Once Upon a Halloween Ch. 02

(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: As a reminder, this story is 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.)

***

You wouldn't have known if you just glanced at 18-year-old Jacob Wright as he wandered down Main Street on Halloween night, but he was in hell. All holidays where something was expected of you managed to do this to him, but Halloween was one where this feeling was exceptionally pronounced. None of this came from fear of monsters and ghosts, and it wasn't from any negative memories from his childhood chasing him. He was quite fearless in many respects, and he had a wonderful and loving family who had always tried to do the best for him, but this didn't stop his hands from shaking and a slight sweat from breaking out on his brow as he considered what he had to do.

For a boy as handsome and accomplished as Jacob, you wouldn't have imagined this of him on sight alone. After all, he was senior class vice president, on the honor roll (aiming at valedictorian if Blair didn't beat him to it), and a star on the school's state champion water polo team. At 6'2" of toned muscle and with well-trimmed blonde hair and a stubble that actually looked on purpose, he had movie star good looks and a warm smile that made him popular with the girls at Briar's Mill High School. That he didn't seem to date was a matter of much debate and discussion outside of his friend group, but there was one simple reason that he kept close to his chest out of simple embarrassment.

In short, Jacob Wright was plagued by indecision.

To him, life was an equation, one where there was always one right decision and a million wrong ones, and the possibility of choosing wrong petrified him. It was a philosophy that had generally worked for him when it came to matters like academics or sports, because there the goals were always tangible and distinct. When it came to everything else, however, the calculations of variables overtook his better instincts and drove him to anxiety. At his family's insistence, he had been seeing a therapist for close to four years now, and things had gotten better, even if they hadn't fully conquered the fear just yet. It made it easier to have friends and enjoy his extracurriculars, even date a little here and there (though, inevitably, his indecision would find a way to screw things up on that front), but some things were still close to impossible.

Holidays were close to the top of that list for bringing about anxiety. There was always the right gift to find, the right decoration to place, the right food to prepare and the right customs to observe, and if you got one detail wrong, it would disappoint a lot of people you cared about. He couldn't handle that, and if he could have, he would have retreated into his room and hidden like a turtle until things were done.

The problem, was, he couldn't do that this time. Not when he'd promised the others he'd meet them at the Halloween carnival. Not when he'd promised he'd come in costume, even though he hadn't already picked one out.

Cursing himself for making such a promise with uncertainty in place, he balled and unballed his fists, walking down Main Street, past excited children and parents and decorated windows, past the Camelot Theater where Sean was no doubt preparing for the yearly showing of Halloween, past the ice cream shop and the IHOP, down to Baxter's Rare Clothes, the costume/vintage clothing shop whose very presence had given him this anxiety.

Theoretically, all he had to do was run in, grab something, then run out, and that would be it, right? Just grab the first thing within arm's reach and let that be that?

No, nothing was ever that easy. This was their last Halloween in high school after all. Most of them were going to be headed to college next year, and he couldn't ruin anything for his friends.

While it was this pressure that brought about his anxiety, it is also what made him steel himself into pushing open the door and stepping inside the shop.

As he took in the store with wide eyes, Jacob recognized one simple and nightmare-inducing fact: if choices were hell, then Baxter's Rare Clothes had to be close to hell's hottest circle. A store that had been in business for close to forty years after old Mr. Baxter, a former Hollywood costume designer, retired to Briar's Mill with a warehouse's worth of movie costumes in tow, Baxter's was a cramped and chaotic battleground featuring racks upon racks of costumes, props and vintage clothes that had since been donated by the residents of Briar's Mill. Coupled with the off the shelf costumes that you'd find in any average Spirit store just hanging on hooks throughout the shop, and the options were seemingly limitless.

"Fuck..." Jacob groaned, annoyed. "Why'd I have to come here... why'd I have to make any promises... and why the hell does a small town have such a big year-round costume shop? I mean, seriously, what kind of sense does that make?"

The one thing he was thankful for was that, with most people having already picked their costumes out for Halloween night, the store itself was mostly empty. Sure, there were a couple of idle window shoppers looking to kill some time without any intent of buying or renting anything, and a couple of employees no doubt around somewhere, but being able to have some peace while dealing with his issues was certainly nice. The cheery yet spooky Halloween music, the good vibes in the air... that was definitely something that took a little of the edge off.

"You can do this... you can do this..." he murmured to himself, finishing with, "Eventually. Eventually always happens, you'll make this work..."

Finding some strength in the bouncy tune of the Ghostbusters theme kicking in over the shop's speakers, Jacob was fairly certain that he'd worked out a strategy. He would methodically pace the store, making a list of every costume that he certainly couldn't wear, and then make appropriate pro/con lists for everything that would remain. That, certainly, wouldn't take too long, and he'd certainly have enough time to make it to the carnival to meet with Blair, Simon, Hana and the rest... yes, this would be possible. He could do this, he could make a system of this, he could...

He could stop in somewhat slack-jawed surprise at what he saw in the last aisle.

Velma, from Scooby Doo, was dancing. More appropriately, she was dancing to the Ghostbusters theme like nobody was watching, which, until he'd rounded the corner was probably accurate. She wasn't a very good dancer, but was having so much unrestrained fun that Jacob still couldn't help but feel jealous of her.

Of course, he knew it was a girl in a Halloween costume, and one who was a damn sight cuter than her cartoon counterpart. At 5'6" and with a tight body, the knee-high orange socks, red miniskirt that showed quite a bit of thigh and orange sweater (with a neck she'd pulled down to expose her slightly tanned and very bare shoulders) looked good on her. Looking a couple years older than Jacob, her generous ass and bust made the already tight garments look even tighter as they bounced lusciously with her every fun, if ungraceful move. It was her face that really got his attention, though. Framed by a period appropriate bob of the girl's jet-black hair, her face looked so cute she actually bordered on sweet, with pouty lips and dimpled cheeks.

She smiled as she danced, her eyes closed behind her big, black, thick costume glasses, looking freer than Jacob might have ever felt. His jealousy of her strengthened, but that was far from the only thing that strengthened at the sight of her.

Opening her eyes, she saw him and startled, nearly falling over from surprise but catching herself.

"Jinkies, you nearly scared me half to death!" she laughed, her voice high and light and cheerful. Putting a hand to her chest, her fingers briefly toyed with the nametag pinned above her left breast before she asked, "Are you looking for a costume, cuteness?"

An answer. She wanted an answer. What was he going to say? Of course, he was in a costume store on Halloween quite obviously not wearing a costume, what else was he going to say?

After a brief moment remembering what words were, he answered, "Uh, yes."

"Then I'd say you've come to the right place, 'cuz we got oodles upon oodles of costumes!" the girl exclaimed, practically skipping down the empty aisle toward him. "I'm Valerie!"

She pointed to her nametag for emphasis, and continued, "And I'll be happy to find you the perfect one just in time for the big night!"

Smiling faintly, glad to have a guide on this journey who might help him find the right option, he said, "Thank you."

"It's my pleasure, helpin' out a cutie like you!" she said, bouncing down the aisle. "Oh, and my job, too, I guess. But, you know, if you take pleasure in your job then it's barely a job, and I don't like ordinary jobs, so... letsgofindyouacostume!!!"

Turning back to him, looking slightly worried, Valerie added, "And please don't tell my boss I called you a cutie? We're supposed to keep things strictly professional, but it's Halloween and I can't exactly contain myself because this is one of the best nights of the year, and... well, you get the idea, right? You won't tell on me? Please? Pretty please?"

Though still quite confused, Jacob replied, "I wouldn't even know who to tell. And I also wouldn't."

Valerie's face lit up again as she went back to bouncing down the aisle. "Wonderful! Thanks! Come on, let's get you started and find you the perfect costume! What's your name cut- I mean, valued customer!"

He looked around, wondering just who she was afraid of being overheard by and finding the store quite empty, save for the overstuffed racks of costumes and vintage clothes that threatened to crush them.

"Jacob," he answered.

"Excellent. And what kind of costume are you in the mood for, Jacob, because lemme tell you, at Baxter's here, you are positively spoiled for choices! We've got cool, we got sexy, we've got scary! We've got screen ready and cheap, cheap, cheap! We got so many options your mind will probably explode!" Valerie exclaimed perkily, completely unaware of the personal hell a phrase like that put Jacob into.

"Ummm..." Jacob said, feeling his hands start to shake.

Valerie looked at him, and her face lost some of its prior perk. Her smile returned almost as quickly, however, as she asked, "So, would you be interested in buying a costume, or renting? I guess that's where we should start first!"

Jacob hadn't thought about this, but he found that looking at Valerie made it a lot easier to think about options. "What are the pros and cons of these options?"

"Well, buying means you get to keep the costume of course, so that's a pro. That and nobody having ever worn it before," she said, pointing to one of the off the shelf Halloween costumes that could have been bought at any store. "The problem with that, though, is that they're more expensive than a rental, and of lower quality."

That made the choice simple. He said, "Alright, what do you have in the way of rentals?"

"Now we're talking!" Valerie cheered, grabbing him by the wrist and pulling him down a nearby aisle. She was a much smaller girl than him, but he doubted he could stop her even if he was inclined to. As she looked him up and down, mentally taking his measurements, she would take him from one area of costumes on hangers to another, before zeroing in on an area she thought fitting.

"Alright, with your muscles a lot of our stuff's going to be on the tight side, but I think we can make something work for you. Would you say you want something scary, or something cool?" she asked, considering him. "You strike me as a guy who'd do well with the cool look, but that's just my opinion."

If Jacob didn't know any better, he could've sworn that she understood exactly what was going on with him. Maybe it came from being just a real good salesperson, or an overly sensitive sense of empathy, but he was appreciating her presence more by the moment.

"Cool works," Jacob agreed.

"Perfect. So, do you wanna go more good guy, or do you wanna go more bad guy? Because you got the good looks to pull off good well, but I think you could make a surprise bad boy pretty easy, catch people off guard and all that," she said, looking him up and down quietly and giving him a chance to make one of his own decisions. Though it was still difficult, especially with what felt like several casual come-ons from her part, Jacob found the words coming with more ease than usual.

"Somewhere in the middle, I think," he said.

"Ah, someone morally gray who could shake out one way or another depending on the needs of the story, keeping people in suspense until the last minute... but still probably leaning toward the side of good, I'd wager," she said, stroking her chin as she looked at the racks of plastic sack covered costumes. Looking at the bare expanse of her neck, and her shoulders, Jacob was once again taken by how beautiful she was, and found a rather annoying stirring in his pants that might threaten to make things a problem. Shifting to the side slightly, he hoped his jeans would cover things well enough.

"Do you trust me?" she asked.

"I don't know you," he admitted. "But I trust that you know this, because I sure as hell don't."

"Then how about I make some selections for you? I've got a few ideas that'd work with your... impressive build, and your general aesthetic, and I think one of them could prove a perfect Halloween costume for you if you just try them on," Valerie explained, looking up at him with big green eyes that practically challenged someone to say no to her.

Glad to have a decision taken out of his hands, and hoping that she had as good taste as he hoped (even if he was taking this completely on faith, and possibly being a little addled from her being so cute), Jacob said, "Hit me with your best shot."

***

Standing in the small changing room with its wall-sized window and narrow bench, Jacob considered her best shots and found himself troubled. Valerie had done a wonderful job of paring down the various options into looks that would both fit him and work for the parameters that he'd established, but that didn't stop the simple fact that he was still looking at two costumes of similarly high quality and found himself torn by not wanting to screw up.

On one hook, there was a cowboy costume. On the other, a pirate costume. Like most of the rental costumes at Baxter's, they were screen ready, high quality and just cool enough that he would look good without necessarily standing out. He could see himself wearing either of them, but instead of actually wearing one, he stood in his boxers and undershirt, looking at them.

"How ya doin' in there?" Valerie asked from outside the door. "Either one calling out to you?"

"No," Jacob admitted.

"Well, if they don't reach you, I can find another," Valerie offered.

"No!" he yelped, then calming his tone. "I think that'd make the problem worse. They're both good costumes, I just can't pick the right one."

"There's no right or wrong, you know. It's Halloween! It's about what's fun!" Valerie said.

"I know, but that doesn't mean there isn't still a right and wrong about how to have that fun," Jacob said. "Like, there's a certain appeal to the idealized lifestyle of the open frontier implied by the cowboy costume, but would I also be implicitly supporting the horrors committed by said cowboys toward the indigenous populations that came with westward expansion if I did so? On the other hand, pirates were known as some of the earliest seeds of democratic leadership in the modern world, which is admirable, but they were also violent criminals... there's just too many variables to consider..."

There was a pause from the other side of the door before Valerie said, "You're breathing in there, right?"

"Yeah," Jacob replied.

"Is it helping any? Taking a second, breathing deep, trying to expel whatever's holding me up, it's helped me with anxiety in the past," Valerie said.

"No. I breathe because I have to, it's not really helped me with decision-making in the past," Jacob explained.

"Huh. Okay, I should say that it's just a Halloween costume and no big deal, but since that's got every chance of making things worse on you, I won't," Valerie said.

"Thanks," Jacob replied.

There was silence from the other side as she thought about this. "Can I come in?"

Looking down at his half-dressed state, and the semi-obvious erection that had been around ever since he'd met her, Jacob replied, "That probably wouldn't be a good idea."

"Oh, I know that; I'm supposed to stay out here and keep an eye on things even when there's basically no one here and I've got coworkers who'd cover things, but you're in crisis, I can tell, and I think it might be easier to help you deal if I can talk this out face to face," Valerie said.

Her logic made sense. "I'm... not fully decent in here."

"So? Wouldn't be the first time me seeing something like that around here," she replied.

That was of little comfort, honestly, but since it didn't help his indecision any, Jacob relented. Sighing, and flexing his hand, he unlocked the door and said, "Come on in."

She stepped inside, closing and locking the door behind him, and then getting in close. The changing room was quite small, and close was about the only option for proximity between them it seemed. Valerie looked up at Jacob, biting her very, very nice lower lip and looking up at him with her big eyes. He could almost feel the heat coming off of her in this proximity, and found the only way he could keep his large erection from being the center of attention was hoping that she wouldn't notice it.

"I'll be honest. I don't have a cure for what you're going through, and while I may not have dealt with your flavor of anxiety, I know at least a little of what you're going through. Even though I know I don't know everything, I know three things here for sure," she said.

"Oh? And what are those?" he asked.

"Well, one, that you haven't been able to take your eyes off me since you entered the store," she explained.

"I'm sorry-"

"Don't be sorry, I like you looking at me," she said, smiling up at him sweetly. "Because it goes with the second thing I know, and that's that I think you're really, really cute! Most guys as good-looking as you got some serious attitude and superiority shit, but you, you don't let it give you a big head, and that's a really good look."

Jacob blushed. It managed to silence the anxiety for a moment, so, blushing was a definite improvement, even as she took half a step closer to him. "And what's the third thing?"

"Oh, that?" she said, looking down. "It's that you've got a pretty big cock, and that I really want to know what it tastes like."

He nearly choked after hearing what she said. No, he couldn't have heard her right, could he. "Wha-"

Before he could get another word, another objection, another fear out, she closed the distance between the two of them and kissed him. Her kisses were eager and playful, and though there was a lot inside of him that wanted to fight this, to question this, to determine the optimal path forward, in the end he found it a lot easier to kiss the hot shop clerk.