of the sticky ectoplasm, before she felt the tips of the glowing appendages tickling the underside of her huge, freckled jugs. A giggle passed the short redhead’s lips, before it turned into a soft moan as both tentacles forced their way into the underside of her cavernous cleavage. Due to how slick both were with a mixture of ectoplasm and Jackie’s own lubrication they easily slid back and forth between the short woman’s soft knockers.

Both tentacles spent a fair amount of time in Jackie’s cleavage sliding back and forth slowly, spreading their ectoplasm until it started dripping from Jackie’s cleavage even with how tightly they were being held together by the rest of the jack-o-lantern’s tentacles. Apparently the ectoplasm dribbling out from between Jackie’s breasts was some sort of signal, because the duo of tentacles suddenly peeked out from the top of the redhead’s cleavage and their tips made their way to her stiff, thick nipples. As they wrapped around the fat pink nubs, Jackie cried out in pleasure. And another tentacle abruptly found her open mouth.

Now that her mouth and pussy were stuffed, and her nipples and sensitive clitoris were being teased, Jackie struggled against her bonds as much as she could as shocks of pleasure ran through her body. Sparks went off in her head and copious amounts of lubrication continued to flow from her stretched, tentacle stuffed snatch. Clearly, Daniel thought she wasn’t being pleasured enough. Or perhaps he himself found that he hadn’t had enough as the tentacle that was currently hotdogging her soft asscheeks began to worm its way into her ass.

Jackie moaned around the tentacle that made her throat bulge at the strange sensation. But that was all that it was, “strange”. Despite the size of the tentacle that was invading her anal tunnel, it didn’t hurt. It felt like the first time she had sex with Daniel. Despite the size of his member, it felt as if it had both stretched her pussy and passed right through at the same time. Even though these tentacles seemed a lot more solid, the sensation was much the same. Daniel, meanwhile, seemed to notice that Jackie had realized this, as another tentacle made its way to her already stretched pussy…

Jackie’s eyes widened when she felt the tip of the glowing green tentacles brush against the already stuffed entrance of her cunt and began to utter some muffled protests. Not that any of them stopped Daniel. Moments later, the second tentacle slipped into the redhead’s dripping gash and Jackie’s body briefly went limp. Possibly due to shock. However, there was no pain. The sensation felt similar to that of the tentacle currently pumping in and out of her bowels. So even though Jackie could see her own stomach bulging outwards in a rather obscene fashion as the trio of tentacles snaked their way in and out of her body, she felt no pain. Only pleasure.

After that, the passage of time was a little vague for Jackie. The road Daniel had faced her towards remained empty and aside from the ethereal green glow that came from the enormous jack-o-lantern and its tentacles, the pumpkin patch and the surrounding area was pitch black. So, for an unknown period of time, Jackie was stuck in some sort of haze. Her mind felt slow, like molasses, and her limbs twitched and jerked without her input as Daniel used his tentacles to push all the right buttons. A mixture of drool and ectoplasm ran down her chin as the redhead continued to stare at the road with unfocused eyes.

I bet I look quite silly right now… Jackie thought to herself, as she pictured herself held aloft by tentacles with all her holes stuffed. Fluids leaking from both her mouth and her gash. It was quite a strange thought, because if her mind wasn’t so clouded by pleasure she’d realize that the image might look quite terrifying to a random passerby.

This realization hit her quickly, however. Because when she saw a light in the distance making its way over the same road she had used, she panicked. Was it a flashlight? The light of a bicycle? Or did it come from a motorbike or car? How quickly would she be spotted? I have to tell Daniel! Jackie worried, as she did her best to pull her head back. Unfortunately, the tentacle that was currently making her throat bulge was far too long and clearly had no intention of leaving this warm, wet hole.

Meanwhile, the light came closer and closer. Jackie’s heart was pounding in her ears and she quickly began to breathe loudly through her nose. She was panicking, but at the same time her anal tunnel and pink folds were clenching and unclenching powerfully around the tentacles invading her holes. Clearly, that small exhibitionistic part of her was excited about the prospect of being discovered. Still, when that light continued to approach Jackie was quick to release some muffled moans of protest. Spittle and ectoplasm flying from her mouth and landing on her huge tits that continued to be fucked by the jack-o-lantern’s glowing vines without a care in the world.

However, when Jackie thought she saw a silhouette of someone approaching, she was abruptly yanked backwards. She screamed, but fortunately the tentacle merrily pumping its way down her throat muffled her voice once again. Before she knew it, Jackie was sitting in darkness. It appeared as if all the tentacles had decided to leave her alone. But she was sitting on something soft…and moving. Green light suddenly shone down on her and looking up, she saw Daniel floating down towards her with a wicked grin.

‘Now, that was close, wasn’t it?’

‘You bastard!’ Jackie croaked, glowing ectoplasm and strings of drool hanging from her plush lips. ‘Why did you wait that long before…’ Jackie growled, looking around in confusion. ‘…before pulling me in here.’

It appeared that Jackie had been pulled into the jack-o-lantern somehow. She could look outside through what looked like a carved pair of eyeholes and a jagged smile. It felt as if they were a lot closer to the ground, however. And smaller too. Aside from that, it was clear now that the soft, wriggling mass she was sitting on were all tentacles. In hindsight, she probably shouldn’t have been surprised by that.

‘Because you were enjoying it, of course!’ Daniel replied with a smug grin. ‘And don’t think you can talk your way out of this one,’ the ghost continued, not giving Jackie a chance to reply. ‘All these things are connected to me in a way.’ He explained, gesturing at the tentacles sliding over Jackie’s legs and creeping their way up her body. ‘You’ve got no idea how hard it is to not just…explode.’ He finished, voice slightly strained.

‘Thanks for the tip.’ Jackie growled as she raised her hand towards the crotch of Daniel’s trousers…only for her hand to pass through him. ‘Damn it!’

‘I should probably play along.’ The ghost chuckled as the nobleman attire he was wearing faded. Now he floated above Jackie completely naked.

‘Fuck, I forgot how big you were…’ Jackie swore as she glanced at Daniel’s monstrous erection. It stood almost completely vertical, laying across the ghost’s stomach while the crown nearly reached his chest.

‘It’s also a lot harder than any tentacle.’ Daniel replied, as the huge pole took on a more horizontal position. Now, the thing was only a few centimeters removed from Jackie’s soft lips.

‘It sure looks that way…’ Jackie mused, her hot breath blowing over Daniel’s cockhead. Almost immediately, long strands of precum began to leak from the ghost’s widened cumslit.

Simultaneously, Jackie felt several big wads of ectoplasm splatter on her legs, on her stomach and on her ass. Looking up, she noticed how Daniel’s smug grin had disappeared. Instead, he was clenching and unclenching his jaw in a desperate attempt not to cum. Seeing that, Jackie just couldn’t resist! So the short and stacked redhead quickly pushed her head forwards, engulfing the young ghost’s monstrous shaft in her warm, wet mouth. Jackie had remembered how Daniel’s ghostly prick had been cool to the touch last year, but now? Now it almost felt as if it was burning!

‘Fuck…’ Daniel growled, his brow furrowed as he stared down at Jackie. Currently the redhead’s cheeks were bulging outwards due to the large amount of precum that had poured from his cocktip. But within seconds it all seemed to be gone. ‘Well, don’t think I’m done teasing you just because of this!’ Daniel snapped as he narrowed his eyes at her.

Tentacles raised in response to his words, slick with even more ectoplasm than before, and closed in on Jackie. The short redhead felt the leaking tip of one tentacle slide against her pussy, which was still soaked with her own juices and the ectoplasm of previous tentacles, before it slammed into the pink tunnel without a second warning. A muffled yelp of surprise, and slight discomfort, passed Jackie’s cockstuffed gob and with a glare up at Daniel she forced even more of his pre-leaking member into her mouth.

When Daniel moaned the tentacles closing in on Jackie briefly faltered and hosed her body down with more droplets of ectoplasm. But when the ghost controlling them recovered, so did they. Before Jackie knew it two tentacles wrapped around her breasts and began to slide up and down them in a milking motion. While another forced its way into her slick, slightly gaping butthole. But aside from a muffled moan around Daniel’s shaft, she didn’t let up and continued sucking him off.

Both seemed to struggle to get each other off first. Even though Daniel might have been successful in that regard earlier, several times in fact, Jackie wasn’t about to let a thing like that slow her down. Faintly glowing ectoplasm and her own drool were running down her chin as the redhead bobbed her head back and forth rapidly. However, Jackie thought that she could still increase her pace further and grabbed onto Daniel’s firm asscheeks. Oddly, her fingers didn’t pass through the young man’s ghostly form.

Looking up, she swore that Daniel’s face was soaked with sweat as he focused on trying to not blow his load while controlling the several tentacles that were the cause of Jackie’s own sweat streaked face. Apparently trying to focus on keeping your body immaterial was a bit too much for him at the moment. And Jackie was all too happy to take advantage of that weakness. The redhead grinned wickedly around Daniel’s shaft as she increased her grip on his buttcheeks, before roughly shoving her head forwards. All the tentacles that were currently using her body started to move in a slow, jerky fashion.

A few spurts of ghostly precum were fired nearly straight into her stomach as she kept her lips wrapped tightly around the base of Daniel’s monstercock for several moments. All while looking up at him with a mischievous glimmer in her, currently reddening, eyes. Daniel looked down at her with a clenched jaw, but seemed to regain some composure as his lips stretched into an impish smile and all of a sudden the tentacle stretching Jackie’s pussy began to move with a renewed vigour.

‘I’m not…quite done yet!’ Daniel growled, as the tentacles wrapped around Jackie’s breasts stopped their strange, jerky movements and began to slide up and down her huge, heavy breasts as if they were “milking” them again.

Jackie moaned loudly around Daniel’s shaft and tears of effort ran down her cheeks. Obviously, she wasn’t going to sit still either. And just when the tentacle stretching her ass started picking up the pace again, Jackie pulled her head back roughly. Strands of ectoplasm and spittle snapped off of the ghost’s meaty pole to land on the writhing mass of tentacles below, and all of them briefly seemed to pause, before Jackie shoved her head forwards again. Which seemed to be their cue to start moving again.

‘Haha, I don’t think I’m gonna win this one…’ Daniel chuckled as he watched the short, stacked redhead furiously bob her head back and forth.

Sure enough, moments later the tentacles trying to please Jackie were moving in the same, jerky fashion they had previously. Nearly two minutes had passed before they stopped moving completely. Three minutes, and Daniel released a deep, dark groan before his body turned incorporeal and he floated backwards.

‘Wha-’ Jackie began, before a rope of white, luminous spunk splattered against her forehead. Followed by another, and then another. Until her fauxhawk was weighed down with so much ghostly semen that it was laying flat on the top of her head.

Daniel wasn’t done, however. No, it was just the beginning. While jets of hot, viscous semen were shooting from the tip of his monstrous member all the tentacles wrapped around Jackie also began to bulge and twitch. As did the writhing mass that she was sitting in. Jackie realized this a moment too late and suddenly she felt her stomach balloon outwards as the glowing appendages that were currently twitching in her pink tunnel or stuffed in her bowels began to spew out loads similar to that of Daniel.

Not soon after, the glue-like, glowing substance was sliding from her massive, freckled tits. But the biggest mess was yet to come… As soon as Jackie thought Daniel’s climax was over, the wriggling mass of tentacles she was sitting on began to spew out their long strands of glowing green ectoplasm, and they didn’t stop until Jackie was up to her waist in the sticky stuff!

Although not as powerful as the previous climaxes that had ripped through her, the whole situation did bring Jackie over the edge and her whole body shivered as she closed her eyes. Enjoying the afterglow in the pool of ectoplasm.

Or at least, she tried to.

Suddenly, she was ejected from the jack-o-lantern. Rather forcefully, in fact. With a loud: ‘Oof!’ she fell on the ground. Fortunately for her, the ectoplasm and cum covering her body seemed to have disappeared as soon as she was thrown out of the jack-o-lantern or she would have been a whole lot dirtier. Jackie was to her feet instantly, ready to yell at Daniel…but all she saw was the jack-o-lantern. And it was a whole lot smaller now. Perhaps a little bigger than her head.

‘Sorry about that,’ Came Daniel’s voice, though Jackie couldn’t see him anywhere. ‘I believe I pushed myself past my limits for this “Trick”.’ He explained. ‘Though I guess it was more of a “Treat” for you, no?’ He added, and Jackie could feel the smug smile on his face even though she couldn’t see him.

‘You’re going to be alright?’ Jackie asked as she looked for her “costume”.

‘I must rest, but I’ll be fine.’ Daniel replied as Jackie donned the bedsheet once more.

‘Cool, cool,’ Jackie muttered. ‘I’m taking the pumpkin, though!’ She snapped back as she hoisted the jack-o-lantern up. ‘It’s the least you can do!’

‘If that’s all you’re asking for than I certainly won’t complain!’ Daniel mused. ‘Anyway, I must rest now.’ He repeated, and he sounded exhausted as he spoke. His voice slowly fading away.

Jackie only nodded at the empty air, uncertain if Daniel could still see her, and began the long walk back to Rosie’s house. Once the abandoned pumpkin patch was out of sight she turned her attention to the jack-o-lantern in her arms.

‘This isn’t some trick so you can screw all my friends, right?’ She asked it.

But there was no response…

THE END