The Catch-Up Ch. 09 - Summer's End

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A quiet nerd goes on his first date ever as summer ends.
14.4k words
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Part 9 of the 9 part series

Updated 06/15/2023
Created 03/01/2020
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Disclaimer: All characters are 18 or older.

Author's Note: Hi, I'm alive, thanks for your patience. I'm back to finish the Catch-Up! Hope you enjoy the last chapter, I know it's been a long time coming.

As I said before, I may write some one-offs or a sequel about AJ and friends, but I have ideas for other multi-chapter stories, like a college or post-college story with a different main character and cast. Bear in mind that I only have so much time for writing, and any future updates may be inconsistent, although hopefully not as bad I've been with this last chapter.

Always love reading your comments, favourite characters, and what you might like to read. Thanks for reading!

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 the small high school he just graduated from.

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.

DYLAN: Track and volleyball star, another friend of Mackenzie's. Very tall (around 5'11") with long legs, slender except for her round, volleyball player butt. Very short, platinum blonde hair and hazel eyes.

AMANDA: Part of AJ's friend group since the start of high school. A Mormon and star soccer player with very religious parents. Tall and athletic, with curly brown hair cut above the shoulders and brown eyes.

EVA: Reagan's friend, another Junior who's on the Pom Team. Half-Egyptian, with long, dark hair and a fit, petite body. Watched, but didn't participate in AJ's first blowjob from Reagan.

REAGAN: Grant's ex-girlfriend, a Junior who had an encounter with AJ on the last day of school. Petite, with brown hair in a retro bob and dark blue eyes.

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.

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

GRANT: AJ's best male friend, who often overshadows him without meaning to.

* * *

"WOO! SUCK IT, BITCHES!" Bridget shouted, throwing her controller aloft.

"Oh, crap on a cracker, I was so close!" Amanda slapped her leg.

"God damn it...." Grant grumbled.

"I'm in seventh, this is bullshit--" Paige complained.

The outrage continued as the Mario Kart victory fanfare played throughout Rani's living room.

"Guys, look who's finally here..." Rani said in her quiet voice from next to me, pushing up her big coke bottle glasses.

I gave a weak wave from the doorway, putting down my overnight bag, as my friends turned to see me.

"Hey dude, can you finally beat Bridget, because she's starting to get annoying..."

Grant said. Bridget kicked him from up on the couch.

"Yeah, fat fucking chance, scrubs." She tossed a pretzel into her mouth, before looking at me. "Where the hell were you?"

"College stuff..." I sighed. "Sorry."

"You're so brown!" Paige said, looking at me carefully. "Or... browner."

I don't sunburn easily, but after the long, long walk home, my tan from camp had taken on a reddish, crispy tint. "Yeah--camp," I said, quickly, stepping down into the living room and plopping myself on the couch between Amanda and Bridget.

"One more Cup, losers?" Bridget waggled her controller temptingly.

"I'm out. AJ, you play for me..." Grant passed me his controller and lay back on the carpet, stretching out his long frame.

I tossed it to Rani. "Rani, can you shut her up, please?"

Kneeling on the carpet, Rani took the controller in both hands and flicked her bowlcut bangs out of her eyes. "Okay. I'll do my best." If there was anyone who could beat Bridget at Mario Kart, it would be Rani.

Bridget narrowed her eyes, turning her five-panel cap backwards. "That's how it's gonna be, huh? Just so you know, I'm on the streak of my life."

"Hot-Hand Fallacy..." Rani murmured, peering up at the screen and selecting her racer.

In the hubbub, I glanced towards Amanda next to me. "Hey."

Having already picked Yoshi, she shot me a shy smile, a secret spark in her bright brown eyes. "Hi. Glad you made it." Her brown curls were pulled back into a bouncy, messy bun, and she wore a Raptors jersey and boyfriend jeans in what was a slightly trendier outfit than normal.

"Me too..." I grinned and casually bumped her thigh with mine, reclining and running a hand through my hair. Between the walk and my parents cornering me when I got home to prep for college, it had been a busy, stressful day, but there was nowhere I'd rather be than in a room with my friends, a big screen TV and a bunch of junk food.

This sleepover was our last hurrah before we all went our separate ways, and we were determined to make it a good one. Rani's parents were out of town, and the pizza and wings arrived soon after I did, so we moved out into the backyard to eat.

"So how was camp?" Paige asked. "We missed you guys!"

"Awesome, like always. Kinda sad it's over, but I missed you guys, too," Amanda said, putting her chin in her hand, and raising her eyebrows. "AJ had a really great time."

Mouth full, Bridget narrowed her eyes, wing sauce all over her hands. "Wait--what does that mean?"

"Well... he kinda had a camp girlfriend..." Amanda grinned.

"Okay, I did not..." I butted in, surprised and flustered that Amanda was bringing it up. If she was jealous of Dylan, it clearly didn't bother her enough to stop her from embarrassing me.

"What? Who?" Paige asked, mouth dropping open.

"Dylan Nystrom..." Amanda said eagerly.

There was a round of shocked exclamations. Even Rani's eyes widened. I reached into my cup to throw a few melting ice cubes at Amanda, who ducked with a shriek and a giggle.

"Fuck, seriously... she's so hot." Bridget groaned, leaning back in her chair, staring up at the sky in exasperation. "Please tell me you didn't actually hook up..."

Paige snorted. "Of course not. AJ doesn't hook up..."

Between Amanda, Bridget and I, there was enough noticeable quiet and avoided eye contact to speak volumes.

Paige frowned, gaze flicking quickly between us before she looked right at me. "But... you didn't... did you?"

I probably could have lied convincingly, but for some reason I just shrugged.

"Maybe I don't kiss and tell."

"Boo. Lame." Bridget balled up her napkin sulkily, while Paige continued to stare at me. Grant just laughed.

"Come on, guys, it's his business." He caught my eye. "Dylan's... really cool, though."

I nodded. "Yup, she is." Under the table and out of sight, I felt a hand on my leg, and glanced over at Amanda briefly, keeping a straight face. "But there was a lot of cool people at camp."

With a pleased little toss of her head, Amanda gave my thigh an approving squeeze and went back to her pizza before anyone could notice.

After dinner, Bridget uncharacteristically volunteered to go get more snacks for the movie. "AJ, get your ass up. And you're buying, 'cause you were late."

Almost as soon as we were out the door, Bridget demanded details, as I'd expected. I'd texted her about Gigi, but I updated her about Dylan and Eva, too, although I left Amanda out of the equation. She had the most to lose should this get out, and given that we'd be hanging out with her until the next morning, I wasn't sure if I trusted Bridget to keep her cool.

Bridget had heard enough about my spectacular luck that her only reaction was to shake her head and kick at some dandelions with her sneaker. "Man... I gotta go to summer camp. Clearly, you need some competition."

"Well, you'll have the whole town to yourself in a few days," I laughed. "All those community college girls..."

"Do people even fuck at a commuter school?" Bridget grumbled. "Although..." She caught my eye. "That one chaperone from Mexico goes there."

"Zara?" I grinned at Bridget's feigned nonchalance. "Have you guys been texting?"

Bridget fidgeted with her cap, hunching her shoulders. "On and off... I don't know if she's even into it."

"I'm sure it'll be different when you see each other in person," I reassured her.

Bridget nodded, looking a little more hopeful, and gave me a sideways glance. "It's wild that all you guys are gonna be gone..."

My heart sank a little, but I put on a brave face. "Yeah. Don't get sappy..."

"Oh, fuck you..." She snorted, flicking me on the arm with two fingers. "I'm not sad, I'm pissed. I'm gonna have literally no friends in the city except Sadie."

"Yeah..." Somehow the fact that it was Sadie and Bridget staying behind made things even harder. "We'll be back for Thanksgiving and Christmas. Probably next summer, too."

Bridget looked down, shoving her hands in her pockets, quiet for a long moment. "I swear to god... if I haven't caught up on your body count by then..."

I burst out laughing.

"I'm so serious, man--" she said, but she was smiling too.

After the movie, sprawled out on the living room furniture beneath blankets, we all started to get pretty sappy, reminiscing about high school embarrassments, awkwardness, good times and bad. Merciless teasing and sincere declarations of friendship flew around the room in equal measure.

It did feel a bit strange that Paige, Rani, and Grant had very little idea of what I'd experienced this summer, although I thought they could tell something had changed with me. Maybe I'd tell them sometime, maybe I wouldn't.

Between work and my misadventures, we'd found a decent amount of time to hang out as a group this summer, but I did feel like we'd already started to drift apart. In high school, I'd hung out with Paige and Grant one-on-one on an almost weekly basis, but since graduation I'd only really kept that up with Bridget.

Maybe it was just as well. With all of us scattering around the country, I knew it was something of an inevitability that we wouldn't be a friend group the way we used to. But they'd been there for me through the strangest, hardest, and best four years of my life, and I'd always love them for it.

Pretty soon we all passed out in sleeping bags in the living room, spread around the floor and couches amidst the wreckage of chip bags, popcorn bowls and empty pop bottles. In the morning, I woke up with a text.

SADIE: When do you leave again??

AJ: Wednesday!

SADIE: Wanna take me out tonight

I swallowed.

AJ: Like on a date??

SADIE: Yeah dummy like on a date

I pressed my face into my pillow to hide my smile.

AJ: I'd love to

SADIE: Cooool pick me up at like 8

SADIE: I'm making a reservation

Even after everything I'd experienced this summer, the idea of going on my first date ever tonight, with Sadie, no less, made my stomach feel like it was full of pop rocks. All I could do was try to hide my nervous, excited fidgeting from the others as they all woke up one by one, sporting emotional and junk food hangovers.

My friends and I didn't worry too much about goodbyes, since we knew we'd be seeing Paige, Rani and Grant off at the airport tomorrow. Amanda gave me an extra tight hug and a kiss on the cheek when no one was looking.

"Thanks again, AJ..." She held my gaze, only blushing a little.

"Thanks? I should be thanking you..." I said in a low voice, glancing over at the others giving hugs in the hallway. "It was really awesome..."

"Yeah, it was." She gave a nervous laugh through her nose. "I kind of... feel like a new person, y'know?"

"Yeah, I know what you mean. It's the best, isn't it?"

She nodded, grinning and gave my hand a squeeze.

I spent the afternoon trying to get ready for my date while fighting off my parents' badgering about what else I needed to get done before leaving for uni. Eventually, I just shut myself in the bathroom for a long shower and some "manscaping", which I was still relatively novice at. With the help of the internet and some very careful use of clippers and a safety razor, I felt ready for whatever awaited me.

I paced around my room with a towel wrapped around me, before remembering to put a bit of product in my hair while it was still damp. I must have gone through four or five outfit changes before I finally settled on black chinos, my cleanest pair of sneakers, and my one "fancy" shirt, a dark red, floral-patterned button-down that I'd never felt quite comfortable in.

I was going to wear contacts, but I had so much nervous energy I blinked them out and poked myself in the eye a few times, so I figured I'd better stick with glasses. Otherwise, I might look I'd been smoking some of Bridget's premium skunk before picking Sadie up.

At 7:40, I sighed at myself in the mirror and ran a hand through my hair for the umpteenth time. This was Sadie, I kept trying to remind myself. We were friends--she didn't care that I looked like a dork. I'd seen her naked, fucked her in public and come inside her, for god's sake.

I repeated that in my mind like a mantra as I walked to my parents' car, but it was still my first date ever, and I was jittery the entire drive over, drumming on the steering wheel.

AJ: Here!!

I got out of the car just as Sadie's front door opened and she stepped out, laughing.

"Oh my god, were you gonna walk me from my door? It's not 1955, AJ!"

I didn't respond at first because I was too busy staring. Sadie was wearing a pastel pink minidress that was practically painted onto her full, sweeping curves, the halter-style bodice tight around her throat and struggling to contain her chest. I'd heard of the "legs or boobs" rule when it came to dresses, but Sadie was so busty that her tits would stretch any top to the limit, so apparently, she had decided to embrace it.

A circular window in the dress let a shelf of creamy, squeezed-together cleavage spill free, swaying as she clacked down the front walk in tall, white high-heels, purse on her shoulder. Her golden-blonde hair was half-up in a knot on top of her head, the rest in loose waves.

"...Hi." She looked up at me, all big, sea-green eyes and candy pink gloss on her full lips.

"Hi..." I croaked. "You look great."

"Thanks!" She grinned, crinkling her nose, looking me up and down. "You're not so bad yourself. C'mon, let's go."

"Yup." I turned and opened the passenger side door for her with an exaggerated flourish.

Sadie snorted, climbing in. "Well, golly gee, I guess chivalry isn't dead."

I laughed, practically sprinting around to the driver's side door. How the fuck did I get so lucky?

"Where are we going?" I asked, putting the car in drive.

"Vin's," Sadie said. "It's your first date, right? Figured we should go with a classic."

I couldn't stop grinning like an idiot. "Cool..."

She settled back into the passenger seat, and I tried not to get distracted at how her dress rode up her thick thighs. "So... how was camp?"

"Um..." I told her all the non-juicy stuff easily and quickly. Sadie knew I'd already slept with other people this summer, but I still wasn't sure how we were navigating talking about it. I danced around it a little, but I could tell she knew something was up.

"...That's it?" She was side-eyeing me hard, playing with the hem of her dress.

"What... what have you heard?"

Her face split into a mischievous smile. "I heard you played sex-ed teacher. And track coach."

I stared at the road, blushing hard. "Word really gets around, huh?"

"Yeah, well, people have big mouths." She ran her tongue across her teeth. "As you're well aware..."

I huffed out a laugh, shaking my head.

"You are such a fucking slut..." Sadie smirked, biting her lip. "Welcome to the club."

Vin's wasn't the fanciest place in the city, but it was the kind of place that made you feel like you should put some effort in. It was a local chain, but skewed classier than a standard bar and grill. Dimmed down lighting, no TVs, servers in tight black dresses, serving thin crust pizzas and a burger that cost twenty bucks, that kind of thing.

As our hostess led us to our table, I felt my spine get a little straighter, my shoulders squaring as I walked through the restaurant behind Sadie, even putting a hand lightly on her lower back. She was my date, and anyone looking over knew it.

The table was at a full, black leather booth that curved around in a U-shape. I slipped into the side facing away from the door. "Big table. We must have got lucky."

"Yeah, I guess so." Sadie shrugged, a smile still playing at her lips. "God damn, I wish we could get drinks. I highly doubt my fake would work here."

"Your cousin's old license? Does that work anywhere? She's like twenty-five," I laughed.

Sadie's mouth dropped open in mock-offense. "It's worked plenty of times, thank you--at shows, at the bar... even the liquor store, a couple times. What, you don't think I look twenty-five?"

"I guess so... maybe the hostess thought you were my babysitter." I pushed up my glasses, still a little stiff in my fancy shirt.

"Ooh. Kinky," Sadie said, resting her chin on her fist. "Want me to take care of you, baby boy?"

"Shut up." I snorted with laughter, going red, and Sadie giggled.

"Honestly..." She ran a hand through her hair, seeming to consider it. "...Kinda hot.

"

Looking across the table at her, her eyes dancing and expression teasing in the soft light, I had a feeling this was going to be one of the best nights of my life.

"Hi, there." Our server appeared, college-aged and intimidatingly pretty, with sleek strands of brown hair coming out of her tight bun to frame her face. "I'm Peyton, I'll be taking care of you guys tonight." She placed menus in front of Sadie and I, and then two more on the empty tabletop next to us. "Still waiting on someone, right?"

"Oh, um, not... no..." I started to say, frowning.

"No?" Peyton raised her eyebrows, pausing.

"Not anymore..." Sadie flashed a dazzling smile over Peyton's shoulder.

I turned to see a very tall girl with very short, ash-blonde hair making her way towards our table. The high-heels of her black, over the knee boots put her over six feet, easily, further elongating her already towering legs. They drew the eye all the way up her sleek, slender figure, in a clinging black skirt and a thin white blouse with the collar open and a few buttons undone to bare her collarbone. She wore simple earrings, a black, 90s style choker, and dark pink lipstick.

I'd never seen Dylan Nystrom look quite like this.

"Hey. Sorry, I'm late..." A small smile played at her lips as she put her clutch down on the table and slid into the booth next to me. Somehow she still smelled like pine needles, along with a woody, almost musky perfume--sandalwood and sage. As I sat there, still in shock, she picked up the menu. "What looks good?"

"Besides you?" Sadie grinned and Dylan waved it aside with a hand.

"Um..." I said, still staring at her with a stupid look on my face.

"I'll... let you three have a look at those menus, then. Let me know if you have any questions." Peyton gave Dylan the up-down, eyebrows raised, and then left with a smile.

"Hi--Dylan, hi... what... what's happening?" I finally got out after she'd left.

"I'm... here for our date. I know you didn't technically ask me, but..." She rested her chin in her hand. "I texted Sadie yesterday to apologize for the whole camp thing... taking her name in vain. And it came up that you've never been on a date, so... instead of fighting over who would ask you first, we thought maybe you should just take us both out." She and Sadie shared a smirk. "If that's cool with you, obviously..."

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