The Pretty Girls
Copyright© 2024 by MyBestFriendForever
Chapter 1: The Pretty Girls
Coming of Age Sex Story: Chapter 1: The Pretty Girls - Jack and his senior year with the Prettiest Girls in School
Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa Mult Teenagers Consensual Romantic BiSexual Heterosexual Fiction School Group Sex Polygamy/Polyamory Interracial White Male Cream Pie
It’s been a month since I moved to California from New York, and school is going alright so far.
Okay, that’s a lie.
It’s going pretty terribly – four weeks into senior year, and I’m still utterly friendless. I can’t even remember the last time I talked to someone in the hallway except for when I mumbled an apology after bumping into a couple making out against the lockers.
It wasn’t my fault that all the guys seemed intent on ignoring me before I’d even talked to them. I tried my best to make a friendly first impression on the first day, but I didn’t expect the imaginary walls around the already-established friend groups to feel so impenetrable.
I wasn’t athletic enough to try out for any sports teams, and besides it was already too late as a senior. I didn’t know enough about stuff like D&D or Warhammer to get into it with those guys, and there was no way I was going to be let into the inner circle of the popular, preppy kids either.
It was a big school, and there were more social circles than I could count on one hand: the goths, the stoners, the theater kids, the nerds, and about a dozen other of the usual cliques. Not quite fitting into any of them, it was pretty clear that I was stuck being the odd one out.
October rolled around, and pathetic as it was, I had mostly resigned myself to slugging through my last year of high school as a loner.
That was until I met Beatriz, one of the Pretty Girls.
First, let me explain who the Pretty Girls are.
Five Girls. Each and every one of them was a stunning diva. And they all hated each other.
These girls weren’t just your run-of-the-mill cute either. They were the wet-dreams-come-to-life of every teenage boy in the school. Gorgeous, stunning knockouts with bodies that would make even Aphrodite jealous.
Now, why would a girl like THAT ever need to talk to a guy like me? The answer is more practical than you might think.
The fact that they were all known under the same moniker might make it seem like they were all friends, but that couldn’t be further from the truth. Each of them belonged to separate, varying friend groups, and it created some tense dynamics between them. It was almost like they were each the queen bees of their respective cliques, and they never, ever encroached upon the hives of the other Pretty Girls. And that’s where nobodies like me came in.
They needed proxies to communicate. No matter how much they hated each other, they were still the top socialites in the school and thus they needed a way to pass along information. Basically, I was employed as a messenger pigeon for these gorgeous babes who supposedly despised each other so much they were no longer on talking terms.
As I mentioned earlier, it all started with Beatriz.
The day I met her, I was walking alone (cuz I’m a loner, remember?) to the parking lot at the back of the school and I was ready to drive home in my crusty, trusty Honda Civic when I felt a tap on my shoulder.
I turned around and found myself face-to-face with a bombshell Brazilian beauty, with perfect almond-colored eyes and a big smile.
It looked like she’d run after me, and her cheeks were a little flush from the exertion although it was hard to tell over the general glow of her tanned skin. My eyes immediately drifted down from her face, and I caught a glimpse of her prodigious cleavage from over her tight crop top which she wore proudly, even though it was already October.
She gave me a smile that made me blush and I forced myself to jerk my gaze off her chest.
“Hey, you’re Jack, right?” she asked. She spoke with a slight accent and I found myself drawn to how her puffy lips moved when she spoke. It seemed like the corners of her mouth were perpetually turned upwards into a slight smile, and overall, she had a sunny vibe about her.
“Uh, yeah. And you’re Beatriz,” I said and immediately gave myself a mental kick in the shin for the lame response.
“Yep! Glad you already know me, that’s gonna make this a lot easier,” she said. I bit my tongue and withheld commenting on how every guy in the school probably knew her, seeing as she was the hottest thing from South America since Shakira.
Then she grabbed my arm with both hands and pulled me aside so that we weren’t standing in the middle of the sidewalk. I couldn’t help but notice how her boobs were pressing into my arm, and I tried in vain to stop staring too much. God, they were soft.
“So,” Beatriz said, “I need your help. Well, it doesn’t have to be your help specifically, but it’d be great if it could be, seeing as I’m already here, and you’re pretty cute.”
I stared back at her blankly, not quite knowing where this was going. She was still holding my arm against her body and I noticed that we were starting to get some stares from the other passing students, which was making it hard for me to focus on the conversation. This was one of the Pretty Girls, and having Beatriz wrapped around my arm wasn’t helping my cognitive skills function at their best.
Also, did she just call me cute?
“Sure, I guess,” I said, trying to keep it cool. “What do I need to do?”
Beatriz beamed at me and said, “Really? Great! Okay, so the thing is, I’m having a party this next weekend, a beginning-of-the-year kind of party, and I invited like half the grade and even booked an Airbnb for it.”
She gave me a look to make sure that I was listening so I nodded, and she smiled again before continuing.
“Obviously, I really want this party to be a success, and a success means that everyone turns up. The thing is, I heard Katherine Miller is also throwing a party on the same weekend,” she explained. “so...”
“Ah,” I said, beginning to see the problem. “So you need to make sure that people choose to go to your party instead of hers.”
“Exactly! And that’s where you come in.”
“Okay, now I’m confused again. I get your problem, but I don’t see how I can help.”
I bit my tongue before I made any snarky comment about how I hadn’t been invited to either party, so how was any of this my problem? Beatriz didn’t seem to notice how backhanded this request was anyway, so I kept my mouth shut. Besides, I would keep any excuse to keep this Brazilian chick on my arm for even a second longer.
“Well, isn’t it obvious?” Beatriz said. “I need you to go talk to Katherine so that she’ll move her party to a different weekend.”
I couldn’t help but shake my head and laugh. “Right, because Katherine Miller is going to agree to move her party just because I asked. You do realize, she probably doesn’t even know I exist, right? She’s one of the Pretty Girls, just like you!”
“No, silly. She’s going to agree to move her party because you’re going to tell her that I, Beatriz Oliviera, one of the OTHER Pretty Girls, am asking her to. Not you.”
“Okay, fine, but if that’s the case then why can’t you just tell her yourself?” I said, and before she could reply, I realized the answer myself. “Oh, right. It’s because you guys don’t get along.”
Beatriz frowned. “What?”
“I overheard people saying in the hallways that even between the Pretty Girls, the bad blood between you and Katherine was especially awful,” I explained. “I don’t know any of the details, though.”
“Oh ... I can’t believe people are still talking about that,” she muttered.
I cleared my throat, feeling a bit bad to have brought Beatriz’s mood down.
“Sorry for bringing it up, I didn’t know it was such a touchy subject,” I said, raising my hands.
“It’s whatever. So, can I count on you to tell Katherine by the end of the week then?” she asked.
“Sure, sure,” I said, eager to move on from the mention of Katherine.
“Great!” Beatriz exclaimed. “Let me know if you need anything. Also, you can just call me Bea.” Then she gave me a quick peck on the lips and giggled as she walked away.
I smiled and automatically touched my hand to where her lips had landed.
“Alright. See you later, Bea.”
She waved goodbye and I couldn’t help but stare after her almost reverently. Her ass was barely covered in a pair of jean short-shorts, exposing her long, golden-tanned legs, and the way her hips swayed with every step had me almost drooling.
I shook my head in disbelief. Just a few minutes prior, I was about to go straight home after having spent another quiet day alone, but now I suddenly had business with two of the hottest girls in school; Brazilian babe Beatriz, and Katherine Miller who I had never seen before.
Not to mention, I was pretty much on cloud nine from that little kiss from Beatriz (now Bea!), and couldn’t wipe the goofy grin off my face as I made my way to my car. I made sure to silently thank god for Brazilian casual kissing culture.
The happy feeling stayed with me the entire drive back home, and it wasn’t until I flopped on my bed after changing out of my school clothes that I realized I had been forgetting a very, very important issue.
How the hell was I supposed to talk to Katherine Miller?
Beatriz had reassured me that Katherine would listen to the request from HER and that it wouldn’t be coming from me, but like I said earlier; Katherine probably didn’t even know I existed. I didn’t know how I would even get an audience with her.
A month had already passed since I transferred, but all I knew about Katherine was that she was big on theater and somehow also a stoner. As far as the rumors on Pretty Girls go, Katherine was the one with the least gossip circulating about her. Besides that one tidbit about her and Beatriz having some particularly nasty history, there wasn’t a lot to go off if I wanted to find her.
Obviously, considering her title as Pretty Girl, she was probably gorgeous and hot as hell, but I’d never actually been able to confirm that in person.
I mentally facepalmed and chastised myself for not asking Beatriz to at least tell me where I could find Katherine. Tuesday was already almost over, which meant I had a maximum of three days to find, talk to, and convince one of the school’s top beauties to change her party plans. This might sound simple enough, but when you consider the fact that I was still relatively new to the school and didn’t know my way around that well, AND the fact that there are over a thousand kids here, my odds were looking pretty low.
It would be like trying to find a very sexy, very pretty needle in a haystack.
But I wasn’t one to give up that easily, especially because I wasn’t doing this for myself, but for Beatriz.
It certainly helped that she was an absolute showstopper in the looks department with her tanned skin and bodacious bosom on frequent display, but you also have to remember that at this point, it was already well into the first semester of the school year, and I had yet to make a single friend. I wasn’t about to let down the first and only person who’d been friendly to me so far.
I carried that determination with me the next day, and during every passing period, I made sure to take the longer, unfamiliar routes between classes so that I could scan new crowds for someone who might match the description of Katherine Miller. By lunchtime, however, I realized that I was getting nowhere.
The school was just too big. I had already gone through at least a dozen different hallways that I’d never even seen before, and it still seemed like there was more than half to go. The fact that I might’ve passed by her already by accident wasn’t a very promising thought either.
I skipped lunch and made some more laps around the school, trying to focus on places where I might find someone like Katherine. All I had to go off of was that she was a stoner/theater girl.
I checked the auditorium and I jogged around the entire arts block. Then I went to the fields and even checked under the bleachers, just in case the cliche about stoners congregating there was true, but I didn’t find anyone who seemed like they could be Katherine Miller. The rest of the day went much the same, and just like that, Wednesday was over and I only had two more days before I ended up disappointing one of the hottest girls I’d ever had the fortune of talking to.
On Thursday, I took a more investigative approach. I had made the mistake of assuming that someone as well-known and supposedly good-looking as Katherine Miller would be impossible to miss if I just looked around enough, but clearly, that wasn’t the case. This was going to take some more thorough searching.
This time I tried asking people if they knew where I could find her.
Now, I already knew that my social standing was pretty low, but I didn’t expect to get flat-out ignored as many times as I did. Some of the people just laughed at me when I asked them if they knew where I might find Katherine Miller, and there were a few that seemed like they might be Katherine’s friends, but they sneered at me and said she wouldn’t want to talk to me anyway. Everyone else just shrugged or walked past pretending they didn’t hear me.
By the final bell on Thursday, my determination from earlier had completely disappeared and I was in a pretty foul mood. I was also beginning to have a damn poor evaluation of this Katherine person who I’d never even met, because judging by the way her ‘friends’ were assholes, I didn’t think I had much friendliness to expect from her either. Being ignored all day can make a guy pretty spiteful (but seriously, high schoolers can be evil as hell sometimes).
Friday came along, and I was on my last straw. I tried spending the first passing period with a hail-mary attempt at finding this elusive Katherine but to no avail. Lunch came along again and I had pretty much given up. I was already mentally going through ways I could apologize to Beatriz and try to make it up to her, but in my heart, I knew it would most likely be a lost cause.
It was in this rather pathetic state that I was standing in the cafeteria line when I felt a tap on my shoulder.
I whipped my head around but there was nobody behind me. Then I heard a familiar laugh from the opposite direction and found Beatriz standing right next to me, with the same playful grin I recognized from several days ago.
“Gotcha!” she said. She was sporting a soccer jersey which she had tied in a knot above her belly button, and the athletic curvature of her legs was clear through her skintight jeans. Her flat tummy was a sight for sore eyes, and after taking a look at this beauty again, I felt even worse about my failure.
“Hi, Beatriz,” I said. I must’ve sounded pretty miserable from the way Beatriz’s smile immediately faded.
“What’s wrong?” she asked, genuine concern on her face.
“I couldn’t find Katherine,” I mumbled under my breath. I turned away, unable to look her in the eye.
“What? I couldn’t hear you,” Beatriz said.
“I’m sorry! I couldn’t find Katherine so I haven’t even had the chance to talk to her yet,” I said, raising my voice.
Beatriz didn’t say anything and I figured she must have just been shocked out of disappointment.
“I looked everywhere for her, I really did,” I started explaining. “But I swear she must have been absent or something because I just couldn’t find her. It’s like there’s an inside joke that I’m missing because when I asked people where I could find her they just laughed and I didn’t get anywhere –”
Suddenly, I heard Beatriz start laughing behind me. It wasn’t just a little laugh either, but the full-blown hysterical kind that had Beatriz doubling over and wheezing by the end of it.
“What?” I asked, color rising to my cheeks.
Beatriz waved her hand in front of her, and for a moment it seemed like she was done, but then she looked at me again and had another laughing fit.
“What?! It’s not funny!” I said hotly.
“Sorry, sorry,” She said between breaths, wiping tears from her eyes. “It’s just – I’m imagining you running around the school for three days straight looking for her – and I –” Then she burst out in laughter again.
“Yeah, I was running around school because YOU asked me to go talk to Katherine!” I said. “Except she’s like a ghost!”
“Like a ghost,” Beatriz snorted, and it was clear that I was missing something. Tired of being the butt of the joke without any explanation, I turned away from Beatriz.
“Hey, don’t be mad, Jack. I just forgot you were still new to the school so I assumed you already knew,” Beatriz said, putting a placating hand on my shoulder.
“Knew what?” I asked impatiently.
“Jack, Katherine has spent every lunch period for the last three years in the theater room.”
“Oh.”
The theater room. I was an idiot. Somehow, even though I went to check the auditorium because I knew she was a theater student, it had never occurred to me that there was a separate room just for theater.
I facepalmed. “Is she there right now?” I asked.
Beatriz nodded, the traces of laughter still lining her pretty mouth.
I started heading back out of the cafeteria toward the arts block.
“Wait, Jack! Are you gonna take your lunch with you?” Beatriz asked from behind me.
Looking down, I realized I was still holding my lunch tray. I handed the tray to Beatriz who looked at me confused.
“I’m gonna go see Katherine right now so can you hold onto that for me Beatriz?” I said.
“Um, sure. Should I just wait for you here or –”
“I’ll be back as soon as I can!” I said before turning back toward the exit.
“Also I told you to just call me Bea!!” I heard her shout after me, but by then I was already running back through the lunchtime crowds, toward Katherine Miller.
It only took me five minutes to find her now that I knew where to look. The theater room was a smaller, cozier version of the main auditorium, and it was nestled in the very back of the arts center building near the edge of the campus. I would never have thought to look there on my own.
The door to the theater room had a small window, and through it, I could see a group of students sitting in a circle on the empty stage, eating and talking with each other. I scanned the faces and it was quickly apparent which one of them was Katherine Miller.
Among the dozen students, only one girl emanated an aura of attractiveness like nobody else.
She had auburn hair that went down to her lower back in soft waves, and she wore thick, black-rimmed glasses that would have looked ridiculous on anybody else but instead gave her a handsome, vintage look. Beatriz certainly oozed more sex appeal with her golden skin and flirtatious personality, but it was undoubtedly clear that the title of Pretty Girl fit Katherine better. Her outfit was charming, not raunchy, and every movement she made was just plain pleasant to watch.
Katherine Miller was the loveliest girl I had ever seen.
Suddenly, the adrenaline dissipated and it was replaced by a cold nervousness. It was a very daunting prospect to barge into the small theater room and demand to talk to Katherine in front of all of her friends.
But I had Bea to think about. This was a favor for her, and the truth was that her playful, easy-going attitude was quickly becoming something I wanted to experience more frequently as well.
I wiped my palms on my shirt and opened the door to the theater room.
The room went dead silent, and all eyes turned to me.
I stood dumbly at the entrance for a second before I said, “Hi, I’m Jack.”
Smooth, I know.
Nobody replied, and I heard someone snicker.
I cleared my throat and continued, “I need to talk to Katherine Miller if that’s okay.”
The rest of the kids all looked at each other before one of them said, “No, it’s not okay. Fuck off, Jack.”
He said my name at the end with extra emphasis, like an insult.
Before I could say something back, the girl who I assumed was Katherine sighed and shot the boy a look. He immediately shrunk back as if he had just been scolded. Then she stood up from the circle and came over to me.
“Hey, Jack. Sorry about Justin, just ignore him” she said as she led me away from the rest of the group.
I simply shook my head and let out a breath.
“It’s okay, it’s just ... What’s his problem?” I said, unable to help myself.
Katherine laughed. “He normally isn’t that much of a jerk. It’s just that usually, when people we don’t know suddenly come here saying they want to talk to me, they’re usually here to ask me out, and I guess he just got tired of it. To be honest, I’m a little tired of it too.”
Then she arched her eyebrow and gave me a pointed look, and I realized she was indirectly asking if that was the reason I was here too.
“Oh, I’m not here to ask you out, don’t worry,” I said quickly. “That would be pretty weird considering we don’t even know each other.”
Katherine smiled and nodded.
“Glad we’re on the same page,” she said. “So what did you want to talk about then?”
Katherine was being a lot nicer than I had expected, and I began to feel bad about what I had to ask.
“Um, do you know Beatriz?” I asked.
She rolled her eyes. “Yeah, of course I know Bea. What about her?”
“Well, she’s having a party the weekend after the next, and she wants as many turn-ups as possible.”
“Okay, so what?”
“Beatriz asked me to ask you to move your party to a different date to make sure that people don’t go to your party instead of hers.”
Katherine sighed and took a seat in one of the retractable theater chairs.
“Classic Bea. Always needs to make everything about herself,” she muttered. Then she gave me an unapologetic look and said, “I’m not moving my party. That slut can go fuck herself.”
One of her friends called out, “You alright, Kat?”
“Yeah, it’s fine, don’t worry,” she replied.
My heart sank and I was also slightly shocked at the unexpected vehemence in her words. Turns out, the rumors that Katherine and Bea didn’t get along were more than justified.
“Why not? Is there nothing you can do?” I asked, desperation creeping into my voice.
“The question isn’t ‘why not’, it’s ‘why should I’. Also, why do you care so much about whether or not Beatriz’s party goes well? I doubt you were even invited,” she said.
I drew back at the bite in her tone.
“Beatriz asked me to, and I didn’t want to let her down.”
Katherine paused for a moment.
“That’s actually pretty strange, now that you mention it. Why did Bea go out of her way to make you the messenger?”
“Um, I don’t know. Maybe she just felt like it and picked me out at random,” I said, shrugging.
Katherine shook her head.
“We have a designated person for this. Usually, it’s either Eric or Kyle because they’re both gay.”
“What does that have to do with anything?” I asked.
“If they’re gay, then we don’t have to worry about the messengers falling for the Pretty Girls and skewing the messages in their favor.”
“Right. Well, maybe Beatriz just felt like a change of pace and wanted someone else to be the messenger for a change.”
“No,” said Katherine, “Bea only ever makes a move when there’s something she wants.”
She gave me a studying look from her seat.
“Lift up your hair,” she said.
“What?”
“Just do it. Let me fully see your face,” she ordered.
I did as told, and Katherine stood up and leaned in to examine me closer. For a split second, it seemed like she recognized something, but the moment was gone in an instant.
“I get it now,” she said.
“Get what?” I asked.
Katherine grinned. “Do you know what Bea’s last boyfriend looked like? He was tall and kind of lanky with brown hair. He was just like you, well, he was slightly more handsome maybe, but the similarity is still there.”
“I don’t see where this is going.”
“I think she’s interested in you, and that’s why she went out of her way to ask you, of all people, to be her messenger.”
Now that she mentioned it, I recalled that Beatriz had already known my name when she tapped my shoulder for the first time, which was certainly a strange occurrence. I mean, why would one of the Pretty Girls go out of their way to find out my name?
But I wasn’t fully convinced.
“Okay. So what, though?” I asked. “She still never invited me to the party, and it feels like she’s just using me as a carrier pigeon. Not exactly a normal way to express interest.”
Katherine rolled her eyes again. It seemed to be her habit.
“Beatriz isn’t a normal girl. She shows interest in weird ways, and trust me, her using you as a ‘carrier pigeon’ instead of Eric is saying something.”
I waggled my head. Certainly, Katherine must know Beatriz better than I could ever claim to, but it still didn’t seem plausible that a girl like her would even remotely entertain the idea of getting with a guy like me. This isn’t me being humble either, but just plain common sense. Beatriz was the picture of Brazilian hotness, from the golden tanned skin and a prodigious set of boobs to the searing look in her perfect brown eyes. In contrast, I was, as Katherine put it, ‘tall and kind of lanky with brown hair’.
“Okay, Jack. I’ll cut you a deal,” Katherine said with a smile that was decidedly less friendly than earlier. “I’ll promise to move my party to a different weekend as long as you can promise me something in return.”
“What do I need to do?” I asked warily.
“You just need to swear that you won’t go to Bea’s party no matter what, even if she invites you. And then, you’re gonna come to my party instead, on the following weekend.”
I frowned.
“Why does it matter if I go to her party or not? Also, how do you know if she’s going to end up inviting me or not?”
Katherine rolled her eyes again, and at this point, it would have gotten annoying had it been any other person, but as it stood, Katherine looked sexy as hell every time she did it so I didn’t say anything.
“I don’t know for sure, but on the off-chance that she does, then it’ll confirm my suspicions that she has a thing for you. And it matters because Beatriz is going to be upset if you blow her off but still come to my party. So now you have a choice. You can accept the deal to avoid Bea’s immediate disappointment but risk having to reject her later, or you can go back to her right now and tell her the news that I ain’t moving my party.”
I took a long moment to think.
I certainly didn’t want to disappoint Bea’s weekend party plans, regardless of whether I was invited or not. She might even give me another kiss if I manage to pull through with the plan. However, it would be an awful shame if she DID invite me and I had to decline.
Finally, I nodded.
“Okay, fine. Deal.”
We shook hands and I left the theater room quickly after that and hurried back to the cafeteria where I’d left Bea waiting with my tray of food. I glanced at my watch and muttered, “shit,” under my breath.
Lunch was almost over.
When I finally got back to the cafeteria, it was mostly empty as almost all of the students had already finished eating and were preparing for their next class. I quickly scanned the room and found Bea, sitting at one of the tables and chatting with her friends.
The other girls at the table eyed me suspiciously as I made my way over to Beatriz, and when I tapped her shoulder, one of them even got up from her seat and tried to stop me.
Beatriz turned around and when she saw that it was me, she gave me a faux glare and made a pouty face that accentuated her plump lips. God, she was hot.
“Jack! How could you make a girl wait so long,” she teased.
“Sorry, sorry,” I said, “But I have good news. Katherine said she would move her party to the weekend after yours.”
“Ohmigosh, really??!! Thank you so much, Jack!” she squealed, getting up to hug me. Her massive tits squished against my chest through the thin fabric of her sports jersey.
“And I totally forgot to mention it earlier, but you’re obviously invited to the party,” she said. “We can’t have the hero not be present, can we?”
“Ah, about that...”
Bea’s face fell. “Oh, you can’t make it?”
“Yeah, sorry. I, um, don’t really do parties.”
“Why?! It’ll be fun, I promise. I’ll even take care of–”
“Just let him be if he says he doesn’t wanna come,” one of her friends interrupted.
“Yeah, don’t force the poor guy,” another one said, snickering.
The way Bea looked truly crestfallen stabbed my heart, and I felt immensely guilty for having to lie to her like this. I had to remind myself that I’d only really gotten to know Beatriz three days ago and that we weren’t even at the level you could call friends. But before I’d even realized it, her fiercely friendly attitude and openness had me wanting to protect her feelings somehow, and I realized that it hurt more than I expected to reject her offer.
Bea quickly recovered, though, and her usual sunny smile returned.
“Fine, you’re off the hook this time. I’ll drag you with me next time for sure!” she said, swatting my upper arm.
Then her eyes went wide, and she exclaimed, “Oh! I almost forgot again. Here’s my number, we’ll keep in touch so I can let you know when I’m hosting another party.”
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