Highschool Sweethearts

(Note: The characters in this story are 18-year-old high school seniors.)

Another school day was coming to an end. Taylor hoisted his bag over his shoulder and made his way through the bustling hallways, too caught up in thought to pay much attention to his surroundings. He didn't have a shift at the comic book store tonight, so he figured he would just head home and work on his sketches. He had come up with a few more good ideas while he was trying in vain to keep his attention on the class material. Such was the serendipity of boring classes. He had just arrived at his locker and was preparing to unload his books into it, when his phone buzzed inside his pocket.

He pulled it out to check the new message and immediately recognised the beautiful blonde in the profile picture: Erika Moore. She was far too popular to be associating with a dorky guy like him, yet a fortuitous sequence of events had put them in contact some time back. Her message read: "Hey Taylor, I'd like to ask you something important. Could you meet me at the back entrance of the school in 10 mins? :)"

Taylor didn't know what this would be about, but he was happy to comply. Erika wasn't just a beautiful girl, but a very sweet one too, so if he could be of any help to her, he would do so gladly. He texted her an affirmative response before putting his school supplies into his locker and making his way to the meeting place. There was a garden of sorts at the back of the school, which was used by many as a hang-out spot during recess. Now that the day was ending, however, most students were taking the quickest route home, namely the front entrance, leaving the back as a convenient place to talk.

Taylor's eagerness had gotten him there a little earlier than intended, so he messed around on his new phone for a bit as he waited for her. A few minutes later, she emerged from the double doors. Erika was, in terms of appearance, a typical "queen bee"-type girl, with tanned skin, long wavy blonde hair, and blue eyes. She was tall for a girl and had a slender, athletic build thanks to years of gymnastics and cheerleading. She was wearing her school uniform, consisting of a white button-up shirt, a knee-length blue skirt, and black pantyhose. It wasn't a very flattering outfit, but almost anything looked good on her lovely hourglass figure.

"Oh Taylor, there you are," she said with a smile as she walked up to him. Contrary to what one might assume from her appearance, she wasn't a conceited "alpha woman"-type at all. The centre of attention did tend to gravitate towards her, as did the many rumours that were sure to emerge in your typical high school, but she was never the one to seek it out.

"Hey, good to see you, Erika," Taylor answered while tucking his phone away. His eyes gravitated for just a moment to the sight of her ample breasts straining against the snug fabric of her shirt, but he tore his gaze away and back to her face as inconspicuously as he could. A girl like her surely got ogled all the time, and he didn't want to contribute to that. "What did you want to ask me?"

The gentle wind played with her long hair, so she brushed a few locks of it behind her ear. "Well, my friend is coming too. It's something that concerns both of us, so we should wait for her. She'll be here any moment."

Just as Erika finished, someone else emerged from the school entrance. Taylor recognised her right away by her distinctive appearance: Jade Parker. Jade had fair skin, green eyes, and long hair dyed vibrant blue. She was shorter than Erika, with a slender but curvy physique and, notably, a huge rack. She wore the same plain school uniform, but the modest outfit did little to hide her alluring physique, with her magnificent chest putting serious pressure on the buttons of her shirt. Hers was perhaps the only bosom around that was harder to avoid staring at than Erika's.

And Taylor wasn't the only one who thought so. Jade was somewhat well-known around the school for being, in the words of some of the more vocal students, a Twitch thot. She ran a let's-play livestream channel, with a moderately-sized but very enthusiastic fanbase. Taylor had tuned in a few times out of curiosity, and while her gameplay and banter were certainly appealing, it was hard to deny that her appearance was a major draw. Taylor didn't know her well in-person, but she had always seemed like a nice and reserved girl, in contrast with her colourful appearance and reputation. The two of them would be considered strangers if not for a certain incident quite recently.

"Oh, you both beat me to it," she said as she spotted the two of them. "Hey Taylor. Remember me?" she asked with a shy smile as she walked up to join them.

"Yes, of course! How could I forget?" A blush crept up his cheeks as he remembered that particular memory with a mix of pride and embarrassment.

"Anyways," Erika said, idly twirling a strand of golden hair around her finger. "The thing we wanted to ask you is a little weird, but hear us out. Earlier today, during lunch break, we happened to be having a conversation about you..."

***

"Time to spill the beans, Erika," Jade said as she sat down at the lunch table, across from her long-time friend.

Erika was about to take a sip of coffee, but halted in place. "Beans? What did I do?"

"Your new love interest," Jade clarified, fluttering her eyelashes melodramatically. "The one you hinted at on Whatsapp. I wanna know the details."

"Oh, right." Erika completed her sip. "You were so excited, I thought there was some new shitty rumour about me or something."

"No, no, none of that. I'm just curious about this new guy. You made it sound like he was different from your other suitors, but you wouldn't tell me how or why."

"He's pretty different, yeah. But nothing has really happened between us yet, so I dunno if I should be talking about it. I don't want you to be disappointed if nothing comes of it."

"Aw, come on, it doesn't matter if anything comes of it, sharing these kinds of things is fun." Jade rested her arms on the table and leaned in towards Erika, smushing her heavy chest against the surface. "How about this: you tell me yours, and I'll tell you about my new crush."

Erika cocked an eyebrow. "You have a new crush too? That's bigger news than mine. Okay, fine, I'll tell you. But I'm not gonna say his name, so you can't judge him for anything that does or doesn't happen."

"Sounds like a deal to me," Jade rested her chin on her fist in anticipation.

"So, you know how I'm totally shit at math, right? Like, so shit that I'm still catching up on material from earlier years?"

"Uh, your words, not mine. But yeah."

"The school runs a partnering program for struggling students, and I got partnered with this guy who volunteered to help me with my maths. He's good at the subject, so he was a huge help. And, I dunno, he was just very supportive and considerate the whole time. He made no ham-fisted attempts at hitting on me either. Maybe I have unreasonably low expectations for boys, but that stuck with me."

"Are you sure he isn't gay? That'd be an explanation."

"No, I don't think so. His eyes would trail to my chest from time to time, as they always do. But he made a real effort not to act thirsty with me, and I appreciate that. Anyways, I fell out of touch with him a bit after that semester ended. Then when I broke up with Michael some time later, it dawned on me how much I missed having a really supportive person in my life. Not that you aren't a supportive friend, but there are some things you just can't ask your girl-friends to do for you. Like bringing you ice cream late at night when you're a depressed mess after a break-up."

Jade snorted a little in amusement. "You asked him to do that?"

"Well, I didn't ask, more like I hinted at how much I was craving it. But he went and brought it to me without a second thought, and even stuck around to let me vent all my worries and grievances to him. Not once did I feel judged for how pathetic I was being, and not once did he try to take advantage of my vulnerable state."

"That's really sweet. This was just like two or three weeks ago, right?"

"Yeah, something like that. And now that I'm getting over Michael, I'm starting to wonder if I should ask him out. He's not my usual type, but maybe that's a good thing. Maybe it'll stick this time."

"Aww, that sounds like a love story waiting to happen." Jade held her hand to her heart. "I know you said no judgement, but you better ask that guy out."

"Yeah, yeah, I think I will. Telling you that story has reminded me how much he meant to me over the past schoolyear. I'll ask him out sometime soon. But now it's your turn. This new fling of yours, is it a guy or a girl?"

"Fling isn't the right word. It's more like a... sudden infatuation? But uh, it's a guy."

"Oh really? How did that happen, miss I-don't-like-guys-that-much?"

Jade made a pouting face. "Hey, I do like guys. I just think many guys my age are tools, is all. To be fair, I don't know this new guy very well. He might turn out to be a tool too, but I don't think so."

"So how did you get into infatuation territory without getting to know him?"

"Okay, this is gonna sound like a cheesy romance novel, but hear me out. Just last week, I was on my way to use the ladies room between classes, and this dickhead followed me in. It was one of the football players, Jason Something. Anyways, this was on the top floor, so it was just me and him in there. Obviously he knew me from my livestreams, and he must've figured that since I'm busty I must be easy too. First he started hitting on me really crudely. You know that thing guys do where they think they're being smooth by blocking you from walking away? Yeah that. I shrugged it off as best I could, but I also forced myself to be nice about it, cause I didn't want any trouble. Well that didn't work out because apparently he took my being polite as an invitation to start touching me."

Erika's expression darkened. "Seriously? You got straight-up molested? Why didn't you tell me about this earlier?"

"Well, I didn't wanna raise any more of a ruckus about it. You know how people will hear of an event like that, spin it into a rumour, and suddenly I'm the one who sounds like a slut. Anyways, there's a positive spin to this. He'd only just started grabbing at me when this other guy that I didn't know entered. Apparently he saw that douchebag entering the ladies' room and figured something was fishy. He took a bunch of pictures of what happened and threatened the guy to back off or else he'd show them to the principal."

"That's a relief. Did it work?"

"Well, kinda. The jerk left me alone, but starting threatening him to delete the photos. When he refused, he got sucker punched. The guy fought back pretty valiantly, but he was smaller, so he got his ass kicked pretty bad. Ultimately the dickhead took his phone and destroyed it, along with the photos. Which, to be fair, he should've seen coming. But the jerk left after that, thankfully. He obviously couldn't continue his business with an eyewitness around. But guess what the guy with the phone did then?"

Erika was rather gobsmacked by the sequence of events she'd described. "Uhm, what did he do?"

"Even though he was the one with the black eye and the bloody nose, he rushed to make sure that I was okay. Did everything he could to comfort me before even worrying about himself. Something about that really stuck with me. From there, I helped him clean up his injuries, and together we testified to the principal about what happened. I dunno if the jerk got any serious punishment for it - probably not since we didn't have any proof. But I know the principal reprimanded him, so at least he'll have learned that he can't do whatever he wants in broad daylight, I guess."

"Jeez Jade, that really sucks. I'm sorry you had to deal with that."

"Yeah, it did suck. But on the other hand, the way that guy came to my rescue was like... pretty hot. Obviously the way it unfolded wasn't very heroic, but that makes it all the more impressive in a way. Like, he was clearly outmatched and he still did it for my sake. We parted ways pretty abruptly and I haven't spoken to him since, but I haven't been able to stop thinking about him. I really wanna track him down and properly thank him for what he did. And frankly, I'm thinking of asking him on a date. But I'll have to find out what class he's even in first."

"Aww, that's something of a good outcome at least. I hope you can find him soon. Do you know his name? Maybe I've heard of him."

"His name was Taylor, I believe. Taylor... gosh, what was his last name?"

"Wait, wait, wait." Erika's eyes grew big like saucers. "Taylor Barnes?"

"Barnes... yeah, I think that might be it. Brown hair, pretty short?"

"That's him!" Erika announced a bit too loudly, causing some heads to turn her way. A blush crept up her cheeks as she leaned in towards Jade and spoke more softly. "That's the guy I was talking about."

Jade quietly blinked at her friend for a few seconds as the gears of her brain fell into place. "The guy who helped you out with your math and your break-up is the same guy who saved me from getting groped? Are you saying we have a crush on the same guy?"

"Sounds like it." Erika leaned back in her seat with a ponderous expression. "And frankly, knowing that he performed such a heroic act makes me want to ask him out even more."

"Hey, what about me? Now that I know how sweet he is in everyday life, I definitely wanna ask him out too. You can't just call dibs on that."

"No, you're right. We're friends, we can't just make a run for it and try to ask him out before the other does. He have to let him decide who he'd rather date."

"Even then, we can't expect him to decide without trying out at least one date per person, right? So then someone still has to go first, and whoever goes first will get the advantage."

Erika sighed. "True again. Though, there might be one way that we could handle this..."

***

Taylor found himself pleasantly surprised as the girls related their favourable memories of him. He already knew, through his association with Erika, that she was friends with Jade, but he wasn't sure if his interactions with them were noteworthy enough that they would end up discussing them. "Wow, I'm flattered that you two have such a high opinion of me. I mean, in both cases I was just doing what I figured anyone would do, you know?"

Jade chuckled. "If only everyone was as supportive as you, then that crappy situation wouldn't have happened in the first place. Again, I'm really grateful for your help."

Taylor felt his cheeks reddening as he was showered with compliments by such lovely girls. "Oh, it was nothing. No, that's not true. But I did it gladly, there's no need to thank me."

"Thing is," Erika interjected. "I didn't call you here just so Jade could thank you for your heroism. Jade and I also had a question for you, and a bit of an odd one. Would you like to go on a date with us?"

Taylor blinked at them as he processed the request. Both girls were looking at him expectantly. "A date... with us?"

"Yup," Jade said. "A date with both of us, together, simultaneously."

Taylor still couldn't process it right away. Were they really saying what he thought they were saying? A date... with three people? That didn't sound right at all. Perhaps he had misinterpreted. Perhaps they just wanted to hang out as friends, and had called it a date mistakenly. He could ask them to clarify, of course, but he knew right away that he wouldn't have the guts to do so. If he was wrong, they'd think he was a conceited bastard for assuming that two girls would want a joined date with him. And even if his interpretation was right, he still wouldn't know the girls' true intentions. Perhaps they were dangling romantic intentions as a way to scam a free meal out of him? Perhaps this was a prank meant to embarrass him somehow? Or perhaps they were trying to get him isolated and outnumbered so they could steal his kidneys?

He shook the waterfall of doubts out of his mind and steeled his nerves. It was suddenly quite easy, not because he no longer believed those doubts, but because something crucial had occurred to him: he would gladly brave any of those risks for the chance to be with one of these sweet and beautiful girls, let alone to earn the affection of both. "Yes, I'd love to. That sounds like fun," he answered, doing his best to sound confident.

Both girls' eyes lit up with joy, which was a reward in and of itself. "Awesome," Erika said. "We were thinking of trying out the new Italian place at Baxter Road. I live close to the city centre, so we could all meet at my house and go from there. And maybe we can return to my house for some drinks after. How's that sound to you?"

Taylor felt odd about discussing something so unfamiliar so casually. "Yeah, that sounds great. Friday evening, I assume?"

"Yup. Meet you there at, say, six? I can make a reservation for us."

"That works." Taylor looked at Jade, who showed him a shy smile, then back at Erika. "I'm looking forward to it."

They exchanged some more small talk and pleasantries, before the girls said their goodbyes and departed together. Taylor hung around a little longer, wondering if this was all a pleasant dream that he was going to wake up from any moment now. When no wake-up happened, he went home as well, feeling both excited and anxious for the end of the week.

***

Taylor halted his bike in front of Erika's house. He recognised it from the last time he was here, bringing her ice cream after her break-up, but even so he double-checked the address that she had messaged him. School had finished about two hours ago, and ever since that time he had been mentally preparing himself for the date. Their conversation on Tuesday had given him a surge of confidence, but now that the dopamine from that had worn off and the actual date was about to begin, he felt nervous and unprepared.

For the last three days, he'd been worrying himself sick, making some pretty embarrassing Google searches like "how to talk to girls". The results weren't very enlightening, with most answers being either the usual platitudes that everyone knows about, or weird pickup artist tricks that he would feel gross for even attempting. One time he almost searched for "tips when losing your virginity", but he couldn't bring himself to press the enter key on it. He was sure that neither of the girls would do anything sexual on the first date, and even entertaining that possibility felt disrespectful. All in all, even though he'd had three days to prepare, he didn't feel like he'd made much progress. There was at least some comfort in knowing that he had done what he could, and that no amount of additional pondering or Googling would make him feel any more prepared.

He parked his bike next to Erika's house, and took a moment to ensure that his appearance was in order. He had put on a blue button-up shirt and some grey jeans - an outfit that he figured was neat enough for a date and casual enough in case it wasn't a date-date. A lot of anxious deliberation had gone into that choice, more than he cared to admit. It was a warm spring evening, so at least he didn't need to worry about wearing a jacket.

He approached the front door and rang the bell. In the few seconds that followed, his brain managed to derail into worrying about the chance of getting stood up. What if the girls weren't here at all? What would he do then? Call them to find out what's going on, and potentially embarrass himself further? Or quietly accept defeat and head home? Thankfully, he didn't have to answer that question, as he soon heard footsteps from inside.