The Lucky Men (Canon)

Credit to chingchangchong69 for helping out with this chapter!

"Fuuuuuuck, you're so fucking good at this now," the blonde playboy groaned from his seated position on a comfortable swivel chair. The vibrations from the music blasting a few floors below where still able to penetrate the office, preventing any would-be eavesdroppers from listening in from the hallway.

Not that Sam Wayne cared all that much.

"Mmm," hummed the vision of beauty, on her knees between his legs. As she looked up to meet his gaze, he couldn't ignore the twinkle of mischief in the blue eyes framed by her slightly darker shade of blonde hair. Pulling her head back from his large, now saliva covered cock, his secret lover gave his swollen head a light kiss. "I have had a LOT of practice," she purred.

"Yeah?" grinned the Wayne scion.

"Yeah," confirmed the sexy volleyball player, giving the underside of his shaft a lick from root to tip. "Plenty of practice with this big..."

She kissed the tip again.

"Thick..."

She took one of his balls into her mouth, sucking it slightly before popping it out.

"Juicy..."

The other ball this time.

"Manly..."

Another lick up his shaft.

"Cock..."

With that, she once more swallowed his throbbing erection, taking through her lips and resuming her ministrations.

"Fuuuuuuck," Sam groaned again, flopping back onto the headrest of the chair as he ran his fingers through her hair. It was all he could do to hold on. "So fucking good."

Isabelle Holland grinned around Sam's cock at the reaction she **** out of him. Hard work really did pay off.

As she continued to bob her head up and down his impressive length, Sam let his head relax back against the head of the chair, letting out a satisfied groan at the Holland girls talents. Maybe he should experiment with the other Holland girls he wondered, that sexy older sister of Jace had recently returned as a teacher, and fuck if her mouth-watering tits hadn't captivated the entire schools attention.

A hard suck from the big titty blonde brought Sam back to the present, as one of her free hands started fondling his balls, a knowing smirk on her stuffed lips.

"You little minx, working my weakness" he jested, loving how her soft delicate hands worked him alongside her warm wet mouth.

Instead of replying to him verbally, she swivled her tongue around his helmet, paying special attention to the underside of his cockhead, making him throb in her mouth.

Another couple more minutes of her slurping on his length, and him stroking her head, he warned her that he'd be cumming inside her mouth soon. Giving a slow blink in understanding, she pushed her head all the way down to his crotch, nose pressed against his stomach as she deepthroated him, gurgling on his cock. At that moment, the tightness of her throat pushed him over the edge, and he shot rope after rope down her throat, which constricted to form and even tighter vice around his pulsing member.

After a few minutes of him getting drained, she finally, slowly, pulled her mouth of him, sucking all the way up, finishing with a loud pop. Grinning at him, Isabelle gave his still hard cock a few pump, before standing up and pulling her panties to the side, getting ready to mount him. "Ready for round 2 champ?" She asked, already knowing the answer as his hands found her hips.

The bass pounded through the soles of James Winchester's sneakers, vibrating up his legs and settling in his chest like a second heartbeat. Strobe lights carved the darkness into sharp, fleeting images—flashes of semi-clad limbs, glittering earrings, and cups raised high. The air was thick with the musk of sweat and the sweet tang of spilled drinks. And of course, the allure of arousal.

James stood rooted to the spot, feeling out of sync with the writhing mass of bodies that crowded the dance floor. He could still feel the ghostly imprint of Reyna's curves pressed against him, her confident movements a stark contrast to his own stiffness. She had been close, very close, her breath hot on his neck as she whispered about Skylar's interest, as she ground her ass into his raging crotch. Then, she was gone, lost in the sea of gyrating forms, leaving behind a cryptic smile and the lingering scent of her perfume.

"Enjoy the dance floor," Reyna had said, but James felt mostly nerves still, having danced with the cheerleader, he felt how out of depth he was in terms of dance skills at this school. Each time he lifted his arms to join the rhythm, they seemed to weigh heavier than before, self-consciousness anchoring them to his sides.

He scanned the crowd, searching for a familiar face, someone who might rescue him from his frozen solitude. That's when he saw her, Anastasia Prescott. Captain of the cheer squad, her presence was electric, even from across the room. Her dark green eyes locked onto his, and a smile spread across her lips. An opening, was the thought crossing her mind. "Hey!" a voice shouted nearby, but James barely registered it. His attention was wholly consumed by Anastasia's gaze, which seemed to beckon him forward, promising something wild and unrestrained by her coy smile.

She moved through the masses with an effortless grace, every step a silent testament to her confidence. A flicker of envy shot through James. How could she be so self-assured while he felt like a deer caught in headlights? "Having fun, Winchester?" A random boy, possibly in one of his classes, clapped him on the shoulder, but James hardly felt it. His world had narrowed to the space between him and Anastasia, feeling like prey in the wild jungle. "Uh, yeah," he managed to say, though his voice was drowned out by the music. "Looks like you've got an admirer!" the boy grinned, nodding towards Anastasia, pushing James forward a little, before heading off in search of his own partner.

Anastasia Prescott was a tide of confidence undulating through the sea of bodies, her every step a testament to sensuality. She navigated the crowd with an ease that seemed almost otherworldly, her body adorned in an outfit that clung to her curves like a second skin, accentuating the ample, wide, sexy shape of her legendary ass. The fabric shimmered under the strobe lights, drawing eyes like moths to a flame. Whispers followed in her wake as boys stared, some with longing and desire, while others looked with envy for whoever would claim her attention tonight. Girls glanced at her with a mixture of admiration and jealousy, their gazes sharp as daggers when their boyfriends or hook-up partners had their attention wandering to the large tight ass moving with each step.

"Damn," a footballer muttered nearby, as Anastasia's presence turned the heat up several notches without a single word spoken.

James stood frozen amidst the chaos, his heart drumming a frantic rhythm against his ribcage. He watched her approach, her gaze locked onto his, and he felt like prey caught in the sights of a huntress. Why her? Why now? Reyna's words echoed in his mind, telling him Skylar was interested, but it was Anastasia moving toward him with purpose in her stride.

"Hey," she greeted, her voice threading through the pulsing music and reaching James' ears like a siren song. "You look like you could use some company."

A flush of heat crept up James' neck as he watched her approach. He noted the playful sway of her wide hips, the sultry arch of her brow as she smirked at him. Every instinct told him to look away, but he couldn't. It was as if she wielded a magnetic power that held him in place, something that likely came from being cheer captain.

"Uh, yeah, I guess," James stammered, his cheeks flushing with heat. His brain buzzed, short-circuiting under the intensity of her dark green eyes. Was it just his imagination, or did the room spin a little slower now?

"Guess?" Anastasia raised a sculpted brow, the corner of her mouth quirking upwards. "I don't do guesses. I know when someone needs me."

She was close enough now that he could smell her perfume—a heady mix of vanilla and something exotic, intoxicating. It drew him in, made him want to lean closer. Her outfit left little to the imagination, and James couldn't help but notice the way it hugged her, lovingly tracing the contours of her body. It was more than revealing; it was a declaration, a challenge to anyone who dared question her allure.

"Everyone’s been talking about the new guy," Anastasia said, her voice low, teasing. "I wanted to see what all the fuss is about."

"New guy" – the label stuck to James like a second shadow since he'd arrived in town. He swallowed hard, trying to find his footing in this unfamiliar script. Why were girls like her suddenly within his orbit? Back home, they wouldn’t have spared him a second glance. Here, they sought him out, danced against him, whispered secrets into his ear.

"W-who says there's any fuss?" James managed, his words tumbling out before he could think better of them. His hands clenched at his sides, unsure where to rest, how to stand, how to be.

"Come on," she laughed, a rich sound that made his insides twist. "Don’t play coy with me, James Winchester. I've seen the looks. You've got something about you."

"Something about me," he repeated, his thoughts spiraling. What was that 'something'? Could he wield it, control it, understand it?

"Sure you do." Her hand found his wrist, her touch electric, guiding his palm to rest on the small of her back. "But let’s focus on now. Let’s dance."

"S-sure," James replied, his voice stuttering a little. What was happening? Girls like Reyna, Skylar, and now Anastasia, they never noticed guys like him back home. "Relax," Anastasia smirked, as though reading his thoughts. "Just follow my lead. What's your name honey." She asked sweetly. As she drew closer, James took in the details, the soft glow of her skin, the way her hair cascaded around her shoulders, framing her face. It was almost overwhelming, the sudden proximity to someone so desired, so vibrant. So oozing of sexual energy. "James," he managed to squeak out. "Let's see what you've got," she teased, her tone light, yet laced with an undercurrent of something more.

'Trust me,"' James thought, his pulse quickening, 'It won't be that good'. Their eyes met once more, and the world seemed to tilt on its axis. James' nervousness mingled with a budding anticipation, a curiosity to explore this electric tension that sizzled through the air between them. 'Is this really happening?' he wondered, his thoughts a whirlwind as Anastasia reached him. Her touch was light on his arm, but it seared through his shirt, branding him with a hunger he hadn't known he possessed, wanting her to continue touching him. "Come on, James," she urged, her lips curled into a knowing smile that promised the night was only just beginning. "Keep up with me," she instructed, her voice a velvet command that wrapped around him. "And maybe we’ll give them something to really talk about."

"Uh, sure," he managed, his reply stunted by the sudden proximity to Anastasia. Her body exuded heat like a flame, and he was but a moth caught in her glow. Her fingers danced along his arm, light and teasing, leaving a scorching trail on his flesh. Each touch sent shivers cascading down his spine, as if she were strumming the nerves beneath his skin, playing him like a finely tuned instrument. His body reacted, a visceral, undeniable tension concentrating in his jeans. He felt exposed, **** under her gaze, and when she noticed the effect she had on him, her grin sharpened, wicked and knowing.

"Seems like you're enjoying yourself already," she purred, her eyes glinting with mischief.

James swallowed hard, trying to find words, any words, to respond. But his mind was blank, his thoughts scattered like leaves in the wind. Her presence was overwhelming, her beauty undeniable, and the way she touched him... so casually, so suggestively, left his heart beating hard.

*Why is she doing this? Why me?* His mind wrestled with the questions, but they slipped away, ungraspable, as her body pressed closer to his. The music pounded in his ears, an insistent drumbeat that now seemed to echo the rhythm of his own racing pulse.

"Trying to give the crowd something to talk about?" he asked, his voice rougher than he intended, betraying the impact she had on him.

"Only if you can keep up," she replied, her eyelids heavy with challenge. "Can you keep up, James?"

His hands, uncertain and shaky, found their place on her waist, tentative at first, but emboldened by the warmth of her skin and the firmness of her curves beneath his fingertips. He was in uncharted waters, swept away by the current that was Anastasia Prescott.

'Focus,' he told himself. 'Don't fucking let this chance slip away.'

But as Anastasia turned around, and her legendary ass brushed against him, sending jolts of desire straight to his core, James realized he was rapidly forgetting everything but the here and now, where the heat of her body promised to burn him alive with pleasure. "Move with me," she breathed, her voice a velvet caress over the cacophony that surrounded them.

As if drawn by strings tied to his very soul, James watched, almost outside himself, as Anastasia's body began to sway. Her hips moved with a fluid confidence that spoke of many dances, many admirers left in awe. The rhythm seemed to possess her, each beat an incantation that summoned the primal essence of movement from within her. "Like this," Anastasia instructed, demonstrating a slow roll of her hips that seemed to beckon him forward. "Trust yourself," she coaxed, catching his gaze with hers, those dark green eyes alight with something wild and untamed.

He swallowed hard, steeling himself against the vulnerability that clawed at his insides. With a breath that trembled on its way out, James let his hands descend, landing tentatively on the curve of Anastasia's waist. The contact sent a shockwave through him, the sensation of her warm skin beneath his fingers grounding yet dizzying all at once.

"See? Not so hard," she said with a chuckle, her tone light but laced with something more, something that whispered of promises and secrets shared in the dark, of a sexual nature. Anastasia leaned in, just enough for her scent to envelop him—something sweet and intoxicating that made his head swim. "Now, follow my lead," she murmured, guiding his hands to rest more firmly against her.

James nodded, wordless, his throat tight with nerves. He allowed her to mold him, her touch reassuring yet commanding. As they found their rhythm together, the world around them began to blur, the other dancers melting away until there was only the two of them, caught in a dance as old as time. "Good, you're getting it," Anastasia praised, her voice barely audible over the music, yet it resonated within him, louder than any drumbeat.

His hands grew bolder, fingers gently contouring the silhouette of her form, tracing the line where boldness met shyness. The fine hairs on his arm stood on end, as though charged by the electricity between them. Each sway of her hips tugged him deeper into the spell she wove with her movements, anchoring him to the present moment, where nothing existed but the touching and flow of their bodies and the pulse of the music.

As the tempo of the music escalated, a new urgency took hold of the dance floor. James felt Anastasia's body press back against him with an intimate insistence. Her ass, the one whispered about in hushed tones among yearning peers, now pushed firmly against the undeniable hardness in his jeans. The contact shot through him like a live wire, every nerve ending alight with the friction of their closeness.

"Feel that?" she murmured, her voice low and teasing. "That's what real dancing feels like."

Her words were like kindling to the flame already burning within him. As if sharing one pulse, they moved together, her backside grinding into him in slow, deliberate circles. His arousal was no longer just a physical reaction; it had become a visceral craving that demanded satisfaction.

"Anastasia," he exhaled, his mouth dry, the syllables of her name dissolving into the charged air between them.

"Shh," she breathed out, her hands finding his and guiding them along the contours of her body. Each movement was a brushstroke painted onto the canvas of desire, a bold declaration of shared lust. He could feel the strength in her thighs as she moved, the suppleness of her waist beneath his touch. With each sway, he lost a little more of himself to the rhythm she dictated.

"Move like this," she instructed, her hips dictating the cadence. Anastasia led him through a dance more intimate than any he'd known. It was as though she was peeling back the layers of his self-doubt, revealing the raw heat of pure sensation that lay beneath. Her body was both the map and the terrain, and he found himself an eager explorer, keen to discover every hidden valley and peak. All that mattered was the pressure of her body against his, the heat of her skin under his fingertips, and the intoxicating promise held within her dark green eyes.

"Keep up, Winchester," Anastasia teased, her tone laced with a challenge as much as it was with seduction.

His senses tingled with the aftershocks of their contact, the anticipation of the next movement keeping him taut with excitement. Their two bodies caught in each other's orbit, gravity pulling them even closer with each passing second.

"Isn't this better than standing on the sidelines?" She flicked a knowing glance over her shoulder, her smile wicked and triumphant.

"Much better," he managed to say, his voice gravelly with the effort of maintaining composure. Inside, he was anything but composed; he was tumultuous, a storm of longing and newfound desire swirling within.

They continued to move, the language of their bodies growing more fluent with each gyration. The feeling of her incredible ass literally stroking up and down the shape of his erect cock through his jeans, was almost overwhelming. James surrendered to the experience, allowing Anastasia's confidence to infuse him with a sense of power he had never known—a power not just over her, but over himself.

The thrumming bass reverberated through James' bones, a primal drumbeat that coursed through his veins. He was adrift in a sea of motion, every sway and thrust of Anastasia's body a beacon drawing him deeper into the tide. Her back pressed against him in rhythmical insistence, her legendary curves a siren's call that left no room for hesitation.

"Feel it, James," she murmured, her voice a velvet caress even amidst the cacophony of the party music. "Give in to your hearts desire.", her hands tracing a path down from his neck to his shoulders, and down his bare arms, igniting fires beneath his skin. She caught his wrists, then, with a deliberate slowness that bordered on ****, guided his hands around her waist to her front. The contact was electric; her heat seeped into him, branding him with a hunger he had never known before.

"Like this," she instructed, pressing his palms against the firmness of her breasts. The pebbled fabric of her top grazed his fingertips, a tantalizing barrier to the softness underneath. His breath hitched as he felt the rise and fall of her chest, her heart racing as wildly as his own.

Anastasia leaned back into him, and James was lost. His world narrowed to the swath of skin where her hips flared out from her waist, the inviting expanse he now cupped with trembling fingers. Each movement they shared was a brushstroke in a masterpiece of desire; her ass, a canvas against which he painted his arousal with every unintentional grind.

"James..." She tilted her head back, resting it on his shoulder, giving him a view of her profile etched in shadow and light. "You're holding back. Don't."

He wasn't just holding back; he was clinging to the remnants of who he had been before this moment. But Anastasia, with each pulse of her body against his, dismantled his reservations piece by piece. The air around them seemed to shimmer with the intensity of their connection, the rest of the partygoers fading into mere background noise. "Ana...stasia," he breathed, his voice a hoarse whisper as he surrendered to the rhythm she dictated. His hands roved with newfound boldness, tracing the contours of her body, mapping the geography of a landscape he yearned to explore further.

"See? Just move with me," she coaxed, her words punctuated by the roll of her hips. They were locked in an intimate dance, their movements a language spoken in the silences between beats. As if by some unspoken signal, the space between them diminished further, until there was no distinction where he ended and she began. Their bodies moved in perfect harmony, a symphony of need and desire played out on the crowded dance floor. "Nobody else matters right now," she whispered while grinning, feeling as if her plan to steal Skylars new pet at her own party was almost completed. And James believed her, because in the span of a song, Anastasia had become the focus of his entire world that night.