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remotewatch · 2 months

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for this simp I have no sympathy 💳🏃‍♀️

Jack Schlossberg x reader | 3.5k wc

summary: Jack’s a great boss. He doesn’t care how often you work remote, the benefits are actually competitive, and he lets you run up his Amex as long as you’ll spit in his coffee. Wait, what?

cw: shameless smut, fingering, oral (f receiving), sugaring, inappropriate workplace dynamics, findom, submissive loser jack, ooc (he’s at the office), spit kink, semi public sex?, he calls the reader a bitch but doesn’t mean it, somehow a plot snuck in here, def needs a part 2 eventually

AN: this one goes out to @augustghosts !!! Happy happy birthday and thank you for matching my freak mwah

minors dni pls I don’t want y’all thinking this is realistic or healthy

It’s a technically perfect relationship, as much as you’re aware of the risk of it all going to shit at any moment. Somehow that thought always pops back up at the jewelry counter. Your eyes trace aloofly over the puddles of diamonds littering the cobalt velvet tray before you and finally land on a comparatively understated anklet.

“I’ll take this one, please.”

“Excellent choice, madam.”

You waste no time shoving the evidence of your purchases into an overstuffed trash can prior to slipping the anklet on and dashing to the coffee shop closest to your building. As you wait outside, you can’t help but wonder if you’re visible from Jack’s office. You absolutely are, and he’s been glued to his window like a creep trying to pick your hair out of the crowd since the moment you left, but there’s no way for you to know that.

The line moves faster than usual, and, soon enough, you’re balancing 4 orders of varying sizes with your work tote in one hand and carefully removing the lid of Jack’s cup with the other. Black with half a pump of sugar free vanilla and the massive glob of spit you deposit in there as you traverse the crosswalk.

It had started rather innocuously, and you probably wouldn’t have ever picked up on anything if he didn’t have such an awful poker face. There was a work dinner, some dick of an exec retiring, and out of the corner of your eye you’d spotted Jack placing his personal card in with his company one when the bill came around. That was a little weird. It was much weirder that he looked like you’d caught him pissing in the break room sink when he realized you’d noticed.

Once you had, it was hard not to spot the gunmetal edge of his black card peeking out from under the company one at every single outing, though you made a point to feign ignorance. You’d asked one of your coworkers about it after you had to skip one night to visit family, but she was just as clueless as you felt.

“I was sitting next to him the whole night. He only used one card,” That forced you to backpedal and pretend you must have been mistaken; no sense in drumming up gossip before getting to the bottom of whatever it was.

Still, work was work, and things had been so hectic that the guilty look on Jack’s face had nearly faded from your memory by the time you came storming off the elevator two weeks later, drenched from forgetting your umbrella, one heel broken, and late for the first time since you’d been hired. You’d been so focused on wringing out your sweater that you had no chance of hearing or seeing him round the corner until he was already crashing into you and spilling (thankfully) lukewarm coffee down the both of you. If that didn’t push you over the edge, his attempt at a joke to lighten the situation certainly did.

“God, Jack, is everything a fucking game to you?! Fuck off!!” came flying out before you could stop it. Your only saving grace was that your entire team was already in a meeting across the floor, but that didn’t stop you from retreating to the bathroom and leaving him no time to say anything.

You were so beyond screwed. You’d busted your ass to get this job and had completely blown it over spilled coffee of all things. By the time you’d dried yourself to a somewhat acceptable level and crept over to the closed door of his corner office, the stomach-dropping dread of plunging back into the job market was already settling in.

There’s a weird clatter when you knock, and Jack looks the slightest bit frazzled when he opens the door, a few curls of his usually annoyingly perfect hair sticking up on one side.

“Can I apologize?” He stifles the smirk that’s tugging at the corners of his mouth like he’s afraid you’ll scream at him again.

“You don’t need to apologize, but sure. Come in.” At any other time, you’d feel dangerously comfortable in his office. It’s not corporate at all: so packed with weathered sunshine-smelling afghans and little wooden beach trinkets that seem to multiply every time you leave that it feels more like an antique store than a place of business. Today, the sight of it all makes you nauseous as you try to do damage control.

Thankfully, he cuts you off before the stammering mess of a groveling attempt unravels completely.

“Really, it’s fine. Do you think I can afford to fire anyone right now?”

“I guess not?”

He can’t quite conceal a wince when he sees the puddle you’re leaving on the carpet despite your best efforts.

“Well, you can’t work all day dressed like that. Would you go across the street and let me get you something new? I’ll call and tell them you’re coming.”

“Jack, I’m not going to Loro Piana for a change of clothes. It’s one day, it’ll be fine-“

“Please? And then we can forget all about this and just focus.” Fuck. His mouth looks so good asking nicely. The implications are not lost on you, that you’re crossing a VERY stark line here, but the way he’s looking at you with those perfect fucking doe eyes has your brain buzzing too loudly to care as much as you probably should.

The staff are even more attentive than you’d expect, to an almost unnerving degree. You’ve barely set one foot in the door before your coat and bag are lifted off you and you’re whisked up to one of their VIC suites. There’s already a rack waiting for you, but the sales associate’s not so subtle mention of a shower in the suite seizes your attention. Even though it’s only ten minutes, the water pressure and whatever is in that body wash make you feel like you’ve fast forwarded through a week at the spa. When you step out and look around for your old outfit, you’re timidly informed that they’ve been taken to the dry cleaner as per the cardholder’s request.

“Oh, yes. Thank you, I must have forgotten,” you mutter in a deeply unconvincing attempt to give the impression you’ve been in a dressing room this nice before. As tempting as it is to thumb through all of your options, you can’t afford to waste any more time and throw on the first two pieces on the rack: an ecru knit trouser and short sleeved sweater set. One of the price tags flips over as you tug them from their hangers, and you have to take a deep breath to stave off the tunnel vision the number on it inspires.

Of course, they both fit perfectly and feel like an absolute dream. As soon as you begin to move towards the door, the same sales associate pipes up again.

“Mr. Schlossberg mentioned that you were also interested in some leather goods. Is that still the case?” You turn to see a massive array of belts atop a disgustingly ornate glass (or is that crystal?) table along the back wall with a dozen pairs each of coordinating loafers, oxfords, and pumps underneath. A small sliver of guilt turns over in your gut; you really shouldn’t, but fuck it, that line has already been crossed, and you can’t even pretend it’s a difficult decision.

“Yes, I was! Thank you so much for reminding me!”

She helps you settle on a pair of gleaming chestnut loafers with a narrow matching belt, and you choose not to dwell on how Jack knows your exact clothing and shoe size.

You hate how much of a spring it puts in your step as you hurry back across the street. The meeting is somehow still going on, so you quickly pop over to Jack’s office to thank him again and definitely not to show off how sweet your ass looks in these pants.

You’re so ecstatic from the whiplash of remaining employed after telling your boss to fuck off right to his face that you stupidly swing his door open without knocking first.

Jack slams his laptop shut, but the audio pause is delayed, and the there’s nowhere for him to hide as its speakers blare out clear as day:

“-my perfect good boy. Give me all your cum. Yeah, you’re my favorite ATM.”

The secondhand embarrassment is absolutely brutal, so you imagine his stomach is falling out of his ass right about now. He purses his lips together as he stands up painfully slow, fingertips pressed to the desk so hard they’ve lost color. God, he’s never this quiet. By the time he stalks over to your side of the desk and leans back against it, your heart is pounding so erratically you think you might drop dead right there on his pashmina rug. The new outfit suddenly feels heavier, like every wordless second he spends squinting at you adds a few ounces to the knit. Your suppressed sigh of relief forces its way out of your nose when the next words out of Jack’s mouth aren’t “go pack your desk”.

“Do you plan on telling anyone about that?” His expression is totally unreadable and it’s freaking you out; you don’t think you’ve ever seen him completely serious, even in the most dire of time crunches.

“No. Am I still getting fired?” This time, Jack lets a smile bloom across his face like he couldn’t stamp it down if he tried.

“I don’t think I could ever bring myself to do that.”

Once again, some would say stupidly, your relief emboldens you.

“Why do you use two cards when we all go out?”

He gives your outfit a slow once over that would be repulsive coming from anyone else before glancing at the idle laptop, then back at you with a sprinkle of condescension mixed with his normal charisma.

“I like buying you shit.”

The frankness of it all is embarrassingly hot.

“And it doesn’t feel the same using the company card?”

“Not at all.”

That sliver of guilt is back, but it feels more obligatory than genuine. It’s currently being steamrolled by carnal curiosity.

“Why do you like it?” Jack’s eyes are practically sparkling with anticipation as he glances down.

“Why didn’t you turn down the belt?”

He presses his luck when you hesitate to respond. “There’s nothing wrong with enjoying nice things, you know.” Still, nothing, so he strolls over to the floor safe and hands you a bulging cash envelope from its contents.

“For your rent, or whatever. So you know I’m serious. You don’t have to do anything else, but I want to ask for one favor before you get back to work.”

Your throat dries up, and your expression must betray your assumption and feelings because he’s quickly correcting you with a small chuckle:

“No, not that,” as he’s twisting the lid off his thermos and handing it to you. That’s weird, but whatever. You’ll happily take drinking out of his mug over bruising your throat if it comes down to it. Jack gently pushes the rim down away from your mouth with two spread fingers when you go to take a sip.

“Would you spit in it? Please?” This time, you don’t give your doubts a chance to articulate themselves.

It hits the insulated inner wall with a shrill ping and drips slowly down into Jack’s coffee, and before you have a chance to fuck this up, you’re forcing the tumbler back into his hands and retreating to the doorway, envelope clutched in a death grip.

“You have a call at eleven. It’ll become my problem if you’re late again, so maybe figure something out.” you suggest on your way out. Just as the door clicks shut, you fail to stop yourself from turning back and get an eyeful of him swirling the mixture like he’s at a wine tasting and gulping it down in one shot.

Your new arrangement develops rather quickly after that. Now that he’s no longer trying to conceal his interests, Jack is practically falling at your feet whenever the two of you are alone. The rest of the team is already used to you showing up early and staying late, so what difference does it make in their eyes if you’re actually doing work or dragging him around his office by his tie and beating a raise out of him with his own shoes? Initially, you shy away from indulging as much as he’d like and keep your authorized user status just for groceries, rent, the boring shit. It’s not until the first time he sits you down in his chair with his laptop open and tells you not to stop shopping until you’re squeezing his tongue that you allow yourself to see the real appeal of having an unlimited credit line. He’s already got your info on autofill; god, what a thoughtful little freak, you think as you book recurring massage after manicure after private museum tour after clearing out your Bergdorf cart. The digits and commas are blurring before your eyes as you struggle to navigate the Cartier homepage, and soon you’re just clicking add to cart on anything that slightly catches your attention. You cursor twitches once, twice, in time with the unrelenting work of his fingers (he refuses to roll up his sleeves, says he loves you sticking to his cuff links), but you manage to click purchase all before focusing your full attention on your incoming orgasm.

Jack tugs his phone out to check his pending charges without letting your clit slip from between his lips, and the elated moan he lets vibrate through you when he sees the final total has you drenching him down to his shirt collar.

Since he’s always this desperate, it’s hard to play along with the little song and dance he does of pretending you need to rein it in. You have to bite your tongue to not laugh and just say “no problem!” every time he requests that you please stay within budget today after his first sip of spit coffee. Obviously, there’s never been one; the only parameter you give yourself is a minimum of two supremely gaudy purchases per week for him to “notice” so you can get the ball rolling. Like today. Your new heels are hideous and feel like they’re lined with steel wool, but they fulfill their duty of catching the attention that was already yours to begin with.

“Those aren’t the shoes you had on this morning.” You don’t even glance up from your monitor.

“Nope.”

“When did you find time to go to Saks again?”

This time, you give him a look like he’s 500 years old and couldn’t rotate a pdf to save his life.

“I was working remote from their cafe. The chairs are really nice.”

“Yeah, they’re real nice in my office, too.” It’s clearly not a suggestion.

As per usual, you elect to sit on Jack’s desk just to needle him. When he lifts your leg to get a better look at the new heels, his nose crinkles up in disgust.

“These things will fuck up your back.”

“They’re car to table only, you should know that.” Your other foot swings around to tuck against his sacrum and nudge him in between your legs.

He’s trying his best to act upset, but you can feel his dick throbbing through his slacks.

“How much did you spend today?” You make a big show of pretending to think for a moment.

“I’m not sure. More than you made?”

“You fucking bitch,” And that second leg is shooting up between you and kicking him back hard enough that he bumps into the filing cabinet.

“I ought to report you to HR for that.” only then does he notice the anklet, glinting wickedly under the soft amber lights. Jack pulls your foot closer and with frighteningly little effort nearly tugs you straight off his desk.

“Is this new, too? How much?” He’s got the same look on his face as when his manners are wearing thin on the phone, all carefully applied nonchalance ruined by the the ravenous impatience in his eyes.

“Ten,” and he straight up shudders. He presses the cool platinum against his cheek, and his eyes slip closed as he jerkily ruts against you. Through three layers of fabric, you can still feel every bend in his pulsing underside vein.

“You didn’t think to ask me first?”

“Why would I? It’s my money.” The choked up sob that spills out of him is abruptly morphed into an irritated groan by a knock at the door.

“Fuck, I can’t deal with this. Get rid of it.”

He’s plunked you into his chair and scuttled under the desk well before you can remind him that that’s not in your job description. Jack pulls your seat close enough to shove his nose right into your cameltoe just as the door swings open and one of your least amicable clients comes stomping in.

“Where the hell is he?! First it was ‘email me in a month’, now his direct line calls are getting dropped! My intern had to show me his fucking Instagram to prove that he was even in town!” And he keeps going, but you struggle to register any of it over Jack ever so politely licking you over your stockings like he’s taken you out for a lovely date first and not at all like he’s using you as a human shield to deflect this moron.

“I’m sorry. He’s not currently available.” Jack vacuums your clit right into his mouth at that, rolling and twisting his tongue over it like it’s a goddamn ring pop.

“That’s a load of horseshit. John’s never worked hard enough to be this fucking unreachable. Where is he?!” Normally, you’d be at least a little concerned about how close this guy looks to throttling you for your boss’s location, but the way Jack’s cheeks stick and unstick to your thighs as he rocks his head as best he can in the confined space is diverting most of your attention.

“I understand your frustration, sir,” your customer service voice wavers as he relentlessly sucks you through the fabric. “But there’s simply nothing I can do. Mr. Schlossberg is in meetings for the rest of the day and specifically asked not to be disturbed.” You press a warning foot against his dick, and he groans so loud you’re forced to squeeze your thighs around his head and cough to muffle it. Luckily, the client is too far up his own ass to notice.

“This is outrageous! He can’t just blow everyone off forever because his name is on the fucking building!”

“Your concerns are duly noted. Can I help you with anything else?” He’s already halfway out the door.

“Oh, go fuck yourself!” is yelled half at you, half in hope that Jack is in earshot. As soon as the door slams, you’re scooting backwards and pulling him after you by his shirt. Not that you’d have to, as he’s crawling to chase you across the carpet until you’re pressed right up against the floor to ceiling windows and white knuckling his armrests.

“Wolford doesn’t make these anymore!” you protest when he shreds your tights down the middle to lick you properly. You feel more than hear him laugh in response, and you swear you also detect a muffled “womp womp”. He always fingers you like shining up your seat is the whole point, like he’s only doing this to get to crudely lap and slurp the results up from under you just to spit them back onto your clit. You’re beginning to suspect he only took up bouldering to improve their endurance for you.

Jack finally relents when you twist both hands deep into his hair and drag him off of you. It’s gone curlier around the edges from his efforts, and paired with the overly dramatic lip smack and megawatt smile he hits you with, you can’t even pretend to be annoyed.

“You don’t seem that broken up about it.” He presses one more kiss to your clit before standing up and turning back to the file on his desk without missing a beat.

“Anyway, T&G wants this cleaned up by Thursday, so we should probably get back to it.” There’s no way he’s serious; he’s just trying to rile you up by pacing around, yapping and aimlessly shuffling papers with bubbles of saliva and pussy juice sliding down his face, but you hate that it works so well. Before you realize what you’re doing, you’ve wrapped your fingers around Jack’s tie and abruptly pulled him back down onto all fours, sending the unstapled proposal scattering across the floor.

“Nothing will happen to our portfolio if you just shut the fuck up for five minutes,” He’s all too eager to screw the rest of the day’s schedule when he rests his chin between your legs on the chair’s seat and grins cheekily up at you.

“Only five?”

#jack schlossberg #calling all cherry emoji addicts #fawn wearing uggs enjoyers #unreleased Lana enthusiasts #come get ur food #don’t get on my case about verb tenses I know what I’m doing and I’m having fun #you can be the boss slowed reverb #don’t ask me what his job is #I have no business calling him weird or gross when I’m doing all this #tell me i’m your national anthem #jack schlossberg x reader

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