The Catch-Up Ch. 05

Categories: Genel.

May 23, 2021 // By:analsex // No Comment

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Disclaimer: All characters are 18 or older.

Author’s Note: Really appreciating all the comments and ratings, especially suggestions for future chapters and some really lovely notes about the characters and story. Please keep letting me know what you think!


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.

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.

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 on Grad Trip. An edgy, punky girl with short, purple hair and a lot of tattoos. Bridget has a thing for her.


GIGI: Sooo are you gonna tell me your name at some point?

UNKNOWN: Depends… are you gonna tell me how you “heard” about me?

GIGI: Lmao… well I actually watched you fuck Sadie on a beach in Mexico

UNKNOWN: I thought so haha

UNKNOWN: And? What was your review

With a jolt of excitement I saw that Gigi’s reply was a picture. It was a selfie of her reclining poolside, in a hot pink bikini that contrasted perfectly with her smooth, bronzed skin. She was lit up by the sun, her full cleavage lustrous and shining with what I guessed was tanning oil, her bee-sting lips glossy and parted.

Her sleek black hair was pulled into a bun, one eye was closed in a cheeky wink and her fingers, with their long acrylic nails, were spread into an “A-ok” gesture.

I hurriedly typed out a reply.

UNKNOWN: Hahaha always glad to see a satisfied audience

“Get off your phone—who could you possibly be texting?”

“Sorry—” I hurriedly locked my phone and put it away. It was a Saturday afternoon and the gang was back together, hanging out and drinking slushies in the park close to my house—Paige, Bridget, Grant, Rani and Amanda.

Paige was the one who had called me out. It felt a little weird to hang out with her, Grant, Rani canlı bahis şirketleri and Amanda again after everything that had happened—it was like everything had changed with me and they had missed it all. But it was also nice to just be hanging out like old times.

I’d been disappointed at first when Sadie had flaked on this particular hangout. I hadn’t seen her and we’d only texted a little since we got back from Grad Trip, though on the other hand, maybe it was for the best that this day stay uncomplicated.

“Probably texting ‘Violet.'” Bridget smirked, nudging me with her sneaker. I was more than relieved that things didn’t seem to be any different between us.

The group tittered with laughter and I rolled my eyes. “Boo. That is so old.” Violet was an English girl I had met on a family vacation in Grade 6. Being two very dorky 12-year-olds, we’d kept in touch by snail mail for a few years, despite all my friends insisting she was imaginary. At this point even my high school friends were familiar with the joke, despite it being years since we’d lost touch.

“Are we gonna play or what?” Amanda Graessle was on her feet and juggling a soccer ball from foot to foot. She was our “Mormon friend”, and as always, was technically rebelling against her parents just by hanging out in a group with Grant and I.

She’d also been the star of our school’s soccer team, and had secured a soccer scholarship to a Christian university, Hart College, in the same town as Douglas U, where I was going.

As usual, her curly, dark brown hair was held back by a stretchy headband, her ruddy, soft-featured face free of make-up. She was tall, about the same height as me, athletic and solidly built in the way weird, country parents might call “cornfed”. She wore a loose-fitting t-shirt, decidedly conservative shorts that went to the knee, and Keds.

“Ready, just let me put my shoes on…” Paige said, and Grant got up, too but Bridget, Rani and I stayed where we were.

“Come onnnn… we said we were going to play!” Amanda kicked the ball in our direction, and we all ducked.

“You said that—what’s the point, anyway, whatever team you’re on is just gonna win,” Bridget pointed out.

“Because it’ll be fun!” Amanda jogged around us to retrieve the ball. “AJ?”

Normally I was happy to indulge her, but my phone was itching in my pocket—I was pretty sure I’d felt a buzz, and Gigi’s reply would be waiting for me. But it was hard to resist Amanda’s bright brown eyes. She was one of the only people I knew who naturally did puppy-dog eyes without meaning to.

“Okay, okay, I’m coming.” I stood, finishing my slushie. “Come on, you two.” I grabbed Bridget and Rani by the arms and hauled them to their feet. “She’ll just keep asking.”

After a sweaty, tiring afternoon of impotently chasing after Amanda as she dribbled past all of us, we grabbed dinner at a Chinese restaurant. With all of us squeezed into a booth, I didn’t get on my phone again until it was late and I was back in my room.

GIGI: Not often I get left on read for hours…

I grimaced.

UNKNOWN: Sorry, busy day

GIGI: Me too. I spent the whole day working on my tan

UNKNOWN: Wow, sounds tiring

GIGI: I wanted to take pics… but u weren’t around so I didn’t have anyone to send them to

I bit my lip.

UNKNOWN: That’s a shame. I’m available now if you still want some feedback

GIGI: You’re way too late

GIGI: I already took off my swimsuit

I swallowed.

UNKNOWN: Of course. Guess there’s nothing to be done then

GIGI: I have a theory on why you won’t give me your name/insta

GIGI: You’re nasty looking

UNKNOWN: Maybe. Are you that shallow?

I paused for a moment before hitting send. I honestly had no idea what I was doing flirting over text with Gigi, but I had a feeling she’d appreciate a guy who wasn’t a total pushover.

GIGI: Wow…. as if you didn’t check my insta before you texted me

GIGI: I’m the one who gave you my number with no idea what you look like

UNKNOWN: Rightttt, you just care how I fuck

I typed that one out and hit send before I could think twice. There was a worrying pause of a minute or so, then I saw the three dots pop up.

GIGI: Omg you’re such a douche

GIGI: Send me a pic.

UNKNOWN: I’m nasty looking though

GIGI: Did I say it had to be of your face?

My eyed widened. This I hadn’t expected. Did Gigi want a… “dick pic”? Now? It felt weird to even put myself in the same sentence as that phrase.

I must have lay there running through it in my mind for a few minutes, because my phone buzzed again.

GIGI: I’m waiting…

It was followed canlı kaçak iddaa by another photo of Gigi, a mirror shot of her lounging in bed, with her chin resting in one hand and her phone held up in the other, eyebrows raised expectantly. She was wearing a loose tanktop and tiny running shorts, on her stomach with her feet in the air, one ankle crossed over the other, in white knee-high socks.

It was a casual, playful pose that happened to perfectly show off her obviously braless cleavage, toned legs and firm ass, lifted ever so nonchalantly in the air, round, tawny curves escaping from her far too small shorts.

“Fuuuck,” I breathed aloud, rolling onto my back and adjusting my sweatpants. I looked down to see a sizable bulge where my erection had been building almost since this conversation started. That didn’t look half bad.

If I was too cowardly to send Gigi an actual dick pic, maybe this would do. I grabbed my phone and trying not to overthink it, snapped a photo of my bottom half.

A bit of my torso was showing, but my t-shirt was hiding my stomach well, although it wouldn’t trick anyone into thinking I had a six pack under there. The bulge in my grey sweatpants on the other hand… I wasn’t sure if it was the angle or the fabric or what, but it looked casually huge. Perfect.

With slightly shaking fingers, I sent the photo. And then immediately tried to think of a semi-plausible caption.

UNKNOWN: Damn. Nice PJs. Here are mine

I threw my phone onto the other side of my bed, and covered my eyes. Then it buzzed and I frantically grabbed at it.

GIGI: Mm… looks comfy

I ran my tongue across my teeth.

UNKNOWN: Little less so, thanks to you

GIGI: Well, I don’t really wear PJs anyway, sooo

GIGI: Sleep tight

Gigi added her signature kiss mark emoji, and then another photo: A closeup of her full, soft lips, puckered in a kiss of their own, with her bare shoulders, the naked lines of her clavicle, and just the tops of her breasts filling the bottom of the frame. There was no tanktop in sight.

I stared at the photo for a long time before finally falling asleep.

The next day Bridget came over. I still wasn’t sure if I had “graduated” from P-School or not last time, but she noticed me checking my phone a few Streetfighter matches in and I ended up spilling the beans about Gigi.

“Holy shit… So she really doesn’t know it’s you?” Bridget’s eyes widened as I showed her the photos from Gigi from yesterday.

“No, definitely not.”

“So you’re catfishing her?”

“I’m not catfishing her! She wanted the guy who she saw having sex with Sadie to text her and that’s me!” I protested. “Anyway, I think she’s kind of into the mystery thing…”

My phone buzzed.

GIGI: I’m bored. Entertain me

“Fuck…” I beckoned Bridget over so she could look over my shoulder. “What should I say?”

Bridget furrowed her brow. “Don’t be too desperate. But don’t be boring either.”

“Great, thanks.” I rubbed my chin and started typing.

UNKNOWN: Lmao. Only boring people get bored

GIGI: Ew that sounds like something my dad would say

“That is something my Dad says,” Bridget smacked me on the shoulder.

“I’m laying the groundwork…” I tapped out my next message.

UNKNOWN: hahaha let’s play a game then

UNKNOWN: I guess something about you, you guess something about me

GIGI: Okay intrigued. What’s the prize for a correct guess

UNKNOWN: Idk you can send me a pic or something

GIGI: Slick….

UNKNOWN: You said you were bored

GIGI: I did say that

GIGI: Okay deal, but same if I get one right


UNKNOWN: I guess that you’ve slept with over five people

I could feel Bridget looking at me. “This is some evil mastermind shit. I don’t know if I should be creeped out or impressed.”

“Okay, to be fair, I haven’t lied once! I never said I didn’t know her–” My phone buzzed and we both crowded around it.

Today, Gigi was wearing another bodycon mini-dress, this one grey, with a ribbed knit and a three-button neckline. She was sitting on the end of her bed, holding her phone up to the mirror and leaning back with one leg crossed over the other, in thigh-high black socks, dark hair loose and bouncy, with her standard cool, sultry expression.

It wasn’t an overtly sexual pic, but the way Gigi’s curves filled out that tight dress, cleavage straining the single remaining button at the neck, and the way the high socks accentuated her legs, baring just a flash of tanned thigh below her skirt, made Bridget and I stare.

The caption simply said:

GIGI: Ding ding (obviously)

UNKNOWN: Wearing real canlı kaçak bahis clothes today I see

GIGI: Ofc I had church this morning

I snorted, highly doubting that.

GIGI: Hmm…

GIGI: I guess that you lost your virginity before Senior Year


GIGI: During then??

UNKNOWN: That’s two guesses! I guess that you’re half-Brazilian, half-Colombian


GIGI: You didn’t just guess that


“Careful…” Bridget said. “She’s just gonna know it’s someone who knows her.”

I shrugged. “She’d never guess it was me anyway.”

GIGI: All Latina everything

The attached pic from Gigi showed her standing with her back to the mirror, a classic, over the shoulder, back-arched booty shot, her dress stretched so tight across her round ass that it clung to the valley between her cheeks, clearly showing the shape of each firm globe. One stocking clad leg was popped playfully.

“Fuck…” Bridget whispered. These were the kind of pics that girls posted on their Instagram because they were feeling themselves and they didn’t mind compliments or the right kind of boys sliding into their DMs. I never imagined anyone, let alone Gigi Cordoso, would be taking them just for me.

I was through playing it cool.

UNKNOWN: God you’re hot

Gigi’s only reply was, of course, a kiss mark emoji.

GIGI: I guess that we’ve met in person before

Bridget raised her eyebrows. “Told you…”

“Fuck… I have to take a picture for her now.” I rubbed my chin. What the hell was I going to send her?

“Hands… forearms…” Bridget said suddenly.


“Straight girls love dudes’ hands and forearms. Everyone knows that!” She said impatiently.

“I don’t know, that’s embarrassing. My forearms aren’t like… muscley!”

Bridget rolled her eyes. “—They’re fine. And you have big hands–big enough hands…” She said quickly, doubling back on her words. “This girl is sending you thotty pics, you have to give her something.”

I nodded, steeling myself. “Okay, fine… Tell me how to pose.”

“I don’t fucking know… here just sit there, I’ll take it…” She grabbed my phone and pointed it down while my arms rested loosely across my lap. “Flex a little? No, too obvious… relax your fingers.”

“Good?” I asked.

She shrugged. “Best you can hope for, I think.”

I inspected the photo of my light brown forearms, covered in a decent amount of black hair, and my hands casually spread on my crossed legs. My forearms were assuredly average, but I’d always liked my hands—I have pretty long, well-proportioned fingers with prominent knuckles.

“Fuck it.” I typed out a caption and sent the photo.

UNKNOWN: Yes, we’ve met

UNKNOWN: Is that creepier or less creepy?

GIGI: Creepy is okay

GIGI: I like a good mystery

“Damn, this girl is thirsty,” Bridget said. She looked thoughtful, chewing her lip. “Do you want a really good guess?” I nodded and Bridget reached for my phone, typing it out for me.

UNKNOWN: I guess you have at least one nipple pierced

“Bridget!” I felt myself blushing even harder than I was before. “I can’t believe you just…Wait, does she?”

Bridget nodded. “As soon as she turned eighteen. I heard her telling Sadie about it on Grad Trip.”

“Holy shit…” Me and Bridget sat there in impatient silence for what felt like forever, until my phone buzzed. I grabbed it first, hiding it from Bridget.

GIGI: I swear this is rigged

My stomach clenched as I saw the picture. The frame showed Gigi’s full lips down to her waist, and her chest filled the frame, her full, perky breasts swelling out the front of her dress, still covered except for the bronzed cleavage on display. But visibly pressing through the thin fabric were her jutting nipples, so prominent I could make out the two tiny metal balls on either end of the barbell piercing through the stiff peak of her left breast.

“Let me see!” Bridget whined.

“No, no, she sent it to me, Bridget, she doesn’t know you’re here, it would be wrong of me to show you!”

“It’s that good, huh?” Bridget gritted her teeth. “Look, girls do it all the time… Have you sent her any thirst traps? Other than the forearm pic?”

I looked down. “Uh… yeah, I sent her a picture of… Well, I was wearing these sweatpants…” It sounded so stupid to say out loud.

“A bulge pic! You think every single one of her friends hasn’t seen that by now? Trust me, you text a single smiley face to a girl and she’s sending screenshots of that shit to her entire group chat!” Bridget jabbed me in the chest with her finger. “Let me see. Please…” She put her head to the side. That was a word Bridget didn’t say often.

I crumbled. “Fine.” I flipped my phone screen in her direction and her eyes widened.

“Fuck, that’s hot.” Bridget fidgeted a little, swallowing. Then my phone buzzed and Bridget visibly tensed as she saw the message.

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