Senior Year Memories Ch. 44

(Usual Disclaimer Time: Even though this story almost entirely takes place in a high school setting, all the characters in this story are 18 years old or older, and since we're living in the wide wonderful world of porno-land here, where clichés roam free and things might get a little unrealistic from time to time, please remember it's all in good fun. This story is highly serialized, and though it's not 100% necessary to have read the whole story up until this point to enjoy the content of the chapter, it's definitely advisable to understand the many ongoing plots.)

(Author's Note: I want to thank everyone whose votes selected Chloe Marcus as this chapter's SYM Girl, as well as determined some of the other action in this chapter. As always, I want to give special thanks to fellow Literotica author Lil_kitty for her excellent work as my editor and acting as a second set of eyes on this chapter, and for letting me know what did and didn't work; if you get a chance, please check out her work and drop some stars if you enjoyed, she writes some very hot and fun stories.)

Previously, on Senior Year Memories: Working on a profile of the school's Drama Club for the school newspaper in advance of the spring musical, 18-year-old Ryan Collins has started to see his fair share of drama. While helping girls avoid the advances of lecherous triple threat, Micah Burke, with the help of stage crew head Olivia Raine-Goldblum, Ryan set about planning profiles on the four actresses in the running for the musical's lead role. With the help of his sometimes apprentice, Jennifer Cage, Ryan was put into contact with the first of these contenders, gorgeous Middle-Eastern LARPer, Zahra Dashti, in the midst of an adventure with her fellow roleplayers in the park. After some intense foam sword fighting, and some fun conversations, Ryan and Zahra hit it off with some hardcore sex and a nice interview. Though the drama girls have a reputation for being a little crazy, Ryan's confident he'll be able to handle them...

***

When I was younger, the Pruitt house was something like a home away from home for me. Dad knew Mrs. Pruitt through work, and as they were reasonably good friends, she would babysit me fairly frequently whenever he had a night or weekend engagement. Because of this, I spent a lot of time with her daughter Kaitlyn, and while we never exactly got to be best friends in those days, I thought we had a decent friendship, at least one that made the time pass faster while I was being babysat.

As we got older and our interests differed (and Dad reasoned I was more capable of taking care of myself at home), Kaitlyn and I drifted apart. She got to be a popular, bitchy cheerleader and something of a part-time bully to me, while I was a quiet nerd and... well, if you've read this far, you know this part of the story already, so I won't bore you with a recap. The long and the short of it came down to the Pruitt house no longer being one that felt much like home anymore, as I was now a stranger to it.

That changed once senior year kicked off, however, and fate threw Kaitlyn and me together via the tutoring Mrs. Lynn talked me into giving Kaitlyn. After the events that led to Kaitlyn taking my virginity, as well as our frequent tutoring sessions, I was a fairly common presence at the Pruitt house once more.

Our tutoring sessions at her place, though, had a way of generally ending the same way every time, just as they had this time.

I was already down to my t-shirt and underwear by the time Kaitlyn broke our kiss and threw me to the bed. The beautiful 18-year-old, a girl I now considered a confidante and one of my best friends, was barefooted and wearing little more than a tank top and a stretchy pair of booty shorts, both of which did an amazing job at showing off her epic body. Toned from her cheerleading and dance lessons and lightly tanned, Kaitlyn already would have looked mouthwatering even without her gravity defying DD-cup breasts and round ass, but these certainly did help complete the picture. With a gorgeous face that could grace a magazine cover framed by long, silky black hair, she was the very definition of sultry beauty.

That she was looking at me with one of the world's greatest "come fuck me" looks on her face, however, was just icing on the cake.

With her full lips moistened and pursed into a playful little grin, Kaitlyn practically tackled me to the bed, climbing on top of me and kissing me passionately as she ground against my underwear-covered cock. I wrapped my arms around her, enjoying the feel of her body against mine as we made out, each of us groaning softly into each other's mouths as our tongues did battle.

"See?" I grunted softly, leaning in to kiss her neck. "I love it when these sessions go well... you get an education, we both get lucky... really a win-win all around."

"Ugh, do you always have to bring up how good this is for my education? Can't we just fuck?" Kaitlyn teased in her bitchy voice, moaning softly as I kissed her neck again.

"Nah, it's fun for me to bring up your self-betterment," I said, pushing off her bed until I'd rolled on top of her, kissing her again. "Not that you really need it anymore. You could pass your finals with the progress you're showing, in history at least..."

"Yeah, but then we won't get this time together..." she replied, slipping her hand into my underwear and grabbing my cock. She jerked it rather enthusiastically, making me groan as she teased my precum until my cock was nice and slick.

"I doubt you'd be able to stay away from me for that long," I teased. "And, besides, there's more to tutoring than *just* the sex we have afterward."

"Like?" Kaitlyn replied, not giving up on her pace.

"Oh, fuck..." I murmured, kissing her deeply before I got back on the subject at hand. "Well, you can get into whatever college you want."

"Maybe... but I don't wanna think about college right now... or my future..." she said, looking to the side briefly before she gave me a quick kiss. "I want you to fuck me until I scream... or until you can't keep my scream quiet, since my parents *are* in the other room."

Thinking about her mother and stepfather in the other room, I had to agree with her on the benefits of keeping things quiet. "Yeah, I can get behind that plan... even if I don't see why you're not interested in talking about the future."

I slid a hand up underneath Kaitlyn's tank top to squeeze one of her breasts, which I knew wasn't exactly the greatest for spurring in-depth conversations, but I really did enjoy doing. Kaitlyn seemed to enjoy it as well, even if she still had that vaguely thoughtful look on her face.

"Mostly 'cause I don't know what I want out of my future yet? Mom and Grandma, they were both teen moms and that's what defined their lives, and they did alright for themselves, and it sometimes feels like that's gonna happen to me, too... so maybe that's gonna be my life, or maybe college will make sense, or maybe some rich prince will come and sweep me off my feet. I don't know, I just have a hard time planning when everything's so full of different ways it can go... fuck, keep squeezing my tits like that..." Kaitlyn said, sounding impressively focused for a woman who was giving such a good handjob.

I'd already known some of Kaitlyn's family history on this matter, and that Kaitlyn herself had spent much of this year having a bit of an identity crisis that I was somewhat to blame for. She had spent so many years as a mean girl around school, that her attempt at taking a nicer, more mellow year this year had a way of confusing her image of the person she thought she was. I'd done my best to help her through this, but at the end of the day I also understood that a lot of this soul-searching was hers and hers alone, and that if all I could do was be there for her, then I'd be there for her.

"Fair enough," I said, kissing her and then smirking. "But a prince? Really? You've been watching a lot of Hallmark backlog, haven't you?"

"Oh, fuck off, they make good stuff! Sometimes... but, still!" Kaitlyn laughed, rolling us back over so that she was on top. Even though it meant she had to let go of my cock to do it, the fact that it gave her a strong enough position to pull off her top and free those magnificent breasts meant I was far past the point of complaining.

With a playful curl to her smile, she said, "Now why don't we stop talking about the future and start actually *doing* something with the present? Let's get naked!"

What can I say? She was persuasive as hell.

We disentangled ourselves long enough to get fully naked, giving me that beautiful view of Kaitlyn's perfectly shaved and thoroughly moist pussy, while she licked her lips at the sight of my thick, ten-inch erection standing up and proud. It took her only seconds to climb on top and bury my length into her achingly tight cunt, bouncing up and down deliberately enough that we could both have fun, but without making enough noise to draw outside attention to what we were doing.

Knowing how loud that Kaitlyn could get when she was completely unchained, I saw the wisdom in this decision, even if there was nothing more I'd have liked doing than pinning her to the bed and fucking her hard until she couldn't walk straight.

"Fuck... I think we're only getting better at this," I commented, reaching up to squeeze her breasts as she rode me.

Kaitlyn moaned, throwing her head back. "Agreed... fuck, it's like we're made for each other..."

"Seriously," I replied, pulling her in so I could suck on her tits while she rode me. This made Kaitlyn squeal ever so slightly, but she seemed more than happy to have me clap a hand over her mouth to keep this moment pleasantly silent.

Sitting back up with all the superiority of a queen on her throne, Kaitlyn replied, "I won't tell your girlfriends you said that."

I laughed. "Fuck, you can tell them... hell, we can all get together sometime and you can scream it if you want. The five of us together? I think we could all have some insane fun."

She looked off to the side for a moment, still clearly enjoying the moment, but with a little of that thoughtful look again. "I... I dunno, I'm not sure that'd work out. I mean, Brooke and Sarah, you know I adore those bitches, but..."

"Josie?" I suggested, knowing the answer well before I said it.

Biting her lip, Kaitlyn nodded. I'd known that Kaitlyn and Josie had some general distaste for each other, maybe even some bad blood, but I didn't know the exact flavor of it, and aside from her not really being a big fan of cheerleaders in general (save for Brooke and Sarah, of course), Josie didn't seem any keener on enlightening me on what exactly was going on between them. I had suggested Kaitlyn get together with us on more than a few occasions, and it was an idea that had always died on the vine.

Still, I was hopeful that I might be able to sort out their issue eventually, considering how important to me both Josie and Kaitlyn were.

"I don't know what's going on between the two of you... but if I'm gonna make it one of my missions this year to get the two of you in a room together to hash it out..." I said, thrusting up into her and smiling. "And then maybe do you both... because I think you two have got a lot in common in that department."

Kaitlyn laughed, then looked down at me with a cute smile. "I'll say good luck with that, then. Fuck, I'll say good luck with *everything* for you, then..."

She had that little smirk on her face that meant she was holding something back, and that was enough to get me going on finding out just what that was. Pulling her in close again, I locked my arms around her so I could roll on top of her. Then, grabbing hold of her legs, I rotated them until they were propped against my shoulders, allowing me to fold her in half and really give it to her as I slowly fucked her into the bed.

"Ooh, yes!" Kaitlyn hissed, kissing me. "Just like that, just like that... fuck me, fuck me!"

I kissed her, intending to fuck her every bit as hard as I could get away with without getting us in trouble, and doing a damn good job of it I'd like to think.

Not that it was enough to completely distract me from our conversation.

"What was that good luck with *everything* all about," I grunted, pounding down into her with a quickened pace.

Gritting her teeth so she wouldn't moan too loudly, Kaitlyn seemed resistant to answering, but eventually couldn't hold back. "Oh, word travels... and I hear you're in with the drama girls this month. I bet they're all kinds of *fun*."

Having shared a bed with Amy Temple and Zahra Dashti, I could vouch that the drama girls I already knew were very, *very* fun, but I was happy to play it a little coy with Kaitlyn.

"Oh, thoroughly... in fact, I'm joining them for karaoke tomorrow," I replied.

Kaitlyn laughed. "Oh, that I have to see... I mean, not really; no way in hell I'm going out to go karaoke with the drama kids, but, I'd love to see you up on stage... fuck, that would probably be a sight."

"I'm trying not to be insulted by your tone," I grunted. "I think I'll just fuck you 'til we both cum."

I began to thrust into her quicker, building up a swift, measured pace that had Kaitlyn's eyes rolling back into her head.

"I didn't mean to insult you... it's just that we all hear stories about them, and I feel like you could bring your own kind of fun to them (if you haven't already), but, who the fuck cares, just keep doing that, fuck me, fuck me, fuck me harder, come on, please, I'm close, close, yes, yes, yes, yes... FUUUUU-"

I clapped a hand over Kaitlyn's mouth as she came, her body jerking violently under mine and her pussy gushing as it clamped down around my cock. This set off my own orgasm, pleasure overtaking me as I emptied a large load of cum deep in her pussy.

When my eyes cleared, I looked down at Kaitlyn with a sudden swelling of fondness and... yeah, I'll be honest, there was definitely some love there. As ever with her, I didn't know what form that love took, as it didn't seem like we'd ever actually be able to fit in a relationship between the two of us beyond really close friends who had sex all the time, but if all we had was that intense friendship and closeness, then I knew I could handle that particular love.

Kaitlyn looked up at me, so pretty and satisfied and with her own faint look of conflict that made me think that she had something similar on her mind, but before either of us could address anything, or think too hard, Kaitlyn kissed me, quick and fiery and deep and so very satisfying that I probably could've forgotten my own name if it had gone on any longer. It was, in its way, a perfect kind of moment.

Perfect moments, however, rarely have a way of lasting.

Somewhere not far away, a door slammed in the house, and soon there were raised voices, a man and a woman's, hard to hear exactly what was being said through the walls but definitely belonging to Kaitlyn's parents.

Her face soured quickly. "Not this shit again..."

I pulled out of Kaitlyn and climbed off of her, lying down next to her in bed and trying to catch my breath from what we had just done. Beyond that, I also wanted to give Kaitlyn her space if she needed it, but when she instead cuddled up next to me, I wrapped an arm around her shoulders and held her close.

"Again?" I asked, "What's going on?"

For a brief, frightful moment, I was worried that whatever strife there might have been between her mother and stepfather might have come from the fact that I'd had a *lot* of sex with her mother, Cassandra, over a recent long weekend. While Kaitlyn didn't seem to care what had gone down between us, that didn't mean everyone in the Pruitt house had to be as understanding.

"Just... parent bullshit," Kaitlyn said, shaking her head. "Mom's pissed at my stepdad for working too many hours, taking too many trips and never being at home, and even since before then he's always had some, like, resentment over her making more money and being in a better job than him and... well, they've just been arguing a lot lately, and I fucking hate it. They never do it in front of me, but when they think I'm not listening they go at it pretty bad. Sounds like today's gonna be *really* bad..."

She sighed, and unable to do much more than be there for her, I tightened my grip around her shoulders. "I'm sorry."

"Whatever," she replied, sighing again. "I just don't like seeing Mom upset, but I don't like being here for it, either. It's been like this for a few days."

"Fuck, I'm sorry. That's awful," I replied.

"Whatever," Kaitlyn repeated, before smiling a perfectly fake, strained smile. "So, need a date to karaoke tomorrow? I promise I'll be nice to the drama kids."

I smiled wanly. "Josie's coming with me, to take pictures for the paper."

"I see," she said, nodding. "Then can I come crash with you tonight, or will she... she's there too, isn't she?"

I smiled uncomfortably. "Yeah, we were all gonna grab some dinner together... you're welcome to join us. I can ask Josie to be on her best behavior!"

I was pretty sure that this was something I could actually manage, but the way Kaitlyn put on a playful smile and rolled her eyes, it was something I knew couldn't be.

"Hard pass," she said, before kissing me quickly. "But have fun with your girlfriends. And at karaoke! I need to see pictures of you when you get up on stage."

I chuckled, not sure I'd make it that far, but willing to do it if I could bring a real smile to Kaitlyn's face. "We'll see..."

***

Now I've never been one to accuse Regan Hills of being "impressive", but even in that state, I will say that it's always found ways of surprising me. There have been times where I thought I knew every square inch of the town, knew every business, every home, and that I could give a tour of the place off the top of my head without missing anything of note. And yet, whenever life has thrown a new adventure my way, I've somehow managed to find corners of town that I never knew existed, almost as if they had been invented strictly for the occasion of seeing me through the most recent twist in senior year.

Tech Noir was one of these places.

An unassuming black façade on Main Street that I must have passed by a million times without ever really noticing, stepping inside it was like stepping back in time. A half-assed restaurant/bar with barely any lighting that wasn't neon or laser light or reflected from a disco ball, its main attraction seemed to be its two karaoke stages, as well as the private rooms in back where small groups could sing to their heart's content without being overheard.

If I had been in charge of planning this afterschool excursion, I'd have booked one of the back rooms so nobody would have to see me humiliate myself by busting out my singing voice, which I'd charitably call "lackluster."

Given how this was arranged, instead, by a bunch of hyped-up drama kids, everyone was instead parked around the main stage, flipping through karaoke selections or cheering on whoever was on stage. Considering that we were part of a group that only consisted of twelve people, and we were the only customers at Tech Noir at this early time of day, it was genuinely impressive how much noise was being made.

I knew by reputation that these drama kids could bring the crazy, but rowdy was something I was ignorant enough to be completely surprised by. Each time one of them got on stage, you'd have thought that the world was ending for the cheers that they could bring. And while some of them (mostly Micah Burke) had cheers that were distinctly on the fake side, most of them were genuine and meant with the best of intentions as they cheered each other on. And, all in all, it was impressive seeing them show off. Mostly I'd heard about their singing skills secondhand, but seeing them actually bust them out here, I could understand why this particular group of drama kids were front-runners for the lead roles in the spring play.