Senior Year Memories Ch. 39

Riley's eyes rolled back and she let her tongue hang out playfully, moaning and groaning and making the cutest damn squealing noises as she continued to bounce on my cock. She was working up a pretty good pace at this point, taking my cock with almost every bounce while sweat began to bead on her body. Every time she took my entire length, she uttered a high, short exclamation. Riley looked like she was having the time of her life.

I wanted some of that myself.

"You ready to switch things up?" I grunted, squeezing her nipples between thumb and forefingers.

"Sure!" Riley wailed as she took my length again, before giggling. "Whaddya got in mind?"

"This," I said simply, wrapping my arms around her the next time I was buried completely inside of her. I held her close, and tight, enough that I could roll over onto her without much difficulty. Riley squealed at the sudden reversal of fortune, but clearly had no objections as I took my now dominant position above her.

It was a strange place to be in, towering over such a slight, small girl while buried deep in her epically tight cunt. Riley looked up at me with such beautiful, innocent eyes, but there was no innocence to her smile, or the way her body flushed and responded to my efforts.

"You think you can do it? You think you can really fuck me like I gotta be fucked? Because a lot of guys have tried, but this tiny, perfect little slut... there's no one like me..." Riley challenged, playful.

"No one *quite* like you," Kitty said, reaching over to hold her best friend's hand as I began to fuck her.

Riley interlaced her fingers with Kitty's, and agreed, "No one *quite* like me, 'cept my twinsie here."

"Damn straight," Kitty replied. "And don't you forget it."

These two could have gone on for some time, I was sure, but in the moment, I really didn't care. I was building up to a good load of cum, and given this opportunity to really fuck Riley, I was going to give her everything I had. I quickened my pace, thrusting in and out of her more rapidly, giving her much of my length with every thrust. Riley's smile brightened at this, her eyes staring into mine as I fucked her nice and hard.

"You like that?" I grunted, pumping into her. "You like that big fucking cock?"

"I love it! It's so fucking big! Bigger than any I've ever had, I need it, I need it, please, keep going, I want you to cum... I wanna cum... please cum for me and make me cum! Cum for me and make me cum!" Riley demanded.

"I can help with that," Kitty said, taking her hand from Riley's and reaching over to rub her friend's clit.

"Oh, yesssssssss!" Riley groaned deeply as Kitty and I fucked her.

"Give it to her, Ryan..." Kitty commanded, her voice husky with need as she shuddered with her own impending orgasm. "Do it, fucking do it, give her everything, fill her tight little cunt with all your cum, fill her up... make her a messy little slut... give her every fucking last drop of cum... make her take it... do it, fucking do it... fill her slutty little hole, but make sure to save some for later..."

"What happens later?" I grunted, painfully close to my own orgasm, a state that Riley and Kitty seemed to be teetering on the edge of as well.

Kitty grinned. "Me, obviously... and then our asses, of course... because all us good cheer sluts love having our asses stuffed, and I bet you've never had asses as tight as ours..."

"OHMYGOD OHMYGOD OHMYGOD, I'M CUUUUUUUUUUUUUUMMMMMING!!!!" Riley cried out, wrapping her arms around me tightly as she came. It was as if she had been hit by a truck, her entire body jolting against mine violently as her pussy squeezed my cock tightly. Even if I'd had all the restraint in the world, nothing at this point could have stopped me from grunting and unleashing inside of her. Even through her tightening, I pushed in with one last, conclusive thrust of pure, unrestrained physical need, and I came. Like they wanted, I filled her deep with an utter torrent of cum, a flood with a volume that I hadn't adequately prepared for.

"Yes, yes, yes, I can feel it!" Riley squealed.

She looked so pretty, I just had to lean down and kiss her. It was nice in this moment, having her close and underneath me like this, feeling briefly like it was only the two of us in this room that mattered. With my cock still buried deep inside of her, there was something like a moment of peace between the two of us.

Of course, in situations where there are more than two people in bed together, that peace is often quickly annihilated by the third party.

"Well, that looked like a lot of fun. You certainly seem full of... cheer," Kitty said, her voice full of mischief as she quickly kissed Riley.

"That's not the only thing she's full of," I quipped.

Giggling, Riley poked me in the side. I protested, "Hey! Someone had to say it!"

"He's right, you know," Kitty said.

"I know, I know," Riley joked. "I'm just coming down still, I could use a moment..."

Taking this as my cue, I slowly pulled out of her, climbing off of Riley and dropping onto my back next to her. My cock had half-deflated by this point, but with these two tight minxes, I doubted I would stay that way for long.

"You could use a moment... I could use a turn with Ryan..." Kitty protested, playfully climbing on top of Riley and making out with her, before turning to me. "If we keep going like this, it'll get you hard soon, right?"

Seeing how far I could push this, I said, "It's... not bad. Though I think you can do better."

Pretending to be scandalized, Kitty dropped her mouth open. "He thinks we can do better, Riley."

"*I* think we can do better," Riley said, grinning and pushing Kitty away from her, before sitting up. The tight little blonde had the most beautiful just-been-fucked look about her, her skin flushed, her hair and makeup mussed up, her pussy still leaking copious amounts of cum. She looked so gorgeous... I needed to make this a memory.

"Can I get a picture of you like this?" I asked Riley.

"Like this, sure," Riley answered with a giggle, giving me a chance to get my phone from my pants. "But I think you'll like this next part better."

"Yeah?" I asked, snapping a shot of just-fucked Riley as Kitty sat up opposite her.

"Yeah," Riley replied, spreading her legs and interlocking them with Kitty's, the two of them pressing in close and grinding up against each other, scissoring.

"This isn't as fun as some things..." Kitty said.

"Speak for yourself, I'm having a fine time," Riley replied, grinning.

"...but we have fun with it," Kitty finished.

"We have fun with everything," Riley said, grinding up against Kitty insistently, the two of them increasing to a furious pace. Almost on auto-pilot, I snapped a number of pictures of them like this, watching as these two tight little cheerleaders ground against each other, moaning and writhing and making this look really good.

"See, when you do everything together, you get to know each other really well, and that's the best," Kitty said.

"Yeah, right?" Riley giggled, moaning and furiously humping her hips against her friend. "It's like I don't even have to ask anymore, if I'm in need, she's there."

"Like you're there for me," Kitty moaned. "Doing everything together."

"Mhm. Cheer together," Riley groaned.

"Fuck together," Kitty replied.

"Graduate together," Riley continued.

"Keep fucking together," Kitty laughed, moaning and looking at her friend seductively.

"Go to college," Riley suggested.

"Get married at the same time," Kitty said playfully, moaning.

"Get pregnant at the same time," Riley said.

"Probably," Kitty admitted, looking down at her pussy. "Though with all Ryan's cum dripping out of your pussy onto my pretty little lips, that might have already happened."

Eyes lidded over with lust, Riley quickly looked at my flash of worry and said, "She's joking."

"I am joking," Kitty admitted. "You've got nothing to worry about."

"Nothing at all," Riley said, rocking her hips against Kitty's with a greater urgency.

"Though how you haven't knocked up half the cheer squad already... that's a big mystery," Kitty groaned.

"A *huge* mystery..." Riley moaned, shuddering as she got closer to some resolution. "Unless he already has..."

Kitty laughed, a lusty and wild cry. "Now wouldn't that be something..."

Watching the two of them building to some great, mutual orgasm while teasing each other, and me with this beyond dirty talk... it was a powerfully erotic sight. The way they worked in unison with each other, with perfect sync and coordination, knowing exactly what each other needed and delivering without words or questions, it was amazingly hot. My erection was back, and in force, stronger than it had been earlier in this threesome, even. It was only with the greatest restraint that I didn't touch either of them, simply stroking my cock and setting my phone aside as they ground against each other.

I wondered which of them would cum first, when I should have known that of course it would be at the same time. Seeing the two of them climax in unison, jolting and shuddering and shaking hard, embracing each other as they kissed and rode through two powerful cums, they were painfully hot.

Once they had come down somewhat, I knew I couldn't hold back anymore. I clambered across the bed toward them, wrestling them apart and tossing Kitty aside. At first, Kitty gasped with surprise as she landed on her ass next to me, but when I sat next to her, utterly dwarfing her with my size while my cock throbbed with need, she looked up at me with her beautiful green eyes expectantly.

"Well?" Kitty growled, her face innocent while her smile was undeniably devilish as she licked her lips. "What are you waiting for?"

I didn't have a good answer for that. What I did have, however, was a raging erection that I meant to have inside of her very soon. I was more beast than man by this point, the show the two of them put on awakening a primal side of myself I saved for such occasions. I would not go too wild on her, no, I would never hurt either of these girls, but I knew that this was probably going to be harder than the last go.

Reaching over to Kitty, I grabbed her by the hips and pulled her towards me, lifting her so she was straddling me. She planted her feet on either side of me, then squatted, pressing her tight pussy lips against my cock. She wasn't quite as tight as Riley, but was still tighter than most of the other girls I'd been with this year. Even with her pussy utterly soaked with her juices, and a little of mine for that matter, this would still be a tight journey.

Nevertheless, Kitty had very little of the hesitation that Riley had had, and once my cockhead was lined up with her entrance, she began the slow, forceful trip downwards. I held her tight, wrapping my arms around her while I supported her ass, helping her slowly descend. Her pussy lips spread for me welcomingly, the head of my cock slowly slipping into her achingly tight cunt.

"Ooooh... this is going to be difficult... but I can make it, I can do it... I want you in me, stretching me, filling me, breaking me like no guy's ever been able to before... yes, right there, right there... YES!" Kitty cried out triumphantly as my cock broke through and buried almost half its length inside of her hot, wet cunt.

Kneeling behind her friend, Riley got down on her hands and knees between my legs and looked at Kitty being impaled on my cock from point blank, so close I could feel her breath on my balls. She exclaimed, "Oh, wow, you should see this up close, this is insane!"

"I know exactly how insane it is, Riley, thank you very much," Kitty groaned, her eyes pinched tightly shut as she unhesitatingly slid further down my cock until every last bit was buried inside of her. Once she had all ten inches inside of her and sat on my lap, Kitty squeezed me from inside, playfully. I kept holding her close, moaning and grinning, leaning in to kiss her.

"Squeeze me again, and I'm gonna swat that ass," I threatened, grinning playfully.

"Yeah?" Kitty said, squeezing my cock playfully.

Reaching back, I gave her one playful spank on her tight ass. Kitty yowled, but I held her ever closer, grabbing her ass and helping her rise and fall slowly on my cock. I said, "I told you."

"He did; I heard it!" Riley exclaimed.

Kitty rolled her eyes, sliding her feet backwards until she was kneeling, better allowing her to rise and fall on my cock.

"Whatever... I'm finally getting to fuck Ryan Collins... and it's pretty fucking awesome..." Kitty said.

"You're pretty fucking awesome..." I groaned back, kissing Kitty and looking over her shoulder to see Riley now kneeling behind her best friend. "...both of you."

"Awww, thanks!" Riley exclaimed, reaching around Kitty to squeeze her friend's nipples as she rode me. "If you think that's awesome, you should see this!"

In a daze from how hard she was riding me, Kitty could only ineloquently say, "Wha?"

Her question was answered pretty quickly, as suddenly one of Riley's hands disappeared behind Kitty. Then, there was a distinct additional pressure inside Kitty's pussy as she rode me, followed by her eyes going very wide, and a single harsh exclamation escaping her mouth.

"MOTHERFUCKER!" Kitty declared, moaning from the deepest recesses of her soul.

Riley leaned around to look at me, smiling cutely. "In case you were wondering, that's what it feels like when I've shoved a couple fingers up her butt!"

"Nice," I commented, grunting as I fucked up into Kitty. "But if you think that's a lot, just wait until I've got my cock up your ass."

"That a promise?" Kitty grunted, her face a mask of lust and need as she fucked me harder.

"Yeah," I replied, groping and squeezing every bit of her I could get as she fucked me.

"Good," Kitty said, wrapping her arms around my neck and kissing me deeply. This was a different Kitty from the one I'd met at the In-N-Out, with no pretenses of eloquence or culture. Sandwiched between Riley and me, she was a monster driven by a pure need for sex, spurred on by my cock, my mouth, and every square inch of her best friend, Riley, who gave Kitty everything by fingering her ass, as if staking her own claim on her friend in this threesome.

Messing around with these two carried with it a different power dynamic than I was used to, one where I became more certain with each passing moment that I was kind of a toy to them, along for the ride while they did their own thing, unless I took matters into my own hand. While the ride was something I was happy to be going along for in this moment, since these two little sluts were really, *really* fun, I also knew that there would come a time where I had to seize the moment and take whatever I wanted.

And what did I want? I wanted to be remembered. I wanted to leave an impression. I wanted to be more than just that guy with the big dick they got on loan from their friends.

So, when I could tell Kitty was getting close while riding my cock, I pulled her off of me and dropped her to the bed beside me. This left Kitty making desperate, disgruntled noises of absolute need, while Riley fell back, confused, but I had a plan.

I got up onto my knees, then grabbed Kitty, rolling her over onto her stomach and pulling her hips back up so that she was now on her knees, face down, ass up. Reaching down, I lined up my cock and slid it back deep into her pussy, holding onto her hips and pulling her in for a serious fuck.

"OH, GOD, YEEEEEEEEEEESSSSSSSS!!!" Kitty cried out as I buried my cock all the way inside of her and began to pound into her. "GODDAMN, HE'S SO FUCKING DEEP! HOLY SHIT! FUCK! HE'S FUCKING ME SO HARD, YES, KEEP GOING, KEEP GOING, RYAN, PLEASE! KEEP FUCKING ME!"

I didn't need to listen to her as I grunted, pounding away at her impossibly tight cunt. Her body pressed against mine, her small tits shaking and her tight ass jiggling with every thrust as I fucked away at the tight-bodied, redheaded cheerleader. She forced herself up onto her hands, looking back at me with a look of surprise and overpowering want, her headband askew and her eyes glittering with delight as I fucked her like she seemingly needed to be fucked.

Riley looked on, somewhat stunned at this development, but smiled at me as if she understood what was going on.

"Fuck yeah, Ryan... do it, fuck her harder! Give it to her, fuck her like a cheap little whore, fuck her, fuck her cunt, fuck her and fill her up, give her every fucking drop! Give it to her, give it all, give it to her like you fucked me and filled me up! Make her scream!" Riley encouraged.

"Working on it..." I grunted, fucking Kitty as I felt my own orgasm building again.

"You want me to scream? You really want me to scream? Fine, I'm gonna scream... I'm gonna CUUUUUUUUUUUUUUUUUMMMMMMMMM!!!" Kitty cried out, pressing against me as her body was overtaken by another orgasm.

Riley leaned in to hold her shaking, shuddering friend, while I got in my last few strokes before Kitty's clutching cunt squeezed down hard on me and made me cum yet again. While it may not have had the same volume that my orgasm that filled Riley's pussy had, this one might well have been harder, as Kitty was, in this moment anyway, certainly a more passionate lover. I buried deep within her, making sure she got everything from my last few strokes, before I had to pull out and collapse on the bed next to these two girls. The sight of Kitty's pussy, bright pink and red from the exertion and just dripping with my cum as if I'd now planted my own claim on her... yes, I had gotten what I wanted from her.

I lay on my back on the bed. Riley curled up on my right side next to me, snuggling in for a kiss, while Kitty took her place on my left, kissing me as well.

"We should've done this sooner," I said, grinning. "We all should've done this a *lot* sooner."

"We'll make Dakota's next orgy... I promise," Kitty said.

"Promise... it was stupid we missed out on it then..." Riley replied.

"So stupid..." Kitty said, sighing contentedly and running her fingers down my abs.

"Very..." Riley replied, doing the same, grazing her fingers on the underside of my cock, making it twitch, slightly.

Now, while this had been a pretty hard fuck, I was still feeling pretty good, and though Riley and Kitty appeared to still be basking in the afterglow, I knew that I could push this to the next level.

"You two don't think we're finished yet, do you?" I said, reaching down and squeezing each of them by the ass. Reaching even further, I ran my middle finger down the cracks of their asses, pressing against their tightest holes as the pair of them squirmed and giggled.

"I guess we're not finished yet," Riley said.

"I guess not," Kitty added. "Seems like we're going to get our asses nicely fucked."

"Seems like it," Riley replied.

"I don't know about you two, but I think it'll cheer me the hell up," I said.

"Oh, I'll certainly be cheered. Won't you, Riley?" Kitty asked.

"Definitely," Riley answered, smiling broadly. "I mean, I'm already pretty fucking happy after all this happy fucking, but I think a little more would be great. If Ryan's ready for it, anyway."

Looking down at my cock, now almost completely returned to full strength, I said, "Let's do this."

The two of them looked into each other's eyes, grinned, and each kissed me on the cheek before quickly and perkily cheering, "Goodie!"

***

It would be an understatement to say that I simply got better acquainted with Riley and Kitty's asses, because in the next couple hours I might well have gotten better acquainted with them than any other guy they'd been with. My mouth, my fingers, and of course, my cock, all got to understand each of these tight little cheerleader's asses by the end of our time together, filling and fucking them time and again, making the two tiny sluts cum over and over again as I fed my thick cock into their tightest holes. My memory is a hazy blur of everything that came after, ending somewhere with me holding Riley, pinned against the wall and folded in half as I roughly fucked her ass while she came, before letting her down to the floor and cumming all over her and Kitty's smiling faces as they knelt before me.