Senior Year Memories Ch. 44

With a single, hard jerk beneath me, Chloe came hard. She quaked and shook uncontrollably, her eyes rolling back as her moans took on a low, wailing sound, trailing on and on as I continued to finger her. Her pussy positively gushed on my hand, the room filling with the smell of her arousal as she continued to rock her hips against me. I couldn't help but feel a great sense of pride at getting her to lose it quite like this, and looked forward to what else I'd be able to get out of Chloe.

I slowed down my fingering, letting her come down and catch her breath while still enjoying my position. It took a moment, as that first orgasm you've had with a partner often does, but once I was content that she'd mostly come down I pulled my fingers from her pussy and gave her nipple one last playful nibble.

Chloe yelped, then tugged at my shoulders, pulling me up so I could better kiss her. She was still far from an expert kisser, but her enthusiasm more than made up for that as we made out. Her energy returned more and more the longer we kissed, and soon she was looking up at me with a bright smile.

"That was... very satisfactory," she said, trying and failing to look utterly noncommittal about her praise.

I kissed her again. "That orgasm sure seemed a lot more than satisfactory."

"True," Chloe agreed. "But as it is merely a prelude to what I was hoping this day would include, I can only assume it will be merely satisfactory compared to what will come later."

It seemed that even in a cum-drunk haze, Chloe had a hard time turning off her analytical side. Considering our positions, that wasn't something I wanted to take away from her, but I was up for a little light teasing.

"You seem to have a high estimation of my skills," I said, kissing her playfully.

"A well-earned one, but one that you no doubt are already well aware of and are merely feigning ignorance of in an attempt to produce secondhand praise, get me to name names and further inflate your modest, yet thoroughly existent, ego," Chloe replied, smirking slightly.

Okay, I'd give her that. Mentally, of course, since admitting it out loud would have changed the tone of the moment, so rather than do that I simply leaned in and kissed her further, massaging her breast. Soon I felt one of Chloe's deft hands reaching down, taking in the size of my cock through my underwear, probing and wrapping her fingers around it.

"I see you're trying to distract me in an effort to avoid discussing your ego with me," she continued, amused.

"Is it working?" I replied, kissing her neck.

Chloe moaned, continuing to massage my erection. "Rather well, actually. But if you truly wished to keep me distracted, I could offer some better suggestions that I think you'd find most pleasurable."

I raised an eyebrow. "Could you?"

"I could, and I will," she shot back, sounding more confident. "First... I would like you to take off your underwear so I could see this cock I've heard so much about. And then... then I want it inside of me. I really, *really* want to have sex with you, Ryan..."

Chloe's voice was at once confident and pleading, yet certain enough that I didn't need a whole lot more confirmation from her.

I climbed off of her and sat on the bed, looking down at her nude form, before she sat up with me. Her eyes were trained on the bulge in my underwear, widening as I began to tug at the elastic waistband.

"Are you sure that's what you want first? I mean, a lot of girls really like my oral skills, and they certainly never hurt whenever we're warming up for some fun," I explained, tugging my underwear down under my ass.

I still wasn't exposed to her yet, but Chloe's eyes didn't waver from staring at my cock for even a second as she replied, "While my sources have made me well aware of your talented lips and tongue, I'm afraid my own impatience is actually overriding the tempting nature of your offer. While I'll no doubt want to experience that at a later time to see the true depths of pleasure you can take me to, to be blunt, I need to get fucked, and I need to get fucked soon."

"Fair enough," I replied, pulling my underwear down my legs. "I just wanted to be absolutely sure before we went any further..."

I could have said more, but when her eyes widened and mouth dropped open slightly, I knew that Chloe was in a state where she probably couldn't have heard a word I said even if she wanted to. When my thick, ten-inch erection became visible to her eyes with its flared head dripping precum, you'd have thought that this analytical girl's animal instincts had completely taken hold of her.

Gooseflesh broke out on her skin, and she couldn't help but slide closer to me, reaching out and grabbing my cockhead with one of her dainty hands. Though she couldn't wrap her hand all the way around the head, she seemed to fairly enjoy experimenting with it, running her palm over the tip as she spread the precum around.

I hissed in pleasure, rather enjoying her exploration.

For her part, Chloe could only say, "That is a thoroughly efficient natural lubrication."

I chuckled, groaning softly as I unconsciously thrust against her hand. "I've yet to hear any complaints."

"I would suspect not," Chloe said, taking her hand away and experimentally licking some of my precum off of it. "Interesting... I think I'll greatly enjoy sucking your cock later, but for now... what would be the best way to go about doing this, would you say?"

"It's your virginity, your call," I replied.

After a pause, she said, "I've spent a lot of time considering the best options. I've always thought it would be good to be on top so I could measure things at my own pace... but, as I am with someone with your experience, it might help if you were to be in a dominant position that would allow you to better see me through some of the more awkward, early steps. Decisions, decisions..."

Chloe thought about this for a moment longer, then nodded decisively, "Yes, I'd like to be on top for my first time."

I nodded, lying out on the bed next to her and propping my head up with a pillow. The gorgeous, nervous drama nerd next to me smiled shakily, looking down at my naked body and my thick, throbbing cock, with equal parts anticipation and trepidation as she took me in.

"Alright," Chloe said, getting up onto her hands and knees and crawling over me, straddling my legs, "This is happening."

She climbed over me with a slow eagerness until her pussy touched the base of my cock, causing both of us to involuntarily groan. The heat of her pussy against my shaft was truly impressive, while her moisture ran freely over my cock. With a bit of uncertainty, Chloe leaned forward, placing her hands on my chest for balance and rocking her hips, gliding her pussy lips up and down the underside of my cock as she got accustomed to being so close to me.

Biting her lip, Chloe looked down at me and offered a weak, yet thoroughly pleasant, smile as she continued to grind her pussy against me. "You feel good."

I smiled back, running my fingertips lightly up her sides in a way that made her shiver. "Not as good as you feel."

"That's a matter of interpretation," she replied. "And one I doubt we could come to a satisfactory compromise on given our inherent biases. Regardless of such qualitative debates, I do wish to thank you for seeing me through this, and for going this far with me. I have had opportunities prior to this to have sex, but have turned them down as they did not feel correct to me, but being with you like this, I have not had that feeling. True, there have been multiple occasions this evening when I've doubted my resolve and been uncertain that we would get even this far for fear of what my shaky nerves might cause me to do, but with your patience and my fortitude, we've made it. Again, I thank you, and hope that I can make the next step as satisfactory for you as it will prove thrilling for me."

"Well..." I said, moaning softly as she continued to grind on my cock. "I guess that depends on how thrilling you're finding it already, because I think we've maxed out and gone well past 'satisfactory' when it comes to how much I'm enjoying this."

For emphasis, I reached up and cupped her breasts, an act that made her first moan, then smile down at me.

Chloe leaned forward, kissing me and reaching down to stroke my cock with her hand. "Then you will likely be happy to hear that I'm finding this a level of thrilling on par with, or possibly in excess of, your satisfaction."

"Good to know," I groaned, squeezing her breasts softly.

Still leaning forward, Chloe kissed the side of my neck, before taking hold of my cock and guiding the head to her pussy lips. She stopped grinding at this point, ready grasping my cock firmly as she lined it up with her entrance.

Her voice shaky, yet holding a firm resolve, she said, "I'm... I'm going to try to slide your cock inside of me now."

I reached up with one hand, cradling her chin and pulling her in for a gentle kiss. I wasn't going to say or do anything to take this moment away from her, so I stayed where I was, kissing her and holding her and encouraging her to see this through as she wanted.

With a slight bit of force, Chloe pushed against my cockhead, feeling firm resistance from the tightness of her pussy. This seemed to confuse her briefly, no doubt considering how much preparation she had done with her toy, but at the end of the day I was still significantly larger than her dildo, a realization she came to quickly.

Nevertheless, Chloe was about as determined as they came, her look of confusion quickly melting away into determination as she changed the angle of her hips and began to push down more insistently. Her experience with her toys seemed to come in handy in this moment, as she was quick to find an angle that worked for her. Even as it felt like my cock would be impossibly large when compared to her pussy, I could feel her lips start to part, allowing access for my cockhead as she began to lean into me.

Chloe's breathing quickened at this progress, and with a determination renewed, she pushed down further, and harder, her entrance spreading to accept me, widening to allow access for my thick cockhead.

Clearly, she sensed that this was progress, for no sooner had she found an angle that she liked that she pushed against me, hard, shoving my cockhead and a couple inches of cock inside of her. This seemed more than a little sudden for Chloe, as her eyes and mouth shot open in an almost cartoonish fashion. I could feel her breath escape her as she considered what was happening.

Dumbstruck, she braced her hands against my chest and pushed her upper body up, allowing her to look down and see my cock penetrating her pussy. Chloe looked down to it, then up at me, then down and up again in disbelief as she realized that I was indeed inside of her.

Out of breath, I finally heard her take one in before she finally said, "Oh."

Now, I was enjoying the hell out of the tightness of her pussy wrapped around my cock, but unable to read the current state of her shocked face, I asked, "Is that a good 'oh'?"

Shakily, Chloe gripped my chest, looking back down at my cock inside of her pussy. She started laughing, a soft, rapid sound that still didn't answer any of my questions. It sounded like she'd approached a certain kind of madness, but when she finally looked up at me and I saw that utterly gleeful look that had overtaken her face, I had my answer.

"Good?" she laughed, leaning down to kiss me. "Good is an inadequate word to describe what I am feeling right now... I've got your cock inside my pussy. Only just, to be sure, but... but..."

I finished for her, "...but by most traditional definitions, you're no longer a virgin?"

"YES!" Chloe exclaimed, leaning in to kiss me excitedly. "This is... this is it! I did it! I've... oh, wow, it's... it's amazing so far!"

It was easy to get lost in her excitement, and I wrapped my arms around her, holding her close so I could better kiss her. "It gets even better... but for now, congratulations..."

"I'm sure it does," she replied with another quick kiss. "But truly, there is only one way to find out..."

With that, Chloe pushed herself up with her hands braced against my chest once more, while I let my own hands slide down to grab her ass. The beautiful blonde looked down at me with an almost manic joy, pushing her glasses up her nose with one finger as she rocked her hips and took in more of my cock. A little at a time, Chloe slid down my cock, her smile growing with every inch as she moaned and grunted and forced every last bit inside of her, until our hips met and she had my entire cock buried inside of her. This last part took some effort, a strained look overtaking her face, but one that was also thoroughly triumphant. Pushing off of my chest, she sat up on me, looking down to the place where I'd fully penetrated her.

"I've seen my pussy taking some big fake cocks before, but this..." she mused, reaching down with one hand to lightly stroke her clit.

You'd have thought she had been struck by lightning for how hard she jolted at the contact, moaning and crying out pleasurably as her body shook. The way her pussy tightened around my cock, it took everything I had not to lose it then and there, but the promises of what was to come were enough to keep me strong as I simply gripped and massaged her ass.

Opening her fluttery eyes again, Chloe finished, "...this might force me to reassess my definition of 'big'."

She giggled then, a strange sound coming from her, but one that she grew accustomed to quickly. Playfully, I squeezed her ass and lifted her slightly.

"Mmm," she replied, forcing herself upward and allowing some of my cock to slide out of her before she dropped back down. "It's time... it's time to see what sex is really like. Can I fuck you, now?"

Squeezing her ass encouragingly and groaning when she squeezed me back with her pussy muscles, I said, "I thought you'd never ask... take it at your own pace, and have fun... because, fuck, I'm happy to be along for the ride on this one... god, you're so hot..."

Chloe experimented with different angles and speeds for a moment before settling on one she seemed to find truly pleasurable, and soon she was bouncing up and down on my cock. Though she first had a certain timidity in this act, it wasn't long before she was bouncing up and down on me with a halting, but increasingly confident, pace, moaning and reaching up to squeeze her own nipples while she fucked me.

"This is... this is amazing..." she groaned, dropping her head back as she succumbed to the pleasure for a moment, before rolling it back so she could look me in the eye. "But I hope I didn't give you the wrong impression. I don't want you to merely be 'along for the ride' with this encounter. I am grateful that you respect me enough to let me take matters at my own pace, but please don't think that I'm only here to use you to lose my virginity, no, if I just wanted a cock to sit back while I fucked it, I could use my toys. No, I wanted you because I know you're more than merely a walking sex toy; I came to you because I wanted to be *fucked* by the best."

I slid my hands up to grasp her by the hips. "Yeah?"

"Yes," Chloe replied quickly, looking down at me with fire in her eyes as she began to bounce up and down on my cock more confidently. "Are we clearer on our terms now?"

I gripped her hips tightly for purchase and started fucking up into her. "Crystal."

Now knowing that I wouldn't be taking anything away from her experience, I fucked up into her with a smooth, swift pace, matching her own before I truly began to speed up. Chloe's occasional moans became a longer, louder wail as I fucked up into her swiftly, our bodies colliding rapidly while the room soon filled with the thick, heady scent of our sex. As in school, Chloe was a quick learner here, soon fucking down onto me almost as quickly as I was fucking her. Honestly, she seemed like a natural, picking up pace and angle and understanding to please me as much as she was pleasing herself. I thought it wouldn't take her long to become something of a sex prodigy, and imagined that it wouldn't take a lot of effort for her to create her own 'Senior Year Memories' album at this rate.

Chloe rode me hard, bouncing up and down on my cock faster with every moment it seemed. She was grunting and moaning like most girls I knew at this point, truly getting into the act while I did everything I could to respond in kind, grabbing her hips and fucking up into her with a blinding speed. While everything on the bed was shaking, there was a moment I could feel her start to tremble, the look in her eyes changing as she stared down at me, reaching down to rub her clit in small, swift circles as she rode me.

Chloe was about to cum, and I knew exactly what it would take to push her over the top.

I let go of her hips, reaching up to grasp her pert, bouncing breasts, squeezing her nipples between my thumbs and forefingers. While that was enough to elicit a great, deep moan of its own, I then followed an instinct and pinched her nipples, hard.

"AAAAAAAAAAHHHHHH!!!!" she cried out, struck and shaking with another powerful orgasm.

Chloe's pussy muscles clamped down on my cock hard as she still tried, awkwardly, to ride me, her pussy positively gushing with juices as her eyes rolled back with pleasure. At some point in her uncontrollable shaking and shuddering, it seemed as if her legs had given out and she was about to go limp, but I was quick, wrapping my arms around her and holding onto her while she moaned and shook her way through this powerful cum. I pulled her to me, her chest pressing into mine as she continued to writhe and moan, her shakes getting less aggressive with every passing moment.

I pressed my lips to hers, and Chloe was all too eager to kiss me back. Much of her strength had left her, but her enthusiasm was intact, kissing and sucking at my lips as her orgasm abated.

Now, this was the sort of moment where I could have taken a moment to celebrate what she had done, and check in to see exactly how excited she still was to have had her first cum with a real cock inside of her, but I'll admit, by this point I was pretty fucking horny, and in need of my own release. Chloe had, after all, said she wanted me here so she could get well and truly fucked, and at this point I was happy to take control and show her what I was really capable of.

So, with my arms still wrapped around her, I held Chloe tightly for a moment and rolled on top of her. She gasped in surprise, but a lusty smile quickly overtook her face. She looked up at me, running her fingers lightly over my chest before giving me a knowing nod.

Bracing my hands and knees against the bed to get better leverage, I began to fuck Chloe hard. She had shown an eagerness and a certain flexibility, and while I knew I was taking a bit of a chance, the moment I started rapidly pumping my cock in and out of her rough and fast, I knew I'd made the right decision.

"Yes, yes, yes, oh, wow, oh wow! So that's what this is like? I think I like it... no, I know I like it and, OH, please, keep going, yes, like that, keep... oooooooh..." Chloe moaned, struggling for words and deciding that she'd rather lean up and kiss me while I gave it to her.

"Yeah? You like that?" I grunted, kissing her back. "This what you were expecting?"

"I wasn't expecting much from sex with any boy, but I was hopeful..." she admitted, her eyes rolling back momentarily. "Yes, that angle... fuck... keep going like that... oh, wow... when I made a move on you, it was with the expectation that you would be better than most any other boy I could find around school, but even with my understanding of your skills, I'd say you have more than exceeded expectations."