"Y/N, sweetie, are you almost done?" your roommate called out from behind your bedroom door, her tone noticeably excited. "They'll be here any minute!"
Her spirit prompted a smile from you. "Just getting ready, Jess."
You had just gotten out of the shower and were already dreading the night ahead. Your roommate Jess was a big fan of throwing intimate dinner parties and trying to set you up with any guy she invited to those little shindigs. Tonight wouldn't be any different, as her boyfriend Sam was supposed to bring his brother, Dean. A guy she tried—and failed—to set you up with, time and time again.
He was always this blatant egomaniac, laughing a little too loudly at his own stupid jokes and witty remarks. To which you would always roll your eyes and replenish your wine, taking a nice, big sip to make the night a little more bearable. Of course, you had to admit it—he was the most handsome man you had ever laid eyes on. But all of that meant absolutely nothing as soon as the man opened his mouth.
Running an absentminded hand through your hair in your brooding, you heard a series of impatient knocks on your door.
"Yes, Jess," you said, opening the door before her knuckles could touch the wood again.
She smiled. "Wear a dress, sweetie. It'll look so much nicer on you."
"Do I have to?" you asked.
"Yes," she simply stated with a resolute nod. "Now, hurry up. Sam and Dean should be here soon."
Closing the door on her, you took out the first dress you could find. Touching up your makeup and slipping on a pair of flats, you deemed yourself good to go.
Throwing a quick compliment your way while you descended the stairs, Jess ordered you to light the candles and stir the pots and pans in the kitchen while she hurried to open the door.
Excited chatter soon emerged from the hallway, growing closer and clearer as you strained the pasta.
"Go say hi," Jess told you as she entered the kitchen, taking the bowl out of your hands and gently nudging you toward the door.
You gave her a sad look as you brought your hand down to rub your stomach. "I'm suddenly not feeling all that well, Jess."
"Oh, please," she waved you off without a single glance. "You're fine. Now, go."
Gathering your composure, you found the two men seated in front of the television, entranced by a rerun of Friends. They seemed to be pretty well instructed by Jess—both dressed to the nines, wearing their best suit jackets, not a hair out of place. Turning their heads as you cleared your throat, Sam quickly stood to engulf you in a tight hug.
"Nice to see you again, Sam," you sweetly sang, your smile fading just a small bit when you locked eyes with Dean. Pulling away from the tall man and taking a step forward, you casually extended your hand and addressed him in the same friendly tone of voice. "Hi there, Dean."
He scoffed, his lips curling into a smirk as he gave you an appreciative once over. "A handshake? Don't I get a hug?"
"Well, you're still sitting down, so..."
He quickly got to his feet. "Oh, sorry, got a little distracted." Wrapping an arm around your waist and gently holding the back of your head, he brought you in. "So nice to see you again, Y/N," he whispered in your ear, an almost imperceptible growl rumbling through his body. "You're looking lovely tonight."
"Well," you chirped, quickly pulling out of his grasp and shoving him off. "Jess should be out with dinner soon, so you guys can take a seat if you like."
You hurried toward the kitchen to see if she needed any help, furiously hoping your bright red cheeks would have cooled down by the time you got there. Instructing you to pick out a nice bottle of red wine, Jess took everything with her to the living room, a devious smirk plastered on her face as she walked past you.
"Have a seat next to Dean, sweetie," Jess instructed with a slightly exaggerated hand gesture, nodding encouragingly as if you were her puppet in this ridiculous play. She had, of course, orchestrated the entire thing while you were still in the kitchen—her near psychotic smile told you as much.
This conniving bitch really didn't want to take no for an answer.
"Sure, Jessica," you replied through gritted teeth, the daggers you shot unable to pierce the thick layer of self-satisfaction that hung around her. You continued to smile as you sat beside him, but your whole demeanor must've screamed that you really, really didn't want to be here.
The evening progressed as it usually did—Sam and Jess were as lovey-dovey as ever, talking amongst themselves in hushed voices and the occasional giggle that escaped her whenever he spoke lowly in her ear. They were too much in their own little world to notice the awkward silence on your side of the table, discomfort rolling off you both in waves.
You could just feel his eyes searching you, and in the corner of your eyes you could see his mouth open and close—attempting to speak to you but thinking better of it at the last second. You could practically feel the pleasant warmth radiating off him and the smell of his cologne had you more intoxicated than the wine, you had to admit. But the last thing you were about to admit was that you actually enjoyed Dean Winchester's company. You were way too proud for that.
"I get the feeling you don't really want me here," Dean leaned in close, the low rumble of his voice sending an involuntary chill down your spine.
"Got that right," you muttered, reaching for your wine glass. You were going to need some liquid courage if he kept talking to you like this. "I don't know why you keep coming, anyway. It's not like Jess is a regular top chef."
He scoffed. "Maybe because I genuinely like being around you, Y/N."
Emitting a scoff of your own, you turned to look him in the eye. To see if he was as genuine as he said he was. "Why?" you asked, sounding a little more irritable than you would've wanted. Simply because you couldn't believe it. Or even deserved it, for that matter.
"Well," Letting out a breathy chuckle, he leaned back in. "I happen to think you're absolutely gorgeous. And your perfume smells really nice. And you're pretty great company—when you're not rolling your eyes at me, of course."
A cloud of heavy silence hung over you both as you were suddenly at a loss for words, anything snappy or simply coherent suddenly felt foreign. It was as if time stood still and you were just staring at each other, one waiting for the other to blink.
But still, your stupid pride wouldn't let him win.
"Whatever you say, Romeo," you snorted, standing up to clear the empty plates. "Dessert, anyone?"
The shrill sound of chair legs scraping across the floor accompanied by hurried footsteps followed you into the kitchen, an indignant huff coming from behind you as you set the dirty plates aside.
"You should learn to take a compliment, sweetheart," he spoke, frustration lacing his words as his voice grew closer.
You turned to find him standing closer to you than you thought. "Oh, I can take a compliment," you retorted, crossing your arms and staring daggers. "I just can't stand a liar."
"A liar," he echoed, a smirk forming at his lips before bowing his head. "You want me to be honest with you?"
"Please do."
The next thing you knew you were backed up against the counter, two strong arms trapping you in between them as his lips ever so lightly pressed themselves against the shell of your ear. The sensation chased goosebumps across your skin, your eyes fluttering shut and your breath catching in your throat as a dark chuckle escaped him.
"I've been hard for you the moment I saw you, Y/N. I can only think about pressing my lips onto yours, and ripping that pretty little dress off that pretty little body. About how good your pussy is gonna taste, and how I'm gonna have you coming on my tongue. I've been thinking about you, begging for my cock like the dirty girl I know you probably are, and how I'm gonna fuck you so good you won't even remember your own name." Taking a second to breathe, you soon felt his lips curl into another smirk. "How's that for honesty?"
"You're disgusting," you breathed, taking the collar of his shirt between your fingers. "You're lucky I'm into that."
Your lips met with so much urgency, so much animalistic need, that you knocked all the plates off the counter as he lifted you up. Falling to the floor and breaking into tiny pieces on the tiles, the sounds of it prompted Jess to speak up from the living room.
"Hey, is everything okay in there?"
"Everything's fine," you chirped, trying your best not to sound guilty as you hopped off the counter. "Dean's just being clumsy."
You could just hear her breathe an annoyed sigh. "And he now owes me a new set of dinner plates."
"Don't worry, I'll take care of it," you waved off her comment when you saw his brow furrow in confusion, taking a pint of ice cream out of the freezer and grabbing two spoons. "You and I are not done yet."
Placing the ice cream in front of them on the table, you handed Sam and Jess a spoon each. "Here's dessert, you told them, ignoring the fact you probably looked a lot less presentable than you did five minutes ago. "I'm gonna go show Dean the pool table we have in the basement. Because he told me he's a pretty decent pool player, didn't you Dean?"
He looked at you for a brief moment, reciprocating your demanding stare with a thoroughly confused one of his own. That was until it all clicked into place and his expression quickly changed. "I did," he nodded. "And Y/N here told me she'd love to see me in action, so..."
"Yeah, so," you made the same awkward, overdramatic gesture Jess did as you backed out of the room. "Enjoy."
You were through the door and down the stairs in a matter of seconds—the lust in the air thick and palpable. He didn't give you enough time to find the light switch, his strong arms finding you in the pitch black darkness and wrapping around your waist to pull you tight against him. There was just too much going on, too much for your senses to fully register—your desperate attempt to keep it together to find the switch, the growing ache between your legs caused by hands and lips roaming your skin. And even though your knees were about to give out from under you, you still found the strength to push him off.
"We're not doing this in the dark, Dean," you breathed.
He let out a growl. "So, we're actually doing this?"
"We are," you smirked, beckoning him with your finger.
He was on you like a mad dog, biting and sucking down your neck as he lifted you up against his chest. His fingers dug urgently in your flesh as he walked you over to the pool table, settling you gently down on the edge. Grabbing the back of your head and twisting your hair lightly and playfully between his fingers, he let his eyes slide over you in appreciation. You moaned out and reached down to rub his cock over his jeans, but he immediately stopped you.
"We're gonna play a little game," he whispered, tightening his grip on your hair as he pulled you closer. "Okay?"
A thrill ran through you and you nodded. "Okay."
"Good," he said. "Bend over for me."
You did as you were commanded and bended over the table, propping yourself up on your elbows on the green felt. Dean hiked up your dress and pulled your underwear down, taking his time by running his fingers lightly across your skin. Suddenly his touch was gone, and you were about to speak up. Until his hand smacked across your ass cheek.
Caught completely off guard, you felt it sting but you were strangely intrigued by the feeling. You couldn't explain why it felt so good, it just did. Honestly, you were too turned on to even question the rules of his 'game'. You wanted him to do it again.
"You like this, don't you?" he said, tracing the red marks with the tips of his fingers. "You're such a dirty girl, aren't you, Y/N?"
You moaned and he hit you again, causing a shiver to run up your legs and linger around your center. You were gasping and shaking, your knees about to buckle from the intense darkness in his voice.
"Say it," he snapped.
"I love it," you moaned, pushing your ass out further. "I'm a dirty girl and I love to be spanked."
"Good," he groaned, running his hands across your sensitive skin. "Now touch yourself for me, sweetheart."
"Why don't you—"
Another slap across your ass cheek. "I want to see you fuck yourself. I want you to pretend it's me and tell me what you're thinking about."
You reached down your body and pressed your fingers down on your clit, moving them in slow circles. Small shocks coursed through your body and you nearly fell over—the excitement, the pleasure and his watchful eye almost too much to handle. Dragging two fingers through your soaked slit, you gathered your juices before slipping them inside.
"That's right, sweetheart," he spoke softly from behind you and you squeezed your eyes shut, pretending it were his fingers.
"Fuck, Dean," you moaned, curling your fingers as you moved them at a faster pace.
A low, lustful growl filled your ears. "God, that looks so hot. Tell me what you want me to do."
"I want you to fuck me, nice and deep and rough," your fingers were back on your clit, your eyes still shut tight while you imagined it all go down. "I want your cock inside of me, filling me up."
His hand came down one last time before he kneeled down and pushed your hand away. "Time for dessert," he announced, grabbing your ass and opening you up for him with his thumbs. He found your clit instantly, but didn't touch it. He licked around it, teasing you every second with the closeness of his warm tongue. You pushed back, trying to make him touch you—but still, he wasn't going to make it easy for you. He ran his tongue around your entrance and lips, but stayed away from where you wanted him most.
After what felt like an excruciating eternity, he finally brushed up against your clit. The pleasure was surprisingly intense—making your eyes water and your knees wobble. Brushing up against it twice more, he pressed his tongue down hard, flicking it back and forth and up and down.
Your whole body tingled and pulsed and you felt like you were in a world of your own—a world that only had room for the two of you. You closed your eyes and forgot everything and everyone around you, focusing solely on his skilled tongue.
"Oh, fuck," you whimpered, desperately clawing at the felt. "Yes, Dean."
"That's it, baby, keep saying my name."
He slipped a finger inside and immediately located your sweet spot, nudging and pressing it while his tongue still worked on your clit. His movements got faster and faster and he soon brought you to the brink—before he abruptly stopped.
You slowly regained your senses and noticed you were panting heavily, your dress covered in sweat and sticking to your body. Pushing the hair out of your face, you snuck a glance behind you and saw him admiring you, his eyes dark as he licked his lips.
"Do you want me to keep going?" he asked, running his hands over your ass.
"Yes," you moaned weakly. "Yes, please keep going."
"Beg," he simply stated.
You rolled your eyes, knowing this side of him would pop up sooner or later. But you really didn't have to think about it—this was exactly what you wanted.
"Please, Dean—please keep going. I'm a dirty little girl, just like you said. And I want you to make me come, please just keep going."
His hand smacked your ass again and you could just feel your wetness slide down your thighs. Then his fingers slipped back in and all you knew was pleasure, the feeling of his skilled tongue circling your clit making your lips quiver and your knuckles go white from holding on tight to the edges of the pool table.
Before you even knew what was going on, Dean was back on his feet, wrapping an arm around your waist to urge you upright. His hand slipped down your front and started working in overdrive, making you shiver and shake as your high began to crash over you. Pleasure came over you in waves—waves and waves of white hot, unimagined ecstasy.
Dean's warm breath ghosted over your skin and you felt his stubble graze your cheek, his chin resting on your shoulder as he rubbed you through your delicious high. "Turn back around, sweetheart."
Moving turned out to be a struggle—your ass was stinging and your legs felt weak and your head light—but when you did, you hopped up on the edge of the table. You leaned back on your hands and smiled lazily at him as he dragged two fingers through your folds, his eyes connecting with yours as he slid them into his mouth and sucked on them until they were completely clean.
"You want me to fuck you, don't you?" he asked, his fingers twisting tightly in your hair again.
You nodded. "Yes."
He took out a condom before he undid his belt and his button, his jeans and boxers dropping to the floor and pooling around his ankles. After fiddling around with it for a couple of seconds, his hand was back in your hair, pulling your head back and urging you to look at him. Without a word, he guided himself in, tearing a loud gasp from your throat.
He seemed to go deeper than anyone had ever gone before. He went past your sweet spot and lingered there, painful and pleasurable at the same time. That first thrust seemed to last forever—time paused and it was just the two of you in that brief moment. Until everything sped back up and he was pounding in and out of you.
You bit your lip but you couldn't contain your pleasure—you screamed out, your efforts at silence mocked by your own weakness. Dean reached up and wrapped his hand around your throat, squeezing it lightly and silencing you. His touch was hot, sweaty and strong, his hair sticking to his forehead as tiny drops of sweat cascaded down. Your body was caked in sweat and you were breathing faster than you could comprehend—it was as if your heart was trying to escape from you.
He leaned in and whispered in your ear, his hand still on your neck. "I've been fantasizing about this for so long," Loosening his grip, he slowed down his thrusts and eased himself in and out of you slowly and deliberately. "You're beautiful, Y/N. You're the most beautiful girl I have ever seen. And I'm willing to eat Jess' awful spaghetti if that means I get to be near you."
You leaned in and found his lips, wrapping your arms tight around his neck as you kissed him long and hard. A loud moan escaped you as he angled his body and pushed his cock into your sweet spot—just touching it—and then pulled away, as if you knew exactly where it was. You clawed at his shoulders and whimpered weakly as he kept driving.
Grabbing your leg and hooking it around his waist, Dean thrust into you at a much deeper angle. He hit your sweet spot perfectly, making you bite down on his shoulders and clench the fabric of his shirt between your fingers. All you could hear were the fleshy sounds of him snapping his hips into yours and his deep, almost-animalistic grunts. Your sweet spot was a burning point of pleasure, pulsing and throbbing every time he hit it.
You squeezed your eyes shut and were suddenly hit by another wave of burning, incomprehensible ecstasy. You screamed out and your whole body shook—as much as it could in his tight hold—and you came, long and hard. It washed over you, over and over again, a relentless wave.
But before the pleasure had a chance to fully pass, he grabbed your hair without warning and pressed his other hand back on your clit. Pressing his fingers down on it like a button and rubbing it up and down, he leaned back in and groaned in your ear. "Come for me again," he demanded, rubbing faster and harder while he still pounded into you incessantly.
You stared up at him, his handsome features contorting as he was trying to postpone his own high in order to get you there first. His green eyes shone luminous and you found genuine emotion behind them, before he shut them tightly and released a guttural groan.
As you both came, you quivered and tried to grab his arm, making a futile attempt to push his hand away. He was too strong and you were secretly glad—you really didn't want him to stop. You wanted him to stroke you through your high and you wanted to be overpowered by him.
"Oh fuck, Dean," you moaned, your whole body jerking and shaking before you both completely stilled. Your chest rose and fell rapidly as you leaned back and he pulled out, your whole body covered in sweat.
Dean pulled his pants back up and fastened them, smiling sweetly as he offered you his hand. Taking it and getting off the table, your knees immediately gave out from under you, making you fall against his chest.
"Jesus Christ, that was fucking amazing," you breathed, pushing the hair out of your face before you pulled your panties back up. "How did we even get to this?"
"Well," he chuckled, tucking his shirt back in his pants. "You wanted me to be honest."
