Senior Year Memories Ch. 20

(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: Has it already been 20 chapters? So it has! Special thanks this chapter go out to all of you, the fans, for keeping this story going and my own enthusiasm high. I know there have been ups and downs, but the vast majority of you have been wonderful, especially a delightful few I've had the opportunity to chat with who I won't name out of discretion but will thank profusely for being kind and encouraging (you know who you are!). As always, 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: 18-year-old Ryan Collins' quest to do something nice for each of the nineteen women he's had sex with this senior year got off to a quick start as he aimed to help the women of the McNeil family first. Ryan helped his former best friend, Tori McNeil, with the assistance of sexy gamer Izzy Barnes and Tori's girlfriend April Martel, ensuring that Tori was both protected in online games and in her heart. Next, Ryan helped out Tori's mother, Lauren, by breaking up her husband's affair with his protégé, Kelly van Houten, by giving Kelly the fucking she desperately needed. Finally, with Lauren's husband now apologizing and pledging his devotion to her, Ryan was able to coax her into reconciling with her reformed hellraiser daughter, Rachel. With the McNeils checked off his list, who will Ryan help next?

Names Remaining on Ryan's Christmas List: Addison, Brooke, Haley, Hope, Jade, Josie, Kaitlyn, Mallory, Marie, Mrs. Lynn, Mrs. Sullivan, Nadia, Noa, Rose, Sarah, Sophie

***

I hated lying to people, and after a lot of the problems I'd had at the earlier end of this year, I'd vowed not to lie anymore. I had to amend that because not lying at all is an unreasonable expectation and sometimes a little lie is a necessary survival mechanism, but big lies were something I meant to avoid at all costs from this point on.

It was the medium lies that were a little trickier to figure out. More often than not they seemed to fall into that category of lies that was bound to get me in trouble, but there were occasions where they were necessary to make the impossible possible.

Take getting Kaitlyn Pruitt and Sarah Kent into the same room, for instance, two girls who probably couldn't have been more different.

Kaitlyn was a popular cheerleader and an utter bitch, even if she had softened greatly in the past few months since I'd gotten to know her better. Utterly gorgeous with long, silky black hair, soft, lightly tanned skin and a body that less talented writers would say had "curves in all the right places", which in this case translated to a magnificent ass and an impressive set of DD-cup tits. Dressed stylishly in expensive jeans and a dark top that showed a lot of cleavage, she only took her eyes off of Sarah's impressed dance to shoot me the occasional smirk of approval. I'd come to appreciate that smirk, ever since she was the one who took my virginity and spread news of my endowment around school in a way that had allowed for an interesting senior year at Regan Hills High. You could say I knew I owed her a lot.

Sarah was, well, everything that Kaitlyn wasn't. Short and blonde and in the school marching band, she was one of the most painfully shy people I'd ever met, usually peeking out from behind her hoodie with bright green eyes further hidden by her horn-rimmed glasses. She was quiet, but had a way about her where she said something only when she really had something to share and had a natural, radiating intelligence. Cut her layers back and she was a sexy little thing with a tight dancer's body, a pair of firm B-cup tits, and a wild side she knew how to hide well. One of Josie's best friends, she first seduced me on Halloween while wearing a mask and it took a month of tracking her down to properly find her and really get to know her and what she wanted out of life.

That I'd had sex with both of these girls this year would've surprised me enough if you told me back in August, but that Kaitlyn and I would be standing together in the small dance studio behind Sarah's house watching her rock out on a stripper pole dressed only in a pair of spandex shorts and a sports bra, well, that would've sounded completely insane.

Now, though, hardly anything surprised me.

Kaitlyn, though, was still capable of having her jaw drop.

"Wow," she said, watching Sarah's moves.

"What'd I tell you?" I said.

"Oh, you told me, I just didn't believe it," Kaitlyn admitted. Even with both of us watching her, Sarah was lost to the dance, completely in a world of her own. She'd admitted to me, not long after I found her true identity after Halloween, that her dance teacher mother taught her how to pole dance as a way of building her confidence. Though it didn't do much to make her more outgoing at school, it was impossible to ignore that she was an amazing dancer.

"You gotta stop doubting me," I said.

"I should," Kaitlyn admitted.

"You should," I echoed.

After a moment, Kaitlyn added, "You tell anyone I admitted I was wrong, I'll destroy you."

"Well, we can't have that," I replied.

She poked me in the side. I laughed.

Even though she was the first girl that I had sex with this year, I knew that Kaitlyn wasn't the kind of girl I had any hope of a future with from a romantic perspective, and that was fine for both of us. She was great to have as a friend again, and when we could find time to hook up the sex was amazing. She was slowly becoming less of a bitch at school and more discerning when it came to the kinds of guys she got together with, and miraculously enough was even improving on her history tests after I'd started tutoring her.

I may have started this year with a pretty low opinion of her, but Kaitlyn had made one helluva turnaround.

I just hoped the two of us could help Sarah do the same.

"So," Kaitlyn said. "Do you want me to tell her why we're really here, or should I?"

Here's where that medium lie came back into the picture. I knew I never would've gotten Kaitlyn in the same room with Sarah, let alone see her dance, by telling her the truth, because Sarah would've frozen up and told me she couldn't go through with it. I got around this by telling her that Kaitlyn was interested in taking some pole dancing workout lessons and wanted to see what it'd be like. It wasn't completely untrue, because it sure did look like Kaitlyn was interested in what she saw, but it wasn't the main reason we were here either.

"I'll tell her," I said.

"Because I don't have a problem telling her," Kaitlyn said.

"I'll tell her," I repeated. "Thank you, though."

"Anytime," Kaitlyn said, fist bumping me just as Sarah's song wound down.

Sarah looked utterly radiant and satisfied, covered in a light sheen of sweat and panting slightly, a broad smile on her face that only disappeared once we started clapping for her. Then she was back to her usual nervous self, her posture suddenly demure as she walked over to Kaitlyn and me.

"So, uh, yeah, that's some of what you can learn. My mom could show you a lot more since she's the real dancer and all, but that's, uh, a sample of what you could learn. I could teach you if you really want, but you should really learn from her. She's better, but, however you want to go, I can get you a discount since you're a friend of Ryan's and all, and a friend of Ryan's is a.. uh..." Sarah said, her eyes on the floor, only casting the occasional quick glance at us.

Time to tell the truth.

"I'm sorry, Sarah, but I kinda sorta definitely lied about why we were here," I said.

"You... what?" she said, her eyes wide and fearful.

"Kaitlyn's not here to think about taking pole dancing classes," I said.

"I actually am, now, after I saw all that because you're fucking hot, girl, and I can totally pay you, but, sorry, Ryan, continue, we can talk money later," Kaitlyn interrupted.

"I'm confused," Sarah said.

I took a breath. "Last time I was here, you told me that you'd always dreamed of being a cheerleader, but you were afraid of trying out because of the pressure and the rejection? Well, since I knew that you'd probably be too afraid of going to a tryout if I set one up, I kinda brought the tryout to you. And, Kaitlyn? The verdict?"

Kaitlyn smiled. "Now, I'm not in charge of the squad, that all comes down to Dakota Lewis, but I rank pretty high and she and me're tight. We got a couple slots open this year that haven't been filled yet, and one of them is yours if you want it. If you're afraid of any of the girls giving you shit, you won't, but if any of them do (probably Haley), come to me and I'll fuck 'em up for you, easy."

Sarah looked hesitant. I didn't blame her; Kaitlyn smiling like this was usually not a good thing, at least when the old Kaitlyn was involved. That didn't mean she wasn't tempted, no, I could see the battle in Sarah's mind between wanting this so bad but having to deal with her own shyness and any lingering fears she may have had about Kaitlyn as a person.

Kaitlyn saw this too, and went in for the kill. "Please say you'll join the team? We could really use someone who knows how to dance."

Sarah closed her eyes tightly and let out a breath. "Yes."

"Fantastic!" I exclaimed, pulling Sarah into a warm hug. As much as I was happy for her having this opportunity, and I was damn happy for her, I was also glad that I didn't have to come up with another plan for her since this was my one big idea for what to do for her this December.

"Awesome," Kaitlyn said, hugging Sarah herself once I let her go. "Like I said, you'll still need to pass Dakota's approval first, but show her even half of what you showed me here and you're in."

"Will you be there... when I'm trying out?" Sarah asked Kaitlyn nervously, finally opening her eyes.

"Fuck yeah I will. A lot of cheerleaders are real bitches, ain't gonna lie, but you show up and show off and I'll get Brooke and Jade and Addison together and you'll have your own personal cheering section. You're gonna have nothing to be scared of, and you're gonna kick ass, and gimme and some of the other girls a chance to make you over and we'll have you looking like one of the hottest damn cheerleaders in school," Kaitlyn said proudly.

Sarah blushed, casting her eyes downward away from Kaitlyn, then to me. Her voice barely a whisper, she said, "Thank you."

"It's my pleasure. Honestly," I said. "I've... I've been where you are. I've been shy and beat down and not seizing what I wanted because I didn't think I could have it, but if this year's taught me anything it's that if you want something you have to go for it. I'm a lot happier for it, and I think you will be too."

It was hard to tell behind her glasses, especially with her eyes cast down like this, but I think there might have been tears in the corners of Sarah's eyes.

"I'm not... not saying I'm not scared, because I am. I'm so scared, so, so fucking scared. I can't... I don't... this isn't me. This isn't something I ever thought I'd do. I... failure. Failure scares me," Sarah said.

"You're not going to fail," I said.

"Seriously. You're better than half the girls on the squad, at least; you're gonna kick ass," Kaitlyn said.

Sarah laughed, softly. "I wish that took all the fear away. I'm... I know I'm my own worst enemy, but I also know that it helps a lot when you've got people who believe in you, people who... people who want to help. Thank you. Thank you, Ryan, for doing this, it means more to me than I think you'll ever know. Thank you, Kaitlyn... fuck it feels weird to say that."

"You'll get used to it," Kaitlyn said.

"You really do," I joked. "Get to know Kaitlyn; she's more bark than bite, not so say she doesn't bite if you ask her nicely enough, but she's a great friend if you give her half a chance."

"There were some compliments in there, but I still feel like I oughta be insulted," Kaitlyn said.

Sarah laughed, a high, relieved laugh. The nerves and fear weren't gone, but she was sounding more like the sweet girl I really liked. Our eyes met, hers still wet but looking up at me with such pride and satisfaction that I couldn't help but want to take her in another hug.

Sarah had a similar idea, but hers involved suddenly bouncing over to me, wrapping her arms around my neck and pulling me into a quick, powerful kiss. Our lips became one with the passion, our tongues lightly grazing each other just as the all too fleeting kiss ended. It was so easy to get wrapped up in her shyness that it was easy to forget how much energy she was capable of hiding, so much so that I think it even surprised her sometimes. This was one of those times, as once she let me go she looked up at me with big, surprised eyes and a goofy smile.

"Sorry," she said quickly, even though she didn't look it.

"For what?" I asked.

Kaitlyn tapped Sarah on the shoulder. "Hey, you wanna spread some of that sugar around? I mean, Ryan only gave you the networking connections, I'm the one giving you the in to the team. So, really, I think I'm owed a kiss here too, aren't I? Maybe even a better one than he got?"

Sarah asked me, "Is she serious?"

"Sort of. The implied coercion part is just Kaitlyn trying to hold onto her mean girl rep while telling you that she'd really like to make out with you because she thinks you're hot. She won't really hold it against you because she's not that much of a bitch, but for what it's worth it's a pretty big deal if she thinks you're hot because, well, have you seen the girls she hangs with?" I said.

Sarah considered this. "Is he serious?"

"Yeah," Kaitlyn admitted, shrugging.

Sarah looked Kaitlyn up and down, biting her lip as she eyed the more confident, bustier girl.

"Well, it seems only fair..." Sarah said slyly, pulling Kaitlyn in for a kiss.

It was fun watching Kaitlyn's eyes go wild for just a second as Sarah actually went for it, mostly because I'm sure Kaitlyn doubted Sarah had it in her. She caught on quickly, though, kissing Sarah back and showing her why she was one of the top sluts of Regan Hills High. The two of them couldn't have been any more different, which is probably one of the main reasons they were so hot together, but the two of them made out with a passion you'd have thought had been building up for ages. This wasn't just a simple, playful kiss, no, the two of them were making out as if their lives depended on it. They were unhurried, sure, but there was a fire that Sarah used only sparingly that was hot as fuck to watch. Their low moans and groans, the way their hands slowly began caressing and groping one another... I wanted to join in, but I was content to just stand there and watch while my cock grew in my pants.

Kaitlyn came up for air long enough to look at me. "You know that this is gonna end with all of us naked and sticky, so what the fuck are you standing over there for? Get over here?"

"Seriously," Sarah agreed.

"Oh, I like you," Kaitlyn purred.

"And you haven't even seen what I can do with my tongue yet," Sarah challenged.

"Oh I really like you," Kaitlyn retorted, kissing her again.

"I was just being polite," I said, taking off my shirt and sliding in behind Sarah. I rested my clothed cock between her ass cheeks and getting a very contented sigh for my troubles.

With Sarah now sandwiched between Kaitlyn and me, there were so many options for how to continue, each more delicious than the next, but I was content for the moment just standing there, trading kisses with Sarah and Kaitlyn, sometimes both of them at once when we were able to awkwardly contort our necks to accommodate it. I'd learned by now that threesomes can be every bit as awkward as they are hot and fun, but that the hot and the fun had a way of taking precedence over the awkwardness rather nicely.

Seeing two unbelievably hot girls removing their tops more or less at the same time, well, that was one of those sights that had a way of drowning out any awkwardness there might've been. Sarah's modest B-cups and thick pink nipples were a sight to behold, cute, sweet and fun.

Kaitlyn's DD's, though, they deserved their own national monument. They looked beautiful in her black, lacy bra, but once she undid it and set them free in all their glory, I swear Sarah's jaw dropped.

"Those are amazing boobs," she said.

"Thanks. You're not so bad yourself," Kaitlyn praised.

"Thanks," Sarah blushed. "They're not even close to being in the same league as yours, but at least I'll have less lower back pain later in life."

Kaitlyn laughed, pulling Sarah toward her. "Oh shut the fuck up and suck on my future lower back pain."

Sarah was happy to oblige, leaning over and eagerly sucking on Kaitlyn's big, round nipples. Kaitlyn moaned, looking me in the eye hungrily.

"She's good," she admitted.

"You have no idea," I said, torn between looking at the sight of Sarah sucking Kaitlyn's tits, or Sarah's nice round ass jutting out and rubbing against my cock. I reached around, sliding my hand beneath Sarah's spandex shorts and panties and fingering her tight little pussy. I was pleased to feel that she was already hot and wet, but she could've always been hotter and wetter. I fingered her slowly, loving the sounds she made and how it only increased her enthusiasm with pleasuring Kaitlyn.

We went at this for a while, and when I was satisfied with how wet she was I pulled my fingers from her pussy. Sarah mewled in frustration, though she changed her tone quickly when I hooked both thumbs under the edge of her shorts and pulled both them and her panties down around her ankles. When I freed my cock and slid it between her legs, pressing it against her moist lips, that sound of frustration was replaced by one of a much greater, deeper wanting. Sliding my cock inside of her, inch by tight, slippery inch, it felt a lot like home.

Sarah and I may have met under strange circumstances on Halloween, but I was glad that we'd reconnected.

I fucked into her slowly, savoring every moment of taking her from behind.

"Oh my god, oh my god, oh my god," she groaned with each stroke. She no longer sucked on Kaitlyn's tits, instead holding onto her for support. Kaitlyn was glad to help at first, holding her up, playing with Sarah's breasts as she occasionally kissed the blonde girl, but eventually realizing that she was no longer the center of attention, Kaitlyn let Sarah go and dropped to her knees.

"You think that's great, watch this," Kaitlyn said, a mischievous grin on her lips.

While fucking Sarah from behind was a distinct pleasure I wouldn't trade for anything, fucking her while Kaitlyn licked her pussy and my cock as it pistoned in and out of her may have found a way of topping that. The already extreme pleasure was amplified, driving me to fuck Sarah harder. Her mouth hanging open, her eyes wide with first shock, then pleasure, Sarah was a lewd sight to behold.

"Oh my god, oh my god, ohmygod!" she repeated.

I kissed her, sensing she was going over the edge and building to an orgasm already. It was no doubt to be the first of several, and I couldn't have been prouder. I'd done my good deed for Sarah, she loved it, and I got to cap it off with a threesome between her and Kaitlyn. Not a bad day, by my estimation.