Senior Year Memories Ch. 26

(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 third and final part. 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. After a morning encounter with sweet redhead Sasha Pearl, Ryan took another ride with tight blonde cheerleader Brooke King, where she propositioned him with an offer for some future kinky sex. Returning to the party, Ryan was brought in to judge a sexy competition in the hot tub with Kaitlyn Pruitt, Jade Alvarez, Addison Gonzalez, Haley Campbell and Gwen Savage, only to be stolen away by the gorgeous and statuesque black girl, Cleo Price. With almost a full day of hot sex out of the way, what will the rest of New Year's Eve have in store?

***

Now if you don't already, you might think I'm crazy after I say what I gotta say next:

Despite all the insane, hot sex I was having in the lead-up to New Year's, I find some of my most vivid, fun and even erotic memories of the occasion to be some of the moments in between sex when a bunch of us were just hanging out and recharging, and, yes, even clothed. I may not have been best friends with all of these girls, but with everything shared and the time I'd spent with many, I would definitely call a good number of them close friends. True, we may not have all had much in common, but there were some good, even smart people here that I didn't mind talking with as well as having sex with, and the moments I shared with them are moments I truly cherish.

Close to the top of that list of people had to be Sarah Kent.

A girl who normally wouldn't have been here any more than I would have, she'd come out of her shell incredibly since I'd known her this year. A shy band geek with killer dance skills who'd always dreamed of being a cheerleader, I'd pulled some strings to get her a spot on the squad. It was a difficult, begrudging transition for her, but she'd ultimately fit in quite nicely. Though she was still shy, she was smiling all the time these days.

She'd been especially smiley at this party, which, admittedly was a good look on her. At 5'2", she may have been petite, but her years of dance had made her lithe and muscular, with amazing legs and a tight ass. Her breasts were a modest B-cup (with very sensitive nipples, I knew from experience) and her face was cute as could be. With sparkling green eyes behind horn-rimmed glasses and wavy blonde hair, there was something about her that felt positively angelic.

That she was a freak in the sheets didn't hurt, either, not that you could tell that now. While many of us were lounging about in the guest house, soaking in the air conditioning on what had turned out to be a hot post-lunch afternoon, she looked like a positively normal girl at a sleepover to the casual observer. Her hair was tied back in a ponytail, and she was wearing a loose, blue, spaghetti-strapped top and a pair of pink yoga pants.

While the other girls watched some cheesy reality show about rich girls I didn't really care about, I found myself looking at Sarah from across the room occasionally, hoping that she was every bit as out of the loop on this entertainment as I was.

When I saw her looking back at me, I smiled. She returned the smile, a bit timidly, licking her lips.

We could've easily slipped away with the others distracted as they were, but instead we just stood there for a while, making eyes at each other (and fuck, did she have pretty eyes), laughing along when the others laughed, but focusing very easily back on one another. She turned ever so slightly, showing off her exquisite, if covered, body to me. She ran her hands up and down her tight, modest curves, pinching a nipple through her tank top and biting her lip to stifle a moan.

I couldn't match her sheer beauty and eroticism, but what I could do was readjust the erection in my underwear.

I know, real classy, right?

She smiled at the sight, looking nervously around at the other girls. Then, either convinced that they were all adequately distracted by the TV or just not caring, she quickly lifted her top over her tits, flashing me her succulent mounds and her very, very hard nipples.

I should've probably spent more time recovering, but the way these girls had me going I'd discovered nearly superhuman endurance and cum stores I never knew I had. Seeing Sarah so teasing, so happy, so completely comfortable and in her element when she was usually a shy and near-nervous wreck, it was an unbelievable turn on.

I wanted her. Part of me was even tempted to try to take her in my arms and drag her off to fuck like Cleo had with me not long ago, but I decided to be a little more subtle about it.

With a simple nod, I turned back from the others and walked down the hall toward the guest house's bedroom. Once inside, I worried for a time that I'd played this badly, and that she was still out there with the others watching their inane show.

The door clicked closed behind me. I smiled, turning to face her.

I wanted to say something smart, but when Sarah Kent closed the distance between us and passionately kissed me, smart took a vacation. I tore at her clothes, wanting her naked and getting her there quickly enough. Though I wanted my hands all over her firm, tight little body, she had other plans as she pulled off what little clothing I'd put on for the afternoon. My shirt was tossed aside, and when it came to my underwear she knelt down and pulled it off with such vigor that all ten inches of my thick cock smacked her in the side of the face.

"Sorry," I said.

"For what?" she asked, kissing the head before taking much of the length of my cock down her throat.

Time and again I wondered how the women of this town all got so good at deepthroating huge cocks, and time and again I realized that I didn't really care when they were all so good at it. Seeing Sarah's face, normally so cute and innocent, being defiled as it was was undeniably hot. With tears at the corners of her eager, satisfied eyes and her mouth stretched to the brim as she choked on my cock, she gave me a perfectly wet, and enthusiastic blowjob.

A blowjob was fun, but that wasn't where I wanted this to end (even though I really liked that thing she was doing with her fingers on my balls). So, difficult as it was, I pulled my cock out of her mouth and guided her back onto her feet so we could make out some more. She was definitely the more aggressive of the two of us, wrapping her arms around me tightly as she first flung me into a wall, then rolled so she was sandwiched between the wall and me.

"I wanna... fuck... need to..." Sarah said between kisses. Her voice had taken on a husky, begging tone, one that wasn't helped when I slid two fingers inside of her tight, wet cunt.

"Need to what?" I taunted, trying to match her tone.

"Fuck you don't make this easy..." she groaned, looking up at me with two of the prettiest come-fuck-me eyes that could very well have convinced me to do anything then.

"I need to ask you something... a favor... but not like this... not now... not when you got me all... fired up," Sarah moaned as I fucked her more urgently with my fingers.

"What should we do to fix that?" I asked, still taunting.

Sarah smiled naughtily. "Keep me against the wall, and hold me up."

"Hold you up?" I asked.

"Yeah. Hold me up," she said, lifting her right leg and bracing it against my chest so she was locked in a standing split. That she did this with my fingers still buried in her slit was all that more impressive, but I took her meaning well enough and braced her vertically with my arms and body.

Silently, she reached down and grabbed my cock in both hands, stroking me and spreading my precum so I was nice and slick for her, before lining it up with her pussy lips. Still looking into my eyes, she teased me, rubbing it against her lips.

"Tease," I joked, kissing her.

"You started it," she said, hissing as she pressed the cockhead inside of her. Sarah gritted her teeth for a moment as I slid my cock deep inside of her, my cock reaching deeper and stimulating her in ways it never had before with this odd angle.

She quivered.

She whimpered.

She looked up at me with one of the most intense looks of lust I'd ever seen from a woman.

No words were necessary between us at this point, our eyes silently communicating everything that needed to happen. She wanted it nice, and hard, and deep, and I was going to deliver.

With her hands wrapped around me for stability and mine holding her up on the wall, I fucked Sarah Kent as hard as I could while she held onto her vertical split. I fucked her with a vigor I never knew I had, one that threatened to lift her off the ground a little with every thrust. Though I could only gauge her level of pleasure by the tone of her moans and the way she trembled against me, I knew my cock was in fucking heaven. The splits tightened her pussy in a way I hadn't felt in a long time, gripping me like a vice and threatening to make me cum with every thrust.

It wasn't supposed to end that soon, though, not when we'd been waiting for this moment the last couple days. Bad timing and a lot of other girls demanding my attention had kept us from coupling for most of that time, but now that we were together we were going to make the most of it.

This is why I stopped power-fucking her after a minute or so, wanting to draw this out. Sarah whined with need, but a good kiss and a hard thrust let her know that I wasn't leaving her high and dry.

I kept up with this slower pace, looking down into her eyes, challenging her to cum as I slowly thrust in and out of her. Sarah smiled up at me, biting her lip and knowing full well what I was going for. She chanced a moment to drop her hand down to her clit, her fingers rubbing up against my cock with every withdrawal.

We kept this up for a few minutes more, but it wasn't long before she'd reached her limit. Sarah came against me and came hard, crying out and shaking, her one leg barely holding her up as I continued to thrust away inside of her. It would've been something if I'd managed to cum in her then and there, but even with the superhuman recovery time I'd managed these past couple days, I couldn't pull that here.

Satisfied that she could hold herself up, if only just, I pulled my cock from her and let her leg down. Sarah wobbled on her feet unsteadily, took a few steps, then collapsed to the ground on all fours. Worried, I went to help her up, only for her to look at me over her shoulder with one of the most intense 'come fuck me' looks I'd ever seen.

"Now," she growled.

With an ass and pussy that perfect just staring me in the face, I knew better than to refuse her request. I knelt down behind her, rubbing, squeezing her perfect ass, pulling her cheeks apart so I could get a better look at all of her. Her asshole, so tight and cute and perfect, winked up at me encouragingly, reflected in her beautifully confident smile.

I couldn't help myself. I dove right in, kissing and licking her tightest hole, utterly going to town on her ass with my mouth while I fingerfucked her hot, soaked cunt. This may not have been what she had in mind if her disgruntled mewls were any indication, but that didn't stop me from working both of her holes at once, wanting her nice and ready for the hard fuck I couldn't adequately deliver against the wall.

Once I was certain she was nice and ready, I lined my cock up with her pussy and pushed back inside.

This time wasn't going to take long. My balls were already swollen with need for release from the hard fuck we'd already had, and now that I'd already made her cum, I wasn't feeling the need to draw this out any longer than I had to. I fucked her hard, grabbing her hips for better purchase, grunting and groaning like a wild beast while she just encouraged me with some amazing filth from such an otherwise timid girl.

"God, yes, pound me, fuck me like a little slut, fuck me hard, pound my little slut cunt, harder, harder, fuckfuckfuck, keep going, fill me up, fill me with your cum, keep going, keep going, god I love this cock, harder, fuckmeharderfuckmeharderfuckmeharder, I love this cock, cum for me, cum for me, yes, yes, YES!!" she cried out triumphantly as I just let out with a formless groan. Pleasure flooded my body as I flooded her pussy with my cum, her tight muscles squeezing and milking me for every drop I had.

A fuck that energetic had me collapsing on my back on the floor after an orgasm like that. Though it looked like Sarah would've wanted to keep going, after a wobbly crawl, she seemed to decide on being safe and collapsed on her back next to me.

"Wow," I panted.

"Wow," Sarah agreed.

"So... did you learn that split thing from these girls, or was that...?"

"I knew that one before," Sarah confirmed. "Not a lot of guys can keep the balance and the fucking going like that, too many things to focus on, like rubbing your stomach and patting your head, so, thanks for being better than most. That got it really nice and deep."

"Glad to help," I replied, reaching over and squeezing one of her nipples playfully. She hissed with pleasure, then looked over me with those adorable fucking eyes that could probably get me to do anything if she asked.

Which brought something to mind I'd almost forgotten.

"You said you had a favor to ask?" I asked.

Sarah blushed.

"Bad timing?" I asked.

"No. Yes. I... I don't think there's ever a good time to ask you what I need to ask you. Asking you when I'm well fucked and still dripping with your cum might be one of the worst times, but, I'll need to ask you eventually, so..."

"You want to shower first?" I asked, motioning toward the attached bathroom.

"Tempting, but I'd feel obligated to invite you to join me since we're all so sweaty and sticky and stinking of sex, and if you join me, then I can't say what's going to happen, but will probably involve you fucking my ass," she said.

"That's a bad thing?" I replied.

Sarah smiled cutely. "Never. But, it'd still keep putting off what I wanted to ask. So... I'll ask now."

"Ask away," I said, smiling back at her.

She took a deep breath. "So... after everything you've done this Christmas season, it's gotten me thinking that I want to do something nice for the people I care about, and since there's nobody in this world I care about more than my mom, I want to start with her. That's where... god I can't believe I'm asking this... I need your help."

Thinking I was joking, I looked at her and grinned. "You want me to fuck your mom?"

Sarah looked at me with eyes that said that not only was I right, but that she wasn't joking.

"You want me to fuck your mom," I said more soberly.

"Yes," she confirmed.

"Wow," I said again, staring at the ceiling.

Sarah rolled over onto her side to better look at me. Admittedly, it also pressed her immaculate breasts together, which would have normally stolen my attention. Given the oddness of the request, though, I was able to avoid that temptation.

"I know it's weird, but will you let me explain why I'm asking?" Sarah asked.

"We're friends. Of course," I said.

She smiled at this. "Well... thank you... my mom's about the most awesome person I know, my best friend if I'm being honest, but she doesn't treat herself like she oughta. Since living in Regan Hills isn't cheap, especially for a single mom, she works about four different jobs at any different time to give us the life we got. She's got a part-time office gig, runs her dance studio, sells stuff on Etsy, even sells sex toys to a bunch of other sex-starved moms in town (even though she thinks I don't know about that)."

A couple puzzle pieces fell together quickly, a name I'd heard mentioned once before making being pulled from the depths of my memory.

"Your mom's Viola Kent?" I asked.

"You know her?" Sarah asked, hopeful.

"Of her. From... well, one of those sex-starved moms," I admitted.

Sarah thought about this. "Good. Good that you know. My mom, she works her ass off for us to have a good life, but she doesn't really have one of her own. I think she fools around with some of those other moms, just casual sorts of stuff, but, I know she'd really enjoy having a guy to have some fun with. Nothing serious, but a guy who knows how to press her buttons and is considerate and willing to show her a great time. Since it's dangerous out there for a lady dating these days with all your pickup artists and incels and all those other assorted assholes and the creeps out there, I want her to have fun but safe fun, and you... you make sense."

I'd honestly thought that Brooke asking to peg me was going to be the strangest request to come out of this New Year's party, but this might have taken the cake.

Sensing my hesitation, Sarah added quickly, "And she's beautiful, too. I know I'm not the best to judge, but she's always got guys heads turning when we're out, and she's a dancer, way more flexible and tight than even me. She's always telling me about the trouble she got up to in college because she thinks these stories are good for me and I need to finally get out there and lose my virginity so I can finally start having fun (and I'm too embarrassed to tell her anything else), so you know she's fun, and... yeah. That's my mom, and if you'd put some thought to showing her a good time, I'd really appreciate it."

As with many of the crazier requests I'd gotten in life, this was one I knew I needed to properly take the weight of before acting. In that spirit, I asked, "Can I think about it, or do you need an answer now?"

"Please, think about it. I don't want this to be something you'd rush into agreeing on, especially since I know how strange it is. Please, don't think I'm trying to trap or prank you or anything," she said quickly.

"I wouldn't," I said.

"Thanks," Sarah said. "I'm not used to asking things this serious, but I wouldn't have done it without a ton of thought. I love my mom, and I really like you, but I wouldn't want to fuck things up with you or her. I wouldn't have asked this if I wasn't sure that we'd all be able to keep having our fun and still be friends."

"And it wouldn't weird you out to be sharing a guy with your mom?" I asked.

Sarah shook her head. "No. Well... maybe a little, but if you clean up real good after and, you know, don't like fuck us in the same day or anything, I think that'd work on most of the weird."