Fortunate Meetings
Copyright© 2026 by BluDraygn
Chapter 4
Romance Sex Story: Chapter 4 - He's a nerd who barely registers on the social spectrum, and she's a prep on the school dance team. A chance meeting in an unlikely place changes both their lives.
Caution: This Romance Sex Story contains strong sexual content, including Ma/Fa mt/ft Consensual Romantic Heterosexual Fiction School Cream Pie First Masturbation Oral Sex Sex Toys
Calling the following morning awkward was an enormous understatement.
Miles woke up that morning to the sound of Maya leaving for her jog. At first, he was a little hurt that she didn’t ask him to join her like usual. But almost instantly, that changed to relief as the scent of her pussy still clinging to his face found its way into his nose. His cock turned to steel in seconds, and he was suddenly glad that he wasn’t trying to jog alongside her. It would have been impossible to hide the tent in his pants.
Knowing that he couldn’t make breakfast in his current state, Miles reached for the lube in his nightstand drawer. He briefly entertained the idea that Maya might come back from her jog and want to continue where they left off last night, so maybe he should hold off on rubbing one out, then realized that he was being way too optimistic. There was also the fact that they still needed to make breakfast and go to school. As much as he loved the idea of losing his virginity that morning, he didn’t want it to be a quickie before rushing to school. Although the idea of Maya sitting in class with her pussy filled with his cum made him even harder, which he hadn’t thought possible. His dick was actually starting to hurt from the pressure, so he gave up and squirted some lube into his hand, hoping that if she were interested in taking things further that morning, his youth would ensure he was up to the task.
Even after getting some relief before crawling out of bed, Miles couldn’t even look in Maya’s direction while making breakfast without blushing furiously. He had to keep finding odd angles to work in the kitchen so that the erection pushing against the front of his pants wouldn’t be too obvious to Maya or, more embarrassingly, his mother.
Maya was in a similar state as she came in from her morning run and sat at the table. She had stood in front of his door for a handful of minutes that morning, trying to knock on his door and wake him up. She finally concluded that facing him was just too embarrassing and left on her own. Once out on the neighborhood’s sidewalks with nothing but the rhythm of her feet hitting concrete and some music playing in her ears, the events of last night kept running through her head. The feel of Miles’s tongue sliding across her pussy and his cum splashing on her inner thigh, the thrill of exposing herself to his hungry eyes, and even masturbating in front of him kept replaying over and over in her head. And she hadn’t expected to be so turned on from watching a guy jack off. Or, more specifically, watching him cum.
The memory of his warm spend splashing on the inside of her thigh sent shivers through her body ... as did the memory of getting back to her room and scraping some of his jizz off her thigh with a finger. She held the milky fluid, which had gotten runnier in the trek across the hall, up to the light and inspected it for a moment before holding it to her nose. The smell wasn’t pleasant, but at the same time, it sent a wave of heat straight to her pussy. She wanted to masturbate with that finger and had to resist the urge to lie back on her bed, scrape the rest from her leg, and smear it all over her sex. Instead, she brought the finger to her mouth and sucked it clean. Again, the taste wasn’t pleasant, she never expected it to be after talking with her friends, but the excitement of tasting a man’s jizz for the first time sent another rush of heat to her sex. She felt a droplet of her juices drip from the lips of her pussy and hit the floor, then looked down at the tiny wet spot in the carpet with surprise, just as a second joined it.
Maya had never been wet enough to actually drip before, and the idea both shocked and excited her. Lying down on her bed, she gathered up the rest of Miles’s cum that hadn’t run down her leg by that point and brought it to her mouth, then reached down and found her clit with the fingers she had just cleaned. Savoring Miles’s taste on her tongue, she quickly worked herself to what might have been her strongest climax yet. As she lay there panting, basking in the afterglow, she closed her eyes for a moment. When her alarm woke her hours later, she was still half-dressed and had a hand between her legs.
With all these thoughts running through her head for the past hour, by the time Maya got back to the house, she was about ready to skip school and drag Miles back into her bedroom. Only Livie’s presence at the breakfast table stopped her.
Miles’s mother stayed quiet and watched the two of them with poorly veiled amusement. It was obvious something had happened during or after their date last night, but she doubted they had gone all the way since she heard Maya leave her room that morning to go on her run instead of Miles’s. However, Livie managed to restrain her curiosity about the night’s events and simply enjoyed the antics of the two teens before leaving for work.
When it came time to get ready, they met in front of the bathroom door and, for the first time that morning, were forced to look at one another. Maya turned bright red and darted into the bathroom, then rushed out a couple of seconds later with all the stuff she needed before jogging over to his mother’s door and disappearing inside. Miles didn’t know if he should be bummed or relieved as he went inside and got ready for school.
The ride to school was filled with blushing glances shared between the two until he pulled over to drop her off.
“We have practice after school, so one of the girls will bring me home. She said, turning her head just enough to see him out of the corner of her eye. “Seeyoutonight,” she blurted out before hurriedly opening the door and exiting the car. She closed the door a little harder than intended in her haste and called, “Sorry!” as she jogged up to her friends.
Kristen was staring wide-eyed at Maya by the time she reached them, but Allie and Liz both looked like wolves who had just found their prey.
“Something happened. You are blushing like a middle schooler with her first boyfriend,” said Liz.
“He’s not my boyfriend,” Maya shot back, even as her face went red yet again. “W-we just went on a date.”
“Good date?” asked Kris.
Maya shivered as a little telltale smile appeared, “Verry good.”
Liz and Allie’s eyes popped open at her response. “Text your ride that you won’t be home until late. Pool party at my place after practice. You. Are. Coming.”
Excitement at the idea of a pool party warred with fear born of the looks her friends were giving her.
“Unless, of course, you have something better to be doing?” asked Liz with a very pointed glance at Maya’s groin.
“No,” she squeaked, “I’ll let him know.”
Miles’s heart sank as he read the message from Maya. He understood that she had practice, but now she was going to miss dinner in lieu of this pool party, which he had not been invited to. Sighing, he dropped his phone in his pocket and made his way to first period.
The day dragged from period to period, and Miles was having a hard time focusing on his classes as worry after worry piled up. Had he made her mad? Had breakfast tasted bad? Was he supposed to have said something on the drive to school? Did he forget to put deodorant on this morning? Heaven knew that he had been sweating most of the drive, and maybe his armpits stunk. Scenario after scenario ran through his head of how he may have completely screwed up his chances with Maya, each more improbable than the last since he ran out of probable reasons before second period.
His worry kept eating away at him, and by lunch, Miles needed some kind of answer. He veered off his normal path to the library toward the cafeteria and turned a corner to see Maya with her back against the lockers as Damon, the guy she mentioned was an ex of hers, leaning over her with a hand on the wall. Maya’s face looked intense, but the grin Damon wore was that of a man who liked what he just heard.
As Damon leaned down, Miles spun around and bolted down the hallway back to the sanctuary of the library, unable to watch him kiss her.
Maya shoved Damon back. “Don’t you dare!”
“Whoa, baby. I just heard that you went on BC. Thought you might be ready to pick up where we left off and maybe take things a little further.”
“I don’t know who the hell told you that, but it’s none of their damn business, and especially not yours! You lost your chance with me when you tried to blackmail me for sex,” she said much louder than necessary.
“Whoa, what are you talking about? I never tried to blackmail you,” he said, stepping back and peering around at all the kids who were suddenly taking a keen interest in their conversation.
“Yes, you did. I needed a place to stay, and you made it very, VERY clear that you wouldn’t consider it unless I slept with you! Thankfully, a better man than you was kind enough to take me in WITHOUT expecting sex, and he has a much, much, MUCH better chance with me than you ever will! Go away, Damon! And don’t ever fucking talk to me again!”
“Language, Ms. Andrews,” said the vice-principal. Those watching the fireworks parted to make a path for him as he approached. “You, go to the nurse’s station and tell her I sent you. I’ll speak with you in a moment. Mr. Weber, in my office. Now.”
“Fuckin’, bitch,” Damon spat after Maya as she stomped away.
The vice principal stepped in between them. “Mr. Weber, one more word and you’re—”
“Go suck a dick, Damon. At least that way, you’ll have a chance of getting a piece of ass,” Maya called over her shoulder while holding up a middle finger.
“Zip it! Andrews! I’ll suspend you too!” the vice principal shouted.
Her middle finger turned into a thumbs-up as she turned the corner toward the nurse’s station.
Liz and Kristen stood among the onlookers, ready to jump in if Maya looked like she needed help. Liz wiped a nonexistent tear from her eye and looked over at Kristen. “Our little girl has grown so much. I’m so proud of her.”
Kris’s stunned look from never having seen Maya act in such a manner slowly faded. “You would be,” said Kris, rolling her eyes as Liz laughed before they headed off toward the cafeteria to tell Allie what happened.
A cacophony of threats from the library staff heralded Chuck running up to Miles’s table. He dropped his backpack on the table while sliding into the chair next to Miles just as the bell ending lunch rang.
“Dude! Did you hear about Damon and Maya?”
“I think I know,” Miles replied, sullen, “and I don’t want to hear about it.”
Chuck leaned away from him, confused. “Dude ... I thought you’d be happy.”
“Do you need to say Dude at the beginning of every sentence? Why would I be happy for them?” snapped Miles as he rose from his seat.
“Happy for them? She told him off, dude.”
Mile’s head whipped around. “What? When I saw them, it looked like they were about to kiss.”
Chuck’s eyes nearly bugged out of his head, and his mouth made an ‘O’ as he started shaking with excitement. Miles’s friend grabbed his arm and dragged him between the bookshelves.
“Duuuuuude, you should have stuck around. She told him off right there in the hallway. They sure as hell didn’t kiss.”
Miles blinked as he tried to absorb the about-face from the scenario that had been playing out in his head. “They didn’t?”
“No, and she said something about blackmail that has Damon sitting in the principal’s office right now. But that’s not the best part, dude. Now, I wasn’t there, so it may have happened a little differently, but Maya told Damon that he lost his chance with her and that you had a much, much, much better chance of getting with her.”
“As much as I want to be happy about that, considering what she’s told me about Damon, you probably have a better chance with Maya than he does.”
“Okay, that’s fair. But I don’t think that I would get the other two ‘much’es.”
Miles looked at him. “Was that English?”
“The guy who told me what happened made it very clear that she said ‘much, much, much better chance of getting with her.’ With the doghouse Damon is in, I may get one of those, but you got all three.”
“I think you’re reading too much into that. But she didn’t actually say my name, did she?”
“‘The guy who was nice and took her in without demanding sex.’ Dude, everyone knows she’s living with you. It’s not that hard to figure out.”
The warning bell chimed, and Chuck darted back to his backpack, still sitting on the table. “You gonna be on tonight?” he asked, slinging the strap over his shoulder.
“Maya has practice, then a thing with the dance team afterward, so probably.”
“Talk to you then, you lucky bastard,” he said before jogging toward the exit. The Librarians weren’t as uppity about his haste since they understood he was trying to get to class on time. Miles picked up his books and strode quickly after him.
“Yo, Benson,” called an unfamiliar woman’s voice as Miles stepped into the hallway after the next class let out. He turned to find Elizabeth Zimmerman. She was on the dance team with Maya and one of her close friends. Miles didn’t know her personally but had heard a few rumors that she had a sharp wit and sharper tongue. She was also one of the only girls in school who was openly bisexual, which, in turn, led to rumors about her being a slut, at worst, or uncomfortably casual about sex at best.
Her clothes reinforced the rumors as the neckline of her white shirt dipped low enough for the fabric of her pink bra to peek out. Hard to notice at a distance, but impossible to miss when she stood right in front of him. Through a monumental force of will, Miles only glanced down the gap between her breasts once before stoically meeting her gaze.
The peach pleated skirt she wore closely matched the skin tone of her legs, and he swore he caught a flash of black panties as she took a step with a little more bounce than the rest as she walked toward him.
“I need to talk with you for a second. In private,” she said in a tone that made it clear this needed to happen, now
Miles wanted to ask why, but then just assumed it had something to do with Maya, since there wasn’t any other reason for her to speak with him. He looked around for a second, wondering if there was any private area besides the stalls in the school’s bathrooms, before suggesting, “The Nurse’s station and library are the closest thing we’ll get to privacy. Unless ... follow me.”
They wound through the throng of students until he came to a closed door. Poking his head inside, he called out, “Mr. Spiner? Can we use your room for a moment?”
The U.S. Government teacher, Mr. Spiner, raised an eyebrow. “Is everything okay, Miles?”
“It’s fine. She just needs to talk to me in private,” he replied, stepping into the room so Elizabeth could come in as well.
“I can’t leave you two in my room alone.”
“Dang,” said Miles.
“Have you heard about the incident between Damon Weber and Maya Andrews?” Elizabeth asked.
“I have, along with instructions not to let him near her, yes.”
“Have you seen the video?”
“There’s a video of it?” Miles asked.
“Of course there is, Benson. By now, it’s probably all over social media,” she replied without breaking eye contact with the teacher.
Mr. Spiner pursed his lips for a moment as if unsure how to answer before saying. “I have.”
“Then this is fine,” she said, “Nothing I say will be a surprise, and I trust that as a teacher, you can keep this conversation to yourself.” Mr. Spiner’s mouth worked like he was about to say something when she rounded on Miles. “Did you tell Damon that Maya is on birth control?”
The question caught Miles completely off guard. “What?”
“Damon found out Maya was on birth control, which turned into the mess earlier. Only a few people knew about that, and you were one of them. Did you tell him?”
Inside, Miles was horrified that someone might think he betrayed Maya in such a way. But more importantly, the question just didn’t make any sense.
“Maya’s living with me, and I’m hoping that something happens between us. Why would I give the ex-boyfriend information that might help him get back together with her?”
“Because Maya told you about the shit Damon already pulled, and you thought something like this might happen. She did a good job announcing how highly she thought of you compared to him. Maybe this was your endgame?”
“You’re giving me way too much credit if you think that’s the case. I saw him leaning down and thought he was about to kiss her, so I went back to the library because I didn’t want to see it. If you think I’m lying, then ask Chuck Hayes. He’s the one who told me what actually happened.”
Elizabeth visibly relaxed as she sighed. “Nah. I believe you. Honestly, I doubted it was you from the start, but I needed to make sure.”
“Why?”
“Because ruling you out leaves only a pair of possibilities, and Allie is going to be pissed as hell when she finds out.”
“Dare I ask?”
“No, but they were the only two who had a problem with Maya living with you.”
“Oh ... those two.” Maya had mentioned that the twins on the team grilled her about him, worried that a nerd like him might hurt their image. Her use of ‘pair’ and ‘two’ instead of something more vague supported his conclusion.
“I must say, Miles, I like you a lot more now that I’ve talked to you. I figured a nerd like you would be whimpering in the corner by now, but instead, you stood up to me. I’m a little bit impressed. Although you lose points for running away instead of throwing yourself in front of Maya when you thought Damon was about to kiss her, I can’t be too harsh. Unless you’re hiding some serious muscles under that shirt, Damon would have given you a serious beatdown.”
“I’m running with Maya in the mornings, but you’re probably right,” he chuckled nervously. Miles had to agree. Damon was all muscle and no brain. The jock would have turned him into a bloody paste in the middle of the hallway.
“She said that when you met to pick her stuff up, you introduced yourselves as if you hadn’t been going to school together for years. I think I understand why.” She held out her hand. “Elizabeth Zimmerman. My friends call me Liz.”
Miles clasped the offered hand and shook it. “Miles Benson. It’s a pleasure to meet you. Can I call you Liz?”
He sucked in a breath as Elizabeth pulled him close and whispered in his ear. “Maya’s been saying a lot of good things about you. Keep doing what you’re doing, and you may end up getting more than you hoped for.”
She backed away and said, “Hmm, I like you, but not quite enough to call me Liz yet.”
Miles just nodded. He had been acutely aware of the softness of Liz’s breasts against his chest, but that paled in comparison to the pressure of her thigh against his cock. As he stood there reeling and trying to figure out exactly what she was getting at, he nearly missed the flash of a tongue playing across her lips or the movement of her hand as she adjusted her skirt.
“I think we’re done here,” said Liz, turning toward Mr. Spiner, who Miles had forgotten was in the room.
The teacher cleared his throat before saying, “Since this concerns the incident earlier. I’ll write you both slips so you aren’t counted as tardy for your next class.”
“Thank you so much,” said Liz in a complete reversal from her attitude when they first came in. “And while I understand you have duties and responsibilities as a teacher, Maya, Miles, and I would greatly appreciate it if you didn’t repeat anything you heard.”
Mr. Spiner looked very uncomfortable and cleared his throat again before saying, “I don’t think anything you said was in violation of school conduct. I see no reason to report it, and on a personal note, my lips are sealed.”
“Thank you, Sir,” said Liz before hurrying Miles toward the door. “Oops,” she said as the tardy excuse slipped from her hand. She bent over to pick it up, but took a tiny bit too long, enough that Miles looked back to see Mr. Spiner’s eyes go wide with shock as he stared at Liz’s backside. A moment later, she stood back up, then bustled him out the door and into the empty hallway.
“What just happened back there?” Miles hissed, confused.
Liz cocked her head and smiled at him. “They say that a woman’s greatest weapon is her body. That’s a load of crap, a woman’s best weapon is here,” she said, tapping her temple. “A woman’s body can be a weapon, but most women treat it like a butter knife and use it to try to smooth everything over.” She leaned closer, and her grin took on a hint of malice that Miles found both scary and sexy. “I use mine like a battleax, and cut through the bullshit and get what I want. Later, Miles.”
“Hey! Before you go ... the pool party tonight?”
“Girl talk. You are most definitely NOT welcome to join us. Maybe the next one.”
“What about Maya’s swimsuit?”
“Allie invites us over often enough that we all have swimsuits at her place.”
“Uh, okay,” he muttered weakly as she walked away. Oddly, he didn’t get the impression she was patronizing him, and he might actually get an invitation in the future.
Daniel Spiner sat back in his chair and let out the breath he had been holding since Liz Zimmerman bent over in front of him.
When she was whispering to Miles, the girl had reached under her skirt and pulled her underwear into the crack of her ass, showing off two beautiful buttcheeks that he would have loved to sink his teeth into. Her little show prompted him to write their tardy excuses to express his appreciation.
But when she bent over ... damn. As one hand reached for the excuse slip on the floor, the other snuck between her legs, quickly pulled her panties to the side, and spread the lips of her pretty little pink pussy. If that hadn’t been enough, the girl appeared to have a thin, almost unnoticeable butt plug inserted into her ass as well. He stifled a groan of loss when she stood back up and all but shoved Benson out the door. The last little look she flashed him didn’t show even a hint of embarrassment or playfulness. He helped her out, and that was his reward. Nothing more. But damn ... what a reward.
Daniel was still fairly young among the teachers at the school. He had only graduated from college a couple of years ago, kept his body fit, and was considered to be fairly handsome. The combination of factors led more than one desperate young woman to show up at his door, willing to do anything for a passing grade or, in a few cases, just a better grade. He also didn’t consider himself a saint and graciously accepted their offers.
His current girlfriend had been one of those girls, but she enjoyed herself so much that she kept coming back even after he raised her grade. Now, she was attending the local college, studying to become a nurse, and often spent the weekend at his place. The minx understood that when they became lovers, he might get more offers like hers. Instead of getting possessive, she suggested they keep their relationship quiet, so he would continue getting them. His girlfriend also suggested putting up hidden cameras in the living room and bedroom for just such occasions. She wasn’t interested in having an open relationship or finding some girl at a bar to bring home. It was something about the idea of a desperate eighteen-year-old having sex with her teacher that turned his girlfriend on immensely, and she loved hearing his detailed stories and watching the videos of him fucking his students as they made love.
He picked up his phone and typed out, “Need you to stop by tonight. Bring your cheerleader uni.”
“You haven’t asked for that in a while. Some poor failing cheerleader making eyes at you?”
“Dance team. But no, it’s not the usual situation. I’ll tell you about it later.”
“Now I’m really curious. See you tonight. Love you.”
“Love you, too.”
The erection tenting his pants now had the anticipation of tonight’s fun mixed with the images of Liz Zimmerman’s ass and pussy to keep it strong. Unfortunately, he had work to do. With a heavy sigh, he tried to ignore his discomfort and went back to grading the papers on his desk.
“Raspberry lemonade for you, and a Shirley Temple for you,” said Beau, handing Maya and Allie their drinks as they lay back in the chaise lounge chairs beside Allie’s pool.
“You’re so good to us,” said Allie, beckoning him down for a kiss.
“I need to be. I’m the only guy to get invited to these parties.” He glanced between Allie and Maya, then over at the pool where Liz and Kris were floating on pool rafts, chatting. All of them wore bikinis, and it was difficult not to react to all the exposed skin. The twins were usually there as well, but declined Allie’s offer to join them after practice. “Not to mention,” Beau continued, “the views are amazing.”
“They’d better not be too amazing,” said Allie as she glared up at him, but with a playfulness in her expression. Maya had heard plenty of these exchanges between the two in the past and knew what was coming.
“They are,” said Beau, “all of you girls are beautiful.” He leaned down and gave Allie a peck on the lips before saying, “But you’re the most beautiful.”
“Kristen, I give you permission to push my head underwater and not let me up if I ever act like that with my boy or girlfriend,” said Liz from the pool. “Listening to those two being all sweet is going to give me diabetes.”
“We’re well aware of what you’d rather see,” said Beau, reaching down to grope his girlfriend’s breast for a second before she batted his hand away.
“Good thing the twins aren’t here. They’d have flipped their shit,” said Liz before rolling off her raft and swimming to the ladder on the side of the pool. A few seconds later, Kristen did the same.
“Speaking of the twins,” continued Liz as she dried off. “We need to have a little chat about them.”
“Sounds serious, so I’m going to assume I’m not invited,” said Beau. “Kris, Liz, would you like a drink?”
“Rum and Coke,” replied Liz.
“Lemonade is fine,” said Kristen.
“Not with Allie’s parents around,” said Beau. “So, a Coke and a lemonade.”
“You’re no fun. I’ll have what Maya’s having.”
“Raspberry lemonade and a regular. Got it. Be back in a few,” he said before heading back into the house and getting a whistle of appreciation from Liz as he walked away.
“Liz...” Allie growled.
“I’m just looking, Al. Your boyfriend has a cute butt.”
“Well, I’m not going to argue with you, but what were you saying about the twins?”
“I had a little talk with Maya’s new loverboy—”
“He’s Not my boyfriend,” said Maya. “Why did you need to talk to him anyway? I’ve been waiting until he was comfortable with meeting everyone.”
“In the vid of you and Damon, he said that he heard you were on birth control,” said Liz as she pulled up one of the other lounging chairs and laid her towel over it before sitting down. “Only a handful of people knew about that. Everyone here, Miles, and the twins.”
“You thought Miles told Damon?”
“Not really, as I couldn’t see any reason why he would. But for my own sanity, I needed to check.”
“And?” Allie prompted.
“He just came right out and said that he’s hoping for something to happen between him and Maya, and that there’s no reason he would give Damon anything that might help him and Maya get back together.”
“What if he knew how Maya would react?” Kristen suggested.
“I brought up the possibility, and he said I was giving him too much credit. Everything about the conversation, from his tone to his body language, said he was telling the truth. I’m certain it wasn’t him.”
“I could have told you that,” said Maya, with a hint of haughtiness. She felt a strange sense of pride that Miles passed Liz’s test, and with flying colors by the sound of it.
“Which only leaves the twins,” said Allie, frowning.
“Or Beau,” said Liz as Allie’s boyfriend approached from the house, carefully carrying three drinks.
“What about me?” asked Beau as he set them down on a table with a large parasol sticking out of the middle. He then handed Liz and Kristen their drinks.
“We’re trying to figure out who told Damon Maya is on birth control. Liz grilled Miles about it and is certain that it wasn’t him,” said Allie.
“Oh ... do I need to leave again?” he asked, picking up his drink.
“Nah, I think you’re fine,” said Maya. “As long as you weren’t the one to tell him.”
“No offense, Maya, but the only girl I need to worry about being on birth control is her,” he said, indicating Allie with the drink he was holding. “Until this moment, I’d forgotten you mentioned it.”
“That rules him out,” said Liz. “Not that I think anyone suspected you in the first place, Beau.”
He raised his glass. “The benefits of being a man and not remembering every teensy weensy tiny little detail I hear,” said Beau before taking a sip.
“I think we’ve just been insulted, ladies,” said Kristen.
“Nah, it’s a superpower you girls have. I’m just glad I don’t have it.”