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“Auto-Pilot” - h.s. one shot

My friend got engaged to her pilot boyfriend and they’re so happy and he was so cute about it and made the announcement over the intercom as they flew to Bali and they’re so rich ugh and perfect and I don’t know I just had this idea and wanted to continue the trend of Y/N being a successful, confident, and amazing woman and yeah hope you all enjoy yay!

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Harry had never been one to indulge in his riches. Sure, he found comfort in thousand dollar button-ups and Gucci shoes, but if it wasn’t for his rockstar appearance one would hardly find him spending any extra money on the lavish lifestyle he could easily lead.

And getting a private jet hadn’t even been his idea to begin with. He’d flown on commercial airlines quite often and was used to sitting on a long plane ride for ample amount of time amongst strangers secretly ogling him. But it was the idea of having his own pilot that finally put the last nail in the coffin on his private jet plans.

You’d first met at a cocktail party in Monte Carlo during the great rally race. Harry felt impeccably snobbish with his champagne and sunglasses and barely-buttoned white sheer shirt, but he figured if he just didn’t talk to anyone, drank his drink, and fiddling with the rings on his fingers then maybe, just maybe, he could get out of his dreadful display of wealth without coming off as too much of a snob. This wasn’t his scene - fast cars made him nervous unlike most other Fast & Furious fans he seemed to be rubbing elbows with - but his manager had said it would be fun, and Gemma had expressed interest so he brought Gemma, for her birthday, even though Harry knew he’d damn well still be getting her some gift months later.

The villa the party was being held at was quite large and all seemed to be made of glass, and so as he walked around the balconies, he finally was able to find some sense of relief from the large crowds as he turned into what seemed to be a sort of library/study.

Finally, he thought, he was alone. Harry leaned against the door and let out a long breath, chugging the rest of his drink before setting the empty flute down on one of the bookcases.

“I would take your drink from the mahogany if I were you. Might leave a mark,” a sweet voice rang out, and Harry nearly died on the spot. You were sitting at the large desk, feet up on it as you leaned back in the chair with a rather large book on your lap.

“Oh m’sorry,” you chuckled, standing as you noticed Harry clutching his chest. “Didn’t mean t’scare ya.”

“Jesus,” Harry grumbled, his heart still beating wildly as he stood up and cleared his throat, “Didn’t see ya there.”

“M’sorry,” you apologized again and chuckled slightly. “Just didn’t want you getting in trouble s’all.”

You were dressed smartly as you gave Harry a kind smile and placed the book you’d been reading back on the shelf.

Harry found comfort in your similar accent, noting you had to be from somewhere near where he called home, and nodded towards the book.

“Please don't stop on my account,” he said, “Sorry for interrupting.”

“Oh no,” you shook your head, “It’s no worry at all. Just as I’m sure you aren’t supposed to be in here, I most definitely am not.”

Harry chuckled, “Considering how comfy you looked at that desk just a moment ago, I’m surprised you don’t run the place.”

You couldn’t help but laugh too, an angelic noise leaving your lips as your smile nearly blinded Harry from the ease and beauty it possessed. “I sometimes like to pretend I am,” you shrugged, “It makes for a much more interesting day, don't you think?”

Harry couldn’t think of a good answer or response to you. Mostly, he was just shocked that you were here considering he’d never seen anyone so effortlessly beautiful and confident in his life. Happiness and warmth seemed to emanate from your presence and put Harry quickly at ease where his heart had been racing faster than the rally cars outside only moments ago.

“M’Arry,” Harry offered his hand and you took it gracefully, stepping forward as you shook his with a smile still on your face.

“Y/N,” you informed him, “Are you enjoying the race?”

“Not quite my gig.”

“Mine neither,” you sighed, “But I go wherever Jack goes, so here I am.”

“Jack?” Harry asked, thinking to your mutual friend out popping champagne bottles on the balcony surrounded by multiple women. “You’re here with Jack?”

“Surprised?” you laughed.

“Quite,” Harry raised an eyebrow, “I’ve never known a friend of Jack’s to be so ... quiet.”

You merely smiled politely at this as you folded your hands in front of you, “Oh I’m not really a friend of his,” you shrugged, “I’m his pilot.”

This took Harry a moment to process. Jack’s pilot? As in, you fly planes? You obviously picked up on his look in confusion as you cleared your throat and said, “I’m a private jet pilot, and Jack usually hires me for his services and events.”

“Wow,” Harry now raised both eyebrows, “That’s spectacular.”

“Quite,” you now said, echoing Harry’s previous statement. “Would you like to go get some more champagne? I hear there might also be sushi.”

You and Harry spent the rest of the day out in the sun next to the pool as you told him about how you’d become a pilot. Your grandfather had been a pilot in the Second World War, and your father had been in the RAF for quite some time before retiring. With no brothers and two younger sisters obsessed with many other things, it seemed only natural that your grandfather and father would take you out flying. And good for you and them, you’d fallen in love with it.

Commercial flying hadn’t been for you, because you’re more of an easy-going spontaneous free-bird. And so private jets it was, and private clients it became. Harry soaked up absolutely everything you said, and your eyes lit up when Harry talked about the spitfires they’d used on the set of Dunkirk. You had so many questions - intellectually impressive questions - and Harry blushed to think he would never be able to answer them.

As evening came around, you sighed as you checked your watch. “I must be off. Got to get through some check-ins and prep for tomorrow. But I’ll tell you what, Harry, should we ever meet again or you need a ride anywhere, I’d be happy to be of service. First flight’s on me, yeah?” you winked as you handed him your card and stood. He scrambled to follow suit as he offered his hand but you gave him another world-class smile and pulled him in for a hug.

“T’was lovely meeting you, Harry. You’ve defied all expectations and made my day quite less boring than it usually is.”

“Likewise,” Harry smiled, “And I will definitely be taking you up on that offer.”

“I look forward to it.”

And from there, you and Harry started to work together. Harry had never really liked traveling, but when he showed up at the hanger and saw you standing outside the door smiling at him, it made everything so much better. At first it had just been flights here and there while you continued to work with other clients. But as the months dragged on and Harry realized he selfishly didn’t want to share you, Harry took you on as his private pilot for his tour and personal life.

And this came at a perfect time for you considering the amount of jackasses you’d had to fly that you were getting quite tired of. You loved working for Harry. He was sweet, paid well, respectful, and you never felt you were flying anywhere that would drag on. Harry and everyone he surrounded himself with were a joy to be around, and you found yourself enjoying each flight more and more. After asking sheepishly a couple of times prior, Harry finally would start to hang out in the cockpit with you from time to time, just standing in the doorway of the one-pilot jet crunching on crisps or apples as you flew, laughed, and chatted with one another. Though you were his pilot and he was your boss, you also became friends.

And God, Harry loved it. He loved the idea of spending countless hours with you and knowing that you were being cared for while also doing what you loved. He loved your style, how confident you were, and how you held yourself and you business to such high esteem. You were always punctual, honest, and you never seemed to be in any mood other than calmly content. All Harry’s friends came to adore you, and whenever Harry would offer a trip to someone, they would always ask if you would be taking them.

With Harry’s tour starting, Harry found himself in the jet more often than before, but you had no complaints and did nothing but encourage him and pamper him every time he stepped on board.

Harry watched as you jogged up the steps after making sure all his luggage was taken care of. He’d watched from the window as you gave Greg, his bodyguard, a hug and Greg offered you a plate of cookies his wife had made. Your smile shone as you thanked him, giving him a loving pat on the arm before jogging up the steps and wiggling your eyebrows over the plate of cookies.

“Would you like any?” you asked, “I’m not really a chocolate fan, I must admit.”

You looked particularly cute today, and Harry appreciated that you weren’t in normal pilot attire (even though he’d definitely had tens too many dreams about you in a sexy pilot costume that he would inevitably rip off at some point). He felt his cheeks warming just at the thought and slight humiliation of what was going through his mind as he sat up and cleared his throat.

“I will never understand how you don’t love chocolate like the rest of the human race,” he sighed, taking a cookie off the plate before you set them on the table before him.

“Well, when your grandmum owns a chocolate shop and you sneak one to many sweets as a wee-one, you lose your interest when it’s handed to you easily,” you sighed, brushing the crumbs off your hands as you patted down your skirt.

“Then it’s the thrill that gets you to like something?” Harry asked, smiling up at you and you couldn’t help but wonder how he could be so adorable.

“It’s the chase for sure,” you nodded, sending him a wink, “Makes everything more fun and adventurous, don’t you think? With my sweets, my career, my men. It’s always about the chase.”

This nearly made Harry choke on his cookie as he thought of the idea of you having men chase after you. “And who would be the one chasing? You, or your men?”

“Definitely the men,” you laughed, “Alright love, now buckle up. I want to get you to England in one piece and you know the drill.”

Harry’s shaking hands fumbled with the buckle at the idea of men chasing after you as he watched you walk towards the cockpit and close the door behind you. Not moments later, your voice was coming over the intercom. “Cross-checked and ready for departure, Mr. Styles.”

Harry pressed his intercom button, “Thank you Captain. Safe travels.”

“You as well dear,” you said with a chuckle that eased Harry immediately. The flight was quicker than Harry had anticipated, probably because the soft tunes of Fleetwood Mac throughout the jet eased him to sleep for most of the journey, and you were waking him up gently not a moment later.

“We’ve arrived,” you smiled, “Sleep well? You don’t usually sleep the whole flight.” You perched yourself on the edge of the seat before Harry as he slowly shifted to sitting up straight in his seat while rubbing his eyes. His face was puffy from sleep, lips pouted, and hair a mess as he stretched. Seeing you sitting there made him watch to reach out and pull you onto his lap and cuddle you until he was fully awake, but he also wanted you to keep your job and he figured making you uncomfortable due to his own personal feelings was unwarranted and you would fly off without him in an instant.

“Just tired I guess,” Harry yawned, “Been a lot with all this traveling and the shows. Can’t imagine what it’s like to have to fly everywhere and not be able to sleep. You deserve a raise, love.”

Your cheeks warmed and Harry’s heart hammered as he smiled at the thought of making them pink. You smoothed down your dress again and sighed, “I do worry ‘bout ya from time to time,” you sighed and reached out to flatten his hair to the best of your ability. “You do work hard.”

“M’not the only one,” Harry sighed, “You’ll rest during the shows, yeah?”

You shrugged, picking at your nails as you stood and walked over to the door. “‘M sure the family will find something interesting for me to do on the farm,” you smiled, “Now get out there rockstar, you’ve got shows to perform.”

Harry wasn’t sure where the kiss on the cheek he gave you came from as he made his way off. It just seemed so natural to reach up and cup your face, kissing you cheek quickly and amicably before jogging down the steps of the flight. But he could feel you tense the moment his lips met your soft skin, and instantly Harry knew he’d crossed some type of boundary.

You two were friends and you were close, but maybe you weren’t that close yet.

“Um,” Harry cleared his throat as he got his bags, “Thank you again, Y/N. I hope you have a lovely visit with your family.”

“Of course,” you nodded, “And thank you too, H. Best of luck.”

Harry would be touring (on a bus ugh gross why, he thought) for two weeks now in England, and in that amount of time you’d be going home to visit your family for a bit and take a much needed break. Though Harry would miss you, he was glad you were getting some time off.

And lovely was the time off indeed. You stayed with your family for a week and a half, enjoying their company, helping out on your family farm, and attending some school functions for your younger sisters. Your family was full of questions, but they were also full of patience, and you appreciated that as you spent some time getting some much deserved rest. By the time you arrived back in London for Harry’s final shows, you were well-rested.

Harry, on the other hand, was a mess.

He was tired. He was irritable. He loved being on stage but the moment would get off the tiredness would hit him and he’d slump into a couch to almost instantly be asleep. He had one more show before he was done and the entire tour would be over, and Harry felt guilty for looking forward to it. He loved the attention, the limelight, the crowds chanting his name and his lyrics. He loved every bit of it - he was a self-pronounced narcissist and he was okay with it - but after months on end of the same head pounding when he wakes up in the morning, he could use a break.

You could see he was a bit more tired than usual when you stopped by to approve travel plans the day of the final show. Harry was in makeup, which you secretly found hysterical, and only half his face was done when he saw you with your iPad and eyebrows raised, iPad clutched to your chest. You were dressed for the chilly autumn air and still looked professional as ever.

Harry wondered what you would look like with casual clothes on, or just woken up. In fact, he wondered that quite often (enough to know he probably shouldn’t) and the idea of it all kept creeping back into his mind. Did he really have a crush on his pilot?

Shaking these thoughts from his mind, he sat up a bit more in his seat and gestured you over.

“Miss Y/LN, I promise you this isn’t a normal thing,” he grumbled, shifting slightly in his seat and giving the makeup artist a look to signify that they would start again once he was finished with you. You gave him a soft smile, offering him the iPad with the flight itineraries as he sighed and rubbed his eye - the non-makeuped eye - and blinked a few times.

“Yeah looks good,” he nodded. It was so interesting to you how half his face looked lively and young, while the other seemed sunken in and withered. He looked tired, and not the kind of tired that he was when he was asleep on the plane, but more just bone-tired and exhausted. You almost wanted to reach out and give him a hug, but you figured that wasn’t the most professional way to go.

“Final show tonight then?” you asked as you took the iPad back once Harry had signed it. He nodded and sat back in the chair, head resting on the top as he closed his eyes.

“Yeah. Just gotta survive tea with my mum first and then the show and I’m home free,” he nodded, crossing his arms over his chest as he let out a loud yawn.

“You’re putting on makeup to meet with your mum?” you asked before realizing you were probably stepping over some sort of boundary. Harry opened one eye to look at you as his makeup artist continued to get to work on the other side of his face.

“Well, Anne’ll probably ‘ave a fit if she sees me the way ‘am right now,” he sighed as the makeup artist tilted his head up to get along his neck. “Figured I might as well ‘ave it taken care of now.”

You chuckled and clutched the iPad to your chest. “In that case then I wish you all the best,” you nodded before taking a step back, “I’ll ‘ave the plane prepped ‘nd ready for you tonight.”

“Thank you Y/N,” Harry nodded, “Really. And if ya see my mum on the way out, could you just stall ‘er a bit?”

“You want me to stall your mum?”

Harry hesitated, “S’not quite your job, innit?”

The worst part was that Harry couldn’t even tell if you were uncomfortable or not. You always seemed to at ease with everything you were doing and so confident in the way you held yourself. He was stepping over boundaries, this whole conversation was, and he knew that it wasn’t right. You were just his pilot, no matter what feelings he was feeling for you, and any conversations you had while he was on your plane were all in good fun. Yes, you were friends - it’s always good to be good friends with your employees - but there was something professional and sophisticated about it all that even seeing you in a place that wasn’t the plane even was throwing him for a bit of a loop.

“Don’t worry, Harry, I’ll take care of it,” you sent him another one of your smiles, the ones that shone like sunshine and sang like a canary. He watched you walk out of the room, your dress swishing a bit as your heels calmly made their way across the floor and Harry felt the need to rub his face but stopped when he realized he was still three layers away from being finished.

It was twenty minutes later before he was grabbing his phone and walking out of the room. It was the laughter that he heard first before he turned the corner. It was your laughter, sweet like nectar and airy like wind chimes that raised goosebumps all over his body. And then when it was mixed with his mum’s, well, that just made him freak out a bit.

“Mum,” he cleared his throat, “Sorry ‘bout makin’ ya wait.”

“Oh love it’s no worry!” Anne smiled as she stood and gave Harry a gripping hug. “Y/N was telling me your meeting was running late. Always happy to be accompanied by such lovely people.”

Anne stepped aside and Harry gave you a small, slightly embarrassed and guilty smile. But you did nothing but smile back brightly, giving him a bit of a wink that nearly almost had him falling at your feet.

“You didn’t tell me your pilot was such a wonderful person!” Anne chastised her son, “I wish to have met Y/N earlier! You need to tell me these things more, H!”

“M’sorry Mum!” Harry chuckled and slung his arm around his mum’s shoulders, “Y/N’s a great pilot. She makes sure I get wherever I need to go safely, and makes sure I’m nothing but happy too. That doesn’t hurt much.”

“Well of course not,” Anne rolled her eyes, “You know, Y/N, we’re just about to head off for some tea. Would you care to join us?”

Harry knew he must have looked like The Scream painting right in that moment and was afraid he was going to sweat off all the damn makeup. Mums are great and all, but they also have a canny knack for ruining things through literally nothing but their naive kindness. Harry’s eyes widened, his mouth parted to reply and make up some stammering excuse, but Y/N beat him to it in a graceful and loving way.

“I would love to join,” you nodded, gracing Anne with the most kind of smiles that left your eyes scrunching with sincerity. Anne smiled triumphantly before making her way off to the car as Harry fell back with Y/N.

“You don’t have to do this,” he whispered, “She’s cute, but you don’t have to say yes to everything she asks.”

“Oh but you should,” you chastised him. “She’s such a lovely woman. She’s lonely, Harry, can’t you see? You should visit home more. It’s not every day you get to spend time just sitting back and drinking tea with your mum, and you should take advantage of every opportunity you get.”

Harry was struck by these words, mostly because he was used to getting advice from Y/N, but never like this. Y/N noticed far more than Harry had imagined. He knew she was sharp as a whip, but she seemed receptive to absolutely everything and everyone around her. He was immensely impressed, but the warmth in his heart quickly started to turn into a burning inferno as he wondered, had she noticed his budding feelings for her?

The panic chilled in Harry’s chest as they drove to the tea shop not far from the venue. Anne and Y/N talked the whole way about Y/N’s childhood and where she’d been raised. You talked about your farm, and the first horse you’d ever tamed, and you mentioned how being a pilot was kind of in your blood.

“Her dad flew for the RAF,” Harry input as he awaited his tea. You being with his mum wasn’t as painful or awkward as he’d figured, but he did feel as though he was invisible. His mum loved meeting new people, but sometimes he got a bit jealous after she didn’t pay enough attention to him.

“Oh that’s exciting!” Anne smiled, “And your granddad as well?”

“Yes in the Second World War,” you nodded and lifted your cup to your lips.

“I told her I’d take her to the Dunkirk hangers at some point before they’re taken down. Ya know, those promo ones they got?” Harry asked, smiling at you as you gave him a nod of encouragement back.

“That would be lovely!” Anne smiled. She reached for a tray of small sweets before offering them to you.

“Oh no thank you,” you smiled, “M’not a big chocolate fan, I must admit.”

“Yeah,” Harry snorted, “S’why m’defiintely convinced she’s an alien.”

You couldn’t help but laugh, “Oh come of it!” you threw your head back, “And you still get on my plane knowing I could very well be from Mars.”

“Fly me back ta your planet?” Harry shrugged, “T’would make great in the papers, love. ‘First Rockstar to Mars, Mr. Harry Styles’ plastered all over.”

“Usin’ me for the papers,” you tsked, “Thought you knew better.”

“I bet your flights are quite fun,” Anne mused, looking between the two of you.

“He bothers me in the pit quite often,” you nodded, “Stands back there in the doorway munchin’ on his crisps and ‘v got ta clean up after him like a child.”

“Hey,” Harry pouted, fumbling with his bottom lip as he smiled at you and you smiled back. Any awkwardness between the two of you had fizzled out at this point. Remnants of the kiss on the cheek he’d given you earlier seemed to have diminished and whatever boundaries Harry had been nervous about had dissipated. Hell, his arm was even on the back of your chair and you weren’t leaning away.

“Well this was such fun,” Anne smiled, “Y/N dear, please if you’re ever in the area do stop by. And Harry,” she glared at her son, “Introduce me to more nice people from time to time, will ya love?”

“Oi Mum!” Harry cried, “Y/N’s just special, yeah?”

He saw your cheeks flare a bit from this and he cleared his throat, riding his cup of the rest of his tea before standing. “‘v got ta get back,” he mumbled, “Everything’s set up at the show for ya Mum.”

“And Y/N, will you be going?” Anne asked.

“Oh! Um ...” Your mouth formed a cute and small ‘o’ as you looked up to Harry as if for confirmation. You’d never been to one of his shows. You’d hear him sing often on the plane, and you’d listened to his album multiple times. But you’d always been busy during his shows with prepping for the concert. But this time you weren't leaving until two hours after the show. Maybe you could make it?

“If you’re not busy,” Harry started, feeling his chest beating rapidly, “I’d love ta ‘ave ya there?”

You look down at your watch as you walked out of the shop and Harry awaited your response for what seemed like ages. “I’d love to go, H,” you smiled, “Let me just make sure everything is prepped and ready to go before, yeah?”

“‘Course,” Harry nodded, hands clasped behind his back as he leaned forward a bit and rocked on his feet. “Yeah whatever works.”

“Thank you,” you nodded as Anne went over to get the car. “It was nice bein’ around a mum for a change.”

Harry knit his eyebrows together in confusion, “Thought you’d just spent the whole week with your family?”

“Oh yeah,” you smiled at him as the two of you stood a bit closer than necessary to keep out of the wind. “But my mum passed on when I was about 12 or so,” you shrugged.

Harry felt his heart pounding as he didn’t think before reaching out and giving you a hug. You couldn’t help but laugh at Harry’s pouting face and his strong arms wrapped around you as you softly hugged him back. “It’s okay, Harry. It happened ages ago. M’all better now.”

Harry pulled away and cleared his throat, adjusting his sweater as he nodded. “Oh shit. I um ...” Harry gestured to your shoulder where he’d rested his cheek and a patch of makeup seemed to have rubbed off. This made you laugh even harder as you brushed it off a bit and cradled his cheek in your hand.

“You’re something else Harry Styles,” you laughed before an alarm went off on your phone and Harry sucked in a breath as you pulled your hand from his skin to check it. “Alright,” you informed him, “I’m gonna go get things ready and then maybe see you at your show. Exciting, innit?”

“Very,” Harry nodded, reaching down for a hug again and trying his luck with a kiss on your cheek once more. You didn’t shy away as he stepped back and gave you a bit of a nod, “See ya later then.”

You gave him a smile before ducking into the cab you’d called down and making your way back to the airport. Harry seemed to wait on pins and needles to know whether or not you’d be coming to the show. You didn’t text him, or call, or even send any sort of confirmation to anyone about whether or not you’d be there. Everyone figured Harry was only slightly more nervous for his final show, but in reality he was just nervous to perform in front of you.

Why should he be though? You were nothing but sweet and supportive. You wouldn’t turn him away if you didn’t like his performance. You’d said you enjoyed his music and you always cheered him on and laughed whenever he sang on the jet, but now things could be different and Harry wasn’t sure how he felt about that.

But he put those feelings aside for the show. He knew he had a job to do and he didn’t want the emotional roller coaster going on in his heart to ruin an experience for all the fans who had come to see him. That wasn’t right. And besides, when he turned and looked to his mum he felt like he was suddenly flatlining, because there you were sitting beside her smiling and clapping along with her. Dancing around a bit as his mum laughed.

You were here and you were gorgeous. Your eyes caught as he adjusted his ear piece and looked up at you and his mum. You looked over to Anne who was checking something on her phone and Harry knew that you were realizing he was looking and smiling at you. You couldn’t help but wave and give him a thumbs up, and Harry felt his entire body light on fire right in that moment.

The rest of the show seemed to have some sort of energy Harry didn’t even know possible. He felt reenergized after being tired for so long, and even his band could tell that there was something electric about the way Harry was performing. Afterwards was a crowd of hugs, kisses, laughter and tears as the tour was now officially over. Harry enjoyed every moment he spent with the people who had made it possible, but when he caught a glimpse of your shimmery purple, he was quick to turn towards you as you barreled towards him (still completely elegant and graceful, of course, Harry thought).

“Harry!” you cried, jumping up to hug him as Harry held you close and closed his eyes, taking in the feeling of your body locked close against his as he took in your scent. Your feet were off the ground as you laughed and Harry held you close, one hand tangled in your hair and the other around your waist keeping you to him.

Finally he set you down though and you brushed some hair from your face. “Oh Harry that was amazing,” you nodded. Your hands were on his shoulders and they ran down his arms to his forearms as he held your waist and smiled at you as you talked. “You were great! Truly I can’t tell you how much I enjoyed it; I have so many things to say!” Your eyes were bright and your cheeks flushed but Harry couldn’t smell any alcohol on you, and he knew you never drank while working. This was a natural high that he’d created.

He felt proud.

“‘M glad ya liked it!” Harry called over all the noise, “What did ya think of -”

Harry was cut off by your phone going off and you looked down at it, some of the light draining from your eyes as you sighed. “Oh, Harry I’m so sorry I wish I could talk to you more but I have to go prep,” you nodded, “But I’ll see you in two hours! We can talk more then!”

“Okay,” Harry nodded, “‘M keepin’ ya to that!” he called after you as you jogged off, waving over your shoulder as you pushed the door open. Harry turned back to his band as they all enveloped him in cheers and cries to victory that seemed to last the next two hours.

“We’re not finishing this celebration yet!” someone cried as they all packed up their bags. “Drinks on me on the jet!”

“Oh wait no,” Harry turned and gave his band a confused look, “Thought ya had another flight?”

“What? Think you could get rid of us that easily? Your jet’s big enough for all of us. Y/N loves us!”

Harry didn’t know what to say to this. What he really wanted to say was, “You’re not allowed on my jet. Y/N and I were going to hang out and I was going to try and kiss her, you tosser.” But instead he just let it happen as they all drove up to the hanger and Harry noticed you were off to the side going over some last minute paperwork as the band all crowded into the jet. He felt awful.

He watched as you jogged up the steps, eyes still bright as you said, “Okay love, are you - oh!” No one else might have noticed the split-second your face registered a bit of shock before your face turned bright with a smile he knew was still genuine, but maybe not as sincere as others. “Hello everyone,” you smiled, “Good to see you all. Great show tonight!”

“Thank you Y/N!” the whole jet seemed to chorus as Y/N met Harry’s eyes and she gave him a quick wink.

“Well buckle up everyone,” you said, “It’ll be a long flight so make yourselves comfortable!”

Harry waited until not a second after the seatbelt sign was off before scrambling towards the cockpit and knocking three times. “Yes?” you asked from behind the door before Harry opened it, leaning against the doorway and clearing his throat.

“‘M sorry Y/N,” he sighed, “They kinda overpowered me.”

“Oh H, it’s fine!” you turned and smiled at him, a small laugh following. “I know you want to spend your time with your band. You just completed a great tour. You should be immensely proud.”

“Yeah well,” Harry shrugged.

“I know I’m proud of you,” you said earnestly and Harry’s eyes finally came up to meet yours.

“Yeah?” he asked, a smile finally finding it’s way onto his face.

“Oh definitely,” you nodded, “You were so amazing. I knew you were a performer, but that was an experience for sure.”

“Glad you could make it then. I know my mum appreciated it too,” Harry nodded.

“Now as much as I’d love to talk with you, Harry, you look completely beat and I want you to get some sleep.”

“I’ve got plenty of time to sleep now that the tour’s over,” Harry waved that off, “I want to talk with you.” You watched as he sunk down along the wall and sat with his legs stretched out in front of him. He was like a child, an adorable child, and you couldn’t help but smile as you flicked onto auto-pilot and turned to him.

“Alright then,” you sighed, “What’s your favorite song to perform?”

When the flight was over, Harry had to wake everyone up so they could depart. With tired smiles and mumbled, “Thank you”s the band lumbered off the flight, each giving you a hug which you kindly and warmly returned by rubbing their backs and and giving them a good squeeze.

Harry was last off as he watched you look down at your watch and try your best to shake off a yawn. “Let it out,” Harry chuckled and you gave him a look before the yawn took over and you were stretching up, cracking your neck and rubbing your eyes. “There ya go,” he chuckled.

“As unprofessional as that was,” you chuckled tiredly, “I needed that.”

“Well, take some time off, yeah?” Harry suggested, “‘M not plannin’ on travelin’ much soon.”

“Good,” you nodded, “You need a break far more than I do. Please take some time,” you urged, gripping his arms before you stepped back and offered Harry a hug. “Rest well,” you whispered as Harry held you.

Harry closed his eyes once again taking in your scent and feel against him. He let out a long sigh, hunkering down a bit and nuzzling his nose into your neck as you chuckled and pulled away awkwardly at that. You sucked in a big breath which hitched a bit before you gave Harry another smile. “Just let me know whenever you’d like to go anywhere, okay?”

Harry nodded and made his way to his car. You had pulled away from his hug. Was it just because you were tired? Was it because he was getting too close? You went to tea with his mum for Christ’s sake! These thoughts kept Harry awake as he drove home that night and were on his mind as he went to bed. And he meant what he said, that he wasn’t planning on traveling anytime soon. He was looking forward to Netflix and his bed and avocado toast for the next couple of weeks.

That all changed though when he received a call from one of his mates Josh a couple days later. “‘lo mate,” Harry yawned as he stretched in bed and stuffed his face into his pillow.

“Harry! Hey man! Look, some of us were thinking of getting together in NYC to support Amelia’s art show on Friday. Wanna come support?!”

Amelia was a sweet girl. A little fairy of a girl with red hair and freckles that reminded him a bit too much of the orphan Annie with it’s reckless curliness. He was tired, exhausted even, but he needed to be there for his friends, sure.

“Yeah mate just text me the details and I’ll fly out.”

“Sick! See you there man!”

You had her arms crossed and your eyebrows knit together cutely (in Harry’s opinion) when he rolled up at the jet hanger on Friday morning while it was still dark out. He took off his sunglasses as he pinched the bridge of his nose and shouldered his bag.

“What happened to taking a break?” you asked, “It’s been two days.”

“Yeah well a friend has an art show opening tonight,” Harry yawned, “Gotta show my support. She’s a sweet girl.”

You didn’t say anything to this as you started walking up the steps and into the cockpit, not sticking around as Harry situated himself. “You alright love?” Harry called right as Y/N was about to close the door.

“Fine, H,” you turned and gave Harry a smile that would have normally melted his worry and eased him right away. But it didn’t quite reach your eyes and your face wasn’t bright with warmth and love so Harry pouted.

You rolled your eyes and smoothed out your skirt as you stepped back into the cabin and offered Harry a pillow.

“Really, Harry, I’m fine. Get some sleep, okay? I’ll wake you when we’re almost there.”

You didn’t often accompany Harry wherever he went. When you had worked with other clients, you’d always gone to their events to be there right when they were ready to leave, or you’d stayed on the jet at all times. But with Harry things had been a bit easier with him just texting you always at least an hour before he was ready to go. He trusted you to go off and do your own thing while always being able to be back and ready to go whenever he was.

So Harry was a bit surprised when you slide into the car with him as you arrived in New York. “What?” you asked in response to his raised eyebrows. “I hate New York, and I don’t fancy sitting on that jet for much longer so I’ll just hide in the background. Besides, I like art.”

“I know,” Harry nodded, “I’m just surprised you’re not running off to some coffee shop with free wifi.”

“I can’t fit into a fancy art show?” you asked, raising an eyebrow as Harry winced.

“Love, no. That’s not -”

“I’m messing with you, H,” you chuckled and looked down at your phone, “Just let me know when I need to go and get the jet ready for you, okay?”

“You know, I can wait while you do all that at the hanger, right? I don’t mind.”

“Not professional,” you shook your head as you arrived at the building where the rooftop art show was taking place. “Just let me know,” you nodded before sliding out of the car.

Harry should have been paying attention to all his friends. They were the reason he was here obviously. And Amelia was through the roof when she saw Harry. But he couldn’t keep his attention on them when you were standing and talking to someone about a work of art, or when you were sitting at the bar with a flute of champagne, or when you were reading a brochure. You were effortlessly gorgeous and care-free. And he was head over heels for you.

And you were also struggling a bit. You obviously cared so much for Harry, or else you wouldn’t have taken the offer to be his private pilot. But seeing him look so tired and uninterested among his friends, only to smile and laugh with them and act normal when they had their attention on him was concerning to you. He needed a break, but he was too nice to stop his life for a nap. But you weren’t anything more than his pilot - sure, his friend, yeah - but it would be unprofessional to say anything else.

So you kept you mouth closed when Harry slept the entire flight back to LA. You also didn’t say anything when he went to a birthday party in Seattle three days later, or flew to Colorado for a baby shower two days after that. You just let it fester in your chest as you flew, knowing that Harry was being run thin.

Harry noticed you become a bit more distant than usual, and he felt bad that maybe he was overworking you. He offered to hire another pilot for some trips just so you could catch a break, but the amount of force you used to say that no, you were just fine with being his pilot, was quite surprising to him. You shot the idea down so quickly that he nearly blinked before you were slamming the door shut to the cockpit.

Harry’s trip to France though was much more rushed than the previous ones, and Harry noticed by your natural hair and outfit that you hadn’t had as much time to prepare for this one and he felt awful.

He’d gotten the call at around nine in the morning that his friend Scott was going to be previewing his indie film and Harry had promised he’d be there - and he’d forgotten.

As soon as Harry saw you, he started apologizing. “Y/N!” he started, “I’m so sorry! I know that this is super last minute and I totally forgot but it’s been in my calendar and for some reason I thought I’d already told you but -”

“Harry,” you cut him off by holding up your hand and giving him a soft smile, “It’s fine. Strap in, okay? This’ll be a long flight.”

Harry just sat there feeling nothing but guilty as he watched the jet take off out the window. God, he’d really messed up. He’d tried to be nothing but professional and easy for you, and here he was dragging you all across the world with only a few hours notice.

Harry usually played music during his flights over the speakers, or slept, or was doing something, but when you peeked through the crack to check on him, he wasn’t doing anything but staring out the window with his hands clasped in his lap. Sometimes he looked down at his hands, sometimes he rubbed his eyes. But that was about it.

Though you knew this was unprofessional, you couldn’t stomach it any longer and you hit the intercom button.

“This is your Captain speaking. She’s concerned about you and was wondering if she could come back there to chat?”

Harry couldn’t help but smile at this. Whenever it was just him flying, you often had conversations over the intercoms. But it had been a while with the tense nature between the two of you and hearing your voice soothed him instantly.

“Considering it’s only you and me on this private jet, and you’re the pilot, shouldn’t you be occupied flying this machine?” he asked once he’d pressed the button and he swore he could have heard you laugh in the cockpit.

“That’s what auto-pilot is for, love."

“Then by all means come and take a seat,” Harry said, sitting up more and watching as you stepped out of the cockpit and let out a long sigh, giving him a once over before you walked over and sat down opposite him.

“Hello pilot,” Harry gave you a sleepy smile and you reached out to push a curl from his forehead.

“Hello rockstar.”

“Listen, I know this was super last minute and I get that it wasn’t the most professional thing to do, but I promise that it won’t happen again and -”

“Harry, really, I’m not mad about it,” you put your arms up in defense, “I’m just worried ‘bout ya, love.”

Harry felt his face heating up just from the fact that you were worried about him. It felt good to know someone out there was looking out for him, and knowing that it was you, that was even better.

“I have a feeling I’m not the only one on auto-pilot right now,” you bit your lip, “It’s one thing to travel for your job and your work, and I get that sometimes that can become busy and stressful, but you have to put your health first Harry, or else you won’t be able to do that job that you love so much.”

You got up from your seat as Harry rubbed his eyes tiredly and perched yourself on the arm of his large seat. “I know that you’re a sweet and wonderful person and you care so much about others, but I’ve been watching you for almost two weeks now nearly push yourself to exhaustion because you’ve been traveling here and there merely because a friend asks. You can say no, you know.”

Harry groaned and rested his head back as he looked up at you. You usually had your hair up when you worked, but as he looked up at you now, your hair was framing your face and flowing freely down your shoulders. You looked beautiful and concerned, and that made his body buzz.

“I know I shouldn’t be spreading myself so thin,” Harry groaned, “But majority of the year is all about me and all the things I’m doing. It’s about my job and my music and my friends come out to support me. So when I get time off and have the time to spend for others, I just feel obligated to take that.”

You nodded as you listened to Harry speak, and it almost seemed second nature that you reached up and started massaging his scalp. Harry closed his eyes and hummed lowly because of course you would be doing this. Of course you would know exactly what to do in order to calm him down and put him at ease.

“I think the solution to your problem is simple, H,” you whispered, “You can’t be there for your friends and your family if you’re not fully invested. And if you’re not putting your health first, then your mind will be elsewhere and you might even miss more things if your health declines. I want what’s best for you, and I know that I’m probably stepping over so many lines on my contract by coming back here and lecturing you but -”

“No,” Harry shook his head, “No, you’re not. You’re my friend, Y/N, first and foremost. I didn’t hire you because of your impeccable flying and great skills as a pilot, even though those are top notch and you’re basically the Wonder Woman of the skies,” you chuckled at his as Harry looked up and smiled at you, reaching lazily for your hip that was sidling up next to him as you rested on the arm rest. “But I hired you because I knew I could be myself around and trust you and that’s all you’ve ever provided for me, and for that I thank you.”

You were smiling again with that bright and loving smile full of wonder and appreciation that Harry could easily get lost in. Reaching up from his reclined position, Harry cupped your cheek with his larger hand, running his thumb along your cheekbone and watching in awe as your eyes fluttered shut and you leaned into his hand.

“I um ...” you cleared your throat and bit your lip as you pulled away from Harry’s touch. Your hand left his scalp and you stood slowly and gracefully from the seat. “I have to get back to ... the flying thing,” you whispered.

“Yeah,” Harry nodded, “Yeah yeah of course.”

“I’m glad we had this talk,” you said earnestly, “Maybe after this you call it quits on the events for a while? Get some much deserved rest, yeah?”

“Yeah love,” Harry nodded, “That sounds good.”

“Right,” you cleared your throat again and made your way back into the cockpit, closing the door behind you. There was nothing Harry wanted more than to follow you in there and demand you both talk out your feelings. It was becoming more aware to him that maybe he wasn’t the only one harboring the feelings he was, and that maybe they were mutual. But he didn’t want to push his luck, and he knew that coming back here and talking to him was a big step for you and he didn’t want to overdo it or push it in any way.

He fell asleep shortly after that, and when he awoke, you were standing over him again gently shaking his shoulder, your hair falling into your face again and Harry realized he really, really loved you with your hair down.

“Hey,” you whispered softly, “We’re here.”

Harry nodded, stretching up as you pulled out his bag and waited in the hallway for him to disembark as you lowered the door.

“Pleasure flying with you as usual, Mr. Styles,” you nodded, hands clasped in front of you as Harry shouldered his bag and pocketed his phone.

“The pleasure was all mine,” Harry smiled and reached out, tucking a strand of hair behind your ear as he gave you a soft smile. In a moment of confidence, he leaned down and pressed a kiss to your forehead, grasping the back of your head gently before he pulled away. “This shouldn’t take long. I’ll call.”

“Yes thank you,” you mumbled, not meeting his eyes before turning back to the cockpit.

Harry fell asleep during the film. He didn’t mean to, and he knew people noticed, but considering his face was basically consumed by the bags under his eyes, he knew his friends understood. He decided to stay the night and texted you that if you’d like to stay in the same hotel, he’d be happy to buy you a room. You showed up to his hotel not a half hour later, hair lazily placed in two braids and a comfortable dress wrapped around your body.

God, Harry thought, you were so cute and stunning.

Harry was waiting in the lobby and he smiled when he saw you walk through gracefully and with purpose with your small bag being rolled behind you.

“Hey,” he said as he met you and went to take your bag but you gestured that you got it, “I’ve been trying to call you and you haven’t been answering.”

“Sorry,” you sighed, “My phone died and I forgot my charger. Have I kept you waiting long?” you asked, always the polite one.

“No, no that’s not it. You’re just on time,” Harry smiled, “Just that they didn’t have anymore rooms and but they didn’t have any available and so um, well ... yeah.” Harry wasn’t sure why he felt so embarrassed. You were both adults and had been kept to tight confines before quite often. But in that moment he felt like he might die and he was sure the entire lobby could hear his heart beating rapidly.

“Oh that’s fine, Harry, I don’t mind,” you smiled, “Don’t worry about it.” You patted his arm as you walked past him towards the elevator. “What floor?”

The elevator ride was quiet at first before you cleared your throat, “So how was the movie?”

“Couldn’t tell ya. I fell asleep,” Harry chuckled.

“Oh Mr. Styles,” you tsked, “How unprofessional.”

“Yeah well I haven’t been the most professional as of late,” Harry sighed. “Here we are.” He opened the door for you and you placed your bag down on the couch.

“What do you think you’re doing?” Harry asked.

“I’m placing my bag on my bed. I -”

“No you’re not,” Harry shook his head, “Take the bed. What do ya think I am? An animal?”

“Harry,” you put your hands on your hips to protest and start some speech but Harry wasn’t here any of it.

“No way,” he shook his head and took your bag as he carried it easily into the bedroom where the king sized bed awaited you. “You’re sleeping in here. I won’t hear anything else so don’t even try,” he said as he whirled around and you nearly bumped into his chest as you followed behind him quite closely.

“If you think for a second that I’m going to -”

“I do think for all the seconds,” Harry nodded, “Don't fight me on this, Y/N. You will lose. I will wrestle you if that’s what it comes to and I’m like, twice your height.”

“My dad taught me how to fight,” you said cutely and brought up your fists.

“That’s adorable, sweetheart,” Harry smirked, “But that couch is calling my name and I’ve slept on many before. One of my redeeming qualities is that I can fall asleep anywhere, so please,” he stepped aside, “After you.”

Harry sat down on the couch once you retreated into the room, and when he heard you approaching again he didn’t think anything of it. “Would you like some water?” you asked.

“Oh that would be lovely thank -” Harry stopped as he saw you and nearly fell to the ground at the sight of you. You were in pajamas, the most elegant pajamas Harry had ever seen and your hair had been pulled from the braids, wavy and falling around your shoulders.

You noticed him ogling you, lost for words, and you blushed. “I didn’t know we would be staying the night or I would have um ... I wouldn’t have brought such ...”

“You look great,” Harry squeaked, turning away because he knew he couldn’t control himself, “Shit,” he whispered and squeezed his eyes closed.

“Here you go,” you whispered, handing him the cup of water and sitting with your legs curled up under yourself on the seat to the right of him. Harry still wasn’t meeting your eyes, in fact he was looking in the opposite direction, and you realized that you were making him uncomfortable.

“I’m sorry,” you stood, “I can go put on a sweater. I know these are ... I bought them once for an occasion and I haven’t done laundry so ...”

“You bought them for an occasion?” Harry asked, finally turning and looking at you, “You had an occasion for those?”

He watched your cheeks heat up as you let your hair fall in your face. He’d never seen you like this before. You were always the confident and bold type, and yet here you were shy in front of him, crossing your arms over your chest and shying away.

“I was engaged,” you mumbled, “Bought them for the honeymoon. We were going to Venice.”

“You were engaged,” Harry rose his eyebrows and stood, stuffing his hands in his pockets. “I’m uh ... I’m sorry?”

“Oh no,” you rolled your eyes, “Found him in bed with one of his friends weeks before the wedding. We rushed into the engagement. It was years ago,” you waved it off.

“I never knew,” Harry whispered.

“We don’t ... talk about, you know, this kind of stuff,” you shrugged and gave him a half-hearted smile. “How would you know?”

“I wish we did,” Harry said honestly, “I wish we talked about this kind of stuff. I wish we were more open with each other. I wish I knew everything about you. I wish I knew what your favorite color is, what dessert you prefer since you don’t like chocolate. I wish you told me your fears, you future plans, your likes and dislikes. I wish I knew your thoughts. I wish you trusted me enough to share your thoughts with me.”

Harry squeezed his eyes shut and dug the heels of his hands into his itchy eyes as he felt the need to allow tears to fall. “God, Y/N, I’m so sorry,” he shook his head, “I’ve been compressing these feelings for months, I just ... You are so loving and confident and I am so in awe of you.”

Harry let his hands fall as he looked at you standing before him, glass of water in your hands as you watched his face earnestly. “I ... I haven’t said anything because, well, because it wouldn’t be professional and I was afraid of losing you as a pilot, you know? But now we’re in a hotel room in Paris and you’re wearing the absolute best pajamas I’ve ever seen in my life and we’ve basically passed every professional line there is to cross.”

You placed your glass down slowly and Harry felt his whole world slow down. “Harry ...” you cleared your throat and reached your arms out. He willingly nearly fell into your arms for the hug you were offering, digging his nose into your neck as he tightened his grip around your waist, bunching the material of your pajamas in his fists as you ran your dainty hands up and down his back.

You fingers ran up his broad back to nestle in the base of his neck, gripping to the hair there as Harry bent over slightly and you clung to him as he tried to consume more of you and all of you.

“I think you’re going to have to get a new pilot,” you whispered, pulling away from Harry and brushing your fingertips across his face.

Harry’s eyes fluttered shut as two tears sprang from his left eye, a sniffle contorting his face as the force of knowing how you felt about him nearly broke him down to his knees.

“I really thought ... I feel so dumb. I -”

“No, no no Harry,” you stepped forward and cupped his face in both your hands as you ducked down slightly to capture his gaze. “You need to get a new pilot because I don’t trust myself to keep a professional lifestyle as your pilot when I’ll want to be sitting next to you. I care for you Harry, so much, and ... and it’s been difficult for me to do my job when I’m around you. Do you know how difficult it was for me to know that you were flying across the country just to attend some girl’s art show? The jealously I felt was embarrassing,” you chuckled as Harry looked at you in awe.

“Yeah?” was all he seemed to be able to form together. You did feel something for him. You cared about him. You appreciated him probably as much as he appreciated you. Oh God, you did care for him.

He let out a small chuckle through his tears, stepping away for a moment to wipe them from his eyes as you smiled at him and laughed as well.

“I’m gonna kiss ya now,” Harry mumbled and waited for your nod before diving forward and capturing your lips with his. His arms snaked around your waist, arching your back as he pulled you flush against him and your once more allowed your fingers to find purchase in his curls. Your lips were soft and eased every concern from Harry’s overworking brain as he felt the need to kiss you until his lungs collapsed.

Pulling away, you both had flushed cheeks and swollen lips as Harry leaned back in to give you a soft peck. “You can come and sleep in the bed,” you whispered, “But I’m not promising any funny business.”

“I promise,” Harry chuckled, nuzzling his head once more into your neck.

“I’m going to have to find new clients,” you sighed as Harry wrapped his arms around you once you were both in bed.

“No,” Harry shook his head as he nearly consumed you and wrapped himself around you, clinging to you like a koala. “No I think we can make it work,” he mumbled against your skin. “Don’t want ya goin’ back to Jack.”

You laughed, “Oh God that would be awful.”

“Besides,” Harry yawned and kissed your shoulder, “If ya were ma’pilot then we could do it while ya put the jet on auto-pilot.”

You couldn’t help but laugh as you ran your fingers through Harry’s hair. “Oh love, that’s not how auto-pilot works. But we can figure it out, sure.”

Harry kissed along you from your shoulder to your collarbone and then back up to your lips. He couldn’t get enough of your skin, the taste of you, and the way your face looked when your eyes fluttered open after a kiss. It was everything he had ever imagined and more.

“Well, at this point love, I would really follow you anywhere. And I’m not only saying that because you’re the pilot and I’d literally bed allowing you wherever you take me, but more like because I’ve got a bit of the fallin’ in love thing goin’ on.”

You smiled down at him and kissed his forehead, scratching at his scalp as his eyes fluttered closed and he let out a groan while resting his head in the crook of your neck. He felt warm, so impossibly warm and cozy with you that he never wanted this moment to end. “Wherever you go,” you chuckled, “I go.”

“Even if it’s to support some girl in her endeavors?” Harry chuckled.

“Oh shut up and get some sleep,” you laughed, “Some well-deserved sleep, love.”

That night was the best sleep Harry had gotten in a while. In fact, he slept so well that he decided it would be pointless to fly back until the following day and just stay in. You spent the rest of the day in bed watching movies, ordering room service, and talking to get to know each other better. And it was the following night, the night before your departure, that Harry hardly slept. But you didn’t sleep much either until the early hours of the morning and considering the bed head Harry had the next morning and the marks along your collarbones, neither of you minded in the slightest.

“If ya put us on auto-pilot for a bit on the way back love I’ll give ya a good snog,” Harry whispered, squeezing your bum as the two of you walked up the steps of the jet.

“So eager to join the Mile High Club, are ya?” you chuckled, “Not all it’s cracked up to be, ya know.”

Harry paused for a moment and regarded you as you set to work. “You are full of so many secrets,” he said in awe, “Teach me your ways.”

“My ways, Harry,” you whispered, running your hands down his chest once the door had closed and giving him a wink, “Will take way longer than auto-pilot will allow.”

You gave him one last wink, pushing him down into his chair, before you walked over to the cockpit. Before closing the door you turned and smiled at Harry, “Enjoy your flight, Mr. Styles.”

--

Let me know if you’d like more one shots like this one! Or if you have any ideas or requests for future writing! Now that my life schedule is more solid, I know my free time and how much of a work load I have, so many more writing like this will surface! Thanks!

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