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off to the races

a/n: if you’re having trouble picture what the dress looked like its here! anyways i loooooved writing the banter between them. here’s ceo-daddy-whatever-you-want harry going on a date with bartender!y/n :*

w/c: 5.4k

warnings: this has explicit hard drug use! if that’s not your thing please don’t read this! i certainly don’t recommend anyone use any drugs and it solely exists for the sake of this plot! also he rails her

***

Courtney stormed into the kitchen from the bar, untying her waist apron as gracefully as she could and throwing it on one of those metal rolling counters. "Have I ever mentioned I hate my job?" she bit as soon as the door slammed shut behind her.

You finished your glass of ice water, bracing yourself to go out there yourself. You relaced your shoe and adjusted your own apron. "How bad could it have been?" you asked only half rhetorically.

"He asked for a virgin martini!" she huffed, pulling the hair tie from her thick dark hair and letting it spill into her face. "Do you want me to bring you an olive in a glass?"

You laughed, mirroring her actions by tying up your own hair. "No way. You're exaggerating."

"Y/N, I argued with this elderly man for three whole minutes. He insisted he came in last week and was served a virgin martini and it was the best thing he'd ever had in a bar." Courtney went back to fish through the pockets of her apron to get the money she'd collected from the tip jar.

"Oh, are you talking about the guy that just left?" Becca, another coworker, asked from the sink. "Yeah, I served him last week. I gave him a martini glass with water, lemon bitters, and a splash of cranberry juice. Told him I cut it with a 'virgin wine'. He tipped me a $20," she brushed a chunk of blonde hair that fell into her face and went back to washing the dishes.

"God, thanks for letting me know!" Courtney groaned, counting out her share of the tips, pocketing the money and giving the rest to you. "Have fun out there. I think some business meeting was in town so there's a bunch of gross older men out there wanting their fuckin' margaritas." She casually popped open the first two buttons of her uniform's black button down as she stuffed her money in her chinos pocket.

"Watch your mouth!" Becca yelled, making the other girl laugh as she clocked out. "You'll be fine, Y/N. Rich guys tip well!" she encouraged.

"If they tip you at all," C warned just once more before slipping out the back door.

You shrugged your pessimistic coworker off and went out into the bar. The new girl who'd been out there alone seemed relieved to see you, as it was starting to get a little hectic. "What can I make for you?" you asked her, at the same moment that she shoved a sticky note covered in drink orders in your hand. Okay, time to get to work.

***

You'd been working at an upscale bar for about four months now. It had always been a dream of yours to work as a bartender, and you put yourself through the first three years of college working in and out of dingy places near your campus. Just as you started your last year towards your degree, the owner of your current workplace visited your bar by sheer chance and was impressed by you and offered a job on the spot. Your new pay was nearly double your old wage and you made much better tips, but God the patrons were terrible.

Working at a bar is virtually never smooth sailing. No matter where the joint is located, you get most of the same problems. Making drinks can get messy, and all the handiwork involved in you job made nail polish impossible. Some guys got way too fucking drunk. They tried to drive home after just one too many beers. Even the snotty rich fellas would put their manners side and start shoving others around if they thought someone was ogling their wife in a weird way. These were no picnic to deal with, but working in the nicer areas came with its own set of challenges.

Y/N learned almost immediately that rich guys were ridiculously entitled. No matter which order you serve them, at least one of them will gripe by the time you reach them. Some of them made gross comments (fortunately, your boss has a no-tolerance policy for this and with a wave of the hand, a bouncer would carry out the offending customer). They complained about how well their drinks are made and demand them to be redone. Working at shitty bars had way more freedom, because regardless of how you treat the obnoxious customers, you'll still have people who come back. But in the nicer places, reputation matters. Sometimes you have to remake that drink, even if it just means transferring it to a different glass and adding new garnish when they're not looking and handing it right back to them.

That almost always works, by the way.

Anyways, the day was terrible, just as Courtney warned. It was a Murphy's Law kind of shift and nothing sounded better than going home, kicking your shoes off, and never having to live this day over again. Fortunately, she'd been wrong about the tips and you'd had to send your coworker back at least three times to dump the tip jar out back in the office as it had been overflowing. But did it make up for how lousy the rest of the shift was? Maybe. A little.

The most beautiful words a bartender can hear are, "We close at 11." You had worked at places that stayed open until as late as 2 AM, but your current bar was closed and locked up before the day even changed. Your shifts were great, typically only being about four or five hours and getting home at reasonable hours, but the time spent there just felt tedious.

You swore it was a human instinct to check your watch incessantly whenever it's the last 15 or so minutes of your shift. Even when there was so much left to do, something about twitching to look at your wrist too often was so much more appealing than working. Usually, the only thing to stop the tick is if an interesting patron walked in.

And one did.

He was tall, commanded the room, dressed up but in all black. His hair was timelessly loose and curly, and his hands peaking out from his blazer sleeves revealed that he might be hiding some tattoos. It was suddenly like you weren't wearing a watch at all.

"What can I get for you, sir?" you cooed, maybe just a little off the mark of being subtle.

"I'll take a tequila shot, and pour one for y'self, too," he said deeply, sitting at the bar and combing through his locks with his fingers. He intimidatingly peered over you as you awkwardly scrambled around.

"I think y'know I can't do that, sir," you said apologetically, fishing out a glass and breezily pouring a shot. While putting the bottle of tequila back, you grabbed some abandoned empty glasses from the bar and moved them behind the counter. Your coworker had gone to the back an hour ago to close the kitchen, and multitasking happened to be one of your strong suits.

"I don't, actually." His hand came up to rub at his bottom lip, and you noticed the nails were painted a dark blue, almost black. The other hand grabbed the drink you slid towards him followed by a lime wedge. He didn't take it yet.

You pulled the white towel off your shoulder and wiped down the area in front of you. "It's the X-ray problem at the doctor's."

The man's pointer finger spun around the rim of the glass. "I'm sorry, the what?"

"Okay, so, you're an adult man. I assume you've been to the doctor's before."

"That'd be a correct assumption, yes."

"Have you ever had an X-ray done?"

He raised an eyebrow. "I feel like everyone has."

"Probably most people. Anyways, the doctor tells you the X-ray is completely safe, but they go to Egypt to push the button."

The man laughed, and it was honestly music to your ears. You even felt your mouth involuntarily curl up a tiny bit. "You're right. But what's that got to do with this?" He lifted the shot glass and gestured towards you with it.

"The amount of radiation that one X-ray exposes you to is so negligible its rounds off to zero, but if the doctor stands in front of the machine for 8 hours every single day he goes to work, he'll definitely get every kind of cancer." You picked up a shot glass from the stack of them behind the counter. "If I have just one shot with every person who asked, I'd definitely get alcohol poisoning."

He let out another one of his gorgeous laughs, and you could no longer hold back a bashful smile. "But is the bar not about to close?" he asked.

"We are."

"And you don't seem drunk at all t'me," he hummed, scratching his stubble.

"You're quite observant." You nodded approvingly towards an old man on the other side of the bar who drained his lager glass before tossing a few dollars into the tip jar and shrugging on his coat. You rinsed the glass in the sink before putting it in the tray to carry to the back.

The man at the bar dragged his eyes at the leaving customer, aware that you and him were now alone. The shot he'd ordered still sat in front of him. "So I guess it couldn't hurt to actually have just one, hmm?"

You wiped your hands on a clean towel, thinking it over. To make the deal sweeter, the man pulled out a $50 bill and put it on the counter between the two of you. In all honesty, you weren't impressed. This was a nice bar, to be fair. It wasn't completely rare that big shots and new money heirs came in and shoved their fortunes down everyone's throats by getting everyone's tabs and tipping in the double and triple digits. His money didn't make you shrug and pull out another glass to fill-- no, it was something else.

He seemed so familiar. You couldn't put your finger on it, but something about him felt like you knew him already. And frankly, he did make a good point. The day had been super rough, your feet were aching, and you hadn't had a drop to drink all night. Even taking the tip out of the equation, it didn't sound like a terrible idea. What would one little shot hurt?

You dabbed some water on the back of your hand and salted it, though he went straight for licking his own hand. Once the two of you were ready to take your shots, he raised his glass towards you. The smirk on his face when you clinked your glasses together made something swirl in your lower belly, but you knew the tequila would extinguish that feeling immediately.

Lick. Shoot. Suck. You'd been a pro at this since that spring break you and your friends took to South Padre Island freshman year. The liquor barely even burned at this point, and you hummed while biting at the lime in your mouth as the man sputtered just a little bit.

"Here," he groaned, picking up and trying to hand you the $50.

You waved your hand a bit at him, reaching your hand up to let your hair out of the tie. "Don't even worry about it. You were fun talking to, it's not necessary."

"I insist." He seemed steadfast, and you didn't feel like arguing. You sighed and took the money gratefully, moving to slip it into the pooled tip jar. His hand suddenly shot out and grabbed your wrist gently. "I didn't put it in the tip jar for a reason."

You breathed through your nose carefully, a little turned on at his boldness. Your hand slowly retreated and stuffed the bill into your back pocket, and the man smiled once more.

He tossed a bit more money onto the counter to pay for the shots you two just took, and scribbled something out onto a napkin. He nodded towards you and left the bar just as the clock struck 11. Becca emerged from the back to go lock the front door and didn't seem to notice you were frozen. When you finally grabbed at the napkin he'd left, it was difficult trying to read his scrawled handwriting. "Harry," was the only thing written on it, followed by 10 simple digits.

That's when it finally clicked. This was Harry, the frontman of that band from ages ago. You remember your younger sister being a huge fan of them maybe ten years back, but it was a bit out of your generation. He seemed so much older now with that behind him, and he was quite charming. And you just got his phone number!

You stuffed the napkin into the same pocket as the money he'd given you, hurriedly cleaning the bar and getting ready to go home. You didn't tell a single coworker who you'd just talked to and clocked out as fast as you absolutely could. It almost felt like it didn't really happen, and if you talked about it out loud it would turn out to be a twisted elaborate dream.

Another pro of your bar's early close: busses were still running to take you home after work. On the way back to your apartment, you typed out a quick text to your new friend. I don't suppose I ever told you my name. I'm Y/N

Quick and simple. Not wasting time. You'd never been one to be patient or drawn out, and assumed most people didn't either. Playing those wait-three-days games had ended up fizzling out most of your friends' relationships and you hated to see it.

He responded. It was lovely meeting you, Y/N

Your lips curled into a soft smile as the dots popped back up on your screen.

When might I be able to see you again? You hummed at your phone screen, thinking over what to say as the automated voice on the bus informed you that your stop was close.

I work on Tuesday next week! you offered, stuffing your phone into your pocket and hopping off the bus. As you shoved your apartment key into the lock, your cell buzzed with another reply from Harry.

I was thinking about a time where neither of us are working, but you're adorably funny. He sure was a charmer.

He ended up inviting you out to a night in the city. The party scene wasn't terribly unfamiliar for you (your college friends had always been down to get lit), but it was always at frat houses or people's apartments and not clubs that served Dom Perignon under thousand-dollar chandeliers.

The night he took you out, you'd chosen to wear a loose silver mini dress that gleamed and reflected lights around you. It was simple but flashy, something you thought Harry would appreciate. A huge part of you wanted to stop the dressy part of your outfit right there given how often you work on your feet, but you had this pair of black strap heels that had never left your closet and deserved a night out just like you did.

Something inside you expected Harry to have a driver or whatnot, but he actually pulled up in a black Cadillac, and even went up to knock on your apartment door. A true gentleman. Opened the car for you and everything.

"I was a little nervous about riding together," you admitted once the two of you were on the road together.

Harry made a noise of confusion. "How come?"

"You know when you're on a first date, and in the car or the Uber or whatever, there's that small talk before the small talk you have at the destination? Ugh, that's my kryptonite in terms of second hand embarrassment."

"The first time we met, we immediately started talking about the dentist and alcohol poisoning and going to Egypt. I think we'll be fine."

"We did not talk about going to Egy—!" you started, but he cut you off.

"Anyways, I wanted to thank you for coming out tonight with me," he announced.

You exhaled sharply through your nose. "You? Thanking me? How come?" you asked.

"Well... you met me so recently. We've had maybe three conversations. For all you know, I could be a psycho murderer."

"So could I."

He didn't see that coming. He couldn't stop a half-snort, half-giggle from escaping him. "I s'pose, but isn't it more likely to be me?"

"I think that's sexist. We should hold both genders accountable for their shortcomings."

"You consider being a psycho murderer a shortcoming?"

"Exaggerations can go both ways."

He sighed. "I'm just tryin' to say thank you. Most girls wouldn't go off with a strange man." When he realized exactly what he'd just said, he immediately tried to backtrack. "Well, I— Not that I'm constantly asking strange women to go off with me. Just a figure of speech."

It was your turn to snort at his goofiness. "Now I don't believe that for a minute. A man as attractive and charming as you should never be looking far to get his rocks off."

His eyes narrowed but his focus was on the road. "Who are you?"

"I'm Y/N," you declared simply, leaning your elbow against the car door and resting your temple on your palm. "I'm from the suburbs around here. Went to the same college as my parents. Took the same major as my mom. Put myself through school by working at an upscale bar where I meet lovely characters like yourself." You looked over to see how he was reacting to your light teasing and he was staring straight ahead, smirking.

"So you're in school?" He pulled up to a red light and looked over at you.

"I'm a senior." His head cocked confusedly and you sighed. "I'm in my last year. I graduate next semester."

"Congratulations, love." Green light. "Always wish I'd gone to school, jus' a little bit of me does."

"Hmm? Why didn't you?" you asked absentmindedly, picking at one of the crystals on your dress.

Harry actually laughed. "I was, uh, a bit busy during that time of my life."

Your head snapped up and you opened your mouth awkwardly. "Oh!" You felt so stupid. He just seemed so normal to talk to, it was easy to forget who he was and just connect with him.

"S'not stupid, it's actually quite refreshing to feel like a normal nobody sometimes," he said.

Ah, you'd just said all that out loud. "Sorry," you mumbled sheepishly. "And thanks for calling me a nobody."

The two of you had arrived at the venue. "That's not what I meant, love," he tried to get out before a valet boy in a red vest opened your car door for you.

The second your heel made contact with the pavement you were suddenly stunned by a great flash of white-- someone had just taken your picture. You blinked a couple times for your eyes to refocus, but another flash went off, then another and another. You were really close to stumbling back if someone hadn't grabbed your wrist and tugged you towards the inside of the bar.

It was Harry. Once the two of you were inside he immediately showered you in apologies. "'M so sorry, love," he said in your ear. "Didn't think that one through. We'll go in through the back next time. Hope you're okay with being on DailyMail."

Whoa whoa whoa. Next time? Through the back? DailyMail?? It was amazing how nonchalant Harry was about having paps up his ass all the time. Being famous honestly didn't seem to be all it was cracked up to be.

The bar was designed like a speakeasy. It paid homage to the Mafia days of the establishment and the lighting was low and sensual. Harry got the two of you a table and ordered some cocktails.

"How're yeh doing?" he purred, asking you once you'd settled in and gotten your beverages.

You smiled, gently gnawing on the lime twist from your Cosmo. "This is lovely, especially when I'm not the one making the drinks."

He laughed, stretching an arm behind him and shrugging off his coat, leaving him in a simple white button down that was probably not as buttoned as it was meant to be. "I'm gonna scan the room and see if I know anyone here. I'd love for yeh to get to know some new people."

After looking around a bit, he found a friend of his named Nick, a charming and tall man who had a personal space issue (not giving people any of it, that is). He let you and Harry join him and his crew, and everyone was having a lovely time together, sipping cocktails and enjoying the live music performed by a talented woman in a red dress.

That is, of course, until your hand slipped while holding an orange drink and managed to spill it on Harry's white shirt. You rushed out a hundred apologies before he could even compute what was happening but he fortunately had a good spirit about it.

"It's alright love!" he laughed, inspecting the spot. It wasn't ruined. "It's just a shirt. 'Ve got a hundred more at home. I'll go clean this up."

"I'll help you," you offered, still feeling bad. He nodded and the two of you went to the bathroom of the club, a wheelchair-accessible room really only meant for one person.

It wasn't a tight fit, though, and the two of you could comfortably move around in the space. Harry locked the door behind you two and tossed his coat onto the counter while you dabbed at the orange stain with a wet paper towel. It was already starting to lift a bit and looked like the fabric might even be salvaged.

"See? All worked up for nothing." He gave a soft, reassuring smile and your stomach turned giddily. "It especially won't be a problem if I just keep m'jacket on all night."

Harry readjusted his coat, shaking out the lapels. As he carried out this motion, something flew out of the inside pocket that caught your eye. It was small and lightweight, but plopped down onto the floor purposefully. It was a tiny plastic bag, not even as big as the palm of your hand, and filled with a fine white powder.

The awkward silence that filled the bathroom was oxygen-depriving. His mouth opened to say something but he blanked. Even though the music from the club was floating in the air, neither of you two were quite listening to it anymore. Harry's gaze switched from you to the bag at least twice while trying to think of something to say, but you beat him to it.

"Is... is that—?" you started, staring down at the baggie.

"I... understand if this is a deal breaker," Harry explained, picking up the drugs and placing them back in his coat. His hands flew up to nervously toy with his hair.

"I want to try it," you whispered.

"Smoking backstage joints with Kacey was one thing but it's--" he stopped. "I— You— what?"

"I always have," you confirmed, eyes fixated on the pocket where he'd just stuffed the blow. You glanced back up to make eye contact. "You don't have to give it for free. I can—"

"God, no," he said. "You're not gonna take your clothes off just for some coke."

"Uh, I was going to say I'd pay you for it, but real smooth, Casanova," you snickered, making him roll his eyes.

"I wouldn't make yeh pay for it. I mean, this is a date isn't it?" he reminded.

Your shoulders tensed up at the idea of mooching off the Harry Styles for coke, but relaxed when you realized he seemed genuine. "I suppose." You paused for a minute, thinking about what to say next. "My roommate in the second year of college took home the ugliest guys just to rail a line of theirs, so it's probably pretty damn good."

He laughed, lowering his eyes comfortably. "You're not gonna do a whole line first," he said lowly. "Maybe jus' a key bump to see how you feel. D'y'know what that is?"

You smirked. "Yes. You scoop a little bit on a key and just snort that."

"Look at you," he purred proudly. "Are you okay with doing that, doll?"

You leaned your head on the wall. "Yes, sir."

Harry beamed at you and dug into his pocket. "Fuck," he groaned, "the valet boy has m'keys. Have you got yours?"

You nodded and dug into your purse for your keys. He giggled at your keychain that looked like a waffle. "Don't laugh! It's easy to find when I'm in a rush."

"I'm not judging!" he defended, isolating the key with the widest tip. "S'actually quite cute." While holding that one key between his fingers, he opened the baggie and gently squished it around. He then carefully dug out a little scoop of the soft white powder using the key. "I'm gonna do one first so you can see how it's done, then you can try one y'self, okay?"

You nodded, and he handed you the baggie to hold as he carefully kept the key steady. You watched as he meticulously brought it up to one of his nostrils, holding the other one shut with his free hand. He sniffed deeply, and once he'd cleared the key, he pulled it away and let go of his nostril to full inhale. Finally he sighed and shook his head, blinking quickly.

"Harry?"

He fluttered his eyes once more before smiling. "Wow. Never gets old." You laughed with him and he delicately took the bag back from you. "Are yeh ready?"

"Yes," you whispered. He scooped another bump out, this time a bit more erratic and unsteady. He handed you the keys and resealed the bag, slipping it into his coat pocket.

"All yours, pretty girl."

You pursed your lips for a moment and plugged one of your nostrils. You thought your hands would be shaking at this point but you were steady as a surgeon when you brought it to your face. It'd be like taking a pill, right? Like, if you failed to swallow the entire mouthful of medication and water in one go, it won't go down, so if you just did one tiny sniff you would probably choke or cough your guts out. You inhaled deeply, ensuring you got every fleck of coke off the cool metal.

Even after you'd pulled the keys away and let go of your other nostril, you were frozen standing still. Harry observed you and laughed out loud. "Y/N, exhale!"

You finally let go of the huge breath you'd just taken. Your face immediately began feeling a bit tingly and then went numb. Your brain felt like it went into hyperdrive, your skin was on fire, your heart was racing, and something deep inside you told you to run.

"How do you feel, baby?" Harry asked, and you realized his large hand was cupping your cheek.

"So fucking good," you breathed. Your eyes scanned over his face. He had shaved for the evening, since there was no stubble and he'd been a bit scruffy that night at the bar. His lips were wet and red, and his jaw was sharp as steel. This was the first time you'd really gotten a good look at his eyes and they were gorgeous. Pupils blown out by the coke, green from what you could see, littered with flecks of gold. You wanted to get lost in those eyes.

"Y/N?" he asked softly, feeling uncomfortable with you scrutinizing his face. "Are yeh sure you feel al—hmm!"

He was cut off by you diving forward to kiss him. Neither of you had even a second thought about this. Your hands were furious; both of you were pulling at buttons and zippers to expose more skin without even breaking for air. One of your hands strategically slipped down to slide over the bulge in his trousers and he gasped into the kiss.

"Can I—" he breathed over your face.

"Yes, God, yes." At the confirmation, Harry pulled you off of him completely and turned you around to face the mirror, pushing you down by your back. He pinned you between himself and the bathroom counter, your hips digging into the edge. His cock aligned with your center, grinding and shamelessly moaning before tugging up the bottom of your dress and sliding your panties to the side.

His fingers skimmed over your folds, getting to know your core and swirling around your clit. "Hmm, seems like someone gets excited when they've got a li'l blow in them," he mused. "Fuck, pet, your clit is so swollen, someday I'm gonna have to get it on my tongue."

You whined, wanting that to happen right now but were delighted nonetheless to hear his pants unzipping.

"But right now, I have to get m'self in you." You felt him fumbling around behind you before he was pressing against your entrance. "S'this okay, doll?"

You nodded desperately, dropping your head and pushing back so that the head of his cock pushed its way inside you. He groaned and grabbed your hair, pulling you up to look at yourself in the mirror. Harry guided his hips forward until finally the two of you were fit snugly and started fucking in and out of you.

If your lipstick wasn't fucked up already from the drinking and making out, it was now that he was dipping his fingers into your mouth and using the leverage to thrust into you harder. His hands smeared across your face a bit as he relentlessly buried his cock in you over and over.

At one point, you lifted one leg such that you could bring it up onto the counter beside you. From a third eye, the position may seem acrobatic and intense but was oddly uncomplicated and gave Harry a far wider range of motion. At this angle, he was unforgivingly stimulating your G-spot, turning you into a weeping puddle of whines and expletives.

"Right there harder holy fuck Harry you're so deep keep going right fucking there," were only a sample of the pathetic things falling from your lips. You could be embarrassed at your words later, right now you were way too close to an orgasm to care.

Harry was spurred on by your vocalization, as one does. One hand dug into the flesh at your hip to make the two of you collide even more intensely, while the other hand snaked down to flick at your clit with the fingers coated in your spit. When you finally did cum, you were glad that he was pinning you down so tightly as your standing leg was virtually boneless.

As if watching you fall apart on his cock wasn't enough, you had to cap it off by begging the dirtiest things you could think of from him. "Cum inside me, daddy, please fill me up, show everyone who's cunt this is, please."

His hips stuttered once before he shoved the entire length back in you and came until his member stopped twitching. When he caught his breath, he pulled out and watched the soft white liquid seep out after him. He went to touch it and you recoiled.

"Sorry, m'sensitive," you weeped, and he ran his other hand through your hair while putting himself away.

"I should be sorry. Fucked the stand out of ya," he noted with a chuckle, assisting you getting redressed.

Once the two of you were presentable enough to step back out into the club and the thick sex atmosphere had wafted away, the tension grew. "So, uh, it's getting kind of late, hmm?" you led. "Maybe I should be on my way." Part of you didn't want to leave, but all good things had to come to an end and it was better to err on the safe side rather than overstay your welcome.

He laughed, pulling you to him by your waist. His eyes scanned over you and the smirk on his face was downright devilish. "Oh darling, if you think for even a moment that this evening is over, you're quite mistaken."

Harry grabbed your hand and pulled you back into the noisy crowd of the club, where your night was just starting to begin.

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