The Catch-Up Ch. 04

Disclaimer: All characters are 18 or older.

Author's Note: Thank you for all the great comments and ratings, it really encourages me to keep going. Let me know which girls you'd like to see more of! I have some plans for future chapters, but everything is fluid. Also let me know what length of chapters you like, and how much story vs. sex you prefer.

CAST LIST

New characters are added after their first 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/Columbian, tall, toned and curvy.

FAITH: Mackenzie's close friend and teammate, only much sweeter. A cute, mixed Black girl with medium brown skin, who usually wears her dark hair natural and has a lean, fit figure.

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.

CHARLOTTE: Class president, bossy, ambitious and studious. Cute, with round, soft features and brown hair she always keeps pulled back. Short and thick, with surprising curves.

JULES: Julia, usually called Jules, is Sadie's best friend. She used to bully AJ in freshman year, but now they have a big sister/little brother relationship that's only a little condescending. She's tall and tanned, with a nose-ring, shoulder length honey-blonde hair and a strong, athletic body.

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.

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

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.

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.

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 Reagan and AJ's run-in.

ZARA: College student and orientation leader at Grad Trip. An edgy, punky girl with short, purple hair and a lot of tattoos. Bridget has a thing for her.

***

Sadie and I skinny-dipped in the ocean until the saltwater washed away all the sweat and stickiness from our encounter on the beach. I just kept staring at her bobbing naked in the water next to me, still not quite believing what had happened. It was one of the best nights ever, and I couldn't stop smiling.

It was late when we stumbled out of the ocean to reclaim our swimsuits and sneak back towards the cabanas.

"Sweet dreams. Thanks for the fuck." Under the overhanging of her cabana, Sadie gave me a big hug, wrapping her arms around my middle. "That was... actually crazy."

"...Anytime." I wanted to ask Sadie about where we stood—mostly if we could do that again sometime, but I bit my tongue. I also wanted to kiss her, but I hesitated on that too. It was Grad Trip, it had been spontaneous and insanely hot, and I didn't want to ruin that with an awkward moment. I could be chill. "This was a fucking awesome night."

She got up on her tiptoes and kissed me on the cheek, running her hand down my bare back. "...'Night, babe." Flashing me one last smile, she disappeared into her cabana.

The next day was pouring with rain, which meant that a bunch of us ended up in the girls' cabana—Sadie, Bridget, Jules, and a few more of their bunkmates from school. I guessed that Dylan, Faith, Gigi, and Mackenzie were similarly holed up elsewhere, probably a good thing if Sadie wanted to avoid questions about last night.

Some of the girls were bummed about missing the beach, but I enjoyed the relaxing day we spent chatting and playing Uno, listening to music from a Bluetooth speaker.

Sadie was her normal self, but Bridget seemed distracted, constantly going on her phone, hiding a smile. I bullied her into going with me on a run into the downpour to resupply on snacks and coolers, and as soon as I got her alone, I turned to her.

"So... who're you texting?"

"What? Nobody." She stuffed her phone in her pocket.

"Don't lie, you're shitty at it."

Bridget rolled her eyes. Around the side of the cabana, where Sadie and I had said goodnight, she pulled me aside. "Okay, but I'm only telling you because I need your help." She chewed her lip. "I've been texting with Zara."

I blinked. "Seriously? So she did reply."

"Yeah, eventually and somehow we started talking. Fuck, she's so cool..." Bridget said dreamily. "Anyway, she invited me to her cabana, so I need you to cover for me."

"Holy shit. Okay, sure. Good luck."

"I don't think..." Bridget shook her head, playing with her baseball cap. "...I think we're just friends."

I raised my eyebrows. "Okay... Whatever you say."

I dropped her off at orientation leader's cabana and when I got back to our classmates, I made something up about her feeling sick and going for a nap in my cabana. Sadie narrowed her eyes at this and I looked back at her innocently, pulling out my phone.

She glanced down at her own, reading my quick text about what was really going on and her eyes widened, looking thrilled. She texted back.

SADIE: HOLY SHIT..... go Bridget!!!!!

When evening rolled around, we had a slightly wet dinner at the resort's restaurant. "Don't you think we should check on Bridget?" Sadie asked me pointedly. "See if she's up to eating."

I shrugged. "Might be a good idea."

On the way to Zara's cabana, I hurried to catch up with Sadie, who was making a beeline through the rain. "Are we gonna be like... cramping her style or something?"

"I have to know what's going on with them.... Besides I'm so bored and I feel like they probably have weed. Come on." She yanked me towards Zara's cabana, around the side. One of the windows was open a crack and she got on her tiptoes, trying to peek in. "Ugh, I'm too short. C'mere," She whispered.

I walked up behind her and looked in, planning on only a quick look to see if they were in there, but what I saw made me pause.

On the bunk bed in full view of the window were Zara and Bridget, severely underdressed. The purple-haired orientation leader was wearing a sports bra, her bare leg drawn up on the bed, partially wrapped around Bridget, who was pulling her baggy t-shirt over her head. I saw my tomboyish friend's bare back and the side of her breast before she leaned back in and kissed Zara hard, the two girls entangling in a passionate embrace.

"What? What?" Sadie hissed, seeing the look on my face. I hurriedly yanked my head away from the window.

"They're hooking up..." I mouthed. Sadie's face lit up.

"Ugh! I can't believe I can't see!" She tried to peek in again. "You have to tell me what's going on."

"Sadie! We shouldn't watch."

"You didn't mind so much last night," She pointed out.

"Well, they're in private."

"I'll give you a blowjob." Sadie bit her lip.

"...Seriously?" I swallowed. I glanced back through the window and saw that Bridget was falling to her knees on the floor in front of the bed, pulling back her tangled, tawny hair as she buried her face between Zara's legs.

"Fuck, she's going down on her," I breathed. Zara who was now topless, tattoos exposed, toyed with her perky tits, nipples pierced by silver bars, throwing her head back and squeezing her thighs around Bridget's head. A soft, high moan floated through the open window. Bridget was going down on a college girl, and she was clearly doing a very good job.

I felt Sadie's hand start to rub me through the front of my khaki shorts, a tent already forming there. We were relatively hidden, the rain loud on the cabana roof, pouring from the overhang covering us.

On all fours, Bridget's ass, clad in tight, surprisingly feminine hipster-style panties, was thrust out towards me as she ate Zara's pussy, reaching up to fondle her tits at the same time.

"Mhm, that's good... right there... Ohhhh, shit..." Zara sighed, fingers knitting into Bridget's hair.

Sadie was undoing my fly, but I tore my eyes away from the sight in the cabana. "Let's go, Sadie. This is private." I knew if Bridget found out we had spied on her, we'd be in for a world of shit.

Sadie pouted. "Okay... fine." We snuck away, back towards our cabanas.

"Y'know, if you're bored... We could... continue somewhere else," I suggested.

"Yeah?" Sadie tucked her hair behind her ear.

"Yeah."

She sighed. "Honestly, AJ, I probably shouldn't have even offered. That was a tease. Sorry."

"No, it's all good. What, uh... what's on your mind?"

Sadie grabbed my hand and pulled me towards some shelter under one of the closed bars. "So, umm... I don't regret last night..."

"Me neither," I said, not liking where this is going.

"But I feel like... well..." Sadie twisted her hands. "Okay, I'm just gonna be straight up. We're such good friends and I care about you so much, and... I just don't want you to get hurt."

I nodded, squinting off into the rain. "Why... why would you think I would?"

"Because if we keep this going, I'll fuck up somehow and hurt you, I guarantee that." Sadie grimaced.

"I'm not asking you to commit to anything..."

"I know, I know. But, like... I'm not good with feelings. And we already like each other a lot. So if we add sex to that... Things could get messy."

"Okay," I said quickly. "Whatever you want."

"You're not mad, are you?" Sadie was watching me carefully.

"Of course I'm not mad at you." It was true. I was truly disappointed, and a little confused, but not mad. "It'll just be a Grad Trip thing, I guess." I gave her a reassuring smile.

"Yeah... Something to remember it by." When I saw how relieved Sadie was, I was glad I hadn't made a big stink about it. It was her choice, even if I didn't quite get the reasoning.

She pulled me into a tight hug and I hugged her back.

It rained hard on our last day as well, putting a bit of a damper on the end of the trip.

"How'd it go?" I asked Bridget when I saw her around lunchtime.

"Oh, yeah... yeah, it was great. Really fun hanging out," she mumbled.

I hid my smile, still feeling a little guilty about what I'd seen.

"Fuck it, let's go for a swim! I'm not gonna let this rain ruin our last day!" Sadie burst in.

Sadie, Jules, Bridget, and I charged out under the downpour and into the ocean, splashing around in the rain and the churning waves. After a time, Dylan and Faith joined us, giggling as they were soaked before they even hit the surf.

"Sadie! Did you have fun on Saturday night?" Faith grinned.

Sadie raised an eyebrow, shrugging. "Sure... did you?"

Faith tossed her braids, wiggling her eyebrows. "Well, who doesn't like a good show?"

Dylan laughed. "Gigi won't shut up about that guy, if you feel like sharing."

Sadie smirked. "He's a free agent, he can do what he likes..."

I dove beneath the water before anyone could clock the look on my face.

Damp, glum, and crashing hard from four days of partying, we piled on the bus to the airport after dinner.

Our orientation leaders dropped us off at the terminal, and I saw Bridget saying an awkward goodbye to Zara, who wrapped her in a big hug. "Text me—" I saw Zara mouth, and when Bridget turned away, she was pulling her hat down to hide her smile.

The airplane shuddered and hummed its way into the sky, leaving Mexico behind. It was late, so they soon turned off the cabin lights and many of my classmates' conversations quieted as they passed out in their seats.

Bridget closed her eyes and was soon snoring softly in the window seat. There was an empty seat between us, so I could have stretched out a little, but I didn't try to sleep. I had a lot on my mind, trying to figure out how I felt about the Sadie Situation and the Mackenzie Situation, and everything that had happened during our wild Grad Trip.

Eventually I did slip into a light doze, but in what felt like a moment I awoke to my phone lighting up. It was an AirDrop, a photo sent over Bluetooth, taken from inside the airplane bathroom, centered on the door.

Text overtop read: "Knock three times. Be chill."

I frowned, confusion and a little excitement bubbling up inside me. Why would someone want to meet me in the airplane bathroom? Maybe it was Sadie. Maybe she'd changed her mind.

Or maybe this was some stupid prank by one of my classmates.

Swallowing, I glanced around, but seeing no sign of a flight attendant, I headed back towards the bathroom, finger-combing my hair nervously.

I knocked three times on the locked door, half-expecting to hear an elderly vacationer tell me it was occupied. Instead the latch slid back, the door opened, and someone pulled me into the tiny, cramped bathroom.

It was Mackenzie Taylor. Her hair was in two French braids, she wore a casually clinging white miniskirt, a matching cropped tanktop and Adidas sneakers. She was glaring at me.

"Mackenzie, what--" I whispered, panicking slightly. Now I was sure this was a prank. I instantly expected her to somehow lock me in here or take a photo to claim I had burst in on her or something.

Instead she cut me off with a hushed "Shut up—" and pulled my head down to kiss me. I felt her tongue slip into my mouth as her soft lips crushed to mine, and I was filled with the rushing memory of prom night, her vanilla and lilac scent, the taste of her lip gloss.

But then I remembered the disgusted look on her face the last time she'd spoken to me, and I pulled away. "What the fuck?"

"Quiet—do you want them to hear? I'm pretty sure this is actually illegal," Mackenzie snapped.

"I thought you hated me?"

"Jesus..." Mackenzie gritted her teeth. "No, I don't...I was just... you were fooling around with my friends in a hot tub, it was weird—"

"What, were you jealous?" I blurted. It honestly sounded ridiculous to even my own ears, but Mackenzie went pink.

"Jealous? In your fucking dreams," She bit out. "I just didn't expect..."

"...To see me actually having fun on Grad Trip?"

"I don't have to explain myself to you." Mackenzie huffed, planting her foot, crossing her arms. "...Now do you want to do this or not?"

I wanted to storm out. But I knew I couldn't pass this up, even if it meant being thrown in airport jail. I leaned down and kissed her, hard and bruising.

Her nails dug into my arm and shoulder blade as we made out, pulling at each other's clothes, stumbling backwards only a single step before I had her pinned her to the sink. It wasn't the smallest airplane bathroom I'd ever been in, but there was still barely enough room for the two of us.

"Hurry—" She panted, and I obliged, my hand sliding up her toned thigh, under that tight little miniskirt to cup her firm, round ass, palm her sex. She was wet under her panties and I yanked them aside as she shoved her hand into my sweatpants to squeeze my hardening cock.

As my finger slid inside Mackenzie's tight pussy, she bit down on my neck to muffle the gasp, writhing against me. This was rougher than last time, angrier, more desperate. My thumb fluttered on her clit as I yanked up her tanktop to capture her stiff nipple between my lips, fondle her high, ripe tits.

Moaning softly, head back against the mirror, Mackenzie finally got my erect cock out of my sweats, stroking it urgently with both hands.

"Is that what you want?" I asked, breathless.

Blazing eyes locking onto mine, Mackenzie nodded. "...Just put it in."

"Ask me nicely." I realized suddenly that this would be my first time having sex completely sober, but the lust, the anger, and leftover embarrassment was clouding my head and loosening my tongue just as much as any alcohol.

"God, you're so fucking lame..." Mackenzie rolled her eyes, but I drove a finger inside her, hard, and she clapped a hand over her mouth, eyelids fluttering. "Ah—god damn it--I want your cock... please, I want you to fuck me..."

I removed my fingers and replaced them with my thick erection, shoving hard into Mackenzie's hot, clasping cunt. I could feel her walls parting as I bottomed out inside her, molding around my girth like last time—she had such a tight, gripping little pussy.

"Fuck—" Mackenzie's abs flexed as she took my cock, rocking her hips against me. Showing off her dancer's flexibility, her bare leg went up and over my shoulder, planting her sneaker on the bulkhead, so she was folded up against the mirror, perched on the edge of the sink

Unable to move too much, I drove forward with rough, short stabs of my cock, sliding out only two or three inches before punching myself balls-deep inside her again.

"Unh... unhh... hhh...hff...mff--- " Each quick thrust forced Mackenzie's breath harsh through her clenched teeth. Her thighs were spread wide, her mini-skirt pushed up around her hips to display my swollen shaft splitting her silky folds. My thumb was still riding the pearl of her clit, trying to match the way she had touched herself that first time. It must have been close, because she was squirming, one hand clinging to the back of my neck, the other fisting my t-shirt.

"You're so wet..." I gasped and Mackenzie flushed, looking down at her own pussy gushing around my girth, the sound of my hardness churning her sopping sex filling the tiny bathroom.

"Oh my god..." She moaned, as if she were scolding her own body. Her bottom lip trembled as she shuddered. "Fuck, that feels good--" She finally burst out in a whine of frustration. "Why... do you...feel...so...fucking good--"

With a huff of triumph, I lifted her other leg under the knee, so her hips were suspended in mid-air as I fucked her, hanging off the rim of the sink. I bent to devour her tits with my tongue and lips, even grazing her nipples with my teeth, and her fingers knitted into my hair and tugged, grinding back into me, thrusting her chest out.

As I railed her harder in this position, the mirror began to rattle, and we both grimaced at the noise. If we got caught, this would all be over, just like that.

"Stand up, turn around..." I muttered, pulling out of her, and Mackenzie nodded hurriedly, clambering shakily down from the sink. This position was completely new to me, but when she turned and bent over, pushing up her mini-skirt to reveal the pert bubble of her ass, I didn't hesitate.

Grabbing two handfuls of the soft, tight globes, divided between fair and bronzed by tan lines from the trip, I plunged my cock back inside her waiting pussy and kept fucking her.