The Catch-Up Ch. 06

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A shy nerd gets caught up in the drama of two popular girls.
9.7k words
4.78
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Part 6 of the 9 part series

Updated 06/15/2023
Created 03/01/2020
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starcall
starcall
884 Followers

Disclaimer: All characters are 18 or older.

.Author's Note: Sorry about the wait, I was a little stuck on some things and I got distracted with other writing. Also a shorter chapter, because it's mostly sex! As an FYI so no one is disappointed, this not really a threesome chapter. There will be M/F/F chapters in this story but I'd like to draw out AJ's milestones a bit more. Stay tuned.

As always, I really love the feedback, glad you're all still reading. I do actually take into account which girls and storylines people are excited about, so keep them coming.

CAST LIST

New characters are added after their first chapter. I've decided to pair down the cast list to characters that are mentioned/relevant to the current chapter.

AJ: Our protagonist, a quiet, nerdy, guy, but nice and well-liked at his small high school.

BRIDGET: A sardonic, tomboy friend of AJ's who's gay and a bit of a stoner. Messy tawny hair, usually under a beanie or baseball cap, hazel eyes, and a more feminine figure than she lets on.

SADIE: A newer friend of the group, rumoured around school to be a bit of a slut. Short, curvy and famously busty, with long blonde hair and bright blue-green eyes. Loud, bubbly, and a little wild.

MACKENZIE: The most popular girl in school and captain of the pom team, who AJ lost his virginity to on prom night. Slender and fit, with sleek, brown to blonde ombre hair, big blue-gray eyes, and oh-so-perfect, "Disney princess" features.

GIGI: A wealthy, glamorous and intimidating member of the pom team and friend of Mackenzie's. Wavy black hair, bronzed light brown skin, catlike amber eyes and full, sensuous features. She's Brazillian/Colombian, tall, toned and curvy.

KIERA: AJ's coworker at Daisy Dairy ice cream, who's a year older than him with a dry, sardonic sense of humour. Petite with reddish brown hair, girl-next-door good looks.

PAIGE: AJ's best friend since middle school, who used to have a crush on him, although he only liked her as a friend. Curly auburn hair, big brown eyes, a little chubby. Sweet, smart, and sensible.

AMANDA: Part of AJ's friend group since the start of high school. A Mormon and star soccer player with very religious parents.

RANI: A very shy, awkward friend of AJ's.

***

AJ: How's your shift going??

SADIE: It's fineee I guess

The text was followed by a selfie of Sadie in her black hostess outfit, winking and sticking out her tongue playfully. Her hair was pulled back into a stylish bun and she wore a simple black skirt, black pantyhose, heels, and a black turtleneck that clung to her amply curving chest.

AJ: at least you look amazing

SADIE: thx babe <3

SADIE: Everyone is clowning me for wearing a turtleneck in the summer but someone left hickeys on my tits soo

AJ: Oops sorry I'll be more careful next time

SADIE: LOL it's fine

SADIE: Tbh I actually got kinda wet looking in the mirror this morning...

"Okay. That's it. Your phone is going in the milkshake machine."

I hurriedly glanced up, remembering I was supposed to be working. Kiera was staring me down, hands on her hips.

"Sorry, sorry, sorry—" I went to put my phone away but she darted forward.

"I'm serious. We've got six tubs of ice cream to scoop and you're smiling at your phone every five minutes." She made a grab for it and I held it behind my back.

"I wasn't smiling at my phone!"

"Dude--you literally are, constantly. Your perky attitude today is pissing me off." Kiera tried to duck around me, but I boxed her out like a basketball player as her petite body bumped into me. "Give it!" Her grumpy façade was starting to slip—I could hear the grin in her voice as we scuffled in the back of the ice cream shop.

Being nearly a head taller than her, I extended my arm and held my phone up high, far out of her reach. "Oooh. What now?"

Kiera scowled, crossing her arms, then nut-tapped me with the back of her hand.

It was a light tap, but I still yelped, hunching over briefly as pain spider-webbed out from my crotch. "Urgh... Fuck..." I groaned, teeth clenched. "...Sexual harassment. That's workplace sexual harassment."

"Start scooping or I'll show you sexual harassment." Smirking, Kiera turned on her heel towards the walk-in freezer, candy striped skirt swishing around her legs.

"...Weird threat." With her back turned, I rubbed my still slightly tender privates, sliding my phone in my pocket.

"I'm weird," she said evenly. "Anyway, tell your girlfriend to stop texting you at work."

"She's not my girlfriend..." I stammered. I suppose it was no surprise that Kiera had noticed the spring in my step today, but I couldn't restrain the excitement that still coursed through me from last night, though I was still a little sleepy—Sadie and I had been in that parking lot until around two in the morning.

We'd talked for a while, and made out for longer, but soon one thing had led to another and she'd ended up straddling me again, her curvaceous body riding my cock until another quick orgasm had shuddered through her, and she'd crawled between my legs to continue the en route blowjob until I shot my final load all over her huge tits.

"If she's not your girlfriend, you should have no problem ignoring her until your shift is over," Kiera said dryly, closing the freezer door with a thud.

Sighing, I satisfied myself with memories of the glorious night before as I scooped ice cream until my arm ached.

Unfortunately, I had to make do with that for the rest of the week, as Sadie was busy with work, picking up a couple of double shifts at the restaurant, and annoyingly, I had to help my parents remodel our kitchen when I wasn't scooping ice cream at Daisy Dairy.

I was exhausted by the time I left work on Friday, and frustrated at missing Sadie. I ended up staying up late, sunk deep into the couch, a kung fu movie on and a mostly empty bowl of popcorn in my lap when I heard my phone buzz.

My heart jumped, and I groped around for it, already imagining the text from Sadie, saying that her evening had finally opened up, but instead it was a Facebook message.

MACKENZIE: Hey

MACKENZIE: I need a rkde homee

MACKENZIE: *ride

I frowned. It was after midnight.

AJ: Was this meant for me??

MACKENZIE: yes obviously

AJ: You want me to pick you up

MACKENZIE: come on i rellaly need ka ride home

MACKENZIE: 1226 baycrest bae here in 10

1226 Baycrest was Gigi's house.

I groaned, rubbing my forehead. Mackenzie was almost definitely drunk, presumably at a party at Gigi's. Why on earth she'd ask me for a ride, I had no idea. Unless...

Trying to clear my head, I made a quick mental list of pros and cons of picking her up.

Cons: Validating Mackenzie's bossy and entitled attitude, getting up from this comfy couch, possibly having to face Gigi.

Pros: This could be a booty call. She could also be in trouble and actually need a ride.

Who was I kidding? Now that she had asked me for a ride home late at night, I would feel like a real asshole if I didn't go and something bad happened to her.

With a heavy sigh, I grabbed the keys to my parents' car and pulled on my sneakers.

Ten minutes later, I was outside Gigi's massive Mediterranean-style mansion again, wishing Sadie was beside me again. I could hear the hip-hop blasting from here—clearly a large party was happening inside.

I texted Mackenzie as I pulled up, hoping she'd come out to the street, and I could avoid interacting with the hostess at all costs. Gigi didn't know it was me that had blown her off, but I wasn't sure I'd be able to look her in the eye after everything.

MACKENZIE: Come inside I'll meet you

I rested my forehead on the steering wheel and sighed heavily before forcing myself to get out.

Gigi's place was just as insane on the inside, huge, impressive, and flashy—the house of people who wanted you to know how rich they were. I wondered if Gigi's parents knew she was throwing herself a party here that would be better suited for a frat house.

The stereo system in Gigi's house pumped music into every room and from further inside I saw strobe lights throwing dappled spots of colour into the hall, heard whooping laughter and loud conversation. Through the back windows, I could see the pool lit from below, and teens splashing around, drinking on the deck.

"Honestly, I'm so fucking over it, okay? Soooo over all of your bullshit..." Coming from down the hall was Mackenzie's voice, slurring slightly, obviously as drunk as her texts had let on.

"Oh yeah, you seem so over it." That was Gigi, oozing with sarcasm. In a moment of panic, I hurriedly opened a nearby door and took a step into what looked like a study or home office, leaving it open a crack. "You know, maybe he would have actually picked you if you weren't such a whiny little princess..."

Mackenzie let out an indignant scoff. "Oh, fuck you."

"...You're sloppy. Go home, bitch," Gigi snapped, and I heard her turn and storm off.

I ducked my head out to see Mackenzie in the foyer. She was wearing that same blood-orange one-piece swimsuit from Mexico, the strappy one with the cut-outs, but her long, ombre hair was dry, parted and loose in a sleek curtain.

"Slut..." She muttered, glowering in the direction of Gigi's exit. She had a drink in her hand, not that it looked like she needed any more. She turned, spotted me, and her eyes narrowed.

"Hey. I was just... waiting for you." I stepped awkwardly out of my hiding place. "Ready to go?"

Slightly unsteady on her feet, she marched straight at me, grabbed me by the wrist and pulled me into the study, yanking the door shut behind us. I caught a big whiff of her familiar perfume and the smell of alcohol.

"Wait, wait, wait, Mackenzie..." I pulled free of her, back-pedaling as she turned and came towards me, advancing until my legs hit a leather armchair. "You're pretty drunk, right?"

Hands on my chest, Mackenzie pushed me back into the chair, moving with a single-minded, drunken determination, her only response to press her Solo cup into my hand with a quirk of her eyebrow. Then she lowered herself to her knees and started unzipping my jeans.

It had been such a frustrating week that there was already a thick bulge in my boxer briefs, and I breathed in sharply as her lips pressed it, my cockhead actually starting to peek out of the waistband as I hardened.

"Hold on, hold on..." It was hard to think clearly. She was definitely drunk and I wasn't, did that make this automatically wrong? She wasn't incapacitated and she was definitely initiating. Who was really taking advantage of who here?

Suckling at my underwear-clad shaft, dampening the tight cotton with her saliva, Mackenzie reached into the pocket of my jeans and pulled out my phone, swiped at the screen a little clumsily and passed it to me.

It was on the camera, recording a video. Currently, of my covered erection resting against her gorgeous face.

"What the fuck..." I whispered, barely audible. "Are you sure?"

Staring up into the camera, Mackenzie nodded, parted lips casually rubbing at the tent in my underwear. Swallowing, I pointed the camera down at her, the video still rolling.

With her small hands, Mackenzie peeled down my boxer briefs, my tawny, straining cock bobbing free to smack against her cheek. Then it was in her mouth.

Looking down my length, shaded behind her long lashes, she immediately hollowed her soft cheeks and sucked, exhaling through her nose, her breath tickling my taut shaft. I made a noise in my throat and stared at the image being recorded on my phone—my cock disappearing past Mackenzie Taylor's bowed lips as she worked them up and down, slowly, lingering on the swollen head to suckle and swirl her tongue around it.

Somehow seeing it on the phone screen made it feel more real than ever before.

With a soft spitting sound, she released a mouthful of drool onto my crown, spreading it down my shaft with her hand, and glanced up, first at me, then moving to the phone's camera, her gaze meeting mine through the screen.

"Fuck..." I mouthed, almost unconsciously taking a sip from the Solo cup she'd passed me, a strong and sweet mixed drink. Mackenzie's doe eyes stayed on the camera as she dragged her pursed lips up and down my length, bathing my shaft in long, ice-cream cone licks, before swallowing me again. She was performing, flicking her tongue feverishly, passionately push-pulling my cock with both hands.

Mackenzie pulled off my dick with a wet pop, big blue-grey eyes hazy and half-lidded as she fisted my shaft, giving my cockhead a messy tongue-bath. Thanks to the booze and maybe the camera too, she was like a different person, bolder and filthier than I'd ever seen her.

"Unh..." I groaned, guiding her back down, pushing to rhythmically bob her head on my cock. It was nowhere near as rough as the mile high face-fuck, but I kept my grip tight in her hair the way I remembered she liked it, making sure my cock plunged a little into her tight throat with every swallow.

Mackenzie let out a muffled moan, diligently gulping my shaft, lips tight and sucking. She fidgeted on her knees, squeezing her thighs together, crossing one ankle over the other.

Groaning, I let go of her hair and bent over to grab a handful of her round ass where the curve of her cheeks escaped the bottom of her swimsuit. She squirmed, desperate sighs squeaking out around my shaft and all on her own, her head bounced, slurping down my cock sloppier and deeper than ever.

Now her smacking lips, wet and shiny with pre-cum, lip gloss and saliva, brushed the base of my dick at the apex of each suck, her soft hands splaying on my thighs.

I had to bite my tongue to keep from moaning, tense my arm so the phone didn't shake, making sure to capture every second of Mackenzie fervently deepthroating my dick in crystal clear HD. Her eyelids fluttered, then snapped open, locking onto the camera, that deceptively innocent gaze wide and wanton as she gave a performance that would put a pornstar to shame.

Even stifled around my stuffing girth, her moans were loud as she tossed her head, vigorously fucking her mouth with my cock, filling the elegant study with thick, wet chokes. Spit rolled freely down my slick shaft as Mackenzie swallowed me hungrily, her stroking tongue squeezing between her bottom lip and my dick to bathe my length. She made sure I captured just how deep she could take it, plunging my cock all the way into her throat so her lips were planted on my balls, only pulling back when she gagged.

"Oh god..." I sucked in deep breaths, staring at my phone screen as Mackenzie made love to the camera with her eyes while doing the same to my cock with her lips, tongue, and throat. I'd seen her expressive face when she danced, hitting a new expression with each move, and this was much the same, eyes wide in begging submission, then narrowing, almost rolling back with slutty cock-hunger, before half-lidding behind her long lashes in a passionate smolder.

"Huhhh..." The tingling currents of orgasm bubbled up and this time I didn't even bother telling Mackenzie that I was going to come, just put a hand on her head and exploded in her engulfing mouth.

On the video, I saw her eyebrows go up, meeting, and she bobbed even faster, pumping out every throb with her hands and lips until it was spilling out of her mouth. As the pulses slowed, so did she, sucking the last few out with satisfaction, eyes lingering on the camera as she swallowed.

Groaning, I gave her an impulsive smack on the ass as the last spurt filled her mouth, and she gasped, giving me a glimpse of my white cream on her tongue before she gulped it down, stopping any more from running down her chin.

Just like last time, Mackenzie was a deliciously gratifying mess, flushed, chest heaving, hair askew and make-up smeared. Ensuring the video caught that perfect final frame, I hit stop. She held out a hand and I passed her the phone, gaping stupidly.

"What..." I panted, pushing up my glasses where they'd slipped down my nose. "What the hell was that?"

She wiped her chin with one delicate finger as she tapped on my phone with an air of drunken smugness.

"What are you doing with that..." My stomach knotted.

Mackenzie paused, but in her current state, she couldn't exactly keep a poker face. She flipped the phone around and showed me.

I froze as I saw Gigi's name at the top of the text thread. Below it was the thumbnail of Mackenzie's face and my cock, with two accompanying messages.

MACKENZIE: Found your mystery cock... I think he likes me ;)

MACKENZIE: Hope you like to watch bitch

"...Jesus fucking Christ. Why did you..." I grabbed the phone from her hand, but it was too late, the video, the texts, were off.

Suddenly it all clicked. "It was her, wasn't it? On prom night, with Tanner. Gigi." I'd wondered which one of Mackenzie's friends I'd heard fucking her prom date that night, but I hadn't been able to figure it out until now.

Mackenzie's Disney-princess eyes went cold. "Wow. Guess you actually are smart," she spoke finally, voice throaty with booze.

"So I'm your revenge. Again." I said as she got to her feet.

"Is that a problem?" She said without turning, as I watched the roll of her ass with every step.

I sighed. "Guess not."

"That's what I thought." Mackenzie paused with her hand on the doorknob. "Oh, and by the way, if I hear about you texting her again... I'll tell her who's been catfishing her this whole time, okay?" She smiled innocently. "If she finds out it was you... trust me, it is not going to be pretty."

I looked down at the floor, feeling the weight of the sneer in her voice when she'd said "you."

"Anyway, thanks for coming, but my Uber's on the way." With that she opened the door and padded barefoot out of the study.

Shame and resentment rushed in to fill the void of my short-lived burst of pleasure, and I just sat there, picking at the leather upholstery of what was probably Gigi's dad's chair.

The chair she'd probably recognize on video. Oh, shit. I had to leave.

I made it to the front door of the house before my phone buzzed. I was almost too afraid to look.

GIGI: What.The.Fuck.

GIGI: In my HOUSE you fucking slut you are so dead

I stepped outside into the relative quiet, cool shadows of her front step, before texting back.

UNKNOWN: She's gone. I'm sorry okay? I didn't know she was going to send it

UNKNOWN: This is between u and her

GIGI: Oh it's way too late for that, you fucking creep

UNKNOWN: I'm sorry but I don't know what you want me to do about it

There were a few long moments before it buzzed again.

GIGI: Upstairs, last door on the left

GIGI: Be there in 10 or I'll post your little movie online

I ran a hand through my hair, exhaling slowly, as I leaned back against the wall.

I had no idea what to do. Either way, I was screwed. It had been so stupid to anonymously text Gigi in the first place, and now I was going to pay for it. I'd probably end up forever branded as the creepy loser who catfished a popular girl into sending him nudes.

My friends would find out—Paige, Amanda, Rani, who knew nothing about this side of me. My parents might actually find out.

But if I didn't go, Gigi would leak the video, and that would be so much worse for Mackenzie than anything Gigi could say about me.

I really didn't have a choice. It was time to face the music. I was sick of the secrets and though it might destroy my reputation, telling Gigi the truth was the fastest way to end this.

starcall
starcall
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