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: 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.

Being around Valerie, things felt a lot lighter than they usually did, and although he was certain it was just a heady mix of confusion and arousal crashing into one another, the results weren’t exactly worth complaining over. While his kisses were at first timid to her playful, he caught up to speed fairly quickly, wrapping his arms around her and holding her close while they made out. Her firm, full lips suckled eagerly at his tongue, and in those rare moments they came up to breathe, her big green eyes looked up at him pleadingly.

“It’s not that I’m complaining,” he said, smiling at her. “But I have to ask, why me?”

Valerie smiled at him cutely, then disentangled from his arms and knelt before him. “Well, I’m recently single because my ex was a fucking dumbass, you’re cute as hell, and call it masochistic but I find that crazy tends to attract crazy, and since our looney tunes seem to be playing on the same station… well, I figure we can probably have fun. Want to have some fun with me? You know, to make it a happy Halloween?”

Her voice hitched up as she pouted her final words. Jacob had certainly heard better logic in the past, but looking down at her gorgeous face getting closer to his clothed erection and the sweater that strained against massive tits, and the way her fingers teased at the waistband of his boxers… well, it was fairly difficult to argue with her.

“I’m all for a happy Halloween,” Jacob replied. “It’s kind of what I was doing here.”

“Good!” Valerie answered perkily, pulling his boxers down around his ankles. She was taken off guard for a moment when his eight inches of thick cock fell from his underwear, bouncing off her cheek.

She giggled. “I knew you were a big boy, but this… I can touch it, right?”

“Yeah,” he hissed through clenched teeth, watching as she took his cock into her dainty hands, requiring both to wrap all the way around him.

“Mmm, I love sucking cock. I mean, I love everything about sex, but I love, love, *love* sucking cock, not gonna lie, no sir,” Valerie said, running her hands up to the head and rolling her thumbs gently over the hole at the end. When a bead of precum formed there, she practically squealed, running her thumbs over it and spreading the lubrication around.

“Looks tasty,” she said, leaning in to lick at the precum. Her eyes went wide as she got a taste, lidding over briefly before opening back up again as she squealed, “You *are* tasty!”

“Thank you for the shining review,” Jacob groaned as she trailed her tongue down his shaft, briefly worshipping each of his balls, before coming back up and kissing the head. Jacob hissed at the attention, his head dropping back slightly.

“Oh, definitely! Five stars, highly recommend,” Valerie said, kissing the head one more time, suckling and eagerly running her tongue over it before sucking it into her mouth. Watching her lips part as they sucked his thick head in, Jacob moaned, finding it thoroughly more satisfying to be standing here getting a blowjob from this sexy minx than worrying about his costume choice. No doubt he would stress again soon when he had to go meet his friends, but for now, he was enjoying the treatment.

Valerie approached his cock with the same eagerness she seemed to approach everything with, bobbing back and forth on it until she’d taken the entire thing into her mouth. He felt the head disappear into her throat as she made light choking and gagging sounds on it, but that didn’t stop her from giving a truly amazing and sloppy blowjob. It wasn’t long before she was picking up the pace, her head bouncing up and down on his cock enthusiastically as she gave him what had to be the greatest blowjob of his life.

Looking up at him, she took a breather, kissing and licking the head and smiling at him. “You know you don’t just have to stand there, right? Feel free to really grab my hair, fuck my face nice and hard, use me… like I said, I love sucking cock; I’m perfectly happy being your cocksucking slut if, you know, you keep the power dynamics nice and respectful on the inside.”

“You’re… you’re sure?” Jacob asked. Jacob had felt the need to be more… aggressive, during sex in the past, but between his own indecision and the kinds of girls he tended to date (who were generally more on the mellow side), it was something he had never indulged in. Actually having that opportunity, well, that almost made it feel like his cock had gotten just a little bit harder.

“Yeah, totally,” Valerie replied, kissing his cock before inhaling it once again.

“Alright, if you say so,” Jacob answered, grabbing her hair in both hands and taking control of her head. Behind her big glasses, she looked up at him with the sweetest, most innocent eyes (well, as innocent as eyes could look when someone’s mouth was full of cock), and then he began to thrust in and out. At first he used her face like he was fucking one of his exes, keeping it nice and slow and hoping he wasn’t doing something that she didn’t like, but when she reached up with both hands and grabbed his ass, encouraging him to fuck her harder, he followed her lead. He began fucking her harder, coming to enjoy the sounds as she gagged, the feel of the strands of saliva collecting against his balls as she gave him a properly sloppy blowjob. Valerie’s eyes watered, slightly trailing her eyeliner down her cheeks, but the way she looked up at him she might have been the most satisfied girl in the world.

Not that he too wasn’t about to feel satisfied. Getting to engage his rarely used assertive side on top of an intense blowjob had him feeling ready to pop off, and despite absolutely wanting to savor the moment, he felt it important to warn her.

“I’m… fuck, it’s so good, but I’m gonna cum soon,” he said, almost sounding embarrassed at how quickly this was happening.

Valerie pulled his hands from her hair and extracted her mouth from his cock, smiling up at him with the sweetest look he’d ever seen. “Awesome! Let me take over from here? I need it all over my face, you have no idea how long it’s been since I’ve had a good facial…”

Taking his cock in both of her hands, she began jacking him, using her own saliva and his precum as lubrication as she playfully jerked his cock. Valerie smiled and giggled while Jacob stood there dumbstruck, wondering at his insane luck as she brought him over the edge.

“Oh god,” he warned. “I’m cumming… I’m cumming!”

“Awesome!” she exclaimed, jacking him harder and opening her mouth. Jacob couldn’t hold back any longer, and with a moan he worried might be too loud, he came. The first shot splashed across her lips and cheek, some hitting her glasses and some rolling slightly down her chin and neck, while the next few landed in and around her mouth. As he finished shooting what felt like an insanely large load, she kept jerking him, pressing the head against her lips so she could suckle out the last few drops.

Proudly, Valerie showed Jacob her mouthful of cum, before swallowing it luxuriantly. “Delicious.”

“Thank you,” Jacob replied, a little weakened by a good orgasm, but still standing.

She scooped dollops of cum from her face with her finger, sucking them clean. “So, have you decided on a costume?”

“Pirate,” he answered with surprising swiftness. “I’m gonna go with the pirate.”

“Wonderful!” Valerie replied, continuing to lick drops of cum from her face. “I should get cleaned up, but I’ll be happy to ring you up up front.”

“Awesome,” Jacob answered, enjoying how light and simple everything felt.

“You got plans for tonight?” she asked.

“I’m meeting some friends at the carnival, you know, hang out, see the sights,” he said.

“Well, that doesn’t start for a bit…” Valerie said, pulling off her glasses and licking the drops that had hit them. “And I’m getting off work in a few minutes…”

Though some of his old, destructive thought processes almost fought for attention, Jacob pushed them aside and asked, “You wanna do something before carnival time?”

Smiling and hopping to her feet, she leaned in and kissed him on the cheek. “You, ideally. I’ve got an apartment just down the street from here. What’s say when I finish my shift, I take you there, we just strip off our clothes and fuck like a coupla crazy people, which we kinda are and kinda aren’t, kick Halloween off right?”

There were a lot of variables in play that still needed to be considered, but looking at how unbelievably sexy Valerie was standing before him, and wanting to get much better acquainted with her, Jacob figured that variables could take the night off.

“I’d say, Happy fucking Halloween,” he said, grinning.

***

The front door to Valerie’s small, one bedroom apartment burst open, a now fully dressed Jacob and Valerie intertwined as they furiously made out. It was a small miracle that they managed to get the door closed and locked for how aggressively they were groping and kissing one another, but they managed it well. As his hands reached under her short skirt and grabbed her ass, she leapt up onto him, locking her legs around his waist and her arms around his neck as he easily carried her.

“The bedroom’s to the left,” she said, guiding him poorly around the apartment. “No, not that left, *my* left… I mean, I could fuck you on the floor, but my bed is sooooooo comfy…”

Jacob managed not to drop her as he took her into her small bedroom. It was a cluttered, eclectic room filled with bookshelves and posters, board games and collector’s figurines of various cartoon characters, but most importantly, it had a very large, very comfy looking bed. He set her down on it easily, and began pulling at his clothes while she giggled and squealed, enjoying the show as he got naked.

Jacob enjoyed watching her watch him, as Valerie was considerably less interested in getting completely naked. Sure, she pulled off her shoes, and reached underneath her skirt to tug off her red thong and chuck it to the side, but she made no indication that she was interested in removing her knee-high socks or miniskirt. He worried for a moment that this was all she’d do, and that Valerie would hide from him the mammoth breasts that her tight sweater promised.

He shouldn’t have worried.

Sitting up, she pulled her tight sweater up, exposing toned, lightly tanned abs.

Briefly, the sweater caught on her tits. Valerie laughed, “These things are always getting in the way. Bet you’ve got that problem too.”

She licked her lips, staring down at his cock hungrily. Though she’d already had a taste, the mere sight of it seemed to greatly excite her, a fact that swelled Jacob’s pride to no end.

“Sometimes,” he admitted, reaching down to absentmindedly stroke himself while she struggled with her top.

“Hey, don’t have too much fun there!” Valerie exclaimed, finally pulling off her sweater and tossing it aside. “I want that thing in me at least a couple times here.”

Her bra barely contained a pair of full, firm DD tits, a sight that now had Jacob looking on hungrily. He said, “I’m good to go several rounds.”

“You better,” she said, reaching behind herself and unclasping her bra. Her tits only dropped a little when they were set free, and when she threw her bra on the floor, Jacob finally got to see them bare.

He licked his lips. They were every bit as full as he expected, with dark, firm nipples and modest areolas.

“So, whaddya think?” she asked, reaching up and squeezing her tits, running her thumbs over her nipples and giggling to herself when the pleasure forced her eyes closed.

There were a lot of right and wrong answers, and normally Jacob would have found himself at war trying to ensure that he got the rightest of right answers. Instead of saying anything this time, he climbed over her on the bed and kissed her deeply, enjoying her smile and enthusiasm as she kissed him back.

Grabbing him with surprising strength, she flipped him onto his back and climbed on top of him, making out eagerly as she straddled one of his thighs. She pulled her skirt up just enough so that Jacob could feel her exposed, and very, *very* wet pussy, grinding against his leg.

“You’ve felt what my mouth can do, I wanna know what yours can,” she said, kissing him sweetly before climbing on top of him. She crawled over his chest until she was straddling her head, his head buried under her skirt as she lowered her delicious-looking pussy over his mouth. With a thin landing strip and swollen, moist lips, it might well have been the most perfect pussy he’d ever seen.

“Open wide!” she exclaimed, lowering down onto his face.

Jacob let out a muffled sound of surprise, but with his mouth positively smothered by her deliciously sweet cunt, he was hardly one to protest his circumstances. Valerie ground herself against his face energetically, and he did what he could to keep up with her. She was positively soaked, and it seemed as if she had understated just how horny she’d gotten during their encounter in the changing room. He wrapped his arms around her legs, holding her close as he ate her out, licking and sucking at her enthusiastically. She had such a sweet, distinct taste, a taste he could drink in for quite a while it seemed.

While her pussy was sweet, what was coming from her mouth was far from it.

“Ooh, yes! Lick my sweet and cute little cunt! Suck on that clit, fuck me with your mouth! I wanna get all my juices all over your fucking face and lick you clean because I fucking taste soooo good! Come on, come on, that’s eat, eat my needy cunt, do it, do it…” Valerie moaned, squeezing her tits and pinching her nipples as she rode his face. With his face properly covered by pussy and skirt, Jacob was unable to see such an intoxicating sight, but with his cock rock hard and ready for another round, he hardly needed any more visual encouragement.

Instead, he kept at pleasuring Valerie with his mouth, wanting to pass all of his thanks and gratitude on to her in a singular act of pleasure. This had not started out as a good night for him, but with Valerie’s help it had turned around quickly, and he wanted to make sure she understood his feelings on the matter.

And, well, her pussy tasted really fucking good, and the noises she made were hot as hell, too, so, these things also had a way of offering him some proper motivation.

“Yes, yes, yes, you got it, you got it, keep going!” Valerie whined, grinding more insistently on his face. “You keep doing that and you’re gonna make me cum! You wanna make me cum, don’tcha? Well I cum like a fucking fountain, just so you’re prepared, but you can take it, I know you can take it, because you know what you’re doing, fuck yes, I didn’t know it when I saw you, but I should’ve, because you’ve got it… you’re made for this and we’re gonna have so much fucking fun! I am gonna rock your fucking cock, but I want you to make me cum with your mouth first! Do it, do it, do it, fuck, do it, you’re getting close, theretherethereFUCKING HELL, FUCK, I’M CUMMING! I’M CUMMING ALL OVER YOUR FUCKING FACE! YOUR TURN, JACOB! OH, FUCK!”

She wasn’t lying when she said it was his turn, as when her pussy spasmed against his mouth, she began gushing on his face. It was a sweet surprise, and one he sought to lap up as much as he could, but with her gyrations and the sheer volume, most of it ended up all over his face and neck. Nonetheless, Jacob savored what he could, holding her close as she slowly came down.

Almost at once, it seemed as if animation left her body as she climbed off of him and collapsed on the bed. She lay at his side, panting and kissing him, licking her juices from his face as she curled up next to him. For Jacob, it was a strangely pleasant moment in a day that had seemingly started far from pleasant.

Practically purring, she looked Jacob in the eyes and said, “Well, that was super sweet. I wanna fuck. Do you wanna fuck?”

She pulled her skirt up around her waist and spread her legs for emphasis, not that he would have needed that much additional encouragement. At the moment, it didn’t seem as if there was anything Jacob could have wanted to do more.

Although…

He looked around the room. “You got any condoms?”

She shrugged. “‘fraid not.”

That was unfortunate. Jacob hadn’t had a girlfriend for a bit, and so didn’t have any on hand for emergencies. His usual need to worry was running counter to how much he legitimately wanted to have sex with Valerie, so he tried a different angle, “Are you on birth control?”

“Nope. Bad reactions. I’m quite unprotected,” Valerie said casually, playing with her pussy for his benefit. Jacob groaned at the sight, but was inwardly torn.

“I… I want to, but it sounds pretty risky,” Jacob said, absolutely knowing what the right answer was but finding her raw sexuality overpowering what he used to consider his better instincts.

“So? It doesn’t bother me, I find a little risk fun; I spent too much of my life worrying, and I’m not doing that anymore. Worry’s not gonna have power over me,” she answered, leaning over and kissing him. Reaching down, she slowly began stroking his cock, spreading his precum around with ease.

He groaned at her touch, and while he wanted to tell her that it was a lot more than a *little* risk, there was no denying that she had a certain power over him. The voices in the back of his mind that had dictated so much of his life screamed at him, telling him to consider absolutely everything crazy about this.

But with Valerie, he found those voices easy to ignore.

“Fuck it, then,” he said, rolling on top of her. Valerie squealed with glee, reaching down and guiding his cock toward her cunt. He felt the head pressing against her slick lips, inviting him in.

“Come on, Jacob, do it… fuck me, I need it sooooooo bad,” Valerie whined, looking up at him sweetly through her big glasses.

Pushing forward, Jacob sank his bare cock a couple inches into her pussy. She was tight, and oh so wet, but he knew that already. Even so, never having fucked a girl without a condom before, this was all new territory to him and it felt oh so good. Her face contorted with ecstasy as he continued pushing deeper into her, and soon she locked her legs behind his ass and pushed him in even further. It wasn’t long until he was buried deep inside of her, moaning and looking down in awe at the vixen beneath him.

While Jacob wasn’t inexperienced when it came to sex, he wasn’t an expert either. Everything about being with Valerie felt new and exciting, and as she let up pressure with her legs, letting him pull out of her slightly, he soon began to develop a rhythm that felt good.

“Yes, yes, yes!” Valerie exclaimed, wrapping her arms around Jacob as he fucked her. “I wanted this to be a perfect Halloween, but I didn’t know how perfect it could be! I thought it was just gonna be me having fun at the carnival and then fucking myself silly with a vibrator, but this is the fucking best, thank you, thank you, thank you, Jacob!”

She kissed him deeply, looking up at him with lustful eyes and urging him further.

Grunting, he fucked down into her. “I didn’t… fuck… I didn’t think I’d have fun tonight… I thought I’d still be stuck in the damn costume shop… now look what you’ve done to me.”

Valerie laughed, pulling him in tight as he fucked her. “Oh yeah? You thought you’d have a lousy night? Well I’m glad to change things… I’m *really* glad ’cause it means I get to have fun with a cutie like you and all that cock buried up my tight little pussy… yes, please…”

She purred, leaning in and nibbling on his neck slightly. While the pain was momentarily intense, it only drove him to fuck her harder. He couldn’t explain why, but in addition to his anxiety, all of his common sense had seemed to go out the window. The world outside ceased to exist. There was only him and Valerie, intertwined, slaves to pleasure as they fucked without abandon.