Dean didn't really understand Sam's aversion to Halloween. I mean yeah, the fact that people turned monsters that could rip you apart into jokes was a little annoying when you'd tackled the real thing before.
That was a minor price to pay, in Dean's humble opinion, for all the fun stuff. Namely, the fact that Halloween was the one day of the year that encouraged girls to wear slutty nurse costumes outside of a strip club, and that was definitely something Dean approved of.
Which was why he was at a bar, historically the best place to see that most delightful aspect of Halloween. Not one to ignore tradition (especially when it increased his chances of getting laid), he was proudly wearing his leather jacket, a white t-shirt, and blue denim jeans.
"So what're you supposed to be?"
Looked like it was going to pay off.
"James Dean," he answered, turning on his barstool to smile at the the dark-haired girl who had asked the question. He gave her an obvious up and down scan, "Officer."
She giggled, and Dean couldn't help the way his eyes were drawn downward to the glint of the fake badge pinned to her chest.
"Can I buy you a drink?" he offered, and she nodded, shuffling closer.
Three drinks and a lot of heavy flirting later, Katie, as she had introduced herself, was leaning heavily against Dean, her chest pushed against his arm and her ankle hooked around his.
"So," she purred, running her hand up his thigh slowly, the touch sending shivers of anticipation down Dean's spine, "What do you say to the idea of me taking you outside and frisking you, hm? I gotta feeling you're the kind of guy who's done a few very bad things, aren't you, Dean?"
"Yes, Officer," Dean answered immediately, licking his lips and grinning. She grabbed a fistful of his jacket as she slid off her barstool, leading him down from his and through the bar until they reached the back door and slipped outside.
Dean was a little surprised when she shoved him against the wall facing away from her, hands up against the rough brick wall, and he had only enough time to glance over his shoulder before she was kicking his legs apart and pressing against his back.
"Told ya I was gonna frisk ya," she hummed in his ear, sliding her hands around him and digging her fingernails into his abdomen gently, the blunt pressure making Dean's muscles twitch.
"Yes ma'am," Dean breathed, taking small, shallow breaths as she slid her hands lower, tracing over his hips and down his thighs, crouching as she went so she could follow his legs all the way down to his ankles. She turned her hands inward as she want back up, sliding along the inseam of his jeans and Dean's breath caught in his throat as her palm slipped between his legs, cupping his balls before slipping her hand forward over his dick and giving it a squeeze.
"Oh my," she breathed, rubbing carefully, "What have we got here? Concealed weapon for sure."
She giggled at herself as her hand dropped away and she straightened, lifting her hands to run down his shoulders and down his back, stopping at his ass and giving a little moan as she gripped his firm cheeks in her hands.
"What have we got here?" she purred, sliding her hand into his back pocket, the foil of the condoms he had stowed there crinkling between her fingers, "Ooo, always prepared, aren't you? Such a good boy scout."
She ripped one off before pushing the others back in his pocket, and Dean smirked as she gripped his shoulders and spun him back around, body thrumming with arousal and his cock aching against the seam of his pants.
"Pays to be prepared, that's what they say," she smirked as her fingers when to his zipper, and Dean pulled her in against him, kissing her thoroughly.
She made a pretty little sigh of sound against his lips, fingers still working on his pants and he moaned, sliding his hands under that tiny skirt of hers and cupping her ass through the lacy panties he found there.
She pulled her mouth away on a pant as she finally got his jeans undone, and he went for her throat instead, mouthing and nipping at the warm flesh more than happily.
"Now now," she breathed, pushing him away and Dean's heart sped up as she sank to her knees, smiling up at him deviously, "Still have to check on that concealed weapon, don't I?"
Her hands dipped deftly into his boxers, getting his cock out and Dean's heart fluttered. She ripped the condom packet open, and his eyes widened as she popped the tip of it into her mouth and gripped his cock to guide the tip into the little ring of latex.
"Oh fuck," Dean groaned, the condom rolling smoothly down his shaft with her mouth, and she glanced up at him, smirking around his length between her lips before fucking going to town sucking and bobbing her head like a fucking pro.
Dean's head thunked back against the brick, the twinge of pain from the impact completely overrode by Katie's hot mouth. He slid his fingers into her dark hair, loosely gripping the silky strands and just holding on for the ride as her tongue flicked and rubbed against the tip of his dick, shooting sparks of pleasure through him.
He bit his lip, whining breathily as she suddenly pulled off, the wet snick of her lips coming off the tip of his dick making it twitch. He pulled her up his body immediately, one hand still gripping her hair and the other her arm, using the leverage to mash their lips together as he spun them around to press her against the wall.
He considered the fact that he hadn't had the chance to feel those gorgeous tits yet a personal crime, and he took the time to do it then, her tongue licking so sweetly into his mouth and her legs spread for him already. She moaned as he rolled her nipples through the laughably thin fabric of her costume shirt and the lacy bra underneath.
He kept one plush breast cupped in his palm as the other hand pushed her skirt up, dipping between her legs boldly to rub against her mound, making her bunch his jacket in a tight grip and her excited squeak press against his lips.
"Oh fuck," she panted desperately against his lips as he slipped his fingers under the waistband of her panties, rubbing against her clit with tight, firm circles that had her shaking and writhing in no time at all.
Finally she grabbed his hips, pulling him forward at the same time that she hiked her leg up as high as she could around his waist, and Dean was not the kind of man to miss a hint.
Hefting her up easily, he pressed her tight against the wall as she squeezed her hand between them to push her underwear aside and guide his cock into her slick heat.
They both moaned as he sank in deep, pleasure racing through Dean's veins and driving his hips, guiding the fast, sharp thrusts.
"Oh fuck, that's it," she groaned, sliding one hand up into his hair and gripping tight as the other twisted some of his jacket between her fingers, hips grinding downward into Dean's thrusts heatedly.
Dean groaned, sucking and licking her neck as he fucked her, her juices smearing across his pelvis and the front of his jeans obscenely and fuck.
"Oh fuck, oh fuck," she panted suddenly, hand pushing between them again as she rubbed her clit frantically to finally push her over the edge.
The back of her hand grated against his abdomen, and Dean bumped hard against it as her fluttering, tightening pussy around his dick rocketed him straight over. A strangled sound left his throat, his hips grinding forward tightly and weakened knees threatening to dump them both onto the ground.
It was only a matter of moments that they remained frozen, the loose, shivery feeling of their orgasms countering the motivation for any movement at all. Finally Dean grinned against her throat, pulling his head back enough to look at her flushed, orgasm-hazy daze and feeling his pride swell even as his dick began to soften.
"So, Officer," he teased with a smirk, "Want to take me downtown for further questioning?"