Fortunate Meetings

The night turned into more of an exploration of each other's bodies than lovemaking after they retired to her room. Maya had a purpose that she was very intent upon, aside from preparing her body for when they finally went all the way. She warned him of her plan in advance, which he was thankful for. Otherwise, he may have gotten annoyed by how she constantly told him to rub here or there and do it softer, then later rub the same spot harder. It felt like she couldn't make up her mind about anything. But as the night progressed and her instructions became less frequent, he appreciated the earlier insight.

But while the constant directions were frustrating, they led to his favorite part. When she pulled out her toy and the lube. The toy wasn't much to look at, just a column of lavender silicone with a tapered, rounded tip. Admittedly, he was a little disappointed that a piece of silicone was going inside Maya's pussy instead of his cock, but at the same time, he understood that she was doing this so that day could come sooner.

Miles knelt beside her on the bed as Maya lubed up the toy and placed it at her entrance, wincing as it touched her.

"Did that hurt?" Miles asked.

Maya thought for a long time about what he felt should have been a yes or no question.

"Have you ever gotten a shot from a nurse who didn't know what they were doing?"

"Yes, it hurt like hell. I'm very confused about where you are going with this, especially now," he said with a glance at where the toy rested against her pussy.

"What about the next time you got a shot? Did you tense up in anticipation of it hurting?"

"I suppose I probably did, but I never gave it much... oh."

Maya nodded. "This," she slid the toy inside of her, wincing again, "doesn't hurt, or at least it doesn't cause pain. But my head is constantly expecting it to hurt like..."

"Like our first time."

"Yeah, sorry."

"Don't ever feel sorry for that. Remember?"

"I'll try to."

Miles leaned down and kissed her. "I won't sugarcoat or downplay how much I want to be inside of you instead of that toy. But if I have to wait a year, or even two, before we go all the way, it will be worth every second."

Maya's face turned crimson. "Jerk, how can you say that when I'm doing something like this right in front of you?"

"Because you're doing it for me," he said, lying down beside her. Miles reached down and brushed her hand away from the toy before taking hold of it and slowly working it in and out of her sex. "Do what you did earlier. Tell me what you do and don't like, so I can make our first time as good as possible."

She gasped quietly before whispering, "Why does it feel so much better when you do it?"

"For the same reason, handjobs are better than masturbating, even if the girl doesn't know what they're doing," Miles chuckled. "You don't need to worry about what your hand is doing and can focus on how good it feels."

Maya opened one eye and looked at him. "And how many handjobs have you had?"

"Me? None. That was from a conversation the guys and I had on Discord."

She grunted skeptically before closing her eyes again. A few seconds later, her hand sought out his cock and began languidly stroking it as she started directing him to try different paces and angles for the dildo.

"Enjoying yourself?" he asked after she had gone quiet and lay there breathing heavily for a while.

Maya nodded. "It's good, but it's not enough."

"How about this?" he asked, pressing his wrist over her clit and rubbing in circles as he worked the toy in and out.

"Better, but still not enough," she said, as her other hand slid down her belly toward her clit. Her hand paused, and her eyes opened to give him a sly look. "How close are you?" she asked, giving his cock a squeeze.

"Not very, but you've been doing that for a while."

Maya rolled toward him, forcing him to let go of the dildo as she scooted into a new position. Lying on her side, she reached behind her and began working the toy in and out of her sex again as she placed the tip of his cock directly on her clit. "There, I want you to cum right there," she moaned as she teased herself with his prick.

Miles grabbed the bottle of lube and put some on his hand before reaching down and stroking his cock. He tried to remember all the things she taught him about touching her with his fingers, but those practices didn't translate well to rubbing her pussy with his cock as he stroked it. Miles settled on an angle that pushed his dick down until it bumped her toy on the downstroke and nudged her pearl as his hand slid up.

"Yes, that's soo good, Miles," Maya moaned as she began rolling her hips ever so slightly.

Miles was actually getting a little uncomfortable. Maya must not have realized just how sensitive the slit on the end of a dick can be because every time his cock slid up to her clit, Maya's pearl felt like it was trying to slip inside his urethra, and the sensation was starting to get painful. Luckily, he found a solution quickly. A slight roll in his stroke sent the tip of his cock into a small loop just below her clit instead of running directly into it. From the increased volume of Maya's moans, she approved of the new method.

Those moans were music to his ears and hurried him toward release.

"Do it, Miles. Let it all out over your girlfriend's pussy so she can play with it."

"Fuck!" Miles yelled as the first jet of milky fluid blasted from the tip of his dick directly onto Maya's clit. Maya rolled onto her back to keep his cum from immediately dripping onto the bed, and Miles tried to follow as best he could, but the last two spurts painted her hip and the crease of her leg. As he still shook from the intensity of his orgasm, Miles watched Maya's fingers begin rubbing her pearl. His arms and legs felt like jelly as he crawled up the bed and placed his softening cock at her lips. She opened her eyes long enough to see the head of his cock glistening with cum before opening her mouth and sucking him inside. The look of momentary distaste was quickly replaced by a lusty moan around his girth as the fingers playing with her clit sped up. He didn't know if Liz's idea that Maya told him about for learning to like the taste of jizz would work, but he was more than happy to help her try.

He regretted that decision almost immediately as Maya's climax washed over her. Along with the rest of her body, her jaw tensed up, and her teeth dug painfully into his shaft. Had he been fully hard, she might have drawn blood. For the next few seconds, it took an enormous amount of willpower not to pull his cock out of her mouth because he knew that would probably make this situation much worse. Maya's body finally relaxed, and she released him as she gasped for air.

"Owwwwwch," said Miles, inspecting his shrinking cock for damage.

Maya's eyes popped open. "What happened?" she asked, her face a mask of worry.

"You kind of bit me." He said, bending his dick so she could see the teeth marks.

"I'm soo sorry!" she said before giving him a sultry look. "Want me to kiss it and make it better?"

Miles presented his cock to her lips and chuckled, "I'm never going to say no to that."

Instead of kisses, Maya took his cock back in her mouth and ran her tongue softly over the indentations left by her teeth. After a few seconds, her goal changed, and she instead took more and more of his cock in her mouth until her nose pressed against his pubic hair. She let him slip free and kissed the individual bite marks before letting him go.

"I hate to say it, but you are going to have to wait a while before I try doing that when you are hard."

"Oh no!" Miles said, waving his hands in the air and speaking in a voice filled with fake worry. "My girlfriend can't deepthroat my dick right away! Whatever shall I do?!" before breaking down into laughter, with Maya joining him a second later.

"Seriously, though, if that never happens, I'm not going to complain. I understand that I'm a big down there. I'm honestly more surprised that you aren't freaking out about biting me."

"There's another thing Liz told us the other day," said Maya, as she reached for a towel they had grabbed earlier and started dabbing between her legs. Miles immediately took the towel from her and took over as she spoke. "She said that two virgins like us are bound to make mistakes. Some will be happy accidents that we add to our love lives, and others will hurt. We can't let the ones that hurt get to us. The first time she had anal sex, a guy slipped out and shoved his dick in her ass. She said that it was insanely painful, but knew that with the right preparation, it could feel good. When she tried it again, later, it did feel good, and now she enjoys it regularly with her lovers. However, she refuses to have sex in the position where the guy slipped unless she has a buttplug."

"Did she tell you the position so we know to avoid it?"

"Yes, but says we shouldn't because it feels really, really good. She also said that with your length, you probably won't have that problem, and how thick you are means you wouldn't have to be at the same angle to make it feel really good for me." Maya sighed. "It seems like every Liz comes up constantly when we talk about bedroom stuff."

"She seems to have given you a lot of good advice that, I feel, we have both benefited from," said Miles as he lifted Maya's legs into the air and wiped down the sweat and fluids from her thighs down to her butt.

"You're making me feel like a baby," she giggled. "But you're right. It's just that... the more she comes up, the more I think taking her up on her offer might be a good idea."

Miles picked up the dildo that had slipped out when Maya rolled onto her back and sniffed it. Detecting no hints of his jizz, he ran his tongue over it, collecting the little bit of her juices left on the silicone before wiping it down with the towel. When he looked up, he saw Maya staring at him.

"What? It tastes like you, and I just came all over your pussy, so I'm not really into getting a drink right from the source at the moment."

"Do you really like how I taste that much?" she asked as he lowered her legs to the bed and began drying himself off. Like when she tried to clean herself, Maya stole the towel and began wiping down Miles's crotch.

"For the very first few seconds, I didn't. But either from pheromones or association, I now absolutely love the flavor. I mean... I did just lick a dildo to get a little more, so I think that should be your answer right there." He sniffed the air. "I think we need showers."

"In a little while," said Maya, tossing the towel to the side. She picked up a small container of breath mints and popped one in her mouth before handing one to Miles. "I want to lay in here with you for a little longer."

"Another of Liz's suggestions?" he asked, holding up the mint before putting it in his mouth.

Maya nodded as she laid back and held out her arms to him.

"Damn, you're beautiful," he said before accepting her invitation and pressing his lips to hers.

---

Miles woke to the feel of Maya's back pressed against his chest and his morning wood trapped between her thighs. Was there a better way to start the day? He couldn't think of one. Maya tried to prove him wrong immediately as she slowly roused, wiggling around while stretching. The feel of her thighs tightening and pussy sliding up his shaft felt exquisite until she relaxed and slid backwards, nearly taking him inside her.

They both jerked their hips away from each other.

"That was close," muttered Miles. "Not that I don't want to, but not like that."

"Yeah, me too," she agreed, looking over her shoulder.

As the memories of last night seeped in, she rolled back into his chest and trapped his cock between her legs again with a contented hum. As she pressed his prick against her sex, she discovered something unexpected.

"Did you have some fun without me?" she asked. "My leg seems to have dried... cum on it, and the bed is wet."

"Not that I remember. I haven't had a wet dream since I was twelve, but considering where my dick spent the night, I wouldn't be surprised. Are you sure it's not a spot we left last night?"

"I'm sure. Want to do it again now that we're awake?" she asked, pressing her butt against his hips in a way that dragged her clit over the top of his shaft.

"I thought I was supposed to be the horny one," he chuckled. "Yes, but no. After what almost happened, I can't trust myself not to slip and end up inside you."

"You're the one who's all hard."

"That's morning wood, and while this," he slid back and then forward again, enough to tease her clit but not far enough back to accidentally slip inside, "is certainly part of why I'm hard. It's also because I really have to piss."

"I've heard about morning wood, but I also heard that guys can't pee when they're hard."

"It's difficult but not impossible. It also depends on how hard I am. Sometimes, there's a little flex, and it's not an issue. Other times, I'm hard as steel, and I end up leaning against the wall behind the toilet because I can't point my dick at it without it hurting. Those days, taking a piss can be very uncomfortable."

"And which of those is today?"

He dragged his cock back and forth across Maya's pussy again. "Definitely a steel day."

Maya scooted forward and then rolled onto her back before reaching under her pillow and pulling out the bottle of lube. "It shouldn't have to hurt to pee. My jaw is still sore from last night, but..." She popped the bottle open and dripped a little between her breasts, then mashed them together, coating the valley between before giving him a look of invitation.

"You're spoiling me," said Miles as he got to his knees and straddled Maya's chest, then laid his cock between the world's most perfect set of tits, in his eyes at least. "I'm going to want this every time I wake up hard as a rock after this."

Maya shrugged before wrapping her breasts around his prick. "Just do it early enough so you don't take time from my morning routine, and I won't mind."

Miles stared down at her. "Really?"

"It's not like I'm putting in a lot of effort here," she said as she wrapped her arms around her breasts and grabbed her elbows. "Just warn me. Liz said it stings if it gets in your eyes."

Miles about choked. Did she just give him permission to cum on her face? Shoving that thought to the side, he started sliding his cock back and forth between Maya's tits.

"When you finish, I'd like to do a little more of, um... what we did last night," said Maya, her eyes flicking between his face and the head of his cock as it poked out from between her breasts.

"I'd be happy to," said Miles as he sped up slightly. He didn't know if this was anything like actual sex, his only experience had been too brief to analyze, but holy fuck did it feel good.

He lasted longer than he expected, but the softness of her skin and the way her breasts molded around his cock quickly got to him. Maya sped things along by occasionally leaning forward and licking the head of his cock as it appeared from between her tits.

"Maya--" he grunted.

Instead of closing her eyes, Maya raised her head and opened her mouth. Each thrust now ended with the head sliding between her lips to be met by her swirling tongue. Miles groaned as he tried to hold back and let this moment last just a little bit longer, but the added stimulation was just too much. A growl started deep in his throat and built into a shout as he thrust forward into Maya's mouth and exploded all over her tongue. For the next few seconds, his entire world zeroed in on the feel of his seed erupting from the tip of his cock, Maya's lips wrapped around his shaft, and her sucking mouth as she tried to draw more out of him. The strength of the orgasm left him shaking enough that she looked up at him with worry.

Still coming down from his climax, he reached under her pillow for the toy they were using last night, then knee-walked down her body and nudged her legs open. Not only was he ready for another taste of Maya's pussy, but after making him cum like that, he was determined to give as good as he got.

------

"Not watching the game?" asked Beau.

Miles stood a short distance from the entrance to the girls' locker rooms, leaning against the wall. He shook his head. "I tried, but I just couldn't get into it. At least in football, there are different formations and patterns that you can visually track to know that something different is happening. Out there," he nodded toward the school gym, "it feels like: Bounce, bounce, bounce, basket. Bounce, bounce, bounce, basket. Bounce, bounce, bounce, basket. I'm sure there's a lot more to it, but with the teams always setting up the exact same way in front of the basket, I can't tell if there's any strategy or if it's just jumping between one-on-one matchups as they pass the ball around."

"That's why I play football. Easier to understand what's going on," said Beau as he claimed the piece of wall next to Miles. "I tried out for basketball our freshman year, but something about the noise the ball makes when it hits the floor hurt my ears. Without that, I can't tell you much about its different strategies and plays. As it is, I'm in the same boat you are. Bounce, bounce, bounce, basket. Bounce, bounce, bounce, basket." He looked over at Miles. "You are NOT allowed to tell any of my basketball-playing friends I said that."

"Your friends haven't exactly been rushing to meet Maya's pet nerd. The sound from the basketball probably created a resonance in your inner ear. I had to ask my mom to get a new microwave because its beeping did that."

"Maya doesn't see you as her pet."

"I know she doesn't, but I'm sure a lot of the people in your circles see me that way."

"You're probably right there. How are the girls doing?"

"Don't know, I haven't checked on them lately."

The locker rooms didn't have a door, supposedly for better ventilation. Instead, there was a short U-shaped hall that opened up into the locker room.

"Allie!" Beau shouted into the entrance. "Do you girls need anything?"

Miles heard some murmuring before she called back, "Can you pick us up some bottled water from the concession stand? We brought some, but they're nearly gone."

"Do you have a cooler?"

"Yeah, just a sec."

"Just so you know, Miles is out here with me."

"Oh! Well shit..."

"Here, I'll take it," came Maya's voice from inside.

"Maya! You can show off in front of your boyfriend all you want, but not in front of mine."

"Your boyfriend has already seen me in a bikini how many times? Panties aren't that different."

"Bikinis don't get see-through when they get wet."

"What...? Oh... Dammit."

"I'll take the damn cooler," growled Liz. "I don't give a shit if they see my pussy."

"I do!" yelled Allie and Maya as Liz walked around the corner. Miles half expected her to be bottomless, but she wore a black sports bra and still had panties on.

"Look at the pervs standing out here listening to girls getting dressed," she giggled. "Here you go," she said, handing the cooler to Beau before turning to Miles. "Get a hold of your buddy. Tell him to be here before our routine is over."

Miles frowned. "He's already crushing on you. If you do anything else with him, he's going to fall hard."

"I'll cross that river when I get there. For now, I need some dick, and my first two options are currently taken," she said with pointed looks at Miles and Beau. "So, be a good wingman and get his ass here."

"Don't you have a strap-on or something you and Kris can use?"

"I do, but it's not the same. That's probably the reason I'm not a full-blown lesbian. Your buddy had a decent cock, and you and Maya getting all hot and bothered has me wanting to train up another virgin."