Senior Year Memories Ch. 25

(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: In the beginning, this was going to be one long chapter, but after a lot of work and realizing that just wouldn't work this chapter will be broken up into three separate parts. This is the second part of three. There's going to be a lot of things going on with a lot of characters, but since this is sort of what I'd call the "season finale" for the first half of Senior Year Memories, I wanted to make this one nice and epic and truly messy. I'd like to again thank MisterWildCard for acting as a second set of eyes on this chapter, for his honest editing and fantastic suggestions, and for the creation of the character Cleo Price. 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: After a long, hard Christmas season, 18-year-old Ryan Collins had the chance to spend some of his winter break relaxing before being invited to a New Year's Eve party by some of his cheerleader friends, which, since this is that kind of story, can only mean an orgy with a dozen sexy cheerleaders. Accompanied by some of his old friends, including Kaitlyn Pruitt, Brooke King, Haley Campbell, Addison Gonzalez, Rose Ferris, Sarah Kent and Jade Alvarez, Ryan got to meet a few new faces. Though sweet and nerdy redhead Sasha Pearl, busty black Amazon Cleo Price, tiny spinner Alyssa Nguyen and trashy blonde Gwen Savage all left impressions, Ryan was most taken by the bitchy cheer captain, Dakota Lewis. Though warned that she was something of a monster, after spending time with her he realized she was a fiercely intelligent girl who cared about her squad. After bonding, the two had plenty of hot, three-hole sex that helped kick the party into gear.

***

Given that I live in a pretty decent area, I had a pretty solid sex education in school growing up. Even so, though, aside from the ins and outs of the old in-and-out, how babies are made and the basics of sexual health and consent, there were a few topics that sex ed never fully covered, however useful they might have been.

Take orgies, for instance.

I love 'em, you probably love 'em, at one point or another in our lives I think we all dream about what one would be like, but when you get to attend your first one, the etiquette is a little hard to figure out. During the New Year's Eve orgy of my senior year of high school, I had a bunch of friends on my side who helped guide me through some of the stickier portions of the first evening, which was nice, but sex was only part of the equation.

Since this was intended as an overnight, sleep would eventually have to happen and wasn't something I'd really planned for. With twelve girls and myself crammed into the guest house behind Dakota Lewis' almost-mansion the bed filled up in a hurry, and with most of the girls having brought blankets or sleeping bags, nearly every horizontal surface and couch was claimed just as quickly.

I hadn't thought this far ahead, and so spent my night underneath a thin blanket in an old rocking chair in the guest house's living room. It wasn't exactly comfortable, but with all the sex I'd had on the night of December 30th, I was too exhausted to really care.

When the morning of December 31st dawned sunny and warm (a benefit to a Southern California winter), my back was killing me from a night in the chair, and I was all too happy to hobble outside so I could stretch. Climbing over and around the girls in their sleeping bags without waking any of them up was challenge enough, but I managed.

Clad in jeans and t-shirt, I snuck back out into the expansive backyard, walking around the pool and shaded hot tub and staking a claim in the covered, semi-gazebo they had. With several comfy couches around a fire pit, it was as good a place as any to hang out and wake up, doing some of the stretches that Brooke had taught me to shake off the night while my phone fired up.

It was a warm morning that threatened to be a pretty hot day. Not my usual definition of New Year's Eve weather, but something I was happy for now.

It was about nine in the morning, maybe nine-thirty... too early for her to be awake, but not too early to check my texts.

Scrolling through the messages I'd received overnight, I found that I'd gotten several, including a few pictures, from my girlfriend, Josie Wong. She'd been away with her family, helping take care of her sick grandmother in Hawaii since right after Christmas. Since her grandmother's prognosis was good, Josie was using it as an opportunity to have some fun while we were away and missing each other.

The first picture she sent had a simple caption.

Josie: I love you. Missing you.

Though wearing her usual dark, long coat as usual, she was standing on a beautiful beach. A dark parasol shaded her pale face, though there was still a good-natured smirk to it.

I scrolled to the next picture.

Josie: Still having fun, though!

She'd pulled her coat open to reveal a dark bikini covering her tight, curvy body, her big, beautiful tits standing out quite nicely.

Josie: Been making some friends, too

A picture of her standing next to four college-aged guys and a girl, all toned and tan and blonde and about everything you'd expect out of a stereotypical group of surfers. Not exactly her crowd, but it was something she was looking for out of this trip.

Josie: Really good friends, maybe.

Pictures of her playfully kissing the girl, then each of the guys.

Josie: So...

Josie: Remember when we talked recently, about what I'd have fun trying over here?

Josie: Remember that you were kinda into it and said I should send pictures if I made it happen?

Josie: Hint: it rhymes with "gangbang"

Josie: Because it was a gangbang

Josie: Now, if you promise you won't get mad... I might have some fun pictures if you scroll down more.

She had talked about hopefully arranging a gangbang with some "surfer dudes" (her words, not mine) if she had some free time while in Hawaii. Admittedly, I hadn't exactly expected she'd be able to pull something like that off on short notice, but I knew better than to underestimate what Josie Wong was capable of.

Even with how much use my cock had gotten the day before, I felt it stir in my pants as I scrolled down.

I had plenty of pictures of Josie naked and taking cock, but these were the first I'd seen of her with a cock that wasn't mine, let alone four of them at once. One picture was her on her knees, surrounded by cocks and smiling with a face covered in cum. Then a series of pictures of her fucking each of the guys in turn, then the girl, then combinations therein, then a long series of her getting double-penetrated by two guys with another in her mouth, the fourth guy's cock in her hand while the girl, naked and blonde and stacked jumping in wherever she was needed.

Society's conditioning told me that I should be jealous of what she'd sent me, but with the unique relationship that Josie and I had forged and the even more unique year I'd been having, I couldn't help but be massively turned on. If none of these girls woke up soon, I might have to just find a good place to jerk off.

At the end of the series of pictures was one final, simple text from Josie.

Josie: So, what do you think?

I could sense the nervousness in that request, and I was all too happy to calm her nerves.

Me: I think it looks like you've been having fun

Me: But if you wanna catch up with me, you need to get some more people together

Me: I spent last night in a pile with twelve naked cheerleaders

Me: And knowing you, I think you can beat that score.

Me: So, get out there and beat me!

Me: P.S. Also, love you, miss you, get back here ASAP so I can fuck you silly!

With the time difference, it'd be a while before she woke up and got a good look at these, but I hoped she would see them and not worry about me. I knew it was unconventional, and if you'd told me a year before that I'd be having all the sex in the world and attached to a girlfriend I was happy to hear was having all the sex in the world herself, I'd have thought you were crazy, but as with many things this year I'd learned to roll with the punches to see where things took me, and things had worked out pretty well so far.

Well enough that I found myself looking at the pictures again and smiling.

"Good news? That's definitely a good news smile if I've ever seen one before," a calm, pleasant voice said.

I looked up from my phone and was met with the arresting sight of 18-year-old Sasha Pearl. Though I hadn't had a lot of time to get to know her yet, having only just become seriously acquainted with each other yesterday, I'd had plenty of sex around her already. It gave us an odd relationship, admittedly, having seen each other naked and having sex without having had sex or really talked ourselves, but I got a good hit off of her right away. She seemed pleasant and kind and had a goofy smile I couldn't help but like.

Not that she wasn't a looker like any of the other girls, either. At 5'9", she was only a shade shorter than me. With short, bright red hair, big blue eyes made even bigger by her surprisingly large glasses and full pink lips, her pale, freckled face was quite cute. Her body, on the other hand, was simply stunning. The oversized t-shirt she wore this morning barely did anything to hide her round, C-cup tits, and the tight sweat shorts she wore showed off her round butt and long legs marvelously.

I didn't really know Sasha Pearl, but I was definitely up for getting to know her.

"Yeah, you could call it good news," I said.

"Wonderful!" she exclaimed, plopping down on one of the couches next to me. "What kind of good news?"

Was this really a good time to tell the truth?

After all that had happened yesterday, why the hell not?

"My girlfriend's on vacation right now and was really hoping she could put together a gangbang, and, well, she pulled it off. Looks like she had a lot of fun," I said.

Sasha clasped her hands to her chest. "Awww, that's so sweet!"

"What is?" I asked.

"Well, that you two have that kind of relationship, right? I mean, my boyfriend and I, we kinda work the same way; we can have all the sex we want with whoever we want, so long as we talk about it and know where our hearts go at the end of the day. I think that kind of trust and communication... well, that's the life, really," Sasha said, sighing pleasantly.

"Yeah. Yeah, it just might be," I agreed. "I didn't know you had a boyfriend."

"Well, I didn't know you had a girlfriend," Sasha replied.

"Probably because we don't really know each other," I commented.

Sasha nodded. "And yet, we've seen each other naked. And having sex with our friends. So, we've seen more of each other than most complete strangers have."

"There is that," I said.

Cocking her head from side to side, her hair swaying as she did, she added, "And we're gonna have sex soon, so that's something, too."

"Are we?" I said, arching an eyebrow.

"You don't want to?" Sasha replied, pulling up the hem of her shirt to show her flat, tight stomach.

"I'm not saying that, I'm just noting that we're talking about how little we know each other, I was expecting a bit of a segue where we got to know each other first before we, you know, started fucking," I said.

"I think we can do both," Sasha said, pulling her shirt over her head and tossing it aside. Her breasts were firm and round, with bright pink, puffy nipples that stood out begging to be sucked.

"Can we?" I asked, readjusting my erection in my pants.

"Definitely," Sasha said, pulling down her shorts and panties. Her pussy lips were nice and full, a landing strip of well maintained, bright red pubic hair pointing down at them deliciously.

She continued, "I mean, there are so many ways to get to know a person you want to get to know, but to see them truly laid bare, doesn't it help to fool around a little? I'm not saying that it works with everyone, but haven't you seen someone hot and done something crazy with them, only to get a better understanding of who they were afterward?"

Her logic was sound. I agreed, "More times than I can count."

"Exactly!" Sasha agreed. "So, I propose some 'getting to know you' sex. You get naked, we fool around some, get to chatting, see where things develop, boom, we're friends, what do you say?"

"I'd say you've put a lot of thought into this," I said.

"After seeing you fuck a whole bunch of asses last night before cumming all over Haley's tits, you're darn tootin' I put some thought into this. If you'll have me, I'd really, really, really like to have sex with you," Sasha said sweetly, rocking back and forth on her feet and looking positively luscious. She was nice, to want to give me a choice, but she definitely wanted to stack the deck in her favor coming onto me the way she did.

And, admittedly, I was happy to have some memories of last night return. Memories of what happened after Dakota and I fucked in her room were hazy, but the images of an anal orgy coming back to me were nice. I mostly remembered a lot of tongues all over Haley's cum-smeared tits, but it was enough to get me harder than I already was.

"Here?" I asked.

"The skin of a ginger aside, I loooove the outdoors, and if it doesn't bother you..." Sasha trailed off.

"...then I better get naked," I finished.

Giggling and smiling that goofy smile of hers, Sasha nodded, "That'd be cool, yeah."

I got up just long enough to get naked, showing her my ten-inch long, thick cock. It wasn't anything that new to her, but the way her smile widened at seeing it this close up was enough to swell my pride.

"Sweet," she said, reaching down to give my cock a quick touch. I returned the favor, sliding a couple fingers along her pussy lips. Sasha hissed pleasurably, looking up at me with her great, big blue eyes. She didn't say anything as I pressed my fingers inside of her, gently exploring and discovering her tender folds. Neither of us said anything when her hand dropped down and began stroking my cock, but it felt damn nice.

"I should've stolen some time with you yesterday, but the others... they have a way of monopolizing everything," Sasha said.

"Well, it's a good thing we're both early risers, then," I groaned.

"I'd say so," she moaned as I rolled my thumb over her clit. She looked up at me, biting her lip and looking oh so luscious. I leaned in, only slightly, but enough that we were able to lock lips and kiss. It wasn't the same kind of passionate, urgent kissing I was used to with so many of the other girls, but the kind of relaxed kiss we could afford from a moment alone like this.

Breaking the kiss, I joked, "This probably won't be the best way to get to chatting, though."

"We can fix that," she said, letting go of me and moving to sit over on one of the couches. She motioned for me to sit next to her, then placed both of her hands in her lap.

Smiling at me awkwardly, Sasha said, "So, you know, to get to know each other, I had a sort of idea. The kind where we could still have fun, but, also talk."

"I'm all ears," I said, curious.

"Well, what I was thinking was, kind of like a game. That each of us could ask the other two questions. Anything at all, and you're free not to answer, but it would help if you did. While the answerer is answering, the other person goes down on them. If someone cums before they finish with their answers, the other one wins. And they have to be real answers, with weight and substance, not just two or three cheap words so you can get through as quick as possible, but honest, full truth," she proposed.

Honest, full truth.

Words that had gotten me in trouble a fair few times, but even more when I ignored them.

"Sounds fun," I said. It was also one I was confident I could win since, not to sound too proud, but I was very confident in my oral skills. Given the way Sasha was licking those full lips of hers, though, I was pretty sure she was every bit as confident as I was.

"I thought it might," she replied.

"What's the winner get?" I asked.

Sasha stroked her chin. "First choice of sex position?"

"I like those stakes," I admitted.

"Me too," she replied, shyly. "So, you wanna go first?"

"At what?" I asked. "Giving or receiving?"

"Hmmm... receiving?" Sasha suggested.

My cock twitched with anticipation. "Sure."

"Good," she said, pushing me back against the couch and leaning over so she could get a better angle on my cock. With practiced pride, she teased the head of my cock, gently licking and kissing it until she was certain she had my attention.

"So, for my two questions, I'm going with one serious, one 'beauty pageant'. Which one do you want first?" she asked.

I thought about this, especially considering the way she rolled her eyes when she said the phrase 'beauty pageant'. There was a certain air of joking to it, but a little bit of bite to the phrase that was difficult to get around. "Why don't we get serious out of the way first?"

"Good strategy," she said, giving my cockhead one nice, long kiss. "So... with gifts like what you've got, how come none of us heard about you before this year? And don't just put it all on Kaitlyn, either, because I know there's more of a story to it than that."

I meant to shoot a defense back at her, but it's hard to be defensive when a sexy redhead's inhaling your cock. Though her smile may have been a bit goofy, her oral skills were anything but, as her soft lips and enthusiastic tongue mixed with more than a fair bit of bobbing made for a pretty fucking amazing blowjob. She meant to win this game, and was doing a pretty good job of it; if I meant to stand a chance, I had to get moving.

"I... I knew what I had, but I didn't know how to use it. I was self-conscious, and horny, and stupid. I didn't know what I was supposed to... oh fuck that's so good... do or say around girls. I thought... I thought what a lot of people like Kyle and all his friends said, that I'd be a dateless, sexless nerd my whole life. I thought that what I had in my pants didn't matter, and that I'd never have the opportunity to become something, someone better than I already was. I didn't... wow, like that, keep going, keep going... I didn't believe in myself then. I'm still learning to, now, but... fuck... I think I'm doing a lot better," I said, barely able to hold myself together with the fantastic blowjob she was giving me.

Taking her mouth off of my cock, Sasha asked, "And do you think you deserve all this now?"

Gulping, I said, "I try to do everything I can to earn it."

Sucking on my cockhead, rolling her tongue over it luxuriously, Sasha said, "I accept that answer."

"And I still haven't cum," I said, a little cocky, trying to cover for how difficult that question was to work over.

"I noticed," Sasha said, kissing it again. "So, beauty pageant question time?"

"Give it to meEEEEEEEE," I yelped, easily losing concentration when she dove in and started swirling her tongue over the head. "Not fair."

"I never said I played fair," she replied, kissing it gently and looking up at me with her big, innocent eyes. "Alright, so, question number two: what do you want to be when you grow up?"