Senior Year Memories Ch. 39

This, more than anything else, finally did it for her. Kitty jerked on top of me, crying out through Riley's kiss as her whole body was overtaken by a powerful, shaking orgasm. A flood of her juices burst onto my face, and though it felt like I might drop her, I was able to hold on. As she moaned and quivered, I continued licking and suckling at her clit, drawing out her orgasm as long as possible until she was a shivering mess.

Finally content that she had reached the end of this cum, I lowered her to the ground in front of me, helping her slowly drop to her knees as she faced me. Kitty looked so drained, so utterly satisfied. She leaned in to kiss me, eagerly licking and sucking her juices from my face as we made out. Riley was quick to join us, kneeling next to us and savoring her friend's juices, pulling at the remains of Kitty's top and tossing it aside until Kitty wore nothing but her cat-eared hairband.

"That was... stellar," Kitty said.

"I know," I said, kissing her deeply.

"Tell me about it," Riley said, dropping her pants and panties to the floor, leaving her now every bit as naked as Kitty. Much like her friend, her pussy was shaved, and looked at once utterly enticing and completely intimidating. Her folds were prominent and already beaded with her no doubt sweet nectar, but much like everything about her seemed utterly scaled down when compared to me. I'd been in plenty of tight pussies before, but these two... they might prove a challenge, no matter how much big dick they'd fucked before.

Still, Riley was completely nonplussed by any skepticism on my face as she knelt down beside us, leaned in, kissed Kitty, and continued, "That looked like it was *so* much fun!"

Breathily, Kitty looked at me, nearly smitten. "Trust me, as fun as it looked, it felt about a million times better."

"Mmm," Riley groaned, looking at me lustily. "I can't wait..."

Looking down at her now naked pussy, I said, "Well, I'll be more than happy to eat you out too... we are here to cheer you up after all..."

For emphasis, I reached down and slid two fingers up and down her slit, before pressing my middle finger gently inside of Riley. She closed her eyes tightly, biting her lip through a moan, then said, "Yes... yes you are."

"I'm really sorry about that," Kitty said, looking a little embarrassed. "In a sorry-not-sorry way, of course."

Seeing the way I casually fingered Riley, Kitty grabbed my other hand and placed it between her legs. Though clearly still quite sensitive, she was happy to moan with Riley as I fingered the sexy, petite friends.

Now that she was getting fingered as well, Kitty continued, "Ryan was just so much fun, but this really was supposed to be your day... sorry I hogged him first."

"I'm not," Riley said, kissing Kitty quickly and reaching up to gently massage Kitty's left tit. "I wanted to see this, and I got what I wanted, and it was so fucking hot, watching Ryan eat you out like that... god, I got soooooooo fucking wet."

"I can tell," I replied, pressing my middle finger even deeper into Riley's impossibly tight cunt. "But the offer still stands, I'd love to eat your pussy if you want it."

"Mmm," Riley groaned, closing her eyes briefly and grinding her hips against my hand. "That does sound really, really good. But there's something I think that would make me even happier, Ryan..."

"Yeah?" I asked. "What's that?"

Looking straight into my eyes with her innocent blue orbs, Riley said, "I really, really wanna see your cock."

"Yes, I'm sure that's all you want to do," Kitty said, playfully rolling her eyes.

Riley sighed and rolled her eyes back. "You know me too well."

"Twinsies," Kitty said, smirking.

"Twinsies," Riley agreed.

Looking to put me out of even a confusion as brief as this, Kitty clarified, "I might've said that Riley's a slut for huge cock, but I don't think there are words adequate enough to describe just how much a huge cock will drive her completely insane. Is that a fair assessment, Riley?"

"I think you're still selling me short," Riley said, looking at me and licking her lips.

"Well, you heard her... I could tell you what you're in for, but I think you might have a lot more fun standing up, taking off your pants, whipping it out and seeing where things go from there. I don't think you'll be disappointed," Kitty explained with a grin.

"I don't think I will be, either," I agreed, standing up and unbuckling my belt. "Just understand, that you might have heard stories, you might have seen pictures, you might have even had what you've thought to be every big cock in school... but I have it on very good authority that I've got the biggest in all of Regan Hills High School... so, yeah, you've been warned."

"We've been warned, got it," Riley said, cocky.

"Consider us thoroughly warned," Kitty replied, amused.

I unbuttoned my pants, but they still seemed to be treating this as a most delightful joke.

"I can take pretty huge dildoes," Riley said.

"Right? Some of them are pretty fucking huge," Kitty confirmed.

"Way huge," Riley said, nodding confidently.

Dropping my pants to the floor, I hooked my hands under my waistband. I did this in such a way as to cover most of my cock from their view. Call me a tease if you want, but in my position, I felt like a little tease was in order, especially with two tiny, naked cheer sluts just waiting for me to unleash my cock upon them.

"We can take it," Kitty said, confident.

"Yeah," Riley agreed.

"Alright, if you say so," I said, dropping my underwear to the floor and letting my very thick, ten-inch cock spring out for their approval.

Simultaneously, Riley and Kitty's eyes went wide, their mouths dropping open as they took in my giant dick. Words took a while to find them, but when they did, it was with the kind of eloquence I would have expected given their reaction.

"HOLY SHIT!" Riley and Kitty exclaimed in unison.

Grinning with no small amount of stupid, masculine pride, I said, "I did warn you."

Kitty looked positively shocked at the actual sight of my cock, arching her neck slightly to take in every angle, from the swollen purple head, to the thin trail of precum leaking down, to my large, and now very full balls.

Riley was nowhere near as timid. Though her mouth was still open in some form of awe, she quickly acted on it, reaching out with one of her tiny hands to quickly touch my shaft. When it twitched in her hand, she darted away reflexively, giggling. Then, as if she felt very silly, she reached out again, wrapping as much as she could around my cock.

"Wow," Riley said, softly, "I don't even think I could get around it with both hands."

Soon, she tested this theory, confirming that she actually could do this, but not without some difficulty.

"I might have to revise my theory on whether or not you could actually get all of it down," Kitty said.

Riley looked scandalized, slowly jacking my cock, spreading some precum on her thumbs while toying with my cockhead (making me hiss in a very pleasurable manner in the process) before spreading it down my cock with her hands.

"You don't think I can take it?" Riley teased her friend, jacking me more eagerly.

"I don't see how *anyone* could take all of that," Kitty said, still in a little bit of frightened awe while looking at my cock.

Leaning in, Riley kissed the head playfully, looking at me with her big blue eyes and smiling playfully. I groaned at her touch, especially when she stuck her dainty tongue out and gave the slit the slightest of licks.

Still jerking me, Riley replied, "If a bitch like Gwen-motherfucking-Savage can take it, I can take it."

"Gwen definitely could suck it all down," I acknowledged. "She may lack charm, but she can handle a cock impressively."

"See? If she can do it, I can totally do it," Riley said, confident and not letting up in her pace as she jacked me.

"Sound reasoning, but I'm still doubtful," Kitty said. "But, give it a shot! Surprise me!"

"Oh, I'm gonna surprise you," Riley said, looking up at me and licking her lips, only a couple inches away from the head. "I should warn you... I'm really good at this."

If her oral skills were anywhere close to matching what she could do with her hand, I was in for a treat. I said, "I believe you."

"Good," Riley said, opening her mouth wide, and stretching her lips over my cockhead.

I groaned as she took it in easily, but looking down at her like this, her mouth stretched beyond what looked a natural limit, her eyes wide with surprise yet still holding a look of pure determination... it might well have made me harder. Riley's tongue danced over the cockhead, making me shiver and moan as I placed my hands on her head. She sucked a little more in at once, and then, with laborious precision, she began to bob on me, taking a little more every time.

"Holy shit..." I groaned, watching as she took more than half my length with one bob.

"Holy shit," Kitty agreed, watching as Riley took another inch.

This process quickened, faster and faster, with an eager, determined Riley, her eyes tearing up and drool snaking down the edges of her mouth as she fucked me with her face. Then, with some triumphant finality, her nose touched my skin and her chin rested against my balls, the entirety of my cock buried down her throat. She looked up at me with watery eyes that were so excited, so proud of what she had done.

With that done, she pulled off of my cock, coughing and gasping, looking a complete mess but smiling oh so smugly over at her friend.

"Toldja..." Riley said, coughing wetly.

"You did, you did, I admit it, you got me," Kitty said, reaching up to grab my cock. "Well, here goes nothing..."

Kitty had considerably more trouble sucking my cock than Riley did, maybe maxing out at about three quarters, but she gave it her best and could easily match Riley for her enthusiasm. The two of them took turns playing with my cock, with one of them sucking as much as they could while the other licked my shaft or sucked my balls or played with her friend. It was an unbearably erotic sight as these petite sluts worked in expert tandem. They knew each other well, never getting in each other's way, knowing exactly what it took to maximize their efficiency and make my cock feel amazing.

"Unless you want me to cum very, very soon, and all over both of you," I groaned, my hands in Riley's hair while she sucked my cock in deep and Kitty licked my balls. "I would advise slowing down... this feels so fucking good, and you two are-"

Letting my balls pop from her mouth, Kitty suggested, "Sublimely talented little sluts?"

"Yeah, that works," I replied.

Kitty turned to Riley, kissing her neck. "Do we want him cumming now, Riley?"

"Not yet," Riley said, taking my cock from her mouth and slowly jacking it with both hands. "I mean, I love cum."

"Like you know *I* love cum," Kitty confirmed.

"But I'm not ready for it yet. Not in my mouth, not on my face, not yet," Riley continued.

"Then where and when?" Kitty teased, full-well knowing the answer as she looked up at me.

I looked down into Riley's eyes as she smiled at me sweetly. "When? Pretty soon. And where? Deep in my tiny, tight little cunt. Does that sound good to you, Ryan?"

I licked my lips, not needing to put a lot of thought into my response. "Sounds perfect."

"Yay!" Riley exclaimed, kissing the tip of my cock playfully before standing up, taking it in hand, and guiding me over to Kitty's bed while more or less pulling me along by my cock. Kitty was shortly behind us, bouncing up on the bed next to us as first Riley, then I climbed up onto it after her. The three of us jockeyed for space and position on the bed for a moment, rolling around laughing and groping and kissing each other, before I rolled onto my back between the two of them, wrapping an arm around each of them. Riley and Kitty felt so light and insubstantial with my arms. If it weren't for their tight gymnast's muscles, I felt like I might crush them.

Kissing first Kitty, then Riley, I looked deeply into the blonde's eyes and asked, "So... how do you want to go with this for the first time?"

Riley's eyes practically sparkled when I said "the first time", clearly happy at having more than one chance to seriously fuck.

"I think I wanna..." Riley said, looking down at my cock while she eagerly touched herself.

"You want to... what?" Kitty teased.

"Don't rush me! There's a lot of good options!" Riley exclaimed, rolling her eyes.

"I'm not rushing you... not thoroughly, anyway, but if you take too long, I might have to jump on myself..." Kitty teased.

"NO!" Riley yelped, rolling on top of me, straddling my leg. "No, I got first dibs; if you wanna cheer me up, I get first dibs!"

Kitty grinned, waving at my cock almost as if it were a dare to Riley. "Then by all means... be cheered!"

Kitty licked her lips, looking down at my cock. Tentatively, she reached down and began stroking me again, grinding against my leg with her tight, wet pussy. Whatever big game she talked with the other girls, and Kitty in particular, she clearly wasn't 100% ready for this, even if she really wanted it. Her hands felt so small on me, I could only imagine how tight her pussy would feel.

"I think... I think I wanna be on top," Riley said.

"Only if you're sure," I said.

"I'm very sure," Riley said, determined and grinning broadly. She swung her leg over me, so now rather than just straddling one of my legs, she straddled my hips. Gingerly, she slid up until her pussy was rubbing against the base of my cock. Riley stayed there for a moment, rocking against me, grinding her clit against me. It was a slow, delicious process, one that had her moaning and quite wet.

"This is crazy..." she said, planting her feet on the bed and crouching above me, running her pussy against my shaft until I felt her deliciously hot, tight folds resting against the head. She stayed crouching like this, reaching between her legs to hold my cock steady.

Encouraging her, Kitty got on her knees behind Riley, holding her hips steady. "You've got this. I won't lie to you, it will be a challenge, but you have this."

Riley leaned back, kissing Kitty. She did this, moaning, and applying gentle pressure as she settled her weight onto my cock. Her pussy lips were hot, and wet, so very ready, and seemingly an impossible fit. I groaned at the contact of her pussy against me, but looking down, it just did not look like this was going to happen. Even as she put more pressure onto me, settling slightly more weight with Kitty's slow encouragement and arms wrapped around her friend, it just seemed like Riley could not fit under any circumstances.

"Come on, come on, you can do this..." Riley said, closing her eyes in determination and gritting her teeth.

"You've got this..." Kitty intoned, looking down at me and smiling confidently. She had a lot more confidence than I did in this moment, but, it was encouraging.

I ran my fingertips up Riley's legs, teasing her, encouraging her, making her shudder and break out in goosebumps as a light moan escaped her lips. She settled down more of her weight onto me, her face screwed up in determination and need. Something changed, I couldn't say what, but her angle shifted, the tension between us breaking ever so slightly. It felt like something moved between us.

And then, there was no longer a between us, as with one determined rise and fall of her hips, Riley buried the head, as well as a good few inches of my cock, deep in her pussy. I know I've said some girls were painfully tight before when I'd had sex with them, but by far, none of them compared to Riley Richardson's cunt. It was hot, and oh so very wet, but the tightness would have threatened to hurt me if I weren't so turned on right now. I was buried in one of the tightest, most exquisite pussies in school, and I was only a few inches deep.

While I was held in stunned silence at this entry into the ultra-petite cheerleader, Riley was no longer beholden to the former status quo.

Her eyes flew open.

Her jaw dropped.

"MOOOOOOOOOTHERFUUUUUUUUUCKER!!!!" she screamed, her whole body wracked with the sensation of being filled by a bigger, thicker cock than she had ever felt before.

"It's alright, it's alright, you're alright," Kitty said comfortingly, holding onto Riley, while craning her neck around to get a look at her friend being penetrated. "Holy fuck... you're positively impaled on his cock!"

"Not yet," I groaned, shivering myself as I ran my fingers up Riley's thighs. "Only a little way in... holy fuck, you're so fucking tight."

"You won't find any tighter..." Riley grunted, settling down a little more weight onto my cock. She squealed lightly, a sound somewhere between pleasure and pain but probably consisting of both.

Still, it was with great determination that she forced more of me into her, until she'd taken more than half of my length. I watched my dick disappear into this tight slut, amazed that she kept feeding inch after inch into her. It couldn't possibly fit; she couldn't possibly take it. She doubted herself, Kitty might have doubted her, it just didn't seem physically possible.

And then she did it. Riley Richardson, all 4'8" of her, a girl so tiny it looked like a stiff breeze would blow her away and who was normally so blonde and perky and wholesome-looking you would never have imagined it possible she'd even consider doing something like this, had every single thick inch of my ten-inch cock buried to the hilt in her steaming cunt.

Riley shivered, her mouth dropping open wordlessly, seemingly held up only by Kitty at this point. They both looked down at her obscenely stretched pussy.

"Wow," Kitty said.

"Wooooooooooooow..." Riley moaned, pushing Kitty gently away and falling down on me. Riley clung to me for a moment, shaking and shivering as she stayed impaled on me.

"You're... you're fucking amazing..." I groaned, holding Riley close and kissing her.

Riley put her hands on my chest, pushing off of me and smiling. "Yeah?"

"Yeah," I confirmed.

She grinned broadly. "Cool. You hear that, Kitty? I'm fucking amazing."

Sliding onto the bed next to us, Kitty pulled up a pillow to prop herself up. "*I* could have told you that, Riley. Anybody who doesn't understand how amazing you are does not deserve your time or presence. Like Br-"

"FUCK BRENDAN!" Riley exclaimed, rocking her hips on mine, bouncing on my cock enough to make me moan. "Ryan here's waaaaaaaaaaay fucking better."

"Thanks," I said, squeezing her ass playfully, before my own greedy side snuck through. "You ready to fuck? Because if I'm being honest, I really, really want to fuck you."

"You better do as he says," Kitty teased, reaching between her legs to touch herself while Riley built up a pace. "A big cock like this doesn't come around very often, you want to savor the experience."

"I know," Riley said, pushing herself up so she was sitting on my cock again, building up a pace where she was slowly bouncing up and down on my lap. "God... it's so fucking good..."

"Though I guess if we ask Brooke really nicely, we could probably have him around whenever we want," Kitty said, groaning through her own efforts.

"You'll have to ask really fucking nicely," I said, reaching up to squeeze Riley's tits as she rode me. "Brooke's kinda addicted to my cock."

"I can see why!" Riley moaned, giggling and looking down at me hungrily. "It might not be easy to go around with other guys after this!"

Kitty looked at her friend, groaning through her fingering. "Oh, I need to have some of this soon."

"You will, you will, once I'm done... once I've drained Ryan's balls..." Riley said, looking from Kitty to me, smiling broadly and bouncing playfully. "You like that? You like that thought? You like the idea of filling me full of all of your cum? 'cause I heard you cum like a geyser, and I want it aaaaaaaaaaaaalllll!!!"