Senior Year Memories Ch 24

(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. 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 filthy. 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, who may not see much action yet but shall soon. 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 before Christmas finally came to its conclusion. After giving cheerleader Kaitlyn Pruitt a test that boosted her confidence in her own understanding of their tutoring and handing a stack of interviews to school paper editor Nadia Barclay, Ryan did his best to help bring out the burgeoning artist in uptight religious girl Sophie Cusack on Christmas Eve. Sealing this new arrangement with hot sex, Ryan finished off his good deeds list by arranging for a large number of friends to help volunteer at a Christmas Eve event that Jade Alvarez was helping run. With the list complete (and a box of sex toys gifted to him by all his new friends), Ryan retired for a quiet Christmas Eve at home with girlfriend Josie Wong in the days before she'd have to travel out of town to visit family.

***

In the days after Christmas, I was gifted with something I hadn't known for a very long time: peace.

I'd spent so long focusing so hard on a big plan I often thought I wouldn't be able to pull off, and once I had... I was at peace. I'd done what I'd set out to do, I'd made nineteen women who'd meant something to me these past two months happy, and I was finally free to just go on living my normal life.

Well, as normal as things had gotten since everything changed after September.

With so many of the people I knew on vacations with their families, or busy with other holiday activities, in the days after Christmas I was on my own for a good few days, and don't think I'm crazy but I kind of liked it. I loved all my time with my new friends, and I'll never criticize all of the sex I was getting, but there were occasions where I wanted a little more time to myself, and this allowed me to recharge quite handily.

And that's not to say I was entirely alone, either. Dad was around more than he usually was, and I was Skyping every so often with Rachel McNeil, who was always one of my favorite people to chat with (and have some occasionally very creative cybersex with; man that girl was kinky), and texting as much as humanly possible with my girlfriend, Josie Wong. She'd left the day after Christmas with her family to visit her ailing grandmother in Hawaii, and I felt her absence pretty hard in this period. I loved her, and in spite of enjoying my free time, I wanted to spend my every free moment with her, and since this was the first time we'd been apart for this long, well, I was missing her something fierce.

The most interesting of my long distance connections was also perhaps the most bizarre, in that we were only a short walking distance apart. For a little while now, I'd been exchanging messages with the new girl who'd moved into the house next door to us. I didn't know her name any more than she knew mine, but with our bedroom windows across the way from each other, we'd taken to exchanging notes in the window. Sometimes it was only one a day, other times we actually managed brief exchanges.

I'll admit I was a bit smitten with her, the distance between us adding a little extra thrill to our correspondence. That she was gorgeous didn't hurt either. A pretty black girl with delicate features, big brown eyes and perhaps the sweetest smile I'd ever seen, she was the kind of girl you knew was capable of being a heartbreaker if you let her. With a lean, tightly athletic body, long legs and an impressive afro of loose, dark curls, she had a way about her that left an impression on sight alone.

Aside from her being beautiful, black, and having some truly impressive hair, I'd learned that she was 18, had moved to Regan Hills with her mom after her parents divorced a few months back, and that she seemed to take great amusement in the fact that she'd seen a number of girls come in and out of my house since we'd been neighbors. It was hard to explain via notes in a window what exactly this year had been like for me, but since she seemed to mean her jibes in good humor, I took them in kind.

I couldn't tell you why we hadn't exchanged names yet, or even introduced ourselves since we lived next door to each other, but there was something kind of fun about getting to know someone without actually knowing them. So many of the people who'd been a part of my life this year were women I'd known my entire life, but getting to meet and know new people was still a weirdly intimidating prospect. Exchanging notes like this, it was a stress-free and fun way to get to know someone new.

Even if her sense of humor got a bit pointed, sometimes.

'3 DAYS WITHOUT A NEW GIRL, THAT A RECORD?' she wrote on her small white board, looking at me through the window with some amusement.

At the rate I was going through printer paper, I was going to have to make a trip to Target to get a white board of my own. I scrawled my response, 'NO, THE 18 YEARS BEFORE THIS ONE GOT THAT BEAT'.

She laughed, writing a new note. 'POOR THING.'

I wrote, 'NOT POOR ANYMORE. HAVE A LOT OF FUN & A GIRLFRIEND. IT'S A GOOD YEAR.'

She nodded. 'AT LEAST ONE OF US IS HAVING A GOOD YEAR.'

I responded, 'NEW YEARS RIGHT AROUND THE CORNER. TIME TO MAKE YOUR OWN GOOD YEAR.'

'YOU'RE OPTIMISTIC,' she wrote.

I replied, 'IT'S A NEW THING FOR ME, BUT I'M ENJOYING IT.'

'SEND ME SOME OF THAT OPTIMISM ANY TIME,' she wrote.

'GIVE IT TIME. ONCE SCHOOL STARTS BACK UP, I THINK YOU'LL LIKE REGAN HILLS,' I wrote, then pulling a new piece of paper to put beside it. 'IF A GUY LIKE ME CAN HAVE THIS YEAR, PRETTY AS YOU ARE, YOU'LL CLEAN UP, EASY.'

She smiled a smile I'd come to like, even from a distance. I was hoping to get the chance to see it up close sometime in the near future to confirm that. She wrote, 'WE'LL SEE.'

Looking to add a joke of my own, I replied, 'STOP STALKING ME, AND I MIGHT INTRODUCE YOU AROUND TO SOME PEOPLE.'

She laughed again. 'NO PROMISES. TRYING TO FIGURE OUT HOW YOU GET SO MANY GIRLS IS MORE FUN THAN ANYTHING STREAMING.'

'I CAN SUGGEST SOME GOOD SHOWS,' I replied.

'OR YOU CAN CLOSE YOUR CURTAINS AND KEEP ME IN SUSPENSE,' she retorted. I'd never left my window open while I was spending time with a girl, but that I'd made my neighbor so curious was exciting in its own way.

I responded, 'AND END OUR CONVERSATIONS? NAH, YOU'RE TOO FUN.'

She smiled again, a very sweet, friendly, almost fond look. She eyed me for a while before writing, 'YOU'RE NOT BAD YOURSELF.'

My phone started vibrating in my pocket. When I saw the name on the incoming text, I muttered, "Speak of the devil."

Kaitlyn: Back in town. Need to talk and ride your dick. You free today?

I thought about it, then responded.

Me: Free now, come on by whenever.

Kaitlyn: Sweet. See you soon.

Pocketing my phone, I wrote another note for the window. 'HAVE TO CUT THINGS SHORT. FRIEND COMING OVER.'

'FRIEND or "FRIEND"?'

'BOTH,' I replied. 'GONNA CLOSE CURTAINS SOON.'

'AH, RUIN ALL MY FUN,' she teased.

If she was in the teasing mood, I was more than happy to tease back, 'YOU COULD ALWAYS COME ON OVER IF YOU WANT.'

Again, she cocked her head from side to side, stroking her chin in mock thoughtfulness. 'TEMPTING. BUT MAYBE WE SHOULD KNOW NAMES FIRST.'

Joking back, I said, 'THAT'S A BIG STEP.'

'RIGHT?' she responded, looking almost a little sad that our conversation was about to end. 'WELL, HAVE FUN.'

'I WILL,' I replied, smiling wryly.

***

When it came to having fun, Kaitlyn Pruitt always had a way of delivering. Seeing the goddess standing in our front doorway, even bundled up as she was in her less tight than usual pants and warm coat with its fur-lined hood, clearly cold but still with that mischievous smile on her beautiful face, I was hard almost instantly. Though the outfit didn't flatter her as much as what she usually chose to wear, I knew what was underneath. I knew how perfectly pert her DD tits were, how they felt in my hands, mouth, wrapped around my cock...

I knew she had a tight yet curvy body from her years of cheerleading, with an amazing ass that'd be easy to become obsessed with. I also knew that behind her usually pretty resting bitch face was a girl I considered a friend, who'd helped me come into my own this year and I would be forever grateful to.

"Hey, Ryan. Your dad home?" she asked, arching her neck to look inside.

"No; his dojo's competing with their bitter rivals today, so he's gonna be out for a while," I answered.

Kaitlyn's smile broadened. Forcefully, she stepped inside and closed the door behind her. Pulling down her hood and allowing her silky black hair to fall about her face, she said, "Good, because I'm fucking horny and need some serious cock, and I don't know if I can make it to your bedroom."

I was trying to come up with an appropriately witty response, but when a girl as hot and so perfectly slutty as Kaitlyn Pruitt throws her arms around you and practically shoves her tongue down your throat, witty responses have a way of dying quick deaths.

We made out savagely, as if it had been years rather than days since we'd seen each other last, first with her pressing me against the wall, then me her. My hands found first her tits, then her ass, groping her through her clothes as she skillfully pulled all ten inches of my thick cock from my sweatpants and started jacking me.

"Oh, you've missed me too, huh?" she cooed.

"Missed, no. Wanted, maybe," I said cheekily, kissing her passionately and squeezing her ass playfully.

"Well, you're spoiled for choices, me, I just had to spend four days surrounded by family and only family and so much family I couldn't even fucking masturbate. I haven't cum in almost a fucking week," Kaitlyn complained, her usual bitchiness coming across in a way it hadn't in quite a while between us.

"We can fix that," I said, dropping one hand between her legs and rubbing her pussy through her pants.

"You better," she said, kissing me desperately, letting go of my cock so she could undo her pants and pull both them and her panties to the floor. From a brief glance, her pussy was as bare and beautiful as ever, but the whiff I got off of her rich cunt told me she might well have been even hornier than she said.

"We need to talk," she said, kissing me quickly. "There's a lot we need to talk about, but I need to be fucked, please, please fuck me, right now, please fuck me hard, make me cum... please?"

Grabbing her by the hips, I turned Kaitlyn around and bent her over slightly. She braced her hands up against the wall, spreading her legs as much as the pants around her ankles would allow her while I lined my cock up with her steaming entrance.

Sliding into Kaitlyn's pussy, still so lusciously tight, hot and wet, even after all we'd done together, it was like going home. I loved it for how good it felt physically, but even more for how it connected the two of us. Kaitlyn would be the first to admit she wasn't exactly girlfriend material, but the two of us had a unique friendship that defied pretty much any definitions that I knew and was accompanied by some of the hottest sex I'd ever had.

It may have been unconventional, but damn it if it didn't feel fucking amazing.

What we did now, though, with her braced against the wall right next to my house's front door, had very little affection to it. Oh, sure, we kissed and smiled at each other when we could, but both of us were in such a need of release, for human contact, that we weren't much for talking. I pounded into her with long, hard strokes, reaching around to grope her tits with one hand while fingering her clit with my other to help her find that pleasure she so clearly needed. Both of us were only naked from the waist down, pants and underwear around our ankles as we hastily fucked, wanting, needing that frantic release so we could better talk with each other.

It had been so long for Kaitlyn, though, that her first climax came quickly. Crying out with a sharp burst of ecstasy, she bucked against me. Her legs went weak, almost buckling underneath her. I did my best to hold her up in our awkward position, and it was only through experience and a minor miracle that both of us stayed standing, panting and holding close to each other as she rode out the rest of her orgasm.

I was about to ask if she was okay if I quickly finished myself off, when she helped make that decision for me. At first kissing me long and deep, her eyes full of lust and hunger, Kaitlyn then pulled me out of her pussy. Though I was aching for her moist slit, when she instead turned around and dropped to her knees, taking the entire length of my cock into her throat with practiced ease, I was hardly going to complain.

As with our fuck, it was a frantic, almost desperate blowjob, the kind that made her eyes water, makeup run, and strands of drool drop down from her mouth onto her coat and the tight sweater clad tits beneath. Kaitlyn looked up at me with the prettiest eyes, blowing me so expertly that I might've cried if I didn't so desperately want to cum.

Thankfully, in her expert hands (and lips), I didn't have to wait long. Though I warned her when I felt it coming on, that didn't stop a cocksucker as expert as Kaitlyn. If anything, it only motivated to go harder, sucking and bobbing with a greater intensity, her tongue swirling around the cockhead on every backstroke, playing with the bottom of my shaft as she sucked even more. She was an expert at taking me to the edge, pushing me toward it and leaving me teetering.

I was about ready to burst when she took her mouth off of me entirely, looking up at me oh so sweetly and sticking out her tongue to oh so slightly graze the underside of my cockhead.

That did it. That set off a stronger orgasm than I expected. Kaitlyn, the skilled slut that she was, kept her mouth wide open and managed to catch quite a bit of it, but that didn't stop the stray spurts that painted her cheeks, chin, even a few stray shots landing on her neck and sweater-clad breasts. Now it was my turn to be the one who had a hard time standing, but the sight of her coated with my cum, holding her mouth open so proudly to show off the lake of cum inside, it was enough to keep me going.

Once I'd finished, once she'd coaxed the last drop out of me with the tip of her tongue, Kaitlyn reached into the pocket of my sweatpants, pulled out my phone and gave it to me. I took her meaning easily, taking a picture and adding it to my Senior Year Memories album. She'd started it after all, I didn't blame her for wanting to appear in it as much as possible.

With a good shot of her added to the album, she finally swallowed, then looked down at herself.

"I think I'm gonna need to borrow your washing machine," she said, not at all angry.

"Yeah. That might have to happen," I said, still panting.

"Then we really gotta talk. You got the time?" Kaitlyn asked.

"For you?" I replied. "I got all the time in the world.

***

I started the load of laundry with Kaitlyn's sweater, coat and shirt to be safe, tossing in some of my own clothes for good measure. I'd gotten used to a lot of laundry and cleaning since this year began, more than I was used to, but if that was a sacrifice I'd have to make to enjoy the year I was having, then it was one I was willing to make.

Returning to my room, I was greeted by the luscious sight of Kaitlyn sprawled out on her stomach on my bed. She'd stripped down to one of my old t-shirts and one of her many thongs (today it was navy blue), her long black hair tied back with a hair band. She was facing away from me, giving me and looking at her phone, presenting an utterly perfect view of her glorious ass.

I'd seen it, hell, I'd fucked it more times than I could count, but that didn't make me drool any less at the sight.

I closed the door behind me. Kaitlyn didn't turn at the sound.

"Thanks for the orgasm, by the way," Kaitlyn said, still swiping through her phone.

"You too," I responded, walking up behind her. I ran my hands up her toned legs, savoring the feel as I cupped her ass.

"You know, I did actually come to talk today, not just to fuck you," Kaitlyn said.

I stopped stroking her. "Oh?"

"I didn't say stop," Kaitlyn said, turning back and looking at me until I continued, then going back to her phone. "I... I wanted to see how you were doing, after all your holiday stuff, and Josie leaving, and all that."

"Josie didn't leave," I clarified, pulling her thong off and tossing it aside. "She's just on vacation with her family. And hoping to get a gangbang off the ground while she's surrounded by surfer boys."

"Really? Awesome. That girl always knows how to surprise," Kaitlyn admitted, nodding appreciatively. I knew that Kaitlyn and Josie were about as opposite as it got and would never really be friends, but between the two of them, I knew that game understood game.

"Seriously. And I've been doing good. Keeping things nice and quiet with the holidays. You?" I asked, parting her legs as I continued to stroke her thighs and ass.

"Christmas at home with family, the next three days in a second-rate hotel watching all my family remember that none of them likes skiing very much, like they do every year. Having to deal with all the older family asking what my college plans are and not wanting to tell any of them that I haven't got a fucking clue. Fun," Kaitlyn said.

"Fun," I agreed, letting my fingers drop to Kaitlyn's pussy and enjoying the sound it pulled from her lips. "Just tell them you're going to Regan Hills Community College."

Kaitlyn laughed. "Yeah, that'd give 'em a heart attack. What do you tell people when they ask?"

I shrugged. "Probably that I'm going to Regan Hills Community College. I haven't got a plan on what I wanna do with my life, and it sounds like an easy and cheap way to get some credits out of the way."

Kaitlyn's eyes widened. "I didn't mean anything-"

"Nah, don't worry about it," I said, brushing it off by brushing her pussy with my fingers. "I've never been fancy, and a good friend who's done the college thing told me it'd be a good way to help me get my head sorted. I can't call that a bad plan, can I?"

Kaitlyn groaned. "Since you're twisting a couple fingers inside of me, I can't really argue with that, can I?"

Sheepishly, I pulled my fingers from her. "Sorry, wasn't paying attention."

Looking over her shoulder, Kaitlyn smiled devilishly, "I should get you to not pay attention more often."