“The actors aren’t the authority on the characters, you can disagree with their opinions” This is very true except for Jared Padalecki. Jared is the Number 1 authority on Sam and every word he says about him is gospel.
PAIRING: jared padalecki as “sam winchester” from “supernatural” x black!fem!reader
SUMMARY: in which you and Sam work as executive assistants for the co-managing partners of your law firm and your boss asks you to book the hotel rooms for an end-of-the-year retreat for you and the rest of your coworkers to go on. unfortunately, you realize that you and Sam will end up sharing a room together because you forgot to pair him up to share with someone else, which ultimately leads to unraveling tension. 🤍
you sat in your office with your eyes glued to your computer screen, a concentrated expression splaying across your features as you created room arrangements for your law firm.
since the year was coming to an end, your boss, Simone Whitman, and her co-managing partner, Theodore Prescott, thought it’d be nice to take the firm out to Los Angeles for its annual end-of-the-year retreat, and you were tasked with finding a hotel and booking the rooms, which meant you were also tasked with pairing your coworkers together as roommates.
after coming up with a list of hotels and consulting them with Simone, who then discussed them with Theodore, you were ultimately tasked with booking rooms at the Fairmont Century Plaza in Century City, Los Angeles, which had 19 floors and 400 total rooms. unfortunately, there were 200 workers at your firm — technically 202, if you include Simone and Theodore — so you were practically slammed having to book around 100 rooms and plan out who’d be rooming with who, along with trying to book 5 floors that were close together with no other guests staying on them so all the workers could be together — this ultimately led to you booking floors 5-10 since those floors were the emptiest ones.
Simone and Theodore were the first ones you booked rooms for you, and you gave them exclusive Fairmont Gold rooms with a good view of the city to accompany them and their spouses, both of which on the 10th floor. however, before actually booking the rooms, you double-checked with them to make sure they were satisfied with it, and once they gave you the green light, that was when you went through the tedious trouble of having to book rooms for your coworkers.
you booked rooms by gender and the position they held at the firm — for example, you put two women who were Paralegals in the same room and two men who were Paralegals in another. you went through this unnecessarily long process and continued pairing people together until you eventually reached ‘Counsel’ and paired those workers together, which made you let out a soft yet heavy sigh of relief.
you had finished the most annoying part of your task… or so you thought.
as you double-checked the list of employees Simon gave you to make sure you booked rooms for everyone, you suddenly paused as you realized that the only person you had forgotten to book a room for was none other than Sam Winchester, who was Theodore’s executive assistant. a look of horror crossed your face and you swiftly rechecked the list of employees and the chart of paired employees and room numbers you created in Microsoft Word while booking rooms to make sure you weren’t losing your mind, but they all told you the same thing — because you forgot to book a room for Sam, you’d have to share a room with him.
the main reason Simone and Theodore agreed to pairing their workers as roommates was to save a bit more money instead of booking over 200 rooms for every individual person. granted, booking over 100 rooms was still expensive, but what made it more expensive is that since the retreat was a week long, you’d be staying in those rooms for 7 days until it was time for you to leave, so Simone and Theodore thought it was best for everyone to pair up and sleep together.
the thing that frustrated you the most is that you paired everyone by their gender, meaning women slept with women and men slept with men, so how the hell could you, a woman, share a room with Sam, a man, when it goes against how you paired up everyone else?
not to mention, the tension between you and Sam was… very palpable, to say the least.
reluctantly, you booked a room for you and Sam to share and finished up the documented chart of paired employees and room numbers as you typed out an Email with thorough information about the retreat — when you’d leave, what time you’d leave, how you’d leave, what you’ll do while there, etc. — and attached the Word document to the message before sending it to the entire office, a heavy exhale falling from your lips for a second time while you took your hands away from your keyboard and mouse and leaned back against your chair.
this was about the longest and most tense end-of-the-year retreat you’d ever been on in your life.
“are you sure you’re comfortable with me sleeping next to you? because i can always take that armchair over there.” Sam reassured for what felt like the millionth time since the two of you arrived at your shared room, earning a soft laugh while you sat your suitcase on the bed and unzipped it.
truth be told, sharing a hotel room with Sam made you nervous, but sharing a bed with him felt like pure temptation. it was no secret that you and Sam had feelings for each other, but neither of you wanted to act on them not only because both of you thought it was very unprofessional for two coworkers to date, but also because you didn’t necessarily have time for any kind of romantic connection due to your hectic schedule.
you didn’t know how being Theodore’s assistant was, but Simone had you working your ass off for her every single day. even on days you were supposed to be off, you had to do some sort of errand or schedule some kind of arrangement for her, which aggravated the hell out of you, but at least she paid you extra when she needed you on your off-days.
because of your busy schedule, you barely had time for your friends, so you knew getting into a relationship would only worsen the stress you already went through at work because you and your spouse would most likely end up arguing about how you didn’t make time for them, and you truly didn’t have time for any of that nonsense.
“Sam, it’s fine. really, it is. plus, i don’t want you sacrificing your sleep for me all because i forgot to book you a room,” you chuckled softly as you pulled out a pair of pajamas and a pair of underwear, purposely sliding your underwear between your top and bottom to avoid them from being seen, “i’m really sorry for that, by the way, i should’ve double-checked and made sure i paired you with a man before i finished pairing people together.”
“no, it’s okay, i get it. it sounds like one hell of a hassle, so i don’t blame you for that.” Sam chuckled, smiling a little, as you laughed and zipped up your suitcase, making sure to grab your bag of toiletries from it before moving to sit up ur suitcase beside the small table in the corner of the room.
“oh, you wouldn’t believe the hassle all of that was,” you laughed, shaking your head, as Sam laughed with you and you smiled at the sound while collecting your things and looking over at him, “you mind if i shower first, Winchester?”
“go ahead, ladies first.”
when Sam came out of the bathroom after his shower, the last words he said to you were “last chance to let me know if you’re still comfortable with me sleeping next to you before i lay down.” before the two of you ended up going to sleep beside each other, Sam on his back while you laid on your side with your back facing him. you weren’t uncomfortable sharing a bed with Sam, but you were uncomfortable at the thought that sleeping next to him could turn into sleeping with him since the two of you were attracted to each other.
but little did you know… you were right to have that worry.
you stirred awake in the middle of the night, a soft groggy groan coming from you once your eyes fluttered open and you adjusted to your surroundings. reaching up, you gently rubbed one of your eyes while the other flickered towards the alarm clock on your nightstand, ‘2:25 A.M.’ staring back at you in LED writing. lowering your hand from your face, you shifted your hips to get comfortable but suddenly paused once you felt Sam’s hand grab onto your hip to still your movements, a soft grunt coming from him while he adjusted his position behind you.
“don’t do that.” Sam whispered, his voice husky from sleep, as your body went rigid and the grogginess in your system suddenly vanished, realization dawning on you faster than it ever has.
somehow, you and Sam managed to drift closer to each other in your sleep and were now spooning, his front pressed against your back while his arm was previously wrapped around your waist. because of how close you and him were, when you shifted your hips, your ass rubbed up against his dick, which ultimately woke him up from a clearly not-so deep sleep.
“…i’m sorry,” you whispered sheepishly, surprisingly not moving from your position, as you swallowed hard and felt Sam’s grip loosen on your hip, “i didn’t mean to. i didn’t know we were, um… this close.”
“it’s okay, i didn’t either,” Sam whispered as he let go of your hip and his hand hovered above your it with uncertainty, not knowing what to do with it since both of you were now awake and fully aware of how you were positioned, “do, uh… do you want me to move?—”
“no,” you admitted too quickly for your liking, catching yourself and Sam off guard, as you let out a soft shaky exhale, “no, i-i don’t want you to move.”
“are you sure?” Sam asked softly, raising his head from his pillow, as you reluctantly turned your head and looked back at him, meeting his gaze through the dim lighting of the room supplied by the moonlight peeking through the curtains.
you parted your lips to speak but nothing came out as you stared into Sam’s eyes, the walls you had built around your heart slowly crumbling down while you got lost in colored irises. you didn’t know if it was because you had just woken up or if your body was tired of fighting how you felt, but you moved closer to Sam and his breathing hitched at the feeling of your body snugly against his like a puzzle piece.
“i’m sure,” you whispered, shifting your position, as you turned around to face him and never once broke eye contact, his hovering hand dropping to your waist while he watched you, “never been more sure of anything else in my life until now.”
“Y/N,” Sam whispered, his thumb drawing small circles against your waist, as you reached up and rested a hand on his upper arm, noticing his bicep slightly flex underneath your palm, “a-are you really sure about this?”
“kiss me before i change my mind,” you suddenly whispered, your voice coming out a mixture of a demand and a plea, as your other hand reached up and cradled his jaw, “please, Sam. i need this. we need this.”
you didn’t know what had come over you, but all you knew at that moment was that you wanted Sam. you didn’t care about the “no dating coworkers” rule both of you had at that moment and you certainly weren’t thinking about the consequences of sleeping with your boss’s co-managing partner’s assistant. your body craved Sam and you couldn’t fight it anymore.
in fact, you were getting pretty damn tired of fighting it.
Sam’s lips were on yours in the blink of an eye, and the tension in your body almost instantly melted away as your hand on his upper arm moved upward to the nape of his neck, cradling it in your palm while his large hands splayed across your back and pulled you closer. the kiss was slow and filled with all of the passion both of you had been holding back throughout the months of working together and having to hide your attraction to one another, and it seemed as if things were getting more and more intense as time passed by.
before you knew it, Sam had switched positions and was now on top of you, his hands cupping your face as he desperately deepened the kiss. your legs spread a little wider to make room for his large frame and he settled between them with ease, the bulge in his sweatpants now pressed against your core through your pajama shorts and eliciting a soft moan from you.
“Sam…”
“what is it?”
Sam quickly pulled away from the kiss and cautiously looked down at you, his eyes thoroughly searching your face for any sign of discomfort but finding none.
“i need you,” you pleaded softly, your hands sliding underneath his shirt, as Sam’s breathing hitched and he glanced down at your hands before meeting your gaze again, “you don’t understand, i’ve fought this for so long, Sam. i haven’t… haven’t been touched in forever, i need this.”
you hated how desperate you sounded, but you couldn’t help it. you were tired of putting your needs to the side for the sake of your job and it was only a matter of time before you cracked underneath the overwhelming pressure.
but right now? right now, you weren’t just cracked — you were fully shattered, and you didn’t care about anything in that moment but Sam fucking your stress away.
not wanting to keep you waiting any longer, Sam undressed you, his hands moving eagerly yet slow enough to come to a stop if you decided you wanted to back out. you watched his eyes sparkle as he drank you in, his pupils eyeing you down like he’d never saw you before in his life.
technically, he hasn’t seen you like this before, so he couldn’t help but to be fascinated.
“God, you’re so beautiful,” Sam whispered in awe, pulling off his shirt and tossing it aside, as his hands dropped to your waist and he gently rubbed your sides, “so, so beautiful.”
you smiled a little and leaned up to him as you kissed him deeply, one of his big hands moving to cradle the back of your head while the other remained against your waist. your hands moved from his torso to his hips and your fingers hooked into the waistband of his sweatpants and boxers as you slowly pulled them down, exposing his fully hard dick while he kicked off his clothing.
Sam’s hands shifted to your thighs and he pulled you close as he tilted his head a little and deepened the kiss again, one of his hands leaving your thighs to grab ahold of his dick and place the tip at your entrance. sliding in slow, a moan of relief fell from both of you and you broke the kiss in unison, his forehead resting against yours while he continue slowly sinking forward and pushing his dick inside you.
“oh, baby, you’re so tight… so wet f’me,” Sam groaned blissfully, pulling your thighs up to his waist, as he lowered his body onto yours and made your chests press together, “open up for me, babydoll, c’mon… there you go.”
you whimpered in response, your hands clutching his shoulders while your jaw slightly dropped and your breathing faltered for a moment. once Sam had bottomed out, he pulled his head back a little and looked down at you, his eyes searching your face again while his hands moved upward from your thighs to your waist.
“does that feel okay?” Sam asked softly as you swallowed hard and slowly nodded your head, a soft breath falling from your lips.
“y-yeah… yeah, it feels good.” you reassured, your voice soft and breathy, as Sam slightly nodded and leaned down again, capturing your lips into a passionate lip-lock while he began moving his hips.
he started off slow to get you used to his size, his hips gently rolling against yours careful enough not to hurt you as you moaned softly into the kiss with each thrust. once he felt you open up and adjust to his size, he sped up a little more, his thrusts now at a steady and moderate pace as he bucked into you with passionate and precision.
eventually, the kiss broke and he planted soft kisses against your jaw before dipping his head down into the crook of your neck, groaning deeply against your melanated skin while pressing kisses against your pulse point. you cradled his head with one hand and held onto his back with the other, his muscles tensing and flexing underneath your fingertips, as your eyebrows furrowed and your eyes rolled back, your head sinking further back against your pillow and exposing more of your neck to Sam.
“S-Sam… oh, Sam, that feels s-soooo good.” you whimpered, your voice laced with need, as your jaw went slack and your mouth hung open, your legs wrapping around his waist to pull him closer.
“you deserve it, beautiful… deserve feel all good and relaxed,” Sam murmured against your neck, moaning at feeling you clench around him, as his arms wrapped around your body and he held you closer, your breasts now smushed against his firm chest while he sped up his strokes again, “want to make you feel so good that you won’t be so tense anymore… want you to drop your guard and let me in, so i can take care of you.”
a desperate moan flew from your lips at his words and both of your hands now clung to his back as you pulled him impossibly closer, practically wanting him inside your skin while he kissed up from your neck to earlobe.
“that’s it, honey, attagirl. look at you relaxing for me. you listen so well, beautiful,” Sam cooed against your earlobe, slightly tightening his grip on you, as a guttural groan fell from his lips at feeling your nails sink into his back and his jaw clenched a bit, a small furrow forming between his eyebrows, “it’s alright, babygirl, i got you. i’m right here. hold onto me as tight as you need.”
“Saaaam, baby, i’m g-gonna cuuum,” you whined, one of your hands leaving his back to cradle his head, as your fingers tangled in his hair follicles and you felt him gently kiss your earlobe, a shiver running down your spine at the feeling while you whimpered desperately, “p-please don’t stop, baby, please. n-need to cum, need you— o-oh, shiiiit!”
“cum for me, sweet girl. let it all go just for me. let me see that stress drain from your beautiful face, babydoll.”
