~♡ꜝꜞ ❝ 𝓒OO's pet ❞ ────── · · Tech Worker! Sam Winchester x fem ! boss ! reader
a / n : OMFG I AM FERAL FOR THIS SAM AHSAJFDASDJGA
character/s featured. sam wessner (winchester) .ᐟ dean smith (winchester) .ᐟ rating: smut .ᐟ
summary : floor 7's Tech Worker Samuel Wessner is constantly being seen on the elevator riding up to the top notch floors, what reason could there be behind it?
🏷 ,, ( @reginaphalangelobster , @isaa3xvs , @paigelouise , @laywinchester , @whimsicalbunnys , @dandelionsn , @nutcasefuckface , @stilesobruges , @cutiepiee-1234 , @urbxxnny , @v3nd3ttal3on , @lawboy-69 , @baldwincain )
The fluorescent lights of Sandover Bridge & Iron's twenty-second floor hummed with that particular frequency that usually made Sam's teeth ache, but today he barely noticed. His eyes were fixed on the blinking red light on his desk phone: the one that meant an internal call from one of the upper floors was coming through.
His heart stuttered.
The cubicles around him buzzed with the usual afternoon activity: keyboards clacking, phones ringing, Ian cracking jokes two desks over about the new intern's disastrous attempt at making coffee in the break room. Sam heard none of it. All he could focus on was that insistent little red light.
It's probably nothing, he told himself, even as his hand trembled slightly reaching for the receiver. Could be any department. Could be someone from Accounting with a printer issue. Could be-
"Samuel," your voice purred through the line, and Sam's breath caught in his throat. "I need you in my office. Right now."
His mouth went dry. "O-okay," he managed, his voice cracking embarrassingly. "I'll be right up."
"Good boy." The line went dead.
Sam sat there for a moment, the receiver still pressed to his ear, listening to the dial tone. His khaki-clad thighs pressed together beneath his desk, trying to will away the sudden and very inconvenient tightness in his pants. Good boy. Those two words, spoken in that particular tone you used when you were in the mood, had his entire body responding like a Pavlovian dog.
"Whoa there, buddy." Ian appeared at the edge of his cubicle, coffee mug in hand, his perpetually scruffy face split in a knowing grin. "You look like you just saw a ghost. Who was that?"
Sam hastily hung up the phone, his cheeks flushing. "No one. Just—it was nothing."
"Nothing, huh?" Ian leaned in, squinting at the caller ID display on Sam's phone. His eyebrows shot up. "Wait, isn't that the twenty-second floor? That's the COO's floor, man. What does the COO want with you?"
"I don't know." Sam lied, and it came out so unconvincingly that even he winced.
Ian's grin widened impossibly. "Uh-huh. Sure you don't. You know, this is, like, the fourth time this week you've been called up to the top floors. And you always come back looking like you've been put through a spin cycle. Hair all messed up, shirt untucked..." He gave a low whistle. "What exactly are you getting yourself into, Winchester?"
Sam's flush deepened to a shade that rivaled the red mug on his desk. "I genuinely don't know." he said, which was at least partially true. He never knew what to expect when he went up to your office. Sometimes you just wanted to talk, to ask him about his day, to lean against your desk and smile at him in that way that made his knees weak. Other times—well. Other times he ended up with his face buried between your thighs and your fingers tangled in his hair, begging you to let him come.
"Ian, I really have to go," Sam said, already scrambling to his feet. "She- the COO- she's waiting."
"I bet she is." Ian clapped him on the shoulder. "Good luck, buddy. She's got you wrapped around her finger so tight you probably can't feel your own dick anymore."
"Oh, shut up." Sam hissed. "I hate you."
"No, you don't. You love me. I'm the only one who knows how to fix the printer when it jams, and you're too tall to fit under the desk to reach the power cord."
But he was already walking toward the elevators, his long legs eating up the distance. He could feel Ian's eyes on his back, could imagine the smug grin on his friend's face, but he couldn't bring himself to care. All that mattered was getting to you.
The elevator doors slid open, and Sam stepped inside, jabbing the button for the twenty-second floor. The doors were just beginning to close when a hand shot through the gap, forcing them open again.
"Hold the elevator, would ya?"
Sam's heart plummeted into his stomach.
Dean Smith strode into the elevator, all easy confidence and swaggering charm, his suit perfectly tailored, blue tie clean and spotless. He was in his late twenties, with the kind of boyish handsomeness that drove women crazy. In this world, he was just another person over him on the food chain. In another life—one that Sam only lived in his dreams—he was something else entirely.
But Sam knew those were just dreams. And that Dean had a way of looking at him that made him feel like he was being x-rayed.
"Hey there, tech boy." Dean said, leaning against the elevator wall. "Going up?"
"Um. Yes." Sam cleared his throat. "Yes, I am."
Dean's eyes flicked to the lit button on the panel—twenty-two. His eyebrows rose. "That's the COO's floor, you know."
"I know."
"Funny." Dean crossed his arms, his expression unreadable. "You seem to be going up there an awful lot these days. What's the deal?"
"My job requires-"
"Your job requires you to be in the IT department on floor 7." Dean cut him off, that smirk widening. "That's where you're supposed to be. That's where your desk is. That's where I always see you, hunched over your computer looking like you're doing something important."
Sam's jaw tightened. "I've been called up. There's an issue with the COO's computer."
"Is there now."
"Yes. There is. And I need to go fix it."
Dean studied him for a long moment, his eyes traveling from Sam's flushed face down to his hands—which were currently clenched into fists. The elevator rose slowly, floor by floor, and with each passing number Sam's anxiety ratcheted up another notch. Did Dean know? Had someone seen you two? Was there some kind of company rumor floating around?
"You know," Dean said finally, and his voice had taken on a strangely amused quality, "I've worked here for a while. Long enough to know that the COO, oh, she's got a type."
Sam's head snapped toward him. "What?"
Dean just grinned, wide and knowing. "Relax, tech boy. Ain’t gonna say nothing. Just..." He gave Sam a long, appraising look. "I kinda see why she likes you. You've got that whole 'eager puppy dog' thing going on. Real sweet. Kinda pathetic, but sweet."
The elevator chimed, announcing their arrival at the nineteenth floor. Dean pushed off from the wall, clapping Sam on the shoulder as he passed.
"Have fun up there," he said, and there was something almost fond in his voice. "And try not to look quite so desperate when you come back down. It's a dead giveaway."
The doors slid shut behind him, leaving Sam alone with his racing heart and burning cheeks.
The twenty-second floor was quiet, as it always was. Plush carpet muted the sound of Sam's footsteps as he walked down the corridor toward your office. The walls were lined with tasteful art, landscapes and abstract pieces that probably cost more than what he made in a year, and the air smelled faintly of expensive perfume and new carpet.
Your office door was closed, but Sam could see your silhouette through the frosted glass. You were moving around inside, probably clearing your desk or preparing for his arrival. His mouth went dry again.
He knocked twice.
"Come in."
Your voice was all business, smooth and professional. But Sam had been sleeping with you for three months now. He knew the subtle changes in your tone, the way your voice dropped just slightly when you were in one of those moods. And right now, your voice had that particular quality that made his knees feel weak.
He pushed the door open.
You were standing behind your desk, your blazer already hanging on the coat rack by the door, leaving you in a silk blouse that clung to your curves. Your hair was perfectly styled, your makeup flawless, and you were looking at him with that smile: that secret, knowing smile that promised everything.
"Close the door," you said, not looking up. "And lock it."
Sam obeyed, his fingers fumbling with the lock. He heard the click, and then-
"Now get over here."
He was on you in less than a second.
His hands found your hips first, fingers digging into the fabric of your pencil skirt as he pulled you against him. His mouth crashed against yours, desperate and hungry, drinking in the taste of your lip gloss and the faint hint of coffee on your breath. You made a small sound of surprise against his lips, but you were already kissing him back, your hands coming up to tangle in his hair.
God, your hands in his hair. That was always what did him in. The way you'd grip the auburn strands and pull just enough to make his scalp tingle, directing his head exactly where you wanted it. You tugged now, pulling his head back just far enough to break the kiss.
"Eager today, aren't we?" you murmured, and your voice was lower now, huskier.
"Please." Sam gasped, because that was all he could say. Please. Please touch him. Please let him touch you. Please, please, please.
You laughed softly, and the sound went straight to his cock. "Please what, sweetheart? Use your words."
But Sam couldn't use his words. He couldn't think. All he knew was that you were here, and you were touching him, and he needed more. He surged forward again, capturing your mouth in another desperate kiss, his hands sliding up your back to clutch at your shoulder blades. You let him, kissing him back with equal fervor, and then you were pushing him backward, wriggling your body between his long legs, and-
His back hit the wall with a soft thud.
You were between his thighs now, your body pressed against his, and you were kissing him like you wanted to devour him whole. Your hips moved in a slow, rolling rhythm against his, and even through the layers of fabric he could feel the heat of you. His breath hitched, a pathetic little sound escaping his throat.
"Look at you," you murmured against his lips. "So desperate for me already. You're shaking, Samuel."
He was shaking. He couldn't help it. Every time you touched him, every time you looked at him with those dark, hungry eyes, he fell apart. It was like you had some kind of power over him, some kind of hold that made him forget everything except how much he needed you.
"I need- please, I need-"
"Awh, so cute." You kissed the corner of his mouth, then his jaw, then the sensitive spot just below his ear.
Sam whined. Actually whined, a high-pitched sound that should have been embarrassing but only made you chuckle against his throat.
"Shh," you soothed, even as your hands traveled down his chest, fingers playing with the buttons of his polo shirt. "No need to whine like a kicked puppy. I always take care of you, don't I?"
"Yes," Sam breathed. "Yes, you do. You take such good care of me."
"I do." You popped open the first button of his shirt. "Because you're such a good boy for me, aren't you? Such a sweet, desperate thing."
Sam nodded frantically, his hips bucking involuntarily against yours. You rewarded him with a kiss, deep and possessive, and then you were pulling away, tugging him by the front of his shirt toward your desk.
The surface was covered in papers, folders, and an array of pens and pencils arranged in a neat holder. You swept the whole mess aside with a single, decisive motion, sending everything scattering to the floor.
"You know how much I love this." you said, and your voice was almost fond.
"I know." Sam said, and his voice cracked on the last word.
"Good boy." You pushed him down onto the desk, and he went willingly, his back hitting the cool wood surface. "Now let me take care of you."
You climbed on top of him, straddling his hips, and the weight of you was the most incredible feeling in the world. Sam's hands found your thighs, gripping the soft flesh through your skirt as you leaned down to kiss him again. Your tongue traced the seam of his lips, demanding entry, and he gave it willingly, moaning into your mouth as you deepened the kiss.
Your hips began to move, a slow, torturous grind that had him seeing stars. His hands flew to your waist, gripping tight, trying to pull you closer even when you were already pressed against him.
"Please," he gasped against your mouth. "Please, please, please—"
"Please what?" you asked, but your voice was breathless too, and Sam could feel the damp heat of you through both your clothes. "What do you want, sweetheart?"
"You," he said desperately. "Just you. Always you."
You laughed again, that soft, throaty sound that made his head spin. "You're so cute when you're needy." You kissed his neck, soft and teasing, then harder, your teeth grazing his skin. "I love it."
Sam's hands were in your hair now, mussing the perfect style, and he didn't care. He needed you closer, needed more, needed everything. You were the most incredible thing that had ever happened to him, and the fact that you were his boss, that you were so far above him in every way, only made it more intoxicating.
"Pleasenghh" he begged. "I need- please let me-"
"Let you what?" you asked, and you were grinning now, a wicked smile that promised everything. "Let you what, Samuel? Tell me."
"Need to be inside you," he gasped. "Please. Need to feel you. Need to be good for you."
"Oh, you're so good for me." You kissed him again, soft and sweet, and then you were pulling away, climbing off of him and stepping back. "But first-"
You unbuttoned your blouse with maddening slowness, letting it fall open to reveal the lacy black bra beneath. Sam's hands twitched at his sides, desperate to touch, but he knew better than to reach for you without permission. You were in charge, and he loved it. He loved the power you held over him, the way you could reduce him to this trembling, desperate mess with just a look.
"Like what you see?" you asked, and there was a note of teasing in your voice.
"I always like what I see." Sam breathed.
You smiled, and it was softer now, almost fond. Then you were reaching for his belt, undoing it with practiced ease, and Sam's breath caught in his throat.
"Lift your hips," you instructed, and he obeyed immediately, lifting just enough for you to tug his khakis and boxers down to his knees. His cock sprang free, already hard and leaking, and you made a soft sound of approval.
"Look at you," you murmured, wrapping your fingers around him. "So hard for me already. So eager."
"Always," Sam gasped. "Always for you."
You stroked him slowly, deliberately, and Sam's head fell back against the desk. He could feel your thumb rubbing over the sensitive head, could feel the slickness of his own precum, and it took everything he had not to come right then and there.
"Please," he begged. "Please, I need-"
"I know what you need." You released him, and he almost sobbed at the loss. "But I am in control, Samuel. You know that."
"Yes," he agreed immediately. "Yes, you're in control. You're always in control."
"And you're going to do exactly what I say?"
"Anything. Ah-nything y'want."
You smiled, slow and satisfied. Then you reached down, taking off your panties, but not throwing them away like you had with the rest of your clothes. Sam blinked, confused, until you brought them to his lips.
"Open." you said softly.
He opened his mouth without hesitation. You pushed the fabric inside, and the taste of you—clean and slightly sweet, with a hint of salt—flooded his senses. He moaned around the gag, his hips bucking involuntarily.
"That's better," you said, and there was something almost tender in your voice. "Now you can be as noisy as you want. No one will hear you."
Sam whined, a high-pitched sound that was muffled by the fabric in his mouth. You just smiled, climbing back onto the desk to straddle him once more.
"Ready?" you asked.
He nodded frantically.
You positioned yourself over him, and then you were sinking down onto his cock, and Sam's world went white.
The feeling of you enveloping him was almost too much, the heat, the tightness, the way you seemed to grip him like you never wanted to let go. His hands found your hips, clinging desperately, and you started to move.
Up and down, slow and deep, taking him all the way to the hilt before rising again. Sam's eyes rolled back in his head. He could hear himself making sounds, desperate little whimpers and moans that were muffled by your panties, but he couldn't stop them. You felt so good. You always felt so good.
"Look at you," you breathed, and your voice was strained now, the first crack in your perfect composure. "So beautiful like this. So desperate for me."
Sam nodded, his eyes fluttering open to meet yours. You were watching him with that hungry, possessive gaze, the one that made him feel like the most wanted person in the world.
"Good boy," you whispered. "My good boy."
The words sent a shiver of pleasure down Sam's spine. His hips bucked up instinctively, driving himself deeper inside you, and you made a sound of approval.
"That's it," you encouraged. "Fuck me, Samuel. Fuck me like you mean it."
He did. He fucked you like his life depended on it, his hips slamming up into yours with every thrust. Your hands were on his chest, nails digging into his skin through the thin fabric of his shirt.
"Close-" you gasped, and that was the only warning he got before you were coming, your body clenching around him in waves that sent him over the edge with a muffled moan.
Stars exploded behind his eyes. His hips kept moving, chasing the feeling, pumping into you through your orgasm and his. It felt like it lasted forever, wave after wave of pleasure crashing through him until he was limp and trembling on the desk, you collapsed on top of him.
For a long moment, neither of you moved. The only sound in the room was your ragged breathing, and the distant hum of the building's heating system. Sam's heart was pounding so hard he could feel it in his throat.
Finally, you stirred, lifting your head to look down at him with a soft, satisfied smile. You reached into his mouth, gently pulling the wadded panties free, and Sam took a deep, grateful breath.
"Good boy," you repeated, and you leaned down to press a kiss to his forehead. "You did so well for me."
Sam smiled, feeling a warm glow spread through his chest. "I always want to be good for you."
"I know." You kissed the tip of his nose. "That's why I keep you around."
Twenty minutes later, Sam was back in the elevator, his hair still slightly mussed and his shirt only halfway tucked in. His legs felt like jelly and he was fairly certain his face was still flushed, but at least he didn't look like a complete disaster.
The doors opened on the nineteenth floor, and Dean stepped in.
"Well, well, well," Dean said, his eyes sweeping over Sam with obvious amusement. "Look who finally made it back. You look like you've been through the wringer, tech boy."
Sam opened his mouth to reply, but nothing came out.
Dean just laughed, shaking his head. "You know, I've been working here for a long time. Seen a lot of things. But I gotta say, the COO's taste in men is... interesting."
"Dean, I don't know what you're implying, but-"
"Relax." Dean clapped him on the shoulder. "I'm not implying anything. I'm just saying, she's got a type. Big, tall, kinda pathetic, eager to please." He grinned. "You fit the bill pretty well."
Sam's face went red. "I don't- we're not-"
"Hey, I don't care what you're not doing." Dean held up his hands. "Far be it from me to judge. If I had a boss like that, I'd probably be right there with you. I'm just saying, you might want to be a little more discreet." He gestured vaguely at Sam's face. "You walk out of her office looking like that and people are gonna start talking."
Sam swallowed hard. "Right. Of course. I'll be more careful."
"See that you are." Dean's eyes glinted with something that might have been genuine amusement. "And for what it's worth? Good for you. She seems like a fun one."