Graduation Ch. 02

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"Right."

"Yeah, obviously. But feelings and emotions during sex can be so intense that it's easy to forget about the other person. Even when we recognize that person, it's about how he or she makes us feel, or how proud we are for making that person feel a certain way—I am absolutely guilty of this, by the way. I don't want you to think that this is about me lecturing you on how selfish you are. We're all a little selfish during sex. We have to be; otherwise it's just work."

Caleb finished cleaning off a rib and dropped it onto the pile stacked on a paper plate. "So what are you saying?" he asked. "That I shouldn't kick myself too hard for what I did because I'm still learning?"

"Frankly," said Penny. "I don't entirely know where I'm going with this. I'm actually not as experienced as I might seem. I just know that I want you to move on from what happened downstairs because I'm already over it, and I want you to understand..."

Penny stopped for a moment, looked forward, into some imaginary truth that was staring back at her, and laughed softly to herself.

"You know," she continued, "I've been with four other people besides you. One of them long term. They all just kind of took charge in bed, and I was fine with that. Even now, when I'm starting to get a taste for being in control, there's still something oddly comforting about letting a guy just go to town on me. So that's probably how it's going to go for however long this lasts; sometimes I'll want you under my spell, sometimes I'll want you to throw me on a bed and fuck me to death. But as much as you have to meet my needs, I still have to meet yours—whatever those are. See what I mean? It's a partnership."

"So you're asking what my needs are? What I'm hoping to get out of this?"

Penny blinked. She resisted the urge to smack herself. "You know what," she said instead in a self-flagellating tone, "I was just rambling, but that's a really good question to ask. What do you want when you're with me?"

"I suppose 'make you happy' is a cheap answer."

"Admirable, but yeah, cheap. It's all about what I can give you."

Caleb sat with the question for a while; he even turned down the music a bit to better concentrate on it. Penny wanted to tell him not to hurt himself trying to think of an answer, but she was worried it would come off as snarky even though she didn't want him under any undue pressure. Anyway, the time gave her a chance to think of her own answer.

"Honestly," Caleb eventually said, "the best I can come up with is 'the pleasure of your company.' Which makes me sound like I think this is a romantic comedy about following my dreams or something."

"You know what," said Penny, "that's the best I can come up with too."

"Maybe it's just that simple," offered Caleb, washing his hands and mouth with a wet-nap.

"Or, scary version, maybe we don't understand the real answer," countered Penny.

"Maybe," said Caleb.

Penny thought there was a "but" coming, but none ever came. The two just sat in a relatively comfortable silence, finishing their meals, and then Caleb asked the real important question.

"So the long term guy," he said, "that's the one who gave you the biggest orgasm of your life, right?"

"Oh my God, you're STILL on that?"

"Look, just because I know it's a stupid, juvenile thing to compete on doesn't make me want to compete any less!"

"Caleb," Penny laughed, "I know you think you want the title, but I promise you, you don't want the title."

"That only makes me want it more!"

"The biggest orgasm of my life involved me going so hypersensitive that I screamed like a banshee every time I felt so much as a gentle breeze! For, like, 20 minutes!"

Caleb's eyebrows jumped.

"No, it only SOUNDS hot. In practice you will never stop laughing at me."

"I'm kinda laughing at you now."

"Whatever. Yes, he was the long term guy, no, he's not someone you should aspire to. So let it go; you'll never get me there, and you shouldn't feel bad about not getting me there."

"Miss Piper." Caleb caught himself using that name; it only took him a split second to decide that it was fine, and he laid his hand on her thigh. "You realize you're waving a red flag in front of a bull, right?"

"I'm just telling you how it is!"

"All right." Caleb was now off the couch and on his knees at Penny's feet, unbuckling her shorts. "Keep telling me."

"Caleb, your parents will be home in two hours. We have to clean up, I have to get out of here. You are not going down on me right now!"

"Yes I am."

"Caleb, seriously..." She wouldn't allow her shorts to come off, but she wasn't doing much else to fight him, either.

"Seriously..." He started kissing up her thigh.

"Seriously..." His left hand trailed under her shirt, his fingertips gently brushing back and forth across her skin, slowly creeping up to her breast.

"Seriously..." His right hand creeped up her other thigh, up through her shorts, tracing her engorged and increasingly slippery vulva.

"Oh, all right." And she lifted up her hips and slid off her shorts.

* * * * *

Penny was gone with plenty of time to spare. Caleb had changed out of his day clothes and into the ratty gym shorts and t-shirt she slept in. He found some time to do a quick pickup of his room, and he was Overwatching it up with Chris, Jeff, and their friend Porter when he heard a knock on his bedroom door.

"C'mon in," he said after switching his mic off.

The door opened, but no one stepped inside. Caleb glanced over and saw Mom and Becca standing there, looking a little too calm.

"Hey, Caleb," said Mom.

"Hey, Caleb," said Becca immediately after.

"Uh, hey."

"How was your day, Caleb?"

"You have a good day, Caleb?"

"Ooh, your room's clean."

"It looks like a nice, clean room Caleb."

Well, this certainly wasn't creepy and totally suspicious. "Um, what's going on?" Caleb asked, bemused.

"Did you go to 7-Eleven today, Caleb?"

"You treat yourself to a Slurpee, Caleb? At 7-Eleven?"

Cherry Slurpee. Foyer table. FUCK. "Uh, yeah, shit, I got myself a Slurpee and totally forgot about it." Caleb was proud of how cool he was playing it considering that he was screaming on the inside. "I am so sorry. I'll do better next time."

"Oh, don't worry about it, Caleb," said Mom.

"Yeah, don't worry about it. We all make mistakes."

"Sometimes life just gets in the way."

"You feel like a nice Coca-Cola Slurpee, you enjoy some of it, suddenly something comes up, it happens."

"You mean a Cherry Slurpee." Caleb was ready for that babytown frolics bullshit.

Becca giggled. "Yeah, you see? Everybody goofs."

"Everybody goofs, Caleb."

"Everybody."

Caleb and his parents stared at each other, waiting. Neither side expected a confession, but one of them might have started corpsing over this absurd standoff, and that was always fun.

It was Mom who finally backed down. "Anyway," she said, "we're tired, I'm a bit drunk, Becca's a bit...Becca, I'm gonna let you play your game right after I do this." Mom shuffled inside, gave Caleb a peck on the cheek, and shuffled her way back out. "Good night, honey."

"Night, Mom. Night, Becca."

"Night, Caleb." Becca gave him a quick wave and disappeared from the doorway.

When Mom shut the door behind her, Caleb unclenched. He switched his mic back on. "Yo, sorry about that," he said, "had to say goodnight to Mom."

"No sweat," said Chris.

"Hey, do you need me to switch characters? We're a little low on defensive guys, I could roll with Bastion for—"

There was another, slightly more urgent knock on the door.

"Oh for fuck's—What's up, Mom?" He switched off his mic.

"Hey, Caleb, almost forgot." Mom opened the door. "Did you get into my makeup? Maybe experiment with my lipstick a little?"

"...what?"

And that's when Becca literally slid through the door, holding Penny's cherry Slurpee, pointing at the thing that blew Caleb's story to pieces. "Because there's a red lip-shaped smudge on the straw! BAM! BUSTED!"

"SO BUSTED!" Mom added, excited.

Caleb was cringing, shaking his head, kind of embarrassed, kind of loving this.

"Tell me EVERYTHING," said Becca, plopping down next to Caleb on his futon.

"Tell HER everything," said Mom. "Just tell me her name and that you have condoms!"

"Okay, look!" Caleb said, raising his hand to stop everything. He had pretty much given up on his game at this point, but couldn't leave lest he be penalized for abandoning his team. "She's not a girlfriend. She's just somebody I've been hanging out with. You're never meeting her, so don't make a big deal out of it."

"Why not?" asked Mom. "We're entertaining!"

"We only needed three minutes to hash out this whole Columbo routine! We're awesome!"

"It's not about that," laughed Caleb. "Really, I just don't see her ever being that important to me. Neither does she. I promise you, though, when I meet The One, you will beg me to stop talking about her."

"Okay, honey," Mom chuckled. "We're just really excited for you."

"Really? I didn't notice. Oh, and we're not at the point where condoms need to be a thing—" A little white lie, or what he hoped would be one. "—but I'll buy some tomorrow. Promise." Not a lie at all.

"Works for me," said Mom. "And she's treating you okay?"

"Yeah, she's pretty cool," said Caleb. Something came over him, then; he wasn't quite sure why he brought this up, but in retrospect, he probably realized it was worth talking about. "I'm actually a bit too sensitive for her tastes; go figure. But I'm learning, and she's been patient, so...yeah."

"Interesting," said Mom; she was referring to Caleb's answer, but she also happened to describe the look on Becca's face. "All right, seriously, I'm about to pass out. C'mon, Becks, we've tortured him enough."

Becca stood up and walked toward her wife without saying goodnight. Instead, she whispered something in her ear, and she nodded in response. Caleb knew what was happening, and he wasn't that threatened by it; Amelia and Becca had figured out pretty early on that there were some things Caleb was more comfortable telling his loving mother, and other things Caleb was more comfortable telling his cool stepmother. Both understood the value of his confidence; neither would ever seek to undermine it without a grave reason.

"Hey, Caleb," said Becca, "is it cool if I hang out with you for a couple more minutes?"

"Uh, sure. Gimme a sec." He switched on his mic, told his friends he had to pull out (the match had just ended anyway; of course they lost), and quit the game. Mom wished Caleb a good night once more, and shut the door behind her.

"Okay," said Becca, reclaiming her seat on the futon next to Caleb. "So, what's going on with this girl? How far have you gotten with her?"

Caleb shook his head. "I lied. We've gone all the way." Becca didn't even flinch; just nodded her head in understanding. "We've taken precautions," Caleb continued, "not that you want to know about them. She also says she's on the pill, and I trust her, but I get why you'd have concerns."

"Right," said Becca. "It's not about trust, it's about responsibility. If she's cool, she'll get that."

"I really will pick some condoms up tomorrow, and I'll use them from now on."

"Good," said Becca. "Listen, I know I look like I've been out and proud since puberty, but I've had some misadventures while I was learning about myself. And for what it's worth? Condoms aren't that big of a deal. It feels different, absolutely, but the peace of mind is worth it."

Caleb nodded.

"So, since we're on a roll, do you have any questions? Anything you're worried about?"

"Actually, no," said Caleb. "She really is very cool. She knew what she was doing, she was patient with me, she gave a shit about my feelings...we had a great time." Caleb suddenly felt Becca's hand reaching around his back and patting him on the shoulder. She was beaming, and when Caleb went back over his words he realized he was beaming too.

"Good for you," she said. "Not a lot of people are lucky enough to get a first time like that. I'm glad it was with someone who made you feel safe and comfortable."

"Thanks," blushed Caleb. "So am I."

"Let me ask you something, though: When you said earlier that you thought you were too sensitive for her, what—"

"Just a vibe I get," Caleb said. "She says I'm okay, and I mostly believe her, but there's a couple of things that...I dunno."

"That's fine," said Becca. "Sometimes you just get a feeling. Here's my thing: You're no sap. You don't strike me as the kind of guy who dotes a girl to death. Obviously, I could be wrong; maybe you keep telling her shit like 'You're my pookie-wookie honeybear schweetums'"—she said this in a falsetto voice while making a jerk-off motion with her hand—"and you insist on fucking her while listening to 'Hands to Heaven,' I don't know your life."

"What's 'Hands to Heaven?'"

"The most pathetic love song ever written," said Becca, theatrically staring into the middle distance. She shook it off and continued. "My point is, if that's not you...well, the only kind of person who doesn't like to hear compliments is the kind that isn't used to hearing them."

Caleb nodded. "You know, she might have hinted that her ex-boyfriend really sucked."

"Hmm," said Becca. "What I'm thinking of might run deeper than a douchebag ex."

Caleb didn't respond because there was nothing to respond to.

"Look, don't let me scare you. Again, this is purely hypothetical. But if you keep seeing this chick and you get more of a sense of that, don't try to fix her. And don't try to force more info out of her. For now, let her talk to you on her own time, if she even wants to talk to you. You said that this might be more of a fling?" Caleb nodded. "Then the same rules apply: Give her something to measure everyone else against. Just be ready for her to lash out if she thinks you're getting too close, because she will."

"Thanks, Becca," said Caleb. "I appreciate that."

Becca pulled Caleb in and gave him a rare kiss on the cheek. "All right," she said, "no more lectures tonight. I'm ready to pass out."

"Sleep well."

"You too." She had one foot out the door when she suddenly thought of something else. "Actually, one more lecture."

"What's that?"

"Make sure she knows this is a fling," she said, closing the door. "I didn't want to say anything and embarrass you, but it sounds like you managed to land an older woman. And if that's the case, she probably gets what this is better than you do—certainly better than me. But whether she's older or closer to your age, if you somehow manage to slip past her defenses, and then you leave? It's gonna destroy her."

Caleb nodded. It didn't matter that he and Penny always seemed to be talking around that concern—one of many, of course. It was important; if it was already in his mental file, he made sure to underline it then. "That's a good point," he said. "Thanks."

"Happy to help. Feel free to talk to me if you ever need it."

Caleb planned to jump back into Overwatch after his talk, but instead he found himself replaying his time with Penny, focusing more on the conversations and the looks she would give him instead of the usual spank bank material.

Honestly, Penny didn't seem like she was that insecure.

Then again, did they ever?

= = = = =

Thank you so much for reading this whole thing! Before you go, take a couple of seconds and just rate this chapter for me; it's right below the story text. Almost any feedback is good feedback, and the stars are the easiest way to do it.

Of course, if you have a few minutes, you can REALLY make my day by leaving a constructive comment. It can be affirmative, it can be critical, it can ask a question, it can even just suggest a more pathetic love song than "Hands to Heaven." As long as it doesn't have any death threats or personal attacks, I'm not picky! Also, I try to respond to anything that brings up a good talking point, whether it's affirmative or critical, so if you do post a comment, check back in a few days; I might have a response!

Finally, speaking of comments, you can find extended author's notes in the comments section if you want a little insight on what I was going for and what the hell took me so long to write this. Either way, thanks again for your time; hope to see you again soon!

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85 Comments
AnonymousAnonymous3 months ago

I really liked this story. So sad it seems to have been abandoned by the author. No closure is a buzzkill.

Agent_AnonymousAgent_Anonymous3 months ago

I keep coming back to this because it's just so well written. I like the progression of their relationship. It sucks that it wasn't continued and the Author scrapped the 3rd Chapter that he wrote :(

AnonymousAnonymous8 months ago

These two chapters are some of the most underrated on Literotica. I absolutely love them, and Penny and Caleb are awesome. The fact that they have real conversations about what the relationship is and what they want out of it is amazing. It’s not just about a Teacher/Student fetish, and your writing expertly makes that clear. This series is hot, cute, insightful, respectful, and should be in the top five in the “First Time” category as far as I’m concerned. I literally cannot say enough positives about it.

Thank you, this is wonderful! :D

AnonymousAnonymous9 months ago

This is such a great story! The characters and dialogue are done incredibly well, so I really hope you will write more chapters about their relationship soon!

AnonymousAnonymous11 months ago

These chapters are AWESOME. Caleb and Penny feel like real, genuine people, and I love how balanced their relationship is. You can tell they respect each other and there is a genuine bond there, and the physical attraction is great too. I loved Penny’s pop quiz in Chapter One, and Caleb’s training in Two. The dialogue is natural, real, and just flows down the page. Every action during the sex scenes is easily pictured, and the detail is incredible. Both of their feelings are conveyed expertly.

Best First Time story I’ve read on here! Truly excellent! :)

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