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#also I imagine my mutuals are wondering who the fuck Cole is at this point
thecleverdame · 4 years
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Control and Release - 32
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Series Masterlist
TEDTalk!Sam x Reader
Summary: After the rest of the staff is caught in a snowstorm, you find yourself acting as a personal assistant to the notorious Sam Winchester. As the arrangement becomes more defined, you and Sam begin a sexual adventure with dangerous consequences.  
Warnings: Dom/Sub, humiliation, embarrassment, sexual objectification, mutual masturbation, spanking, cum play, fingering, anal play, orgasm control, nipple clamps, dub-con, breath play.
Beta: @ilikaicalie
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-
Without fail, Sam used to wake up early and go to the gym. He’d be up before the crack of dawn, sweating out all his frustrations and pushing himself harder than he probably should.  That was before. Things have changed. It’s no longer as easy for him to jump out of bed and start the day. Life has shifted. It didn’t happen all at once, it was little by little, his obsession with work waning as you become a focal point in his life.
It’s before five. The streets are quiet, most of the world still asleep as Sam lies on his side watching you. He’s been awake for an hour, silently watching your back rise and fall. It’s dark save a tiny bit of ambient light filtering through the curtains, but it’s enough.
This isn’t a new thing. Lately, he wakes up early and uses these moments to think, to wrap his head around the constant chaos that’s his life. And his favorite early morning pastime is watching you sleep.
This morning you’re belly down on the bed, a hand shoved underneath your pillow. The side of your breast is soft and round and warm. He thinks about how warm and soft your skin is. He gets lost in the middle of meetings wishing he could touch you, feel you pressed against him.
The blanket is pulled just over your ass, leaving your naked back exposed. There’s a subtle rise and fall as you breathe deep and even, lost somewhere in dreamland. You’re perfect and you don’t have a clue.
He stares at the curve of your hip, that slope of your waist that he likes to grab on to. You’ve told him you’re self-conscious of that part of your body but he can’t imagine why. Everything you fuss over he finds flawless. You were beautiful when he first met you, it’s part of why he pursued you. But the more he gets to know you,the more breathtaking you become. Every day he notices some new little area he wants to touch and kiss and watch while he fucks you.
Time in London is coming to an end. It’s been eight weeks of nonstop work but he’s confident in the expansion of his business. Toni will run things here, and she’s good at her job. He’ll be able to go home without worries about the day to day.
He should feel satisfied, but he finds himself unsettled.
In these quiet moments, he thinks about himself. Who he is, the man he’s become. He’s honest. He knows returning home will mean a shift. No more sharing a hotel room, back to the grind of the work week. He’s enjoyed this time with you, become accustomed to your constant presence in his bed and in his life. He doesn’t want to go back to how it was. You with the shitty apartment that you insist on staying in. Weeknights alone.
He should just tell you what he’s feeling but he doesn’t even like to admit it to himself.
You shift, cheek rubbing over the pillow, mouth falling open as you settle back in. Jesus, he’s done for and he knows it. This is as good as life will ever get. He’s fully aware that he doesn’t deserve you, doesn’t deserve to be this happy. And he doesn’t trust it. In his experience, the next misfortune is always waiting right around the corner. Adversity is always hiding in the shadows, one moment away from total catastrophe. He’s balanced on a house of cards hoping a stiff breeze doesn’t blow him over.
“Sam,” you whisper, eyes blinking open and closing just as quickly. You’re still asleep. This is Sam’s favorite.
“Hmmm?” he hums, stroking a hand up your back, grazing over a shoulder blade.
“I like you so much,” you mumble, stretching out long. You’re dreaming and he wonders what goes on your head. Your inner thoughts are the thing he wants most but will never have access to.
He grins, watching your face fall lax again as you slip back into the deep.
“I like you so much too.”
-
He fell back asleep without realizing it and when he wakes up for the second time he’s not sure where he is. There’s an overwhelming pleasurable sensation and when his eyes pop open he realizes why.
The covers are pulled back and you’re on your knees between his thighs with his cock in your mouth.
“Fuck,” he rasps, hands going to the crown of your head.  Your mouth is unbelievable, hot and wet, always perfect around his cock. And the way you suck him like you’re getting off on it is enough to make his balls go tight.
“Good morning.” You smile as your mouth pops off his dick. Wet lips pulled back over pearly teeth as you grin like the Cheshire cat.
“Shit,” he chuckles, forcing himself awake as he looks down at you. You caress him, palm curled around him and stroking over the head of his cock and back down to the root. Slow and steady as you dip back down and take the tip into your mouth.
When he’s in charge you’re gagging on him, mouth drooling, eyes watering with him shoved into the back of your throat. But there’s something just as appealing about this, you happily sucking his cock, tonguing around the crown before taking him into the back of your mouth.
Your other hand cups his balls and he thinks he might blow his load right here and now. You’ve gotten good at reading his body. You’ve been studying him the same as he’s been memorizing you.
“Get up here,” he huffs, tugging at your hair. You respond immediately, almost always obedient to his orders.
Wiping your mouth with the back of your hand, you knee your way up, straddling his waist. You lean down to kiss him, a wet, happy kiss that makes his belly flip. He simultaneously loves and hates the way it feels to be this affected by anyone.
“I thought I’d wake you up.” Grinning against his mouth your pussy rubs along the underside of his cock where it’s curled up against his stomach. You rub yourself on him up and down, letting the crown rub over your clit until he’s coated in your slick. “God, you’re so hard.”
“I woke up with my dick in your mouth.” He gives your ass a squeeze, both hands cupping your backside as you slide up and down his length. Jesus, he could watch this all day. The way you take his cock between your folds, teasing the head only to slide back for another pass.
He’s close already, he normally holds out longer than this but you’ve caught him in a vulnerable state.
“Shit, I’m gonna cum.” His teeth click together, head pressing back into the pillow. He opens his eyes just in time to watch the first spurt of cum shoot over his belly. You make a wonderful little sound, grabbing his cock and quickly sinking down on him as he finishes his orgasm inside your pussy.
“I like it better inside me,” you quip, raising yourself up and down on his cock, fucking him through it as he jerks and bucks from the release.
You kill him when you say things like that. He’s the one with the filthy mouth but sometimes you whisper things that make his cheeks red.
“You want me to fuck you?” he offers, sitting up, holding your hips in place. You smile, both hands threading through the hair at the back of his head.
“You’re still hard?”
“That was some blowjob.” You giggle as he flips you onto your back, mouth falling open, thighs squeezing around his hips as he slides back inside in a slow thrust.
“Better hurry, you’re going to be late.”
-
7:30am
He has a budget review meeting that’s dull as dirt despite Mick’s colorful personality. It’s his money and reputation on the line. There was a time when that alone was enough to keep him hanging on every word but not anymore.
8:30am
Pepper delays his skype call with a financier in Tokyo to deal with a minor crisis back home in Boston. He’s been away too long and apparently, people have forgotten what the expectations are. There’s been a mix up with documents for a legal case in New York. A courier handed off the wrong folder. They’re looking at a delay and possible reprimand for compromising a client’s personal data. There’s also a leak in the men’s bathroom on the eighth floor that requires a total overhaul. That means a construction crew and several dozen employees temporarily relocated.
10:47am
Sam’s forty-seven minutes late for the weekly wrap up led by Toni and Mick. True to her style, she didn’t wait for him. She’s in the middle of dressing down a guy in middle management when he enters and all eyes shift to him. He glances at Toni and then around the room at the sea of semi-familiar faces before he lands on you.
There’s not enough room, so chairs have been added against the sidewalls. You’re sitting behind Cole, notepad open. God, he’s happy you're here. Not that he’ll be able to talk to you, but just being in the same room is something. You flash him a smile that’s a far cry from every other somber face in the room. There are sixty W & S employees who are scared shitless of him and then your wonderful face lights up when you see him.
He returns a hint of a smile but it’s enough acknowledgment for you go back to your notes. Millie who’s sitting beside you looks away the second he makes eye contact with her.
12:30pm
Pepper has sushi delivered and you arrive at his office right on time. He’s got a video conference with the board. You silently take a seat on the other side of his desk, eating and watching him get into over market fluctuations.
Twenty minutes later he’s off to his next appointment. He gives your hand a squeeze as you turn to leave.
“Sorry we didn't have a chance to talk.”
“It’s okay,” you smile giving him a wink. “I know how busy you are.”
Standing on your tiptoes, you kiss his cheek. It’s soft and quick and far too sweet for anything he deserves. You could make a big deal out of this if you wanted to. You could demand more of his time and God help him, he’d find a way to make it work because he won’t lose you. But you never make him choose. Occasionally you swoop in with a gentle reminder to attend to your relationship, but other than that you respect his dedication to the business. He’s forever grateful for that.
Pepper comes in with his jacket, ready to whisk him away to a waiting car.
“I love you,” you whisper at the shell of his ear, so quiet he scarcely hears it.
He’ll never get used to anyone saying those words to him, least of all you.
He sits through his meeting getting lost in his own thoughts. He wonders if his mother used to whisper those three little words to him when she laid him in his crib. If he tries hard he thinks maybe his dad said it once or twice.
Sam had successfully categorized himself as unloveable long ago. He’s an asshole. His reputation hinges on his ability to be level headed and utterly ruthless. Love was something for men who weren’t permanently damaged.
And yet here he is.
When he gets back to the office, his schedule is jam-packed. He never used to mind it, running from one meeting to the next. He got a high from it, an adrenaline rush from the breakneck pace. Work filled every waking moment and that was how he preferred it. He didn’t have to think about anything else, every waking moment was filled with strategies and budgets and concepts ripe for the picking. He was all in.
Today he finds himself between meetings, locked in a private bathroom on the second floor just to have five minutes of peace. He’s already late for a follow up with Mick and there’s a laundry list of information he should be reviewing. But instead, he’s sitting on the closed lid of the toilet, staring at the wall.  
Maybe he’s getting old. That must be it. Time waits for no man and age is finally catching up to him. He needs to talk to his nutritionist and get back to a normal routine. Watching you sleep is an indulgence that he’ll have to let go of. He needs sleep and the gym. He needs self-control.
-
He doesn’t get back to the hotel room until just after eight. He wants to stay in, he’d prefer nothing more than to order room service and lay in bed but that’s not his life.
“Hey!” you call out from the bathroom. “Welcome home.”
“Thanks,” he glances around the room at several dresses hanging from various perches. “Are you going out?”
“Yeah, I was gonna tell you.” You wander into the main room in a bra and panties. Sam swallows hard. “I can’t decide what to wear. What do you think?”
“What’s the occasion?” he asks.
“Mick invited us all to this bar for drinks. It’s a going-away thing. You don’t mind, do you?”
“No, of course not.” He needs to tell you. “In fact, I have plans as well. Toni and I are going to dinner. One final review before I leave.”
“Oh,” you return quietly.
You’re facing the bed and he watches your whole back go tense.
“I can’t avoid these kind of situations simply because I have a past with her.”
“I never ask you to.” You turn toward him, eyes meeting. You’re pissed. Or maybe it’s just jealousy.
“I know and I appreciate that.”
“She thinks she’s better than me. She looks down on me as if I’m some little girl. A comical annoyance that she’d prefer to squash if she could. She makes me feel small.”
“I don’t want anyone to make you feel that way.” He’s not sure what to say. Does he reassure you? He’s not sure if you’re looking for a response or simply sharing your feelings. “Will Cole be there?”
“I’m sure he will. Along with twenty other people.”
“Then don’t wear the black dress, it’s too much for a work function. The red one is better.”
He loves the way you look in that little black dress. It’s not revealing but it hugs every curve and there’s something about the length of it, the amount of thigh it shows. He can’t stomach the thought of Cole sizing you up in his favorite dress.
“I’ll probably be out late,” you explain, pulling the red dress on and turning around for him to zip you up. “See you later.”
-
Sam’s half done with his meal listening to Toni talk at length about her last vacation in the south of France. He might be there in body, but his mind is elsewhere.
He’s been thinking about Jess lately. She used to only pop up on quiet, lonely nights. Blurry images of her face flashing before she slipped away. But this last year she’s been in the forefront of his mind.
For years he could hardly remember her face. The details faded with time and she was like a distant memory. A story from somewhere else’s past. But over the last few months she’s flooded back to him.
He can remember the way she smelled. Sweet and fruity, a body wash she used to buy that gave her skin this faint scent of strawberries. He can taste the chocolate chip cookies, feel them in his hand, still warm from the oven.
Their apartment was a small one-bedroom with creaky wood floors and low water pressure, but nothing ever felt more like home. Her stuff was everywhere, she bought her entire life with her, a household of belongings. He brought a duffel bag of clothes and a single family photo.
She gave Sam little pep talks. Anytime he expressed even a hint of self-doubt she’d crawl into his lap and tell him a hundred reasons why he was wonderful and capable and meant for greatness.
The memory shifts and he can feel her skin. He used to stay up late studying, crawling into bed well after midnight. She’d peel her pajamas off, kissing him as he did the same. That soft strawberry skin was like silk under his hands, every inch of her pressed against every inch of him. She’d whisper in his ear when they fucked. Sometimes sweet, sometimes filthy. But it was always about love; the way she loved his touch, his cock, his heart.
And then, just as life was better than he ever could have hoped for, Jess was dead.
All that warmth and love, the home, the life, it was gone like it never existed.
“Are you even listening to me?” Toni sits back in her chair, crossing her arms.
“No,” Sam admits, setting the cloth napkin on the table next to his plate. “Today was brutal. Just going over it in my head. Pulling a game plan together.”
“Well, I’m ready for a nightcap.” She raises her arm to get the attention of the server. “Why don’t we go back to your place and review the projections one last time. Get a headstart on tomorrow.”
“Sure.” He nods. “Sounds good.
-
Sam and Toni head back to his room, and he pours himself a glass of water, opening his laptop and waiting for her to finish in the bathroom. She’s been in there for ten minutes and he’s starting to wonder if something is wrong when she finally emerges.
She’s in her underwear, white lace panties, and nothing else. Her breasts are small and perky, hard nipples already at attention. Her body doesn’t look much different than when she was younger.
Shit.
“Toni,” he sighs, pinching the bridge of his nose. “This is not…”
His words leave as she slinks toward him, practically crawling onto the couch.
He momentarily wonders if he’s become detached. Reading people has always been his forte but this but takes him so off guard that he’s stunned, a deer in the headlights as the moment unfolds.
There are a thousand thoughts at once. She’s a beautiful woman, a beautiful naked woman and yet he finds himself indifferent. He needs to make this as painless as possible, needs to find a way to turn her down without making things so awkward that they can’t work together. Sam needs Toni to run the London arm of his company, he can’t alienate her. You’d be so mad if you knew this happened. Does he tell you? He’ll worry about that later. He’s not done anything wrong. You’ll understand, you always do.
“Stop,” he hisses, pushing against the back of the couch.
“Come on, Sam.” She flashes a confident grin, then yanks his shirt from where it’s tucked into his pants. “For old time’s sake.”
“I said stop,” he says again, watching in wonderment as she doubles down. One hand slides into his hair, the other at his belt, getting him half unbuckled before he gets his wits about him. “What the fuck are you doing?”
“What does it look like I’m doing?” she purrs. “Come on, you have to want something more exciting than getting your dick sucked by a glorified secretary. Judging from all the pent up tension I’d say you’re in need of a little more satisfaction.”
She’s making it exponentially worse.
He draws in a breath and hesitates. Is this happening? Of all the things he’s got going on this is the last thing he needs. She takes his silence as encouragement and leans forward, pressing her lips against his mouth.
“That’s enough,” he grabs her wrists, pushing her backward. “I’m not sure what about our interaction has led you to believe this is something I want, but I don’t.”
“You have to be kidding me.” Sitting back on her heels, she examines him, eyes narrowing.
Sam knows her. She wants him because she can’t have him. Because of his status and the power he wields. More than anything he’s willing to bet the appeal comes from the fact that she’s competitive. She doesn’t like that you have something she wants.
Toni likes to be at the top of the food chain.
“Get dressed.” Sam scooches back, clearing his throat. “We’ll pretend this never happened.”
“You’re turning me down?” She holds her head held high. “Seriously?”
“This isn’t going to happen. Let’s just-”
There’s the familiar electronic beep of the keycard being slid in the lock and the door opens.
You stop dead in your tracks, a happy-go-lucky smile melting away from your face as you come upon the scene of the crime. Looking back and forth from Sam to Toni your mouth falls open, eyes going wide.
Fuck. Fuck.
Sam’s frozen, looking in horror at you standing in the doorway. You’re dumbfounded, the reality of what’s happening taking time to sink in.
“Good evening, Y/N.” Toni sits up straight, proud little smile with her tits on full display. “We didn’t think you’d be home so soon.”
Your mouth snaps shut, eyes darting from her to Sam and he wants to punch the wall. Wordlessly you turn and walk out of the room.
“Goddamn it!” Sam shouts. He grabs Toni’s wrists, giving her a yank. “Get dressed and get the fuck out of my room.”
By the time he makes it to the hallway, you’re halfway to the elevator.
“Y/N!”
“What?!” When you turn back you’re wild-eyed, fighting back tears. Your mouth contorts in repulsion. “Jesus Christ Sam! I can’t stand to look at you right now.”
“Don’t overreact.” Fuckfuckfuck. He knows it’s the wrong thing to say, even before you recoil. He can’t think fast enough, the words are just tumbling out of his mouth.
He can’t remember the last time he panicked like this.  
“Don’t overreact?!” you sputter, taking several steps away from him. “Fuck you! I trusted you. I must be so stupid. It never even crossed my mind that you would do something like this.”
“Nothing happened,” he counters, holding up both hands with palms out.
“Don’t lie to me. Something sure as fuck happened.” You look him over from head to toe, so disgusted that your mouth sours and you have to look away yet again. “For a guy who’s all about the details you’re not covering your tracks very well. You’ve got her lipstick on your mouth and your fly is still down.”
“What?” Sam feels at his crotch and sure enough, he’s unzipped. He’s not sure when that happened. “Look, she tried and I-”
“And you what? Let her take her clothes off? Did you fuck her?”
“No, of course not.” This is bad. He can see the escalation, the hundred ways this situation can get even worse.
“I don’t get it.” Your voice breaks as tears slip down both cheeks. His heart falls into his stomach. He’s hurt you a million different ways, both intentional and unintentional, but this might be the worst. “I thought we were in a good place. I try everything you want. I gave you a blowjob this morning. What could you possibly want from her that I’m not giving you?”
“Nothing,” he reaches out, moving toward you and you step back in tandem. “Nothing happened. I know this looks bad, I get that. But nothing happened. You came back at the worst possible time, but nothing was going to happen. That’s the truth.”
“Oh, this is my fault?” you yell. “I need to get out of here. I have to think.”
You’re tipsy, he can see it now. The wobble in your step, the way you tilt your head.
“Don’t leave.” He grabs your arm, forcing you to look at him. “If you leave it automatically makes things worse than they are. You can stay here and be pissed at me. We can talk. I’ll sleep on the couch. Just don’t leave, please don’t leave.”
Your face softens, teeth sinking into your lower lip as you consider his plea.
He knows how desperate he sounds and it makes him sick. Despite the love he has for you it’s painful for him to beg anyone for anything.
Crossing your arms over your chest you look toward the door. “She’s still in there.”
“She’s leaving.” He gets close enough to put his hands on your shoulders and nearly breathes a sigh of relief when you let him. “Just let me get her out of there. Don’t go anywhere.”
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