#drew starkey imagine | chleem (2025)

miniseries; basketball player drew x high scl student reader

Summary: You lose your virginity to a random guy at a frat party miles away from your home. A few days later, you find out that he’s your brother’s competitor, for the regional colleges’ basketball tournament.

Genre: strangers to lovers, smut, angst, fluff

Warnings: cursing, age gap (18 & 24), protected sex, etc.

⋆.˚ please dont copy my work, if inspired please tag me

⋆.˚ this is entirely fictional, if uncomfortable then don't read

♡⸝⸝ bit long but enjoy! | p1 | p2

─── ⋆⋅☆⋅⋆ ──

4 years later

“Drew, Drew Starkey.”

The waiter checks his name off the list, and gestures inside, “follow me then, Mr Starkey.”

Drew follows the waiter in, looking around the place. Hawks rented the entire restaurant for the night, just like every year, to celebrate the new season. It's his third season with Hawks, so he knew the procedures well enough now.

Tonight will just be free food, bonding with teammates, etc. Could you say he was looking forward to it? No. He would much rather stay home, especially this year.

Why especially this year? Because of his new teammate, Luke.

It wasn’t hatred or anything; in fact, they had amazing chemistry on the court. Communicating through nods or glances, as if they’ve known each other for forever. Really, the coach was shocked at how good they did during preseason; he’s now convinced there’s a chance of winning.

Luke seems to have matured, anger issues not the same as before and actually willing to listen to advice. He was friendly towards Drew, and overall, did not look so bothered about losing the championship during college anymore.

It was Drew who felt uncomfortable around him. Why? Well, he fucked his virgin sister, who was 18 at the time. Worse, whenever Drew stares at Luke for too long, he sees your face. Your eyes, nose, lips, everything.

“Nice suit, man,” one of Drew’s teammates and best friend, Jay, compliments him, as the two approach each other first. Every year it was required to wear formal for this occasion, since high executives would be here to celebrate too. Drew, has worn the same black suit for the third time now.

“Yeah, same with you,” Drew smiles, the two of them engaging in a small hug. “Um, are we seated together?”

“Yeah, over there,” Jay points over to a table near the window. Each table had a maximum of six people, and already two of their teammates were there. “Man, we should some drinks first.”

“No need to remind me,” Drew replies, as the two of them head to the bar area. The goal is to get drunk enough so that the executive's’ speeches would sound interesting, but sober enough to make basic human interactions.

“So, you came alone this year too?” Jay asks, ordering a whiskey, which Drew also signals for.

Drew smiles sourly, his friend reminding him about his single status again. Plenty of hookups throughout the years, but never a proper girlfriend due to his busy schedule. “Y’know me. Too busy for that shit.”

Jay nods, as the whiskeys are presented in front of them. Drew immediately downs his, while Jay just takes a small sip. “Well, I’m seeing someone, if you’re wondering.”

“No shit,” Drew laughs, thinking his friend is kidding. Jay smiles down at his drink, probably thinking about the girl. Oh. He really is seeing someone. “Who’s the lucky girl?”

“Her name’s Phoebe.”

“…and?”

“Yeah. That’s all I’m telling you.”

Drew shakes his head, ordering another whiskey. So much for being friends. “She has a sister, by the way,” Jay speaks up. Oh. Drew knew where this was going. “She might be the perfect one for you.”

Jay’s setting him up. Again. His friend has failed every single time, and it seems like he wasn’t gonna give up. “Hey man,” Drew pats Jay’s shoulder, pursing his lips. “Just quit, okay? I don’t date. Y’know that.”

“When’s the last time you’ve dated then? Have you ever even had a girlfriend?”

Drew frowns, taking his hand off his friend. “Just, no. Please.”

Drew hears a sigh from beside him, and when his second whiskey arrives, he sips on it slowly. “Fine. I just think, that you would be very happy in a relationship.”

Drew smiles against his cup, finding that statement ridiculous. Society was weird, thinking that if one stays single for too long, it meant that they were…depressed in some way. It was tiring.

“Hey, Luke’s here,” Jay suddenly comments. Drew turns around, scanning the place for Luke.

Sure enough, there he was.

And fucking hell.

His eyes land on you, standing beside Luke.

Was it even you? He wasn’t so sure. From far away, it did look like you.

“We should go greet him,” Jay elbows Drew.

Drew did not want to greet him. He is very comfortable here, right next to the bar.

But Jay urges him, leaving him no choice but to walk over. And until Drew was standing directly in front of Luke, was he sure that it was you.

Fuck.

Four years later, and Drew’s body still has reaction towards seeing you. It brings him back to the first night he laid eyes on you, thinking how innocent & pretty you looked in a crowd of drunk and chaotic college students.

You look…amazing. Drew was pretty sure his eyes were widened to the maximum point right now, his brain trying to process the sight of you. Especially, the red dress you were wearing, that's making his imaginations run wild.

No. He must be dreaming right now. After four years, he sees you again? No, this shit only happens in movies, red-string type shit. Was he getting drunk already?

“Um, Drew, you okay?”

Drew quickly averts his gaze back to Luke, his grip on his glass cup tightening. “Yeah, yeah, um, who’s this?” Does he sound cool right now? Because he wasn’t so sure if he was playing his usual chill self.

Luke wraps an arm around your shoulders, pulling you closer. “Meet my sister. Y/n. Y/n, this is Drew and Jay. My teammates.”

Shit. So it is you. The girl that Drew can’t seem to forget, the girl that haunts his wildest fantasies for four years now.

When Drew makes eye contact with you, he expects you to have some sort of reaction. But you don’t. In fact, you just quickly glanced at him, a polite smile on your lips. Do you even remember him? “Nice to meet you,” your voice causes Drew to freeze yet again, his mind going back to that night. Your moans, your laugh, your-

“Dude,” Jay elbows Drew yet again. “Aren’t you going to shake her hand?”

It seems like you already shook Jay’s hand, and it's Drew’s turn now.

He licks his lips embarrassingly, and he shakes your hand. Yep. No doubt it was you. He remembers clearly about the way you scratched his back that night, the tug of your hands in his hair, and your fingertips on his abs-

“Um, kind of need my hand back,” your voice cuts him out of his thoughts.

Oh. He was still holding your hand. He retreats it reluctantly, feeling his ears heat up. Gosh, why is he so flustered right now? He feels the stares of Luke, or more, like glares. “So…where are we seated?” Luke asks.

“Near the window.”

“Great. Um, we’re not late, are we?”

“No one really cares.”

Luke and Jay continue to engage in small talk, whereas Drew just gives up on listening. Not just give up, he literally was unable to engage in anything right now. It feels like he's in a dream.

He can’t tear his eyes away from you, absolutely captivated by you. By this matured, attractive presence you gave off. You were just standing there, trying to appear interested in this small talk.

And a question he kept repeating in his head was: do you remember him, like how he remembers you? Do you still think about him from time to time, like he does about you?

You definitely can feel Drew’s stare, his stare making you feel as if you were under a microscope right now. You turn and meet his eyes, and he panics, yet again.

Your eyes tell nothing, of whether or not you remember him. And the small smile you give him confirms it; you forgot about who he was. Fuck. Now Drew felt like the biggest fool to exist.

“If everyone could get back to their seats! The food will arrive shortly,” the host announces through a loud microphone.

“Let’s go then, I’m starving,” Luke squeezes your shoulders, to get you moving.

“Same,” you look away from Drew, and let Luke guide you over to your table.

Drew immediately gulps the rest of his whiskey down, loosening up his tie. Fuck. This was going to be a long night.

——

Drew wasn’t one to eavesdrop. In fact, he hated eavesdroppers. Why are you listening on someone else’s private conversation?

Well, Drew hates himself very much right now.

You sat near the window, at the very end of the table. Across from you was Drew’s other teammate, Kirk. He sat next to Kirk, and across from Luke. The whole night, it was very obvious that Kirk had a thing for you, asking you questions about your life, hobbies, etc.

So now, Drew knew that you’re currently studying law in college, you hate tomatoes but love ketchup, you like museums, you have a horrible sleep schedule, you want to adopt a cat, you hate the cold-

“You’re single, right?”

That makes Drew choke on his food, causing the table to pause and stare at him. He coughs, feeling his whole face going red. “You okay, dude?” Kirk chuckles, patting Drew’s back, as if it’s any help.

Drew nods, trying to suppress his coughs with the help of water. While drinking, he glances at you, who looks at him with worried eyes. He puts his cup back down, clearing his throat, “so, are you?”

He ignores the skeptical stares from Luke, his eyes only focused on you. Please, please, say yes.

You turn away from Drew, just as Luke suddenly speaks up, changing the topic, “can we get another round of this lobster? Its fucking delicious.”

What? Drew’s gaze stays on you, seeing how you bite down on your bottom lip, eyes glued to your plate. Was it, a violating question? Drew had no idea, but seeing how quickly your mood changes, it leaves a bad scar on him.

——

Huh. you’re staying at the same hotel as him. Well, not just him. The entire team, actually. Luke must have arranged it for you.

Drew stands behind you, hands in pockets, trying to look as if he wasn’t bursting with joy. While waiting for the elevator, you lean on Luke’s shoulder, your body ready to give up.

The elevator opens, and the remaining people all squeeze towards it.

You eventually get squeezed into the corner, with Drew close by. Super close by. With no space at all, Drew is forced to lean into you, his arm against the wall to support him.

This close proximity was driving him insane.

He feels your breast press closely to his lower chest, your face planted really close to his neck. From this proximity, he certainly can smell your perfume, shampoo, everything. He looks down at you; and surprisingly, you were already staring up at him. You send him a lazy smile, your eyes squinted up at him.

Cute. He sends you one too, although his smile might be bigger.

The ding sound is heard, and most of the people inside rush out. Drew was disappointed; he wanted to stay like this for a bit longer.

He gets himself off of you, now that there’s more space in the elevator, leaning against the wall. He wants to look at you (he already stared a lot during dinner though), memorize more of you before he goes to bed, but Luke turns around and faces you. Drew bites his lip, staring into the ceiling. “Told you tonight was fun, right?”

Okay, now Drew needed to eavesdrop.

“The guy in front of me was asking too much.”

Yes. Fireworks went off in Drew’s head. “Yeah, Kirk’s a dick. Don’t, don’t date him,” Luke…jokes? Drew wasn’t sure. “Or, I’ll kick his ass.”

“Wouldn’t even dream of it,” you chuckle, which makes Drew glance at you. He makes sure to get a quick look of your smile again; fast enough so Luke doesn’t notice.

“Do you at least feel better now?”

“…yeah.”

“…I know you’re lying, y/n,” Luke disappointedly says.

No reply heard from you; the ding of the elevator ending the conversation. Drew looks at the screen; the 18th floor. “Goodnight,” you say to Luke, pushing yourself off the wall. To Drew’s surprise, you wave at him. “Goodnight,” you repeat, the same lazy smile on your face.

“Goodnight,” Drew replies, the smile appearing on its own.

The door closes after you leave, and Drew gets hit with a sad realization; he might never see you again. And he hates that thought.

Four years. After four years, he gets another chance to see you. And he’s just gonna let you walk away? Just like he did the first time?

He gets mad suddenly; remembering the lack of interactions the two of you had the entire night, all stolen by Kirk. Luke’s right, Kirk’s a dick. But also, a lucky bastard. He got to sit directly across from you, as well as talk to you. Lucky son of a bitch.

“Are you… gonna get out?”

Drew snaps out of it, looking up at the elevator screen. 24th floor. Luke is holding the door open for him, wondering why he hasn’t stepped out. “Sorry,” Drew murmurs, walking out. Luke follows him, as the two of them had rooms right next to each other.

“You okay, man?” Luke laughs, walking beside Drew.

“Yeah, just drank a bit much,” Drew shrugs, scratching the side of his face.

Luke gets to his room first, “see you tomorrow, then.”

“Yeah, yeah sure,” Drew takes his room card out, pressing it against the door. He gets in without another look at Luke, closing the door behind him.

Huh. So this is how tonight was going to end? Him alone in his hotel room, consumed with the thought of you? (As if he hasn’t been thinking about you for the past four years already) Even Drew was disappointed in himself.

“Fuck,” he curses, still standing in the entrance of his room, running his hands through his hair stressfully. “Fuck.”

——

After knocking on 17 doors, this one might be yours.

Drew stood at the entrance of his room contemplating for ten minutes, whether or not to go see you again. After long chains of thoughts and scenarios, he made up his mind: he’s going to see you.

Problem: he didn’t know your room number. So, he spent almost twenty minutes on the 18th floor, knocking on each door hoping it would be you.

And now, on room 1818. He was mentally & physically tired, but he wasn’t going to give up.

He presses on the doorbell, twice. He waits for a few seconds that felt like minutes, tapping against the wall impatiently. Just as he gets ready to move onto the next room, the door opens.

He looks up, and his eyes widen.

You. You’re as shocked as he is, wondering why someone would knock on your door at such a late hour.

He first notices your slightly wet hair; droplets dripping down your neck. Your makeup is off, and he just finds you even more beautiful than before. His eyes naturally wander down to your body; finding you in a white lingerie dress.

Fuck. His brain is malfunctioning yet again.

“Hello?” He hears you chuckle, which makes him bring his attention back to your face. “Can I help you?”

“Yeah, um, Drew. I’m Drew, from earlier, the dinner?”

“…I know. Can I help you?” You ask him yet again, a polite smile on your lips. You quickly glance down at his body; he’s still wearing his suit from earlier. He must’ve not showered yet, despite it being almost two hours after.

“Um,” he awkwardly licks his lips; All the lines he rehearsed back in his room are now gone. Drew realizes that he’s still standing in the hallway, and he didn’t want to talk to you while standing out here. “Can I, can I come in?”

You furrow your eyebrows, your face clearly showing discomfort.

He mentally panics, and hurries to add, “I want to talk to you, and it’s rather private. And, important.”

You think about it for a few seconds, listing out the pros & cons of this man coming into your room. You look into his eyes, seeing a sense of urgency and yearning in them. Okay. Maybe he can come in for a while.

You step out the doorway, opening the door wider. “Sit on the couch, I’ll prepare…tea? Wine?”

“Anything’s fine,” he says, walking in. You close the door behind him, and when he spots your shoes by the door, he takes his off too.

As he makes himself comfortable on the small couch in front of the bed, you grab your cardigan that rests on one of the dining room chairs, putting it on.

You open the hotel fridge; finding red wine in there. Opening the cupboard, you reach for two glass bottles, and walk towards Drew. He’s taken his suit jacket off, his tie hanging loosely by his neck, his sleeves rolled up. And he’s manspreading, a position you find to be very hot.

You have to admit; Drew was attractive. Even more attractive than your ex. Actually, the most attractive man you’ve ever seen. And, he’s got a charming personality to match it.

But he’s oddly familiar. During the dinner, your gaze can’t help but always drift over to him. Have you seen him from somewhere? Crazy, you can’t seem to remember where you’ve seen him before. An ad? Tv? Huh.

“So?” You start, sitting beside him. You try opening the bottle, but the cork was screwed on too tight.

Drew takes it from you; his hands brushing yours. You watch him effortlessly get the cork out, the pop heard in the room. He pours it into the two glasses, and sets it down. He sends you a small smile when he notices your stares. “Wine?”

“Well, you said anything’s fine,” your lips curl up on their own, as you reach for your wine glass. He offers to clink against yours; and you do, the two of you maintaining eye contact while sipping. After, you put your drink back down on the small coffee table. “Why a late night talk?”

Drew licks his lips, glancing down at his lap. He seems to have trouble forming words, fidgeting with his fingers. You lean back into the couch, curious as to what he’s thinking about.

After seconds that felt like minutes, he said, “You study law?”

Due to the unexpectedness, you chuckle, “yeah. Why?”

He shrugs, “Suits you.”

What is he even saying? “What?” You giggle, at his response.

You don’t miss the tip of his ears going red; even he thinks his response is funny. “I mean, law sounds fun, and you look like lawyer material.”

“Awesome,” you smile at him, trying to hold back your laughter. “And you look like basketball player material.”

His smile mimics yours; just more awkward.

He seems to not know what to say, despite telling you that he had something to say to you. Weird. So, you help him, by asking, “are you nervous about the new season?”

His eyes light up, “My third season with Hawks now. But, still nervous.”

“Third season?” He nods, and you reach for your wine yet again. “Hawks fan?”

“Always been the dream,” he admits to you, “grew up watching them, and when they offered, I just had to say yes.”

“Or because no other team offered?”

Shit. That sounded wayyy too rude. But that was your humor, and also your way of talking. Does he find it offensive? Wait, anyone would find that offensive. You should apologize-

He laughs lightly, taking a huge gulp of his wine. “Come on. Give me more credit.”

So…he isn’t offended by your words? You shrug, “never seen you play.”

He furrows his eyebrows at you, leaning back on the couch. “You’re lying.”

“Didn’t even know you until tonight.”

“Liar,” his voice drops low, but a smirk is seen on his lips, as if he’s catching you in a lie right now. But you were being honest; you really didn’t know him until tonight.

Unless…maybe there’s a reason why he looked so familiar to you? Ugh, why can’t you remember where you’ve seen him from?

“Really,” you say, looking into his blue eyes.

His eyebrows furrow even deeper, trying to figure out if you were being honest or not. You were. Eventually, he leans forward and pours more wine into his glass. “I believe you,” he murmurs, before sipping on the wine. You watch as he gulps it down; his Adam’s apple moving. “But surely, you’re…a fan of Hawks?”

You shake your head, which makes Drew chuckle. “I…know nothing about basketball.”

“What?”

“Yeah, it’s my brother’s passion, not mine.”

“Okay,” he adjusts himself on the couch, his body now fully facing you. “Then tell me about law, or stuff like that.”

“‘Stuff like that’?”

“I might bore you if we keep talking about basketball. So, I’ll listen to you.”

“And law isn’t boring to you?”

“Not if you’re talking,” He sends you a warm smile. Woah. Butterflies that you haven’t felt in forever are now forming inside of you. Butterflies that feel different compared to the ones with Zack. “Come on. Tell me. Like, what’s…what new laws have been enforced?”

You laugh; his perception of law is cute. So, that’s exactly what you explain to him, just in simpler terms. His eyes, lips, body tells you that you’ve got his undivided attention; something that makes you smile while talking.

Huh. Weird how this stranger is willing to listen to you yap about laws & everything, as if what you’re saying was as simple was pie. Huh.

——

“Yes! He said that to me!”

“The audacity,” Drew laughs, making you nod even more.

You’re telling him the story of your classmate, who’s also your academic rival. Once he accused you of sleeping with the professor, that it’s the only reason why you’ve got such good grades. Thinking about it now, it just sounds funny. “It wasn’t true but he was so sure,” you laugh, recalling his red face while confronting you.

“He’s a fucking loser,” Drew continues to add, reaching to pour more wine into your glass. The two of you realize that it’s now empty, and you just shrug at him; not really bothered by it.

You take the chance to glance at the clock; it was two a.m already. The two of you have been talking for more than an hour. You suddenly remembered that Luke told you about an early schedule the team had tomorrow, yet Drew was still sitting here, getting tipsy with you.

“It’s..getting late,” you bring up, pointing at the clock.

Drew turns to it, and his eyes widen. But he turns back to you, shrugging. “I guess?”

Is he not getting what you’re hinting at? So, you just tell him, “Luke told me you guys are doing something early tomorrow.”

Drew stares into your eyes, in a way that gets you nervous. But then he looks away, and nods, biting down on his lip. “Um, yeah, totally forgot.”

You smile politely at him, even though deep down you didn’t want him to go. You liked his company, and although it was mostly you talking, he didn't make you feel bad for it. Drew’s…very comforting.

He grabs his suit jacket, the both of you getting up. “Now I can confidently say, that I know y/n.”

“What?” You smile, wondering what he was saying. You watch as he walks to the doorway, putting his shoes on.

When he’s done, he opens the door, turning back to you. “A very successful lawyer, that handles cases for the president or something.”

You laugh; that only happens in your dreams. You lean against the doorway, staring into his eyes. You really didn’t want him to go.

He leans towards you; giving you a hug. His arms wrap around your shoulders, and you hug his waist. Your nose is now filled with the smell of Drew; just like in the elevator earlier, a mix of cologne & alcohol.

Drew slightly pulls away, just so he could look at you. You do the same, staring up into his eyes, then his lips, then back to his eyes.

He also glances down at your lips, his eyes squinted.

Then, he kisses your cheek.

Then, you stand on your toes, planting a light kiss on his cheek too.

Then, he kisses the corner of your lips.

Then, you kiss his jawline.

You look into his eyes, giving him a smitten smile.

And just like that, Drew couldn’t hold back anymore; he kisses you. The kiss is hungry, passionate, intense, and…

And way too nostalgic for your liking.

Wait. Wait.

You pull away from him, feeling a bit overstimulated. Not just from the kiss itself, but…but because of what it reminds you of.

No fucking way.

It’s all coming back to you now; this was Drew. The Drew.

The one you lost you virginity to, the one that didn’t want you.

Wait. Was this even the right Drew? He looks pretty similar to the one you remember, talks similarly, and strangely, also kisses the same.

“Is something wrong?” His deep voice snaps you out of your thoughts.

Fuck. No. No, it’s not the same Drew. Because, what are the chances of this being the same Drew that took your virginity? Awfully poetic, if this happens to be the same person. Maybe, Drew is somewhere in West Carolina, coaching for some basketball team. And this Drew, was just some doppelgänger.

Okay. Yeah, this, this is just a coincidence. You’re just feeling weird because you broke up with Zack a few days ago. Not a big deal. Just, enjoy having this one-night stand with this attractive man.

You smile, shaking your head. “Just kiss me already,” you murmur, leaning into him. You kiss him lustfully, and he returns it, his hands touching all over you.

He backs you up into the room again, all while his lips are on you. You giggle at his urgency, the door slamming shut behind him.

“Don’t you have to get up early?” You giggle, pulling away.

“I think…it’s not that important,” he throws his suit jacket on the couch, kicks his shoes off, and kisses you again. He kisses you as though it might be the last time he does.

You pull away, just to push him onto the bed. His head lands on the pillows, and he readjusts himself so his back’s against the headboard. He puts his arms behind his head; and suddenly, you’re hit with the same nostalgic feeling.

But you ignore that feeling; it’s in the past now.

He gives you a lazy smirk, as you hover over him, straddling his waist. You can feel his erected cock pressing against your folds. Fuck.

You lean down and kiss him, a euphoric feeling that you might never get over. Your hands are busy; undoing all his buttons in a messy order. He helps you; slightly sitting up and throwing the shirt to the side.

Wow. His body? Sculptured by god himself. “Damn,” you voice out, the words just slipping out. Maybe mostly because of how tipsy you were.

He kisses your collarbone, murmuring, “damn?” There’s a slight chuckle and tease to that, which just makes you smile. Your hands go up to his face, cupping it and forcing him up to stare at you. His eyes…most mesmerizing shade of blue.

Again, you ignore the nostalgic feeling, that similar look in his eyes that the Drew gave you, four years ago. The similarity is uncanny.

“Such pretty eyes…” he murmurs, sharing the same thoughts you have.

His hands slide your cardigan off, discarding it somewhere else. His eyes go down to your neck, leaning forward and sucking on it.

Your head leans back in pleasure; his tongue was skilled, you had to admit. He sucks, bites, licks the area, his hands kneading your breasts through the thin material of the lingerie. His lips are warm and soft, compared to the necklace on you. You shamelessly moan out how good it felt; which just drives him crazier.

Drew’s lips slip lower, sucking on your nipples through the fabric.

“Shit, Drew…” you moan, your hands slipping down his shoulders, running through his abs, and then to the belt. Your hand brushes his boner; fuck. You want him now, the wetness in your underwear proving it.

He smirks against your skin, before pulling away. He glances down at your hands tugging his belt, “didn’t know you were the impatient kind.”

You roll your eyes, pushing him back down on his back. “Just shut up,” you groan, even though the smile was apparent on your lips. You back yourself off his waist, until you were on your knees between his legs. You undo his belt as if you’ve done it before, tugging his pants down.

Holy fuck. You’re salivating at the sight of his dick, fully up and proud.

You just want to wrap your lips around him, letting him use your mouth to satisfy himself. You palm his length through his boxers, leaning down and planting soft kisses along it.

He knows you want to give him a blowjob. He can see the thirst in your eyes. He wants it too; but he stops you, his hand going to wrap around your wrist. “Fuck,” he groans, as you look up at him between his legs. In his perspective, it was a very hot sight to see. But it won’t be as hot as what he’s about to purpose to you. “You… I, I wanna taste you too.”

You cock your head to the side, slightly confused. “So you don’t want me to suck your-“

“Yes, I do but I wanna eat your pussy too-“

“What, what, are you saying-“

Oh. Oh. “69?” You gasp, a slight curl on the corner of your lips.

His lustful and excited eyes confirm it, “you up for it?”

Your pussy is screaming ‘yes!’ But your brain is hesitant; you’ve never done the 69 before. With Zack, he’s tried missionary, doggy, cowgirl, spooning, etc, but never the 69.

Hell, why not? Sounds interesting, and with Drew, it might feel heavenly.

“Teach me,” you say, sitting up.

His eyes widen; either from your approval or your unknowingness to this position. But seeing how intrigued you were to try this, he smirks, nodding. He adjusts himself on the pillows, “you’re in luck, I’m a great teacher.”

“Really?” You lift your dress over your head, now, only left with your underwear on. Drew licks his lips at the sight of your breasts, and when you glance down to his boxers; you see pre-cum already soaking it up.

“M-hm,” he’s clearly lost in the sight of your nakedness. “Back yourself onto my face.”

The way he says it; just makes you even more horny.

You do just as he says, not before sliding your underwear off. You keep looking over your shoulder; spreading your legs as you plant your pussy on his face. You make sure to not fully sit on him; afraid that your weight might suffocate him.

You feel his hands on two sides of your thighs, gripping it tight and pulling you further down. “Relax, babe,” he coos. “Just, sit on me, I can take it.”

“You sure?”

“More than ever.”

And you sink your ass onto his face; until you can feel the tip of his nose poking your entrance, his hot breathe fanning it. Oh shit. “Look, you’re wet already,” he teases, licking the side of your thighs, very close to your pussy.

You groan at the feeling, but Drew quickly reminds you to stay on task, “Lean forward.”

You do; leaning your upper body down till his dick was right in your face. You hoist your upper body up with your elbows, creating a bit of space for you to suck his dick comfortably. You pull his boxers down; and moan at the sight.

“Ready?” He murmurs against your pussy.

You pull your hair to the side, “m-hm.”

You wrap your lips around his the tip of his dick, at the same time, he starts licking your folds. You moan around him, your mind consumed with the pleasure of him making out with your pussy.

You force yourself further down on his cock, the salty pre-cum taste on your tongue. His tip hits the back of your throat; gag reflexes triggering slightly. He was big, so it was a bit struggling to fit him entirely into your mouth.

“Taking it like a good girl, huh?” He manages to groan out, his breath fanning our pussy.

You just moan against his length; starting to bop your head up and down along it, occasionally sucking or biting. Your hand goes to massage his balls; which causes him to moan loudly. Shit. That motivates you to continue massaging his balls, knowing now that it’s what he likes.

He moans against you, while his tongue keeps thrusting itself into your pussy. Fuck, this all felt…so surreal. Is one even able to feel so much pleasure at once, just through oral sex?

The room is now just the sounds of the two of you, moaning and grunting, the bed slightly shaking.

You feel yourself coming close, as Drew continues to make out with your pussy. “Fuck…I’m close, Drew,” you breathe out, bopping your head slower now.

“I’know,” he murmurs, his tongue going slower too. “Just, continue with that, ‘kay?”

A sudden slap to your ass causes you to moan out of surprise, but also a reminder for you to continue wrapping your lips around his dick.

You do so; but only about half-way. With your orgasm coming close, your mouth was close to giving up. Eventually, you pull your mouth entirely away from Drew, wanting to focus on your orgasm.

“Fuck,” he groans, and just when you get ready to come over his mouth, his tongue stops, and you don’t feel his head nuzzled in your ass anymore. You glance back, curious as to what happened. His grip on your thighs loosens, but still resting there. “Lemme take over, yeah?”

You had no idea what that meant. But, you don’t object to it, nodding your head.

In a second, he lifts you off of him, and gets off from his comfortable position on the bed. “You got a condom?” He asks, standing up.

“In my purse,” you point over to the black bag on the small kitchen counter; the one you brought to dinner.

He gives you a teasing smile, while he walks over to get it. “So you knew you were getting laid tonight.”

Well, you always needed to be prepared, right? You lay yourself on the same spot Drew was just in, warm and smelling just like Drew. You prop yourself up with your elbows; eyes looking at his back as he rummages through your bag. He has a nice ass, by the way. “Couldn’t hurt to have it,” you reply lazily.

He turns around with a condom, ripping it open as he walks back to the bed. You watch as he positions himself between your legs, wrapping the condom around his dick.

He leans forward and kisses you, a very sloppy kiss.

You’re taken by surprise when his fingers enter you; causing you to moan into his mouth. “Fuck,” he curses against your lips, his fingers thrusting in. He adds a third digit, which is close to sending you over the edge.

He stretches you out, while his lips now move to your breasts. You arch your back in pleasure, moans showing him how good it felt.

His fingers pull out, and you watch as he aligns his dick with your entrance. Fuck, no matter how many times you see him, it’ll always shock you with how big he is.

You make eye contact with him, which makes him send you a lazy smile. “You good?” Teasing but also caring is heard in his voice.

“Will…I fit?” you ask unsurely.

He chuckles, placing a small kiss on your jawline. “Don’t worry; you’ll fit. And it’ll feel good.”

You nod, trusting him.

He enters you slowly, making sure you can adjust to his size. You moan when his dick is fully nested inside of you, your hands scratching his back. He leans his forehead gently against yours; the both of you catching your breaths.

He feels you relax under him, and intertwines his fingers with yours. His head pulls away, and for a few seconds, it’s just him staring at your face. You watch as his eyes linger to every spot on your face.

“Hey,” you softly say, which comes out more flirtatious.

“Hey,” he returns the greeting to you, sounding breathless. “You’re pretty.”

That makes you smile, and you pull him back down to kiss him. He kisses back, while thrusting into your core. You moan, even though his thrusts were slow.

“Faster,” you moan.

“Yes ma’am.”

Hot. Hot. Hot. Hot. The way his deep voice adds to that line, gets your pussy closer to coming. And a man of his words, he picks up the pace, slamming into you.

The bed shakes even harder now, the moans the two of you produce are shamelessly loud. He trails small kisses along your neck, sucking occasionally.

And as crazy as this thought was; you knew Drew was going to be the best sex you’ve ever had. Might even be better than the night you lost your virginity. He knows all the ways to feel good, to make you feel good.

With each thrust, you feel yourself coming close again. “Shit, Drew. I’m close,” you groan, tightening yourself around his dick.

“I’know babe,” he kisses the corner of your eye. “Cum on my dick; I got you.”

He continues his fast pace, hitting your g-spot repeatedly, until you feel a knot in your stomach go undone.

You cum all over his dick, your body giving up now. Drew helps himself, and you feel him twitch inside of you too. His pacing slows, and you feel warm cum entering his condom.

“…You squirted,” you hear him chuckle, as he rests his head on your shoulder.

Oh shit. How embarrassing. You didn't know you were even capable of squirting. Is Drew grossed out by that? Based on his tone, he might not be, but then again-

“That’s…really fucking hot.”

You feel your cheeks go red just because of his compliment, letting go of his hands. You cover your face out of shyness, “shut up.”

You hear him chuckle again, “really…you’re very hot. And beautiful.”

He holds down on your waist as he slowly pulls out of you. You hear him walking across the room; probably to discard his condom. The warmth of him is gone; but a dip on the side of you tells you that he’s laid down on the bed with you.

This man was unbelievable. First, he shamelessly looks at you during dinner, not engaging in any way with you. Second, he comes into your room in the middle of the night, claiming he’s got ‘important’ stuff to tell you. Third, he listens to long, boring stories about your life. Fourth, he fucks you so good you squirt.

Unbelievable.

You pull your hands away from your face, and you turn to face him. He’s already staring at you, his arms resting behind his head.

The two of you just lay in silence; your eyes dancing all over his facial features. He really does look like the guy you lost your virginity to. Same face, same eyes, nose, lips. The resemblance is…uncanny.

“You…” you want to ask him if he’s Drew. The Drew from four years ago.

But you don’t. For some reason, you just can’t. You can’t bring yourself to ask him.

It was a horrible memory; crying at home for days, just because he rejected you. Crying over a guy that you weren’t even together with. It was a stupid memory, that you kept deep in your heart. Eventually, that memory was pushed to the very back with Zack’s help.

“…we just did 69,” you say instead.

That makes him laugh; sending butterflies to your stomach. “Yeah, we did.”

You’re feeling a bit sleepy now; the tiredness of the sex washing over you. Drew suddenly gets up, and for a moment you think that he’s leaving.

But he wasn’t; simply grabbing some tissues on the coffee table. He spreads your legs, and starts wiping the cum off it. “What a gentleman,” you sarcastically comment, even though you were happy he’s cleaning up after; Zack never does.

“The bare minimum, y/n,” he tells you instead, before getting off the bed again, throwing it away.

Huh. You didn’t know; you’ve ever only been with Zack.

He lays down beside you again, but not before pulling the blanket over you. “Tired?”

“Very,” you murmur, your eyelids feeling heavy. You don’t know why you said it, but you just did, “you can stay here.”

“Wasn’t gonna leave anyways,” he replies back almost instantly.

Warmth spreads throughout you, the comfort of Drew just laying beside you was enough to make you fall asleep.

And you do drift off to sleep, with the last thing on your mind being Drew.

Soon enough, Drew falls asleep too, but not before hugging you closely to him.

-------------------------------

  • word count: 6.8k

ִ ࣪𖤐 a/n: damn they freaky (69 after four years...freaky bitches)

anyways, this is the longest chapter i've so far ...but i hope you enjoyed part three (there will be part 4!) ignore any mistakes...got real tired towards the end. i want to thank everyone who reads my work, u don't know but means a lot to me<3 also thanks to the person that also thought of the time skip idea...tysm! so...will y/n and drew open up about the past? and... who's zack👀👀

#drew starkey imagine | chleem (2025)
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