Senior Year Memories Ch. 18

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Healing wounds with a December naughty & nice threesome.
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Part 20 of the 48 part series

Updated 02/09/2024
Created 04/18/2018
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(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 some of the ongoing plots.)

(Author's Note: I'd like to again thank MisterWildCard for acting as a second set of eyes on this chapter and for his honest editing and fantastic suggestions. Please check out his story, "Brooke's Wild Ride" in Erotic Couplings, as it acts as a canonical side story to Senior Year Memories starring Regan Hills High's favorite blonde cheerleader.)

Previously, on Senior Year Memories: Thanksgiving was a day that 18-year-old nerd Ryan Collins would never forget. He was looking forward to a day of good food and awkward family conversations after accepting the invitation to his best friend and longtime crush, Tori McNeil's, house. That he had had sex with Tori's mom, Lauren, and befriended and made out with Tori's hated older sister, Rachel, were secrets he meant to hold close to his chest, especially after knowing that taking things any further with Rachel would make a bad situation even worse. However, after meeting Tori's new girlfriend, April, Ryan broke off and shared a drink with Rachel. Commiserating over how out of place they both felt here, they let their passion overcome their better sense and had sex, only to be caught by Tori. After a long, loud argument, Tori kicked Ryan out of her house and her life, possibly forever.

***

There's a line in a not-great-but-not-terrible Matthew Broderick and Marlon Brando comedy called The Freshman that's always stuck with me.

"There's a kind of freedom in being completely screwed... because you know things can't get any worse."

I'd always liked that quote, but the problem with it is it's hard to tell when you've hit that spot where you're completely screwed. Too often when you think that things can't get any worse, they find a way of doing just that that can take you by surprise, so I try to avoid thinking that I'm completely screwed. That way if things get worse, I can't be surprised.

It was hard to keep thinking this way after Thanksgiving. That my oldest friend... that Tori, wanted me out of her life, that felt like being completely screwed. She hadn't spread around any of what happened between me and her mom and her sister, though whether it was to protect Lauren or me or her dad or Rachel (unlikely) or herself, I couldn't tell you. I'd tried daily for close to a week to try to talk to her afterward, only to get shut out every time.

I tried to tell myself that this wasn't that different from the times Tori and I had lost touch earlier this year, that if I kept at it and let heads cool down that we'd get back together and be friends again, perhaps with the help of a few more screaming matches, but the utter silence I was getting felt more conclusive than usual.

This really was it. This was the end.

If you've been reading so far and remember the Kyle Bowman incident, you can probably guess that I shut down for a little while after this; for days afterward it felt easier to just stay quiet and avoid the world and hope that that would keep everything from falling down all around me while still telling myself that this was the worst time of my life. For a time, even, that worked, but that was only sustainable for those first few days after Thanksgiving before having to go back to school.

Like in the days after Kyle Bowman attacked me, it seemed like pushing people away would be easiest, but unlike those days the people around me weren't so apt to let me push them away this time. Some of them were easy to let in, some I even encouraged after I realized how much better it felt to be surrounded by friends (even if they weren't Tori) than being alone. I may not have been the greatest company for them when they were really doing their level best to cheer me up, but I was honestly glad to have them on my side.

Some of them, though, I still had to figure out if I wanted to hear from them or not.

Take the Skype call I was waiting for, for example.

It'd been just over a week since Thanksgiving, and we'd just tiptoed into December. Now, like a lot of Southern California, Regan Hills didn't exactly have what you would call seasons. Sure, we had summer and spring, but fall and winter never really got as cold or as wet as it did anywhere else. Sure, the days were getting shorter and there was a bit of chill in the air, but I'd never seen snow in my life, nor did I ever expect it.

Still, it had been a gloomy, overcast day, the kind that demanded a light sweatshirt with a hood in case it rained, and it was cool enough come nighttime that I was glad for the thin blanket wrapped around my shoulders while I sat at my laptop and waited for the call.

Well, waited was one word for it. "Dreaded" might have been another good one, though that wasn't quite right either. What was I feeling, really? This shouldn't have been so hard, it was just a phone call, just talking to someone I cared about, just... well, it wasn't "just" anything, not after the last time we met, not after-

This had to have been the first time Skype ringing actually managed to give me a jump scare. I knew the call was coming, I knew who it'd be, but that didn't make it any less surprising when it actually happened. I watched the name on the screen, looked at their picture, staring at it long and hard considering how wise this move was.

It kept ringing.

I kept looking.

"What the fuck are you waiting for?" I muttered to myself, clicking to answer it.

Within a couple seconds, I was greeted by the welcome sight of Rachel McNeil sitting at a desk in a small apartment. She wasn't as made up as I was used to seeing her, but she still looked beautiful as ever in her pale, red-haired and tattooed glory. The eyes behind her glasses still had a hint of tired sadness to them, but looked a lot happier and healthier than when I last saw her at Thanksgiving, even if her knit cap and comfy-looking sweater meant she was almost certainly colder than I was.

"Hey, Ryan," she said.

"Hey, Rachel. You're, uh, looking good," I replied, trying to think of something neutral to say.

I hadn't seen Rachel in person since Thanksgiving out of a mixture of fear and shame, but we still kept in touch via text even after she left for Portland; by this point we were too good friends to not communicate. This is how I knew as much as I did about how things were in the McNeil household, even the details I'd rather not have known.

"Thanks. Wish I could say the same for you," she said.

"Thanks," I said, sarcastic.

"Hey, I'm just callin' 'em like I see 'em," she said. Her flippant attitude softened for a moment. "The meeting today didn't go well, I take it?"

"That's one way of putting it," I said.

The meeting today was at the office of our school's paper, the Puma Press. Editor Nadia Barclay had called a private meeting with me and Tori in the hopes of trying to get us to work our shit out. Neither Tori nor I were exactly in a place where working out our differences was an option, and while Tori used much more colorful language than I did, we both got the point across to Nadia. This would have been humiliating enough as is had Nadia not then told us that she didn't give a damn about our problems, but if they got in the way of the Puma Press' success this year that she'd kick us both off the paper and make sure we regretted our choice.

In the interests of keeping the peace, I offered to resign from the paper, but Nadia wouldn't let me. Something about how I was too good a writer to let my personal issues get in the way of my success (though I was reasonably sure "my success" in this case also meant "Nadia's success"), and that Tori and I would just have to be adults about this, lest we go back to her making us regret fucking with her.

"Well, you're alive, so, that's something," Rachel said, doing an admirably job of trying to find a silver lining.

"I guess. Anyway, what's Portland like? How's the new job treating you?" I asked, happy to have another topic to change to.

Rachel rolled her eyes, lifting up her laptop and showing me the tiny stretch of her apartment. "I just got through orientation today, but it looks pretty good. The city's fucking cold and wet and full of weirdos, which means I fit in rather well. The apartment's on the Spartan side, and I've got noisy neighbors above me and on both sides, but, it's my own place, and with this job I'll more than be able to afford it. Hopefully I'll even be able to pay off Mom within about three, four months tops."

From what Rachel told me, things didn't quite explode on Thanksgiving after Tori and me had our fight on the front lawn, but they got pretty close. Rachel and Tori spent most of the night arguing, and once everyone else went home, Lauren more or less gave Rachel a stack of cash and encouraged her to get a move on to Portland sooner rather than later. Nobody ever revealed what the fight was all about, but Lauren pushing Rachel to the side wasn't terribly surprising for how she usually favored Tori.

"You two still haven't talked?" I asked.

"Not at length. I keep trying to schedule a Skype chat, but things keep coming up and she says she has to reschedule. I know she's busy, but..." Rachel trailed off.

"Yeah. But..." I replied. Though she never said it in so many words, I knew that Rachel had been looking for Lauren's approval for a while now, any acknowledgment that she'd made a turnaround from the hellraiser she was back when she was a kid, but so far Lauren had kept her at arm's length. Rachel had been trying to make it look like she didn't care, but I wasn't buying the aloof act.

"So, how have you been doing?" she asked. "Still adding pictures to your Senior Year Memories album?"

I smiled, nostalgic. "Not since you. I'm... putting it on a bit of a hiatus right now."

"Oh, don't tell me you're doing that whole bullshit withdrawn act again, because if I have to come down there and kick your ass to pull your head out of it, I will," Rachel threatened jokingly. At least, I was pretty sure she was joking.

"No, no, no, nothing like that," I clarified. "I'm not deleting my pictures or saying I'm never gonna have sex again, but..."

"But what?" she asked.

Good question. My wandering dick had brought me almost as much trouble as it had joy this year, and that trouble was pretty bad. Whether it meant getting punched in the head by Kyle Bowman hard enough to give me a brief bout of PTSD or losing my best friend because I'd fucked her sister and her mom, it was hard to not think that I'd have had a much more peaceful year if I just kept my head down and stopped fucking around so much.

The problem was it wasn't just something I could turn off anymore. For lack of better wording, my sexuality had become a major part of my identity now. If I denied myself that, I'd be denying a major part of who I was and it'd drive me insane. I won't go so far as to say I needed sex to survive, but if I were to pretend that I didn't enjoy it and just try to go back into my shell like I did after Kyle attacked me, I knew I'd have been a mess.

"But..." I continued. "I think I'm going to need to be more cautious. I need to think through what I'm doing, make sure that whatever happens, nobody gets hurt."

"Love and sex are pretty fucked up sometimes. You can't always save everyone from getting hurt," Rachel said.

"Maybe not, but I'd really like to try," I said.

"Awww, aren't you sweet?" Rachel said.

I shot her my middle finger. She returned the gesture with a smile.

It was moments like this that really conflicted me. I dreamed of making things better with Tori, which meant I should have probably been spending as little time with Rachel as possible. I should have just cut off all contact with her and left it at that, but it wasn't that simple. I knew that there was nothing resembling a future between Rachel and me on a romantic level, but she was still my friend, and one I didn't want to lose.

"So, you sharing that sweetness with any of the fair maidens of Regan Hills High while you aren't filling out your album?" Rachel asked.

"Why?" I asked back. It wasn't that I hadn't spent time with anyone lately, but I was curious to see why Rachel was interested.

"I just want to make sure you're being taken care of, is all," Rachel said, rocking back and forth in her chair slightly. I couldn't help but realize at this point that I couldn't see her hands.

"If I were to say no?" I asked.

"I might be coaxed into showing you how little I have on underneath this sweater," she said.

"And if I were to say yes?" I asked.

"Then I still might be coaxed into showing you how little I have on underneath this sweater. So, it definitely doesn't hurt to be honest," she said.

I can't say I wasn't tempted, but she was testing my newfound vow of caution. Having sex with Rachel wasn't what detonated my friendship with Tori, but it was definitely the straw that broke the camel's back, and something I wasn't sure would be a great idea if it were to happen again.

But was there honestly any world where not chatting with Rachel about sex would improve anything between Tori and me? No. If I wanted to have this conversation, I could, and if it led to something, so what?

"I've been taken care of. I doubt I've been the best company for them-"

"You being mopey and all?" Rachel interjected.

I shrugged. "Yeah, but they've been great. It's, uh, still something I'm getting used to. Having friends. It used to be whenever I was going through a hard time, Tori was about the only person I could turn to. Now..."

"It's nice having people you can rely on, isn't it?" Rachel said.

I'd have rather had Tori with me, but lacking her, I really was glad having the people I did in my life. "Yeah. It really is."

"So, lemme guess... Josie's an obvious choice, one so obvious I probably shouldn't need to guess her," Rachel said, finally revealing one of her hands to stroke her chin.

"That's... about right," I said. Of everyone I knew, Josie was the one most actively trying to cheer me up and the one I felt like the biggest failure to for not being able to fully cheer up. Her position on the Puma Press and her pseudo-friendship with Tori could have made this a much more awkward situation than it was, but our budding relationship combined with her experience in bad breakups made her a welcome shoulder to cry on.

"Sarah?" Rachel suggested.

"Nope," I shook my head.

"Really? I drove you to rock her world and she doesn't have the courtesy to help you out in your time of need?" Rachel said.

"Hey, she's a very private person, and I'm not exactly reaching out now, so-"

"Relax, Ryan, I'm just fucking with you."

I rolled my eyes at her.

"So, if the ragdoll's not helping you out, can I assume that Kaitlyn and Brooke are?" Rachel said, arching her hidden arm up, pulling her sweater slowly up toward her chest. From the limited skin I was already able to see from the camera's angle, I could see that she wasn't wearing anything under her sweater for the vista of tattoos she revealed. It made my mouth water with anticipation and a faint hint of anxiety, but an anxiety that was easy to suppress.

"You'd assume correctly. They haven't been around as much as Josie; Kaitlyn's on this self-discovery thing right now, and Brooke's been keeping a busier social life than usual, but they've been there for me. Brooke keeps telling me she's gonna send one of her friends to fuck me senseless one of these days since she feels so bad about skipping out on me so much," I said, laughing, before realizing that that actually sounded like exactly something Brooke would do if I wasn't paying attention.

I really had to hide our hide-a-key better.

Seemingly satisfied by my answer, Rachel pulled her sweater over her chest, revealing her beautiful, bare, C-cup tits. I remembered fondly how they felt, how they tasted. It was enough to make me wish she were here instead of separated by distance for how hard I was.

"That's nice," I said, my voice husky and low.

"Well, I enjoy them," she said, squeezing them and running her thumbs over her nipples with an audible moan. "But I'm glad you like them too. What would you like me to do with them?"

I licked my lips. I'd never had a sexual encounter quite like this, but I was enjoying it.

"Pinch your nipples," I said. Rachel followed my instruction, moaning.

"Harder," I said. With a wolfish smile, she did so, moaning even louder.

"That is nice," she said. "But you want to see lower, don't you? You want to see if I'm wearing any panties?"

I nodded in agreement. Rachel said, "Then pull out your cock. Stroke it for me. Let me see it."

With my cock already rock hard and confined by my pants, freeing it felt great. A small amount of precum had already accumulated at the tip, making it feel particularly good when I started jacking myself.

"Ooh, that's very, very nice," Rachel said, pushing her chair back so I could get a better view of her toned, tattooed abs, and of the lacy black panties she was wearing.

"Fancy," I said.

"I've a grungy aesthetic, true, but I do like a nice, pretty thing every once in a while," Rachel said.

"You know if I were there, this is about the point where I'd be between your thighs trying to remove those with my teeth so I could start eating your pussy, right?" I said, grunting slightly.

"Crude. Very hot, but crude," she said, pulling her panties off and sitting back in her chair, giving me a good view as she played with her pussy.

"It's hard to be eloquent when I'm jacking off and looking at you," I said.

"Fair point," Rachel moaned before reaching off screen, coming back with a large blue vibrator. She turned it on with an audible buzzing sound and brought it to her pussy, her moans taking on a louder, more desperate tone.

"It's got nothing on your tongue or cock, but it'll have to suffice," Rachel moaned, fucking herself silly with the vibrator one-handed while she pinched her nipples with the other.

"Thanks," I grunted, enjoying the show as I jacked myself harder. It'd been a couple days since I'd done this, so I knew it wouldn't be long before I'd be making a mess that I wouldn't look forward to cleaning up.

"My family may have problems, and I'm sorry they spilled over to you, but so long as we can share good sex with good friends, the world can't be that bad a place, can it?" Rachel said.

What we were doing wasn't fixing anything, and I still had a lot of issues that needed fixing, but arguing with her logic was difficult, especially when she looked as luscious as she did.

"Maybe not," I agreed, my free hand gripping the edge of my chair as I felt the orgasm coming on.

***

There are texts you want to receive, and there are texts you don't want to receive. This was one that, at a glance, was one of those ones I wouldn't have wanted to receive.

Josie: Don't be mad

I normally tried not to check my phone too much while I was riding my bike because, well, I had no intention of winding up spread out all over the pavement, but I wasn't averse to stopping and checking an incoming text before I kept moving. This wasn't one of those texts, though, where I could just view it and resume my afterschool ride home, no, this demanded some attention. I stepped off my bike and walked it onto the sidewalk, giving myself the opportunity to talk with Josie while I made progress home.