It was Christmas night, the city blanketed in a soft glow of twinkling lights and lingering holiday cheer. Snowflakes drifted lazily outside, but inside Derek Hale’s sleek penthouse apartment, the air was already thick with tension.
Earlier that evening, Derek had picked up the phone and dialed his best friend with a casual tone that hid the storm raging inside him. “Yo, Jackson. Holiday’s too quiet over here. Come through for drinks—bring Stiles. Got some good wine and cake. Let’s celebrate properly.”
Jackson’s voice had lit up instantly. “Hell yeah, bro. We’re on our way. Stiles’s gonna look fire tonight—trust me.”
Stiles, curled up on the couch in their apartment, overheard every word. Her stomach twisted. She didn’t want to go. Not to Derek’s place. Not with those dark, hungry eyes that always lingered too long on her body, stripping her bare even when she was fully clothed. But when Jackson hung up and turned to her with that possessive grin, asking, “You cool with that, baby? Derek’s place for drinks?” she forced a sweet smile and nodded. “Sure, baby. Sounds fun.”
Jackson’s eyes sparkled with mischief as he disappeared into their closet, returning with the sluttiest red dress she owned—a barely-there mini dress made of shimmering satin that clung to every curve like a second skin. The neckline plunged dangerously low, threatening to spill her massive tits with every breath, and the hem barely skimmed the tops of her thick thighs. “Wear this one, bb,” he said, tossing it onto the bed. “And no bra. No panties. Let’s make it a real holiday gift.”
Stiles’s cheeks flushed hot. The dress was obscene—she’d only worn it once before, to a club where Jackson had spent the night groping her on the dance floor. Going commando underneath? That meant every shift, every breeze, would remind her how exposed she was. Her fat pink pussy would be completely bare under the thin fabric, one wrong move away from flashing everything. But she nodded obediently, slipping into the dress while Jackson watched, his gaze raking over her like he owned every inch. The material hugged her huge breasts, nipples already hardening against the cool satin, poking out visibly. The hem rode up as she moved, teasing the curve of her ass cheeks. She looked like pure sex wrapped in holiday red.
The entire car ride to Derek’s place, Jackson couldn’t stop bragging. One hand on the wheel, the other resting high on Stiles’s bare thigh, fingers inching dangerously close to her uncovered pussy. “You know Derek admires you, babe. Like a little sister or some shit—always asking about you. But deep down? Dude’s jealous as fuck. He’s never gonna pull a girl like you. Look at you—tits spilling out, ass fat enough to make any man lose his mind. And that pussy?” He chuckled, sliding his fingers higher until they brushed her smooth, hairless lips. She was already a little wet from the exposure, and he smirked. “Bare and ready under this tiny dress. Derek’s gonna be hard all night just looking at you, but he knows you’re mine.”
Stiles shifted uncomfortably, thighs pressing together as Jackson’s fingers teased her slit. She hated when he talked like this—especially about Derek. But she stayed quiet, staring out the window at the snowy streets.
When they arrived at Derek’s luxury building, the doorman waved them up. Derek opened the door himself, and the moment his eyes landed on Stiles, he froze. The air left his lungs in a silent rush. She was breathtaking—porcelain skin glowing against the sinful red dress, massive tits heaving with every nervous breath, nipples straining against the fabric like they were begging to be sucked. Her thick thighs pressed together, the hem of the dress riding so high he could almost see the shadow between her legs. No panties. He could tell. Fuck.
Jackson clapped him on the shoulder, breaking the spell. “See, Derek? Told you my girl dresses like a proper slut for the holidays.” He laughed, pulling Stiles inside by the waist, his hand dipping to squeeze her ass possessively.
Derek swallowed hard, forcing a smile as his cock twitched painfully in his jeans. “Yeah… damn. Come in, you two. Got cake and wine ready.”
He led them into the open-concept living room—dim lights, a roaring fireplace, soft R&B playing low. A decadent chocolate cake sat on the coffee table beside a bottle of deep red wine. But it wasn’t just any wine. Derek knew Jackson’s weakness—he bragged about holding his liquor but always tapped out fast. So he’d chosen the strongest bottle he had, high-proof and potent, pouring generous glasses without a word.
They settled on the plush sectional: Jackson in the middle, Stiles tucked against his side, Derek across from them. Stiles squirmed immediately under Derek’s gaze. He wasn’t even trying to hide it tonight—those dark eyes raking over her body, lingering on her hard nipples, tracing the way the dress barely covered her thighs. Every time she shifted, the fabric rode higher, and she had to tug it down, hyper-aware of her bare pussy rubbing against the couch.
Jackson downed his first glass fast, already loosening up. “This wine hits different, bro. Good shit.” By the second glass, his cheeks were flushed, words slurring just slightly. And then the bragging started.
“Man, you should’ve seen Stiles last night,” he said loudly, arm slung around her shoulders, fingers toying with the strap of her dress. “Had her screaming my name—‘Jackson, harder, please!’ Begging for it rough like the little slut she is.” He squeezed one of her tits through the dress, making her gasp softly. “These tits? Bounce so perfect when I fuck her from behind. And her pussy—tight, pink, grips me like it never wants to let go. I had her squirting all over the sheets.”
Stiles’s face burned crimson. She squirmed harder, thighs clenching as she felt Derek’s stare intensify—hot, angry, hungry. He was gripping his glass tight, jaw clenched, lust and fury warring in his eyes. He hated this—hated how Jackson talked about her like she was just holes and curves, a toy to brag about. But god, the details only made him want her more. Imagining her screaming, begging, that fat pink pussy dripping…
Jackson got louder with every shot, voice echoing in the room. “She loves it when I slap her ass red—leaves handprints for days. And when I make her ride me? Those big tits in my face, nipples in my mouth… fuck, she cums so hard she shakes.”
Stiles wanted to disappear. She could feel her pussy getting wet despite herself—from the humiliation, the exposure, Derek’s unrelenting gaze on her thighs like he was imagining spreading them wide.
Finally, Derek cut in, voice low and controlled. “Hey… let’s keep the holiday spirit going. How about truth or dare? Been a while since we played something fun.”
Jackson laughed, already tipsy enough to agree instantly. “Fuck yes. I’m in.”
The first few rounds were light—silly truths about embarrassing childhood stories, dumb dares like chugging wine or doing push-ups. Jackson dared Derek to down a full glass in one go, laughing as Derek obliged without flinching. Stiles picked truth twice, answering softly about her favorite holiday memory, her voice sweet even as she tugged nervously at her dress.
But the wine was hitting Jackson hard now—eyes glassy, words slurring more. He was still awake, still laughing, still the loudest in the room… but not for long.
Derek poured another round, his dark eyes flicking to Stiles. The game was just getting started.
And the night was about to get a lot filthier.




















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