Senior Year Memories

(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, I swear.)

*****

Previously, on Senior Year Memories: Nerdy 18-year-old Ryan Collins takes his job preparing the Puma Press' haunted house for his school's Halloween Scream fundraiser seriously, and with the help of friend and sexy goth slut Josie Wong, is starting to pull things together. Ryan was nervous when editor of the Puma Press, Nadia Barclay, asked him to seduce a former friend of hers into helping them out, but hesitantly agreed to go along with it. Finding that friend was beautiful cosplayer Mallory Dourif, Ryan was honest with her about asking for her help. Appreciating his honesty and genuine interest in her, Mallory wound up seducing Ryan and agreeing to help the Puma Press with their haunted house.

***

When senior year started, I knew my schedule would be packed. I knew it'd be really busy with the AP classes, tests, SATs and college prep I'd be doing, not to mention the time I meant to spend with Tori and Dad. Back when this was all I expected to be doing, I thought that this year sounded insanely busy.

While that itinerary hadn't changed in the slightest, it had gotten a little more crowded over time than I'd expected.

First came the history tutoring. My favorite teacher, Mrs. Lynn, talked me into that.

Then came working on the Puma Press. My best friend, Tori, talked me into that.

Then came working on the Puma Press' haunted house for our school's Halloween Scream fundraiser. The paper's editor, Nadia, talked me into that.

On top of all of these, came the sex. I guess that's one I blamed on Kaitlyn Pruitt, but an almost supernatural sense of good luck that I wasn't going to argue with had some play in there too.

Since the school year had begun, I'd had sex with nine different women. Four of them were cheerleaders (Kaitlyn, Brooke, Haley and Addison, who was also the Homecoming Queen), one was a teacher (Mrs. Lynn), one was an overachiever (Nadia), one was a goth princess (Josie), one was a nerd goddess (Mallory) and one was my best friend (Tori). I'd started the year as a virgin with no expectation of ending it any differently, yet a chance encounter with Kaitlyn trying to get out of homework threw a monkey wrench in everything and really fucked up my schedule. It was true, that if these were all one-off events, I might've still had some free time on my hands, but they weren't. Kaitlyn, Brooke and Josie all wanted to monopolize my free time (specifically my mouth and cock), and Mrs. Lynn enjoyed the occasional after school tryst. I still had some hopes for second (or third, or fourth...) encounters with some of the others too, not that that helped my schedule.

Don't get me wrong, it wasn't that I didn't enjoy all the sex. Far from it, actually. An overactive and happy sex life with a lot of people I liked and cared about, many of whom actually liked and cared about me in return, was pretty fucking fantastic; it was still just very overwhelming and unexpected. I was only beginning to understand the magnitude of what was happening and what I needed to adjust to, but I was sure that in time I'd probably be able to manage all of these balls in the air without too much difficulty. For now, though, I was taking lessons from Mallory and learning how to multitask.

Take the incident two days after my encounter with Mallory, for instance. I had a lot of tasks to juggle, and I think I did a pretty good job managing them.

Nadia was asking me to look through my contacts for a few attractive girls who wouldn't be afraid of dressing as semi-slutty clowns to entice crowds to come into our haunted house.

Kaitlyn, meanwhile, was long overdue for some tutoring.

And what do you know, when I went over to Kaitlyn's to tutor her, Kaitlyn mysteriously had to send a text, and Brooke showed up not long afterward. No doubt this was Kaitlyn's way of trying to get out of her tutoring, distracting me with a three-way (admittedly not a bad strategy), but she didn't take into account how dedicated I was to my new multitasking spirit.

This probably explained why her face was so sour as she poured over notes and books mere feet away from me and Brooke naked and fucking doggystyle in her bed.

"This is so fucking not fair," Kaitlyn grumbled. She was naked, her luscious DD-cup tits, toned body and sweet pussy on full display, dark, lusty eyes looking out from behind a sheet of silky black hair. She'd clearly expected this afternoon to go different, and maybe even thought that if she were naked she could talk me out of tutoring, but she was sorely mistaken. Her eyes promised punishment, but when I was buried ten inches deep into her slutty blonde best friend, I had a hard time caring about such trivialities

Brooke was a very vocal fucker. Petite and blonde, she made up for her lack of tits as big as Kaitlyn's with a nice round butt that loved to be fucked and the enthusiasm of ten girls. She loved to wear me out and bring me back for more, which her tight little asshole was admittedly rather talented at doing, almost as much as she loved talking during sex. She pounded back against me almost as hard as I was fucking her on Kaitlyn's bed, her twin blonde pigtails bouncing every which way with each impact.

"Well, like, if you'd totally done your studying, we could all be here together sweaty and naked and fucking each other, but you, like, didn't!" Brooke squealed as I pounded into her.

"Yeah, but you're on my bed," Kaitlyn grumbled.

Pounding into Brooke's pussy, I said, "As soon as you can tell me, oh fuck, tell me the significance of the Federalist Papers, yeah, like that, the names of their three authors, and summarize one of the important papers for me, then you can join us."

"This is what Google's for! When the fuck am I going to need this in real life?" Kaitlyn complained.

In a sing-song, pleasured wail, Brooke answered, "Because those who, like, don't learn from history are doomed to repeat it!"

Brooke was never one of the brightest bulbs in the circuit, but she had the most random moments of brilliance that I was seriously wondering if she was secretly smart.

"Nicely said," I replied.

"Thanks!" Brooke squealed, twisting and holding one of her hands up to me. Still fucking her as hard as I could, I returned the high-five.

This didn't improve Kaitlyn's move. "THIS! SUCKS!"

Brooke and I didn't really care about what Kaitlyn did and didn't think sucked. We just cared about sex, and the other point I'd wanted to talk to them about.

"So, I, like thought about what you were proposing about the, ya know, haunted house?" Brooke said.

"Yeah?" I grunted.

"I was thinkin', like, fuck, fuck, fuck, right there, god, yeah, like, that there was this party I might go to before, but since, god, I really feel like I owe ya one for bein' so cool and hangin' out and being one of my new besties and all the really sweet fuckings, I'll totally be there," Brooke said.

"Thanks," I said, pulling her up so I could kiss her while still fucking into her. She kissed me back as energetically ever, before she turned to smile sweetly at Kaitlyn.

"See? If you, like, did your homework, you could be up here with us!" Brooke said.

"Oh, fuck off, like you're doing better in history?" Kaitlyn shot back.

"Hey, I'm not the one in tutoring!" Brooke replied easily.

"You know, god, I could tutor you too," I said, pushing her back down on all fours so I could keep fucking her. I was getting close, and so was she, and I wanted to be in a prime position to take advantage for both of us. I grabbed her by the hips and just went to town, my cock blurring in and out of her tight, hot little pussy, making her tiny little tits and blonde pigtails bounce wildly.

"You would? That'd be FUUUUUUUUUCKINNNNNGGGGGG SWEEEEEEEEEEEEEEEET!!" Brooke screamed as he came, her pussy tightening intensely around my cock.

"OOOOOOOOH FUUUUUUUUUUCK!" I yelled, cum rocketing from my cock and filling her pussy. Even as her own orgasm overtook her, she squeezed my cock for all it was worth, milking every last drop out into her tight, hot cunt. It felt like I'd shot off a gallon or more, and still she squeezed me, finding some way to coax more cum from me.

That was one of many things to love about Brooke: she was insatiable.

I collapsed on top of her on Kaitlyn's bed, both of us laughing and kissing and sounding every bit like a pair of idiot teens who'd just had some wild sex, no doubt. I rolled off of Brooke, and she made a wanting, pouty sound as my cock slid out of her stretched to the max pussy, a river of cum flowing out after.

"You better be saving some of that cum for me," Kaitlyn said, glowering.

"You been hitting those books while we made sweet music?" Brooke asked.

Kaitlyn showed the pile of books and notes she'd been pouring over. "I've hit these books. I've hit them hard. I've hit them so hard in the balls none of them are gonna ever be able to have kids. I may not be able to tell you shit about the Federalist Papers, yet, but I've made these books fucking bleed."

She was glowering and intense, but when Brooke looked to me for confirmation, I shrugged. Brooke returned the shrug. "That's a good enough answer for me!"

Brooke rotated into a seating position on the bed, scooting to the edge and splaying her leaking pussy out for Kaitlyn to see. It probably wasn't exactly what Kaitlyn was looking for when she was asking for cum, but Brooke and I knew about as well as anyone that Kaitlyn was a major league cumslut and wasn't going to let any go to waste. She leaned into Brooke's dripping pussy and licked my cum out of it luxuriantly. Brooke, for her part, loved the attention her pussy was getting, moaning and pinching her nipples while she watched her bestie eat her out.

Come to think of it, I was rather enjoying the show too, but I also had some of that damned multitasking to take care of.

"So, what do you say, Kaitlyn? Will you help us out, dress like a sexy clown for a good cause?" I asked.

Kaitlyn stopped licking my cum from Brooke's cunt, which made Brooke whimper indignantly.

"Get that cock going again and fuck me harder than you fucked Brooke without making me memorize any of that shit and then, maybe, we'll talk," Kaitlyn said.

I thought this over. "Could you at least give me the three authors of the Federalist Papers?"

Without missing a beat, Kaitlyn said, "Alexander Hamilton, James Madison and John Jay."

Disgruntled, Brooke turned to me, "Did she get it?"

"She got it," I nodded. Kaitlyn looked rather proud of herself. Frankly, I was proud of her too. My tutoring method might be unconventional, but I had a feeling I might actually be getting through to her.

"Good," Brooke said, forcing Kaitlyn's face back into her pussy. Considering the vigor that Kaitlyn licked my cum out of Brooke's cuntlips with, I don't think she objected. I sat back and watched the show, wondering for what might've been the thousandth, or perhaps ten-thousandth time how I'd gotten this fucking lucky, when the post-sex haze started to leave my mind and another concern came to me. It wasn't immediate enough that I'd deny Brooke another orgasm, but it was something I had to focus on while I watched to make sure I wouldn't forget.

Once Kaitlyn had eaten all of my cum from Brooke's pussy and given her another orgasm, I asked the first question I needed to ask, "So, Kaitlyn, sexy clown?"

Kaitlyn sighed her irritated sigh. "Fine, I'll be a sexy clown for your haunted house."

"And could you see in your heart about asking some of the other cheerleaders?" I asked, hopeful.

"I wouldn't press my luck," Kaitlyn said.

"I would!" Brooke said. "I'll, like, totally ask around."

"Thanks," I said to Brooke. She smiled at me sweetly. Then, to Kaitlyn, I said, "There's one other thing I wanted to ask you."

"What?" Kaitlyn asked.

"What can you tell me about Rose Ferris?" I asked.

"Why do you want to know about Rose Ferris?" Brooke asked, wrinkling her nose.

"And why do you always have to give her such a hard time?" Kaitlyn asked. Then, to me, Kaitlyn asked, "And why do you want to know about Rose Ferris?"

I could've told the truth, or I could've lied, but in the end they'd have gotten the truth from me, so it wasn't worth hiding. "Nadia wants me to... convince Rose to help us work on our haunted house."

"Convince with your cock, no doubt," Kaitlyn said, reaching out and playfully squeezing my erection.

"Something like that, yeah," I said. "And I know she's a friend of yours, but... I'm sensing a problem?"

"There's no problem," Kaitlyn said.

"Sorta is a problem," Brooke said.

This would've been an odd conversation if the three of us weren't naked, but since we were it made the moment all the more surreal as I tried to wrap my head around it.

"Rose used to cheerlead with us," Kaitlyn explained. "And was almost as big a slut as Brooke and me."

"Almost," Brooke stressed emphatically.

"She was always kinda weird, but that was never really a problem, because everyone's got a weird friend, right?" Kaitlyn said.

"Some of us more than one," I admitted.

Kaitlyn continued, "But then, junior year, out of the blue she decided that cheerleading was 'too mainstream' and quit on us. She'd become..."

"...a hipster!" Brooke said with the same hushed tone of dread and poison you'd normally only hear from someone in a movie talking about one of their dearest loved ones becoming a werewolf.

"A hipster? That's it?" I asked. I knew plenty of hipsters. They weren't all that great, but they weren't all that bad either; they were just kind of their own strange thing.

"Well, when you put it like that, it does, like, sound totally strange," Brooke admitted. "But, I swear, she wasn't the same!"

"People change," Kaitlyn said. "It isn't always a bad thing."

"It is when they're no longer fun! Rose used to be, like, tons of fun, and now she's... a hipster!" Brooke protested.

This was getting us nowhere. I focused on Kaitlyn. "But, you're still friends with her, right?"

"Yeah," Kaitlyn said.

"Well, is there anything you can tell me that'll help me score points with her? If Nadia's gonna try to keep pimping me out to get help, I'd rather it be someone who doesn't entirely hate me or Nadia because that'd make things a lot easier," I said.

"How do you know she doesn't hate either of ya?" Brooke asked.

"Because Nadia didn't warn me, and right after Kaitlyn and me first hooked up, Rose kinda felt up my cock in the school lunch line and didn't go away looking all that displeased, so I think she's interested, but I'm kinda sorta in need of an introduction, and if you could do that, Kaitlyn, that'd really help," I said.

"I'll do you one better," Kaitlyn said, standing up and climbing onto the bed next to us. "I'll set the two of you up. I'll put you two in the same place at the same time and make sure you've got enough time together for you to work your magic. In exchange..."

"In exchange, what?" I asked.

She pushed me onto the bed, climbing over and straddling my face. Kaitlyn asked, "I'm gonna sit on your face so long your breath'll smell like my slutty little cunt for days. Whaddya think of that?"

I didn't have enough time to both think and then verbalize my thoughts, but as Kaitlyn's sweet, slutty little cunt descended on my mouth, her delicious taste hitting my tongue as it probed her depths, I had to say that it sounded like a pretty fair exchange.

***

Though not a particularly large or old town, Regan Hills was large enough and old enough to have one stretch of Main Street called "Old Town Regan Hills." There wasn't a lot of actual old to Old Town, aside from City Hall and the First Regan Hills Church; most of it was just a bunch of trendy indie shops designed to bilk people from neighboring towns out of their money on overpriced "vintage" goods. It wasn't to say that Old Town was without its charms, especially with the Halloween decorations that made every storefront window a blast of orange and black, but it wasn't the part of town I normally liked to hang around.

It was, however, where I was supposed to meet up with Rose Ferris for our "blind date," as Kaitlyn put it. Being that I hadn't ever been on anything resembling a traditional date in the past (not counting accompanying Kaitlyn to Homecoming), I was a little nervous. I mean, I understood that it wasn't going to be an actual date; the way Nadia wanted it and Kaitlyn set it up, it was likely going to be more sex than wining and dining, but it still meant meeting someone in public, possibly even hanging out with them in public, and that had me nervous.

Even with all I'd been through, social situations still made me anxious.

This is probably why I spent more time than I needed to walking up and down Main Street, looking at decorations and hyping myself up for what was going to happen. This is what led to me standing outside the First Regan Hills Church, looking at the poster next to the marquee. Not being the churchgoing sort, it wasn't something that I normally would've paid attention to, but the fire and brimstone look of the poster really caught my eye.

"The 7 Sins of Halloween Hell House! - October 31st"

"Salvation Lies Within!"

"Hosted by the Regan Hills Young Christian Purity Brigade"

Worried for reasons I couldn't fully explain, I took a picture with my phone and shot it to Josie with a joking text.

Me: Competition we oughta be worried about?

I mostly did this as a stalling technique, something to buy me some time before I had to meet Rose. I didn't actually expect as quick a response as Josie wound up sending me.

Josie: As competition? No.

Josie: Might be a problem, though.

Me: Problem?

Josie: You know Sophie Cusack?

Me: Sorta. Brown hair? Huge tits? Always wears the same ugly sweaters, gold cross and purity ring?

Josie: Why am I not surprised that you mention the huge tits?

Me: Because she's got huge tits.

Me: What about her?

Josie: She's been rattling her saber, telling people she's gonna put on a protest outside the Halloween Scream with her Brigade.

Me: And that's a problem? Protests bring attention, and any publicity's good publicity, right?

Josie: I don't think it'll be a problem, but Nadia's worried. If the protest turns anyone away, it's gonna hurt the school. Less money to go around, more losses, you get the picture.

I did, and it wasn't a picture I liked. I was with Josie on this, that it didn't sound like it should be a huge problem, but it was something I thought we probably ought to have kept an eye on.

Me: Anything we gotta do about it?

Josie: Not yet. But if it looks like it might be bad, maybe we should go see if we can talk some sense into Sophie? See if we can get her to change her tune? Anything so Nadia's not on our asses, right?

I thought it over, then typed back a quick response.

Me: It's worth a shot.

Josie: I agree.

Josie: ...

Josie: So, what're you wearing?

Me: Nadia wants me to "convince" Rose Ferris to help us, so, clothes. For now. You?

Josie: [JOSIE HAS SENT YOU AN ATTACHMENT]

Me: ...

Me: Being that that's a close-up picture of you sticking a finger up your asshole, I can't see what you're wearing and must note that you haven't answered my question.

Josie: You know, you can be such a little bitch sometimes.

Me: Try calling me that when I've got my cock shoved all the way up your ass.

Josie: I will.

Me: Promises, promises...

Josie: I can make that promise tonight if you can make it.