The Catch-Up

Author's Note: All characters in this story are 18 years old or older, including those in high school or graduating. This is a story by adults for adults about adults.

*

By far the most insane year of my life started on the last day of high school.

All of us seniors had been let out of our last classes early and we'd filled up the Common Area, sitting around tables, lounging on benches. My classmates were taking last day selfies, reminiscing loudly about all the wild times they'd had. A couple pom team girls were crying, getting consoled by jocks.

"Can we just get on with it?" My friend Bridget groaned. She'd never been a fan of high school. I imagine it just didn't fit with her aesthetic. Bridget always joked that she was my best guy friend, and in fact when we were in Middle School together people had often mistaken us for two boys. A lot of people were dressed up or in their Senior gear for the last day, but Bridget was wearing an oversized jean jacket over a hoodie and sweatpants, with a knit beanie pulled over her tangled tawny hair.

"Cheer up, babe. Twenty minutes and we're fuckin' out of here forever." Sadie sidled up and sat down at our table. She'd become part of our group just over Senior Year. I'd always judged her as a loud, basic, ditzy, party girl, but I'd been wrong to. She was loud, could be a ditz, and loved a good party, but she was really a lot of fun to hang out with and was a lot smarter and a lot weirder than she let on. She had a reputation around school for being kind of a slut, which I think was exaggerated on account of her shameless attitude and famously huge... well... tits.

"What's up, sweeties?" Sadie nudged me. She was affectionate with all her friends, but it was still new enough to me that it made me blush and get awkward. "Don't tell me you're actually sad about leaving this shitstain?"

"Well--" I started and she laughed. "So what if I am? Y'know, it's our very last day and everything... I didn't think it was so bad."

Compared to most introverted, nerdy kids, I probably had a pretty good time at high school. I got good grades, I liked my teachers, and I got along with most people. Hartford Collegiate was small. I wasn't the most popular kid in school or anything--I didn't play sports and I wasn't on Student Council, but I did play piano in Jazz Band and I was in the school musicals, so most people knew me and I was friendly with a lot of the drama, band, and dance kids.

Of course, I had my close friends, including Paige, Bridget, Amanda, Rani, my only real guy friend, Grant, and sometimes Sadie, and we'd have fun on the weekends just hanging out in someone's basement, playing Mario Kart, or hitting up the local diner, ice cream shop, and Chinese restaurants. I didn't have much to complain about.

So why was I so depressed?

Like she usually did, my best friend Paige seemed to read my mind. "Are you thinking about all the stuff you never did?"

Fuck. I shook my head, trying not to let it show.

"Yup, that's it." Bridget narrowed her eyes at me. "Let's see: never smoked, never drank, never did drugs, never went to a real party..." She counted on her fingers. "Never cut class, never cheated on a test, never snuck out."

"Never went on a date," Paige added. I avoided her gaze on that one, because Paige had asked me out in Freshman year and I'd said no. It had been a whole thing. She wasn't ugly, a bit chubby, with curly auburn hair and big brown eyes, but we'd been friends for so long that I just didn't like her like that.

"You've never even kissed a girl, have you?" Bridget asked bluntly.

"Yeah, he has." Sadie grinned slyly. "Musical."

"Doesn't count," Bridget scoffed. "Not even close."

"Oh, c'mon..." I mumbled. Everyone at the table knew that my first kiss ever had been with Reagan Symons in a rehearsal for "Anything Goes" in the fall. This had been awkward enough, but to really pile it on, she was Grant's girlfriend at the time, and I'd had a massive crush on her for months.

They were right, of course. I had basically spent my entire high school career not doing all the things you're supposed to do in high school.

It wasn't that I had strict parents or I was a Mormon or something like my friend Amanda. And it's not like I never had the chance, either. I might have spent most nights playing PC games or reading fantasy novels, but Sadie or Paige would have been happy to bring me along to a party to get wasted. Even Bridget went out occasionally, when she wasn't smoking weed in her basement.

I guess I was just worried I might humiliate myself. What if all it took was one drink for me to pass out with shit in my pants, like Zack MacDaniel? What if I hooked up with someone who thought my dick was too small and told the whole school about it, like Austin Poloski?

These things happened, and I would hear all about it in the Commons the next day at lunch.

It just seemed safer to wait until I was a bit less completely fucking insecure. I don't when I expected to suddenly wake up and be cool, hot, and muscled, but I imagined it would be sometime in university.

Forcing down the lump in my throat, I looked at my phone to distract myself, but I even found myself hating that I had a shitty Samsung smartphone instead of an iPhone like everyone else.

Then I felt a familiar jolt as I saw Reagan's name. I'd been over her since before Christmas, of course, but some of those automatic things stuck around. It was a Facebook message, from three minutes ago.

REAGAN: AJ!! Come to the auditorium

I frowned. Weird message. I typed back.

AJ: In the Commons! What's up?

The three dots popped up and she replied almost instantly.

REAGAN: It's a surprise... Come alone!

She added the ghost emoji at the end of the message.

I chewed my lip, confused, but thoroughly intrigued. I couldn't stop my stomach from jumping a bit. A surprise from Reagan? Probably nothing. Reagan sang with Jazz Band, maybe they'd all put together a farewell thing or something.

I got up and pushed back my chair.

"Where are you going?" Paige asked.

"Off to your first makeout sesh? I bet Mrs. Sanderson's down." Bridget nodded her head towards the office, where our ancient, grumpy secretary lurked.

"None of your business. Maybe I'm gonna go do my first line of coke in the bathroom. Be right back." I grabbed my backpack and hurried down the hall.

The Hartford Auditorium was small, and there was normally nobody in there during the day, but as I knew from my musical days, the door stayed open. The door closed loudly behind me, leaving the place quiet as I jogged down the aisle steps.

"Hello?" I called.

Reagan poked her head out from behind the curtains onstage, brushed her bangs out of her eyes and smiled. "Hey!"

"Hi... Uh... whatcha doing?" I crossed the floor towards her.

"It's your last day, right? So I thought you'd want to see the place one last time." Reagan slipped out from between the curtains. She was in Grade 11, so she wasn't graduating until next year. Seeing her up on stage, I was reminded of why I'd liked her so much in the first place. She was sweet and witty and incredibly talented, a much better singer and actor than I'd ever be. At Hartford there were so few guys who wanted to be in musical that I'd somehow gotten a lead role in the fall.

She'd played Reno Sweeney, the lounge singer in Anything Goes, and sometimes looked like she walked out of an old-fashioned musical. She had brown hair cut around her chin in a cute retro style, elegant features, and soft, dark blue eyes. She was wearing red lipstick and a similarly vintage outfit: low-top Converse, a floral skirt, and a white blouse.

"Yeah." I looked around the empty auditorium with my hands in my pockets. "Good times." I felt a stab of annoyance as I remembered what it had been like to kiss Reagan every night for a week and then see her jump into Grant's arms at the end of the performance. They'd broken up since. I swallowed as I thought of why.

"She just really wanted to have sex. And I didn't," Grant had told me.

Reagan had been a lot less innocent than either Grant or I had ever thought. I got that Grant didn't feel he was ready, but honestly... I'd kill to have a problem like that.

Back in the fall when I liked her, of course. Back then.

"What is he doing?" I heard a girl's voice whisper. Reagan glanced back behind the curtain, making a shushing motion.

"Um..." I gave a confused laugh. "Is there someone back there? You know it's not my birthday, right? Am I about to be mugged?"

Reagan laughed. "No. Just... come here, okay?" She held out a hand.

Nervously finger-combing my hair, I hopped onto the stage and took it. We'd held hands before, but only on-stage. The vibe in here was getting weirder and weirder. Reagan led me through the curtains. It was pretty dark backstage, but a bit of light was filtering in from the back hallway, and illuminated by her phone I saw another familiar face.

"Took you long enough," Eva Nassry said. She was another Grade 11 girl I'd consider myself friendly with, a dancer in musical and Pom Squad who took my bus. She was half-Egyptian, petite, with light brown skin and long dark hair in a high ponytail. She wore the usual dance girl uniform--yoga pants and a tanktop.

"Oh. Hi. What, uh--why are you hiding back here?"

Eva popped her gum and glanced at Reagan. "Can you tell him already?"

"Okay, chill!" Reagan laughed, squaring her shoulders and tucking her hair behind her ear. "Okay, so. It's the last day of school, so you're gonna be graduating and everything. And you've always been such a nice, great guy... and castmate," She added. "And I wanted to do something to... y'know. Say thanks and bye, I guess."

I blushed and looked down at the words, but as she finished I looked up in time to see Reagan stand on her tiptoes and kiss me. The soft cushion of her lips, the smell of being close to her was familiar, but then her tongue slipped into my mouth and met mine and her fingers knitted into my hair and I realized I was making out with Reagan Symons. This was certainly not in the script.

In theory, I would have expected to panic, but I actually couldn't help but fall headlong into the sensation and kiss back as best I could, trying to remember all the things I'd ever heard from my friends or movies or the internet. Don't use too much tongue, hold her tight, follow her lead when it comes to head movement, be gentle but passionate... But honestly, nothing could distract me from how just enjoying it.

I was sure the bell should have rang by the time we broke apart. There was a blush to Reagan's cheeks, her breath had quickened, and there was the slightest smile curving her lips, so I guess I had done all right.

"Wow. Kissing is so weird close-up." Eva's eyebrow was arched severely at us.

"Uhh..." I stammered, suddenly aware that she'd been standing there the entire time.

"Shut up, Eva." Reagan turned back to me, eyes dancing. "Yes. Hi. Sorry to rush, but we don't have a lot of time. We can do more, if you want. If you're comfortable."

"M-more?" I barely got the word out.

"Yeah. I noticed you getting kind of hard, so..." Reagan stepped closer to me, gesturing to my pants. I realized with a lurch that there was indeed a bulge forming in the crotch of my jeans. Just from making out! I thought. Come on, man...

"Oh my god, is he?" Eva leaned over and stared at my lap with interest.

"Stop being weird, you're making him nervous." Reagan put her hand on my belt buckle. "So. Do you want me to take care of this for you or what?"

I never thought I'd only have seconds to decide something like this. My hands were sweaty, I was practically shaking, and I had no idea why Eva Nassry was here. But it was the last day of Grade 12, and my former crush was about to... Well, do something to my dick.

Fuck it. "Sure. Yes. Thanks."

"Cool. You're gonna like this, I promise." With quick, skillful hands, Reagan unbuckled my belt, popped the button.

This was really happening. "Wait, sorry... what is she--" I nodded to Eva.

"Don't look at me, I'm not... participating, okay?" Eva blushed slightly, putting her hands up.

"She wanted to watch, she's a virgin, like you. I thought it could be kind of hot," Reagan said, pausing with her hand on my fly. "If you don't think so, we can tell her to get lost."

"Hey." Eva pouted.

I honestly didn't know how I felt about someone watching my first... encounter, but I'd always found Eva pretty hot and I felt like I'd be missing out on a rare chance, so I just nodded. "Yeah, it's cool."

With that, Reagan smiled, unzipped my jeans and tugged down my boxer briefs (no holes, thank God), and my cock was out in front of a girl for the first time. Two, in point of fact.

I was only half-hard. I had a brief spasm that there were two girls staring at my dick at anything less than full fighting shape, but then Reagan took hold of me in her soft hand and started moving, and that soon took care of that.

I shivered, squeezing my eyes shut and glancing up at the theatre lights as, in Reagan's firm grasp, my cock swelled and stiffened into the raging, hormone-powered achingly hard erection of an 18-year-old virgin.

There was a small gasp from Eva. "Oh, shit." I glanced at her, and we made awkward eye contact, as her gaze flicked from my face, back to my hard-on, and then hurriedly away.

"Yeah." Reagan laughed softly. Her touch felt so much better than my own ever had, her fingers more delicate, more skillful, twisting and tugging and teasing. "He's a grower."

Then Reagan looked up at me and said the sexiest thing I'd ever heard. "I always knew you'd have a big dick."

I could have done a celebratory jig, or just come right then and there, but a moment later I was glad I didn't, because Reagan dropped to her knees, her skirt spreading out around her, and slipped the head of my cock into her mouth.

"Ohhh f-fuck," I whispered, as if scared of frightening her off, but Reagan stayed where she was, gently and steadily sucking me, taking down more of my shaft with each nod of her head. Her mouth was warm and wet, the tight "O" of her lips massaging my stiff length just like her fingers had, her tongue generously caressing the ridges of my cock.

Eva and I both watched, wide-eyed, mouths slightly open as Reagan sucked me off with the same passion and focus of her cooing a Broadway love ballad on stage. She controlled her pacing carefully, gulping me in and out with mounting speed before slowing, savouring each swallow, eyes closed almost reverently.

My cockhead slid from her embrace with a "pop" as she let a mouthful of saliva ooze down my cockhead in her wake, leaving a wet trail connecting to her lips. Her red lipstick was smeared all over the dusky, taut skin of my shaft.

I stared down at her, panting, still in shock. She grinned up at me, wiping her chin with the heel of her hand. "Enjoying your first blowjob, AJ?"

I let out a huff of laughter and nodded. "Jesus. Yeah--I can't believe it."

Reagan giggled. Almost idly, she began to rub her pursed lips up and down my shaft. "Eva? Sure you don't want to try?"

I put a hand to my flushed forehead. No way... that would definitely seal the deal--this had to be a dream.

But the other girl shook her head, although I noticed her cheeks were flushed. "...I think I'm good, thanks." She said in an uncharacteristically small, polite voice, avoiding my gaze.

"What time is it?" Reagan asked.

Eva hurriedly checked her phone. "3:05."

"Aw. Time to wrap it up."

I felt like whining and stomping my foot in disappointment like a little kid. This couldn't end! My straining cock, on the other hand, was certainly ready for the big finish. I was just glad I hadn't come in the first ten seconds.

"Too bad... I could suck this cock all day." Reagan grinned, starting to jack me hard with both hands. "Come sit by me, at least. You can see it close up. It'll be hotter that way."

Eva hesitated, but then she knelt down next to her friend, biting her lip as Reagan took me back into her mouth. "Tell me when, okay?" She said with her mouth half-full.

This time there was no pacing or teasing push-pull. I let out a long groan, digging my nails into my palm as Reagan bounced her head on my cock, plunging me in and out with the eager rhythm of slurping smacks that sounded so much better than I ever would have thought. I felt my cockhead hit the back of her throat and keep going, her lips nearly reaching the base of my shaft, her elegant nose brushing my dark, embarrassingly messy pubic hair.

"God... Oh my God..." I automatically put a hand on the back of Reagan's bobbing head to steady myself, feeling her soft hair beneath my fingers.

Next to her, Eva fidgeted on her knees, watching the obscene display. I caught her eye and she seemed to tense slightly, but held my gaze. I found myself thrusting into Reagan's sucking mouth, pushing her head down, forcing her to swallow my cock deeper as Eva stared up at me. My eyes slid down to the mounds in Eva's tanktop, her perky B-cups, just enough to squeeze in one hand.

She saw where I was looking, bit her lip, and before my eyes--before my very eyes, I swear, I saw the shape of her nipples rise to poke through her bralette, her thin tanktop.

"Fuck, I'm gonna come, I'm gonna--" I spat out in a panic, feeling the racing orgasm rush from my balls up the length of my cock.

"Mmmmm..." Reagan moaned, muffled, holding her hair back as my cock throbbed the first of my load into her mouth.

"Aggghhh fuck!" I gritted my teeth, my other hand reaching out and clamping down onto Eva's shoulder as I exploded, pumping cum down Reagan's throat. Eva's hand closed around my wrist, holding me there, even as my fingers dug into her muscles.

"Don't--Can I see..." Eva mumbled hurriedly, and Reagan threw her head back to release me, just in time for my cock give one last powerful spurt. Unfortunately for Eva, Reagan had directed my pulsing dick in her direction, and the final rope of creamy white cum splattered across Eva's neck and cheek.

She flinched, startled, and gasped, before letting out a whine. "Oh my God, Reagan! Ew--Ew!"

Reagan swallowed, wiping the drop that had overflowed onto her chin, and burst out laughing.

"Shit, sorry, Eva--" I babbled, but I was laughing too, rough on my dry throat.

"Shut up... fuck you guys," Bright red, Eva gave us both the finger and stomped off towards the door.

I helped Reagan to her feet, my head still spinning. "Bell's gonna ring soon. You're almost done," Reagan said, breathless.

"I don't know if I wanna go now, honestly."

Reagan laughed. "You have to. It was a farewell present." She reached up and gave me another deep kiss, and to my credit, I didn't flinch at the strange taste of my own cum that lingered on her tongue. Reagan seemed to appreciate it. "Very good manners, Lord Evelyn." It was my part from "Anything Goes".

"Oh, god." I grimaced at the memory. "Hey--Reagan. Thank you. That was... awesome." I summoned up my courage. "If you ever wanna..."

She shook her head, looking apologetic. "I'm still Grant's ex, AJ. This should probably be it. Have a good summer, though. You're gonna do great." With that, her hand trailed out of mine and she was gone.

I did up my jeans and walked to the edge of the stage, my own breath still audible in the empty auditorium. I still had a lot of catching up to do, but that was three firsts off the list. I imagined Bridget counting on her fingers again. Kissed a girl (for real), got a handjob, got a blowjob... all in the space of less than twenty minutes. And hey. Summer was just beginning.

I jumped down from the stage and practically sprinted out of the auditorium.