Senior Year Memories: Chloe (Patreon Exclusive Story!)

(DISCLAIMER: All characters represented in this story are consenting adults at least 18-years-old.)

Hello my wonderful patrons! As the first Patreon Exclusive Story of this month, I couldn't be happier to share this twisted and hot little tale between Ryan and the drama club overachiever, Chloe Marcus. Thank you to all of you who voted for Chloe not just to win the lead in the spring play, but get her own Patreon Exclusive Story as well! As ever, I hope you enjoy reading it as much as I enjoyed writing it!

-aimingtomisbehave33

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Unlike a lot of guys with far more questionable motivations than mine, I never went out of my way to find virgins to have sex with over the course of my senior year, but I won’t deny that in those cases where my paths did cross with one, I never forgot them. It’s kind of hard forgetting that you were a girl’s first, you know?

However, for uniqueness alone, few of these girls could readily compare to 18-year-old Chloe Marcus. An odd and hyper-focused overachiever, I’d made her acquaintance during my time working with the school’s drama club. I’d found her fascinating, if certainly odd, right away, but got attached enough to her that it might well have been my word that helped get her the leading role in our school’s spring musical production of Little Shop of Horrors. Given the rest of the drama drama that was unfolding at that time, I didn’t really get to focus on her celebration in winning the part, but that didn’t mean she didn’t want to celebrate with me in her own ways.

It was a few short days after my victory over Micah Burke that I received the text from Chloe. Or, more appropriately, when I received the long series of texts from her explaining that she wanted to thank me for whatever role I played in her winning the part of Audrey. She was rather precise and detailed in her thanks, and promises of any number of delightfully vile sex acts that she would be happy to engage in. When I responded with interest, because I knew that Chloe had a unique kind of enthusiasm that would promise a fun time, I received another long and impressively detailed series of texts giving me a precise set of instructions on where and when she would like to meet up.

Which was how I found myself walking in through the unlocked front door of her plain, almost spartan suburban house. I was familiar with its stark white walls and lack of ornamentation, and remembered my way upstairs well enough to find her room again. I won’t deny that I had a distinct spring in my step and an erection straining the front of my jeans as I approached her room expecting another fun sexual romp.

“Chloe?” I called out, seeing her door cracked half-open.

“I’m in here, Ryan!” she replied.

There was something a little odd to her voice, but I couldn’t figure out the why of it, and so approached her room cautiously.

“Everything alright in there?” I asked.

“I’m fine… I’m just trying something new and… well, you’ll see,” Chloe explained.

This raised my interest and concern in equal measures. Chloe had a comprehensive and long list of sexual experiences she wished to engage in, feeling that she had missed out by focusing so much more on her academics than social life, and while I had helped her out with a fair number of them, I knew there were considerably more that we hadn’t gotten to. Considering how many of them either required more people or got progressively kinkier… well, as noted, I was intrigued and concerned.

Stepping into the doorway and finally seeing her, this opinion hadn’t changed.

“Hello, Ryan,” Chloe said from her bed, looking at me almost bashfully. “I would come to offer you a hug and kiss in proper greeting, but as you can see, I’m a little tied up right now.”

Seeing how much of an understatement this was, I replied with a laugh, “I can see that…”

If you were to see her at school, you would think that Chloe was a cute, if conservative-looking girl, and even at a distance you’d know that she was a little odd. She could be quiet and talkative all at once, and distinctly opinionated when she knew that she was right about something, but the cuteness always remained. With long blonde hair she generally kept in a ponytail that went to her midback, her pretty, wholesome-looking and thoroughly clever face was always on full display, with impossibly blue, and impossibly focused, eyes that sparkled behind her glasses. Her conservative clothes hid her slender, fit form, but having seen her naked I knew that she had a glorious body, with firm B-cup breasts and a tight ass.

Much of that body was on display right now, as it seemed like Chloe had wanted to check at least one of the costumes off of her sexual to-do list. Kneeling on her bed, she wore a short sleeved, white, button-up shirt tied off in the middle to show off a lot of midriff, while the short plaid skirt she wore barely went to her mid-thighs in this position. Topping off this look were white knee-high socks, and her hair done up in a pair of loose pigtails that made her an almost perfect image of a naughty schoolgirl costume.

And, as she noted, she was rather tied up. With a fair amount of smooth rope, Chloe had seemingly been wrapped up and presented as a gift. Bands of rope were tied around her chest and stomach, over and under her breasts and making them look rather impressive through her top, while her wrists and ankles were bound together behind her back. This position arched her back and spread her legs in this kneeling position, further riding the skirt up her thighs and making her look, well… positively delicious, honestly.

Still laughing slightly, I said, “How did you… I mean, how is this even… did you do this to yourself?”

“The costume, or the rope?” Chloe asked me plainly. “Because I did both.”

“How?” I asked, approaching her and closing the bedroom door behind me.

“The costume was easy with sufficient thrift store supplies. As for the rope, you’d be amazed the sorts of things you can find video tutorials on if you look long enough,” she explained.

Honestly, I wouldn’t have been that amazed to find that there were video tutorials for this, but that she was capable of doing it so thoroughly to herself? That was pretty amazing. It looked like she could barely move, and while she had probably done this not long before I got here if her texts demands for my precise arrival time were any indication, it was still impressive how thorough she had been.

Then again, she always was an overachiever. I probably shouldn’t have been that surprised that she was capable of doing pretty much anything she put her mind to.

“Are you… do you need me to untie you?” I asked. “That looks really uncomfortable.”

“The costume is more uncomfortable than the rope, if I’m being honest,” she explained. “And while you could untie me if you wanted to, I thought this might prove a unique opportunity to ‘spice things up’, and thank you for helping me earn the role of Audrey… and check some items off my list and… well, as you can tell, I have many motivations here that I wish to engage with at once, and I believe most of them will be more stimulating if I remain like this for the time being. You would like to get a picture of me like this, at the very least, wouldn’t you?”

Chloe had a point there.

I pulled my phone out and snapped a couple pictures of her like this. As I did, she put on an impressive, and impressively arousing, submissive face, narrowing her eyes and opening her mouth oh-so-slightly as if she were in the middle of a moan. As someone who had made Chloe moan and cum more than a few times, I knew it was an exaggerated approximation of something porny rather than her normal orgasm face, but it certainly made for a good picture.

I slid my phone back into my pocket, considering her.

“So, now that I’ve grabbed my pictures, shall I untie you?” I suggested.

“Why the rush?” Chloe asked, smiling at me almost sweetly. “I did this as a gift, and a thank you… and as noted, to check a few more items off my list, but I can tell that you rather enjoy the sight of me like this… why not enjoy the feel of me like this as well?”

I licked my lips, looking her up and down, unconsciously taking a step toward her. “You… continue to make excellent cases.”

“Thank you,” she replied, her eyes scanning me. “But while words are one thing, if you wish to prove to me that my case is as excellent as you’d claim, I believe you should be naked.”

“Oh, uh… right, that would make sense,” I said, bending over to take off my shoes.

“I’d watch you more raptly,” Chloe said, darting her eyes to me. “But my position only allows a certain amount of visibility. Perhaps I should have been on the floor; that will be something to address for next time.”

“Next time?” I asked with some interest, sliding off my socks before tugging my shirt over my head. “This something you think you might want to try more in the future?”

“Perhaps. I’m keeping many of my options open, but if it turns out to be as enjoyable as I’m hoping it might, then, yes, I do believe that I would be interested in trying out more. After all, there are many different ways to tie someone up, and I’ve only tried this so far…” she mused, looking to the side with a pleasant little smile.

“I should really introduce you to Hope and Daphne…” I said, chuckling and dropping my pants to the floor.

At the sound of my jeans bunching up around my ankles, Chloe looked back at me hungrily, scanning my body before her eyes landed on my cock.

“Hope and Daphne?” she asked, her voice a little dreamy as she stared at my straining erection.

Seeing that I had her full attention, I might have made a slow teasing my waistband, not quite pulling it down, but playing that I might. I could see her twitch with interest, breathing more heavily and looking like she wanted to rip my underwear off with her bare hands. Considering that she couldn’t do anything, making her twist in the wind like this was certainly exciting.

“Hope’s in band and the Puma Press, Daphne’s the color guard captain… they’ve been an item for a few months now and, well, in many ways you might share some opinions with them on the subject of being tied up, though Hope could probably teach you a few things about rope play; she really knows what she’s doing…” I explained, continuing to tease my waistband.

“I see…” Chloe continued, looking more desperate to see my cock. “I would greatly appreciate your referral when we’re finished here.”

Taking my fingers out of my waistband, I decided against freeing my cock for the moment, sitting at the foot of the bed in front of Chloe and getting a nice, disgruntled moan out of her.

“I’ll certainly arrange that for you,” I said, grinning at her. “But first thing’s first… what am I to do with you now?”

The bound blonde in her naughty schoolgirl costume kneeling next to me had a certain desirable desperation to her, and I planned to draw it out of her for as long as I could… but no doubt there would come a certain time when I needed to take my own dark pleasures out on her.

In the meantime, however, it seemed as if some teasing was in order.

Sliding over to her, I reached out and ran my fingers lightly along the underside of her neck, causing her to quiver and moan slightly. I could see her flexing and attempting to writhe against the ropes, but she was pretty well restrained in place.

“You like that?” I said, dropping my voice to a pleasantly threatening tone.

“I know you’re asking me that ironically, since my reaction was quite clear on the subject, but… yes, I liked that. Immensely,” Chloe whimpered.

Alright, so there were certain types of dirty talk that it seemed Chloe would never be the best suited for, but that didn’t mean we still couldn’t enjoy our current positions. I slid closer to Chloe, rotating so that I knelt in front of her. I ran my hands over her neck, light and teasing, and then a little more forcefully, holding her in place and making her moan, before drawing my hands further down her body. I ran my fingertips down the exposed parts of her chest, and over the ropes that circled the area above her breasts, before settling them down onto her tits. I cupped them, squeezing and feeling her nipples being already quite hard.

She moaned as I rubbed her nipples, looking into my eyes pleadingly but saying nothing.

I wanted to keep my low-voiced, completely in control dominant tone in play as I continued to explore her and grope her body, but as I began to see how thorough a job she had done at wrapping the ropes around herself, I needed to ask her a question.

“Just… I’m sorry, I don’t want to break the mood or anything, but do I have to untie you if I want to see your tits?” I asked.

“Oh, no… in fact I bought this top with that in mind,” Chloe explained, smiling proudly. “It’s quite cheap and made from very low-quality fabric; tug at it forcefully enough and it should rip with considerable ease.”

I did understand the urge to rip a garment to shreds to gain access to whatever delicious goodies were hidden beneath, but didn’t normally engage in acts like that because, well, clothes don’t come cheap and I don’t want to wind up owing someone money just because I got horny. With Chloe’s encouragement in this matter, however, I couldn’t help but feel a surge of heat and excitement build inside at getting to indulge a more destructive side.

Grabbing the fabric of the shirt around her right breast, I pulled at it in opposite directions with my hands with all the force I could muster, easily tearing it up the middle and freeing her modest, and utterly perfect-looking, breast. Chloe moaned at my rough conduct, but not nearly as much as she moaned when I leaned in and suckled on her hard, pink nipple.

“Ooh, yes… that’s, that’s nice…” she purred, letting out a sharp exclamation of pleasure when I gently nibbled at her hard nub. “Ahhh… fuck…”

“Yeah?” I asked, grinning up at her. “Enjoying being completely at my mercy?”

Groaning and biting her lip, Chloe nodded. “It is a stimulating position to be in, enjoying a certain degree of helplessness… fuck… certainly aided, of course, by being in trustworthy company, but even removing that mental caveat, it is quite exciting.”

Ripping the fabric over her other breast, I leaned in and began to suck there as well, taking a certain glee in the way she moaned and tried to fight against the ropes to get more of whatever pleasure she wanted out of me. Whatever she had done with the ropes, however, made that a distinct challenge, as she could barely move and seemed genuinely at my mercy. While I did want to get her out of those ropes soon so I could really let her cut loose, I wouldn’t deny either of us the chance to enjoy this unique opportunity.

So, I kept going, alternating between licking and sucking and squeezing her nipples, sometimes going teasingly in an effort to pleasure her, other times going rougher, seeing what her limits were. Chloe groaned and moaned, whimpering pleasurably with every bit of treatment I gave her.

I didn’t linger too long in doing this, however, not when there was so much more we could do with this setup. I knelt before Chloe again, towering over her in this position. She looked up at me with hopeful, deliciously submissive eyes and a soft smile. There was much I wanted to say, and do, looking at her like this, but I couldn’t help myself but lean down and kiss her on the lips. I wrapped my arms around Chloe, pressing in close to her as I claimed her mouth with mine. She moaned against my mouth, her lips and tongue eager against mine as we passionately made out.

“This was a fun surprise, finding you like this… honestly, I hardly know what to do with myself,” I said between kisses.

“I believe the true question should be more along the lines of what you’d do to me,” Chloe clarified, chuckling slightly to herself.

“Well, I’ve been thinking about that,” I replied, lightly running my hands down her sides.

She shivered as my fingertips lightly grazed the outer edge of her abs. “H…h…have you, now?”

“I have,” I explained, running them further down her sides and then to her skirt.

I flipped Chloe’s skirt up just enough to make sure I could reach underneath it and grab her ass… and oh was I pleased to find that she wasn’t wearing any panties. Her tight, bare ass was there for my pleasure, and I took it, squeezing and toying with her while I ground against her front. I could tell by her frustration that she was desperate to touch my cock, and that this position preventing her from doing so was driving her positively wild.

I kissed her again, causing her to moan.

“And had you settled on a particular course of action, or did you want to brainstorm some concepts with me before you settle on a particular plan?” she suggested.

I slid the fingers of one hand between her ass cheeks, teasing my middle finger over her hole. “Not to break up the moment or anything, but are you suggesting we bust out some flowcharts or Venn diagrams?”

“Not suggesting, but I could second the idea if it would help you determine what you want to do to my innocent, vulnerable body any sooner,” Chloe replied, blinking up at me cutely.

The words of her dirty talk were on point, but the way she said it in an almost clinically dry manner… well, it reminded me that I was playing around with Chloe Marcus here, and that her own unique way of doing everything was part of the fun that came with any encounter with her.

I kissed her again, a little forcefully, but couldn’t help but smile at her in her enthusiasm.

“Innocent?” I chuckled. “Vulnerable?”

She rocked her head from side to side. “Innocent in my case is an overstatement of facts based around a cliched but not thoroughly unenjoyable fantasy, as you are well aware. But vulnerable? I believe I am quite vulnerable by any dictionary definition, even though I’m sure there’s no dictionary that would feature me as a picture example.”

Smiling, I kissed her again. “You know, I’ve honestly missed your unique banter.”

“Is that all you’ve missed?” Chloe asked, with an impressively cute smirk.

That was an unexpected smile, and one that I knew meant I had to up my game.

“Well…” I said, forcing my middle finger up against her asshole. “I have missed how tight your ass is…”

Chloe grimaced pleasurably, then let out a groan as my finger penetrated her a knuckle deep, then two. This would have been better with a little lubrication, but she gripped my finger and pressed back against me as best she could, arching her neck so she could kiss me.

“That’s understandable… I do have a magnificent ass, don’t I?” she proposed, rocking her ass against my fingers slightly.

“Uh huh,” I said, kissing her more passionately, before sliding my other hand around her front and under her skirt. “And a sweet, tight, hot…”

I pressed my fingers against her perfectly shaved slit before grinning darkly, then finishing, “…cunt.”

Chloe moaned as I pleasured both of her holes with my fingers, leaning her head against my chest as I continued thrusting my finger in and out of her ass, while my other hand explored her pussy. She was already quite hot and wet from some combination of this fantasy and my efforts, her luscious scent filling my nose pleasurably.

“This is… ummm… this is good, this is really, really good…” she moaned, squeezing her ass around my finger tightly. “It’s… oh, fuck… you’re really getting me hot, I’m so hot right now for you, for this, oh, god, please, please keep going, please… you’re going to make me cum so hard if you keep that up…”

“Yeah?” I smirked, kissing the side of her neck. “You like being my bound little slut? You like me using you while you’re so helpless and vulnerable?”

“I love it,” Chloe replied, smiling broadly and kissing me back. “I love it, because I trust you, and you’re really good at this… fuck, I want you to keep… keep going, please, please keep going… I’m getting close, so close… please, just a little more…”

Now, there was nothing more that I’d have liked to do than thoroughly indulge her and making her cum, but I also knew that if Chloe tied herself up like this, she wouldn’t want that easy treatment. She didn’t do this so I could make her cum as easily as I’d made her cum before; we could’ve done that without all the rope and pageantry. No, she did this whole rope fantasy because she wanted to try something new, an experiment with a certain level of consensual helplessness and giving herself over to me, and I was happy to keep pushing that further while we were together like this.

So, as much as it pained me to do so, I pulled my fingers from her pussy and ass, causing Chloe to look at me pleadingly for a moment… but only a moment, at first. I saw something flicker in her face, a faint smile of excitement for getting her started, before cutting her off at my whims. She wasn’t lying about how close she was, her arousal was thick in the air, but edging her and leaving her hanging like this only seemed to excite her more.

I wasn’t sure how much of a fantasy I had just indulged her in here, but it seemed like I might have helped her check another item off her list.

Licking her lips and breathing heavily, Chloe said, “You’re going to use me now, aren’t you? You’re going to take full advantage of my position and use me, or as much of me as you can access in this position, and you’re going to enjoy every second of it, aren’t you?”

Standing up before her on the bed, I looked down at Chloe with a pleasant malevolence and said, “Yes, that’s exactly what I’m going to do.”

Smiling slightly, she looked down to my bulge straining the front of my underwear and replied, “Well, I can’t stop you. Whatever will I do?”

Whatever fantasy she was playing into, Chloe said her lines a little too matter-of-factly to get quite what she was going for, and yet somehow I found that a distinct element of her charm. This girl, who I knew to be a rather skilled actress, still had to master the fine art of roleplay, but goddamn was it delightful seeing her try.

That certainly deserved some kind of reward…

Proudly, I stood before her and tugged down my underwear, finally freeing all ten inches of my thick, dripping erection. Even though she had seen it and been rather intimate with my cock in the past, Chloe’s eyes went wide with something like disbelief at the sight of it again so close to her face.

Moistening her lips, she began, “Wow-“

Before she could say anymore, I grabbed her pigtails in each hand and pulled her face closer to me, thrusting my cock between her lips. Though there was a brief, surprised second where she got acclimated to my cock suddenly filling her mouth, Chloe responded quickly, sucking my cock eagerly as I roughly fucked her face. She took my cock expertly into her mouth and down her throat, her lack of experience almost impossible to believe as she took me like a champ. I groaned at her eagerness and skill, that feeling of her tongue swirling along the underside of my cock with every stroke as I thrust in and out of her mouth.

“Fuck… you’re really fucking good at that…” I grunted, pulling my cock out of her mouth for a moment to let her breathe.

“I’ve always been quick with my studies… if we had a week alone together to try things out, I could probably be a master porn star by the end of it,” Chloe said proudly.

I grinned down at her, playfully batting my cock against the side of her face. “That would be an interesting career change for you.”

“It wouldn’t be my first choice… I still hope for a future within the legitimate theatre, or Hollywood if I must, but if I were given no choice but to pursue a future in pornography, I would pursue a future in pornography. If I’ve the looks and the skills for it, I would be a fool not to consider all options that would help me best optimize my future,” she explained with her quick, matter-of-fact style.

I considered the sexy, bound blonde beneath me with a wonder that she seemed to inspire readily. “Chloe Marcus… I doubt there’s another girl like you in Regan Hills High School.”

“I would certainly hope not; I wouldn’t want to have to deal with another rival for the role of Audrey,” Chloe said, her tone proudly joking. “Now, will you please give me more of that cock? I really like the feel of it in my mouth, and the way you look when you’re losing control and fucking my face…”

“Well, you asked nicely…” I said, pushing my cock back into her mouth.

We continued like this for a while, seeing just how much and how well I could use Chloe from this position. I might have become a little uncontrolled, as it wasn’t long before her hair was a mess, eye makeup ran with tears and her lipstick smeared around her mouth, but every time I took my cock out of her mouth to let her breathe, it wouldn’t be long before Chloe would ask me for more. I understood that if we kept going like this, and I gave her everything she wanted, I’d probably have to cum all over her and leave her a delicious mess…

Intoxicating as that image was, I wanted more from Chloe than that, and though it pained me to do so, I pulled my cock from her mouth and teasingly rubbed it along her cheek.

“This is fucking amazing…” I said, trying to catch my breath after such an amazing blowjob. “But I really want to be inside of you, and I think you’ll need to be out of these ropes for that. If it doesn’t fuck too much with your mood for celebration, will that be acceptable for you?”

Smiling softly and giving a swift nod, Chloe said, “Certainly… just one second…”

She grimaced for a moment, shaking and shuddering awkwardly in place before I saw the ropes go slack around her body. With some slight contortions, she shrugged her way out of the ropes.

“How… how’d you do that?” I asked.

Climbing off the bed as she untangled herself from some of the more knotted portions of rope, Chloe raised the small folding knife in her hand in explanation.

“You didn’t think I would tie myself up without providing my own means of escape, did you?” she asked, laughing slightly. “I was putting myself in a precarious position and genuinely placing much of my hope on you arriving on time; it would have been foolish to assume that nothing might have happened to you that could delay or even prevent your arrival, and there is no way I would have waited for my parents to arrive to find me like this. Too many explanations I would rather avoid, and more of them questioning my life choices that I would not want to hear.”

Chloe rocked her head from side to side, folding the knife back up and placing it in a drawer in her nightstand. “Does my having a knife on me bother you? I assure you, I was not planning on using it against you in any capacity.”

“Well, that’s great to hear,” I said, not having thought about that and brushing the thought off quickly. “No, I was just remembering how my dad studied to be an escape artist for a while, and he never told me anything about knives being part of the tool kit.”

“Well, I am not an escape artist. Thus, a knife,” she replied, bowing slightly. “Though I imagine that when it comes to escape artistry, whatever does the job would be considered appropriate.”

“Touche,” I replied, looking at her and truly taking her in as she shed the last of the ropes.

Though the ropes were certainly an exciting look on her, seeing her exposed and wearing nothing but her skimpy, tattered costume… fuck, it turned me on. Chloe was clearly used to playing characters, and an audience’s response, but the way she looked at me responding to her, I could swear I saw a little blush forming in her cheeks.

That moment of bashfulness was short-lived, however, as she soon practically dove over to me, wrapping her arms around my neck and kissing me deeply. I kissed her back, matching her intensity and pressing close to her, leading her to the bed and practically throwing her down on it. Chloe smiled up at me as I did this, pushing herself further up the bed as I crawled on top of her.

“So, would you say that this was an exciting experience?” she asked, almost clinical yet smiling up at me hopefully. “Because it seems to have awakened a certain… enthusiasm in you that I’m interested in seeing the end results of.”

“Oh, yeah?” I asked, bunching her skirt up around her waist. “You sound surprised that you looking like this and tempting me so precisely as you have has turned me into a sex monster.”

I slid my cock along her inner thighs, spreading precum as I went, before teasing the head against her lips.

Chloe groaned at the contact between us, closing her eyes briefly and biting her lip. “Sex monster… well, that wasn’t an intended or expected effect, but it is one I rather do like the sound of. Do you believe this ‘sex monster’ side of yourself can be adequately harnessed into something productive? Say, perhaps, fucking me until neither of us can see straight?”

She blinked up at me cutely, and I couldn’t help but be impressed with her evolution since we’d first gotten together. This side of Chloe was a far cry from the girl who’d tried awkwardly hitting on me at Tech Noir some weeks back, and I had to say, I liked this side of her. She was a fast learner, and if she continued to evolve at this rate, I got the impression that Chloe’s raw sexual energy would threaten to take over Regan Hills High School.

Maybe even the whole town, if left unchecked.

Rubbing my cockhead over her slit, I smiled down at Chloe, kissing her before saying, “That… sounds like a plan.”

Nodding softly, Chloe wrapped her legs around my ass, pulling me closer and forcing my cockhead inside of her steaming slit. This penetration got both of us moaning, at my size, at her tightness, the way we intermingled with each other so intimately and pushed each other. Chloe may no longer have been a virgin, and may have already been quite fond of her sizable sex toys, but she still felt almost impossibly tight as I continued to push my cock inside of her. I knew I should have been careful and slow with this, but with the little minx beneath me moaning and whimpering and smiling up at me so beautifully, whispering and moaning how desperately she needed me to fill her up, I was in no position to take this easily.

Persistent and methodical, I fed my cock into her at a concentrated pace, groaning with pleasure at every new depth I found and every bit of pressure she could put on my cock. Chloe responded beautifully, quivering against me and holding me close, moaning and groaning softly as her skin broke out in gooseflesh with every new pleasure she could feel. I made out with her, squeezing at her breasts with one hand as I persisted in pushing every inch of my erection inside of her until I was buried to the hilt.

The moment my balls rested against her ass, Chloe looked up at me with a pleasantly smug grin, wiggling her ass against me and leaning up for a quick kiss.

“Mmm, I’ve wanted to do this again since last time… I’m glad to see my memory hasn’t failed me, and you’re every bit as lovely to have inside me again as last time…” she said, quickly kissing my cheek.

“Well, I’m always happy not to disappoint,” I replied, pinching one of her nipples firmly again.

Chloe moaned, returning the favor in kind by squeezing my cock with her pussy muscles. “I doubt you could disappoint anymore than I could disappoint. You’ve got a glut of impressive skills, and while I may be new to this world of pornographic excitement our entire town seems to exist within, I also know I am exceedingly good in spite of being new to all of this… I trust you’d agree with my assessment?”

“Oh… yeah…” I groaned, kissing her and pulling my cock out slightly, before thrusting back into her. “You are utterly exquisite.”

“Mmm, high praise, considering your history…” she groaned, squeezing my cock again. “Now, come on… fuck me… fuck me hard, fucking use me as hard as you want, I need to thank you for everything, for sex, for helping me win Audrey, for inviting me to help humiliate Micah… fuck, I just want to thank you for everything. Just do whatever you want with me, I know it’ll be good and… ah, fuck me! Fuck me hard!”

Her tone was begging and needy and impossible to turn down, and it didn’t take long for me to get into gear and start pumping away at her at a rapid clip. Despite her newness to all this, Chloe took my cock like an absolute pro, squeezing me and rocking her hips in time with me to really engage in this fuck in a way that would ensure we both reached maximum pleasure. The hot, wet depths of her clutching cunt drove me onward, pleasure surging through my body as I let my more primal instincts take over.

It was looking into her eyes, though, that truly captivated me while we fucked. Chloe was a very pretty girl in any social or school setting, but in the bedroom like this, it seemed like she was truly in her element, absolutely coming alive beneath me. A girl who normally overthought anything and everything, here she was cutting loose, her high, melodic voice treating my ears to some of the most beautiful screams and cries as I pounded down into her.

Kissing her again, I smiled and continued to fuck the beautiful blonde beneath me. “I’m honestly… honestly really glad you got the part.”

“Me too,” Chloe replied, moaning. “I feel… ohfuck… a little guilty, that none of my friends got it, because they’re all so talented and so good, but so happy that I got it still… but I… but I…”

“What?” I grunted, leaning down to kiss the side of her neck.

“I just… fuuuuuuuck… wanted to know, of all the people you could’ve told Mrs. Harker to cast… god… why did you pick me? It’s not that I’m not grateful, but I am curious as to what made me stand out,” she explained, grabbing one of my hands and placing it on her breast.

I squeezed her breast, smiling and kissing her again. “It was… a lot of things… I’ve seen all of you sing, and you’re all good, and I know you’re all good actresses… holy shit, you’re so tight… it’s just… holy fuck… you’re all good actresses, or you wouldn’t be in contention for the part. I had to go with my gut, in the end, think of who seemed to really embody the innocence and hope and everything that Mrs. Harker was looking for, and you just really stood out to me in all those qualifiers.”

“Logical,” Chloe replied simply. “Can I get on top of you?”

“Of course,” I said, bracing myself as I rolled the two of us over.

Chloe took charge quite naturally, sitting up on my cock briefly so she could shed her top and toss it aside, before bracing her knees against the bed so she could bounce up and down vigorously on my cock.

“Oh… yes…” she moaned, running her hands over her body and squeezing her nipples lusciously. “This is… about as close to perfection as I can imagine anything being…”

I couldn’t argue with her there, sliding my hands up under her skirt and squeezing her ass. This only encouraged her to ride me harder, dropping forward and bracing her hands against my shoulders as she pounded down onto me.

“Perfection, huh?” I said, admittedly rather proud of myself.

“It’s given that my sample size in this matter is quite small,” Chloe explained, kissing me enthusiastically. “And my judgment is no doubt impaired by sex, but, yes, on the whole I would say that, in this precise moment in time, at least, this is probably as near to perfection as I can imagine anything being.”

“Mmm, I can probably improve on that,” I grunted, fucking up into her and squeezing her ass again.

“Can you?” she asked, not exactly skeptical, but certainly encouraging me to try to prove her wrong.

SMACK!

I raised my hand and brought it down on her ass hard and swiftly, making her cry out in surprise and delight. I could feel the pleasure of the impact radiate through her body, tensing her muscles and making her squeeze my cock ever so much more firmly as she rode.

“That was an improvement,” I grunted, squeezing her ass cheek. “Wasn’t it?”

Whimpering with pleasure, she replied, “That’s… yes, that was an improvement on my previous perception of perfection…”

SMACK!

SMACK!

SMACK!

I rained down a few more quick slaps on her ass, causing her to tense and wail and moan with ever greater urgency. Then, letting my hands travel up her body, I pulled her down, leaning upward just enough to take one of her nipples in my mouth and sucking it firmly as she rode me. Chloe’s moans got even higher and lusher in this state, bringing her nearer to those heights of ecstasy I knew myself all too capable of bringing her to.

Chloe reached down with one free hand, fingering herself swiftly as she bounced on my cock with a greater urgency. “I see now… I see now I was hasty in dubbing anything to be perfect… there are always levels beyond what one can perceive initially, levels of perfect that you can only truly experience… and it appears that you know how to access them within me… please, keep, fuck, keep doing what you’re doing, don’t let up, please, I’m getting there, I’m so close, I’m, I’m… ah, fuck, I’ll cum soon, cum soon… soonsoonsoonsoon… FUUUUUUUUUCK!!!!!”

Chloe came on me, hard, squeezing my cock uncontrollably as she shook and shuddered and rode out the waves of bliss that overtook her. I held onto her tightly, still sucking her nipple firmly as she rode through the orgasm, enjoying the ride as she let pleasure take her over.

Finally slowing and nearly going limp, she collapsed against me, breathing raggedly and laughing softly to herself, trembling and rubbing her hands on me. I took my mouth off her nipple, kissing her and sharing in her smile.

“Good cum?” I asked, kissing her again.

“Great cum,” Chloe corrected, holding onto me. “Fuck… that was entirely wonderful.”

“Agreed,” I replied.

“You can agree to that without cumming yourself? You do seem to be quite the treasure,” she said, continuing to smile down at me with the pleasantly smug grin of someone who’d just had one hell of an orgasm.

“My girlfriends would seem to agree,” I admitted, rolling back on Chloe to her amusement. “But if I’m being honest, I’m really not that far off from cumming myself…”

For emphasis, I began to pump back into her, drawing further moans out from deep within the slender blonde beneath me.

Her eyes rolling back briefly, Chloe answered, “Then why didn’t you cum in me when I had my orgasm? That would have made for some nice symmetry, and would have made me feel nice and warm inside.”

I thought about this, kissing her on the side of the neck. “I mean… I don’t think you feeling nice and warm inside is really a challenge right now, you feel pretty fucking hot.”

“That point is accurate, but not what I was talking about,” she replied through moans.

“Fair enough, fair enough… I think I got greedy?” I explained, pumping into her harder. “I didn’t want this round to be over so quickly, so I may have held back a little…”

Grunting as she wrapped her arms around me tightly for support, Chloe replied, “That is your prerogative… fuck… considering this is thank you sex for what you’ve done for me, but if you continue to hold back on me, I can’t be held accountable for whatever trouble you might get in with me.”

She looked up at me with sultry, yet playfully threatening eyes, and I couldn’t help but laugh a little. Chloe may still need to work on her dirty talk, but what she was capable of was certainly fun.

“So, I’ll be in trouble if I don’t give you my absolute best, then?” I asked.

“Plentiful trouble,” she clarified.

Thinking on this, I replied, “Well, I wouldn’t want that. I guess I’ll have to give it to you hard, then.”

“I don’t imagine you’ve much choice, honestly,” Chloe replied, smirking.

Ah, this side of her was certainly fun, and could be one that the two of us could get up to a lot of mischief with. For now, though, I was happy to pull out of her, climbing off Chloe before flipping her over. Understanding what I was going for quickly, she pushed herself up onto her hands and knees, presenting her tight ass and dripping pussy to me.

I was, admittedly, tempted to slide my cock balls deep back inside her soaked cunt again, but the sight of that ass was too tempting. I pushed her skirt up around her waist, bunching it up to give me better access. Then, gripping my glistening cock by the base, I playfully tapped it against her ass cheeks, sliding between them and running over our hole. The lubrication of her pussy juice and my precum kept us nice and slick, and soon had her moaning as well as I continued to explore her ass.

Groaning, Chloe flexed her ass cheeks, squeezing my cock and rocking against me.

“I can assume, then, that this indicates a certain interest in sliding that thick cock up my tight ass again?” she asked, looking back over her shoulder at me curiously.

Teasingly applying pressure to her asshole, I said, “I’m definitely interested, if you wouldn’t mind.”

“I would be offended if you had no interest in fucking my asshole; it is most impressive, after all,” Chloe replied, pushing back against me. “Come on, fill me up… fill my fucking ass with your cock…”

She continued rocking her hips, twerking her ass impressively against me as she further threatened to force my cock into her ass whether I was going to move or not. Smiling down at her enthusiasm, I gripped my cock and aimed it true, pushing against her tight hole and forcing the head inside.

Chloe wasn’t as tight as the first time we’d done this, but she was still almost painfully tight. It was one of those sensations where pleasure and pain kind of became one, my cock sending signals that my brain struggled to keep up with and ultimately deciding to surrender into a haze of cum-fueled pleasure. I gripped her hips, pushing forward, sliding every inch inside of her impeccably tight hole until I was buried inside of her.

While she’d been groaning and moaning and pushing back into me since I’d begun to slide inside of her, Chloe let out the most satisfied sigh I could imagine once I had buried my cock in her. Experimentally, I felt her wiggle her ass against me, groaning and mewling as she got the full dimensions of my cock once again, before dropping forward and giggling.

“Ooh, that is… mmm…” she said, almost delirious. “I’m having trouble finding words… this is a most unusual problem, but not unenjoyable…”

Pushing herself back up onto her hands, Chloe looked back at me and said, “Alright, I’ve already had a truly powerful orgasm, and you haven’t, and since I still mean for this to be a thank you, I want you to know that you can just… devastate me. Just truly give it to me. Fuck my ass, and fuck it as hard as you can… fucking use me however you want to make yourself cum as hard as possible… just mess me up.”

“You’re sure?” I asked, nervously gripping her hips.

“You doubt my ability?” she asked.

“I mean… sort of?” I admitted, my cock twitching inside of her and sending bolts of pleasure through both of us. “You’re still gaining your experience, and I’ve known some girls who’ve done a lot who still have a hard time with this sometimes when I really get going. I just want you to be certain that that’s what you want to get into.”

Chloe looked back at me, smiling a shaky, yet undeniably proud smile. “Ryan… I can take this. I’ve been practicing, and wanting more ever since we last tried this… and besides, don’t you want to be able to boast of having fucked the lead of the spring musical in the ass?”

Now, I’d fucked a lot of girls who might be considered various types of high school royalty, but Chloe had me there that I couldn’t yet boast of having fucked a girl with this title just yet. It wasn’t a matter of checking girls off on a list, of course, but she was just so damn confident, and the image she painted was so appealing, that as I looked down and considered the beautiful, pigtailed blonde who currently had my cock buried all the way up her ass who made it very clear to me precisely what she wanted from me, I couldn’t deny her this delicious depravity.

So, I gave it to her. I gave it to Chloe every bit as hard as she’d asked for it, and then some. Grabbing onto her pigtails for support, I pounded Chloe’s ass with all the force I could muster, turning her into a whining, screaming mess as my cock wrecked her ass.

“Yes, yes, yeeeeeeessssss!!!” Chloe cried out, leaning face down, ass up so she could finger herself with both hands. “Holy fuck, that’s what I needed, what I wanted! Holy fuck, keep going like that, give it to me, give it all to me, I can take it, I want it, yes, yes, yes, fuck, holy fuck, fuck my ass, fuck my ass, Ryan, fuck me harder, like that, like that! Holy fuck! Come on, please, please!!!”

“Goddamn it…” I groaned, pounding into her with all my force. “How can you… fuck, so tight… so good… how are you so good at this already?”

“Because I’ve wanted it…” she groaned. “I’ve wanted it and I haven’t gotten it until you, so I’ve been thinking and practicing, and now that I’ve got it, got you here… fuck, I’m ready to go to my limits… come on, please, harder… harder!”

“You’ll get it,” I grunted, looking down at this blonde girl with some awe.

Even with what we were doing, I was in awe of Chloe, this girl who looked so innocent and was so thoroughly dirty. She was truly one of a kind, and while I knew I wouldn’t share every sexual adventure with her that she had, I knew I would enjoy every moment that we were together.

Feeling my cock swelling, I reached down, pulling Chloe up so her back was to my chest. With my arms wrapped around her, I squeezed her breasts, holding on tight as I grunted and fucked up into her, kissing her neck.

“Gonna cum soon… where do you want it?” I asked.

Moaning, Chloe kissed me, then replied, “All over me… soon?”

“Soon,” I confirmed.

“Alright,” she said, pushing off of me and pulling my cock from her ass.

Chloe lay down on the bed before me, still urgently fingering herself while I stroked my cock and could finally hold back no more. With a violent grunt, I came all over her, splattering cum on her chest, her tits, and all over her face. Chloe moaned lusciously with every blast, groaning and writhing and crying out with her own shaky orgasm moments later.

Panting and sweaty, I collapsed next to her after the last of the orgasm wound down, the two of us shaking and laughing softly to ourselves.

“So…” I started, chuckling. “How was that for a showstopper?”

Grinning, Chloe replied, “It would make a fine finale.”

Looking at her, so messy and depraved and fantastically gorgeous, I couldn’t help but bark a laugh and replied, “Finale? I thought that was just an opening number. You’ve got a long to-do list, don’t you? Let’s see what else we can check off…”

Sitting up and letting my cum roll down her body messily, Chloe smiled a pretty, sweet smile that was all the reply I needed to know that this was going to be a long afternoon.