A Chance Encounter (remake)

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A dorky young man hooks up with the hottest girls in school.
20.1k words
4.8
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34

Part 1 of the 2 part series

Updated 03/30/2025
Created 08/07/2017
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(This is the far-too-long-awaited continuation of my old classic. It's not a sequel but a complete rewrite, so you don't need to read or remember the original to read this one. If you like rampant wish-fulfilment, this is the story for you. I hope you enjoy!)

Among the dazzling lights and thumping music of the disco, Megan emptied her drink. She was a beautiful young woman with chin-length brown hair and green eyes. For her night out, she had put on a red crop top, skinny jeans, and knee-high boots - a formfitting outfit to show off her slender figure and the proud swell of her ample breasts. She'd already done her fair share of dancing, switching from guy to guy, all of whom were eager to grind themselves against her curvy body. Too eager. It was all too obvious how badly they wanted to get into her pants, and their flirting methods were neither subtle nor very original. On another night, she might have been flattered, and might've considered taking one of them outside for a make-out session. But today she wasn't feeling it, their approaches felt stale to her.

Her friend Sophia was beside her, casually leaning against the bar. She too was lovely, with caramel-colored skin, long wavy hair dyed blonde, and brown eyes. Tonight she wore a red dress that fit snugly around her hourglass figure and gave a generous view at the deep cleft between her heavy bronzed melons. "I don't mind leaving either. But it's no fun to call it a night," she said. "Maybe we can gather some girls and hang out somewhere. Just the few of us, you know?"

Megan pursed her lips in thought. "My parents are out of town all weekend. We could have a sleep-over! Just like we used to do in middle school, with Saya and Shelley."

Sophia excitedly clasped her hands. "That sounds fantastic! We can go find the others, then meet at the exit. Alright?"

The girls agreed and split up to search the partying crowd for their friends. After a brief search, and having to avoid a few more pressured advances, four girls exited the disco, into the cool night air.

"You came just in time, Megan," Sayako said as they walked down the street. She was a Japanese girl with long black hair and big round glasses that didn't do much to tarnish her beauty. She wore a modest but formfitting black dress over her petite but well-endowed figure, along with black pantyhose on her slender legs. "Jason was hitting on me hard. I thought I'd never get away."

"Hey, Jason is pretty hot though," Sophia answered. "Why the haste to leave?"

"He might be handsome, but he's a tool," Sayako frowned. "He kept telling me how long he's wanted to fuck an Asian girl, as if I'm supposed to find that flattering."

Shelley laughed out loud. "What did you expect from him? Oh well, I much prefer hanging out with you gals anyways." Shelley was the tallest of the four, with long red curls, blue eyes, and freckled cheeks. Unbothered by the chilly breeze, she wore a snug tank top and little short shorts, showing off a lean, athletic body with thick thighs and a generous chest. "Honestly, I just wanna hear what slutty things Megan's been up to since last time."

"Oh, shut up," Megan said, jokingly pushing her aside as the four girls walked down the road together, giggling, towards Megan's house.

***

Some time later, the girls had made themselves comfortable in Megan's dimly lit living room. They had laid out multiple mattresses side-by-side and were sitting in a circle, still wearing their party clothes with only their shoes taken off. They had been engaging in rampant chatting and gossiping for a while now, with no intention of going to sleep any time soon. Of course, it didn't take long for them to reach the subject of boys. With a bit of pushing, Sayako and Shelley convinced Megan and Sophia to talk about their sexual experiences. They had both only done it with one guy each, but that still left them as the more experienced ones.

"You two are suspiciously interested in this," Sophia said after relating a sexual encounter in great detail.

"I knooow, I shouldn't pry." Shelley nervously twirled a lock of red hair around her finger. "It's just, I want to know what it will be like when I decide to do it."

"Is there any reason you're holding back?" Megan pitched in. "Guys would line up for you two, if you asked them."

"I dunno, it's just..." Sayako wrung her hands in thought. "I don't want to fuck someone on a whim just because I think he's handsome. It has to feel right. I don't know what that means yet, but I think I'll feel it when I get there. Is that weird?"

"No, no, I respect it." Megan waved her hand. "I mean, it was nice those couple times I did it, but in hindsight my heart wasn't really in it. I'm sure it would've been even better if it was."

"Ok, so, no pressure," Sophia said with a mischievous glint in her eye. "But if you were gonna lose your virginity today, who would you want to do it with?"

Sayako and Shelley raised their eyebrows in tandem, then both deliberated in silence for a moment as a red blush crept up their faces.

Sophia snickered at their embarrassed expressions. "It's okay, you don't need to have someone in mind. How about we run through the boys in our class and you can judge if they're a good choice."

The girls agreed to this game of sorts, which soon turned into a debate as they each brought up their most likely candidates, only to have someone else bring up a reason not to. All the handsome or confident guys were deemed to be too dense or too conceited, while all the nicer or smarter guys were either off-putting in some way, or already taken.

"Eh, guess there really is no one good. See, this is why I'm a virgin," Shelley said.

Meanwhile, Sayako was silently counting on her fingers. "Oh, we forgot one! Chance. What about him?"

All the girls blinked at each other silently for a bit. They all knew him personally, one way or another, but they'd simply overlooked him. He rarely came to any social gatherings, after all.

"He's a bit skinny, but he's definitely cute," Sophia said. "And he seems like a sweet guy. He helped me cram for that chemistry test a while ago. I hardly knew him, but he offered to help me with my all-nighter anyways. I wouldn't have made it without him."

"You're right, he is nice!" Shelley said. "He helped me out when I hurt my foot during that soccer game. I could've made it home myself, eventually, but he offered to carry me home before the rain started. It was kind of romantic, actually." She smiled to herself.

"Oh, and he stood up for me when that guy was threatening me!" Sayako said. "What was his name, Dirk? The one who called me a chink. Chance got himself a black eye, but he saved me a lot of trouble."

Suddenly, the girls found themselves praising the values of Chance, a guy they'd never considered in a romantic way before. They had a few more back-and-forths, trying to find some fatal flaw in his character, but coming up short.

Then Megan pitched in with a naughty smile. "You know, it's rude to talk about someone behind their back like this. Maybe we should invite him to hang out with us?"

Sophia perked up with a playful smile of her own. "Ooh, yeah, I'm in."

"Wait, you aren't trying to, like, set me up, right?" Sayako protested, her cheeks flushing red. "This whole thing was hypothetical."

"Yeah, we shouldn't give him the wrong idea," Shelley added, blushing just as fiercely.

"Of course not, I just want to see if he's really such a good guy. And if he is, well, you gals can get in line cause I might want him for myself." She pulled her phone from her bra strap and held it up. "Look, I'll ask him to do something a bit embarrassing for me, maybe bring me some tampons. If he actually does, this late at night, we'll know he's the real deal." She paused to see if any of them would swipe the phone out of her hand. Sayako and Shelley looked bashful, but they didn't try to stop her. That was good enough for her, so she pulled up her contacts and looked for Chance's name. "Here we go, then. I'm gonna put on my 'sweet girl' voice, so don't laugh, okay?"

***

Elsewhere, Chance held back a slow yawn as he sank into the old cushioned chair in his bedroom. Perhaps his plan to rewatch the Star Wars original trilogy in one sitting had been too ambitious. He certainly didn't regret spending his Friday night that way - he really wasn't one to go partying like many guys his age liked to do. But now that he was up this late and only partway through Empire Strikes Back, it seemed silly to pull a late night binge for something he could just pause and come back to. Better to be responsible and get some sleep.

He rose from his seat and stretched out, popping his joints. In that moment, his phone vibrated, shockingly loud against the wood of his desk. It made him flinch, trip over the foot of his chair, and stumble a few steps before catching himself. Well, at least that had shaken him awake. When he looked at his phone, the caller ID said "Megan". That gave him halt for a moment. The only Megan he knew was the one from his class. They were on friendly terms after doing a history project together one time. After they both earned an A, she had given him a hug as thanks, one he had enjoyed maybe a little too much. But outside of that, they weren't really friends. So why was she calling at this time?

He answered the phone and tried to sound confident. "Hey, this is Chance."

"Oh hey, this is Megan," said the feminine voice on the other side. "Am I calling at a bad time?"

"No, it's fine. What's up?" He couldn't help but smile a little as he pictured the beautiful girl in his mind.

"I, uhm, was hoping you could maybe help me out," Megan continued. "You see, I'm having some pretty bad... female problems. I can't reach any of my friends, so could you do me a favor and go to the 24-hour-store to get me some, uhm, some tampons?"

By all rights, this shouldn't have been a taboo subject, but his face still flushed at the mention of it. Still, if she was in such dire need, his own shyness about the female body wasn't going to stop him from helping out. "Oh, yeah, sure, I'll get right on it."

"Oh, thank you so much," she said with an odd hint of upbeat excitement in her voice. "I'm so sorry for asking this so late at night."

Chance was already grabbing his keys and wallet off the desk. "No need to be sorry, I'm happy to help. But uhm, can you text me your address? I don't know if I still have it."

"Of course. See you soon, then," she cooed sweetly.

After hanging up, he quickly put on some fresh clothes to make himself presentable, even if he would probably only see her for five minutes. Then he hurried outside, probably a bit more frantically than he needed to, but he didn't want to keep her waiting. He didn't have a car, but his old motorcycle would get him there just fine.

***

Fifteen minutes later, he pulled into Megan's driveway, the rumble of his bike surely announcing his arrival. The living room curtains were closed, so it was impossible to tell if anyone was home. With the pack of tampons under his arm, he ran his fingers through his hair, trying to look a bit less windswept. Then he rang the doorbell, feeling profoundly nervous all of a sudden.

As he waited in tense silence, he heard soft footsteps inside, followed by the clicking of the lock and the creak of the opening door. He had expected to find Megan bed-headed and wearing an oversized t-shirt, in which case she would've still looked quite lovely. Instead, she opened the door wearing skinny jeans and a tight red crop top, showing off her slender stomach and the jutting shape of her ample breasts.

"Ah, Chance. I'm so glad you're here," she said with an eager smile.

She definitely didn't look like she had spent the evening at home, struggling with a bad period. Perhaps that should have made him suspicious, but he was too struck by how damn pretty she was to question it. "Yeah, I, uhm, got you the tampons." He held the box out sheepishly.

"Right, thank you." She took the box, then nibbled on her bottom lip for a moment. "Do you want to come inside for a bit? I want to tell you something."

"Oh, sure, of course," he said, pleasantly surprised that she didn't just send him on his way.

She stepped aside to let him pass, then closed the door behind him. Being alone with her like this felt oddly exciting, but he did his best to ignore any dirty thoughts. She put the box of tampons on the stairs, then turned to face him. "Sooo, I might've lied a little about those 'female problems'."

Chance's heart skipped a beat. For a moment he feared the worst, that this was a set-up for some kind of practical joke. Megan didn't seem cruel enough for that, but he didn't know her that well. "You... lied?"

She showed an apologetic pout. "Don't worry, this isn't a prank. My friends and I just want to have a chat with you. And we wanted to know whether you'd really be so kind as to fulfil my request." She smiled as she walked to the door at the other end of the hall. "Come on, they're in here."

He timidly followed her into the living room, worried about who he might find there. His reluctance turned to pleasant surprise when he saw the other three girls sitting together on a mattress, all wearing equally seductive outfits. They all turned their heads to look at him and smiled.

"You know Sophia, Shelley and Saya, right?" Megan said with a gesture, as if it was nothing unusual.

"Oh, yeah, we've... met," he stammered, now half convinced that this was all a dream. After all, four gorgeous women surely had better things to do than hang out with him, of all people.

"Come join us on here," Sophia said, patting the mattress at her side.

Despite how jarring this all was, she didn't have to ask that twice. He quickly kicked off his shoes, then sat down on the mattress next to her, legs crossed. In the process, he couldn't help but look down at her huge breasts, the soft flesh gently bulging out from the low neckline of her red dress. He quickly ripped his gaze away from those to look up at her pretty brown eyes instead, showing her a nervous smile. Then he looked over at Sayako, with her petite but curvy body on display in a snug black dress, and at Shelley, with her tank top and short shorts that revealed so much smooth, freckled skin. Sayako and Shelley looked a bit bashful themselves, though he couldn't imagine why.

"You guys look amazing," he thought to himself and accidentally said out loud. His face flushed red hot as he cursed himself internally. He really didn't want to open with that, but how could he say anything else when the sight was so overwhelming? "You girls, I mean."

Megan sat down on his other side, a little closer than he expected, completing the circle. "Well, thank you. We just came back from a night out earlier."

"Ah." So they hadn't dressed up just to intimidate him, though it was still working. "So then, uhm, what made you want to talk to me?" He didn't mean to sound incredulous, but it still came out that way.

"Well, we just happened to be talking about you," Sophia said, idly spinning a lock of blonde hair around her finger. "About all the times you helped us out. I'm still thankful for that time you helped me with that chemistry test."

It occurred to him that he had indeed helped each of these girls out at one time or another. That incident with the racist was still painfully fresh in his mind, though he wouldn't have handled it any other way. "Oh, well, I was just doing what was right of course." He slouched in his seat a little, shying away from the attention.

Sophia responded by leaning in, making it even harder not to look down at her cleavage. "So we thought, after what you did, we should at least get to know you a bit. You rarely talk about yourself in class. So, you know, what is your life like? How come you never go to any parties? Do you have a girlfriend?"

"No, I, I don't have a girlfriend," he stammered out instinctively. That part seemed the most important in this particular circumstance. "I guess my life just... isn't that interesting to talk about." He paused for a moment, kind of hoping that might dissuade the topic, but the four beautiful girls just looked at him with curious eyes. He stroked the back of his neck as an excuse to turn his gaze down, away from theirs. "Well, I live with my mom, who needs help around the house sometimes. And I work hard for school, of course. And in my free time I play a lot of video games, probably too many. As for parties, I don't know, I just don't really get invited for those. And if I did I wouldn't really know what to do with them. I've never been good at, you know... talking to girls, and stuff."

There were some muffled giggles from the girls all around, which he hoped were from endearment and not from ridicule. When he timidly looked back up, he saw that Shelley had leaned forward, smiling at him. "You say you're bad at it, but you always seem so gallant with girls. Like that time you carried me home... that was really sweet of you. You didn't seem like someone who's afraid of girls then."

Chance blushed as he thought of something to say in return, but he really wasn't sure how to take a compliment like this. Before he could think of something, Sayako leaned forward as well and spoke up. "But wait. You do like girls, then? Have you ever had a big crush on someone?"

Oh no. He should have expected the classic 'girl talk' question. The problem was, the prime targets of his crushes were all in this room. That was too daunting to admit, so he tried to think of someone else, but it was hard to think about other women when the four of them were right in front of him. Naming one of them and excluding the others seemed like it might make things weird as well, so on a nervous whim he decided to be honest. "No, I, I do like girls. And, well, I've kind of... had a crush on all four of you. Not, not that that was the reason I helped you. I would've done that anyways, I swear."

"Oh?" Megan cooed with a playful smile as she shuffled closer to him, rubbing her shoulder against his arm. "How come you never took your shot? If you'd asked me out after we did that history project, I might've said yes."

Chance felt the urge to shy away from her closeness, not because he didn't like her touch - on the contrary - but because he felt sure that she was being facetious. With Sophia on his other side, there wasn't anywhere to withdraw to except out of the circle, and that would seem like he was shunning their hospitality altogether. So he awkwardly held his ground, feeling frozen by anxiety as the beautiful girl leaned against him.

"Well, I mean, come on, you're all out of my league, right?" he stammered, looking back and forth between Megan and the other three. "You're all so pretty and sweet and confident and I'm just... I dunno, me. All the other guys are into you girls too, there's no way I can compete with them." His face burned red hot as they all blinked at him. He felt like a fool for airing his insecurities like that, but how else was he supposed to answer that question?

Megan broke the tension with a chuckle. "Jeez, Chance, you think too lowly of yourself. Yeah, plenty of guys want me, but it's not first-come-first-served. I want a guy who's right for me." She shuffled even closer, wedging his arm out of the way and really nestling her body against him, pressing her breast right against his side. She had a bra on under her top, but even so he could feel the give of the soft flesh encased inside.

There was no way that she was actually flirting with him. But what else could this possibly be? If this really was flirting, then he had a pretty good idea of what his next move should be. He really wanted to do it, too. He would look like a tool if he did, because this definitely wasn't flirting. But damn it, he had to try, just in case. Better to get it over with and take the rejection, than to keep wondering if he should have tried.