Senior Year Memories Ch. 44

"I'm honored," I joked, kissing her again.

I was honored, though. I had come to understand that Chloe had a way of communicating her thoughts and feelings that was a bit different from most of the girls I knew, and between her words and the slightest changes in her facial expressions, I knew that she meant this as the highest of praise.

Well, that, combined with her moans, and the way her body responded to mine, and the way that she had unconsciously locked her arms and legs around me to hold on for dear life while I fucked her hard. Her pussy massaged my cock with great strength, and yet it still felt absolutely perfect. This may have been her first time, but she genuinely seemed like she was made for this, and I could only imagine one hell of an exciting, horny future for her.

Looking down at her, I could only feel a certain, distinct joy being shared between the two of us. It wasn't long ago that I was a virgin myself in much the same position, one who didn't know what he was facing as he was unleashed upon this year. In that way, I actually rather envied Chloe. In spite of her social awkwardness, she had a kind of confidence that I was almost jealous of, and if she put only a fraction of that confidence into her sex life...

Fuck, this girl was meant for great things.

In the short term, however, she was also an amazing fuck, and one who was pushing me closer to the edge a lot faster than I would have expected of a girl of her level of inexperience.

Looking up at me, Chloe fought through her moans to say, "By the increasing look of strain on your face, the tension in your body, and the slight swelling I'm feeling in your cock which... fuck... feels absolutely amazing... I'd say you were close to your orgasm. Did I... ohwow... did I read that right?"

Grunting as I kept driving into her, I gave her a silent nod.

Chloe smirked at having figured that out. "That's... wonderful... and I'm sure you're... fuck... I'm sure you're wondering... yes, yes, keep going, I'm close... so close... I'm sure wondering where you can cum. Well, please consider cumming inside of me, I think that would be... well, you saw my checklist, so you probably saw that I had a creampie on it, and I would like that to be you... keep going, please, Ryan, please cum inside of me, I want... I *need* to know... I need to know what it feels like, what it's like to... yes, keep going, you're going to... you'll make me... OHHHHHH FUUUUUUUUUUUCK!!!"

Tightening her arms and legs around me, Chloe came again, hard and loud and squeezing me so tightly I thought I might never let go. With her encouragement, I didn't stop fucking into her, not until I couldn't hold it back any longer and came inside her, hard. I grunted, loudly, burying deep and releasing an explosive orgasm. It was draining, flooding me with a euphoria as I filled her no longer virgin cunt with my cum, a strange sensation that seemed to keep me going harder, giving her what felt like a slightly bigger orgasm than most.

We came down in much the same time with each other, moaning and breathing heavily, sharing soft, deep kisses before we both threatened to collapse.

Kissing her again, I pulled out and rolled onto my back next to her, trying to catch my breath while I stared up at the ceiling.

Catching her own breath and looking thoroughly well-fucked, her hair a mess and her skin flushed, Chloe briefly toyed with her pussy, rubbing the massive river of my cum that leaked out and considering it before she put her fingers to her lips and sucked it off. Her eyes lit up upon tasting it, and soon she reached down for another dollop of our mixed juices, sucking it off lustily.

It was an unbelievably hot sight, though the smile that followed when she turned onto her side to better look at me might have even beaten that.

"So, that was sex?" Chloe asked.

I sighed pleasantly. "I mean, there's a lot of different kinds of sex, but, yeah, that was a pretty popular one. Verdict?"

She bit her lip thoughtfully, before nodding and smiling brightly. "I like it. I feel like I wasn't at my best, but this strikes me as one of those situations where more practice will only improve my skill level."

"Yeah, I've found that as well. I haven't been with many virgins, but the ones I have, yeah, they all got a lot better with time and practice. A *lot* better," I said, thinking fondly of Sophie and Jennifer.

"I would bet on it," Chloe said, rolling on her opposite side so she could reach a nightstand and open its drawer, pulling out a box of candy. "Would you like some Whoppers? I'm always in the mood for chocolate after I have an orgasm, and after what I just had... I believe I'm going to need a fair bit of it."

"Sure," I said, holding out a hand. "But, your post-sex candy of choice is Whoppers?"

She'd held the box to my hand, but quickly drew it back. "If you don't want any, I'm happy to keep your ration for myself."

I laughed. "Give it here."

Chloe smirked, enjoying the power she held in the moment, before tipping some Whoppers into my hand. I popped a malted milk ball in my mouth and crunched down on it, finding it indeed to be a good post-sex snack.

Chewing on one of her own, she set the box aside, lay on her back and continued, "This is... an interesting sensation, to be honest. Popular fiction would have had me believing that I would feel completely different, like I'm a different person all because I had sex. So far, I can't say that I feel all that different on the whole... more tired, and certainly feeling a greater kind of physical pleasure than I would have been capable of on my own, sans toys, but the world still looks the same, these candies still taste the same... nothing looks or feels that different, but I *know* deep down that something has changed. It's... unique. Powerful, I think. I'm not sure I know what I'm going to do with that power just yet, but I think I rather like it."

There was something about her, an extra glow, a slightly new flare in her confidence that I had to admit was a good look on her. I didn't know if I'd created a monster in that moment, but whatever she was now, I knew I liked it.

Chloe and I lay there like that for a moment, munching on candies and taking in her new glow, before I thought to say, "So, would you still be up for an interview?"

She raised an eyebrow. "Like this?"

I laughed. "Bizarrely, I do a lot of my best interviews in the nude, apparently. More reason I'm happy that the vast majority of my interviews this year have been sexy ladies."

"Yes, I could certainly see the appeal in that," Chloe replied, finishing the last of the candies she had in her hand. "And while I would certainly be amenable to sharing my story in theatre and why I think I would be the ideal actress to play Audrey in the spring musical, I'm not tired, yet. If you think my sex drive has waned simply because you helped me climax a few times, I believe you have deeply underestimated me."

Looking at the beautiful, naked nerd lying beside me, I said, "Oh, I would never underestimate you, Chloe. You're... you're something else."

"If that's not just a line, that's quite sweet," she replied, smiling.

"It's not a line," I said, smiling back. "It's... I guess in a lot of ways, you remind me of me, but the me I wish I could have been when I discovered my talent for sex. I was always so damn anxious and beating myself up, and you... you seem every bit as awkward as I was, but you're also, like, a million times more confident in your own way. I'm actually kind of jealous of you, honestly. Not just who you are now, but also of the person you potentially could be. I've had some crazy sex adventures this year, but something tells me that by the time you really get your rhythm, you'll make me look like a fucking amateur."

"I doubt you'll ever look like an amateur, especially at sex," Chloe said, grabbing another dollop of our mutual juices and sucking it down. "And I still have so far to go."

"Well, I've got the time," I said, smiling. "What about you? What's the next item on your checklist you'd like to check off?"

Chloe licked her lips, but said nothing, looking thoroughly thoughtful for a moment as she stared up at the ceiling silently.

I'd begun to think I might have said something wrong, crossed some unknown line, when she finally replied, "Honestly... I'm not sure. I'm at a state where a lot of options are sounding both feasible *and* appealing, and I find it somewhat overwhelming. This is not something I'm used to. Normally I am so focused and can follow a linear set of steps that I know will absolutely suit me, but quality sex seems to have destroyed any chance I have at thinking straight. I know I should blame you, perhaps even feel upset by your ability to disorder my mind, but the way I'm feeling right now, I don't think my body could contain a single ill feeling. At least towards you."

Chloe rolled onto her side to face me again, looking absolutely stunning, as she nervously smiled. "So, as I am partially crippled by my own indecision, I must ask: you've seen my checklist and know what I wish to accomplish, and as you look at me right now, I must ask, what would *you* choose to do with me if given the opportunity?"

I thought about this. "And you're up for *everything* on that list?"

"Everything that you happen to be capable of... I don't believe 'savage and messy scissoring with another girl' would be a talent you could ever provide for me," Chloe explained, smirking slightly.

"Fair..." I said, looking her over and letting my imagination run wild.

As I noted earlier, her list was impressively comprehensive, and while I doubted I could help her make a huge dent in everything she wished to accomplish this year, I was happy to help see her through some of the basics. This led to an idea forming, and even if it might test some of her limits, I got the impression that Chloe would be up for the challenge.

"Well, first thing's first," I said, motioning down to my mostly deflated cock. "If you want me to do anything with this, I'm going to have to be hard again, and while being in the presence of a beautiful girl with talent like yours has a way of doing that on its own eventually, you could always help me expedite the process."

Chloe looked down at my cock, then smiled. "I can, can I?"

I nodded. "There's a lot of different things you can try to get me hard, of course, but a good, old-fashioned blowjob is pretty reliable, and since you've yet to check that off your list... well, I feel like we could do something with that. For starters."

Looking at me intently, she quickly rolled until she was partly on top of me, kissing me deeply before she started to crawl down my body. "For starters?"

Chloe was kissing her way down with a fair bit of force, which I had to admit felt pretty good, even if she might have been a little overenthusiastic on my nipple. I cried out with this attention, first from surprise, then from pleasure as she combined her toying with my nipple with stroking my cock. Fuck, you could not say that this girl lacked enthusiasm.

Finally realizing she'd asked me a question as she trailed kisses down my body, I explained, "I mean, I'd be happy to fill your mouth with cum and watch you swallow every drop, but I was thinking of something else, once you got me hard. Something a little more... vigorous."

Chloe had by now crawled between my legs, her face now level with my half-hard cock. She took it in hand, marveling at it, running her fingers up and down and playfully slapping my length across the side of her face, an action that caused her no small amount of laughter.

"More vigorous than what we just got up to?" she asked.

"Uh huh..." I said, groaning as she brushed her lips lightly over my cockhead. "Fucking a girl in the ass tends to get a *lot* more vigorous than that."

Chloe's eyes widened, but she didn't stop exploring my cock with her hands, or lightly brushing the head over her lips. "You're serious?"

My cock was getting harder by the moment, enough that I might not have even needed a blowjob at the rate she was going. "Dead serious. You've got a nice little ass, and I wouldn't mind being the first to fuck it. If that's not something you want, I of course can-"

"NO!" she practically shouted, before calming herself. "No, I would greatly enjoy you fucking my ass. I was just uncertain to the degree of your enthusiasm to do that; I've heard that there are many guys out there who aren't into that particular act."

I shrugged. "I mean, I hear they do exist, but I don't get it; anal's the fucking best. I'm all for it."

"As am I," Chloe replied. "In theory. I'd like to know with certainty to see whether my speculation on its enjoyability is justified."

"Well, that's what I'm here for," I said, reaching down to lightly brush her cheek as she continued to tease my cockhead with her lips. "Get me nice and hard enough and I'll happily show you some of what I know."

"Some of?" she asked, raising an eyebrow. "I don't want *some*. I want it *all*."

I chuckled. "You say that now, but wait until you've actually had my cock up your ass. Then you'll be sure."

"Fair," Chloe replied. "Can I try sucking your cock now?"

"Go for it, just-"

"My teeth shan't even slightly graze your cock, you can relax," she said, cutting off my first piece of advice before I could give it. "I have read a tutorial or two."

This wasn't exactly the kind of reassurance I think she meant it as, but I was too horny at this point to care very much. "Then, by all means, go for it. Suck my cock..."

Grinning up at me, Chloe then pursed her lips, pressing them against my cockhead and sucking, lightly flicking her tongue so the tip grazed the slit of my cockhead. I hissed as a lightning bolt of pleasure shot through my body, but before I could really do anything about it, she pressed forward, opening wide and sucking my cockhead into her mouth, swirling her tongue over the head until she couldn't reach anymore, at which point she began to suck me down.

By the slight look of distress in her eyes, I could see that my cock was a lot bigger than she had anticipated, and no amount of enthusiasm could overcome that. Nevertheless, Chloe was also a determined girl, sucking and slurping and pushing forward, not stopping until my cock first hit the back of her mouth, and then until she invited me into her throat.

Soon enough, she had every last inch buried as far as it would go, her nose pressing against my groin as she held my cock in there for one triumphant moment.

I lightly stroked the side of her face. "Well, we can probably check off both 'blowjob' and 'deepthroating' from your list. You can probably tell how hard I am now, but if you want to keep going, hey, I'm not going to object."

Quickly, Chloe pulled off of my cock, coughing and wiping strands of precum and saliva off the corners of her mouth. "Are you kidding?"

Playfully, she leaned down, sucking on my balls briefly and causing me to moan deeply, before she went back to kiss my cockhead. "I've been looking forward to this day for a *very* long time; I'm going to make the most of this blowjob. Sans swallowing your cum, as we discussed, since I would greatly enjoy having you fuck my ass."

I grinned. "Obviously."

Chloe leaned in again, sucking half my cock into her mouth and bobbing her head as she gave me one hell of a blowjob. It was clear that she had spent most of her time practicing on a toy, and I needed to guide her and correct her a couple times to give her a better idea of a pace and what was comfortable for me, but as ever, Chloe was a quick study, and she was soon giving me a pretty amazing blowjob for what was clearly her first on a real guy. I ran my fingers through her hair, thrusting and fucking up into her mouth, moaning and enjoying the hell out of the experience.

Fuck, at the rate she was going, she probably could have gotten me to fill her mouth with cum without a lot of effort. She truly was something of a prodigy, and while I would have liked to reward her with cum, that was something best left for another time.

Gently taking a handful of her hair, I pulled her mouth off my cock.

"Get up here..." I directed, lowering my voice to a command.

Nodding, Chloe climbed over me until we were face to face, and I pulled her in for a kiss, the two of us making out and groping each other with a growing heat for a few moments before I reached down, grabbing my cock and guiding it into her pussy.

Chloe moaned, but quickly took to riding me, moaning and bouncing her hips up and down on my cock as she quickly fucked me. Fuck, I really liked fucking this girl. Watching her lose control as she got into the act, moaning and writhing and stripping herself of any semblance of the anxious overachiever she was at school, it was a beautiful sight.

But, this was also not how I was meant to cum, enjoyable though that would have been. This was just to get a little additional lubrication, though some extra certainly wouldn't hurt.

"You said you have lube?" I grunted.

"Uh huh..." Chloe confirmed, cocking her head to the side. "I keep a bottle under the Whoppers."

"Good to know," I said, pulling her off of me and setting her beside me on the bed, face down. "Stay there."

"I will... but don't leave me for long; you got me so unbelievably aroused, it feels like anything could set me off..." she threatened, her voice deliciously strong as she turned her head to look at me.

Seeing Chloe lying face down, reaching her hands between her legs to finger herself, was certainly an impressive sight. She rocked her hips ever so slightly, flexing her tight ass in what was an admittedly nice show.

Quickly, I searched through the nightstand until I pulled out her bottle of KY, before crawling behind her on the bed. I grabbed her by the hips, pulling her up slightly onto her knees, but only slightly, needing just a bit of a raise so I could get a better look at her tight ass in preparation. Teasingly, she flexed her cheeks, giving me a nice little view of her tight, pink, mostly virgin asshole that she wanted me to properly destroy.

I licked my lips, and decided on a brief detour, albeit one that was on her list.

I leaned in, pressing my face between her ass cheeks and sticking out my tongue, running it in swift, firm circles over her tight asshole.

"OH!" Chloe exclaimed, her entire body rocking with surprise. "Oh, wow! I wasn't expecting... mmmmm... that's good... oh, wow, keep going, keep going like that, please... I actually wasn't expecting my ass getting rimmed to feel this good... yes, yes, please... oh, that's good, yes, keep licking my ass, keep licking, and sucking like that, yes, oooooh, that's good, that's so good, please keep going, please!"

She gripped the sheets and buried her head into a pillow, crying out in pleasure as I continued to tongue her ass. Truthfully, I did this because her ass looked fucking delicious (and it was), but I also wanted to see how sensitive her ass was. It seemed like the answer was "quite" in this case, which made me rather optimistic for the next steps.

I teased her hole, sticking my tongue out and pressing against her tightness, but found it to have a considerable amount of resistance. Considering her experience, this wasn't exactly a surprise, and if I wanted to tongue-fuck her ass, I probably could've done it with enough determination.

But I got the impression that Chloe wanted something a little larger up her ass.

I pushed myself back up onto my knees behind her, reaching for the bottle of lube. "Get up on your hands and knees."

"Yes," Chloe replied, her voice slightly soft and shaky. She tossed her hair over one shoulder, then looked back at me, her eyes wide and hopeful as she watched me lube up my cock, before squeezing some more between her cheeks.