A Halloween Dare

A Halloween Dare

Cover by Queenchikkibug

Although I do not celebrate Halloween myself, I did like the idea of having it as a theme for my stories. So back in 2017, I asked for suggestions and this is what came out of it.

So here we have Jacqueline “Jackie” O’Mara leaving a Halloween Party topless, for a dare, and taking a shortcut through a Haunted House. Queenchikkibug, along with some other friends on my Discord, got a sneak peek and liked it enough to provide a cover! I hope you enjoy it as much as you like the story!

Contains: M/F, huge breasts, big ass, monster boy, ghost, huge cock, long tongue, cunnilingus titfuck, excessive cum, vaginal sex.

Enjoy!

A Halloween Dare

Jacqueline O’Mara, Jackie to her friends, stumbled out onto the street. Loud music blared, and would most likely continue to blare, from the house behind her. Some old friends from school were throwing a party and, after filling the short redhead with some Dutch courage, dared Jackie to make it home in her current “costume”.

Said costume were a set of Daisy Dukes that belonged to Rosie Jacobs, the girl who was throwing the party, a tall, leggy blonde on which they would have no doubt already looked tiny. Now, Jackie was short, but she had a bit more meat on her bones than Rosie. Her hips were broad and perfectly accentuated her thick, ballooning asscheeks which could barely be contained by the frayed garment clinging to the pale, freckled globes that peeked out from the top of it. Underneath it were shapely thighs that touched and thick legs contained in fishnet stockings that had patterns in them that resembled a spider’s web.

It wasn’t much of a costume but it was really all she wore aside from a pair of black and white sneakers. This was because part of the dare had been that Jackie go topless, with her only cover being some paint. Seeing as she had already been pretty liquored up before it was time to leave, Jackie had simply pulled her shirt over her head to present her jugs to Rosie and the other partygoers.

Her tits were her pride and joy, even though they were hell on her back sometimes. They weren’t exactly perky, the pale, freckled orbs were far too heavy for that. Nearly the size of pumpkins, they came down to about her belly and would cast a shadow over her crotch and legs if the light would hit them at the right angle. Her belly was plump enough to not completely disappear underneath her massive knockers, but none of the boys at the party seemed to care that she was carrying a little extra weight. None of the girls did either, for that matter.

Because apparently, Jackie wasn’t the only one that noticed that her breasts resembled pumpkins in size. For as soon as they appeared out on the open Rosie, and some of her other female friends that had a little too much to drink, set out on painting the humongous globes orange before making them up to resemble a set of jack-o-lanterns. Jackie wasn’t going to lie to herself, having felt so many hands and paintbrushes on her tits had been exciting. Especially because she hadn’t missed the way in which the crotches and legs of trousers had started to bulge outwards from the boys watching this display.

‘Goddamnit,’ Jackie swore. ‘It’s probably already turned into an orgy in there…’ She complained.

When Rosie had handed her the Daisy Dukes, after taking some selfies with Jackie’s massive “pumpkins”, Jackie had really expected that the blonde had planned for things to go a little further. But no, apparently she was more interested to see if the redhead would go through with this little dare.

‘What a fucking tease!’ Jackie swore as she brushed a hand through her short red fauxhawk, freckled cheeks pink because of both alcohol and embarrassment. ‘I better make it home before I force some kids to hit puberty a little early!’ She told herself with a dry chuckle when she realized she was still standing on the sidewalk in front of Rosie’s home.

With that in mind, she began to walk. For the first few feet she kept her arms crossed over her painted tits, but after a while she started to wonder what would happen if she would be seen? That movement behind one of the windows, did somebody waiting for trick-or-treaters spot her walking down the street topless and her ass nearly in view? Would they call the cops on her? And if a cop did approach, just what would they ask of her…?

As those thoughts raced through her mind Jackie’s arms slowly fell away from her huge, painted knockers while her heart pounded in her ears and her enormous chest rose and fell rapidly. The fact that she wasn’t in fact wearing a very tight top became more obvious as her thick nipples started to harden, making it appear as if the jack-o-lanterns painted on her tits now had noses. If someone got close enough to her now, they would definitely notice her massive jugs were out in the open.

‘Okay, this has been fun. But I really need a shortcut!’ Jackie hissed to herself, finally starting to sober up a little.

Just then, Jackie rounded the corner and found what she was looking for. The Westberry Estate. A massive fenced of villa nobody had lived in in years. It was dilapidated, overgrown and a massive eyesore, yet the township couldn’t be bothered to get rid of it. Nearly every man, woman and child knew about all the ways into the villa and over the years it had been used for many, many parties. Especially around Halloween, since it was rumoured to be haunted. In recent years, however, the popularity of the Westberry estate had waned somewhat.

So Jackie hoped nobody would be there as she slipped through a hole in the fence. Cutting through the estate grounds would not only save time in getting home. There would also be far less prying eyes.

To be absolutely sure there would be no “prying eyes”, Jackie decided against simply walking over estate grounds and cut through the villa itself. The locks of most doors and windows had long since broken, so getting inside was no problem. Jackie slipped in through a side door and stepped into the kitchen. Fortunately, the streetlamps from outside gave off enough light for her to find her way towards the hallway. Once there, however, she had the fright of her life as a figure in white came rushing towards her…

…but upon closer inspection, it was just a white sheet. Correction, someone under a white sheet.

‘Oh, haha! Very funny!’ Jackie yelled as she yanked the sheet off of whoever was hiding underneath it. ‘How long have you been waiting here to pull that prank off?!’ She added angrily.

Only, there was nothing underneath the sheet she was now holding. Just an empty hallway. As Jackie stared at the white sheet in her hand, she felt a chill. Her breath began to mist and lights that had not been on in years flickered faintly as she noticed the faint green outline of a person. When she took a step back, it solidified into the shape of a well-dressed, lanky young man with long hair that covered his eyes.

‘Boo!’ He yelled with his arms stretched above his head, his voice reverberating slightly.

Jackie screamed in terror, of course she did. But the young man, the ghost, didn’t do anything else. He just laughed.

‘Looks like I got you twice!’ He chuckled, showing perfectly straight teeth.

‘You… You’re a ghost!’ Jackie babbled.

‘Well, yeah!’ The young man answered with a shrug. ‘Didn’t you hear the rumours? This place is haunted!’ He said with a grin.

‘No, no… You can’t be real! I mean, you didn’t pass through this!’ Jackie hissed, as she held up the sheet.

‘I can stop myself from doing that kind of thing if I focus enough,’ the ghostly young man explained with a shrug as he flicked his hair away from his face, revealing his sharp, handsome features and a pair of dark, sparkling eyes that matched his mischievous smile. ‘Observe!’ He announced theatrically as he reached for Jackie’s chest.

Jackie was so stunned by all of this that she did not move out of the way as the pair of ghostly hands moved towards her. She only gasped in surprise as they hefted her huge, painted tits curiously. Both of the semi-translucent green hands felt cool against her skin, but not in an unpleasant way. Jackie could feel their palms press against her nipples and his digits softly dig into the heavy globes. It was the second time tonight someone was groping her like this.

‘Alright, you’ve had your fun. Hands off!’ Jackie chuckled as she tried to grab the young man’s wrists…

…only for her hands to pass through.

‘See? I was telling the truth.’ The ghost mused as his mischievous smile broadened.

‘Y-yeah,’ Jackie stammered. ‘Yeah, you did.’ She continued a little more confidently. ‘So would you mind letting go off my tits now?’ Jackie asked with an amused grin as she placed her hands on her broad hips.

‘Sorry,’ the young man replied, but Jackie noticed that his hands lingered on her chest despite his apology. ‘It’s just that I’ve never been able to touch a rack this fantastic when I was alive.’ He added, before releasing the redhead’s knockers with a firm squeeze.

‘Well, aren’t you a sweet talker.’ Jackie replied drily as she continued staring at the ghost and pushed her chest forwards.

‘I know, it probably would have been better if I hadn’t started this conversation of with squeezing your breasts. But I haven’t exactly had a lot of practice with flirting due to, y’know, being dead and all?’ The ghost replied, his tone of voice equally dry.

When he mentioned being dead, Jackie looked the young man over again. He was well dressed, for someone who would have died around the 1800s. But whether he had really died during that time period. Or if he was someone who had died while celebrating Halloween in this mansion, and this was simply his costume, Jackie didn’t know. What she did know was that the tight clothing clung to his slender, toned form rather nicely. And that it made hiding his member rather difficult.

‘After the night I just had, I don’t exactly mind a man that’s so forward…’ Jackie trailed off, as if waiting for the young man to introduce himself.

‘Call me Daniel,’ the ghost replied with a mock bow. ‘And you are?’

‘Jacqueline O’Mara, but call me Jackie. Only my mom calls me Jacqueline.’ She said by way of introduction, extending a hand.

Daniel mimicked her motion and extended his hand. Only his passed through Jackie’s arm to squeeze her breasts again.

‘Brrr…’ Jackie shivered, before attempting to swat Daniel’s hand away from her tits again. Only to fail miserably, of course. ‘You stop that!’ She hissed, but laughter bubbled forth from her throat as soon as she said it. ‘Is that the only trick you can do or something?’

‘Oh was that a challenge?’ Daniel mused. ‘Because I know plenty of other tricks.’ He growled dangerously.

‘Bring it!’ Jackie snapped, raising her chin at the ghost in defiance.

Daniel wasn’t about to back down and floated a little closer towards the short redhead. So close that Jackie realized just how much he towered over her, causing some of the fire to go out of her eyes. When the ghost noticed that, he flashed her another one of his trademark mischievous grins before his body slowly started to sink into the floor. He didn’t stop until his face was at the same height as her Daisy Dukes.

‘You want me to take those off for you, Casper?’ Jackie teased as she stared, somewhat nervously, at the young man half submerged in the wooden floor.

‘Oh no, that won’t be necessary!’ Daniel replied confidently as he reached for her buttocks.

Jackie gasped in surprise when she felt the ghost’s slender, but strong, fingers dig into her meaty, freckled buttocks. It was as if she wasn’t even wearing her Daisy Dukes any longer. But she still had them on. She could seethat they were on. That was when she realized that his fingers had passed through the material, of course they had! And when this realization hit Jackie, Daniel noticed and looked up at her and stuck out his tongue.

Only, this wasn’t just some childish gesture. Since Jackie soon noticed how it grew longer and longer while slowly coming closer to the crotch of her Daisy Dukes…

Just as Jackie had expected it passed through the garment, just as Daniel’s fingers had. And she couldn’t help but gasp as the cool, wet muscle brushed against her wet, darkened labia before diving into her hot, pink tunnel. Her folds clenched around the invader, but of course that didn’t stop the ghost’s tongue. Instead it slithered deeper into Jackie’s muff than any cock, toy or pair of fingers had made it. Colours danced before Jackie’s eyes and she felt something hot in the pit of her stomach.

But she wasn’t about to give this pervy ghost the joy of showing him how much pleasure he brought her. So instead of moaning in pleasure and asking for more, she nibbled on her bottom lip instead while clenching and unclenching her hands. Unfortunately, or perhaps fortunately, for Jackie this meant that Daniel only tried that much harder. More of the ghost’s impossibly long tongue seemed to fill her tight snatch. Yet, no matter how packed her pussy seemed to be, Jackie never felt any pain or discomfort. But she certainly felt surprise when the tip of the young man’s tongue wiggled its way out of her slit and moved upwards in search of her clit.

‘Oh fuck!’ Jackie gasped. She just couldn’t help herself as the wet, nimble muscle not only continued to move against her folds but was now also actively flicking against her hard little clitoris.

Her reaction spurred Daniel on even more. He began thrusting his tongue into her dripping snatch at an increased pace, causing the long, dexterous muscle to slide over itself and move as if it was some sort of tentacle that had folded in half within Jackie’s cunt. It was no surprise when a rapidly expanding damp spot appeared on Jackie’s Daisy Dukes as a mixture of her juices and Daniel’s ectoplasm-like drool ran rapidly from the redhead’s aroused muff.

‘Alright, I admit it!’ Jackie squealed, voice high and breathless. ‘This is a good trick!’

Daniel’s reply was to pull his tongue back from Jackie’s quim in one, smooth movement. But what Daniel had just done didn’t really seem to register with the redhead. Instead, she showed her teeth in a fierce grimace while her eyes rolled up. Daniel watched in some amusement as Jackie pushed her hips back and forth instinctively while the damp spot on her Daisy Dukes seemed to have grown even larger. Then, with another one of his grins, he released the young woman’s large behind.

With nobody supporting her, Jackie found that the pleasure that Daniel’s long tongue had brought her had left her legs quite weak. So it came as no surprise to her when they gave out, leaving her to fall on her ass with a loud yelp.

‘Jerk!’ Jackie hissed while one of her hands disappeared between her thighs, only to be stopped from petting her pussy by the denim material of her soaked Daisy Dukes.

‘I’m sure you’ll get a chance to get me back for that,’ Daniel’s teasing voice said from somewhere above her, even though she could not see him. ‘Oh no!’ His voice then added drily. ‘My clothes seemed to have disappeared! How embarrassing.’ Daniel said, his voice monotone as he reappeared right before the prone Jackie.

Because of their difference in height this meant that Jackie was about eye level with the ghost’s member. And, like she had already guessed from the tight trousers Daniel wore previously, the young man was hung. His member was only partially erect and nearly came to his knees and was a little thinner than the slender ghost’s own wrist. Long strings of ectoplasm-like precum hung from the crown, so long that they nearly touched the floor. It was clear that Daniel had been here alone for a long, long time.

‘You’re joking right?’ Jackie huffed, trying not to let her nervousness show. ‘That monster’s never going to fit!

‘Maybe it wouldn’t have when I still had a body…’ Daniel mused as he began stroking his member. ‘But seeing as I’m not exactly held back by a limitation like that anymore, I reckon we can make it work.’ He added slyly, dripping fat, lazy ropes of precum on Jackie’s huge tits as he slowly jerked himself off.

While most of Daniel’s body had felt cool to the touch, his precum was almost hellishly hot! Jackie couldn’t help but hiss as the clear, pale green liquid touched her chest and warmed her cold body. Without meaning to she began to work the ectoplasm into her skin, and found that it did not disturb the paint even if it made her breasts shine as if covered in oil. She only realized what she was doing when she noticed that Daniel was staring rather intently at the way in which her hands slid over her huge, soft tits.

‘Yeah, I’ve got some tricks too,’ Jackie said with a teasing little smile. ‘Why don’t you slide that monster of yours between my girls and I’ll show you?’ She asked, hefting her breasts for the young man’s benefit.

‘Y’know,’ Daniel mused as he watched the soft globes spill forth from Jackie’s small hands. ‘I’ve always wanted to try something like that back when I was alive.’

Jackie got no further warning than that. Daniel simply shoved his monstrous member between her jugs and began to pump his hips. Some of his form passed partially through her body which was both unnerving and sent another chill through Jackie, so she decided to aid the ghost by arching her back and pushing her huge cans around Daniel’s shaft. Almost immediately more of his unnaturally hot precum began to pour from his cumslit, drowning her cleavage in the eerie fluid and warming her body as it slid down over her belly.

Unfortunately, even Jackie’s huge jugs didn’t seem enough to contain Daniel’s monstercock as his cockhead still managed to peek out from her cavernous cleavage. At first she simply allowed it to rub over her neck and let it batter against her chin. She knew Daniel could stop that from happening, what with being a ghost and all, but either he enjoyed messing with her too much. Or simply forgot, as he was too focused on sliding his huge prick between her knockers.

‘Ah, to hell with it!’ Jackie growled before she angled her head downwards and opened her mouth.

Jackie’s lips stretched over Daniel’s large, ghostly dickhead whenever he pushed his hips forwards. Usually filling her mouth with way too much of his hot, ectoplasm-like precum in the process. At first, Jackie attempted to swallow some of it. More out of morbid curiosity than any attempt to not make a mess of herself. That ship had long since sailed, after all. Not that she got to experience an unique taste out of it, unfortunately. If anything it was as salty as expected, if not more so.

With her curiosity sated, Jackie simply let most of the ghostly precum escape from her mouth along with her saliva. There just was too much to swallow! So, considering how she was a mess already anyway, Jackie figured this was the best solution. As for Daniel, seeing a mixture of his precum and the redhead’s saliva dangling from Jackie’s nipples and making her huge knockers shine all the more only served to arouse him even further.

Considering how her mouth was stuffed most of the time, Jackie didn’t exactly have the chance to sarcastically ask the ghost if he was enjoying feeling her tits wrapped around his massive dong. However, she figured that her look of smug satisfaction would suffice. Though perhaps the effect was somewhat diminished by her stretched lips and bulging cheeks as Daniel’s fat crown hammered its way in and out of her gob.

Unfortunately for Jackie, as pleased as Daniel was with using her cavernous cleavage for his own enjoyment, he soon wanted more. Jackie could feel his normally cool cock start to warm up and throb between her huge, soft jugs. Almost like a heart. She guessed, going by the expression on the young man’s face, that he was about to cum soon. Where he all got it from, Jackie didn’t know. It felt as if her body was coated with his thick, sticky precum from chin to crotch thanks to the way it continued to slide down her tits.

As if sensing her thoughts, Daniel chose that moment to show her that she hadn’t seen anything yet.

With a soft grunt the young man pulled his hips back and hovered over Jackie, rapidly fisting his monstrous, precum drooling member. It was also the first time Jackie had the chance to admire the rest of his body, not just the stiff, meaty organ between his legs. Although Daniel had seemed slender in his clothing, he was not out of shape. He was built like a runner with a flat, toned stomach and obvious muscle showing along his slim arms and legs.

Not that Jackie had a long time to enjoy the view, seeing as it was all soon washed away by a fountain of faintly glowing white semen. Fat ropes splattered against her forehead and slid over her eyelids, though she could also felt a few thick beads end up in her red hair. Daniel’s main focus seemed to be on her chest, though. Which didn’t exactly come as a surprise. As the young man bombarded her pumpkin-sized hooters with hot jets of seed the jack-o-lanterns they were decorated with disappeared underneath a sea of white.

When Daniel was finally done, Jackie could do nothing more than lie on her back as she felt the thick slime slide between her breasts and down over her belly. Though much ended up staining the floor beneath her as well. But when she finally managed to wipe some of Daniel’s cum from her face, she noticed that the ghost wasn’t done with her yet. His monstrous shaft was still sticking upwards proudly. Daniel himself did seem less solid to Jackie’s eyes, but she figured it was just her imagination.

‘Now, I hope you’re ready to see if my “monster” fits.’ Daniel teased, narrowing his eyes while slowly stroking his erection.

‘Fine…might as well, since you don’t seem to be changing your mind any time soon.’ Jackie grumbled. Though she would be lying if she said that she wasn’t a little excited about what the ghost had planned.

‘At least let me take my shorts off,’ she quickly stated as Daniel floated over towards her. ‘They’re a big enough mess already, after all.’

‘Go ahead, I can wait a little longer.’ Daniel replied with a smirk as he observed Jackie, his arms crossed over his chest.

‘Yeah, I figured you’d at least get a kick out of watching me do this…’ Jackie grumbled as she rose to her feet amidst the wet splattering sounds of cum snapping off from her curves to hit the floor.

While she complained Jackie began to unbutton the Daisy Dukes she had borrowed from Rosie. The garment was fall too small for her, and even now she wondered how the hell she got it on in the first place. The redhead had to tug on the shorts several times before it finally started to slide down her hips, after which she proceeded to hop up and down to get it to travel even further down her legs.

As Jackie had predicted, Daniel indeed got a kick out of watching her get out of the only real garment she was wearing. The way her thick, freckled behind jiggled as she attempted to get out of the Daisy Dukes was quite mesmerizing. Not that he missed the way in which Jackie’s cumblasted tits shook as she hopped up and down to make even more of his jizz rain down to the ground, of course. All in all, it was quite a joy to see the feisty redhead undress and he could feel how precum had begun to drool from his cumslit again.

‘Alright, happy now?’ Jackie asked as she struck a pose, slightly out of breath from the ordeal of taking her Daisy Dukes off.

‘Absolutely…’ Daniel practically purred as he eyed Jackie’s aroused muff, and the small strip of red hair above it.

Jackie stood before Daniel, still posed with her hands on her hips. Simply waiting to see what Daniel had planned for her next. Then, to her surprise, she started to float. She shrieked in surprise, arms and legs cartwheeling into circles, while the young man watching her simply flashed her an evil little smile. While Jackie was still panicking slightly in the air, Daniel floated towards her.

‘I guess this is another one of your tricks?’ Jackie asked, raising an eyebrow at the ghost while trying to get used to the sensation of floating in the air.

‘Yep,’ Daniel answered cockily. ‘Using it this way is a lot more fun than floating furniture around and smashing it up, don’t you think?’

‘I’m not convinced yet…’ Jackie replied, narrowing her eyes while they sparkled mischievously.

‘Fair enough.’ Daniel replied with a nod, while grabbing onto the redhead’s thick, meaty thighs.

As Daniel’s large, precum-dripping cockhead came closer to Jackie’s flushed labia the redhead’s breath began to quicken. Her enormous chest rapidly rose and fell, causing more of the ghost’s cum to slide off and splatter loudly on the floor. Then, the crown of Daniel’s monster finally spread her pussylips and began to slide into her twitching, pink tunnel. However, to her surprise, it didn’t hurt.

Mostly it just felt strange as Daniel’s massive member both stretched her pussy and seemed to pass through it at the same time. The young man merely smirked at seeing Jackie’s expression, which was a mixture of lust and confusion. He gave Jackie a chance to get used to the strange of sensation, and then roughly continued pushing his hips forwards.

Jackie gasped as Daniel filled her in a way that no mortal man could. Her pussy spasmed powerfully around Daniel’s huge prick in response to it. Not that that slowed the ghost down in the least, of course. As Daniel’s meaty shaft was pushed deeper and deeper into Jackie’s muff a mixture of his precum and her clear juices were forced from her twitching pussy to join the mess on the floor.

The next few minutes barely registered for Jackie as powerful thrusts of Daniel’s hips forced his dick further inside of her. More of her girlcum was forced out of her twat thanks to this, and an obvious bulge began to show even on her plump belly. Finally, the ghost’s cockhead seemed to pass through her cervix and into her womb, which was something Jackie thought she never would experience.

Not that she was in the state of mind to worry about that now as her eyes rolled back and she screamed in pleasure. Still floating, her shapely form twitched and writhed in the air while Daniel continued to hold on to her thighs, unmoved.

‘Do try to stay awake,’ Daniel said smugly. ‘We’re not finished yet.’ He added, before slowly pulling his hips back.

Jackie only responded by grunting and moaning softly, drool slipping from her opened mouth as Daniel began to pump his hips back and forth. Slowly and gently at first, causing said moans and grunts to slowly rise in pitch. But as time went on, and more jizz slid from Jackie’s floating body, Daniel slowly started to quicken his pace. Ignoring the way in which the redhead’s slit desperately clenched around his shaft.

The next few minutes were a blur for Jackie, occasionally interrupted by bright flashes of light dancing before her eyes as another climax washed over her. Consciousness only fully returned to her when Daniel finally stopped moving, his dick inside of her to the hilt. She could feel his abnormally hot precum rapidly drip into her womb and like before Jackie could feel his member heat up within her. Jackie had just enough time to stammer a ‘Wha…’ before Daniel gave a deep, dark grunt.

Jackie’s eyes bulged slightly as she felt the ghost’s hot, viscous jizz blast into into her womb. Her chubby stomach, which was already showing a noticeable bulge thanks to Daniel’s huge cock, began to expand even further. Jackie gasped for air as the ghost’s ectoplasm-like cum began to spray from her stuffed snatch. Like before, Daniel’s form also began to fade somewhat and he actually seemed out of breath despite the fact that he lacked a physical form.

When the last few ropes of cum left Daniel’s cumslit, the ghost drifted backwards. Immediately a small waterfall of his glowing seed dribbled from her stretched snatch and Jackie slowly started to float downwards…before being unceremoniously dumped in the large puddle of cum and precum on the floor.

‘…bastard!’ Jackie babbled, bubbles of drool appearing near the corners of her mouth, as she felt the semen on the floor stain her thighs and buttocks.

‘Sorry, but it seems like my time’s up for the night,’ Daniel explained, though the mischievous grin hadn’t left his lips. ‘Happy Halloween!’

With those last words, Daniel disappeared.

Jackie remained lying on the cold, dirty floor for a few more minutes before she found the strength to stand back up again. Dried spunk was caked on her back, ass and legs and her red hair was a matted mess. She had lost track of Rosie’s Daisy Dukes a long time ago, but fortunately she had another option. The sheet Daniel had scared her with was still on the floor, luckily far away from the mess she had been lying in.

‘This wasn’t part of the dare. But considering how I would be naked except for my shoes and socks…I don’t think Rosie’ll mind.’ Jackie mused to herself, before throwing the sheet over her head and leaving the Wildberry Estate behind…

THE END