Senior Year Memories: Kaitlyn (Patreon Exclusive Story!)
Added 2024-04-23 20:30:19 +0000 UTC(DISCLAIMER: All characters represented in this story are consenting adults at least 18-years-old.)
Hello my wonderful patrons! I hope you enjoy this repost of my third-ever Patreon Exclusive Story!
-aimingtomisbehave33
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It was a handful of days after Valentine’s, and it felt like I’d finally fully recovered. If you’ve read this far, you’ll know that Valentine’s Day had been, for lack of a better word, exhausting. Amazing. Fun. But exhausting. I spent the day after Valentine’s sleeping, relaxing and restoring my strength, and while school was school (and wasn’t shy of sex by any means), I still managed to catch a second wind and feel almost myself by the time I received Kaitlyn’s text.
KAITLYN: Wanna go swimming after school?
The chance to see Kaitlyn both in and out of a bikini was one I would never pass up, so I couldn’t message back yes fast enough. After I made my way home after school, I quickly did my chores and threw on a decent t-shirt, some swim trunks and my shoes, tossed a towel over my shoulder, and began biking over to Kaitlyn’s house.
Now, while I hadn’t spent a lot of time at Kaitlyn’s house this past year, I knew the way over well. When we were little, Kaitlyn and I had been friends courtesy of the fact that she didn’t live very far away, her mother and my father worked at the same job and they were friendly enough. On some days, when Dad had to take care of one issue or another, he would drop me off to play with Kaitlyn. For a while anyway, we were friends. I even looked up to her mom as a surrogate mother figure, which made it all the more unfortunate when Kaitlyn and I dramatically went our separate ways after elementary school.
To say I was happy that we’d reconnected this year was the understatement of all understatements, and with thoughts of what might happen, I biked the short ride over to Kaitlyn’s house, parking on the porch and walking over to the front door.
It was as I reached to press the doorbell that the front door swung open, giving both me and the woman behind it a serious start.
“Oh my god!” the woman yelped, putting a hand to her chest and laughing. “I’m so sorry!”
“It’s okay, Mrs. Pruitt,” I said, laughing. “I didn’t mean to scare you.”
In a lot of ways, Cassandra Pruitt could have easily been mistaken for Kaitlyn’s sister. At 5’4”, with the same brown eyes and silky black hair (and mouthwatering curves), they looked quite similar to one another. However, with hair that stopped at her shoulders, paler skin, wider hips, and a casual style of t-shirts and jeans that stood in stark contrast to Kaitlyn’s more expensive tastes, she was undeniably distinct from her daughter. She tilted her pointed chin up at me, her full lips curling into a surprised smile and her big brown eyes widening behind her glasses in recognition of me. I couldn’t blame her surprise; it had been a long time since we’d seen each other, and I’d undergone a few changes since middle school.
“Ryan Collins! Holy crap, it’s been a while!” she exclaimed, pulling me in for a quick hug. Though uncomfortably aware of the swell of her DD breasts pressing against my chest, I managed not to make a fool of myself as I returned the hug and we parted.
“Hey, Mrs. Pruitt; Kaitlyn just invited me over to hang out,” I said.
Mrs. Pruitt grinned, amused. “Yeah, I’ll bet she wants to ‘hang out’.”
“I’m sorry?” I asked.
She shook her head, waving the subject away. “Oh, I know what my daughter likes to do for fun with the boys, and that you’re a distinct improvement on most… but anyway, it’s so good to see you! Your dad tells me you’re keeping busy, and Kaitlyn’s blaming her improved grades on you. I should really find some time to thank you properly for that, but I’ve got a book club meeting in half an hour that I simply cannot miss. Kaitlyn’s by the pool in back, though, and I see you’ve come prepared. Which is good, since I think this club meeting’s gonna run late.”
Mrs. Pruitt pointed to the paperback under her arm. I grinned with perhaps a little too much mischief at this revelation, but didn’t say anything. Her eyes returned that mischief, only briefly. I knew this was likely because a good number of the ladies at this “book club” and I had spent some quality time together, and that they were prone to gossiping.
Keeping diplomatic, I said, “Well, have a good time. Give my best to Viola.”
“You kids too!” Mrs. Pruitt said, walking past me as she walked toward her car. “Don’t get into too much trouble!”
“I guess it depends on what you mean by trouble,” I said, under my breath as I navigated my way through the Pruitt house.
Even if I hadn’t been here a few times in the past few months, I would know my way around this place like the back of my hand for all the time I’d spent here when I was younger. Navigating through toward the back of the house brought up a lot of memories, and a lot of smiles I hadn’t expected. I also knew that, with Kaitlyn’s mom being out at her book club and her dad being the kind of guy who put in 60+ hour weeks at his office, Kaitlyn and I were likely to have a fair bit of time to ourselves.
Opening the sliding glass door and stepping outside, I first saw the rippling surface of the pool.
And then, in a fashion so dramatic it might as well have been a slow-mo dream sequence from an 80s teen comedy, Kaitlyn emerged. At first, I saw only her beautiful face emerge from the shallow end of the pool, her beautiful black hair slicked back, but that soon changed. Soon she stood up, revealing her massive, DD-cup tits barely restrained by a tight black bikini top. Water dripped down her toned body as she continued to climb out of the pool, running down her tanned, toned abs, over her full, round ass hugged by a tight black bikini bottom, and finally down the long, well-muscled legs of an experienced dancer and cheerleader.
Once upon a time, I would have tried to hide the erection that formed when seeing a sight as unbearably hot as this. Now, though, I just let it tent the front of my swim trunks without a care in the world.
Smirking at me as she stepped out of the pool, Kaitlyn walked over to me, still dripping wet, and said, “It’s about fucking time you showed up; you take the long way over here?”
Ah, Kaitlyn. She’d become a lot less of a bitch over the past few months, but still maintained much of her acerbic charm. I wouldn’t have had her any other way, honestly, especially knowing the deeply caring person that existed deep within her.
“Yeah, well, I had to get ready, and I can only ride my bike so hard, so fast and still keep everything working down here,” I said, pointing at my cock.
Kaitlyn nodded, understanding, gently squeezing my dick through my shorts before quickly kissing me. “Makes sense. But you still kept me fucking waiting. Is Mom gone, yet?”
“Yeah, I caught her on her way out,” I replied, holding back a chuckle.
“What’s with the chuckle?” Kaitlyn asked.
“It’s… ah, it’s nothing,” I said.
“No, it’s something,” she replied.
Sighing, I continued, “Well, it’s just… do you know about the ‘book club’ she’s going to?”
“Of course I do. Mom leaves the house for a few hours at a time, comes back all happy and giggly, and it sure as shit ain’t because of a couple glasses of wine or margaritas or Cosmos or whatever. She’s sneaking off to get laid,” Kaitlyn explained, matter-of-factly.
“Oh,” I said. “And that doesn’t bother you?”
She shrugged. “Dad’s screwing his secretary; mom needs to get some too. You haven’t fucked her yet, have you?”
“Yet?” I asked, taken aback by her words. “And… no, I haven’t.”
“What? I figured it was gonna happen sooner or later, the way this crazy fucking year’s going for you. Just don’t fucking hurt anyone, and you can fuck whoever you want for all I care. Just don’t make it weird or anything, okay? You can do what you wanna do here, just don’t give me any details,” Kaitlyn said, looking up at me with increasing amusement at my clear discomfort.
I hadn’t… well, okay, I hadn’t seriously thought about it, but getting a look at Mrs. Pruitt now, it was hard not to think about what having sex with her might be like a little.
That thought, however, was easily quashed by simply looking down further past Kaitlyn’s face, toward her massive tits, her nearly naked body and… yeah, there was that familiar feeling in my cock again.
“Look,” I said, tossing my towel onto a nearby deck chair. “I didn’t come here to talk about your mom. You invited me over to swim… and I’m gonna swim. Alright?”
There was just enough command to my voice to make Kaitlyn take in a sharp, quick breath, her eyes and grin widening slightly. For added emphasis, I pulled off my shirt and tossed it onto my towel.
“Alright,” Kaitlyn replied, running her fingers lightly down my abs. “Let’s swim.”
Kaitlyn walked over to the deep end and easily jumped in. I took off my shoes and socks, set them by my towel and shirt, and tossed my phone, wallet and glasses with them, then followed Kaitlyn’s lead into the pool. It was a day that was bordering on cool, but the warmer water of the pool embraced me welcomingly.
I had always loved swimming, and while I knew I’d never be an expert, it was fun to feel that almost gravity-defying sensation as I first took to the water, before surfacing. Kaitlyn floated by me, smiling with amusement as I took in a breath. The top swells of her breasts broke through the water, as mouthwatering an image now as it was the first time she seduced me.
“What?” I asked.
“Nothing,” she said, that goofy smile still holding on her face. “I was just gonna ask if you’d done anyone fun for Valentine’s.”
“Ha ha,” I said, without a trace of actual laughter. “I think you know the answer to that.”
“I do, but I like to be nosy,” Kaitlyn said.
I swam around a little, enjoying how shaded her pool was at this time of day. I paddled around her until I could get my feet on the ground, better using the chance to look at her.
“So, how was your Valentine’s?” I asked.
Kaitlyn sighed. “Slow. Boring. I did homework and streamed some sappy romantic movies, spent a little time with my vibrator.”
“That’s all?” I asked.
“That’s all, really,” she answered, rolling her eyes at me. “Even with your judgy eyes, I’m gonna say it wasn’t a bad day.”
“I wasn’t judgy,” I said, defensive.
I really wasn’t judging her, but I was more than a little surprised by her admission. While Kaitlyn had told me that she hadn’t any plans for the day, I would have thought that if anyone could have pulled a date out at the last minute, it would have been her. I knew that she was looking for something more cerebral than just a guy who would lust after her body these days, but I was still impressed that she held to that. Kaitlyn was, quite naturally, insatiable, and I would have expected her to find some sort of outlet when she was that horny.
Once again, I was reminded why it was for the best never to underestimate her.
“You did look a bit judgy, but don’t worry, I won’t hold it against you,” Kaitlyn said, easily swimming over to me, backing me toward the wall. “I know I’ve got a lot of bad years to make up for if you’re gonna fully believe I’m a new woman instead of the bitch goddess you used to know.”
“Just a bitch demi-goddess now?” I suggested.
Kaitlyn splashed me.
I said, “Alright, I deserved that.”
“Fuck yeah, you deserve that,” she said, smirking. “And besides, even if I’m less of a bitch than I used to be, I’m still the baddest bitch in Regan Hills High School.”
“I would never argue that point,” I replied. “Not once, not ever.”
“Ah, you really know how to talk your way into a girl’s heart, don’t you, Ryan?” Kaitlyn said, swimming until she was only a couple feet away from me.
She looked good. Really fucking good. I may have still been recovering somewhat from everything that happened on Valentine’s Day, but Kaitlyn had a way of bringing my strength back to where it ought to be to handle a goddess like her.
“I was more hoping I’d be able to talk you out of that bikini,” I said, smooth as I could.
Kaitlyn looked at me with a bit of a mischievous grin, biting her lip gently. Her big brown eyes looked at me, half with need and half with challenge.
“Make me,” she dared.
“Make you?” I asked, raising an eyebrow.
“Yeah… I think you have it too easy. Everybody knows about you, what you can do… nobody knows that better than me, but I think we can make it even more interesting. Why don’t we make a challenge of it? You pull off my bikini, and I’ll let you do whatever the fuck you want with me,” Kaitlyn said.
I licked my lips. “That’s… one hell of a prize.”
“Nothing you haven’t had before, but if we get the adrenaline going first… yeah, I think it could be fun. Tear off my bikini, and you can fuck me like the slut of your dreams, take me however you want, have your fucking way with every bit of nastiness in that dark, twisted little mind of yours I know you have. But I’m going to be honest with you, I’m gonna fight this. I’m gonna struggle, I’m gonna try to get away from you, I’m gonna slither out of your grasp and find someplace to hide… in short, you’re gonna have to work for this,” she continued, motioning for me to look at her amazing body.
Kaitlyn Pruitt already was the slut of my dreams, but I had to say that her idea for a game was… interesting.
“And what happens if I never manage to tear your bikini off? What do you get if you win?” I asked.
“Hadn’t thought about that… I don’t think I’ll try hard enough to avoid that, but, should I manage to completely avoid you, I’m sure I’ll think of something,” Kaitlyn said.
I thought about this for a moment more before deciding. “Sounds like fun. How do we start?”
“When you take your shorts off and toss them by your clothes… after that, you gotta catch me,” Kaitlyn said.
“You’re on,” I replied, pulling off my shorts and turning to toss them out of the pool.
The second they left my hand, I felt a rush of water as Kaitlyn swiftly swum away. I whirled around, reaching after her and grabbing one of her feet. She yelped and splashed as I pulled her back to me, struggling and twisting out of my grip to plant her feet on the ground and face me.
“Oh, that’s how it’s gonna be?” she shot back at me, coughing on water as her eyes blazed with competition.
“I wasn’t the one who made the rules,” I said, approaching her as she backed away.
“It’s only unfair because you’ve got the height advantage,” Kaitlyn shot back, whirling around and trying to run away from me in the water.
It was true, I did have the height advantage, and you can bet I was fucking using it when it meant a chance to have my way with Kaitlyn. I lunged after her, wrapping an arm around her stomach and pulling her close to me. She thrashed and yowled, reaching back to push off of me impressively as I then wrapped my other arm around her and reached up. I managed to pull her bikini up over her immaculate DD tits, squeezing and groping them, pinching her nipples and making her moan through her yowls.
“Oh… if you think that’s gonna make it easier for you, you’re… fuck… you’re probably right…” Kaitlyn admitted, struggling a little less intently.
“Good,” I grunted, reaching down for her bikini bottoms. I pulled them to her side and felt, quite briefly, her pussy. I couldn’t tell how wet she was, given the circumstances, but the heat was undeniable. Still holding her close, I angled my cock between her legs, trying to line it up with her pussy.
Now, here’s the thing about cheerleaders I’d frequently learned and forgotten at the most inconvenient times this year. They may not be the biggest people in the world, and they certainly might not look the strongest, but those who really put the work into their dance training were almost pure, tight muscle.
Let me tell you now, Kaitlyn Pruitt put some serious fucking work into her dance training.
Though I had my arms around her, she was able to twist roughly, a good 45 degrees in my grip, using this new leverage to push away from me and out of my grip. Then, lightly, she quickly fell to her side and playfully kicked off of me, swimming for the steps. While I was certainly taken off guard, being knocked down and spluttering, I reached out blindly and hooked a finger into one of the straps of her bikini top, pulling at it as she tried to swim away.
Kaitlyn struggled out of the top easily and made her way to the shallow end’s steps, climbing out of the pool and looking down at me with a certain superiority as she readjusted the bikini bottom to cover her shaved pussy again.
“Seriously, Ryan, you’re gonna have to do fucking better than that if you want any of this,” Kaitlyn said, standing over me with the superiority of a queen. A topless, stacked queen wearing only a bikini bottom, but a fucking queen all the same.
“I’m gonna getcha,” I grunted, swimming for the steps.
“You’ll have to catch me, first!” she squealed, running gingerly into the house so as not to slip on the concrete.
Muttering under my breath as I slogged my way toward the steps, I shook my head and said, “That’s what ‘getting you’ implies…”
I made my way first to the chair covered with my clothes and picked up my glasses, quickly toweled off so I wouldn’t drip all over the damn place, then followed Kaitlyn into the house. Having carpet underfoot (and a doormat to dry my feet on somewhat) made me feel steadier, though having to search for Kaitlyn while fighting a bobbing, very hard erection, made for its own unique challenge.
I’d played “hide and seek” with Kaitlyn in this house plenty of times in the past, but it had been a very long time, and certainly never in this fashion.
Nevertheless, her old favorite hiding places came to me quickly.
I made my way toward the living room, soon overwhelmed by nostalgia as the familiar chamber came alive with memory. It had barely changed; the comfy couches facing a large TV, home improvement magazines spaced precisely on the coffee table, the family pictures on the mantle over the fireplace. Holding place of pride in the center was Kaitlyn’s framed senior portrait, her all cute and proper and looking barely the bitch demi-goddess of Regan Hills High. Oh, sure, there was a hint at the wonderful wickedness hiding behind that brilliant, glowing smile, but nothing that would have given away the real Kaitlyn hidden within.
My eyes scanned the room as I took light footsteps around the furniture. I knew she wouldn’t be hiding behind one of the curtains, not this naked, and she probably wouldn’t have hidden in one of the more cramped closets. That left one of her old standbys, a space in the corner of the room left by an oddly placed corner couch. It never quite matched flush against the wall, leaving a fair gap that someone could easily hide in without a lot of effort.
Slowly, trying not to look too purposeful, I said in a sing-song voice, “I know you’re in here… come out, come out wherever you are!”
I was close enough to get a look down at the gap behind the couch, enough that I could see the top of Kaitlyn’s dark hair.
Still trying to look like I had no idea where she was, I walked closer and closer, until she was within arm’s reach. Swiftly, I darted a hand out and grabbed a handful of her hair.
“Gotcha!” I exclaimed.
“Shit!” Kaitlyn yelled in response, jumping out from behind the couch and climbing awkwardly over the furniture. The wetness of her hair kept me from getting an easy grip, and her small, powerful frame allowed her to actually nearly get away from me.
This changed, however, as she reached the end of the couch, tripping over it and landing on the floor. I stopped, briefly, worried that she was hurt, but as she forced herself to her hands and knees, I knew her to be unhurt.
It was this that caused me to charge her, dropping to my knees behind her before she could get to her feet again, then forcibly flipping her onto her back. Kaitlyn looked at me with some surprise, but that surprise soon turned to a quick smile as she playfully struggled to get out of my grasp. I easily found myself between her legs, and with some effort, dropped down over her and pinned both of her hands above her head to the floor. With my other hand, I reached down, untying the sides of her bikini bottom until it was little more than a piece of twisted fabric on the floor beneath her. I looked down at her luscious nakedness, her bare tits and beautifully shaved pussy. My cock, all ten, thick inches, now dripped with excitement and lay against her stomach.
Panting slightly, I said, “I won.”
“Yeah, you did,” Kaitlyn replied, arrogantly. “And what are you gonna do about that?”
I grinned. “Take my prize, of course.”
With that, I leaned down and kissed Kaitlyn, hard. She returned it with a passion I was quite accustomed to from her, moaning softly as her soft lips eagerly melted against mine. Her tongue soon darted out to meet mine, and we may have dueled for a while, but at this point I didn’t care. I’d won what really mattered in this battle. While one arm kept me balanced while I was on top of Kaitlyn, I used my free hand to massage her tits, savoring the sounds she made when I pinched her nipples.
Kaitlyn reached down with her own free hand, grasping my cock and jacking it gently, spreading precum around the tip before angling it downward. I arched my back, helping her line my cock up with her pussy. Already I could feel her heat and wetness as Kaitlyn lined me up. She teased me for a moment, running my cockhead over her lips, against her clit. Moaning and biting her lip mischievously as she teased me, Kaitlyn looked every bit the hottest woman in the world to me just then.
“Are you gonna…?” I asked.
“I could… but you’re the one who won… aren’t you gonna take what you want? You want this pussy, don’t you…?” Kaitlyn teased, her voice high and girlish as she had me exactly where I knew she wanted me.
I growled. “God, you can be such a bitch sometimes…”
“I know, and you fucking love it…” she replied, still teasing my cock against her slit. “You fucking love it when I’m a teasing bitch… you love that I’m the big-titted slut who’s such a fucking bitch, and that you got to be the one to tame me. That all it took was some time with your cock, your fingers, your mouth, and instead of a total fucking cunt, now I’m just a bit of a bitch… you love that you did that. You fucking love everything about me when I’m like this, every fucking square inch of my body, every inch that you know you can have whenever you want… so why don’t you admit you fucking love it when I do this to you?”
The look in her eyes… Kaitlyn knew exactly what she was doing, exactly what she wanted. I had her here on the floor, and she didn’t want this gentle and sweet. She wanted me riled up, she wanted me in an animalistic state, fucking her hard and fast. But it also wasn’t just how she wanted it. I wanted it that way too. Something about being in this familiar, wholesome living room, on top of her with my bare cock rubbing up against her hot, wet cunt… it drove me wild in a way that was more powerful than I had expected.
I didn’t tell her I loved it.
I did, however, force my way forward, grunting as the first few inches of my cock forced their way into her tight, hot pussy.
Kaitlyn’s eyes went wide, her body jolting in response as she let out a low groan.
“Oh… shit!” she exclaimed.
I laughed. “Something wrong?”
“Just a little surprised… and you’re still fucking huge… fuck!” Kaitlyn exclaimed, looking down between us at the way my cock pierced her pussy.
Well, if she was going to look like this, I might as well have given her a show, right? And so, I began rocking my hips back and forth slightly, pushing inch after inch into her with each thrust until I was buried deep inside of her amazing cunt, my balls resting against her ass as she finally took the last inch. Her eyes never left our joining, her mouth dropping open in a distinct “wow” shape, without a word being uttered.
“Fuck… I’m never getting tired of this…” I grunted, looking into Kaitlyn’s eyes proudly before planting a kiss on her lips. Kaitlyn groaned, wrapping her arms around me and holding me close as she massaged my cock with the muscles of her pussy. I started to thrust in and out of her slowly, drawing moans from both of us.
Kaitlyn’s eyes rolled back briefly, but when they fluttered back into place and her lips curled into a grin, I could see she was exactly where she wanted to be. “You’re damn right you’re not getting tired of this… you’ll never get tired of this… never get tired of me… some sluts, they come and go, and while they’re fun, none of ‘em are ever gonna be like me… because out of all of them, I’m the life-changing slut… I can fuck you like nobody else can… and I’m always gonna be there, ready and waiting to show you who’s the fucking best…”
“Always?” I challenged, quickening my pace slightly as I began to fuck her properly.
“Always…” she confirmed. “FUCK! Yes, like that, pound my slutty little cunt… yes… fuck… I’m always gonna be there because I love this cock, and I know you’re always gonna be there because you can’t forget me. You can’t stop thinking about me. My body, my cunt, my mind… fuck… I need you like you need me, and whatever else happens, wherever life takes us, when we’re together, we’re going to be fucking… when we’re apart, we’re gonna think of each other, because when I helped you start all of this, something happened between the two of us, something that can’t be undone… we’re bonded, and we always will be, so we might as well fucking enjoy it by fucking the shit out of each other whenever we can, right?”
Kaitlyn moaned, loudly, and I had no problem pounding into her harder. Her body against mine, the way her pussy massaged my cock with every thrust… yeah, it was its own special kind of perfection. I couldn’t say that Kaitlyn was right about absolutely everything, but she was right that there was a special string that tied the two of us together, and one that couldn’t easily be cut. I may not have had with Kaitlyn what I had with Josie or Brooke or even Rachel, as it turned out, but we had something powerful and distinct. It was its own kind of love, I think, one driven more by lust for each other than by pure feelings, but one that feelings had certainly sprouted from over this year, and one that only got stronger the more we were together. When we were together like this, me buried inside of her, the outside world disappeared and we became one singular point of pleasure, a shining light in the vast emptiness of space.
Okay, maybe we were more a dirty, sweaty, grunting mass of entangled limbs that reeked of lust, but it certainly felt like we were that unique when we were together.
Glad that the carpet didn’t feel that rough, I began to truly give it to Kaitlyn, fucking her harder as my overwhelming, animalistic need took over any sense that might have existed. Looking down at her, watching her face contort with ecstasy as her body responded to my every thrust, from her bouncing tits to the way she tensed with every impact, I was in awe of her. A hungry awe that was not easily fulfilled, but an awe all the same.
It was no shock to me that Kaitlyn came first, as she had always been quite receptive, but the way she came did take me by some surprise. As her orgasm hit her, she soon wrapped her arms around my chest, hard, soon to be joined by her legs locking around my ass. While she cried out in beautiful, earth-shattering bliss, she held me close, almost as if she were afraid that I might drift away if she let up for a moment. Even as I savored how she gushed against me, I was somewhat taken aback by this sudden change in her demeanor… this sudden, urgent tenderness… but not enough to stop having sex with her. I may have slowed my pace, but I was too far gone by this point to stop.
When Kaitlyn’s eyes cleared, she looked up at me, panting and needy, smiling weakly with need. “Come on… do it… do it you fucker… do what you wanted to do… fuck me… fuck me… fill me up… do it… fill your fucking slut up… do it… fuck me, fuck me, fuck me harder, fuck me like the nasty little whore I am, fuck me, fuck your little bitch, do it, fuck, fucking do it, cum for me, cum for me, fill me up… fill your little slut up… fuck… fucking do it, do it, do it, fuck me, fuck me, fucking do it!”
I couldn’t do it… I couldn’t hold back anymore. Still fucking her roughly on the floor, fucking her with the urgency that her legs locked behind my ass encouraged, I did exactly what she demanded.
I came.
I fucking came hard. I grunted loudly, nearly a roar as I buried deep within her clutching cunt and unleashed a powerful torrent of cum inside of her. Pleasure took over any sense I had as I continued time and time again to shoot my cum as deep inside of her as possible, while she only moaned and encouraged me.
The burst of pleasure soon wavered, and I stopped thrusting, looking down blissfully into Kaitlyn’s satisfied eyes. I kissed her, first with a burning passion, but again, slower and softer. This was the pattern that Kaitlyn and I had fallen into, brutal and intense sex, followed by soft, dare I say almost sweet, aftermath. It was a strange dynamic at times for how filthy things got between us when we fucked, but it wasn’t unwelcome.
“Shit… I can feel it in me… that’s a lot of fucking cum,” Kaitlyn said, looking down and laughing slightly.
“You said… you wanted it all…” I said.
Kaitlyn laughed. “Yeah, I guess I did. Still… fuck, that’s gonna be a mess.”
“And you haven’t gotten good at cleaning up cum?” I asked.
She rolled her eyes. “I’m great at cleaning up cum; doesn’t mean I have to like it.”
“Well,” I said, leaning in to kiss her again. “If we’re making a mess, I’m happy we’re making it here, this time. I don’t know if my sheets can handle another dozen washes.”
“Ha ha,” Kaitlyn said with little humor, rolling her eyes at me again. “But I guess that is fair…”
The look on her face softened slightly. “…Ryan?”
“Yeah?” I asked.
“I like it here… just the two of us holding each other… and I’m happy to stay like this for a bit… but after that, you think we can move to my room? The floor’s not exactly soft, and the friction from the carpet’s not the best on my back, and I think we could both use showers to take off the chlorine…”
Neither of us smelled that badly of it, but I understood her meaning. “Yeah, my knees aren’t the best here either. I can move whenever.”
“Not yet,” she said, kissing the side of my neck. “Just… I know I sound like such a fucking girl right now, but you’ll hold me for a little bit longer?”
I grinned at her, kissing her again. “I’m not going anywhere.”
“Thanks,” Kaitlyn replied, smiling sweetly and kissing me quickly.
***
Soon, though, the feel of the floor and the smell of chlorine was enough to get us moving, relocating all our clothes to Kaitlyn’s bedroom. I quickly showered while she cleaned the mess we’d made of the living room carpet, then lounged on her bed while she showered. Still naked, I got caught up on my texts, and even had a few minutes to browse through the Senior Year Memories album. Though there were a lot of amazing pictures, given where I was, it was hard not to linger on those first few shots taken on the day when Kaitlyn took my virginity. Fuck, it had been a crazy few months…
After the water turned off, then Kaitlyn spent a good long while with the hairdryer, I sat up eagerly on the end of her bed. My erection had returned in force, and I was looking forward to her coming back.
With a wall of steam, Kaitlyn’s bathroom door opened. She stepped out with a towel wrapped around her, barely concealing her epic curves.
“If it weren’t completely fucking insane, I swear, I’d fucking marry that shower massager,” Kaitlyn sighed pleasantly.
“Does sound a little insane, but, hey, we’re all a little crazy, aren’t we?” I said, looking down at my phone. “Brooke says hey, by the way.”
“Good to know she still remembers I exist; it feels like forever since we’ve had some bestie time,” Kaitlyn said.
“Sorry, I guess I’ve been monopolizing her lately,” I said.
“Yeah, you have, but I guess that’s understandable. Love and all that,” she continued, amused. Then, with less amusement, Kaitlyn added, “And how’s Josie?”
Josie’s name didn’t sound so good the way Kaitlyn said it, and considering how Josie wasn’t really a fan of Kaitlyn, it sounded like the feelings were close to mutual. “She’s fine. We’re all doing fine.”
“Good. That’s good,” Kaitlyn replied. “I gotta admit, I admire your patience. I’ve tried relationships before. A bunch of times. It’s just never worked out for me. Usually because of the guys, I’ll admit; they only ever want, you know, all this…”
For emphasis, Kaitlyn dropped her towel, revealing her beautiful, naked body to me once again. Grinning, she sauntered over toward me.
Kaitlyn continued, “…and that’s fun, for a while, but it’s just not enough to make anything last. Sex can only take you so far… and I guess I had my bad habits too. I got jealous as fuck, and I guess it led me into making some bad choices… okay, a lot of bad choices. I think I’m better, but, maybe that’s one of those reasons why it’s best that the two of us never got together. You need girls who’re totally cool with you fucking around like you need to, and it seems like Brooke and Josie are perfect for that… and whoever else you guys probably bring into your little sex cult.”
“It’s not a sex cult,” I corrected, harshly for the surprise I felt at her stinging words. I hadn’t faced much in the way of judgment for the arrangement that Josie, Brooke and I had had, and I wasn’t going to start with Kaitlyn here. I knew that we were an unconventional arrangement by most standards, but we were making it work for us as a mutual arrangement.
“Sorry, sorry,” Kaitlyn replied, seeming genuinely surprised and apologetic before kneeling down on the floor between my legs. “I didn’t mean that. Not like that anyway. The poly thing, I think I’m still wrapping my mind around it, I mean, you see a lot of strange shit at this school, but I don’t think I’ve ever really seen this… and when I try to joke sometimes about stuff I don’t know about, I can be a bit of the not-fun kind of bitch sometimes when I really don’t mean to be. This is all further proof that I’d be a shit girlfriend for you, right? So… yeah… I’m sorry. I am sorry, you understand, right?”
It wasn’t 100% easy not to be a little angry with her, but I knew Kaitlyn well enough not to hold it against her in any serious way.
“I do… but try to pick your words better next time?” I suggested.
“Can do,” she said, tapping her forehead in a mock salute. “Seriously… I can. Like I’ve said a million times before, I’m getting better, and I think staying away from relationships has really been good for me recently… but I’ve got a long way to go to figure out who I am and who I’m gonna be best for, I think, before I start opening my heart up properly to people. Thank you, for letting me be stupid and ramble and all that, and not judging me too harshly, and in the long run, helping me be a better person. It’s a process, but I owe it to you. I appreciate it.”
“Don’t mention it,” I said, fully calmed again, enough that I could enjoy the view.
Slowly, she crawled closer to me, her eyes level with my cock. “And thank you for not getting so pissed at me as to deny me… well… that.”
Though I was still a little riled by her poor word choice earlier, I smirked at her. “It’ll take a lot more than that from those bitchy lips to shut this down.”
“Good,” Kaitlyn replied, grinning. “Let me show you how good these lips are at apologizing…”
I knew exactly how good her lips were at apologizing, but that didn’t mean I was going to turn her down when she inhaled my cock to the root in one expert bob. I groaned at the sight of her, looking up at me with her big, playful eyes, while her mouth was stretched to the absolute limit around my cock’s girth. She reminded me of her cocksucking expertise quickly, her head quickly bobbing up and down on my cock in a messy, thoroughly enthusiastic and very sloppy blowjob. Her tongue, her lips, fuck, everything about her was perfect. This naked goddess knelt between my legs and gave my cock the kind of worshipful treatment that tempted me to shout to the heavens in thanks.
Instead of doing this, however, I muttered, “Fucking amazing…”
Kaitlyn pulled her mouth from my cock, but soon replaced it with her hands, actively jerking me off while she smiled up at me.
“Yeah? You fucking like that?” she grunted, eagerly jerking me.
“Yeah,” I moaned in response.
“Good… I don’t always say the right thing, but I know how to fucking apologize…” Kaitlyn said, leaning down to suck my balls while moaning, loudly. Her hands continued jacking me off, and I might have even cum if she kept up at it.
As if sensing that her attention might push me over too soon, she stopped sucking my balls and removed her hands from my cock. Smiling up at me sweetly, she instead leaned in, kissing the head of my cock while swirling her tongue over it like it was a lollipop. It was slow, agonizingly slow, but fuck did it feel good. Her eyes, so deep and sweet and almost innocent-looking, stared up into my soul as she treated my cock like this.
I’d had enough.
Roughly, I grabbed her by the shoulders. “Get up here!”
Kaitlyn squealed as I relocated both of us further up the bed. As I now lay fully back on the bed, I pulled her on top of me. The feel of her tight, supple body against mine was intoxicating, her skin so soft, her breasts so heavy as they pillowed between us. She kissed me eagerly, grinding her very wet pussy against my cock as she eagerly sought another union.
Before this could go too far, though, I had to say something. I broke the kiss with her, holding her by the hips to keep her from sliding onto me.
“I’m happy that you’re doing better this year… I really am. I’m also happy you’re staying true to yourself. You can be less of a bitch and still be Kaitlyn Pruitt, and seeing that side of you come out this year has been fucking cool. If you don’t want to be with someone, that’s your choice… but I am honored to be able to call you my friend this year. I honestly don’t know what I’d have done this year without you as one of my friends. One of my best friends, I think… and, yeah. It doesn’t mean I won’t hope that you still strive to be better, but I am so lucky to be able to call you my friend,” I told her, brushing a lock of hair behind her ear.
If it was actually possible, I think Kaitlyn may have blushed at this. “Not just a friend with benefits?”
“Well…” I said, looking thoughtful. “…that too.”
Playfully, she reached for a nearby pillow and clocked me over the head with it. I retorted, “But friends first! That’s the most important part!”
“Good,” Kaitlyn said, tossing the pillow aside, and… was that relief I caught on her face? Yeah, that was definitely relief.
The wonders never ceased this year.
Kaitlyn kissed me again, stroking the side of my face tenderly with her hand. “So… are we still talking, or are you down to fuck again?”
“Oh, totally DTF,” I joked.
“Awesome,” Kaitlyn replied, arching her back and reaching between her legs to grab my cock. Lining it back up with her entrance, she settled down onto me, groaning as I was buried once again inside her perfect cunt.
“Ah, fuck…” I groaned, pleasurably. “That shit’s nice.”
“Better than nice,” Kaitlyn replied, sitting up on my cock. She sat on me as if I was her throne, looking down at me regally, her tits massive and proud while her pussy looked gloriously obscene stretched out by my cock.
“I’m the best you’re ever gonna have,” Kaitlyn said, rocking her hips as she started to fuck me properly.
Honestly, she was making a pretty good case for her point, I had to give her that.
“I’ll be honest, though, if I ever wanted a boyfriend, and you weren’t tied down, I’d steal you all for myself,” Kaitlyn said, moaning and squeezing her tits as she rode me.
Playfully, I smacked her ass. “So says the woman who fucking loves threesomes, foursomes, orgies…”
She rolled her eyes, but did not stop bouncing on my cock. “Alright, I’d share you… but I’d make sure you knew who your number one slut was… those other sluts, they can fit wherever you want them to… fuckthat’sbig… but I’d be your number one slut, the one who made sure at the end of the day, after you’ve been fucking whatever bitches I say you can fuck, that you know I’m the best… I would fucking make sure you knew that, and if you ever fucking doubted me, I’d fuck you harder than any of those other bitches could, pleasure you ‘til you pass out… fuck, the whole school would be ours…”
“Yeah?” I said, moving my hands up to grope her tits. “You’d like being that kind of power couple, wouldn’t you? Biggest fucking cheer slut in the school and the nerd with the huge fucking dick…?”
“God, yes,” Kaitlyn moaned. “It’d be awesome, wouldn’t it? Nobody would know what to do with us, and if they ever tried to get in our way, we’d fucking destroy them.”
It was an enticing image, I had to give her that. Vaguely evil, but certainly fun in its own fantasy way.
Still lost in squeezing her tits and the way her cunt clutched my cock, I groaned, “Yeah? And what’d we do with all this newfound power?”
Laughing slightly between her moans as she began to ride me harder, Kaitlyn pontificated, “Imagine me cheering with all the girls after we win a big game… but instead of running over to some big meathead while everyone celebrates, I go over and just start making out with you…”
“Some heads would explode with that, I think,” I said, imagining the looks on the faces of the football team.
“Yeeeeeah… fuck… that’d be fun,” Kaitlyn moaned, looking down at me and biting her lip. “Then we’d go to parties and dances, and they’d all wonder why they can’t dance with me anymore, why I’m dancing on you, grinding on you, with my hand down your pants jerking you off on the dance floor while your hand’s up my skirt… fuck, can you imagine us being crowned prom king and queen like that?”
I could. It was a naughty image in my mind, the two of us on stage, Kaitlyn in her sluttiest-looking prom dress, each of us crowned, but instead of us having a first dance, Kaitlyn just dropped to her knees, whipped off my cock and started blowing me.
“You’ve… fuck… got a dirty mind…” I grunted, fucking up into her in time with her driving down onto me.
“I know, and you love it…” Kaitlyn moaned.
“You’re damn right I do,” I growled, grabbing her and rolling over so I was on top of her. Kaitlyn squealed with delight, and I enjoyed the chance to really fucking drive into her. There were few girls who drove me as wild as Kaitlyn Pruitt did, and I wanted to show her what effect she had on me.
“Fuck! Holy shit, fuck me, keep fucking me like that! Yes, yes, yes, I love it! I love it! Gonna make me cum! Make me cum! Make me fucking cum, yes, yes, yes!” Kaitlyn exclaimed as I pounded down into her savagely. She didn’t hold too tightly to me this time, giving me a perfect view of her tits bouncing wildly beneath me as I fucked into her, and of that look of absolute, lustful satisfaction on her face.
“Do it… do it…” she challenged.
I did. I fucked her mercilessly, until she could take it no more and came beneath me. Kaitlyn yelled out a single, loud exclamation before shaking. I felt her pussy juices squirt against my cock as her muscles clamped down upon me, and with one final thrust, I held back no more and came inside of her again.
Panting and out of breath, the two of us kissed softly for a moment, me still buried within her, before I rolled off of her and lay on my back next to her.
“Fuck,” I said, utterly spent.
“Fuck,” Kaitlyn agreed, fanning herself off with one hand.
Reaching over, I playfully squeezed one of her tits, making her moan. Amused, she asked, “Already?”
“Not quite,” I commented, laughing. “But I could do with a little of that cuddling and holding, and then I’ll be good to fuck you like a beast again. Sound good?”
“Fuck yeah,” Kaitlyn said, shifting her position to allow me to wrap an arm around her shoulders, holding her close as we both came down and prepared for our next round.
In this position, I found it easy to touch her, playing gently with her pussy, running my fingertips lightly over her body and making her shiver, squeezing her tits and ass. Sighing contentedly at the attention, Kaitlyn snuggled up against me.
It was a perfect, if perfectly lewd moment in my eye. While Kaitlyn and I may not have been the traditional definition of “friends”, sharing in the satisfaction of what we had done, and the moments we had when we weren’t screwing around… I felt completely and utterly fulfilled. These small moments would probably not be the brightest of my Senior Year Memories, but when they happened, I would cherish them and not let them go until I had to.
Comments
This one hit me in the feels
Lee
2024-07-08 03:52:00 +0000 UTCI enjoy Kaitlyn discovering her feelings and allowing them to be
AlpineFox
2024-06-04 00:00:07 +0000 UTC