Senior Year Memories Ch. 40

"Oh, awesome," I said, moaning as she inhaled my cock to the root.

Looking at her like this, bent over on the bed, her tits crushed against my thigh as she energetically blew me, I couldn't help but notice how well her ass stuck out. It looked so round, so perfect... I couldn't help myself. I reached for her ass, at first squeezing it in appreciation for how she blew me, but then trailing a finger between her cheeks.

Remembering how she responded when I tongued her ass, I ran the tip of my middle finger in circles around her asshole. When she only answered me by blowing me harder, I did this with a little more pressure, my finger finally breaking through and pushing a couple knuckles up her asshole. Katie squealed around my cock and only blew me harder, so I figured this was a good idea. I fingerfucked her ass in time with her bobs, only seeming to drive her wilder and wilder with every passing moment. In no time at all, she had my cock restored to full strength, and with the lust between us having already built to a crescendo, there was only one way this was ending.

I grabbed her by the hair, pulling her head off my cock. My voice was low and hungry as I said, "I need to fuck you again. Now."

"Yes, please!" Katie exclaimed, as perky and cute as ever as she twisted around, landing on her back with her head on her pillow and her legs parted widely for me.

I climbed over Katie, lining my cock up with her soaking wet pussy, and slid home inside of her once more. It was easier going this time, and Katie's satisfied hiss greeted me as she wrapped her legs around my ass and made sure I was nice and deep. In no time at all, I was fucking her hard again, stealing kisses and squeezing her big, beautiful tits whenever the opportunity suited me.

"A girl could... fuck... get used to this kind of treatment," Katie sighed pleasantly, moaning and grunting in between my thrusts as I gave it to her.

"So could a guy," I admitted as I bottomed out in her once again, unable to deny our chemistry.

"Does this mean more game nights? Because if this means more game nights, I'd very, *very* much be down for more game nights," Katie squealed, locking her legs behind me and sticking out her tongue lustily again.

I leaned down, sucking her tongue and claiming her mouth as my own. The feel of her body against mine, so hot and soft, perfectly conforming to me while still demanding her own needs... fuck, Katie was perfect. I never would've guessed this, but as always, I never should have underestimated the women of Regan Hills.

Especially when Katie brought out her next proposal.

"So, what we've been doing, what you've said... and done... fuck, keep going there, right there, oh yeeeeeeeeeeeeaaaaaah..." she moaned, before trying to reclaim her words. "What was I saying? I was thinking... right, yes! I was thinking about what you said earlier!"

"We said a lot of things earlier," I grunted, enjoying this rhythmic pace as I fucked her appropriately hard. "Did a lot of things... you'll need to be more specific."

"It's hard to be specific when you're fucking me like that!" Katie squealed, giggling as I didn't change my pace.

"You want me to stop?" I asked.

"NO!" she exclaimed, locking her heels behind me. "I just want you to listen... and for me to be able to talk, oh is that last part hard... not as hard as you are, but really, really difficult! Conversing while getting railed, it's a challenge!"

I grinned. "Yeah, I've seen a lot of girls have that problem. Just try to get it all out, you'll be fine..."

Katie bit her lower lip, then nodded. "What you said earlier... and when you were playing with me while I was blowing you... I want you to fuck my ass! I want you to be the first to fuck my ass!"

While there was nothing I would've wanted more, that it was her first time caused me some pause. Not actual pause, mind you, because I was still very much enjoying fucking her tight, quivering cunt, but enough mental pause that I nearly did slow. A first time with any new sex act was always a tricky proposition, and I didn't want to mess anything up.

"Are you sure?" I asked.

Katie groaned. "As sure as I've ever been about anything... I watch a lot of porn, I've seen a lot of cock up a lot of asses, and it always gets me so horny watching it... and your cock, god... I need to know what it feels like, and I want your cock in me! I think... no, fuck it, I know I wanna try it!"

Well, the girl knew what she wanted, I had to give her that.

Grunting, I slowed my pace. "You wouldn't happen to have any lube in here, would you?"

"Sorry, never thought I needed it, but I guess I gotta fix that," Katie said. "Do you have some?"

I looked down at my pants on the floor. "Always keep a little emergency lube tube with me. Never know when it might come in handy."

"You plan ahead! Love it!" she exclaimed, unlocking her legs from behind my hips, letting me pull out and climb off of her.

Though I was in quite a bit of need, feeling rather acutely the absence of her pussy embracing my cock, knowing what I was soon to do, I didn't worry for long. I retrieved my emergency bottle of lube from my pants, returning to the bed to see her sitting up and smiling at me. It was a smile of nervous excitement and anticipation, but distinctly eager.

"If this really is your first time, I think we should start by fingering your ass a little first, getting you relaxed and really into it before we begin..." I said, sitting beside her. "You could always get on your hands and knees, or face down, ass up, whatever you prefer-"

Before I could give another option, she settled down on my lap all at once, turned to the side and settling her ass against my right hand. "Or like this?"

"Yes, this can work," I said, laughing from surprise at her sudden appearance on my lap.

I squeezed a little lube onto my fingers, then set the bottle aside. "You ready?"

Taking a deep breath, Katie nodded. "Yes. I think so."

"Let's give it a try, then... and let me know if it's too much for you; if this isn't working for you, we don't need to go any further," I said.

"I told you, I've had my ass fingered a little before. *You* just had a finger up my ass," she said, nuzzling up to my chest. "But thank you for that. Consent really kicks ass."

"Oh, I know it," I said, running my hand down her ass.

I squeezed each of her cheeks, gently massaging them, helping her relax as she squirmed appreciatively in my lap. When she seemed suitably settled in, I ran my lubed-up fingers between her cheeks, spreading the lube around and running my fingertips in small circles around her hole.

Katie giggled at the attention, snuggling up next to me more. One of her small hands reached out and began stroking my cock, which didn't make things necessarily easier for me, but, certainly didn't hurt either.

As I could tell she was loosened up, I pressed one finger against her asshole. It slid in easily, as it had when she was blowing me, and I fucked it in and out of her gently. Katie moaned, groaning softly as she rocked her hips against my finger. Well, if she liked that...

I slid a second finger in. The fit was definitely tighter, and Katie was squirming even more in my lap, but she looked up at me with those big, dark eyes, her lips pursed with need and effort, and I knew that she wanted more. Slowly, I twisted my fingers around in her, thrusting them in and out of her tight little hole, trying to find her most sensitive angles and a pace that would drive her absolutely wild. As soon as she was quivering and rocking her hips against me, trying to take in more and more as she continued eying me with that strained determination, I knew she was ready.

I pressed a third finger into her, joining with the others as I twisted, slowly fingering in and out of her ass until all three fingers were buried deep inside of her.

"Oh god... oh my god..." Katie murmured, reaching between her legs to finger herself as she nuzzled her head against my neck. I could feel her juices dripping down from her pussy onto my leg, a steady, slow flow that accompanied well how ragged her breathing had gotten.

"You like that?" I asked. "You like having your ass nice and full?"

Silently, Katie nodded, craning her neck so she could kiss me while jerking my cock even harder. Her small hand felt amazing, spreading my precum up and down my shaft, but I knew something that would feel even better.

"You ready?" I asked.

"Uh-huh," she confirmed, grinning.

"Then you're probably going to want to get back on your hands and knees..." I said, returning her grin darkly.

Without much need for encouragement, Katie pulled herself off my fingers and got up onto her hands and knees. I took this moment to spread some more lube on my cock to make sure I was well-covered. I'd already lubed up her ass pretty decently with my fingers, but when it came to anal, you could never use too much lube as far as I was concerned.

I got up on my knees behind her, and took a moment to really absorb her ass. I eyed it hungrily, using this moment to fully understand the perfection of Katie's perfectly round, soft, and amazingly sexy ass. This would be the last time it would ever be unfucked, and it had to be appreciated, even if only briefly. I ran my hands over her cheeks, squeezing them, making her shiver in anticipation.

"Oh, this is crazy, this is so fucking crazy," Katie said, moaning softly as I ran the head of my cock between her ass cheeks. "I shouldn't be doing this, this is just one of those crazy things they do in porn, this isn't something you do... ever... but I'm here... oh god... I want it... it scares me, not like a lot, but a little, but I want it, I want it so bad... is that crazy? It's crazy, right?"

"It's a good kind of crazy," I said, teasing my cockhead against her hole, running it in tight little circles that had her moaning again. "You're sure you want this?"

"Completely," she replied, nodding and looking back at me. She let out a nervous breath, then nodded again. "Almost completely. Completely enough. It doesn't have to be perfect, this is going to be a little crazy until I do it, but I want to do it, so... let's do it. Slow, for starters?"

"Of course," I replied, gently caressing her ass cheeks again as I lined my cock up for entry. "Be ready, though... I'm about to start pushing."

Gritting her teeth, Katie said, "Let's do this."

"Alright," I said, gently thrusting forward.

Katie moaned as my cock pressed against her asshole, a sound of lust, determination, and maybe a little pain. Her hole was unyielding in the moment, even with this preparation, allowing for only a token bit of give as I pressed against her.

"Come on, you can do this... you've got this... you've watched a lot of porn, girls take dick up the butt all the time, sometimes really, really big dicks, this is easy... easy and awesome... just like the fingers, come on, fucking do it, do it..." Katie murmured to herself through gritted teeth as I continued to press forward.

The lube was doing its job, and my short, gentle thrusts were opening up her ass a little at a time, but even with her encouragement and desire, I was still making little progress.

"Okay, okay, maybe it's not that easy... maybe they have other tricks in porn... like experience, and lube, and smaller dicks than this, but I can do it, I've done a lot of weird things, a lot of hard things, a lot of things I never thought I could do, a lot of people never thought I could do, I can do this... I can take this... I've got a kickass ass! I can do this!" Katie grunted, pushing back against me.

At first, it seemed like the progress I was making was small. Then, as things often happen in life, it all happened very, very quickly.

With one thrust, I pushed against what felt like a wall.

With the next thrust, suddenly her asshole was welcoming me in. One of the tightest holes I'd ever fucked was suddenly squeezing my cockhead, plus an additional inch or two of my cock.

There was a brief silence, one so profound and utter you could have heard a pin drop from a mile away.

Then Katie screamed.

"HOLY FUCK, HOLY FUCK, HOLY FUCK!" she cried out, looking back to see the truth that I had indeed pushed some of my cock into her asshole. "HOLY FUCK, YOU'RE IN MY ASS! I DID IT! WE DID IT! I... QAPLA'!"

Katie laughed a high, manic laugh as she wiggled her ass, pressing herself against me and swallowing another couple inches of my cock. Her reaction was so unexpected, I was taken by a brief stab of worry.

"Are you alright?" I asked, holding onto her hips and keeping myself from going forward. "I didn't hurt you? And... what's qapla'?"

Giggling some more, Katie smiled back at me sweetly. "It's Klingon 101, I'll teach you some sometime if we keep making this a regular thing, which I really, really hope you want to do because this is amazing."

"So... you're alright?" I asked, still holding my current position.

"I'm better than alright! A great mind once said, 'If you put your mind to it, you can accomplish anything!' Well, I put my mind to this, and I accomplished; your dick is up my ass, and it feels soooooo goooooooood! I mean, it hurts some too, but, a good hurt, I think. Wait... yeah... definitely a good hurt. Probably. Definitely probably. Only way to know for sure, though, is to fill me up, so if you get a chance to push more of that monster up my butt, I'd really quite appreciate it! I don't know if it'll fit, but why don't we find out together?" Katie replied, laughing and smiling like a giddy fool.

I'd seen some girls get pretty fuck drunk after a couple good orgasms before, but this definitely felt new. The sheer act of accomplishment had her high and silly, and if it was something she seemed to be enjoying this much... I no longer worried for her. Especially because, well, her ass was an absolute treat, and I really wanted to see what would happen once we really got going.

And so, with her dirty words and sweet smile pushing me along, I continued to feed my cock into Katie's tight, clutching ass. It wasn't easy, but with such a tight, hot hole on a singularly hot and luscious human being, there was no way I wasn't going to keep doing this. I kept pushing forward, an inch at a time, each inch spreading greater heights of pleasure through my cock to the rest of my body. I could have stretched this out to hours, days, weeks and I doubted I'd ever be fully satisfied with the perfection of Katie's ass.

Yet, I wasn't disappointed when my hips touched her ass and my balls brushed against her pussy, for this felt like perfection.

"Hoooooooooooooly hell..." Katie moaned, trying to crane her neck to see just what was going on and finding that thoroughly inadequate. "I need to see this... I can't believe it, and seeing is believing, right?"

Looking around frantically, she grabbed my phone from where I'd set it on the bedside table and passed it to me.

"Show me..." she groaned, looking back at me with a face of pure desire.

Well, I couldn't say no to that. I pulled back a couple inches to give the best contrast and snapped a picture, then showed her the results.

"Oh god... oh wow..." Katie laughed, squeezing my cock with her ass as she wiggled against me. "That's almost a foot of dick right up my ass... so that's what that looks like... wow... I never thought, you know, that this was something I'd do... I'd watch it, sure, but this isn't... oh wow..."

I set my phone back on the bedside table. Katie kept giggling, almost completely lost as she reached down between her legs.

"Holy crap... my clit, it's like, unbelievably sensitive right now... it all feels so good..." she moaned, her breathing increasing as she touched herself. "Everything's so sensitive, it feels like if I just... OH!"

I don't know what she touched that set herself off, but Katie's body soon bucked with a hard orgasm. It seemed to take her by such surprise that she barely even uttered a sound, but the sudden, explosive gushing of her pussy squirting against my thighs was indicative enough that it was a pretty hard fucking cum. Her ass squeezed my cock so hard it nearly pushed me out, but I held onto her hips for stability, making sure she stayed right where she wanted to, and that I would stay buried fully in her ass.

The moans only came as she seemed near collapse, her arm giving out as she landed face first on her bed, a shivering, quivering mess.

"Holy... holy something, that was... woooooooooooooowwwwww..." Katie moaned. "I can't... I can't stop my legs shaking... I can't... how is this possible?"

I leaned down over her, bracing myself with one hand while reaching beneath her with the other, squeezing one of her tits tenderly.

"It's pretty fucking cool, isn't it?" I asked, kissing the back of her neck.

"Yeah. Yeah it's pretty fucking cool. It's pretty damn fucking cool," Katie replied through low, belly laughs. "Holy fuuuuuuuuuuuck... I don't think I've ever cum that hard, that was... that's fucking crazy."

I chuckled in her ear before kissing the back of her neck again. "Anal can get pretty crazy. You want more?"

Katie turned her head to face me, kissing me fiercely. "You better give me more... I just had my first taste... I need more than just a taste."

"Just thought I'd ask," I replied, getting back up into a kneeling position behind her.

Katie's legs were still shaking, and she still seemed a little too weak to hold herself up. Nevertheless, the lady needed her ass fucked, and I was in need of one last, good, hard cum.

So, squeezing her ass with both hands one last time, I held onto her hips once more, and I started fucking her ass properly.

Her moans started out loud, but seemingly only got louder as I began to fuck in and out of her ass. She felt... god, did she feel incredibly. Her ass was so damn tight, and so fucking hot, gripping and squeezing me as I thrust in and out of her. I felt fortunate that I had already cum a couple times, as I would not have lasted for even a minute like this with a full load. It was difficult enough as it was to fuck her without completely losing it, but there I was, grunting and groaning as I fucked her no longer virgin ass at a modest pace.

Soon, Katie began to regain some of her strength, pushing herself back up onto her hands and knees and letting her better look at me with those big, innocent-looking (but hardly innocent) eyes.

"God, your cock's so amazing in my ass..." she moaned, sticking out her tongue playfully and thrusting back against me. "Hurts so good... fuck... how do you like my ass? A lot of guys like looking at my butt, and I'm sure you did too... how do you like fucking it? How do you like forcing that beast up my sweet and pure little ass?"

"Still sweet," I grunted, looking down at her with a devilish grin. "But I doubt you were ever that pure."

Katie winked at me. "Guilty as charged. But you like me that way, don't you?"

"What can I say? You got me," I laughed, fucking into her slightly harder.

She closed her eyes tightly at this, gritting her teeth and groaning deeply. "Fuuuuuuuuuuck... okay, alright, alright, fuck, oh god, fuck, this is something I need to remember... something I gotta do more often... because this is really fucking great, god, I need my ass filled all the time! I need to be fucked like this all the fucking time! I need this... god... I need this, fuck me, Ryan, fuck me harder, fuck my ass, yes, yes, yes, keep going, keep going, you're gonna make me cum again... you're gonna make me cum again..."

I reached down, grabbing Katie and pulling her up so she was kneeling in front of me. I wrapped my arms around her chest, supporting her and squeezing her tits as I fucked up into her. Katie moaned and hissed, turning her head to look at me and forcing me into a kiss as she reached behind to hold onto me with one hand, while fingering herself with the other.