#Smooth operator | Explore Tumblr posts and blogs

smol-and-grumpy · 3 years ago

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Smooth Operator

Pairing: Boss!Dean Winchester x Reader

Summary: Dean Winchester has a crush and his friends think the only way to get over a crush he’s not ready to act upon is, to get under someone else. Or at least getting off as many times as he can in order to lift up his mood. That’s the story of how he came to be sitting on his couch, with a gift card from a phone sex company in his hand, and enough credit to last him a couple of orgasms.

Warnings: Flustered Dean, boss/employee relationship, pining, phone sex, dirty talk, use of toys, masturbation, office sex, spanking, praise kink

WC: 9,389

This fic is beta’d by @deanwanddamons and the cover art is done by @winchest09. Love you ladies! <3

A/N: Another one shot that turned out to be longer than really necessary. I hope you enjoy.

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SPN Masterlist

Dean has a crush.

That’s not even a bad thing. Having a crush is perfectly normal for people. It’s not really the norm for Dean, though. And that’s what is freaking him the fuck out.

He hasn’t had a real crush since Robin in middle school, and come to think of it, it’s really fucking pathetic that it has been so long already. But between school and work, he made Sammy his priority, and therefore didn’t have time for relationships, because he couldn’t, and wouldn’t, commit himself to anyone. Making money, and staying in school, in order to one day make even more money so Sammy can go and study, was his priority and not a clingy girlfriend who wouldn’t understand why Dean couldn’t put her first.

And now, even though he’s out of school and has a steady job that earns well, he just doesn’t feel the need to complicate things with relationships. Work, going for drinks, sleep, repeat. It suited him quite well… until now.

Not having relationships doesn’t mean, though, that he didn’t get any action. In fact, he has gotten laid on the regular, so he can’t really complain about that, but this feeling? This crush thing? It’s definitely bizarre.

It doesn’t help his conscience in justifying the crush as something harmless as he actually shouldn’t have a crush on the person he’s crushing on in the first place.

That person being Y/N. His newest hire.

He didn’t even hire her because of her looks or anything. In fact, she was a little bit of a pain in his ass and a thorn in his side in the first couple of weeks, but somehow she wormed her way to Dean’s heart and now he’s stuck with a stupid crush that just won’t go away, no matter how hard he tries. And it’s definitely not for the lack of trying. He had some one night stands in the beginning but he realizes that he always tends to pick up girls who looked like her to hook up with, and that led him to imagine the girl being her and after the first time her name slipped from his lips instead of the girl’s (whose name he didn’t remember in the first place), Dean decided to just give up on sleeping around. At least he intended to for a while.

That while has now stretched into several months, and he’s sure something inside of him is dead because Dean Winchester has never gone this long without sex since he discovered how much more fun it is compared to jerking off with his own two hands.

She only works part-time as she’s still finishing her master’s degree and apparently has another night job he knows nothing about. He’s sure that when she has her degree secured in her pocket, she’ll probably be gone and get a job elsewhere that pays more than what she is earning now. Not that Dean’s not going to be happy for her, but yeah, her departure will probably break him in some way or the other.

Cas and Benny, his workmates and now friends, and even Ash the IT guy knows about his crush but they don’t know exactly who it is. They just know that she works in the company. And it’s not like he wants to keep it a secret, it’s just that he really can’t tell them. She’s his subordinate, for fuck’s sake. Dean is her supervisor. You don’t have to be a genius to know that it could blow up in his face because harassment lawsuits at workplaces are very fucking real. Plus, he doesn’t want to be that dude who is accused of taking advantage of a subordinate because his position holds more power.

So, he does what he does best. Pushes his feelings down his throat and buries them deep in his guts.

Dean’s fine. Excellent.

***

They are sitting at a booth in a bar celebrating Dean’s birthday. Garth, their newest addition to the group, walks towards the table with two pitchers of beer in hand, although Dean’s mood probably calls for something stronger. But he’s not paying so he takes what he gets.

“Oh, here, buddy,” Ash throws a black envelope across the table. It hits Dean square in the face and bounces off his nose.

“Jesus, fuck, Ash! You could have poked an eye out! Stop fucking throwing things!” Dean grumbles, a little more than annoyed because it’s not the first time something like this happened. Last time it was a stapler at work. He lifts up the envelope from where it landed on the table after it bounced off his face.

“Shut up, grandpa, and say thank you.” Ash retorts.

Dean ignores Ash’s comments and eyes the envelope. It’s small, shaped like a… credit card? He frowns. “What is this?”

“Just open it.” Cas urges while he pours them all pints of beer.

He sends his blue-eyed friend a glare, lifting his eyebrow as he does, “Oh, so you’re in on this too?”

“We’re all in on it,” Benny chimes in, “And we thought you could use it to relax. We were hoping you’d be less grumpy at work and maybe you’d move on from your goddamn crush.”

“I don’t have a crush,” Dean protests.

“Uh-huh, whatever helps you sleep at night, Dean.” Garth slaps a hand on his shoulder, almost making him spill the pint of beer Dean was about to lift to his lips.

Dean lets out a sigh and rubs over his face with his free hand. He hates them all.

He’s back at home, sitting on his couch, elbows resting on thighs. He supports his chin with his fists as he eyes the black envelope like it personally offends him. Maybe it did. Maybe it will.

Dean had opened it at the bar and let the guys explain why they gave him this as a gift. They encouraged him to use it as often as he liked.

“It has about fifteen hours worth of call time on it.” Garth grinned.

“I expect you not to be as grumpy in the next two weeks. Maybe six, if you stretch it out.” Benny chipped in with a knowing smile.

And now it just sits there and he doesn’t fucking know what to do.

He grabs it off the coffee table, opens it again to look at it. It’s black, in a credit card format, shiny, and a little sparkly. Cursive lettering in golden glitter is imprinted on the front.

Sweet Temptations

Dean turns the card around, and there’s a number on it. Right below, is a part where he has to scratch off, he thinks, to get to the PIN for the credit amount his friends paid for.

Yep, that’s right. They paid for him to have sex on the phone. Apparently, because he can’t really seem to be able to find a hook up to do it in real life. And that’s when Dean really thinks how sad and pathetic his life has become.

He wants to throw it away, toss it out the window, but he just knows that it would be a dick move because again, they have paid for it, he doesn’t want to seem ungrateful. Besides, he’ll get asked on a daily basis and there are only so many times he can lie with a straight face before breaking down and confessing.

“Better just get it over with,” he mutters and fishes in his pants for a coin to scratch off the back of the card.

The phone in his hand feels slippery and his heart starts to pick up speed. It’s ridiculous how nervous he is.

Punching in the number, Dean leans back on the couch and waits until it rings. He closes his eyes, and when by the third ring nobody has picked up yet, he kind of hopes that nobody ever will and this is just some prank.

“Sweet Temptations, hello gorgeous,” a female voice greets him, all chipper, and his eyes fly open. The voice sounds older, maybe about his mother’s age, no offense, but that’s not what he was expecting. Not that he knew what to expect in the first place.

“Eh… yeah, uh, hi…” he stammers, a little taken by surprise. “Hi, beautiful.”

Smooth, Dean. Very smooth.

“Hun, how can I help you?” The voice inquires but not without chuckling softly at Dean’s term of endearment.

“Um,” he sighs and closes his eyes, “Honestly, I don’t really know. How does this work?”

The woman on the other line chuckles, “First time, huh?”

“Is it obvious?”

“Oh, hun, it’s alright. Everyone’s nervous the first time. You just tell me what you like and I will put you through to the available girls for tonight, honey.”

“Oh,” he chuckles too, maybe because of the relief he feels that the woman won’t be the one who’s going to be talking to him. Again, no offense, but he doesn’t think he could even get it up hearing that voice. “So, you’re not the one who will be...uh.. talking to me?” He asks nonetheless, just to be super sure.

“Darling, no,” the woman laughs, “That’s what I have my girls for. I’m just instructing you. Once you tell me what girl you’d like, I will put you through, and before you get connected, you will hear a beep, okay? You just have to punch in the PIN that’s on the back of your card and then you’re ready to go.”

“Right, okay, yeah. Got it,” he nods, even if the woman isn’t able to see him.

“Alright, sugar, what do you look for? Someone dominant? Submissive? What kinks you have going?”

“Uh,” he stares straight at the turned off TV, seeing his own reflection in the dim light of his living room, and he thinks. Mainly that there’s no way in hell he’s going to talk about his kink to someone he doesn’t know. “Can we just keep it, I don’t know, normal? Or at least as normal as we can get? I mean, I can still change if I don’t like the girl, right?”

“Of course, hun.”

“Yeah, so, okay. Just someone who’s maybe good at talking me into things. Mainly into doing this since it’s my first time. I mean, not that I’m inexperienced. Just not, you know, I’m more of a face to face interaction kinda guy.”

The woman laughs, “That’s what they all say, sugar. But listen, you’re lucky, there’s one girl who happens to be working tonight. I’m almost one hundred percent sure that you’ll like her.”

“Almost?”

“Trust me.”

“Yeah, okay.”

“Right, hun, so when you want to end it or decide to switch girls, just press one on your phone, okay?”

“Got it.”

“Still remember the process?”

He almost gets annoyed because he’s not a fucking idiot. Dean sighs, “Yeah, beep, punch in PIN, talk.”

“Look at you, doing your homework,” the woman teases and without even a goodbye, he’s connected to a line, and then there’s the beep.

Dean turns the card that he’s been holding all this time in his hand and punches in the PIN.

And then he waits.

Y/N’s almost done for the night. She’s spent most of her day and evening writing up her paper to turn it in on the deadline at midnight. Maybe one day she’ll learn to schedule and get her papers done way before they’re due but today’s apparently not the day.

On nights like this, she usually doesn’t take any calls but after turning in her paper, she feels like she’s riding on a high, so she sent out a text, telling Sweet Temptations that she’s going to take one call only. Maybe she needs it, needs to release some of the tension before going in to work tomorrow afternoon and facing him. It’s actually crazy to think that when she gets off while helping a client get off, it would clench her thirst for her supervisor. It probably won’t be the case and she’s willing to bet all her money on the fact that as soon as she sees him tomorrow, her stomach will flip and her heart will race and the thirst will definitely be back. It’s been constant since she started working there and she doesn’t really know what to do about it. Good thing the job’s only part time as she wouldn’t know if she could handle being around him for the whole damn day.

She tried not to let him get under her skin, she really did. It’s also not for the lack of trying, honestly. She used to go out on her nights off, meet guys, and even tried to have one night stands but they just didn’t do anything for her. The thing she found out about having one night stands is that she actually hates them. Y/N discovered that she has trouble getting intimate with someone if her heart’s not in it. That’s actually when she started picking up her second job. Working as a sex operator is kind of a compromise. This way she can still get herself off while she can shamelessly imagine that the men who talk to her are Dean. There’s absolutely no need for her to get physical with someone and then get disappointed because they are not who she really wants.

That’s right. She has a gigantic crush on her supervisor and she absolutely has no clue what to do about it. Well, it’s not that she hasn’t tried to get his attention. She has shown up in dresses, pencil skirts, revealing shirts that are probably, in some way, not really business appropriate, but so far, apart from harmless flirting, nothing has really happened. Not to say that she thinks he somehow hates her? Hate is maybe too strong of a word. At least he seems irritated by her, if his grumpiness is anything to go by.

She’s in bed when the phone rings, her vibrator and a dildo ready next to her. It’s usually not the norm that she gets herself off. It really only happens when she is awfully stressed or if Dean ignores her more than necessary. As far as tonight is concerned, she is stressed and really hopes that someone calls and that they are going to make each other feel good so she can go out and face her boss again tomorrow without feeling like jumping him every time he glances her way.

Sure enough, not ten minutes after she’s sent out the text that she’s working, her phone starts to ring.

Y/N takes another deep breath before picking up, mentally slipping into her sex operator persona.

“Hello?” She releases her small huff, her voice a little breathless. She’s been told that it sounds sultry.

“Uh, hi,”

It feels like her air has been punched out of her lungs and she’s left momentarily breathless again.

She’s sure she would recognize the voice anywhere because she hears it every time she closes her eyes and fantasizes about him. But it can’t be. Dean can’t be talking to her now, can he?

“Hello?” Comes the voice again and she realizes that she’s been speechless for far too long.

“Um, yeah, hello. How can I be of service, handsome?”

“I...uh, shit!” He curses under his breath, “How does this work? You know, I...uh, I got this as a birthday gift and my friends would kill me if I didn’t use it.” He stammers, and it sounds cute.

Y/N’s about eighty-six percent sure it’s Dean. And honestly, she doesn’t really know how to feel about that. Should she just refer him to someone else? But then he wants to know why and she’s not nearly ready to come clean why this call might be a conflict of interest for her. So, she slips back into her persona, chuckles lightly, and says, “Well, happy birthday, handsome.”

“It’s actually past midnight, so not my birthday anymore,” Dean mentions, dryly. It’s like he doesn’t really know what to do with a sex operator wishing him happy birthday — which is fair. She finds it amusing.

“Happy belated birthday, then.”

There’s a huff and she’s almost sure he’s smiling. “Thank you.”

“We don’t have to, you know, do anything, if you don’t want to. We could just talk.” Y/N gives him an out which she thinks is fair. She doesn’t want to keep him here if he doesn’t really want to be talking to her. Maybe she is hoping that he’ll hang up but also she doesn’t want him to. It’s a double-edged sword.

“I’m just,” he starts before there’s another silence. After a few seconds, he adds, “You might think it’s weird but you sound like someone I know.”

Her heart picks up its pace. Oh god. Did he find out?

Fuck, fuck, fuck. Okay, so, fuck. Okay, cool. Cool, cool, cool. Her mind’s reeling before she decides to play it cool.

Cool, cool, cool.

“Is that so? Who? A pretty girl?” She almost bites into her own fist because of how creepy she sounds.

There’s a sharp intake of air down the line and silence follows shortly after. Her heart is running wild, a little curious about who she reminds him off. She’ll probably die if he says the name of some other girl, but maybe she’s just holding out unnecessary hope.

“She is pretty,” he admits, his words a whisper, she almost didn’t hear. “But she’s off limits.”

“Why’s that?” Her heart begins to thunder against her rib cage.

“It’s a long story, which I’m sure is better directed at a shrink, no offense.” Dean almost snorts.

Y/N chuckles, “None taken, but I’m a good listener.”

“Oh, I bet you are,” his tone is teasing. “So, can I get your name? I don’t even know what I should call you.”

“Of course, handsome,” She smiles, “They call me Venus at Sweet Temptations for identification reasons.”

“The goddess?”

“Yeah.” She affirms, “Everyone at Sweet Temptations is named after a goddess, but lucky for you, I can be whoever you want me to be.”

“Yeah? So I could call you a name and pretend you’re her?”

Oh god. She’s going to die, isn't she?

“If it helps?”

“Wow, I….uh, yeah, that would help, yeah.” He sighs out, as if relief floods him.

Even though her heart’s breaking a little at the thought that he would call her anything other than her own name, Y/N plays it cool. She’ll get over it, right? It’s only once and she doubts he’ll call again.

“If you want I can use your name too, instead of you know, the usual. Handsome, stud, gorgeous. I can call you anything you want. Daddy if you prefer. Some do like to be called Sir.”

He sputters and coughs. “Yeah, no, a normal name’s fine.”

“So, what’s your name?” She asks, and again, her heart skips because although she knows it’s him, she still needs assurance.

“Dea—,” he coughs when he realizes his mistake, “Dan. I’m Dan.”

Oh my god.

Dean goes on, “And..uh, can I call you Y/N?”

Fuck.

She bites on her bottom lip so hard so as not to let out a loud squeal. Clearing her throat, she answers, “Yeah, of course. Y/N’s fine. Is that the girl who you’re thinking about right now?”

There’s hesitation before he answers, as if he doesn’t know how much he’s supposed to reveal. “Right now? I probably think of her all the time and you do sound like her, so, yeah. And I might have a crush on her, so that’s good, right?”

“Perfect.” She replies, pressing her thighs together at the revelation. Good God, Dean fucking Winchester has a crush on her! “Can I just ask something before we start?”

“Of course.”

“Why haven’t you made a move on Y/N yet?”

He makes a choking sound but manages to compose himself rather quickly, “She’s like off-limits because I don’t want to get us into any trouble, but mostly it’s because I don’t want her to think I’m abusing my power.”

Oh. That explains a lot now.

Y/N doesn’t want to sound too noisy and they probably should get this show on the road as he’s been on the phone for way too long already.

“So, Dan, are you ready?” She starts without any preamble.

“I don’t really know how to prepare myself for this,” Dean admits.

She has to chuckle briefly at that. “You don’t have to do anything, okay? Just listen to me and join in if you like.”

“‘K. Yeah, okay.”

Making herself comfortable she leans back. One of her hands holds the phone to her ear while she lets her other hand wander over her curves. She’s already naked, having prepared in advance. She does it especially when she feels the desperate need to get off.

“Are you comfortable, Dan?”

“Uh-huh,”

“Do you wanna know what I’m doing right now?” She asks with the full intention of engaging him and painting him a picture.

“What?”

“I’m laying in my bed, naked, my hand wandering around my body,” she lets out a quiet moan when she kneads at her breast and pulls at her nipple.

“Do that again,” Dean almost commands. “Harder. Let me hear you.”

With a smirk, she does, and the moans aren't even fake. It turns her on to know that he’s listening.

“Fuck,” he curses, “You sound fucking sexy, Y/N.”

Oh god, her pussy clenches around nothing upon hearing him addressing her.

“I’m twirling my nipple in between my fingers. Always so sensitive there,” she says, her breathing picking up. “Should I go further down?”

“Yeah, please.”

There’s a rustling sound and then something that sounds a lot like a zipper being pulled down.

Fuck. He’s going to touch himself and he’s doing it because she turns him on. Her mind still has a hard time wrapping around the fact that he’s turned on because of her.

“Mmh,” she hums as she reaches her clit. She dips her fingers further down, threads it through the slick of her arousal and coats her fingers in it before circling her little nub and getting herself wetter like that.

“Are you rubbing yourself, Y/N?”

“Uh-huh,” she nods, “God, I’m so wet already, Dan.”

Goddammit, it’s so hard to not let his real name slip out.

“Yeah? Why’s that, hhm?”

“You. You turn me on.”

He chuckles, and then she hears him spit somewhere. She doesn’t see it but she can imagine that he’s spitting into his palm to be able to stroke himself better. “You do the same for me, to be honest. What’s about me that turns you on, huh? Tell me, sweetheart.”

“Mmh..your voice,” she says. She doesn’t even have to think so hard about it, “It’s so sexy.”

“Is it now?” His tone carries a hint of amusement with it.

“Fuck yeah,” she breathes out, “Could listen to you all night.”

“Same to you, Y/N. Fuck, I can really imagine you now. Laying on your bed, naked and spread, flush and wet between your thighs. Making me so hard.” She can hear the fapping sound he makes as he jerks himself off. It’s such a huge turn on.

“What do you want me to do?” Y/N asks, still rubbing at herself lazily.

“Do you prefer your fingers or do you have toys?”

“I can’t get off with my fingers, but I do have a dildo.”

“Fuck,” Dean growls.

“Do you want me to use it, Dan?”

“No, use your fingers first, fuck yourself on them so that when you get your toy you’ll think it’s my cock that’s fucking you.”

Jesus, he’s so good at it, he should open his own fucking sex hotline.

She sinks a finger into her soaking cunt and it goes in easily because her fingers are tiny. Probably nothing compared to his thick digits. She immediately adds another finger and begins to fuck herself on them, trying to curve them right but it’s really hard to reach the place where she knows will get her off. “I’m doing it, Dan. Got t-two fingers in— fuck, can you hear that?”

The sloshing sound of her fingers fucking in and out of her dripping pussy is loud in the room, there’s no way he can miss it.

“Christ, Y/N, you’re so wet, huh? What makes you so fucking wet?” He groans, and it seems like he’s trying to match her pace with how he jerks himself off, if the fast pacing of the flapping sound is anything to go by.

“God, it’s you. You got me so fucking wet, De— Dan,”

Almost fucking slipped, dammit!

“Wish I could be there, Y/N. I would make you feel so good. Would eat you out, make you come on my tongue first, and then again. And only after you’ve come twice, you’d be ready for my fingers. I would slip in one first, adding another, and then maybe another, making you come on them a third time in one sitting to prepare you for my cock. Would that be good, hhm?”

“Fuck yes,” she arches her back a little when she manages to hit the spot but the sensation sadly doesn’t last. “You would treat me so well, wouldn’t you? I would love to feel your mouth on my pussy, Dan. Would love to be able to grind my soaking cunt on your face. Bet you have such a pretty face, too, yeah? A good place for me to sit, right? And your three fingers, shit, they’d stretch me.”

He chuckles, “That’s what I’ve been told, yeah. You could sit on my face for hours, Y/N, wouldn’t fucking mind.” He huffs, low and deep and so fucking sexy. “Would treat you so well, you’re right. Are you tight? Fuck, I bet you’re so fucking tight, hhm? My three fingers barely fit but I need them to stretch you out. My cock’s quite thick.”

“Oh, fuck,”

“How big’s your dildo, Y/N?”

“Probably not as big as your cock, Dan.”

Dean laughs a little, “Way to flatter me, Y/N. Take your dildo and use it, can you do that for me, baby?”

“Y-yes,” she says and reaches for it. “Gotta take it into my mouth first, warm it up and make it wet.” As soon as she says it, she wraps her lips around it, humming in approval when she pushes the thick shaft of the toy deeper into her mouth.

“Fuck,” Dean grunts, “You’re sucking it, right?”

“Mmh,”

“So good, Y/N. Bet you’re so good at it, aren’t you? Jesus, I wish I could see it right now. Wish the fake cock was mine. Always imagined that you would look so fucking beautiful with my cock in your mouth.”

She pushes in so deep until she gags.

“Yeah, just like that. Such a good girl, gagging on my cock.”

Holy shit, he’s got such a dirty mouth.

“Now take it out and fuck yourself on it, baby. Imagine it is my cock.”

Y/N places the slick toy to her entrance and pushes in. It stretches her, even with preparation and she whimpers as it goes in further.

“Good girl. You can do it, Y/N.” Dean comforts her, and then, after a beat, “Is it in?”

“Oh god, yes. It’s so big, Dan. I’m so full.”

“Good,” he whispers, “That’s good. Now fuck yourself as I would fuck you.”

“How would that be?” She smirks.

“I’d reach you so deep, Y/N, fuck you so hard and fast, would you like that, hhm?”

“God, yes, the rougher the better. I love it when I can feel it for a day longer, love it when you leave marks.”

Dean groans audibly, “Fuck, you’re killing me here.”

“Ah— fuck, just telling the truth. Would you pull my hair, Dan? Would you spank my ass?”

“Jesus, would do whatever you want me to, Y/N. Would mark you up so good. Make you mine, is that what you want? To know that you’re mine and nobody else’s?”

“God, yes.”

“Good, that’s good, because I’d like that too. I imagined so many times that you’d come walking into my office and I’d just bend you over my desk, hike up your skirt and let me pound into you while you scream for more.”

“Oh, yeah?”

“Yeah— shit, I’m close. Are you?”

“Me too,” she’s almost breathless.

“Can you come with me, Y/N? Are you going to be a good girl and do that, yeah?”

“Dan, oh god,”

“Where do you want me to come, baby?”

“I— fuck— I want you to come inside of me, shoot your cum inside so it’ll drip out of me the next day when I walk around in the office.”

“Oh— fuc—,” his words get swallowed by a grunt as he comes and honestly, that’s all she needs to come too, and she does with a high pitched cry as her whole body trembles.

It never happened before that she doesn’t have to use her vibrator to finish the deeds, and it’s entirely his fucking fault. Who knew that he’d be such a fucking great phone sex conversationalist?

Dean’s panting on the other end of the line, and she can just tell that he’s smiling. “Wow. That was,”

“Yeah,” she exhales, happy and exhausted.

“Wow,” he says again. “Thanks, Venus. That was awesome.”

“No need to thank me, Dan.” She smiles too. “I’m glad I could be of some help.”

“Jesus, you were.”

“Happy belated birthday again.”

“Have a good night.”

“You too.”

It feels clinical but that’s what most conversations are after the climax. And even so, Y/N will go to sleep with the knowledge that he thinks of her and has a crush on her. Maybe she should use it to her advantage.

Dean paces around in his office. He’s on his lunch break but somehow he feels restless. Last night was the best phone sex he’s ever had. Well, to be fair, he only had that one phone call, ever. But it’s the best sex he’s had in a while if not ever and that has probably to do with the fact that he was allowed to openly fantasize about doing it with the girl he likes and whom he is already halfway in love with at this point.

But yeah, that brings him back to his pacing.

Y/N’s about to start her shift in an hour and he fucking has no clue how to behave around her because even though it had been a great phone sex session, all he will see when he looks at her is how she sucks his dick and comes on his cock.

Fuck.

It doesn’t help that his dick is already standing at attention thinking back to last night. Thinking about her.

So, maybe he shouldn’t do it but he’s desperate for a release, hoping it’ll help him relax enough that when he sees her, he will resist dragging her into the next supply closet and do something he’ll regret.

Dean sits down, his office chair creaking a little as he leans back, and fishes his phone and the card out of his pants pockets. It’s a little weird to carry the card around but now he’s glad he did.

He dials the number and is greeted by a female voice but it’s not the same woman as yesterday.

“Hello gorgeous, how can I help you?”

“Uh,” he stammers, “Is Venus working today?”

“Lemme check, hun.” He hears the clicking of a keyboard and then she speaks again, “You’re lucky, she’s free and has a half hour left, do you want to be put through?”

“Yes, please.”

“Do you know how it—”

“—beep, PIN, talk.”

“Right, have fun!”

The beep comes and he punches in his PIN.

And then, he waits.

“Hello handsome, how can I be of service?” The all too familiar voice picks up the phone and she sounds a little breathless. He wonders if she’s already worked up or if he interrupted.

“Hey, it’s Dan,” he says, and lets out a loud sigh, “I’m sorry, am I interrupting?”

“Oh, no. I’m just finished getting ready for work.”

“Work? Isn’t this your work?”

Venus chuckles, “I have a normal day job.”

Oh.

“Shit, I’m sorry, don’t let me hold you up.” He’s about to hang up when she shouts.

“No, wait. No, it’s okay, I still have more than a half hour before I have to leave.”

Dean lets out a deep exhale, “Right. Good, that’s good, right?”

The girl chuckles, “It’s good if you can finish quickly.”

He snorts, hand palming over his clothed cock, “That won’t be a problem.”

“Oh? Already worked up, are you?”

“Fuck, yeah.”

“Should I be jealous of what or who got you in the mood?” There’s a teasing tone in her voice.

“Well, I was thinking of last night, so you were definitely involved,” he smirks, “The girl, Y/N, she’s going to show up in an hour, and I’m painfully hard just thinking about doing all the things that we’ve been talking about. I just need some release.”

“Alright, I can do that.”

“God, please.” Dean huffs, hands fidgeting with his belt buckle before lowering his zipper. He hisses out when his palm comes in contact with his hard cock. Just hearing her voice made it considerably harder. “What are you wearing?”

“A tight black skirt,” she says, “nothing underneath.”

He groans before he spits into his palm. Dean wraps his hand around his shaft and begins to stroke up and down.

“Do you always go commando at your job, Y/N?”

“Only if I’m wearing a tight skirt and this one, Dan, is very tight,” there’s a tilt to her voice as she says it. Something that drives him insane.

“God, would make it so easy for me to just push it up and fuck you for real, huh? Easy access, yeah?”

“I’d be ready for you, too, you know? I’m always so fucking wet,” she provides, and he can just tell that she’s touching herself too, even if he can’t see it.

“Yeah? And what covers the upper part of your body? Paint a picture for me, baby.”

“A— a white see through blouse,” her breathing hitches when she describes what she’s wearing. In the background, Dean can hear a humming noise. “Black lace bra, ah, fuck—”

“Jesus, are you using your vibrator?” He twists his fist at the head, his cock already so wet from all his pre-cum.

“Y-yeah,”

“You’re such a tease, Y/N, you know that? Walking around like this at your job? Making me so fucking hard.”

“O-only for you, De— Dan.”

It’s the second time she almost says his real name instead of the fake one, and it’s making his movement falter. Dean catches himself quick, though, he’s so close and the sooner they can get off, the better.

“I’m going to come,” he whispers, “Wanna fill you up, making my cum dripping out of you for the rest of your day at work, would you want that, Y/N? Want me marking you from the inside? Let everyone smell that you’ve been riding on my cock and let me creampie you?”

“Fuck— oh god!” She squeals out in delight and he’s close behind, spilling all over his own hand.

“You okay?” Dean asks with a smile on his lips. His breathing is ragged as he reaches for tissues. Glancing down, though, he sees that he’s soiled his pants. “Fuck.”

“I’m good, but what’s up with you?” She giggles and the sound really does things to him. He would never think that he could have a thing for his sex operator but here he is. But he doesn’t know if it’s really her existence that does it for him, or if it’s because she reminds him so much of Y/N. The way she sounds, and especially her laugh, that’s so Y/N and it’s fucking with his mind.

“I have to change my pants.”

Venus laughs some more, and upon hearing the sound, Dean suddenly doesn’t care about his pants so much anymore.

“Right,” she breaks his train of thought. “Feel better now?”

“Much better.” He concurs. “Thanks.”

“Anytime, Dan.”

“Right, I should change my pants.” His mouth says, even if his mind actually just wants to stay on the phone for a while longer.

“Yeah, I gotta get to work.” There’s rustling and pretty soon, the sound of water running can be heard.

“Good, I’ll let you go. And Venus?”

“Mmh?”

“Seriously, thanks.”

She chuckles, “Bye, Dan.”

Dean changed into the spare pants he keeps in his office as soon as he hung up the phone and afterward tried to get things done, distracting himself with more work than necessary and telling himself that he won’t seek out Y/N if he doesn’t have to. For the sake of his own sanity.

His plans get derailed when he walks into the break room and sees her talking to Benny.

Fuck.

She’s wearing a tight black skirt and a see through blouse. Black lace bra underneath and it’s not like he’s been staring but it’s fucking there for everyone to see and he’s only a man.

What a coincidence, though, as Venus described those clothes to him. It must be a coincidence, right? Surely, Y/N can’t be Venus. It doesn’t make any sense!

Dean wordlessly walks past the two of them and pours himself a mug of coffee. On his way out, he makes sure to get Y/N’s attention. Because he needs to fucking know.

“Y/N, can I see you when your shift ends?”

She’s mid talk and still smirking at something Benny said and when she looks at Dean, the smile travels with her and he can swear, it lights up the fucking room. But it disappears as quickly as it showed before it’s replaced by a frown. “Is there a problem?”

“No,” he shakes his head, “I just need to talk about the numbers you delivered.”

“Oh, okay.” She breathes out relief, and Dean immediately feels guilty for making her think it’s something wrong with her performance. “But it’s going to be 7 PM when I finish. Your shift ends way earlier.”

“I have work to catch up on. I’ll probably be here till late anyway.”

“Oh, yeah, okay.” She nods.

Dean sends a nod into the round before he walks out with a semi hard on and an erratically beating heart.

He’s staring at his computer, but he’s not really seeing anything. The numbers blur together, and had been starting to morph together about two hours ago. He’s about to just try to pull himself together when the knock sounds at the door.

“You wanted to see me?”

Dean’s head snaps up so fast he feels a crick in his neck and his palm immediately goes up to rub at it. “Uh, yeah, please come in.”

Y/N does while he still tries to compose himself. Dean hears a click and he could swear it sounds like she locked the door but he doesn’t dare to ask. It would be embarrassing if it wasn’t.

She comes closer. Her lips quirk up into a grin as she stands at his desk. Dean really tries not to look at her top, tries not to look at her tits. He probably fails.

“What is it?”

He quickly shuts his laptop and sets it aside, deciding that he’s done for the day as well. Intertwining his fingers together, he asks, “You don’t want to sit?”

“I’ve been sitting the whole afternoon.”

“That’s fair.”

“Dean, what is it? If you wanted to fire me you didn’t have to wait until the end of my shift.”

His eyebrows knit together, “Fire you?”

“Yeah?”

“Jesus, Y/N, no! I have no intention to fire you. Your performance is excellent.”

“Oh.” She breathes relief and again, Dean’s a dick and feels guilty. But then her lips curve up, her smirk turning mischievous. “My performance is excellent, huh?”

Dean swallows. “Uh, yeah.”

“Well, your performance isn’t bad either.”

“Excuse me?” He looks at her, incredulous.

She’s still smiling and he feels a sudden urge to wipe that fucking smile off her face. He’d like to preferably do it with a kiss.

Y/N’s walking around the desk now, coming to stand next to him and Dean tries not to openly stare at her ass in that fucking tight skirt. It makes him wonder, though, if she’s wearing panties—

“Just telling you that you’re quite good at phone sex, Dan.”

Dean’s heart bottoms out while his eyes widen in shock— or shame? Doesn’t matter. It seems all the same. He stands up abruptly with an urge to get away but she’s blocking his path.

Fuck.

It was fucking her!

And he fucking told her he had a crush on her and called her her real fucking name!

On the one hand, he wishes the ground would open up and swallow him whole but on the other hand, he’s incredibly turned on.

“Venus?”

She grins as she takes a step closer. Her chest almost touches his but not quite, but the heat radiating off her is almost scorching hot.

Reaching out, she starts to play with his tie. “Yeah, I’m sorry I couldn’t really tell you and when I realized it was too late.”

“Fuck,” he swears out loud, “Then you know about my crush on you, huh?” His ears feel like they’re on fire.

Her hand still plays with his tie and it’s distracting in the best way. Y/N’s bites on her bottom lip, which is endearing and infuriating all the same. She nods her head, “It’s okay, though.”

“Nothing is okay. I shouldn’t be, like I’m your supervisor and I don’t want you to think I’m using you. It’s not ok—”

“—Dean,”

“Huh?”

“Shut up. I have been crushing so hard on you since I started.”

“Oh, thank fucking god, and there I—”

—she pulls him down by his tie and presses her lips to his.

It takes his brain two quick heartbeats before it catches up, but when it does, Dean kisses her back, tongue getting to work and begging for her lips to part. As she smiles into the kiss while she lets him in, he wraps his arms around her, pulling her flush against him. Her hands hook behind his neck, fingers playing with his short hair.

“Fuck,” he mumbles against her lips, pulling her bottom lip between his teeth before releasing it and pecking her lips after, “Been thinking about doing this to you since last night.”

Y/N pulls back a little, raising a suspicious eyebrow when she asks, “Only since last night?”

“Well,” he shrugs before admitting, “To be fair, I thought about it constantly since the day you started but after last night, the need is almost unbearable.”

She slips a hand down his front to palm at his dick through his pants and Dean growls.

“We should probably move this somewhere else,” Dean actually doesn’t quite understand why he suggests it. Patience has never been his strong suit.

“Nobody’s here anymore.” She starts to unbuckle his belt, “Besides, didn’t you tell me that you want to bend me over your desk and pound into me?”

The noise that leaves his throat resembles one of a wounded animal.

He can’t find it in himself to care.

“The door—” He looks up at the offending door in question.

“—is locked.”

“God, you’re amazing,” He kisses her again, dirty and insistent, sucks in her bottom lip before he releases it with a wet pop. “We need to talk but only after I make you come on my cock.”

“Oh god,”

He chuckles, “Dean’s fine.”

Before she can say something snarky back, Dean has her turn in his grip and bend over his desk, and he sidesteps her to stand right behind. He runs his big palms over her taut ass. They feel better than he imagined.

His fingers grip at the tight fabric of her skirt to pull it up, and yep, she isn’t wearing fucking panties. Dean lets out a growl and slaps down on her ass, hard. He smoothes it while running his palm over the place he smacked. “That okay?”

“Fuck, yeah,”

“You’re a naughty girl, Y/N. Walking around pantiless the whole fucking afternoon.” He kneels down and without any preamble, buries his face right in her cunt, tongue lapping at her slit, eager to taste her. His palms are on her ass, pulling them apart for better access. Her heady taste hits his tongue and explodes on his taste buds. He groans because it’s sweet and fucking intoxicating.

She moans out loud. It sounds better than through the phone.

“I was right,” he whispers and breathes in her scent. It’s intoxicating. “You taste divine.”

“Oh god.”

He spanks down her cheeks again, making her hips jerk, and he smirks cockily, “Told you, Dean’s fine.”

With a last suck on her clit, he lets go and stands back up, pressing his erection against her ass as he opens her up on his fingers. “Jesus Christ, Y/N, you weren’t lying when you said you were tight and wet.”

“I always am for you.” She manages to croak out and he makes her choke on her words when he adds another finger, and another. It’s a fucking tight fit, making him grunt when he thinks about those walls stretching to accommodate his cock.

His other hand works his zipper open before reaching in to take his cock out. He slaps his hard length against her bare ass, while three of his fingers prepare her for his dick. “Shit, Y/N, I don’t know if you can take me.”

“I can!” She shouts, and maybe he should care that they are being so loud but he just can’t bring himself to. Whatever, if he gets fired, it's probably worth it. He knows he isn’t thinking straight but he’s just not able to. His mind is clouded, his senses burn with desire. “God— Dean, I— I need,”

“What do you need, baby?” He pulls his fingers out and they come out dripping. “Fuck,” Dean licks them off while he sucks pleasurably.

“Fuck me. I need you to fuck me. Bare.”

He chokes on his saliva.

“W-what?” He asks but can’t ignore how his dick twitches at the thought.

Y/N looks back over her shoulder, batting her eyelashes, and he already knows with his whole being that he wouldn’t be able to deny her. “You said you want to, and I want you to.”

“Y/N,”

“I trust you. Do you trust me? I’m on birth control and I’m clean.”

Dean slides his dick through her slit, mock fucking her and it already feels too good. He swallows.

“You know I wouldn’t do anything to endanger you, right?” He asks, sounding almost as wrecked as he feels.

“I know.” She nods her head. “Dean?”

“Yeah?”

She wriggles with her ass, “Fuck me.”

He growls, one hand holding his shaft as he places his dick to her slick entrance. She widens her stance to allow him to reach her better and whimpers when he pushes the tip in.

With only the edge inside, he places his hands back on her hips, fingers digging into her flesh so deep he’s sure she’ll bruise. Good, he thinks. He wants to leave marks everywhere.

With one hard thrust of his hips, Dean buries himself as deep as he can go, feels her walls stretching and contracting all around him. Heaven. It feels like fucking heaven, and he groans when she jumps forward on impact.

“Oh my god,” she mewls.

“You good?” Dean waits it out, wants to hear a confirmation that she’s okay.

“Shit, you weren’t lying about your thick cock,” she breathes out, her fingers digging into the wood of his desk for purchase, leaving behind shapes of crescent moons.

He chuckles and rubs a palm over her bare and biteable ass, “I never lie about my cock.”

“Y-yeah, I’m okay. Fuck me now.”

“Beg for it.”

She groans but it’s more with amusement than annoyance, “Please?” She begs, “Would you please fuck me with your thick cock, Dean?”

“With pleasure,” he quips and proceeds to pull himself out of her soaking cunt only to drive back in with force, pushing her further against his desk and she squeals with glee.

Dean continues to thrust into her, fast, hard and relentlessly, the sound of bodies slapping wetly together loud in the room.

“Y/N, fuck, you’re taking me so well,” he manages to croak out between his heavy breathing, “Just like I knew you would. Such a good girl, huh? You feel fucking amazing.”

She answers him in whimpers and moans and to know that he manages to reduce her to those sound, makes him want to blow so fucking bad.

At one point, he pulls her up by her hair, making her arch her back as he wraps one strong arm around her middle to support her while he fucks up into her.

After a while, his hand wanders up below her shirt until he reaches her bra. With one swift tug, he pulls one of the cups down and twirls her hard nipple between his fingers, making her keen in delight and her pussy clench around him. Christ, she wasn’t lying when she said she has sensitive nipples.

He licks below her ear and whispers against her throat, “Go on, rub yourself, make yourself come for me, baby. I’m close but I wanna feel you come on my cock.”

“Uh-huh,” she keens. One of her hands holds him around his biceps but her other one sneaks in between her thighs to rub at her clit.

“That’s good. Just like that,” he praises when immediately after she starts to stroke herself, he feels her walls tightening around him. “Come for me, Y/N, come around my cock so I can fill you up. ‘Cause that’s what you want, isn’t it? So hungry for my cock and cum. Such a filthy girl talking on the phone and making yourself cum with strangers. But you’re mine now, aren’t you? Mine to fuck. Mine to mark up. Mine to fill.”

“Oh— fuck—” she almost shrieks when she comes, her knees buckling and if it wasn’t for his arm around her, she’d drop to the floor.

He kisses the side of her throat as he continues to thrust through the tight clenching of her cunt, and it’s not even half a dozen hard thrusts later that he spills his cum into her, grunting and groaning as he sucks at the patch of sensitive skin just below her ear.

They stay like that a little longer and his grip loosens a little so she can twist her upper body and look at him. There’s a satisfying smile on her face and Dean dips his head down to kiss her.

Later, when they are dressed and she waits for him to collect his paper and put them away, she comes to stand next to him and from his place on the office chair, he can clearly see that something murky has left a streak down the inside of her thighs. He’s almost instantly hard again knowing that it’s his cum.

Grabbing her by her wrist, he pulls her into his lap and she falls in sideways.

Dean noses at her temple, “So, I was thinking we go out for dinner, maybe a drink if you can hold yourself back from jumping on my cock. Then I’ll eat you out for dessert.”

Y/N laughs, the sound bright, and it makes his heart swell a couple of sizes. “Yeah?”

“Yeah,” he kisses her cheek, “I was also thinking we can keep doing that. Going on dates, having amazing sex. I don’t like the phone sex thing, but I know you need the money, so I’m okay with you working on the phone but I have a condition.”

Her eyebrow quirks up and he has to grin. “What condition?”

“You’re only allowed to pleasure yourself and make yourself come with a client on the phone when I’m there too.”

She seems to think about it, and he doesn’t know if he already lost her before this can even start, but then her lips break into a wide grin, and that’s when he knows that he’s going to keep this girl forever. “Deal.”

They seal their deal with a kiss that grows heated too quickly and he has to break it off just to be able to function, and somehow he really wants to get out of here.

“Another thing,” he adds when she lifts herself off of his lap and Dean’s heart does a crazy skip because he misses her weight already.

“What thing?”

“We maybe should not do it in the office anymore.” Believe it or not, it physically hurts him to say those words.

“That,” she quips, “I can’t promise.”

He groans and pretends to be annoyed but honestly, he kind of looks forward to how she wants to convince him otherwise.

***

Three Months Later

They are in bed with his head between her thighs when her phone rings. He deliberately sucks harder and does the thing with his teeth that make her go wild.

“Hello, handsome, how can I be of— shit, oh god!”

Dean chuckles, looking up at her smugly.

She rolls her eyes and grabs him by the hair, nails digging into his scalp to chastise him. He melts against her touch.

Dean returns to eating her out when he talks again.

“I’m sorry handsome, I’m already worked up. Imagine you in between my thighs, sucking and licking at my wet puss— fuck, yeah, just like that, oh god, I’m gonna—”

Y/N buckles her hips, and Dean has to hold her down as she comes, her slick soaking his face. And he still thinks it’s the fucking best thing.

“Oh, gorgeous, you make me come so hard,” her voice is strained, it sounds absolutely sultry, and Dean’s almost ninety-seven percent sure that she’ll get good tips from that client.

She doesn’t do it as often anymore. Maybe once or twice a week, and it’s only going to last until she graduates. Dean thinks he can live with that, and as the deal they made at the beginning, he’s always there when she takes calls and it’s also a win-win for both of them because he can make her come while she makes some money.

“Is that so, huh? You want me to suck on my dildo so that you can imagine it’s your cock?”

Dean’s already up and scrambles to sit against the headboard, his thick cock hard and leaking as he grins so bright it hurts him a little.

She gets on her knees, rolling her eyes, but when she lays between his spread thighs, she looks at him fondly. He wriggles with his eyebrows when she takes his dick in her hand.

“God, your dick is so thick and hard,” she moans, and Dean can guess that the man on the other line is totally believing her lies. It gives him a weird kind of satisfaction to know that she thinks of his dick only. “I’m gonna try to take it deep, okay handsome?”

Dean nods enthusiastically with his trademark crooked grin, and she winks at him when she starts to lick up his shaft, humming appreciatively.

And when she gags around his cock, Dean almost moans out loud.

Next week will be her last day at the office because she already has another better paid job lined up, but she’s also going to move in with him, so he really can’t complain much. Once Y/N is not working with him anymore, he will invite his friends to the bar and pay for drinks all night because if it wasn’t for them, they definitely wouldn’t be together and he’d still be a pathetic, pining idiot that would have gotten his heart broken when she left.

Please share your thoughts with me, I’d love to hear your feedback.

#smooth operator #dean winchester #dean winchester x you #dean winchester x reader #dean x you #dean x reader #dean winchester fic #dean winchester fan fic #dean winchester fan fiction #nathalie writes

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