Once Upon a Halloween

(Usual Disclaimer Time: All the characters in this story are 18 years old or older, and since we're living in the wide wonderful world of porno-land here, where clichés roam free and things might get a little unrealistic from time to time, please remember it's all in good fun.)

(Author's Note: So, it's been a while since I've posted a story after facing some burnout on Senior Year Memories, and I'm trying something a little different this time. This will be a limited series with a light canon, meaning that while the chapters will all be related by characters and location, it won't be explicitly necessary to read every chapter to know what's going on. Each chapter will be its own thing, and can be enjoyed independently. I hope you enjoy! I also want to give special thanks to fellow Literotica author and SYM reader Lil_kitty for many excellent ideas and acting as a second set of eyes on this story, and for letting me know what did and didn't work; if you get a chance, please check out her work and drop some stars if you enjoyed, she writes some very hot and fun stories.)

***

Briar's Mill, California wasn't much of a town to look at. Not quite suburban and not quite rural, it lay in a middle-ground of uncertainty that had it perpetually looking like a town out of a PG-13 80s adventure movie featuring a bunch of kids solving mysteries on bicycles, but not one that could afford to be filmed in a nicer town. Oh sure, it had quaint businesses and family homes that had been in many a family for many generations, but if you looked close enough, half of those businesses were boarded up, or were soon to be replaced by their big chain counterparts, while the local Briar's Mill Mall was barely holding on. Most of the nearby farms were on the verge of failure, and while many of the older families stuck around, many more had long since parted.

As a matter of fact, there were pretty much only two things the town was noteworthy for.

The first, was being the hometown of a reasonably well-known pornstar named Alexis Ashe, but considering that wasn't something that you put on signs (and her reputation for being up for anything on camera), it wasn't exactly something Briar's Mill boasted about.

The second, however, was something they'd put far more pride into: they did Halloween right.

Between two of the still operating farms nearby specializing in growing pumpkins, and the abandoned gothic manor that was the Higgins House at the west edge of town (naturally claimed to be haunted), it was a reputation that only came naturally, and one the town leaned into. Being Instagram-ready for the seasonal crowd wasn't saving the town from failure, but it was slowing the downward spiral. People would come from far and wide for a Halloween experience in Briar's Mill, taking in the Briar's Mill Halloween Carnival just off Main Street, or a Halloween movie marathon at the Camelot Theater, or even just trick or treat at the many amazing yard displays.

It was a magical time of year in Briar's Mill, a time of possibility and wonder, where anything could happen to anyone, and for ten seniors of Briar's Mill High School who had been friends since childhood, each would find something that night that would make it particularly memorable...

***

It was the afternoon of Halloween, and a man in a grim reaper's robe walked up and down the seasonally decorated Main Street handing out fliers to anyone he didn't recognize.

"Come on down, that's right I said come on down, to the Mortuary of Doom Haunted House! You can skip the entire rest of the carnival because it's the only thing you need to see. Why's that, you say? Well, for one simple reason: it'll scare the shit out of you!" he declared with great pride.

Very little of this was in the script he was given to promote the haunted house, but 18-year-old Miguel de la Cruz had never exactly been one for following scripts. He was a handsome young man with a confident grin, well-groomed black hair, warm brown eyes and a muscular physique that had served him well with the ladies. If he'd followed scripts his entire life, he wouldn't have had nearly as much fun, and with this being his last year in Briar's Mill before college, he was going to have as much fun as humanly possible.

If it had been up to him, he would have gone his entire senior year without working, but with money tight and the kind of fun he had in mind requiring some extra income, he wasn't averse to taking the occasional part-time job. Handing out fliers for the local haunted house attraction was pretty easy as after school jobs went, and since the actual attraction was pretty fucking scary for a local haunt, he had no problem hyping the place up. It wasn't to say that he wouldn't rather be out with his friends Richie and Lucas and Bobby raising some hell tonight, but since the money was good and he knew how to make his own fun on the job, he wasn't too worried about missing out on one last Halloween.

And speaking of fun...

There were two of them, college girls by the looks of them, both of them fashionably dressed in tight, revealing outfits. They weren't costume-ready for Halloween, but definitely looked like they were the kinds of girls who were here more for the pics than the experience the way they were glued to their cell phones. The girl on the left had long, blonde hair and big blue eyes, while the one on the right was Asian, with her jet-black hair cut in a short bob. They were both at least a head shorter than him, and both had everything that would draw a woman to Miguel's attention: huge tits (at least a D-cup on each of them), and tight, round asses.

Sidling up next to them was one of the easiest things Miguel had ever done in his life.

"Hello ladies. Looking to get scared? Mortuary of Doom Haunted House tickets are still on sale, but they're going fast..." he said, holding a flier out to the blonde.

"No thanks; I didn't come here to be scared," the blonde said with some faint disgust.

Her friend grabbed the flier instead, looking on it with some amusement, "Oh, come on, Tiffany! Live a little; we're only here for the night, and it's Halloween! Why not get a good scare?"

"Because, Sandra, I don't like it, alright?" Tiffany replied, crossing her arms under her impressive breasts. The way her tight, midriff-baring t-shirt hugged them as she hiked her tits up... well, it made Miguel a very happy spectator.

The way she talked, Miguel thought that Tiffany might be a little bit of a ditz, while Sandra seemed like she might be more on the fun-loving side, not to mention the brains of the operation. It was times like this that he loved not having a type, aside from a proclivity towards chestier girls; options were always fun to play around with.

"But it's Halloween! We're supposed to be scared, a little!" Sandra protested.

"I don't have to do what I don't wanna do, alright?" Tiffany shot back.

"You know, you're right," Miguel said smoothly. "You don't have to be scared if you don't want to be scared, and thankfully for you, there's a lot of things you can do in town tonight that are both fun, and hardly frightening. Why, with the proper guide..."

Tiffany smiled, her full lips curling into a grin. "See? This guy knows how it works."

Sandra rolled her eyes. "Well, I'm gonna check out the haunted house. You do what you want, I'm gonna get scared. If you're gonna chicken out and be a bitch about it..."

Miguel knew goading when he saw it, and appreciated the assist from Sandra. Tiffany lunged a hand out, grabbing one of the fliers from his hands.

"Fine, I'll try the stupid haunted house, but if I need fucking therapy after this, you're paying for it," Tiffany said.

"I'll take those odds," Sandra said, looking over the flier before her eyes widened. "Wait a sec, entry to the haunted house is forty bucks?"

"Yeah," Miguel answered.

"No thank you; give me something special, and I'll pay forty bucks, but a small-town haunted house I've never heard of before? Yeah, no, that's too much," Sandra replied.

"Would it make a difference if I told you it was going to a good cause? Because it is," Miguel said, smiling. "Proceeds go to a number of school programs 'round town, with special attention paid this year toward helping revitalize our library's children's section. You wanna help the kids, don'tcha?"

Sandra looked thoughtful. "It does sound good, but... we don't have that kind of money to throw around; we want to be able to spread it around, you know?"

"So, wait, first you wanna go and then you don't wanna go, and all this after you twist my arm into going? Make up your fuckin' mind, Sandy," Tiffany said, annoyed.

Miguel prided himself in his ability to think on his feet, and when he had a couple of hotties on the hook he was more than happy to think even faster than usual.

"Well, lucky for you ladies, you happen to know a bona fide employee of the haunted house in question. I could probably get you in cheaper than that," Miguel said.

"With what, your employee discount?" Tiffany asked.

"Well, that was my plan," he admitted. It was a time for a big play, one that could either backfire tremendously, or work out very, very well. "Though if you want to try to talk me into getting you in for free, I'll listen."

Tiffany, ditzy as she was, didn't seem to catch his meaning right away, but Sandra understood right away. She gave him a look, a difficult proposition in his flowing robe, but must have found his face handsome enough to consider him.

"What did you have in mind?" Sandra asked, raising an eyebrow at him.

"What are you offering?" Miguel returned. Sandra grinned at his confidence, while Tiffany appeared to be racking her brain for what they had to offer.

The blonde snapped her fingers. "Ooh, I got it! We got some really, really hot pics; will that be enough to get us in?"

"They'd have to be some hot fucking pics," Miguel replied.

"Oh, we got hot fucking pics," Tiffany answered, mischievous.

Miguel thought about this. On any other day, this would have been more than enough to get his attention, but it was Halloween and he was on the job. Nonetheless, he was also feeling playful, and there were very few things he wouldn't do for some suitably hot pics. "Tell you what, let's make it a game. Whoever sends me the hottest pic gets in free. Sound like fun?"

Miguel had been counting on Sandra's playfulness, and the busty Asian girl more than delivered when she answered, "Oh, this is going to be *so* fun."

Yeah, Miguel had to admit, there were worse nights he could be working than Halloween.

***

Standing across the street, a handful of Miguel's friends ate ice cream from one of the carnival's street vendors who'd opened up early for the evening and watched the scene unfold as he smooth-talked his way into the good graces of two bona fide hotties. Though this was hardly an unfamiliar sight when it came to Miguel, the unlikelihood of what was occurring still bore noting.

"I don't know how the hell he does it," Jacob Wright said. Tall, blonde and as muscular as he was handsome, on paper he should have understood exactly what worked for Miguel. He had his reasons, though, and his friends understood them well enough to not give him a hard time for it.

He continued, "It doesn't take any thought for him, no consideration, no weighing options, all he does is walk up to them and start talking and then he has them all giggly and in the palm of his hand. It's as easy to him as breathing or walking. I don't get it."

Sadie Fuentes, a petite and short Latina whose fashion sense bordered on somewhere between tomboyish and goth yet was still distinctly her own, looked at her friend across the street and answered Jacob, "Some of us are simply gifted, and that boy there he's among them. Good genes, natural confidence, never had a bad thing happen to him in his life... he's gifted by luck."

"Why can't we all be gifted with that kind of luck?" Jacob asked, envying how easy everything seemed to come to Miguel.

"Not how life works, man. Just roll with the punches and play the cards you're dealt," Sadie suggested.

Jacob sighed, swirling the remnants of his pumpkin ice cream around his cup. "Yeah, like that's worked for me so far."

"Give it time, man. You'll make it work," Sadie said, patting her friend on the back before she came up with what felt like the world's most brilliant idea. "Should we fuck with him? We should fuck with him. I think we should fuck with him. Guys, what do you think of fucking with Miguel?"

"Let's not fuck with him," Jacob suggested. "What's to gain there?"

"Oh, come on, it'll be fun!" Sadie suggested. "A little trick to make him work harder for his treat?"

While Sadie was all for playing a prank, Jacob and their other three friends seemed less enthused.

Sean Donner, a thoughtful and somewhat sad-looking boy with dark hair, replied, "I'm with Jacob. Miguel's having a good time, let's not fuck with it? It's Halloween, and some of us should be having fun without needing to worry about whether or not that fun would last. Besides, he's working and you know he needs the money, and you wouldn't want someone messing with you while you were on the job, would you?"

"It's barely a job the way he does it," Sadie said, blowing some of her dark curls from in front of her eyes, her face betraying that she had to admit Sean had a point. "But... fine, you don't want me to fuck with him, I won't fuck with him."

"Thanks," Sean replied, smiling warmly. By all rights, the two of them shouldn't have been friends; Sean was a quiet, hard worker, and Sadie was a wild child party girl known for finishing as many fights as she had started. Interests-wise, they hadn't much in common, but that didn't stop them from being the closest of friends, especially lately after Sean's breakup. After his girlfriend, Anna, had broken up with him, Sadie had been the best friend a guy could ask for (when she wasn't threatening to burn Anna's house to the ground anyway), a true ally and confidante. In a rare move for her, she was even willing to handle Sean with a fair amount of sensitivity, but that only meant she went harder at the rest of her friends, and even worse toward her enemies.

"But know this," Sadie said theatrically, twirling around and standing before her friends. "There will come a time when all of our minds are one when it comes to whether or not to fuck with Miguel de la Cruz, and on that day, I will strike, oh how I will strike down upon him with great vengeance and furious anger the likes of which he has never seen! Oh yes, there will be striking!"

As usual when Sadie was overly dramatic, this got a fair round of laughter from her friends. Well, to those who understood it was a joke anyway.

"Awww, I wanted to see Sadie strike! She's soooo good at it! Like what she did at Holden's party last year? Or Jones's party last year? Or pretty much any party last year? Man that was one helluva year; lotta cop cars. It was soooooo funny every time... I wanted to see Sadie strike," Hana Nakamura pouted. The busty and more than a little ditzy Japanese cheerleader may have looked the most out of place of anyone in the friend group standing and watching Miguel, but while it may have looked like she traveled in very different circles, she was as beloved and necessary as any of them for the history they had together.

"Next time, sweetness," Sadie said, playfully leering at her old friend.

"Yay!" Hana exclaimed, jumping up and down and splashing a little melted ice cream on her shirt. "Ah, crap."

"I wouldn't mind seeing some of that great vengeance sometime; assuming whoever's on the receiving end is deserving anyway," said Simon Greene, looking a little jealously at Miguel as he worked his magic. The black nerd may not have been as gawky and awkward to the others since he started working out and really buffed up, but his voice was every bit as timid as they were accustomed to.

"Give it time; Sadie will make good," Jacob said, nodding, amused, at Sadie, a nod that she readily returned. While he had always been jealous of Sadie's decisiveness, it was also something that he admired in her, even if it meant one of their other friends was going to get pranked somewhere down the time.

Sean sighed. "I really don't see what you're all fussing about; there's gonna be playtime to go around for all of you tonight. It is Halloween, after all."

"Couldn't get off work at the Camelot?" Simon asked, sympathetic.

"Nope," Sean replied. "Not sure I want to, really. Work's an easy distraction."

Tossing her ice cream cup in a nearby trash can, Hana bounded over and wrapped her arms around Sean in a big and enthusiastic bear hug, yet even her huge tits crushed against him wasn't enough to get a smile. "Awww, come on, Sean, it's Halloween! This isn't time for moping! This is time for fun! You don't need to worry about that b-i-t-c-h that dumped ya, not when you got Halloween and friends like us!"

Sadie shot her a look for potentially opening up one of Sean's fresh wounds, but he looked pretty nonplussed as he extricated himself from the cheerleader's enthusiastic embrace.

"Hey, work's work, what can I say?" he said, noncommittal. "It's too late to ask for a schedule change now, anyway."

"Yeah, but you're only eighteen once, and Hana is right in her way; you should find some way to find your fun tonight. Why not just call in sick and come with me to Becky Hardesty's party? You know it's gonna suck there, but I'm planning on starting and ending some shit to make it interesting," Sadie said, her smile devilish but her meaning vague. Whether she was going after an enemy or just starting trouble for fun was something only she knew, and Sean didn't seem all that enthusiastic to find out.

Simon rolled her eyes at this. "Or you could come to the carnival with the rest of us. Jacob and Blair and Hana and me, we're all gonna hit it up, aren't we guys?"

Hana squealed with joy. "Oh, you know it! I'm probably gonna leave early and be a bit naughty, though..."

With Hana, this was nothing new or noteworthy, though whether she'd pull off her intended naughtiness or go home pouting was another matter entirely. Still, with her sex doll body and can-do attitude, it was best not to underestimate her, as she could be remarkably persistent once she had set her mind to something. There were still stories going around about the legendary shit she pulled after getting pissed off that she lost the Homecoming Queen title, mostly involving her getting caught fucking the Queen's father and the Queen's best friend at the same time.

Jacob, on the other hand, looked rather uncomfortable at the prospect of being out with the others, not that this was anything new or noteworthy either. Noncommittally, he said, "Yeah... I'll just need to get my costume first; no big deal, right?"

"See?" Simon said. "You can be surrounded by friends if you want."

"I can be surrounded by friends anytime, 'cause you guys are awesome," Sean shot back.

Simon retorted, "Well, fine, be with friends and help me conquer the hay maze? I've heard it's hard this year, but I plan on kicking its ass, and some assistance would be appreciated."

Sean laughed a little, and felt good at being able to laugh. "It's all good guys, really. Really! I could use the money, and I like the people I work with. It's really not gonna be that bad for me."

"We know," Sadie said, wrapping an arm around his shoulders and squeezing him purposefully too tight. "We just wantcha to know we got your back."

"Definitely," Hana said, then looking at her phone. "Ah, crap, sorry guys, I gotta get to the mall; I promised Blair I'd help her look after Richie and Lucas and Bobby, and you know how those guys get if they don't get some proper adult supervision. Byeeeeeeee!"