Problems and Opportunities

Matt was back in his room, head empty, not yet ready for sleep. He reeked of sex, though he didn’t really care at this point. Anna had blown off all pretense of being cool or casual. He had six unread messages from her, and the banner previews made it clear she was trying to either get him back in her pants or to be her boyfriend. He ignored them, for now, but considered how easy it would be to get nudes...

Matt knew this wasn’t him. He knew he was changing.

But apathy, and lots of sex, clouded his mind.

He messaged Lucy and they talked idly about the day. Nothing special or crazy, just a chat.

Emily let him know she was working the school again tomorrow. He promised to stop by. It would be a fun distraction from school. Was it more than that?

Matt knew he’d had to make a decision eventually. It wouldn’t stay secret forever. This wasn’t the time to compare them all but he only had some many opportunities to fuck around until everyone found out. Although, he could probably keep some of the girls on the side...

He rolled over, bored and still horny. Lucky for him, Melanie chose that moment to message him.

Melanie: “Hey, what’s up?”

Matt: “Bored lol you?”

Melanie: “Same”

Matt waited. What was he supposed to say to that?

Melanie: “So... what’s up?”

Matt: “lmao you already asked”

Melanie: “I know I’m just so bored”

Matt: “You should probably sleep”

Melanie: “I’m in bed at least”

Matt: “me too ;)”

Melanie: “No Lucy tonight?”

Matt: “Too busy :’(“

Melanie: “That’s a shame”

Matt: “Yeah. Oh well, can’t spend every night together.”

Melanie pondered a response. She was indeed in bed, only wearing a tank top and panties. A few minutes ago she had idly started teasing herself, not committing by any means, and she thought about Matt. Now she felt a little silly for talking to him at all. If Lucy found out...

Melanie had been the source of most of Lucy’s sex advice. She thought she was the most experienced in the friend group, anyway, and she was the most comfortable with sex in general. Phone sex seemed like good advice at the time, and Lucy said it went well...

No, she couldn’t do that. That was too much. Too official. But she kept thinking about him and the high praise Lucy had heaped on him...

Melanie: “If only, right? Being alone in bed sucks”

She shot the message off without thinking. It was thirsty and a little desperate, but something about Matt brought it out of her. That wasn’t accurate. His cock brought it out of her.

Matt: “Is that an offer lmao”

No, honestly it wasn’t. She wasn’t going anywhere tonight, but now she had to be honest about why she messaged him in the first place. Was she trying to sext? Not that either, Melanie wasn’t about that sort of thing. That meant the only reason left was that maybe she kind of liked him.

Oops.

Melanie: “lol not to a taken man”

{if Cheat with Melanie=true}

Matt: “I wasn’t too taken last time lol”

{endif}

Shoot. Melanie stared at the phone, unsure where to go with this now. Maybe they could meet up... No, no. She tossed her phone far enough away that she couldn’t message him anymore. It was for the best or she might do some something foolish.

Matt had rolled onto the floor by now. Melanie was flirting around with him but he sensed he wasn’t going to get anything from her tonight so he lost interest. It was getting kind of late, so it was probably time to sleep. First, he pulled up the naughtier pictures Lucy had sent and tugged his cock from his pants.

—

Matt had a dream.

He stood on a cliff surrounded by a raging ocean. Behind him was a pole topped with a beacon that shined a bright light through the dark, stormy clouds. Wind whipped his hair, a frenzied gale swirling around the cliff. A peal of thunder startled him and a single bolt of lightning shot through the sky, illuminating a pair of eyes hiding in the darkness of the clouds.

“There!” A voice sounded, nearly imperceptible from the thunder.

Matt woke with the blaring morning alarm, sitting up quickly and overly dramatic.

—

Matt dragged himself to school with all the motivation of a senior on a cloudy day. He had to check in with Emily at some point today but otherwise it would be a regular day of learning and growth. Matt intended to day dream through most of it.

He planned to see Emily at lunch, but that was thrown for a loop when they ran into each other before classes started.

“Hey, Matt,” Emily said, approaching him. Her hair was tied in a bun atop her head. Her coat hung open and Matt saw her scrubs underneath.

“Emily, nice to see you again,” he said.

“Follow me to my office?” she asked, though her tone made it obvious that it not a suggestion but a command.

He stopped in his tracks and fell in beside her. She didn’t say anything until the door of the nurse’s office closed.

“Are we on the same page?” she asked.

“What? I think so?” Matt said.

Emily stripped her coat, hung it off the desk chair, and plowed her bag on the desk.

“I just think that we aren’t,” she said, “because you don’t really seem to mean what you say.”

Matt stood awkwardly and didn’t say anything.

“You say all these things through the phone, or when we fucked, but otherwise I barely exist to you at all.”

“Okay, well, I’m sorry...” Matt said.

{if In Love with Emily=true}

“Are you? I thought you loved me. But you don’t want to really want to hang out with me.”

{endif}

{if In Love with Abigail=true}

“The other day you said you could see yourself falling for me! But you don’t make an effort to see me at all.”

{endif}

“Well,” Matt offered, “for one, I was going to come see you today.”

“Oh, so the bare minimum. Thanks.” Emily said dismissively.

“Okay, okay, I’m sorry. I want to keep seeing you I’ve just been... busy.”

Emily put a hand on her hip. “I just... I know you’re literally a senior in high school but it can’t be that hard to act as interested as you say you are.”

Matt looked down shyly. “Okay. I’ll do better.”

Emily nodded. “Good. Now get going before we get caught. I’ll see you later today.”

Matt left slowly. He wasn’t used to being upbraided like this. Emily had been cold and unfeeling through the whole conversation. She didn’t give him any opportunity to use emotions to weasel his way out of trouble. He should know better, Emily was sure of herself and hadn’t given any indication of weakness since he met her. Abigail’s threat yesterday was different. She wanted him and would do anything to have him. Today Emily made it clear he needed to shape up or he would lose her, not the other way around.

What a great start to the morning.

Matt kept his head down on the way to his locker, he didn’t need to go through conversation like that this early. Unfortunately, Anna was at his locker already. Matt bristled and prepared for the worst.

“Hey,” Anna said sweetly.

“Uh, hey,” Matt said.

“I just wanted to say hi this morning,” Anna said as Matt started twisting the lock.

“Oh, okay. Well, hi.”

Anna stood shyly for a moment as Matt tried to gather himself for the day.

“So, how is your morning going?” she asked.

“I’m tired,” he said.

“Me too,” Anna giggled. “I’m sure you know why.”

He did, though he didn’t expect Anna to refer to it so casually.

“Uh, yeah. Of course I do.”

Anna blushed a little, “I had a lot of fun, you know.”

Matt just nodded.

“We should do that again, sometime. Or we could just hang out, it doesn’t matter. I had a good time so...”

Matt met Anna’s gaze. More decisions. He could agree and probably see Anna again, just like the others, and dig another hole for himself. The better choice was to kindly reject her advance and focus on his other relationships, or even whittle those down to one. How many women loved him? How many did he love, truly? Despite his behavior he, like all people, was a deep well of emotion. He probably loved them all. He could fuck around and pretend to be cool, emotionless, and in control as much as he liked, but in the private moments with each woman he felt something much different. He should let this one go, focus on what he had and find out what he truly wanted.

But Matt did not.

“Absolutely, that sounds great.”

Anna beamed. “Oh! Awesome! I’ll... I’ll text you!”

Matt smiled and gave her hand a quick squeeze and walked off toward class. Anna watched him go, not believing her good luck without any idea how poor her luck actually was. First because she had only been added to a queue of women vying for Matt’s attention, but also because the entire interaction was witnessed by Mackenzie from just down the hall.

Mackenzie bit her tongue as the two teens walked off and fiddled with her phone. She should say something. Lucy deserved to know, didn’t she? Maybe it was innocent, though Mackenzie had no idea how that could be. She decided she’d confront Anna, first. If that didn’t satisfy her then she’d tell Lucy.

—

Matt hustled toward the nurse’s office the moment his class let out for lunch. Unfortunately his day of being surprised was not over. Melanie intercepted him in the hall.

“In a hurry?” she asked, “Lunch is the other way.”

“I’m not feeling great so I’m headed to the nurse.”

Melanie smirked. “Oh? The new blonde girl?”

“Who?” Matt feigned ignorance.

“Right, right,” Melanie said, “Anyway, you busy tonight?”

“Why?” Matt asked, trying to walk past the conversation. Melanie just walked with him.

“Because I need a ride home after cheer.”

“Uh, okay.” Matt said.

Melanie knew he was interested. It wasn’t hard to tell. His eyes got wide, first of all, and he shook his head funny as if trying to disguise that his initial reaction was delight.

“So if you could give me a ride that would be awesome. I’ll just be really sweaty and stuff and that makes it hard to drive, you know?”

It was thirsty, yes, but Matt was susceptible to beautiful women.

“Okay, sure, I’ll give you a ride home.”

Melanie gave him an exaggerated hug. “Oh, thank you! If you don’t want to go home just stay and watch practice. We’re in the old gym today.”

She meant the previous gym before the brand new one was built a few years ago. In the winter the JV basketball teams used it to practice, but in the fall it was mostly for cheer, dance, and the occasional volleyball activity.

Matt shrugged the hug off and hurried toward Emily. He just couldn’t keep his mouth shut. What’s one more thing on top of all the others?

—

“Matt, good to see you,” Emily greeted the teen as he walked in.

“Hey,” he said, sitting across the desk.

“How’s school?”

“Sucks,” Matt said. “Nice to see you, though.”

“That’s all I get?” She half-teased. “I was expecting more after this morning.”

“Well, I don’t know who’s in here.”

She nodded, conceding the point. “Well, just us. So, try again.”

“Nice to see your beautiful face today, babe,” he said.

“Better,” she smirked.

“Really, though. It’s nice to see you. Did you recover from your weekend?”

“Sure,” she sighed. “You don’t really recover from a three. But, I’m here, making some money, living the dream.”

“I’m sorry I made you feel bad,” Matt said. “I mean it, I’ll do better.”

“How will you make it up to me?” she asked.

“Fancy dinner? I’d love to show you off.”

Emily nodded. “That’s a start. I have something else you can do. Right now.”

Matt perked up. “Oh?”

“Get under the desk,” Emily said.

Matt bit his tongue. “Why?”

“Oh, you think you can ask questions?” she said playfully. “You’re trying to apologize, aren’t you?”

Matt came around the desk and Emily slid her chair out. He tried to kiss her as he passed by but she stopped him with a smile and pointed beneath the desk. Matt clambered into the small space, hemmed in on three sides by wood and the fourth by Emily’s legs.

She scooted her chair back in and squirmed until her scrubs had fallen to her knees.

“You know what to do,” he heard her muffled voice from above.

Matt tugged her scrubs down to her ankles. Emily’s thick thighs obscured her sex and she made him force her knees wider to expose it. He kissed her knees and thighs, crawling over her to position himself to touch her properly. Emily couldn’t see him from above, leaning on her elbows and, from the waist up, a picture of professional behavior. At least, until Matt worked his tongue against her snatch. She shivered, bare legs softly twitching as Matt was able to drag his tongue through Emily’s meaty lips.

Matt held the older woman’s legs apart and dove into her pussy, licking and tasting her as best he could in the cramped space. Emily smiled and tried to keep still. It wouldn’t be enough to get her off. Matt didn’t have enough space and she was a big girl. But it felt nice and that was good enough. Emily bit her lip and stretched her arms over the table, a soft moan the only sound in the room.

Matt’s tongue flicked at Emily’s clit while his hands massaged the soft mounds around her lips. Her taste was intoxicating, like always, sharp but sweet and clinging easily to his tongue. He worked her love button until her knees clenched together and nearly squeezed him unconscious.

“I’ll be right there, take a seat on any of the beds,” he heard Emily saw.

Matt scrambled to help shove Emily’s pants back up her legs and then she was gone, assisting another student. Matt sat in the desk for long minutes, waiting for an opportunity to leave. Eventually her legs returned and he heard her whisper, “They’re laying down, get out quick.”

Matt crawled free, dusting his legs quietly. Emily gave him a quick kiss. “Okay, better get going. Come see me after school if you want.”

Matt left with a heat in his groin and another task to complete. He would be busy this evening.