Fuckboy!high school! Tom Holland AU
y/m/n-your middle name
y/s/n- your school name

Tom Holland, the most popular guy in y/s/n, good grades, good looks and of course he was fuckboy jock.
Y/f/n y/l/n, well known in the school,not perfect grades but still good and best friends with Maddison, one of Tom's ex girlfriend- the longest relationship he's had, being almost a whole month.
----
"Whos this?" Harrison chuckled, walking towards Tom, who had his arm around yet another girl "hi, i'm Jessica" she smirked,
"And apparently has a thing for my best friend" Tom injected,not like he cared anyway,she was just another fling for this weekend, she rolled her eyes then walked away "another one, Tom? Man you can't stick to one girl for a month" Tom raised a brow and smirked "there was that one girl uh...Maddison I believe?" Harrison nodded along "actually Tom, you and Maddison only lasted for half a month" Jacob said as he and Harrison did a boy-ish handshake. "I bet you can't stay in a real relationship for a full month, nothing behind her back or even texting or something behind her back.." Harrison nudge Jacob, who joined in "yeah, and 20 bucks -"
"for each date, 30 for a kisses,"
"And a full 50 for sleeping with them"
Tom rolled his eyes, but nodded "alright, i'll take that action, i can get any girl"
"Right, any girl, so we choose who"
"And we choose her" Jacob pointed "yes! I think her name is... y/n" Harrison smiled smugly . Tom nodded then looked at the crowd she rolled with, everyone in the group were easy targets, hell he got the queen bee of the group to date him, he snickered "too easy man, i could do it for 2"
"Alright,do it for 2 months"
"Double the pay first" Harrison and Jacob looked at each other then nodded "alright, double or nothing and you can't tell her about it, now go on,show us"
-----
"Hey, Stacy you got the homework from last night?" Maddison asked as she fixed her makeup in her mirror "yeah, not number eight thou-" "holy shit Tom's coming this way" she interrupted
"hello ladies" Tom said, doing his signature smirk "what do you want Holland?" Rebeca questioned, annoyance laced through her words "i just came over to ask one of you something" he looked all of them in the eyes, they all swooned, despite hating him for breaking Maddisons heart in half a month.
"y/n" he said, finally his eyes landed on her "wanna go out for dinner? Tonight?"
Y/n smiled sweetly and again, Tom smirked
"no thanks,i'm busy tonight sorry" she glanced at her friends and nodded a goodbye to Tom as she walked away.
---
"Hey y/f/n y/m/n," Maddison smirked taking a seat next to her best friend, of course the other girls followed "whats up Madds?"
"Jessi had the idea to maybe...yanno play with Hollands heart a little bit."
"I think someone rejecting him messes with his heart and ego enough" y/n replied with an eye roll "no,no you have to get with him"
"Madds i-"
"I'll pay you 50 bucks" y/n sighed "i'm not going to date him just to break his heart like that, besides if i were to get with him, i wouldn't do it for money, maybe i want to date him" Maddison smiled "i knew you liked him! Mister neighbor boy"
again, y/n rolled her eyes "i liked him a long time ago Maddison, that crush for him is gone. Boom." She talked with her hands, as if making an explosion
"Gone, that's why you dated him remember?" She laughed then nodded standing up "i gotta get to first, but if you want the 50, you know where to find me?" Se winked leaving the room to go to her own class.
"Psst y/l/n" a voice called from behind "what do you want Osterfield?" She whispered back,not bothering to turn her body to face him
"you got some nerve, hurting Tom like that in front of your friends" Harrison knew that Tom, at one point did in fact have a crush on y/n, to be fair they were 10 at the time and he lowkey shipped them, that's why he chose y/n
this time, she turned "What the hell are you on about?"
"We encouraged him to finally ask you out and you turn him down saying you were 'busy' " rolling her eyes, she turned back around to continue her work "I don't know what you think you're doing but its not going to work on me, i know him.hes my neighbor and hes, just... beside i actually am busy tonight, i got work"
"Right, you're not going to sit at home and binge watch That 70's Show again?"
"You guys still peek through my window?" She groaned "well you leave the curtains wide open so.."
"Creeps" she mumbled, closing her notebook and leaving class.
-----
"Tom," Harrison called,walking over to his friends "turns out, she actually is busy tonight,apparently she's got a new job" the group of boys- excluding Jacob turned towards Harrison
"What are you talking about?"
Jacob chuckled "Tom took the challenge to stick to one girl for 2 months, 40 bucks for dates,60 for kisses and 100 for sleeping with her"
all the boys smirked "doubt you can do it Holland, you've got a reputation, who is the girl anyways?"
"Y/f/n y/l/n" Tom replied
the boys began to murmur "oh shit your hot neighbor?"
"If shes got work..i guess i'll just pick her up then"
"You don't know where she works yet"
"Our mums are friends, they've probably talked about it"
----
"Hello?" Y/n answered her phone "hey, so remember your childhood boyfriend?" She groaned and rolled her eyes "what about Tom mum?" Her mother chuckled on the other line "well he offered to pick you up after your shift-"
"woah,hey i thought dad was picking me up"
"Well Thomas offered and your father and I decided to go on a last minute date"
Y/n sighed "alright..whatever, okay, i gotta go. I'll..call you if he's not here or something.." Groaning, she put her phone away into her locker then placed on her hat, ready for her shift of handing out popcorn and drink.
When her shift was finally over, she took all her things and stepped out "y/l/n" he called, as the windows rolled down "hey Holland i think i'll just..walk" he scoffed "no way, your parents will kill me if i let you do that, and it's about to rain"
"It's not about to-" and suddenly, just like Tom said, it began to rain "alright but i'm sitting in the back-"
"Hey y/n!" The window to the back door rolled down,revealing Paddy and 2 of his other friends "hey boys" she smiled,sweetly to them
"Looks like you're going to have to ride shotgun" Tom smiled innocently, then got out to cover y/n with his jacket to refrain getting more wet while leading her to the car. "Thanks i guess.." she mumbled before Tom shut the door for her "hey y/n, guess what i got on the essay!" One of the boys called "you passed it didn't you" he nodded "so much more than passed y/n! I got a 95% on it! You're so like..magic, i don't even know how it happened"
Y/n chuckled "well a magician never tells" Paddy looked between his friends, y/n and Tom "hey Tom,remember how y/n helps us all in English" Tom nodded, keeping his eyes on the road "what about it?"
"And remember the fact that you're failing English?" Tom stepped on the break "shit! Sorry red light i didn't see.." Tom turned to look at the boys to make sure they were all okay, then he looked at y/n "you okay?" She nodded,slightly shaken up, but she was okay. "Good... uh what were you saying Paddy?" Paddy cleared his throat "i was saying, that maybe if you'd ask, y/n could help you out in english, she like a goddess in it" y/n's brows shot up "a goddess Paddy?" The two boys next to him chuckled "not just in english.." one said, causing Paddy to smack his arm "well yeah, you're uh..really good at it.." the other two nodded "you helped the three of us really, we got the highest grades of our whole class!" Y/n smiled and raised her hand to get high fives from all of them "that's wonderful!" The one to the left-Tyler spoke up
"so now that you work at the theater, do you get discounts?" Y/n nodded "i can, yeah, why you got a date?" He chuckled lightly "well maybe.." she gasped then turned towards the boys "no way, you're too young" he just smiled then looked at his friend "y/n, how bout you go on a 'date' with the one of us that got the highest score" she eyed the three boys then nodded before turning back to the front
"i'm gonna need some proof that, that's really your score" suddenly, three papers were handed to her from behind "ohh Shawn, Tyler you both were really close.. but looks like i'm taking Paddy out on a 'date'" she turned back around to hand the boys back their papers, to see Paddy as red as can be "you alright Pads?" He nodded vigorously "cool,text me when you've got no homework and we'll see whatever you want. Thanks for the ride Tom" y/n said, before flashing the younger boys a smile and Tom a wave.
"So you like the neighbor girl huh?" Tom turned to his youngest brother "yeah well.. so do all of you!" He defended himself, Tom snickered while driving onto his driveway "at least Paddys got a date with her though Tom, unlike othersss" Tom rolled his eyes "okay, that's enough, come on,we're home"
Once out, the boys ran to the door and were greeted by The one and only Harrison Osterfield "hey-"
"wait..i've got a date with y/n... I'VE GOT A DATE WITH Y/N!!" It finally had fully registered in Paddy's mind that y/n was going on a date with him, even if it wasn't a real date per se, he was estetic. Harrison raised a brow "she tutors them in English and he got the highest grade so she's taking him out for a movie" Tom replied, taking a seat next to his best mate "right,maybe you can get her to tutor you too,get a good grade then boom the dare starts" Tom rolled his eyes "don't think that'll work but if all else fails..which it won't, i'll get back to that"
---
"Hey Paddy, where you off to?" Tom asked sitting himself down on the couch "y/n's taking me out to see a movie!" he smiled happily as he put his shoes on, "did you tell mum and dad already?" he nodded before heading out the door.
"y/n?.." Paddy walked over to see why her car door was wide open ad the hood was up "hey Paddy...I'm sorry, i don't think i can drive us, my stupid car.." lucky for them, Tom was watching from the living room window and smirking to himself, as he saw an opportunity to get to know y/n again, and more importantly, get the bet over with.
"I couldn't help but see how you two are still here and not at the movies.." Tom smirked walking over to them, Paddy frowned "yeah, but its okay, we can uh..still hang out right y/n?" she nodded "yeah, of course we can..sorry we can't watch into the spider verse" Tom perked up "hey, i haven't seen it yet, maybe the 3 of us could go" Paddy kept looking over at y/n and Tom, he figured, since y/n was too old for him, he'll set y/n up with Tom. "I'm okay with that if you are" he grinned "sure"
At the movies, Paddy and y/n convinced Tom to buy them popcorn and snacks, "i call the inner seat, y/n you sit in the middle!" she raised an eyebrow, "uh..Paddy what are you trying to do?"
He shrugged "nothing, come on, sit down" Tom nudged her "what you afraid we'll talk throughout the whole movie like we did when we were kids" she shook her head "oh please, i have self control now, not like i'd want to talk to you anyway" as she said that, she smiled "you used to say that all the time" Tom chuckled "yeah well, the first parts true-"
"y/n? Tom?" a voice interrupted their conversation "hey Maddison.." Maddison sent y/n a smirk "what are you two doing here?"
"Definitely not on a date!" Paddy said from behind a bag of popcorn "so you're on a date then?" both Tom and y/n glared at Paddy, who blushed and smiled innocently "right well, come find me when this date thats not a date is over 'kay? 'Kay" she then continued her walk up to sit with her younger brother. "So.." "lets just watch the previews yeah?" y/n glanced behind her and saw Maddison mouth "50 bucks" she shook her head and forced herself to look back to the front as the lights began to dim.
-----------
"Hey, i can walk or get a ride from Maddie from here,-" "NO!..uh i mean no, c'mon y/n please come home with us, we can wait while you talk to your friend." Paddy pleaded, y/n bit her lip (̶T̶o̶m̶ ̶t̶h̶o̶u̶g̶h̶t̶ ̶i̶t̶ ̶w̶a̶s̶ ̶a̶d̶o̶r̶a̶b̶l̶e̶)̶ "yeah, we'll get starbucks before we get home" she giggled ̶(̶s̶h̶i̶t̶ ̶s̶h̶e̶'̶s̶ ̶s̶o̶ ̶a̶d̶o̶r̶a̶b̶l̶e̶)̶ "how could i pass up free Starbucks..or free anything to be fair?. I'll be right back"
y/n found Maddison, who was looking through her purse "so theres this party"
"No party, i have a lot of writing to do"
"Fine then, here's your fi--"
"Maddie, i told you, i'm not going to date him for money, plus this wasn't even a date, it was supposed to be just me and Paddy as a 'you aced your english test' date, Tom only came along because he drove us" Maddison raised a brow "so you let him tag along to the movie?" she shrugged "he paid for popcorn and snacks," glancing back towards the boys, who were both watching her "i gotta go, Tom's my ride" Madison smirked "you mean his dicks your ride"
"Fuck off Maddie" y/n laughed before walking back to them "ready?" and they were off "why starbucks? Its night" Paddy said as they stood in line "you're so right Paddy, we'll get you some water, whilst we get..." Tom turned towards y/n "fraps?"
"fraps." Paddy pouted then perked up "i'll go find a seat, can you convince him to get me at least hot chocolate?" the Starbucks they were at was basically empty, but they decided to let him go,
as he left, Tom smiled, he's caught on to what his little brother was doing. "So, how you gonna convince me to get him at least hot chocolate?" she looked up at Tom "well obviously i'm gonna use my mouth" Tom turned his body towards her,bewildered "what"
"To speak and use commodious words that you probably wouldn't understand..." she glanced at him with a smirk "get your head out of the gutter Holland" he rolled his eyes "you do know what commodious means right?" he nodded with a blank look on his face "its another word for big"
"I knew that" he said, walking up to the counter "hey Tom" the girl smiled "hey..uh, Morgan.." he studied her name tag "you were supposed to call me like a week ago.." he gulped and glanced over to y/n, who shrugged next to him "right, sorry about that.. Can i uh..order?" Morgan nodded disappointingly "right, we'll i'll have two grande caramel fraps and a tall peppermint hot chocolate" as Morgan told them their total, both y/n and Tom pulled out their cards "i got it--"
"You paid for the movie"
"Yeah because i got a discount, you already paid for our snacks"
"You put snacks in your mouth, drinks goes through the mouth too, i win the argument and i pay"
"You drove us here"
"I don't see the logic in that darling" Tom bit his lip, trying to conceal a smile "look, i don't care who pays, you just need to pay for them" Morgan interrupted "right, sorry," Tom stepped up and paid for them "thanks" y/n blushed and Morgan rolled her eyes "no offence y/n, but he's not even gonna stick to you for a full week" if looks could kill, Morgan would be dead, in fact, y/n was thinking of ways to kill her with words, she couldn't help it, the little girl inside her was fuming, she knows Toms reputation, but the urge to fight anyone who ever insulted her childhood best friend was tempting
"y/n, c'mon, our drinks are done" Tom took her hand leading her away, he knew that look in her eyes, she had the same one whenever someone used to bully him in their younger years, Harrison said that Tom had the same look, even now when someone said something mildly bad about her. "Right, sorry"
"Nice! How'd you do it y/n? Sam and Harry can't, mum and dad aren't that easy either" Paddy grinned as Tom handed him his hot chocolate "she used her mouth by using this big word com..uh yeah"
"Commodious?" Paddy questioned before sipping his drink "yeah, how'd you know that word?" Paddy pointed at y/n "i told you already, she's a goddess of english" she shook her head, blushing "I'm not a goddess Pads,"
"Hey, didn't you get like a 95% in our english class sophomore year, thats higher than..what his name? The guy who always aces everything?(HAHAHAH GUYS THIS WAS ACTUALLY ME and the dudes my friend so i bring it up whenever i can to annoy him:) )" the blush on y/ns cheeks grew "uh..yeah, but" Tom smiled at her "see goddess" the two brothers said at the same time "hey, speaking of, when we picked you up the other day, uh.. My parents heard i was failing english again and i..i was wondering if you could tutor me too?.." she nodded "sure, anything for an old friend" ̶a̶n̶d̶ ̶f̶o̶r̶m̶e̶r̶ ̶c̶r̶u̶s̶h̶ "cool, then its a date uh! Stud...study date" Paddy almost spit out his hot chocolate from laughing, but covering it up with a cough when Tom glared at him "i know what you meant Tom"
"Sorry to interrupt, but we're closing" a woman smiled at the group "oh! Yeah, sorry" the trio stood up, picking up their drinks and leaving. "What 'ya doing the rest of the night?" Tom asked letting go of the door after y/n went out "well tomorrow is Saturday so probably writing my book all night"
"Still writing Peter Parker fanfiction?" she was quiet for awhile then "yes, but thats not the book i'm talking about" Tom smiled, thats how they had become close when they were younger, the love of spider-man "okay, well now you're going to a party with me after we drop off Paddy"
"But--"
"No buts, Maddie usually pulls you out to parties but i haven't seen you at one in awhile, plus i know you have writer's block" she shook her head "no i don't"
"Alright then, what's happening in the scene you're writing?"
"My main character is talking with her parents who are vampire hunters, and her soulmate parents who are vampires.."(lol anyone reading 11pm?)
"Then?" Tom stopped at a red light then looked at y/n with a raised brow "then they...dammit, how the hell do you know i have writer's block?" he shrugged then drove "i can still read you i guess, you gotta go to this party with me, promise, right when you think of something,i'll drive us back home. Deal?" she sighed "you should go to the party y/n, before you start tutoring Tom, or you'll be stuck with him for far too long and have no fun at all" Paddy smiled from the back "screw it, fine, i'll go...but its not for the reason you said" y/n chuckled pointing to Paddy. "Alright, out Paddy-"
"can i at least go change first? I look disgusting for a party"
"y/n you always look pretty" Paddy said, blushing then running into his house. "I think you look just fine the way you are, but go ahead" she nodded then quickly ran to her house to change

(Your outfit)

(Toms outfit)
"Oh you changed too"
"Look at that a unplanned lowkey matching outfits, perfect couple-- uh..couple of friends" y/n shook her head with a small laugh "yep, couple of friends"
--------
"Tom!" Harrison called as soon as they entered the house "oh! y/n hey, sorry i didn't know you were coming so..i didn't bring you a drink too.." she smiled and shook her head "its fine, i'm uh..i'll go find Mads"
"find me when you wanna go yeah?" he reminded her before she walked off "alright so, you want your payments now or later when you complete it?" Tom smirked "pay up now Haz"

Just when we all thought he wasnt gonna go through with it...