The Catch-Up Ch. 02

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Author’s Note: I’m including a little cast list to keep track of characters, especially since I may have edited a couple names since you first read Chapter One. New characters will be added the chapter after they’re introduced. All characters are 18 or over.


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

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.

BRIDGET: A sardonic, tomboy friend of AJ’s who’s a bit of a stoner. Messy tawny hair, usually under a beanie, hazel eyes, and freckles.

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 eyes. Loud, bubbly, and a little wild.

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.


It’s a high school cliche straight out of an 80s sex comedy, but I never thought anyone actually lost their virginity on prom night.

Then it happened to me.

Since we were all painfully single, the plan was for Paige, Grant, Rani, Bridget, Sadie and I to go to prom as a group, in Rani’s parents’ old VW bus instead of renting a limo. We’d hoped Amanda could get permission from her folks to come too, but given that her religious family didn’t even know she hung out with boys outside of school, prom turned out to be a hard sell.

The weeks flew by leading up to the big day–graduation in the morning and prom in the evening. I breezed through Finals like usual, thinking about my encounter with Reagan and Eva often. Sometimes late at night I would pull up Reagan on Facebook, start to type out a message.

But she had made it pretty clear that nothing else was going to happen, so I always gave up and settled for “taking care” of myself, with the vivid memory of Reagan’s mouth around my cock and Eva’s aroused nipples poking through her shirt floating behind my eyelids.

I’d always been good at keeping secrets, but this one felt like it was burning a hole in my stomach-I practically wanted to scream it into a megaphone. Who could I possibly tell? Grant was out of the question, obviously. As Reagan had reminded me, she was still Grant’s ex and while I was pretty sure he was over her, he really didn’t need to know this.

Amanda was out too-she was nowhere near as conservative as her incredibly strict Mormon parents, but she could still be a bit of a prude about anything to do with sex.

Definitely not Paige either, even though I told her practically everything. Given her past crush on me, it just didn’t seem right. Rani was so shy it would just make her uncomfortable. Bridget was a bit unpredictable about keeping secrets, but I wouldn’t mind seeing the look on her face when she found out. And then there was Sadie…

Sadie was by far the most experienced of any of my friends, as far as I knew, and she was completely shameless when it came to talking about sex. It only took until the night before prom for it all to bubble over.

AJ: Can I tell you something crazy?

I lay back on my pillow, staring at my phone screen. Thank god I didn’t have long enough to regret it.

SADIE: Yes omg what??

Without thinking, I typed it out as quickly as I could and hit send.

AJ: Okay so on the last day of school Reagan wanted to meet up with me in the aud and we ended up kinda fooling around?

It was off. No taking it back now.



That is my name, but nobody calls me Ashley except my friends when they’re joking or my mother when she’s really not. There was a reason I’d been going by AJ since I was five. Grinning, I started to type out a response, but then my phone started buzzing, jolting me into dropping it on my face.

Fumbling, I picked up the call. “Uh, hi?”

“Oh my GOD!” Sadie’s voice crackled my phone speaker, loud enough that I worried my parents might hear down the hall. “At school? With Grant’s ex? Who ARE you?” Sadie was clearly thrilled at the scandal of it all. I had definitely made the right choice of confidant.

“I know, I know–” I muttered. “It wasn’t planned or anything, she just messaged me to come to the auditorium and just-went for it.”

“So, what–did you guys make out?”

It was so strange to be actually talking about this stuff out loud. People at school did canlı bahis şirketleri it all the time, but I’d never had anything of my own to add. “Uh, yup…”

Sadie could obviously tell from my tone that it hadn’t ended there. “AND… what? You two didn’t…”

“No, no, not–not all the way!” I could feel myself going red.

“She blew you, didn’t she?”

My choked silence spoke volumes.

“KNEW IT. I knew it. How was it? I heard she’s really good!”

I sighed heavily. “…Yup. It was fucking incredible.”

“Aw, baby AJ! I’m so proud of you. I bet she’s wishing she’d picked you instead of Grant,” Sadie said matter-of-factly.

That same thought had occurred to me, but it was a nice ego boost to hear Sadie say it. “I don’t know, maybe. Wait, what do you mean, you’ve heard she’s really good–“

“Well, yeah, I mean since her and Grant broke up there’s been some talk… She’s clearly a horny gal, what can I say?”

“Yeah…” I said a bit quietly.

“AJ! Come on… did you really think the girl who randomly deepthroated you during school hours was so innocent? Y’know, thanks to Reagan’s slutty phase, you’re no longer 100% a virgin. Respect the slutty phase.”

I laughed. “I guess I can’t really argue with that.”

“No, you can’t.” Sadie sighed and I could hear her dropping back onto her pillow. “On the last day of school with your friend’s ex, though… That’s pretty fuckin’ hot.” Sadie’s voice came through soft and a little bit husky in my ear over the phone.

I found myself imagining my curvy, busty friend lying in bed, blonde hair fanning out around her, holding her phone to her ear and biting her lip. She’d be in her pajamas, maybe her bra and underwear. Maybe even less.

“…Yeah. Yeah, it was.” Nonchalantly, I slipped a hand beneath the covers, just letting it rest on the outside of my boxer-briefs. It occurred to me I hadn’t told her about Eva yet. I knew Sadie would think that was even hotter, but it seemed a bit unfair to include the other girl in the story given how she’d later fled the scene.

“Did she swallow?”

The hairs on my arms stood on end at Sadie’s words, and I could feel something else rising too. “Mhm…” was all I was able to croak out.

“…Fuck.” Was it my imagination or did Sadie’s breath seem a bit heavier through the tiny speaker? “That’s good-since it was your first blowjob and everything. She wanna see you again?”

“No… Y’know, with Grant and everything-

“Yeah, It’s probably for the best.”

“I just…” I paused. “Finally a girl was actually interested in me and who knows when that’s gonna happen again-“

“No no no, no–shut up!” Sadie said emphatically. “You’re fine. You’re a great guy, a really nice guy, and contrary to popular belief, a lot of girls do find that pretty fuckin’ attractive. Sure, Reagan was horny, but she picked you, because she’s comfortable around you and you’re a nice boy who deserves some sloppy head.”

“Jesus–” I snorted and Sadie just laughed.

After we hung up I jerked off as usual, my thoughts moving from Reagan, to Eva, and then to Sadie in her room on the other side of town. I came hard into my hand at the thought that she might be doing the same thing, full thighs spread, those notoriously huge tits shaking as she played with herself.

Graduation Day was a blur. Before I knew it, that oh-so-important walk across the stage was long over and I was trying to extricate myself from my mother’s comb while Rani leaned on the horn of the bright yellow VW hippie-van outside my house.

“Take lots of photos!” My mum shouted after me from the front step, despite the fact that she’d taken several thousand over the course of the day. She’s Indian, which she blames for being more than a bit coddling. I get my looks mostly from her-dark hair and eyes, light brown skin, and what I used to think was a big nose, although my face has mostly caught up in the past few years.

“Suit! He’s wearing a suit!” The normally quiet Rani screamed over her shoulder in the passenger seat. The door to the old VW slid open with a rattling creak and three girls (plus Grant) hollered and cat-called me as I crossed my lawn, my face turning the colour of my dark red tie. My grey suit was off-the-rack and didn’t fit me quite right, but apparently with a bit of hair product and contacts it was enough to give my friends a shock.

“007, is that you?” Paige mock-swooned as I clambered into the cramped interior. She was wearing a simple, dark green, halter-style dress, with her auburn curls pinned back by a vintage mother-of-pearl hairclip and red lipstick that reminded me uncomfortably of Reagan’s.

“Barf, Paige, he’s old and sexist. Hi. Nice monkey suit,” Bridget said as I squeezed in next to her. “Took you long enough.”

“Same to you.” Naturally, Bridget was also wearing a suit rather than dress, black, with a bowtie, her brown hair still tumbling loose around her shoulders, but clearly washed and brushed.

On the bench seat behind us were Grant and Sadie. He’d opted for canlı kaçak iddaa an actual tux, which looked good on his broad frame. He’d always been several inches taller than me, but in the past year he’d gotten in a lot better shape, too. Bastard.

“Sir.” I reached out a hand.

“Sir.” He inclined his head and shook it solemnly, before grinning. It was a weird ritual from back in Middle School that the girls always rolled their eyes at.

Sadie caught my eye. “Hiii. Sleep well?” She said, as if she knew exactly what I’d gotten up to after we hung up. Her golden hair was curled into full waves and gathered to one side of her neck, and her baby blue ball gown made good use of her gloriously full cleavage.

Before I could respond a calm, amused voice cut in. “Are we ready? I’m pretty sure this thing is going to stall out if we sit much longer.” It was our chauffeur, Rani’s older sister Shivani. Like me, they had an Indian mother, which was how we met when we were kids, but my dad was white, and theirs was Chinese.

The two of them couldn’t look more different. Rani was short and slight, with what was basically a bowlcut, and big, plastic-framed glasses, seemingly permanently stuck in her awkward phase, while Shiv was a a fashion student in uni-tall, stylish, gorgeous, and more than a bit intimidating.

“Yup, sorry,” I said hurriedly, avoiding her cat-eye-lined gaze in the rearview.

“Sorry, Shiv–I told him to hurry up,” Bridget said at the same moment. I knew for a fact that Bridget had a massive crush on her.

“All right. Hope you’re all ready for a hell of a night.” With a clank, Shivani put the VW in drive and we cheered. “A hell of a safe night!” She added as she pulled out.

It was a hell of a night. My cheeks were aching from smiling by the time ten o’clock rolled around and the DJ really started putting us through our paces. I know it’s not cool to like prom, but what can I say? I like my friends and I like to dance, although it had been a lot of years since I’d done it outside of the privacy of my room.

The music thrummed top forty hits we usually made fun of, but we screamed the words anyway. Classmates danced in and out of our group, and I could see their surprised grins at seeing me cutting loose for the first time.

“You’re a great dancer!” Faith Pearson shouted in my ear, putting a hand on my shoulder. It was high praise coming from one of the best dancers on the Pom Squad.

I looked down, but grinned. “Thanks–You look great, by the way,” I blurted, because she did. Faith was a cute, slender black girl, her dark curls put half up so they bounced down her back. Her dress was a gold and white two piece that showed off just a strip of her toned midriff.

“Aw, thanks!” She flashed a dazzling smile. “Can we get a pic?” She reached for her phone, but then Mackenzie Taylor’s voice somehow seemed to cut through the music.

“Faith, come on, it’s our song!” Mackenzie was probably the most popular girl in school, captain of the Pom Squad and adored by almost all. She was a few inches shorter than me, but her graceful confidence and perfect ballerina’s posture made her feel much taller. Her brown and blonde ombre hair was pulled back into an elegant updo, a few strands framing her face.

Mackenzie was incredibly pretty on a normal day, with big blue-gray eyes, full lips, and a button nose, but perfectly made up in a floaty, blushing pink gown subtly embroidered with flowers, she looked like a real life Disney princess.

Apparently not even noticing me, Mackenzie grabbed Faith by the wrist and turned on her heel. Faith gave me an apologetic look as she let herself be dragged away by her friend. “Are you coming to Mackenzie’s after?” She called over her shoulder.

“Uhh–Yeah!” I blurted without thinking. I had heard Mackenzie was having a rager at her parents’ huge place in the suburbs after prom. Guess I was going.

The next song was a slow one, but it was Kenny Rogers and Dolly Parton’s “Islands in the Stream”, one of me and Paige’s favourites to sing along to, usually in the car where no one else could hear us screech. She sidled up to me. “Wanna dance?”

“Sure!” I was in such a good mood that I didn’t hesitate. I’d never really slow-danced with anyone before, but it was nice, swaying a little awkwardly with her hand in mine as we lip-synced along.

“Did I hear you’re coming to Mackenzie’s?” She raised her eyebrows, looking up at me.

“Yeah, looks like it.” I swallowed. It was starting to sink in a little what exactly I was in for.

She shook her head slowly, grinning. “You’re really blossoming, aren’t you?”

“What’s that supposed to mean?”

“Oh, nothing.” She gave me one of those looks that made me worried. “Don’t worry, okay? I’ll be there when you have your first drink and when you’re throwing up on the lawn. Like half an hour later, probably?”

I laughed. “Shut up.”

As it turned out, I did a bit better than that.

Grant, Paige, Sadie and Bridget made me chug my first beer almost as soon as canlı kaçak bahis we walked in Mackenzie’s door, gathering around and chanting like a bunch of frat brothers. To be honest, it was pretty horrible and I felt like my stomach was full of gas bubbles the size of soccer balls, but then Sadie pressed a Solo cup of vodka and lemonade into my hand and that was much more my speed.

Mackenzie’s house was a McMansion-style monstrosity, but there was plenty of room for almost all of our graduating class, a smorgasbord of booze, a candy buffet, and even a bouncy castle in the back. And absolutely zero parental supervision.

It took about half an hour for the place to go from a loud and lively party to something getting close to chaos. The only rule Mackenzie had laid out was that no one was allowed to change, so girls playing beer pong in their prom dresses and guys spilling drinks on their tuxes only added to the debauchery.

It was pretty much everything I had expected from a high school party based on the wildest of my friends’ stories, only a lot more fun. Everyone was so happy to see each other and I found myself in rapt conversation with people I’d known for four plus years but barely spoken to.

As I sipped more vodka lemonade and found my head growing a little fuzzy, I talked more and more, cracking jokes that made girls I’d been too scared to say hi to in the halls burst out laughing, probably because they were even drunker than I was. It was awesome.

“AJ!” I felt someone throw their arms around my neck and lean all their weight on me, giving me a whiff of alcohol and perfume. “I can’t believe you’re hereeee!”

“Hi Jules…” I laughed.

I’d known Julia Wolff since Middle School, but back then she’d bullied me relentlessly for being a “weird, antisocial loser” (her words). She’d grown out of it and apologized by high school and we’d bonded in Grade 9 homeroom, though these days she was closer friends with Sadie than anyone.

She was a tall, tanned girl with strong shoulders and arms from years of rowing, a nosering, and loose, honey blonde hair, which looked great with her turquoise knee-length dress. She was clearly pretty wasted, a serene smile on her face, leaning slightly to the side.

“Where’s your date?” I asked. She had taken some guy from her rowing club.

“Ugh…” She rolled her eyes. “Gone, thank god. He was bugging me and bugging me about leaving, but, like… we’d just got here.” She was slurring slightly. She shrugged. “Whatever, guess someone’s not getting their dick sucked.”

I was tipsy enough that I managed not to choke on my drink.

“Speaking of which, I heard about youuu–” She narrowed her eyes, a wide, sly smile spreading across her face. “Little Ashley’s first blowjob–“

My mouth dropped open. “Sadie told you?” Jules collapsed into giggles. I guess I should have known better than to think Sadie wouldn’t tell Julia a piece of gossip that would tickle her as much as my first sexual experience. After the bullying had stopped, Julia had started treating me like a kid brother or a kind of pet, which could be sweet but also a bit annoying.

“What? First what?” Abruptly, Bridget barged into the conversation, clutching a can of Coors light. “Did you just say that Sadie–“

At this Julia only laughed harder. “No, no, not Sadie!” I said. I really didn’t like the idea of any rumours going around, let alone false ones.

“But yes, blowjob?” Bridget was clearly shocked, her normally relaxed, monotone voice going uncharacteristically high.

I opened my mouth and no sound came out. “Who, AJ?” Bridget demanded, eyes wide. “Tell me, oh my god! Who blew you!”

I saw a couple of heads turn our way, but luckily no one I knew very well. “Can you shut up?” I hissed. Julia was leaning on me, still getting over her giggles, and I lifted her arms off of me and dropped her unceremoniously onto Bridget, who staggered slightly.

“AJ! Tell me who blew you–” Bridget snapped after me, but I was already walking away, although it was proving slightly more difficult than normal.

My feet crossed over each other clumsily like someone had replaced my shoes with roller skates, and I had to lean slightly on the banister as I wobbled up the stairs. I wasn’t that drunk was I? I hadn’t started dancing on the table or trying to fight anyone yet, so I must have been doing okay.

I picked one of the identical white doors in the upper hallway and opened it. It was dark inside, but I saw a couple of shapes shifting on a bed and the slightly disgusting sounds of an enthusiastic make-out session. “Oops, sorry–” I muttered, closing the door in a hurry. The couple didn’t even seem to notice.

I guessed at another door and turned the knob. The room was lit up by the glow of fairy lights strung up on the wall above the bed. Sitting on the white plush rug was Mackenzie Taylor, the full tulle skirt of her gown spreading out around her, looking down at her phone.

“Shit. Sorry,” I said again. “I’m just… looking for the bathroom.”

Mackenzie looked up at me briefly, giving me a once over as she picked up her cup daintily and took a big sip. “There’s an en suite.” She pointed to the door on the other side of what I realized must be her room. “Don’t. Puke. Or do anything else gross.”

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