Once Upon a Halloween Ch. 02

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.