(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.)
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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!"
