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Senior Year Memories: Kaitlyn Vol. 2 (Patreon Exclusive Story)
🕑 Added 2023-10-29 01:17:20 +0000 UTCHello my wonderful patrons! It's time for another Patreon Exclusive Story, all thanks to you, your votes and fantastic support! When I originally put it to a vote that a SYM Girl who'd already gotten her own Patreon Exclusive Story would get a chance at a return, I really should have expected Kaitlyn Pruitt to make her way to the top of that list. As one of your favorite characters, and mine, I am always excited to bring her back to see what she and Ryan can get up to. And while you did generally vote against making this chapter a threesome, I couldn't resist a bit of a cameo toward the end which didn't technically make this a threesome while still adding some spice, so, I had a little fun here. I hope that overall you'll enjoy the results all the same.
And, as always, it goes without saying, please do not distribute this story in any fashion outside of Patreon, since, well, it would defeat the purpose of making it exclusive here, and it would make me sad. And of course, special thanks to my editor, Lil_kitty, for her diligent efforts making sure my stories make sense.
-aimingtomisbehave33
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I’d managed to make it to senior year at Regan Hills High School without ever having to attend a single school sporting event, but by the strange combination of working at the school newspaper, and the company I was keeping these days, I was forced to break that record this year on multiple occasions. When it was at the behest of Puma Press editor Nadia Barclay, saying that I needed to at least have an understanding of school sports in the event that I would ever need to act as a replacement for one of her dedicated sports reporters, I would go begrudgingly and make very little effort at learning anything new or useful in the hopes that I’d never be asked again. Call it weaponized incompetence if you will (since that’s exactly what it was), but if I could avoid going to sporting events any more than I had to, I would.
When I was encouraged to go to games by some of my newer friends this year… well, what can I say, I was a man who had a hard time saying no to a beautiful woman. Especially one who accompanied that request I attend a game with a picture of her pussy.
I was only human, after all.
That was how I found myself out one January evening, sitting in the front row of another football trouncing of the Regan Hills Pumas by their dreaded rival, Blair Valley High School. Regan Hills had always been notoriously bad when it came to football, but with their former “star” player (and all-around jackass) Kyle Bowman expelled a few months back because of yours truly, things had actually started to look up for the team. They were still terrible, to be sure, but without Kyle trying to steal all the glory, it allowed other players (especially my recent friend, Peter Nixon) to shine and get some points in.
To translate: we were still losing, but we were losing by fewer points than ever. For Regan Hills High, that was practically something to throw a parade for.
As much as I joined everyone else in cheering Peter on, however, it wasn’t he who invited me to this game, no… I was here for the cheerleaders, and sitting in the front row, I had an amazing view of all of those beauties.
Dakota Lewis. Brooke King. Haley Campbell. Riley Richardson. Jade Alvarez. Alyssa Nguyen. Sasha Pearl. Kitty Stein. Addison Gonzalez. Sarah Kent. Cleo Price. Gwen Savage.
They were a rogue’s gallery of some of the hottest girls in school, the vast majority of whom I’d not only count among my friends, but I’d also had sex with. Seeing all these girls with their tight bodies and almost as tight blue and white uniforms, their short, flowy skirts teasing at their toned legs and everything hidden beneath, it was enough to make me shiver in my seat and my cock grow about as hard as I’d ever remembered it. Every so often one of them would lock eyes with me, tipping me a wink or licking their lips, with Brooke even blowing me a playful kiss.
I’d have given pretty much anything to be buried beneath a pile of all of them again just as I’d been at New Year’s… but as I searched that line of girls, I had to admit my surprise at a familiar face who was missing, which was all the more curious considering she was the one who had invited me here. I looked up and down the line, and peered down to the benches beneath the stands, but couldn’t find her, and wondered if tonight’s pussy pic invitation had been an error.
I didn’t have to wonder for long, however, as I soon received the text asking if I was here. After confirming that I was, I quickly received another insisting that I go down to the girl’s locker room, a location that brought a small little smirk to my lips for the memories the location brought back.
Getting out of the stands was a challenge enough, considering they were weirdly packed for how badly we were losing (and there were plenty of people happy to call me a dumbass and tell me to sit down because I was blocking their view), but considering what awaited me, I’d have walked through the fires of Hell itself to get where I needed to go.
Once I got off the stands, I could really pick up my pace, making my way down toward the less populated gym area near the edge of the football field. Looking around to make sure I wasn’t being watched, I made my way over to a familiar bench next to an old, semi-working Coke machine, before looking up to the partially cracked-open metal mesh cover to the window above me. I’d had it on good authority that it had been busted open some time ago by students who wanted to use the gym for some off-hours training, and despite the school’s best efforts to discourage use, they’d never had a chance to fix it.
Bad for them, good for anyone who was looking for a little privacy and fun.
Checking one last time to make sure I wasn’t being watched, I climbed up through the window and dropped down into the gym, making my way quickly over to the locker rooms before darting into the girls’ one.
Now, admittedly, there was a part of me that felt nervous about this, and not just because of the B&E of it all. For all the debauched madness I’d engaged in this year thus far, often taking place in locales where I wasn’t meant to be, it still felt strangely taboo to be sneaking into the girl’s locker room, even if I’d already been in there a number of times for a variety of messy sexual encounters. Even with my familiarity with it, it was a place I knew I shouldn’t be, and one that added a delicious sting of the forbidden to the naughtiness that drove me.
Looking around the darkened locker room, it seemed as if it were completely empty, and I couldn’t help but call out, “Hello?”
My voice echoed in the room for a second before I got the response, “It took you long enough. I’m in the back near the offices… I gotta make this quick.”
I walked toward the opposite end of the locker room, past the equipment closets and showers toward the offices set aside for coaches and athletic administrators. Only one of them was lit up, its door partially ajar, which I took for as good an invitation as any, pushing the door open and stepping inside. It was a small office lined with pictures of various Regan Hills High School cheer teams from over the years, as well as a few odd awards and trophies. Not many, but certainly more than our football team would ever get.
None of this really interested me as much as the girl standing by the couch. The 5’3” stunner looked me over with hungry, deep brown eyes, a pleasantly confident arrogance overtaking her gorgeous face. Her full, pouty lips were curled in a smug smile, slightly parted so she could lightly remoisten them with her tongue. Her soft, slightly-tanned skin and long, silky black hair (conveniently tied back in a braid today, no doubt for practicality during cheering) added as ever to her model good looks, though nothing compared to her insane body, especially in her cheerleading uniform.
On its own, the Regan Hills High School cheerleading uniform was neither that revealing nor that conservative. Its white, long-sleeved top with blue, striped accents and “RH” printed on the chest looked fairly ordinary as cheerleading outfits went, revealing only a slight bit of midriff, while the bolder blue skirt was technically short enough to go above the knee, but only just. Combined with knee high socks, it wasn’t an outfit meant to show a lot of skin, but it was playful and flirty on its own.
On a body like Kaitlyn Pruitt’s, though, it was practically a pornographic fantasy come to life. I don’t know what size she ordered when she got her uniform, but it was definitely a little on the small side for her, and I could swear she’d had it modified on top of that. The top was tight enough that it made her already impressive DD-cup breasts look massive, with the neckline cut just enough to show off a little extra cleavage on top of that. Several more inches of midriff than necessary were now visible, exposing her impressively tight abs, while her skirt was also definitely a couple inches shorter than it was supposed to be, barely resting beneath her round, beautiful ass. It was hardly the kind of look that you’d expect to see at a formal competition, but given how delightfully oversexed the cheerleaders at Regan Hills High were, it wasn’t an uncommon one to see at home games as far as I understood. I wouldn’t begrudge them having their fun here, as I was certainly enjoying the view.
While my eyes roamed her body, I could feel hers staring into me, also clearly enjoying what she was seeing. As I was still new to being ogled myself, it still was a slightly strange, if rather welcome, feeling.
Finally shaken from her staring, Kaitlyn shook her head slightly and looked me in the eye. “Look, I’m horny as fuck tonight, but I’m still expected out there on the field to shake my ass and pom poms with the others, so we can’t take too much time. But, I’m also kind of losing it wanting to go out there with one of my holes full of cum, so, you wanna fuck?”
For emphasis, she teasingly pulled up her skirt, revealing to me that she wasn’t wearing panties. True to her word, her shaved pussy looked quite wet, which might have explained the faint smell of sex I’d thought I’d smelled on entering the room. Her moist sex looked as perfect and tasty as ever, causing my already impressive erection to twitch in my pants.
I smirked. One of those things I always appreciated about Kaitlyn was how direct and to the point she could be. Sure, it removed the romance from a number of situations, but it was also one that I was more than happy to enjoy when moments like these came up.
“Hell yeah, I do,” I said, closing the office door behind us before I approached Kaitlyn, wrapping my arms around her and pulling her in tight so we could make out.
“Mmm, thank you,” Kaitlyn purred, kissing me back eagerly. Her soft lips conformed as perfectly to mine as they ever had, her swift tongue darting into my mouth to brush up against my own as we kissed.
While we kissed, her hands were busy, first tugging my shirt out of my pants before she got to working at my belt. She fumbled a little awkwardly in her haste, but with as much experience as she had at getting a guy naked in a hurry, that only lost her a matter of seconds. Soon she had my belt undone and my pants unzipped, dropping them around my ankles.
Kaitlyn pressed her hand against my cock, rubbing it through my underwear. “Well, you’re excited at least.”
Groaning, I replied, “Can you blame me, the way you’re looking tonight? And…”
I reached down and thrust my hand between her legs, hooking two fingers inside her soaking wet pussy, curling them around and massaging inside of her dripping cunt. Kaitlyn moaned, loudly as I did this, holding onto me with her free hand while wantonly massaging my cock with the other. We did this for a moment, moaning and groaning and continuing to make out, holding each other close as we used our hands to drive each other wild, but as she’d said, she was in a hurry.
I was happy to help expedite some of this for Kaitlyn, while still having some of my own fun teasing things out.
Growling, I grabbed her and pushed her down, forcing her to sit down on the couch before I dropped to my knees in front of her. I leaned in briefly, kissing her exposed thighs, before I pushed her legs apart so quickly that she gasped.
“I said… I was in a hurry…” she moaned, knowing what was coming and making absolutely no efforts to stop me as I pushed her skirt up to her waist.
“I know, but that’s really a you problem right now, isn’t it?” I teased, sliding my hands up her body to squeeze her tits through her top, before sliding them back down to tease her inner thighs. “Besides, do you really want to prevent me from eating your pussy?”
Kaitlyn scowled, but made no effort to stop me as I leaned in. “I hate how well you know me.”
“I think you love how good I am at pleasing you with my tongue…” I said, lightly running my tongue up one of her inner thighs before kissing it.
I kissed her other inner thigh. “…and my fingers…”
I kissed my way closer to her pussy, inhaling her sweet, feminine odor and letting it drive me wild. “…and my cock… I think you love all of this… I think it makes you absolutely crazy how much I know how to push your buttons, because you’d never thought any guy would ever be able to do this as well as I can, and how fucking addicted to me you could become if you let yourself.”
I leaned in until my mouth was only a couple inches away from her pussy. If I’d stuck out my tongue, I could have licked her up and probably made her cum in a matter of seconds, but I was enjoying this chance to make her a little crazy and just stayed where I was, taunting and looking up at her, letting my hot breath hit her pussy.
Kaitlyn eyed me defiantly while I simply knelt there and smiled my cockiest grin. It wasn’t one I busted out for many occasions, but Kaitlyn inspired it fairly easily, and I knew it got a good reaction out of her.
“You know, ever since you’ve been working on your confidence, it’s made you fucking insufferable sometimes,” she said, her voice icy.
As much as she wanted to sound bitchy about it, she couldn’t help but lock one of her legs behind my neck and pull me forward, trying to mash my face against her pussy. Admittedly, if she’d done this just a few months before, she would have been successful, but that would have been well before I’d built up the muscle and stamina I’d needed to build up this year to keep up with all the women in my life. Mind you, Kaitlyn was also fucking strong with some genuinely intense legs, so it was still an effort to resist her, but I held out just well enough to keep looking up at her arrogantly, grinning and licking my lips.
“Yeah, that’s your fault. And, be honest, you fucking love it,” I said, grinning even more broadly.
There was something in her scowl that was clearly trying to break through, and soon it became quite evident to me that this would prove to be a battle of wills between us. Would she allow her icy façade to crack first, or would my muscles give out as my mouth was forced against her sweet cunt?
We held onto that question for a moment, but soon her face broke, a small smile cutting through her scowl as a slight moan escaped her lips.
“Fuck, I hate it when you’re right,” Kaitlyn said, sighing pleasantly.
“No, you don’t,” I replied, leaning in to lightly kiss her pussy lips and getting a loud, long moan out of her. “You love it every bit as much as the sometimes-cocky bastard you’ve made sure to turn me into.”
Before she could reply, I leaned in again, kissing her pussy more firmly, slipping my tongue inside of her briefly before I set about suckling on her clit. Enthusiastically, I licked and sucked at her sensitive nub, sliding two fingers inside her in addition to massage her g-spot while I ate her with gusto. I’d had more time and experience with Kaitlyn than just about any other girl I’d been with this year, and I put everything I’d learned to the test as I set about pleasing her.
Of course, my own enthusiasm wasn’t even close to Kaitlyn’s, as she soon locked her legs behind my back, bucking against me as she tried to fuck my face.
“Oh god, oh… fucking fuck… goddamnit, I was really trying to be quick, trying to think about the others and Puma Pride, but then you had to fucking do this… why’d you fucking have to do this to me? I was gonna fuck and run and go out and join them back on the field feeling fucking sweet, and you had to do this to me instead… fuck, what am I gonna do, Ryan… what am I gonna fucking do with you… god, don’t stop… please don’t fucking stop…” Kaitlyn moaned, writhing against my face more shamelessly.
I could have given a lot of suggestions for what she might have done with me, but with my mouth full of one of the most delicious pussies in town, I wasn’t exactly in a position to actually make those suggestions. That, and the view above me was enough to make me forget my own name, let alone any suggestions I might have had.
Kaitlyn, in the throes of ecstasy, had managed to pull her tight cheerleading top up over her beautiful DD-cup breasts, showing what had to have been one of the world’s strongest sports bras barely holding back the force of her perfect tits. As I pleasured her, she had reached up to cup her tits, squeezing and massaging them as she looked down at me. Soon, though, this wasn’t nearly enough to satisfy her, and Kaitlyn pulled one of her tits free over the cup, exposing it bare to me before she tweaked her rock-hard nipple.
The lust on her face as she looked down at me, well, I’d call it inspiring, though Kaitlyn by her very nature was simply walking sexual inspiration. As a baseline, she looked painfully hot, but in this state, all of her efforts focused toward her own pleasure and losing herself to it, it made her look even more beautiful. Losing herself to pleasure was a natural state that Kaitlyn seemed to live for, and I was happy to bring her there.
Not that I wasn’t willing to unleash my playful side on her a little.
The moment she loosened up with her legs behind my neck, I pulled away from her pussy, leaving my fingers inside of her but leaning back enough so I could smile up at her smugly. The fire in Kaitlyn’s eyes had transformed into fury in an instant, and it had me grinning up at her cockily.
“Come on, you were gonna… fuck, Ryan…” she hissed, rocking her hips against my hand. “Seriously?”
“What? I thought you wanted to make this quick…” I teased, continuing to slowly massage her g-spot. Not hard enough to really get her off, of course, but enough to drive her a little mad.
Kaitlyn growled at me, continuing to rock her hips against my hand. “So that’s it, huh? That’s fucking it? You were just edging me?”
“Edging?” I said, pulling my fingers out of her cunt to stroke my chin thoughtfully. “That actually wasn’t part of the itinerary I had in mind, but it’s a fun idea, isn’t it?”
If she’d looked pissed at me before, now that I’d pulled my fingers out of her cunt, Kaitlyn looked at me as if she wished she could release all the rage of the ancient gods upon me. Honestly, half-naked and in her cheerleader’s uniform as she was, it was a pretty fucking great look on her, not that I imagined there were many bad looks on Kaitlyn Pruitt.
“Oh… you asshole,” Kaitlyn threatened, quickly reaching down and grabbing me by the wrist. “You’re gonna fucking pay for that.”
“Pay for what?” I asked, feigning innocence as she pulled me up onto the couch next to her.
“You know damn well what the fuck you’re paying for,” she continued to say in her most threatening tone possible, forcing me into a sitting position next to her. “Fucking edging me… I wanted to make this a fucking quickie before I get back to the game, and you fucking edge me? You put this on your terms when I wanted this on my terms… no way, no fucking way you’re doing that and getting away with it… no fucking way…”
She reached for the waistband of my underwear and pulled it down around my knees, letting my thick, 10” erection burst free. Though she looked furious, she seemed to funnel that into her lust, stroking my cock swiftly and spreading my precum around to better coat my cock.
“So, you’re gonna punish me?” I teased.
“Wasn’t what I had in mind,” Kaitlyn growled, leaning down and practically inhaling my fucking cock.
“Oh… gotcha…” I groaned, grabbing her head in my hand and helping her keep pace as she deepthroated my cock. “Guess I should edge you more often, then…”
She pulled off of my cock briefly, looking at me with those lustful, rage-filled eyes that turned me on more than just about anything in this moment. “Don’t you fucking dare.”
Threats aside, she put up no resistance when I grabbed her by the hair and forced her back into sucking my cock, letting me thoroughly enjoy her expertly skilled mouth.
God, by this point I’d lost count of how many times that Kaitlyn and I had gotten together, but every time we did, it was fucking magic. I still wasn’t sure what was between us, but while I knew that we were likely never going to be anything more than really close friends, if this was what “really good friends” meant with Kaitlyn, I’d be happy if we kept things like that for the rest of our lives. The fire that broke out whenever we got together always seemed to push us into greater sexual heights with each other, and more than most girls I knew, whenever we got together, it truly felt like the two of us were made for each other.
By this point, Kaitlyn was inhaling my cock with such an enthusiasm that I thought she might actually get me to cum sooner rather than later, no matter how hard I tried to hold off. This, as much as anything else, was a genuine testament to Kaitlyn’s oral skills, as well as how hot she got me. Now kneeling perpendicular to me on the couch, her bare ass sticking into the air as her skirt bunched up around her waist, Kaitlyn was looking thoroughly intoxicating. Though I still had one hand in her hair, I couldn’t stop myself from reaching over with the other to grab her ass, first kneading her cheeks, then squeezing more firmly when I heard her moan around my cock.
I could have lost myself to this moment, so naturally that was when Kaitlyn decided to pull off of my cock and look up at me with a familiar, smug-looking grin that I must have been giving her moments before.
I licked my lips, wanting to beg her for release, but knowing that that wouldn’t do anything in this moment.
“I see what’s going on here,” I said.
“I know,” Kaitlyn returned smugly, wrapping her hand around the base of my cock but not moving it in the slightest. “You had this coming.”
“I guess I did,” I replied, grinning. “But you’ve had this coming for some time too.”
She asked, “Wha-“
SMACK!
Kaitlyn yowled as I spanked her ass, hard. “What the fuck?”
SMACK!
SMACK!
SMACK!
I kept grinning down at her, enjoying the way her anger quickly transitioned to moans with every time I spanked her ass. Each spank caused a bit of that fury to melt away, and soon she was moaning like a whore, groaning and writhing while still militantly avoiding sucking my cock any more. While I would have loved that amazing blowjob to continue, at this point I was having nearly as much fun hearing her moan and cry out as I abused her ass. When I stopped, fearing she might be hurt, she let out this mewl of need that was so sweet and sexy I almost indulged her a few more impacts, but I couldn’t help the next step, really.
I just had to reach behind her and slide a finger into her tight little ass.
Kaitlyn yelped in surprise, but that surprise soon melted into a deeper, longer moan as she pushed back against my hand, fucking herself against my finger.
“Fuck… that feels good…” Kaitlyn admitted through gritted teeth.
“Thought that might be what you needed tonight,” I growled, grabbing her by the hair and forcing her to suck my cock again. “Didn’t seem like you’d be all that into a losing game anyway, so why get it quick when you can get it good?”
Kaitlyn moaned around my cock, possibly in agreement, but between my cock in her mouth and my finger in her ass, it was a little difficult to figure out exactly where her mind was at that moment. Whatever the case might have been, she was clearly enjoying herself, and with my cock buried down her throat, I was with her in embracing how fucking hot this situation was. It felt simply right to stay like this, her sucking my cock while I fingered her ass, the two of us just living in the moment as we played with each other.
Or, well, that’s what I thought anyway. I should have realized with Kaitlyn that even when I tried to play a little dominant that turnabout could be fair play.
That would easily explain why, when I felt an orgasm coming along, she pulled her mouth off my cock and looked up at me with a smug smile. My eyes widened with a hungry frustration, but it was one I knew to be unjustified, and one she understood all too well. Kaitlyn kept that smile, teasingly sticking her tongue out and lightly running it under the head of my cock. I groaned at the contact, desperate for more, but I really had to admit that I had this coming.
Nevertheless, I dug my finger into her ass, making her groan, but not enough to actually get her back to sucking my cock.
“You can be real bad sometimes, you know?” I said.
Kaitlyn smirked up at me. “You’re damn right I can. Glad to see you’ve taken some lessons to heart, but you gotta know, I’ve been bad a lot longer than you have, Ryan… I could run circles around you with how much of a bad bitch I’ve been.”
Gently, I thrust my finger in and out of her ass a little, before pulling it out. “I don’t doubt that. For now, how about I promise to stop being a jerk, and you promise to stop being a bitch, and we just fuck?”
Kaitlyn pushed herself up onto her knees and smiled. “Now that is a brilliant fucking idea!”
She crawled over to me, pushing me against my seat as she straddled my hips. Kaitlyn then bunched her skirt around my waist, making sure I got a good look at her wet, bare pussy as she ground it against my cock.
“So, are we being nice to each other here…” she purred, playfully grinding her pussy lips against the underside of my shaft. “…or are we fucking?”
Grinning darkly, I reached around to tug on her ponytail, arching her neck backward slightly so I could plant a long, deep kiss on her lips.
“I just said that I’d stop being a jerk and you’d stop being a bitch, I never said anything about being nice,” I said, kissing her again, deeply.
Kaitlyn groaned against my lips, kissing me back with a greater passion as she propped herself up on her knees. “Good. Exactly what I was hoping for…”
She reached down, stroking my cock and playfully batting it against her pussy.
Groaning, Kaitlyn continued, “You’re so fucking hard… that’s all for me, isn’t it? Or is it that me in my slutty little cheerleader uniform’s got you so fucking hard for me? Yeah, you get it extra hard for us cheer sluts, don’t you?”
Before senior year, I would have been able to answer her easily that the uniform had nothing to do with my current condition, as I’d had a pretty fucking low opinion of cheerleaders back in that day. Now that I’d had a chance to hook up with, well, pretty much all of them, I’d had a distinct change of heart on the subject of our school’s senior cheer squad, especially as more of them had shown themselves to be pretty decent people once you got to know them. Some of them were still on the bitchy side of things, to be sure, but I wouldn’t have had Kaitlyn any other way.
I kissed her again, reaching up to squeeze one of her nipples quite hard as she continued toying with my cock against her pussy. “Extra hard for cheer sluts? Obviously. Hardest of all for you, though…”
Kaitlyn moaned, smiling a surprisingly sweet, bright smile as she kissed me again. “Good answer. I’ve seen you and Brooke together, so I know you’re probably lying, but it’s still a good answer…”
I wanted to correct certain things in her assessment, but before I could, she angled herself in such a way that she could press my cockhead against her soaked pussy lips and began to settle down. No matter how many times it happened, I knew the feeling of sliding inside of Kaitlyn’s exquisite pussy to be one of life’s greatest pleasures, and the way she opened her mouth in that beautiful O of pleasure, moaning and whimpering softly as my thick cock split her tight little pussy open once more, I knew there was a certain mutual feeling to our pleasure. Kaitlyn leaned in, kissing me deeply as she pushed inch after inch inside of her.
Instinctively, I reached behind her, grabbing and squeezing her amazing ass while she settled down on top of me, savoring every sensation as her pussy massaged my cock, practically pulling everything I had deep inside of her impeccable cunt. With the sheer number of times we had done this, I was still in awe of how tight Kaitlyn felt, and decided that rather than question this feeling, I would enjoy it, losing myself to one of the hottest girls I knew once more as we continued our hot, messy joining.
When Kaitlyn settled down on my lap, every last inch of my cock finally inside of her, she let out a pleasant sigh, looking into my eyes with a fluttery, loving look that ran in stark contrast to the stone-cold, bitchy slut she liked everyone to think of her as. It was these moments with Kaitlyn that I cherished, that unexpected honesty that came when the two of us had sex, those moments when everything wasn’t just about pleasure, but was about the two of us just being with each other and enjoying each other’s company. It was moments like this where I wondered what exactly Kaitlyn and I would be to each other in the future, but chose not to question it for the good of the moment, because every moment with Kaitlyn like this was a moment worth living in.
I kissed her again, passionate and deep and swift, before grabbing her ass and encouraging her to ride me.
Kaitlyn, for her part, didn’t need much encouragement in this matter. Horny from our mutual edging, it didn’t take long for her to start gyrating in my lap, rising and falling on her knees quickly as she rode me, soon taking much of my cock with each bounce. I was more than happy to keep up with her, holding her hips for balance while I pounded up into her hot little cunt, kissing her or sucking on her tits whenever the chance arrived.
And, of course, engaging in every bit of banter with her that I could, since Kaitlyn and I had built up an impressive rapport during sex that involved more than just curses and complimenting each other on the size or tightness of our genitals.
“You know my feelings about Brooke… but that doesn’t mean I don’t get extra hard for you. You’re kinda special to me, you know?” I said, kissing Kaitlyn as she rode me.
“Oh, yeah? Fuck that’s big…” she grunted, adding a particular extra bit of emphasis to her bounce as she continued to pound down onto me. “’cause I took your cherry and all that?”
“’And all that’ covers more territory than you give it credit for,” I said, leaning in and nipping one of her nipples quickly. “You and me, that was one of those long-time coming sorts of things that neither of us really saw coming, but when it happened, it was special. And, yeah, you taking my virginity was a big fucking deal… it was really kind of…”
Playfully, Kaitlyn rolled her eyes. “If you say it was ‘magical’, so help me, I’ll-“
“It was magical,” I said. “And what are you gonna do about it, stop fucking me?”
She groaned. “You really got me cornered there.”
I chuckled, swatting her on the ass playfully. “Damn right I do. And you love being that kind of cornered, don’t you?”
Kaitlyn’s eyes blazed at the accusation, but her lips curled in a pleasantly dark smile that she couldn’t fight. “So, ‘magical’, huh?”
“Yup. They say you never forget your first time,” I grunted, fucking up into her. “And I know I never will…”
She laughed. “I’m honored… but, fuck, I wish I could forget my first time.”
“Bad?” I asked.
“Aggressively mediocre. Emphasis on the ‘aggressively’,” Kaitlyn clarified, kissing me again. “Thought he was hot shit when he was really lukewarm at best… shouldn’t be surprised really. Most first-time sex is pretty meh, so, you’re lucky you got a piece of ass as hot as mine to talk you through all the ins and outs of it all.”
I moaned as she squeezed my cock with her pussy, then leaned in for another kiss. This one was deep and lingering, and might have been deeper and longer if it weren’t for the pace we kept while fucking so savagely.
“Oh, I know I was lucky… am lucky… fuck you’re so fucking tight… after all, how many other nerds are spending one of these big game nights fucking the hottest cheerleader in school?” I laughed, leaning in again to suckle on one of her breasts.
“Oh, yeah, fuck, keep doing that…” Kaitlyn groaned, slamming her hips down onto mine. “And you’re right… so fucking right… you’re fucking lucky… I’m fucking lucky…”
“That you don’t have to see the team lose again?” I chuckled.
Even through her grunting, groaning and fucking, Kaitlyn managed to roll her eyes at me bitchily. “Oh, come on, is it so hard to believe that I actually hope they’re gonna win one of these days? I know I don’t have, like, the biggest Puma Pride in school, but I do have a little school spirit. I didn’t just become a cheer slut for all the sex and cute uniforms and my friends, you know.”
“Fair enough,” I granted, kissing her again. “But the team has always been pretty awful, as far as I understand.”
“They’re getting better. And they try hard. That’s worth something,” Kaitlyn replied. “And they’re mostly good guys… I know you got no reason to like them because of Kyle and all his bullshit, but I know you like Peter, and if you gave a lot of the rest of ‘em a chance, you’d know they weren’t all bad. Not exactly the brightest, but they’re not bad!”
Kaitlyn’s insistence was genuine, but by this point I was focusing more and more on the pressure building from our rather active sex, which made elaborate conversations like this all the more of a challenge.
“Fine, fine, I won’t talk as much shit about the football team, and I’ll yield to your school spirit,” I groaned, kissing her quickly. “Up for changing positions?”
“Oh, hell yeah, I am,” she moaned in response.
Kaitlyn quickly climbed off my cock and knelt next to me, allowing me to shift my position for a better connection. As horny as I was, and seeing her so lusciously half-naked in her uniform, there were any number of ways in which I would have loved to take her, but with memories of squeezing and spanking her ass fresh in my mind, I knew that there was only one way that I wanted her.
Roughly, I grabbed her by the hips and turned her to face away from me, allowing me to trundle up on my knees behind her (made all the more difficult by my pants still hanging around my ankles). I pulled her skirt up over her amazing ass and took a moment to appreciate the sight, running my hands over her soft, full flesh, squeezing those cheeks and wishing I wasn’t feeling so rushed, as there was a lot I would have loved to do with that ass if given all the time in the world. I couldn’t do all these things, however, but I could hover there for a moment, squeezing and massaging and trying to get Kaitlyn to make as many different sounds of pleasure as I could.
“Ohhh god…” she moaned, pushing back against me, wiggling her ass and gently flexing it against my hands. “That feels… fuck, that feels great, but I need your cock… come on, Ryan, put it back in my pussy, fuck my slutty little cunt… I need it, and you want it… so, come on, do it, fucking do it, shove that cock in me and make me your slutty little cheerleader whore!”
I loved it when Kaitlyn got that slight whiny tone. It was a little bratty and more than a little needy, but enough to get me going and do pretty much whatever she wanted. I took hold of my cock, lining it up with her pussy lips and pressing forward, making us both moan as I sunk deep inside of her delicious cunt once more. I grabbed hold of her hips, holding on tight before I truly began to pound away at her. This position granted me a lot of leverage, allowing me to properly control what we were doing and how hard. I could really get up a full head of steam on my knees like this, and the way Kaitlyn cursed and yowled and pushed back against me as we fucked, I knew it was one that she particularly enjoyed too.
“Fuck yes! Goddamn it, fuck me like that, harder, harder! Keep fucking me harder like that, fuck! Fuck my slutty little pussy with your big fucking cock… keep going, harder, Ryan, harder! I can take it! Fuck me, fuck me, fuck me hard! Ah, fuck, I love it, I love it, keep going, harder, goddamn it, fucking hell, fuck me, fuck your little cheer slut, your cum whore, do it, fuck me, fuck me, fuck me harder!!!” Kaitlyn demanded, tossing her hair over her shoulder so she could better look at me while we fucked.
Her blazing eyes only pushed me on to further beautiful depravity, fucking her harder, while taking a moment to bend over and wrap my arm around her, squeezing her tits while we grunted and groaned and fucked like animals. This was another side to sex with Kaitlyn, I’d found, for as much as we had a deep, intimate connection, once the two of us really got going, all bets were off. We were both deeply sexual creatures, and as I went to town on her clutching cunt and we both chased our orgasms, there was little that could stop us.
Not even an ill-timed interruption, like the voice that soon cleared her throat from the doorway.
“Dakota’s been wondering where the fuck you are, but I guess we should’ve known what was happening. Also, hey, Ryan.”
Without breaking stride in our fuck, both Kaitlyn and I turned our attention to the door as we caught sight of her fellow cheer squad member Jade Alvarez standing in the doorway, watching us. The gorgeous Latina cheerleader was one of the kindest and most charitable people I knew, but after a number of intimate encounters, I knew her to be every bit as dirty behind closed doors as Kaitlyn. Her pretty face and sweet smile had no way of hiding the fact that she had the body of a porn star, with a thick Latina ass and large, DDD-cup tits, both of which looked all the more impressive on her small frame. Though she looked like she was sent here to chide Kaitlyn for her absence, I could see a hint of amusement growing at the corners of her lips.
Maybe it was the fact that she was standing there watching, but I could swear I actually managed to fuck Kaitlyn just a little bit harder after Jade’s arrival.
“Hey, Jade…” I replied, squeezing one of Kaitlyn’s nipples hard enough to make her squeal.
“Ah, fuck!” Kaitlyn exclaimed, her eyes rolling back briefly before she turned her attention back to Jade. “Tell her I’ll be back in, like, a minute. Maybe two minutes.”
Jade rolled her eyes in amusement at Kaitlyn’s obvious lie. “It’s clearly going to take you guys more than one or two minutes to finish up here.”
“I dunno, I am getting close,” I acknowledged, grunting.
“Yeah, but you’re not gonna rush it, and I’m not gonna rush it, I thought you’d set those terms, and I’m gonna keep to them… you are always trying to get me to hold to my promises, aren’t you?” Kaitlyn moaned, craning her neck to kiss me.
“This is true,” I replied, squeezing her breast more intently. “Sorry, Jade… it will probably take more than a minute or two to finish this off. Is Kaitlyn’s presence really that necessary?”
Jade sighed. “I mean, no, but, Dakota’s got a bug up her butt, and she will kill the messenger if she doesn’t like what she hears.”
Knowing cheer captain Dakota Lewis as well as I did, I knew the situation was considerably more complex than that, but even if all she really wanted was the best for her squad, she was capable of being one hell of a hardass. I wasn’t going to make that any worse than I had to if I had a choice, and I was willing to come up with something that would make more or less everyone happy.
“Well, you don’t have to run back to Dakota so quickly, do you? I mean, if you went back to her right away without Kaitlyn, she’d be pissed, and I know I don’t want her to be pissed at you, and I’m sure Kaitlyn doesn’t want her to be pissed with you…” I explained.
“Well, it would be kinda funny if- FUCK!” Kaitlyn yelped as I pinched one of her nipples. “Alright, alright! No, I don’t want you to get in any trouble either, Jade!”
“Exactly what I thought,” I said, kissing Kaitlyn before turning back to eye Jade. “So, my suggestion is, why don’t you stick around while we finish off here, and then when we’re finished, you take Kaitlyn back to the rest of the squad. Explain to Dakota whatever you need to explain for why it took you so long to find Kaitlyn, and then even if she’s pissed, you still found her, and everyone walks away happy, yeah?”
“I dunno, I can see a lot of ways where someone’s gonna be unhappy with how that one shakes out…” Jade said, skeptical.
“Come on, you know you love to watch us! And we’ll get off even harder if we’re being watched…” Kaitlyn said, her devilish mind at work for a way of getting Jade in on this without having her actually steal any of my attention.
“Especially if you’re touching yourself,” I added, excited by the possibility.
Jade eyed the two of us, still fucking, while we did this, looking uncertain, but visibly turned on. Her breath had quickened, her posture was suddenly less tense… and she was clearly into the possibility, even if she was still worried about facing the wrath of Dakota. Ultimately, though, the prospect of what she’d get to see seemed to outweigh the trouble she feared, which is pretty standard when you’re given the option of watching Kaitlyn Pruitt fuck.
“Fuck…” she finally murmured, leaning against the doorframe. “Fine, if that’s how it’s gonna be… you two still better make this kinda fast… and look fucking good… if I’m watching the show, I want it to be a good show…”
Kaitlyn laughed. “Yeah, have you seen us? That won’t be a fucking problem.”
“Still…” I said, thoughtful, “We could switch things up a little, if we’re going to be putting on a good show, I mean… we don’t want to disappoint our audience, do we?”
So, with that in mind, it didn’t take a lot to convince Kaitlyn to allow me to get back into a sitting position, while she straddled my hips again in reverse cowgirl, sinking the entire length of my cock into her pussy in one swift go while Jade watched us from the doorway. The gorgeous Latina reached down, pulling up her skirt just enough so she could slip her hand under her panties, fingering herself while she watched us.
This would hardly be the first time that Kaitlyn and I had had sex in front of someone else, but I couldn’t deny the extra spark that it added for us, having an audience, particularly one as rapt and interested as Jade was. It certainly encouraged us to go at it harder, with Kaitlyn riding my cock with everything she had, while I couldn’t help but reach around her, groping and squeezing her tits lewdly or reaching down to finger her clit while she rode me. In between our long, lusty kisses, we would both eye Jade, who had gotten into what was going on quite quickly. She was unashamedly touching herself, moaning softly as she had one hand down her panties while the other squeezed at her tits through her cheerleading top.
“Oh… oh wow… oh, this is hot, this is so fucking hot…” Jade murmured to herself, loud enough that Kaitlyn and I could hear.
In the next moment that we kissed, Kaitlyn and I exchanged a cocky, proud smirk at having been able to convince Jade to stick around for this, but before long, we were back to fucking like beasts, cursing and moaning and working up a sweat as I rammed my cock in and out of her clutching cunt.
I couldn’t tell you how we were still going. With all the edging we had done prior to this, you’d have thought that both of us would have had a hair trigger, but it seemed that quite the opposite effect had actually occurred. Kaitlyn and I were working on stores of sexual energy that I doubted either of us knew we had in reserve, driven on only further by our rapt audience of one staring at us from across the room. Kaitlyn and I had seemed to reach something of a runner’s high, still going and pushing onward even well past the point of what felt physically possible, doing this now to test our limits as much as anything else.
Of course, eventually, something had to break, but fortunately for us, it was Jade that broke first. I couldn’t say how long she’d been touching herself in the doorway, but soon she let out a high cry and a shudder, groaning and shaking as her legs barely supported her any longer.
From there, Kaitlyn came next, hard and utterly devastating. I had known how loud Kaitlyn could get before all this, but even now I was surprised at the ferocity of her cry and the violence with which her body shook. Something about this angle, this buildup, seemed to collect together in a perfect storm of release that she couldn’t fight, and Kaitlyn was all too happy to surrender herself to, moaning and crying out and gushing as her orgasm tore through her.
Mercifully, I couldn’t hold on much like this either, gripping Kaitlyn tightly as I buried my cock inside of her, cumming deep and hard. Awash with pleasure, I almost descended into a blissful blackness, but managed to hold onto my consciousness as I gripped her close to me, kissing her and moaning against her lips as we both came down.
After all the teasing, it felt a fitting end, and one that would’ve been good to linger on if Kaitlyn hadn’t chosen that moment to sigh and climb off of me.
“We really gotta get back to the game,” she said, her tone apologetic even if her attention was directed at Jade.
“Yeah… yeah we do…” Jade replied, shakily standing up and wobbling toward Kaitlyn.
Kaitlyn quickly redressed herself, even recovering her panties from the desk she’d stashed them on and sliding them up her legs. Given the river of cum I’d shot into her that was now snaking its way down her leg, I didn’t know how much good the panties would do her, but I didn’t really care.
Cocking my head to indicate her legs as I got dressed, I said, “You really gonna go out like that?”
Kaitlyn smirked. “Wouldn’t be the first time I’ve gone out there all leaky with cum…”
“It really wouldn’t be,” Jade confirmed, chuckling.
I chuckled. “Shameless.”
Playfully, Kaitlyn curtsied for me, then said, “Guilty as fucking charged… but, come on, you know you love me…”
Though she had cleaned herself up a little and more or less straightened out her uniform, it would be impossible for anyone to miss the fact that she’d clearly just been fucked. From the flush in her face to the way her hair was tousled and that unmistakable trail of cum down her leg, Kaitlyn Pruitt did look utterly shameless in her own delightfully slutty way.
Standing up as I redid my pants, I quickly leaned in and kissed Kaitlyn. It was a quick kiss that lacked much of our fire, but one that left the both of us smiling.
Grinning, Jade walked out of the office and said, “I’m gonna give you two a moment. Not a long one, ‘cause we really do need to get back to the game! But you still need one, I think.”
Kaitlyn wrapped her arms around my neck, smiling and kissing me again. “She can be such a drama queen sometimes.”
“Yeah, but she’s still pretty fucking awesome,” I said.
“No doubt,” Kaitlyn replied, sighing pleasantly as she kissed me. “You gonna stick around for the rest of the game? I know you’re probably gonna want to wash up after everything we did, but if you stick around, you can grab a shower with me and the rest of the girls after the game… who knows what’ll happen then…”
I thought about this offer for maybe a fraction of a second before grinning and reaching down to grab Kaitlyn’s ass. “Of course I’ll stick around for that. You know, you really know how to spread that Puma Pride…”
Grinning, she kissed me and teased, “You have no idea…”
Comments
JetstreamSamBestWaifu
god they really need to admit they're in love already
J Bone
I think at the end of this storyline Ryan will end up with Kaitlyn.
