Fortunate Meetings
Copyright© 2026 by BluDraygn
Chapter 5
Romance Sex Story: Chapter 5 - 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
Miles didn’t know what to make of the atmosphere at the table. Maya kept blushing every time she looked at him. Considering what happened between them the other day, he wasn’t exactly surprised. But Kristen’s behavior was uncomfortably similar to Maya’s, and he had no idea what could have been said to make her so bashful around him. On the other side of the table, Liz and his mother were in the midst of an animated conversation, talking about his mother’s work and Liz’s school life like they were fast friends and hadn’t met for the first time barely twenty minutes ago.
The other strange thing was the way Maya’s and Kristen’s faces looked. Both of themappeared to have been crying, and while he wanted badly to ask what they had talked about up in Maya’s room to put them in such a state, he knew it had to be something serious, and he should just leave it alone.
“But seriously, Livie, you are a beautiful woman. I’m surprised that Miles doesn’t have a stepdad.”
Miles perked up and cast a suspicious stare in Liz’s direction. “Liz, are you hitting on my Mom?”
His comment seemed to snap Kristen and Maya out of their thoughts as they both turned to look at their friend.
“What?” Liz held her hands out as if presenting Livie to them. “This is not some frumpy thirtysomething. She’s a pretty woman, and she obviously takes care of herself.”
Livie took one of Liz’s hands in hers and said, “Thank you for the compliment. It’s nice to know that I can still turn heads in the younger crowds. However, I don’t swing that way.”
Liz drew Miles’s mother in by the hand and whispered something in her ear that immediately made Livie’s eyes widen, and her cheeks turn pink. The younger woman leaned back and grinned at Miles. “Don’t worry, I wasn’t hitting on her, just testing the waters to see if I should.”
“You’re in my son’s class. I’m quite literally old enough to be your mother,” said Livie.
“I’m very aware of that,” said Liz. Miles wouldn’t call the look she was giving his mother hungry, but it was definitely intense, and she still hadn’t let go of his mother’s hand.
“Maya, Kristen, you two have been so quiet this entire meal. Is everything alright?” Livie asked in an attempt to stop being the center of attention.
Kristen and Maya looked at each other, and after a moment, both of their faces turned bright red as they recalled what had happened before supper.
Liz shoved the silicone phallus at her and said, “Wash it, and when you get back, blowjob practice until supper.” She turned to Kristen, who was doing her best impression of a deer in headlights. “You too, unless you feel like you have enough experience already.”
A few seconds later, Kristen and Maya were across the hall in the bathroom, washing any remaining manufacturing residue or oils from their toys.
“I can’t believe we are doing this,” muttered Maya as she finished rinsing the smallest dildo and moved to the medium size. “And I’m surprised you’re in here with me,” she said to Kristen.
Kristen stuck her vibrator under the running faucet and began lathering it up with some ‘adult toy cleaner’ they had also purchased at Liz’s suggestion. The vibe was slightly larger than Maya’s mid-size dildo, but not as large as the one that was supposed to be similar to Miles. She scrubbed it clean as she answered, “When I was in therapy, I took a lot of time getting to know my body and learning how to pleasure myself. But Liz’s description of how she makes a whole day of just masturbating made me realize that I still had a lot to learn. When she said blowjob practice, I realized that I usually just put my mouth on it and let them do the work. I’m hoping Liz will teach me something that I can use on a future husband.”
“Am I a slut for thinking the same thing about the guy in the kitchen cooking our supper, but who isn’t necessarily going to be my future husband?”
“If it works, it works. If it doesn’t, it doesn’t. Don’t lock yourself in a relationship, like I did. You forget what being happy is because you are in a constant state of trying to make the other person happy, and you don’t allow time for yourself. Either way, I don’t think you’re a slut, and neither would Liz. Yes, he was your knight in shining armor when your life went to hell, so in a way, you feel like you owe him. But he didn’t demand you open your legs in return, so whatever you decide to do with him is because you want to.” She looked at the largest dildo as Maya picked it up and washed it. “Your first time. Oh, you poor girl.”
Maya paused and took a moment to consider the size of the phallus in her hand. “Yeah, it hurt a lot. But I think of it as my sacrifice for what I’ve gained here. Without the pain of that night, I might have ended up in Damon’s bed, paying for the privilege of living with him, or I could have run across someone besides Miles who might have kidnapped me or slit my throat.”
“If you hadn’t lost your virginity to Miles, would your dad have kicked you out?”
“Yes. I was going to tell him that I wasn’t a virgin, whether I lost it or not. That’s how pissed I was at him that night.” Maya finished washing the large phallus and dried it with a towel before looking at the bathroom door with trepidation. “I’m honestly scared of what Liz’s ‘lessons’ might be.”
“Alright, now that your new toys are all cleaned up. Maya, have a seat. Kristen, you get on your knees behind her and look over her shoulder,” said Liz, pointing at Maya’s bed. She took the girl’s toys and laid them out on the towels they wrapped them in for the short jaunt across the hall.
“First things first,” said Liz as she produced a white flexible rod, seemingly from nowhere, and slapped it down in her other palm. It took a moment for Maya to recognize it as the rod that adjusted her window blinds. “We are well aware of the saying that guys think with their dicks. That’s absolutely true, but more so than what you probably believe. As women, we want to know that we are wanted and valued. We like being told we are beautiful and loved. We like it when people do nice things for us, such as give us gifts, give us backrubs, or take long walks at sunset. Guys want all those things, too. But the majority of those things are focused on,” Liz pointed at her groin, “their dicks.
“Now, that doesn’t mean that they are just big cocks. They have thoughts and feelings just like us, but again, it’s focused on their dicks. Ask a woman what she wants after a rough day at work. She’ll say a bath, a nice meal they don’t have to prepare or clean up after, to veg out in front of the TV, maybe a massage. Ask a guy the same thing, and a few of them will list off the things a woman likes, but a large majority will answer with ... a blowjob or some pussy.
“A great example is the weekend I spent at a guy’s house a few months ago. He had some big deal going on at work that he was super stressed about because if he pulled it off, it would put him at the top of the list for a promotion. That Saturday, he was super late coming home. I’d pretty much been there all day by myself and was wearing some skimpy lingerie with no panties. I’d also been edging myself because I wanted my first time getting off that day to be with him inside me.
“He came home, and I called him into the kitchen where I was making some snacks for us. When he walked in, I flashed him my ass to show him I wasn’t wearing any panties. He whipped his cock out as he crossed the room and shoved it inside me.” Liz shivered, and a little smile played across her lips as she relived the memory. “But then,” her tone softened, “he stopped. He wrapped his arms around me and squeezed me so hard I could barely breathe, but we just stood there. After a while, he spun me around, sat my ass on that freezing marble countertop, stuck it back inside me, and proceeded to tell me about his day while only moving enough to stay hard.
“Later, he told me it was the best welcome home he’d ever gotten from any woman. He likened it to a woman’s version of a long, comfortable, soft, fuzzy hug from a giant stuffed animal.
“Now, as I said, not all men are like that. Most of the ones I know would turn into jackrabbits in that same situation. But I’m telling you this to illustrate the importance of a guy’s dick to the guy itself. It’s not just a part of their body. It’s a part of their personality. Tell me I’m a slut with a wallowed-out pussy, and I don’t give a shit. I’m comfortable with who I am and what I do with my body, so fuck them. Give a guy the slightest hint that you don’t like his cock, and it will fucking destroy him even if he knows you think he’s the greatest guy in the world otherwise.
“And that brings us back to...” she tapped the rod in her hand a few more times, “blowjob practice.”
“After all that, I feel more like I’m preparing for war,” said Kristen.
“Okay, maybe the rod was a little too much,” said Liz, whipping it around for a moment so it made cool noises, then giggling as she re-attached it to Maya’s blinds.
Maya and Kristen jumped as their friend spun around on her heel with a mischievious grin on her face. “Maya, what’s the best way to teach somebody a new skill?”
“Watch. Do. Teach,” she replied after a moment. “Watch someone, do it yourself, then teach someone else to do it.”
“Now, while I would very much enjoy calling your boyfriend in here and using him to show you the ropes. I think his first blowjob should be from you, Maya. Sadly, there are too many actors in porn more interested in putting on a good show than actually connecting with their partner and showing their man how much they love and care for him with a stellar BJ. So...” Liz picked up the largest of the dildos and put it in Maya’s hand, then directed her to bring it down to her groin. After coaxing her to spread her legs, Liz pushed it against the fabric covering Maya’s crotch while purring, “I’m going to give you one.”
“You can’t be serious,” Maya breathed.
“Of course I’m serious,” said Liz as she stepped back from the two on the bed. “But while I’ll go through the motions, I’m also going to be explaining why. Before I get started, remember that most blowjobs won’t be like this. Most of the time, it’s just a little bit of foreplay before the main event, or maybe he’s gotten riled up and asks you for a quickie to bring him back down to earth. Also, if he asks for a BJ, never tell him no.”
Kristen gave her a confused look. “What? I shouldn’t have to put out whenever a guy wants.”
“And you don’t. Just don’t use the word ‘no.’ That word is like slamming the door in their face when they’re standing there with a hard-on. As tough as guys act, their egos have a hard time with that. Tell them not now. After you’ve had a shower. Tonight, before bed. I’m not in the mood right now. Would you mind waiting? Say anything but a flat ‘no.’
“On the other hand, if you want them to break up with you, act disgusted by the idea. Guys won’t stick around long if you do that. If they do, they might be little masochists who get off on that or subbie boys who need a good dom, but that’s a whole other can of worms.”
“I wish I didn’t know what you were talking about, but I don’t think I need to worry about that with Miles,” said Maya.
“I think you’re right, and I’m glad for that. I can deal with a lot of different guys, but doormats are some of the worst, right up there with the entitled macho jerks.” Liz struck a pose with her arms crossed in front of her, pushing her chest up and tilting her head to the side while giving Maya a smouldering look. “I’m going to start now,” she said, “You hold that thing in place and watch carefully what I do. Think of what your man is seeing and try to put yourself in my place.”
Liz began swaying to some music in her head as she slowly stripped off her shirt, revealing a red, lacy bra beneath. She then went to work on her pants and lost a bit of her sultry steam as she wiggled comically out of the tight garment. After kicking her pants to the side, leaving her only in her bra and matching panties, she reached behind her back for the bra’s clasp.
“Not that we haven’t seen you naked a hundred times in the showers, but are you stripping all the way?” asked Kristen.
“No, the panties stay on,” she said while slowly stripping the bra off and tossing it aside, casting looks full of desire at Maya. “When guys see a bare pussy, they immediately want to stick their dick in it, and keeping your panties on lets most guys know that you aren’t ready or in the mood for that just yet. However,” her hand slid down over her mound and cupped her sex with a shudder, “as you heard from Beau’s comment earlier, guys like watching us masturbate, and I have yet to run across one that didn’t like me playing with myself while I sucked him off.”
“I have,” said Kristen, “he thought that his cock should be the only thing to give me pleasure.”
“And if you run across another man like that, kick them to the curb immediately. Someone who is that insecure and controlling isn’t worth your time and love. Run. Run far away from them, and don’t look back,” said Liz. She took a moment to get back into her groove before dropping to her knees in front of Maya.
“My only regret is that this hasn’t been inside you yet,” said Liz as she kissed the tip of the dildo.
The cute squeak that escaped Maya was mostly from surprise at what Liz just said, but also because the kiss wasn’t gentle and pushed the base of the dildo into her crotch. She could hardly believe that she was still sitting there holding the phallus between her legs, but it felt too late to ask if Liz could show them what to do from a different position.
“Like everything else I’ve said, what I’m about to tell you is not necessarily true for all guys,” said Liz. “But the head is the most sensitive part,” she said, swirling her tongue around it before taking just the head between her lips and slowly letting it slide out.
Liz grasped the dildo just above Maya’s hands and tilted it upwards. Maya half-grunted, half-moaned as the base pressed against her clit. She tried hard to ignore the pleasure running through her and listen as Liz ran her tongue up the underside and said, “The seam on the bottom is also sensitive, at least more than the top of the shaft, I’ve been told. But that isn’t true for up here,” she explained licking the very top of the underside where it turned into the slit at the tip. The hand holding the phallus had begun a slow stroking motion as she continued. “This is the crown or the flange,” she said, sliding her tongue around the base of the head, “This is where guys are the most sensitive. If you want a guy to get off fast, focus on this part and the underside,” Liz explained before rolling her lips back and forth over the area while stroking more vigorously with her hand.
Maya was breathing heavily by this point and was having a difficult time holding in her moans each time the base of the dildo pushed against her pussy. It didn’t help that she had started to smell just how aroused she was and had noticed two other distinctive scents filling her bedroom as well. Liz was expected since she had been rubbing her sex during her lesson. Kristen’s arousal was a little more of a surprise, but only for a moment, until Maya thought about what was happening between her legs. It would be nearly impossible not to get turned on watching this.
Liz let the cock slip free of her mouth and said, “Now, for the balls...” Liz stuck her tongue out and slid it all the way down to the base of the shaft, forcing Maya to hold the phallus in place with a ring of her fingers. Lis dragged her tongue over the fake balls and planted little kisses on each before saying, “You need to be careful with these. Some guys like them smacked around, while for others, you have to be super gent ... fuck,” she said, putting her head down as she shuddered for a moment. After a second, she looked up at Maya and Kristen with a pleading expression. “Maya, Kris ... I didn’t think I would let it get this far, but do you two mind if I get off? I’m sorry. I was trying to hold back, but...” she drew in a long breath through her nose before focusing on Maya, “you just smell so good.”
Kristen rested her chin on Maya’s shoulder and moaned, “If she does, I am too. It’s up to you, Maya.”
“Are you playing with yourself back there?” Maya hissed and received an affirmative moan from Kristen for a reply. Maya wasn’t sure how she felt about watching Liz get herself off, or Kristen using her shoulder as a headrest while she did the same, but telling either of them no at this point seemed cruel.
The look of happiness on Liz’s face when Maya agreed was interrupted by another full-body shudder. Liz picked up the small bottle of flavored lubricant they had also purchased and squirted some in her hand before using it to coat the dildo as the other slid down to her crotch again, this time slipping beneath the fabric of her panties. “Now, for a quick glimpse into the advanced class. Deepthroating.”
Liz dove in to continue giving attention to the dildo’s balls and get a few more lungfuls of Maya’s scent, which gave Maya a quiet little thrill as well, before dragging her tongue up to the tip once again.
Maya’s breath caught in her throat as Liz looked up and stared deeply into her eyes while her lips parted and took in the tip of the fake dick. She grasped the slickened shaft with her hand and began jerking it while bobbing back and forth like it was a real cock, each time going a little bit deeper. The stroking was doing wonderful things to Maya’s sex. The pressure wasn’t as intense, but now she got the added vibration of Liz’s hand sliding over the phallus’s veined surface.
The tip of the dildo bumped against the back of Liz’s throat. She smiled around the cock in her mouth before taking a deep breath and pushing forward. Maya felt Liz’s throat make a swallowing motion before giving way and taking the dildo all the way to its base. She nearly pulled the phallus from Maya’s fingers as she began rocking back and forth, fucking her throat with it while her arm shook as she played with her pussy.
Kristen’s chin dug into Maya’s shoulder as her body tensed up, and she let out a long but quiet moan, her eyes never leaving Liz’s body as the woman impaled her throat over and over in her desperation to climax. Seconds later, Liz took the entire length of the dildo and held it there as her body shook and heaved. Had she been closer, the pressure and vibrations against Maya’s sex would have likely pushed her over the edge. Instead, she was left frustratingly close to her own orgasm as both her friends recovered from theirs.
“Okay...” panted Liz after she released the toy from her throat and took a minute to catch her breath. “Go wash this beast off and get back here. You got to watch. Now it’s time to do.”
Maya whined with disappointment as she pulled the dildo away from her pussy.
Liz shook her head. “You have a boyfriend who will happily lick you until you come. As jealous as I am of Miles, I’m not going to take from your time with him later. Shoo,” she said, waving Maya out the door.
“I’m surprised, Liz,” said Kristen once Maya had left. She leaned back to let Maya get up and leave, but still had a hand in her pants.
“So am I. As much as I want to taste her pussy, I can’t believe I just turned down a perfect opportunity.”
Kristen pulled her hand out of her pants and revealed fingers wet with her juices, “Interested in a different flavor?”
Liz glanced at the door before leaning forward and taking her friend’s fingers in her mouth while the hand in her panties worked her quickly to a second climax.
When Maya entered the room again, she waved a hand under her nose. “Whoo, it’s musty in here.”
Liz took a deep breath. Maya noted that the sight was only slightly less impressive now that she had her bra back on. “Yeah, I love that smell. Even more when it’s with a guy. There’s a sharpness in their sweat that I don’t get from being with other girls, and the mixture of girl juice and boy cum is like the cherry on top.”
“I can’t say I ever cared much for the scent of sex,” said Kristen. “But then, it’s not like I was having a fantastic time when having said sex.”
“Find a man who leaves you a panting, sloppy, orgasmic puddle, then cuddles you until you calm down, and you might change your mind. But I get what you are saying. A lot of people don’t like the smell of sex. Now, on to the next part. Both of you pick a position, either on the bed or on the side of it, like I was. It’s time to practice what I showed you.”
Maya and Kristen’s faces turned beet red as they shared a look reminding each other of their practice and the numerous times they accidentally gagged on their respective toys. Maya much more than Kristen, who had at least some experience already. By the time Miles called them for dinner, both girls looked like they had been crying.
“Everything’s fine, Ms. B,” said Kristen as Maya hurriedly nodded in agreement.
“Not to worry, Livie, it was just a bit of music practice,” said Liz, only to be met by confused looks from everyone at the table. She seemed to find their confusion funny, giggling at their expressions.
“It must have been some intense music practice. I thought you were talking about something important the way your faces looked,” said Miles.
“What do you mean by how our faces looked?” Maya asked.
“You and Kristen looked like you’d been crying.”
“We weren’t crying, and forget you ever saw that,” said Kristen with a stern glare.
“Please,” added Maya.
“If that’s what you want. I didn’t know you were into music, but I suppose it makes sense since you are on the dance team.”
“I’m not,” said Maya.
“We aren’t,” confirmed Kristen, “Liz is messing with us. More importantly, this is absolutely amazing, Miles. I’ve always wondered what the chicken katsu they make in anime tastes like.”
“I never thought putting soy sauce and mayo on shredded cabbage could taste good,” said Maya, picking up a little bit on her fork.
Lis speared a piece with her fork and held it up. “Part of me wants to say it’s a really fancy fried chicken patty,” she said, turning it back and forth. “But I know damn well I’m never going to get anything this good at KFC. This is every bit as good as Maya told us it was.”
“Did you doubt my son?” asked Livie.
“Until I went and busted his balls about something that happened at school, I didn’t know who he was. And with the way Maya’s been talking him up since she moved in here, it had a little bit of a ‘too good to be true’ vibe. I wouldn’t say I doubted your son. More like I doubted Maya’s image of him.”
“And,” Livie prompted.
“He’s a nice guy, not a doormat. Obviously has a thing for Maya but isn’t being pushy about it.” She held up the piece of Katsu, “And he’s a damn good cook.” Liz took a bite of the fried meat on her fork and chewed a few times before mumbling around her food, “So far, I like him.”
“Maybe we could convince Allie to let him come over and make snacks at our next pool party?” Kristen suggested.
“I like the idea,” said Liz, “Allie usually handles all the snacks and drinks. Since Beau has opted to become our bartender, I’m sure she wouldn’t mind handing over the snack part to Miles. Keep in mind,” she pointed at him with the remaining Katsu on her fork, “Your only payment for this will be ogling us three as we swim, prance around, and lay out in the sun wearing only bikinis. Allie, too, but since she and Beau are a thing, you might not want to ogle her too much.”
“Bartender?” asked Livie with disapproval. “I can understand a glass of wine with dinner, but you all are too young to be drinking.”
Liz shrugged. “Honestly, Beau is a shitty bartender. I keep asking him for Rum and Cola, and he only ever brings me the cola.”
“But he makes a really good strawberry lemonade,” offered Maya, coming to Beau’s defense.
“I’m pretty sure that was raspberry,” Kristen whispered.
“Oops, it was, wasn’t it?”
“I rest my case,” said Liz.
“Now, what was this about busting my son’s balls?” asked Livie.
“Someone at school found out something about Maya that they had no business knowing. I needed to be sure it didn’t come from him.”
“She didn’t actually think it was me, Mom. She just needed to be sure,” Miles explained.
“Did you figure out who it was?” Livie asked.
“Unfortunately,” said Kristen, looking warily at Miles.
“I think I already know who it was,” he said. “That list was pretty short to begin with.”
“Which means we will likely lose two members of the dance team,” added Maya.
“This thing they found out was that bad?” asked Livie, looking around at the subdued girls at her table.
“It’s not that it was a big deal by itself,” Maya explained. “It was just that I was on birth control now. But they told one of my ex-boyfriends in hopes he and I would get back together.”
“Her ex is on the football team and of a higher social standing than Miles,” Kristen continued. “We think they believed Maya dating Miles would damage their social status.”
“So now they are going to get kicked off the dance team and will have to suffer through that loss in status. Sounds smart,” said Livie, her voice dripping with sarcasm.
“Enough about them,” said Liz. “Livie, when is your next trip out of town?”
Miles’s mother narrowed her eyes in suspicion. “Why do you want to know?”
“Because Maya didn’t get to come to our sleepovers growing up, thanks to her dad. So, we want to have one with her now that she’s out of his house. Preferably without adult supervision.”
“Technically, we’re all adults,” mentioned Kristen.
“I get what you mean,” Livie chuckled. “But what about Miles? Guys aren’t usually invited to sleepovers.”
Liz waved off her concern. “Him? Pfft, we’ll tie him to the bed and have our way with him, only letting him up to make us food.”
“Liz, there was not enough of a joking tone in your voice when you said that,” said Miles’s mother.
“Fine ... we won’t tie him to the bed, and Kristen and I will keep our hands to ourselves, but I can’t make promises for Maya.”
Livie glanced over at Maya, who was blushing red and refused to meet her gaze. “I suppose that’s acceptable. I’ll let Miles or Maya know my travel schedule so you can make plans. You know, it probably wouldn’t matter much if I were here or not.”
“Yes, it would,” said Liz. “If you were here, I’d be too distracted to have fun with my girlfriends.”
Livie’s cheeks turned pink as she returned the younger girl’s challenging stare. “Hmmm, maybe you’re right.”
“You were really laying it on thick with Ms. B in there,” said Kristen once she and Liz were on their way home.
“I was still wound up from blowjob practice. I still am, really,” Liz replied as they turned onto the main road.
“I am, too. Do you think we could help each other out?”
Liz was silent for a moment before pulling into the empty parking lot of a store that closed earlier in the day.
“Is that a no?” Kristen asked.
“It’s not. It’s that I’m bad for you, Kris. You don’t need someone like me. In all fairness, after the shit you’ve been through, you need someone like Miles, who will love and cherish you. I ... I will hurt you. I can’t be that person. I love sex and the pleasures of life too much, and eventually, I’d have a weak moment and hurt you. Even as I was giving my demonstration earlier, I hoped and prayed that Miles would walk in and shove his cock in my pussy. And I’ll tell you now, I’m hoping that I can talk Maya into sharing once they’re sleeping together regularly. I don’t want to steal him away from Maya. I just know that it’s going to be new and different and feel good. I will happily take you home and make love to you, Kris, but if you ever start falling in love with me, you need to call it off before you get hurt. We grew up together, and I care about you too much to do that to you.”
Kristen put a hand on the far side of Liz’s face and pulled her over into a long, soft kiss.
“I appreciate your warning,” she said after releasing her stunned friend. “But watching you and Maya showed me something very important.”
“And that is?”
“I love men. Watching you was insanely hot, but I wanted to be down there instead of watching you, and, don’t tell Maya this, but in my head, I was thinking of Miles sitting there instead of Maya.”
“With you blowing him.”
“Yeah ... Playing around with girls might be fun, but I think in the end, it’ll have to be a guy if I ever get married.”
Liz smiled. “My place then? I’m living in that apartment my parents built over their garage for my brother when he was in college. We can have all the privacy we want.”
“Sounds fun.” As they pulled back out onto the road, Kristen asked, “What about Miles’s mother? Are you going to try to sleep with her?”
“Abso-fucking-lutely. I wasn’t kidding when I told her she was beautiful.”
“Don’t you worry about her falling for you?”
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