Senior Year Memories: Sasha (Patreon Exclusive Story!)
🕑 Added 2025-02-03 01:12:49 +0000 UTC(DISCLAIMER: All characters represented in this story are consenting adults at least 18-years-old.)
Hello my wonderful patrons! Well, this is one of the more offbeat picks for a leading lady, and I can't help but be excited to see what you all think of this one as we bring the fun-loving redheaded cheerleader, Sasha Pearl, into her own Patreon Exclusive Story. I had a LOT of fun with this one, playing around with some new settings and ideas that I hope you'll also enjoy. To all of you who voted for her in this story, I can't thank you enough for your votes and support! As ever, I hope you enjoy reading it as much as I enjoyed writing it, as I think this one turned out rather enjoyable!
-aimingtomisbehave33
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As requests went, I’ll say that this was hardly one of the most unusual ones that I’d encountered during senior year, even if it was still rather unorthodox.
It was, on paper at least, a simple request. Peter Nixon, one of the more unexpected friends that I’d made this year, had been planning on taking his girlfriend out to a carnival being held in Blair Valley that was only in town for a couple nights. However, when his grandpa, who lived a few hours away, broke his hip and needed the family’s help to move some things around to better aid in his recuperation, the date seemed like it would be a no-go. However, at the last minute, Peter came up with an idea to have the date night still be on, albeit with me escorting his girlfriend to the carnival rather than him, as he knew that she and I would have a lot of fun together.
I didn’t need to consider the request for long, since Peter was a friend, and I’d already become well-acquainted with his girlfriend, so that was why I dressed up in one of my nicer pairs of jeans and a clean-enough polo to escort her on a salvaged date night to the carnival.
The event was being thrown in one of the overflow parking lots at the Blair Valley Shopping center, and was about as colorful and loud and gaudy as you could expect and want a carnival to be. Dangerous-looking, brightly lit rides were crammed far too close to each other, overly expensive games sought to cheat people out of their well-earned money, and the smell of foods that likely shouldn’t have been fried being fried filled the air.
All in all, it was everything that you could want out of a carnival, but it was the company that truly made the evening for me.
“This kinda reminds me of something, but I can’t quite put my finger on it,” 18-year-old Sasha Pearl said as she strolled alongside me down the main avenue of the carnival, smiling that big, goofy smile that always endeared her to me in a way that made her unique among the cheerleaders.
“Oh?” I asked, eyeing the girl standing beside me and feeling a familiar warmth that I rather enjoyed.
At 5’9”, the pale, freckled redhead was every bit as beautiful as any of her fellow cheerleaders, with a fit, slender body that was held inside of a flowy, light blue dress that stopped just below her knee (a sweater tied around her waist in case the evening got chilly), and a lovely face framed by her short-cut hair that lit up any room whenever she smiled. Unlike most of the other cheerleaders, though, Sasha was also a proud nerd who did nothing to hide her interests that normally wouldn’t mesh with the more popular girls. She never hid her big, toothy grin, and wore her prominent glasses with pride, making her sparkling blue eyes all the more lively-looking. Sasha had always been one of the more playful and enthusiastic girls I’d met over the course of this year, and walking around this carnival with her, taking what joy we could from how utterly cheesy the experience was… well, it felt right.
The fact that she’d been eyeing me the entire night like she wanted to fuck me as soon as possible, well, that was just icing on the cake, because whenever Sasha and I had messed around before, we both had a lot of fun. I had to admit that I was looking at her with a similar hunger, but I was willing to be patient for now. I was supposed to take her out tonight and make sure she had a good time at this carnival she’d been looking forward to for so long, and I meant to hold to my promise.
“Not the carnival, I’ve been to plenty of carnivals and know that kind of familiar,” Sasha clarified, giggling as she craned her neck to look at a nearby juggler. “This is a different kind of familiar… this whole night, the date setup, I mean. I know I’ll figure it out yet, it’s just bugging me now.”
“Well… should I be distracting you?” I mused. “Trying to win a prize to impress you? Whispering dirty thoughts into your ear so you’re not bothered by familiarity and instead get all shaky and quiver with thoughts of what you know I can do to you?”
I said this easily, but with a playful smile of my own that I tried to match to her energy. The way she cocked her head at me, her eyes sparkling with even more mischief, I figured that I hit upon something.
“I’m not asking for a distraction, but whispering naughty ideas in my ear is never a bad idea,” she explained, keeping her tone light and eager. “But that doesn’t mean that you’ll have successfully distracted me, because I can think on this while you’re turning me on and… OH! I think I’ve got it!”
And to think I had just come up with some deliciously dirty things to whisper in her ear. Ah well, those could wait until later.
“Go on…” I said, curious.
Smiling with a tremendous look of satisfaction, Sasha asked, “So, how into old movies are you? Because that’s kinda important to what I’m getting at here, and I know I like some old movies and music that a lot of people don’t like, so I gotta make sure.”
“How old?” I asked, raising an eyebrow with some amusement. “Are we talking something from the 80s? 60s? Silent movies?”
She laughed, lightly poking me in the arm. “Nothing that old, no… it’s just, this whole Peter asking you to take me out because he got busy all of a sudden, it’s like the first act of Pulp Fiction. You know that one?”
I did, and I grinned at the familiarity. “I mean, this carnival’s no Jackrabbit Slim’s, but it’s still got its high points. And I can see why you’d jump there first… it does feel kinda similar.”
Sasha’s grin grew. “Yeah, right? Except we’re a lot less sad than Vincent and Mia… and rather than simmering chemistry that doesn’t go anywhere because we’re terrified of the guy who asked yo to take me out, we’re definitely gonna get some action later, because Peter’s no Marcellus Wallace.”
Well, I liked the sound of that.
“We really gotta hang out more often,” I said, laughing and taking her arm in mine.
“Oh, for sure,” she replied, playfully taking my hand in hers as we walked. “I know you got a lot of choices between a lotta different flavors of ass you can be getting around school and that I am but one of many, but when we can and do get together, not gonna lie Ryan, I really fucking look forward to it. You’re so much fun.”
I laughed with her, trying to wrap my head around being a “fun” guy. It wasn’t long ago that I felt like pretty much the exact opposite of fun, and now having a girl as sweet and playful and hot as hell as Sasha calling me fun, well, it had a way of making my pride swell just a little bit.
Okay, more than a little bit.
I may not have known Sasha as well as a lot of the other girls I’d gone out with during senior year, but I knew enough to know that I really liked being in her company, and that I wanted to make the most of every minute we did have together.
“So, what do you want to do next?” I asked, grinning at her. “Play some more games? Grab a snack? Hit up the mirror maze? I think I saw that back near the front…”
Sasha laughed. “Yeah, the mirror maze is a no-go. From what I heard around the bathrooms, some guy did a whole bunch of drugs, freaked out in there and wound up smashing through a couple of the mirrors yesterday, going full Kool-Aid Man. I mean, it’d be fun to check it out and see what kinda mess is or isn’t there, but, no dice tonight, I think.”
I chuckled at the story. “You sure you don’t wanna sneak in? I’ve been doing a lot of sneaking around this year and have gotten pretty good at doing it without getting caught. Mostly to fuck around, sure, but the fact that I’ve gotten really good at sneaking around while horny as fuck is probably more impressive, actually.”
She rolled her eyes, still smiling broadly. “You might be able to avoid getting caught because everyone wants to fuck ya, but I’ve got grades and a reputation to keep up; I’m not looking for that kind of trouble. You’ll have to get me a lot hornier than that before I’m compromised enough to do something like that.”
I raised an eyebrow. “That sounds like a challenge…”
I leaned in, whispering in her ear. “…you know it won’t take much for me to get you that horny… you want me to remind you of what we did over New Year’s? You remember how my cock filled you up? How my tongue and fingers made you cry out again and again? I can make you so hot you won’t be able to see straight, or walk, or, well, pretty much anything else… yes, I can get you to sneak off and fool around in that mirror maze if I really want to.”
Sasha licked her lips, eyeing me a bit giddily. “And do you really want to?”
I straightened myself back up, walking beside her. “I haven’t made up my mind on that subject yet, but I do like the way my deep, dark, dominant voice got you to slow down a little.”
“Oh, that’s not all it got me to do,” she giggled, leaning in to whisper in my ear. “You got me pretty fucking wet there.”
“Oh?” I asked, eyebrow raised. “How wet?”
Biting her lip again thoughtfully, Sasha cocked her head to the side. “Wanna hop on the Ferris wheel and find out?”
Looking over at the carnival’s Ferris wheel a short walk away, I answered, “Yes. Yes I do.”
Admittedly, it was one thing to talk about fooling around a little in a Ferris wheel than it was to actually get into one and do it, between buying tickets and getting in line and waiting the arbitrary amount of time for them to decide to put people on and take people off, and it made it a particular challenge to keep the energy that had led us here going. Nevertheless, Sasha and I were more than up for the task, sneaking in gropes and whispering the dirtiest thoughts we could into each other’s ears as we made our way through the line to keep the energy going between us.
Of course, being the analytical and nerdy types that we were, in this waiting period we also did our research. For a small carnival, it was a fairly sizable Ferris wheel, and it seemed that each car on it seemed to have an average trip of about ten minutes from when people got on to when they got off. More time would have been better, but ten minutes was something that I knew I could work with, especially with how charged the two of us were keeping each other. As well, to our benefit, the cars were designed to have maximum visibility to the front so you could get a nice view of whatever vistas its altitude allowed for, but seemed to be designed in such a way that they were majority blind spot, which would give us a nice bit of privacy.
All of this was quite promising, by my estimation.
By the time we made our way to the front of the line, we were so fucking hot for each other that it was a miracle we hadn’t already stripped down and gotten it on already. The carny operating the ride, looking at us as we took our seats, clearly knew something was going on. He looked more vaguely annoyed than anything else as he sized us up, but that didn’t stop him from dropping the bar across our laps and making sure we were nice and secure.
“Look, just make sure you keep whatever you’re doin’ quiet, ya hear? This job ain’t great, but that don’t mean I wanna get in trouble,” he explained. “And don’t leave a fuckin’ mess or something like that; they make me clean that shit up.”
Sasha giggled. “We’ll be good, promise!”
The carny rolled his eyes at us, but before we could linger for long on this, Sasha and I were taking to the sky, the wheel turning as we were slowly raised upward.
Still giggling, Sasha explained, “I was lying… if it wasn’t clear, I was so lying. I plan on being very not good.”
To emphasize this, she leaned in, kissing me on the side of the neck, a not unpleasant sensation, if I’m being honest.
“I’m not sure how,” I said, adding more than a hint of playful sarcasm to my tone. “But somehow, I got that impression.”
“Yeah?” Sasha asked, sliding closer in next to me.
“Yeah,” I replied, wrapping an arm around her shoulders and pulling her in close so we could kiss.
The shape of the Ferris wheel cars was such that we were pretty much all blind spot, as far as all the other cars were concerned, and if we were really ambitious, Sasha and I could have gotten up to some serious trouble in here. Of course, that trouble also wouldn’t have been very safe, since it would have involved disabling the lap bar, shifting positions and rocking things way more than anyone ought to be rocking these cars, and considering how unsafe this particular attraction already looked, I wasn’t going to try and push my luck by actually having sex with Sasha in here.
Nevertheless, that didn’t mean we were completely without options.
As we made our slow path toward the wheel’s apex, Sasha and I made out. Our kisses were slow and playful and plenty wet, and with her encouragement, my free hand was soon squeezing her tits. The carnival music and the screams of people on other rides filled the air, but the higher we got, the more they quieted, giving us a greater chance at some privacy of our own. Not that we needed privacy to make out, of course; we were both pretty shameless people, and we were hardly the only people who had taken an opportunity to go make out on the Ferris wheel. Nevertheless, we were also a little more ambitious than just some making out for how hot and heavy we’d geared each other up to be, and we were going to see just how much we could get away with.
The Ferris wheel stopped with us about three-quarters of the way to the top, no doubt to let some people off and let more on, and there was no way we weren’t going to take advantage of that.
Smiling giddily, Sasha practically squealed, “Perfect!”
She arched her back just enough to untie her sweater and pull it out, slipping it under the lap bar just enough to cover her lap, while hiking up her dress underneath it.
Getting an idea of what she wanted, I had to agree. “Perfect.”
“Uh huh,” she replied. “I’ve done some weird and kinky stuff before, but this, this is a first… doing this in public, on a Ferris wheel, it’s kinda crazy, but I like it.”
I slipped a hand into her lap, underneath her sweater and let it settle between her rather warm thighs. “I’d hope it was an idea you liked since, I mean, it is your idea.”
“Oh, I definitely like it… just, gotta note some of these things out loud,” Sasha continued, reaching beneath her sweater with me and pushing my hand distinctly higher.
I growled pleasantly at the discovery that she was quite warm, her heat radiating rather impressively even through her panties. Grinning, I then pressed my fingers against the fabric, teasing her pussy through her panties. Sasha held back a light squeal, biting her lip as I probed and pressed against her, making her writhe more against my hand.
She groaned, “Mmm, you’re just teasing me… but that’s alright… I like a lot of teasing… gets me all nice and hot before I cum… yeah, tease me all you want, get me nice and hot for you… I won’t be able to help but cum so fucking hard when you do that.”
I chuckled nervously, looking around with some interest. “I mean, feel free to cum as hard as you want, but I think we’re going to need to keep it on the quieter side here than most places.”
“Ugh, I know,” Sasha bemoaned, continuing to rock against my hand. “One downside to getting this level of kinky; kind of hard to get as loud and hard with things as I’d normally want to… but some sacrifices must be made to make things this kind of interesting.”
Smiling, she leaned her head on my shoulder, whispering, “I think the tease would be even better if you got your fingers beneath my panties. You did want to see how wet I was, after all, right?”
I grinned at the implication, slipping my fingers underneath the elastic of her panties. “I mean, I do want to see just how wet you are, but once I get beneath these panties, you and I both know it won’t be much of a tease anymore.”
“True,” Sasha responded, arching her back just enough to better encourage my hand between her legs. “But this won’t be all that long a ride, and I wanna cum before we’re done, so, a little tease will have to do, and a nice hard cum will take me the rest of the way.”
I had a hard time arguing with her logic, especially when the Ferris wheel kicked into gear again, sending us up toward its peak. Sensing the vague urgency of the situation, while also wanting to make this good, I kissed Sasha again. She looked up at me, that pretty, goofy little smile of hers seeming so broad and so utterly excited that I couldn’t help but feel my own enthusiasm rise. Looking into her sparkling blue eyes, I slid my fingers underneath the waistband of her panties, running them through her landing strip and finding her hot, wet pussy with ease. As promised, she was quite wet, her juices already flowing quite freely and coating my fingers quickly as I rolled them over her lips, exploring.
Sasha moaned, clinging to me and kissing me again.
I was a little bolder with my next motions, stroking her more insistently as I probed. I never probed too deeply, but will admit to being a little shameless, pressing two fingers gently between her lips just enough to be inside her up to the first knuckle, before pulling out just enough once she let out a nice, sweet moan.
“Oh, this is naughty… very naughty fun,” Sasha groaned, kissing me and smiling brightly. “Oh, we haven’t even really gotten started, and it’s so fucking naughty… oh, fuck, there’s really something to doing something we shouldn’t be doing like this, isn’t there?”
We were already on our way down, about to finish our first loop, and while I felt like I should’ve been afraid of getting caught, I couldn’t deny Sasha’s point. I’d done a lot of things this year that were ill-advised and could have gotten me in a lot of trouble, and while this was far from the worst, it was also one of those moments where I felt the most exposed. Rather than filling me with fear, it gave me a distinct sense of exhilaration, especially because I was feeling so exposed. We could be caught so easily, but somehow we both just knew that we were going to get away with it, a fact that only added to the thrill.
Sure enough, on our first trip to the bottom of the Ferris wheel, we weren’t stopped, or even noticed by the carny who had tried to gently warn us earlier. We kept going on our next circuit upwards, my hand in her lap hidden by her sweater, and my audacity growing bolder with every passing moment.
Smiling playfully, Sasha leaned in to whisper in my ear. “It’s like… ooh… we can do whatever we want… it’s kind of great, isn’t it?”
Moving my fingers upward to rub on her clit, I replied, “I couldn’t agree more…”
This brought out a particularly high moan from Sasha, followed by more of that sweet, girlish giggling that managed to get me even hotter for her. I kissed her back with a certain ferocity as soon as we’d gained a little more altitude and set about rubbing her clit with firm, purposeful circles.
Now, while it was fun being naughty like this, I was also realistic that it wasn’t the sort of thing that we could get away with forever, and so as we made our second loop around the Ferris wheel, I was more than happy to pick up the pace. I fingered Sasha with a greater speed and purpose, paying special attention to her clit while she moaned and bucked against me. I was happy that the Ferris wheel, between its music and ricketiness, was as loud as it was, because even with her best efforts to keep quiet, Sasha was a loud and enthusiastic lover.
It was an interesting game, wanting to give her the attention she deserved while also being aware of our surroundings. Every time we made it down to the bottom, I would slow in my efforts, edging Sasha when we could be observed, and then jumping in to pleasure her with a greater enthusiasm whenever we were out of sight. In those moments when the Ferris wheel would stop entirely to let people off and on, I would take full advantage of the situation, pressing in and hurriedly running my fingers over her clit in quick little circles that had her squirming and trying to hold back moans.
“Ah, fuck… fuckfuckfuck… that feels, mmm, so good, so nice, haha, oh, wow…” Sasha murmured, looking up at me with a giddy excitement that only fueled my own enthusiasm. “It’s, wow, getting there… like, you’re really getting me there, feels good, soooo good… fuckfuckfuck, oh, god, I wish we were somewhere else… this is naughty fun, but I want to be somewhere else, somewhere we could strip down and go crazy on each other, because I’d let you go crazy on me… fuck… I want you to go crazy on me, so much, just down and dirty, crazy and horny and messy… fuck… fuckfuckfuck…”
I liked the picture she painted, leaning in and kissing her neck so I could whisper in her ear. “Well, if you cum for me, nice and hard… we can see about finding someplace we can sneak off to… someplace where we can get a little more naked than this and fuck like crazy…”
“Mmm, god…” she moaned, rocking against me insistently. “I want it… I want that so bad… I want your cock… want to fuck you… want… god, fuck, harder, harder, just give it to me a little harder, a little more pressure, like that, right there… faster… faster… please, keep going, I’m so close, so fucking close, just give it to me a little harder, Ryan, please, feels so good, so good, so… AHHHHHHH!!!”
Sasha leaned in, biting my shoulder to hold back whatever screams she wanted to let loose as she came. It wasn’t the hardest orgasm that I’d ever fingered a girl to, and maybe that was by design… as fun as it was to imagine that we wouldn’t get caught no matter what we did, the possibility of being thrown out of here (or worse) because I’d given Sasha a nice screaming orgasm wasn’t something I really wanted to entertain. So, I kept it nice and mellow, slowing when I felt her get close, and taking her over the edge with just enough pressure to make it good for her, without completely breaking her.
For her part, Sasha seemed to be enjoying my efforts regardless, her body shaking and trembling as she held onto me, one of her hands reaching up to cup a breast through her dress, her fingers finding and pinching one of her nipples as she continued through her rolling orgasm, her hips bucking against my hand with a need for more.
Finally letting up from her bite, she looked up at me, smiling weakly as the last vestiges of her orgasm rolled through her. Enjoying the sight of her like this, I kissed her on the lips firmly, giving her clit one nice, firm tweak for emphasis and loving that high little squeal of pleasure it pulled from her.
“Okay… okay…” Sasha replied breathily, laughing slightly to herself. “Well, I guess that’s one thing I can cross off the bucket list…”
I raised an eyebrow, pulling my hand out from under her sweater. “You’ve got a bucket list? And getting fingered on a Ferris wheel was on it?”
“Well, metaphorically speaking,” she giggled, taking hold of my hand and bringing it up to her mouth. “It’s not like I’m thinking my time is short or anything and I’ve put pen to paper to say things I wanna do before the end, but, it’s one of those cool sorts of ideas I’ve had for a while and I can say it definitely lived up to the hype. The company definitely helped, though…”
Sasha brought my juice-coated fingers up to her lips, gently sucking them clean. I groaned softly, shifting in my seat as I’d become suddenly quite aware of my own straining erection.
I wasn’t the only one who was aware of it. Sasha looked down to the growing bulge at the front of my pants, her eyes growing wider with excitement.
“Well, we’ve gotta do something about that,” she said, looking around, possibly to see if we could get away with doing something here. “But this isn’t gonna work… don’t think I can get away with getting you a handy or a blowjob quite as subtly. I mean, we can try, and I’m up for trying if you’re up for trying, but if we could find someplace nice and private, think of what we can do…”
As we began to descend the Ferris wheel yet again, I looked out over the carnival, and was suddenly struck with inspiration.
“You good to try something out that’s so crazy it just might work?” I asked.
“If it means getting laid, fuck yeah, I am,” Sasha replied enthusiastically.
I grinned at her, as ever, impressed and turned on by Sasha’s eagerness. The two of us may not have had the deepest connection in the world, but her excitement had a certain contagious quality to it that I greatly appreciated, and I wasn’t going to deny that the two of us could really get hot and heavy whenever we were together.
So, Sasha was willing… now to figure out if I could pull off the next part without the two of us getting in any trouble.
***
As it turned out, it was beyond easy to pull off the next part without getting into any trouble. Once we were off the Ferris wheel and looking more than a little respectable, we strolled around the carnival trying to look nice and innocent as we made our way back toward the front. Once we got around to the mirror maze, I thought it would take all of the sneaking skills I’d learned over the course of the year to infiltrate the closed-down attraction.
Security being as non-existent as it was, however, that didn’t turn out to be all that necessary. While the front of the portable mirror maze unit was covered in caution tape and blocked off with traffic cones, it was easy enough in the darkness to sneak around to the back of it and make our way in through the exit. The door was unlocked, though we made sure to fix that once we made our way inside since, well, we didn’t want any interruptions, did we?
It was a surreal experience going inside the abandoned maze. Sturdy mirrors and panes of plexi-glass made it a confusing labyrinth for the pair of us to navigate our way through, made all the more difficult by how the flashlights on our phones bounced off of nearly every surface.
Exploring on our way to the middle (after more than our share of collisions with the walls), I could see just how right Sasha was about the rumors she’d heard. A few panels were shattered and knocked down, which seemed truly impressive for how sturdy the panes seemed. Whatever drugs the guy was on had to have transformed him into a fucking freight train… but if it got us this level of privacy, I wasn’t going to complain. That it seemed like his incident made it so the maze was exceptionally cleaned out only seemed like icing on the cake.
“I feel like I should be worried about finding my Tethered somewhere in here,” Sasha chuckled to herself, bracing her phone on the ground against one of the mirrors, bouncing it off of enough surfaces to really give us some light in the darkened maze.
“At a place this cheap? More like finding our Tethered as ordered from Wish,” I chuckled, running my fingers lightly over one of the mirrors.
“Yeah, something like that, but not having to worry about monsters has its benefits too,” she said, clearing her throat dramatically so I would turn my attention toward her.
I looked over at Sasha with some interest, finding her looking particularly sexy, in a wholesome sort of way. Her pale blue dress, glasses and red hair gave her that sweet, girl next door kind of look that would have gotten me pleasantly hard even if I wasn’t already quite erect from anticipation and need.
Of course, “sweet” and “wholesome” went out the window when she shrugged out of her dress, dropping it down her body until it puddled around her ankles. With a practiced ease, she then removed her bra and panties, now standing before me wearing nothing but her shoes and socks, which likely remained a fair precaution in here. Seeing her round, firm breasts bared to me, her nipples pink, hard and inviting was certainly enticing, though not nearly as inviting as the sight of her pussy. Her pink lips were still quite prominent and moist from what we’d gotten up to in the Ferris wheel, a bright red landing strip pointing downward toward them almost like an exclamation.
If that wasn’t invitation enough, Sasha then playfully cocked her hip out to the side and said, “Come on, let’s fuck!”
Well, it didn’t get much more direct than that, did it? I closed the distance to Sasha quickly, wrapping my arms around her and pulling her in close for an eager, messy kiss, one that Sasha readily reciprocated. Her lips were sweet and her kisses energetic, her tongue dancing lightly over mine and her naked body feeling oh so perfect against mine as we made out. Now that we had a semblance of privacy, I meant to take full advantage, dropping my hands down to her tight ass. She moaned against my lips as I squeezed her butt, rocking it excitedly against me.
“Mmm, I love how you handle my ass… fuck…” Sasha mewled as she reached down for my belt.
We didn’t stop making out as her deft hands first undid my belt, then unbuttoned and unzipped my pants, hurriedly pulling them down around my ankles. She lingered a little bit longer on my underwear, grinning slightly as she ran her hands over my prominent erection, but soon that was a concern of the past as well when she tugged at the waistband and dropped the underwear to the floor, revealing my thick, ten-inch-long cock.
“Fuck…” she let out with the slightest sigh, running her hands over my cock.
She did this first with a light, exploratory touch, before wrapping her hands around me and stroking me. There was gentleness at first, of course, as Sasha was at heart a very gentle girl, but once her thumbs reached my cockhead, finding the precum flowing freely and making me nice and hurriedly slick, that was when all bets were off. Finding out that my arousal was every bit as charged as hers, she became more insistent with her handiwork, stroking me with a certain urgency as she spread my precum around freely.
“Mmm, this is all for me, isn’t it? I really got you going on the Ferris wheel there, didn’t I?” Sasha asked, playfully teasing my cockhead with her thumbs.
With a pleasant little growl, I replied, “You had me going since I first saw you tonight.”
Though the light offered by her phone reflecting around the mirror maze wasn’t exactly the best, I could swear I saw Sasha blushing just then.
“Awww, that’s fucking sweet,” she giggled, leaning in to kiss me again.
I shrugged, kissing her back before saying, “What can I say? You’re fucking hot.”
Sasha giggled some more. “I’m a lot of things, but hot’s one of my favorites, not gonna lie to you there… now why don’t you push this inside of me and let me know how hot you really think I am?”
While this was something I could have easily expressed in words, I didn’t need her to elaborate on what her actual point was. I reached down for Sasha’s right leg, pulling it up slightly for better access, while Sasha herself reached down between us and took hold of my cock. Angling it downward just enough, she rubbed my cockhead over her hot little slit. Even though it had been a little while since we were on the Ferris wheel, I found it encouraging to feel just how hot and wet she still was as she lined me up for entry.
Oh, this was going to be fun.
Sasha looked up into my eyes, biting her lip through her grin in anticipation of what would come next. I leaned in, pressing her back against one of the mirrors for support. While I worried, briefly, that it might give way like those the guy had done his Kool-Aid Man impression through, it supported Sasha and I leaning against it easily.
I lifted her leg a little higher, ensuring I had the perfect angle for entry, before I began to slowly sink my cock into her delicious cunt.
“Ah… fuck…” Sasha groaned, biting her lip again as my cock began to part her perfect, tight pussy lips.
“Yeah… fuck… you’re so fucking tight…” I grunted, trying to perfect the angle.
“Only ‘cause we’re standing,” she joked, gasping slightly. “Oh, who the fuck am I kidding, I’d feel tight to you no matter what…”
“And I’m pretty sure you’d be tight to any guy… all that working out, all those cheer practices, keeps you so nice and tight…” I said, rocking back and forth, working my cockhead into her slit a little bit at a time.
At least, until there was no such thing as a little bit, and the first several inches of my cock simply slipped inside of her. Sasha’s eyes went wide with surprise at the sudden ease after the initial difficulty, but managed to keep fairly quiet.
I grinned, and may have let out a noise of my own in the pleasure of it all because, well, she did feel fucking good. With one hand still holding up her leg, I reached the other up to squeeze one of her breasts, applying pressure to her nipple in a way that brought out the sweetest little moans from her as I continued feeding my massive cock into her perfectly tight cunt.
“Mmm, I was really… really hoping for a night like this before all the plans went out the window… thanks for filling in, for Peter… fuck, I know he wanted us both to have some fun tonight, and I know he’s gotta be glad we’re doing this,” Sasha groaned, kissing me as I bottomed out inside of her.
There was a time once where one of my friends asking me to take his girlfriend out with the understood implication that the night would end in sex would have seemed peculiar to me, but after pulling back the curtain and finally understanding what Regan Hills was like, I didn’t even blink at Sasha’s comment. Instead, I smiled, and I kissed her, squeezing her nipple more firmly as I savored what it felt like to have all of my cock buried deep inside of her.
Of course, when I next opened my eyes and was greeted by my own reflection in an adjacent mirror, I couldn’t help but laugh a little. I’d fucked in a fair few strange places this year, but a mirror maze was certainly a new one. Seeing our reflections, bouncing around an almost endless void of mirrors was one of the more surreal sights I’d seen, and one that might have occupied my time considerably if I hadn’t already been focused on a different task at hand.
Grinning, I began to pump up into her, each thrust giving Sasha another reason to squeal slightly, her pussy tightening around me every time I pushed inside of her. While her smile seemed impossible to shake, I did enjoy the sight of her losing herself in the moment, her mouth dropping open as she let out the cutest of moans, her eyes rolling back and fluttering briefly before she looked back at me, excited and so unbearably sweet-looking in spite of how wonderfully dark an act we were committing.
I didn’t know how loud we’d be able to get in here, if we’d be silent to the outside world or heard by everyone who passed (or if anyone would care, under the circumstances), but as I began to assume a proper pace of fucking her up against the mirror, I didn’t care. I was surrendering to the absolute batshit insanity of where we were, and I was going to enjoy every moment of it that I had with Sasha Pearl.
“Fuck, fuck, fuck…” I grunted, every thrust giving me a new, sharp jolt of pleasure.
“Mmm, yeah, that is nice…” Sasha giggled, kissing me. “Fuck… I knew I’d be getting some dick tonight, but I didn’t think it’d be… well, I didn’t think it’d be anywhere close to this!”
“I do like it when I can surprise a girl,” I replied, squeezing her breast as I continued to thrust up into her.
“Oh, this is a nice surprise… I thought we’d be going back to my place, or even with as hard as you were, maybe just fucking in my car, but this? So much better… fuck, this is the kind of encounter I’m gonna have stories about… when I tell the other girls, they’re gonna be so jealous… I don’t think any of them have done anything this weird before,” she moaned, dropping her head forward and leaning into me.
“Well, if it means making them jealous…” I said, grinning and kissing her deeply, then pounding up into her with exceptional force.
Though Sasha had previously had her arms wrapped around me for support, now that we had gotten into a pretty good rhythm with this fuck, she had dropped one down between us, fingering her clit while I pumped into her with a greater passion. While this was certainly a bit of an awkward position, I was certainly happy to know that she was enjoying herself, possibly even more than I was. She giggled and laughed and moaned as I fucked her up against the mirror, her body shaking with the intensity of the fuck every bit as much from her own pleasure.
“Yeah? You wanna make the other girls jealous?” Sasha teased.
“I mean, why wouldn’t I?” I said, kissing her quickly. “Cheerleaders… you’re all some of the craziest fucks I’ve ever experienced, and you’ve all got this kind of competition with each other when it comes to sex… if I fuck you hard enough and fun enough that it makes them jealous, they’ll all jump me even harder… it’s the best…”
“Ah, I see the cunning of your plan now… not bad,” she admitted, playfully squeezing my cock with her pussy. “Of course, it’s also a strategy that can blow up in your face, so easily… not that you won’t enjoy it, but I can seeing that one going so wrong, so fast…”
Sasha was laughing, and I was too stuck in the moment to do anything but fuck her, but that didn’t mean she hadn’t given me some pause.
“Oh yeah?” I asked.
“Yup,” Sasha giggled. “If you keep forcing us to up our game by making us jealous like this… fuck… you’re gonna push us harder and harder until you push us into doing something that you can’t take…”
“What makes you think I can’t take anything you girls can throw at me?” I groaned, pumping into her with a slightly greater intensity.
“Fuck, keep going like that, I’m gonna cum soon… fuckfuckfuck…” she moaned, holding onto me more tightly. “Fuck, keep going…”
I slowed, grinning at her with some amusement. “Oh, come on… you didn’t answer my question…”
Sasha’s eyes rolled back again, her mouth dropping open with some pleasure before she collected herself. “You know what, I don’t know that you won’t be able to take whatever we’ve got to throw at you, I just wanted… ya know… to look out for you, make sure you knew what you were getting into, maybe keep you a little extra for myself, I dunno… ohgod, I’m so close, please, please, please, harder, fuck me harder, please…”
I kissed her kindly, and I obliged her. While it felt fucking amazing to have her in this position, for a moment there, I couldn’t help but feel a little warm inside at yet another unexpected reminder of how much I loved the friendships I’d made along the way. Sasha and I, we hadn’t even spent that much time together this year, and yet the time we had spent together had been enough to forge a bond of friendship that I rather enjoyed. We were both on the geeky side, we both loved to indulge in our playful sides in life and in bed, and though we weren’t what I’d call close close, we were close enough that I could call her a friend, and that it felt decidedly wholesome that she was looking out for me even in those moments when we were both as compromised as we were just then.
So, yeah, when she asked me to fuck her harder, you’d better believe that I was going to do exactly as she asked. I braced my feet against the ground, held onto her tight, and I pumped up into her clutching cunt with every bit of passion that I knew she would love.
This was enough for Sasha, it seemed, to go right over the edge, as her orgasm hit her all at once, devastating and hard and beautifully loud. Her cries of pleasure echoed through the mirror maze, her body clenching and shaking uncontrollably against the mirror so intensely that I once again feared that it might give way, but it didn’t. The mirror held strong, every bit as strong as I could manage to hold myself, keeping Sasha upright as she rolled through her messy, intense orgasm, before melting against me.
Smiling giddily, Sasha kissed me excitedly, grinning broadly. “Thank you, thank you, thank you!”
I’d slowed my thrusts at this point, but a delayed gratification was all the more worth it to see her looking so fucking pretty. “No problem… glad that felt good… certainly looked good.”
“I like not having to hold back,” she admitted, kissing me sweetly. “And I’m liking that no one’s come looking for us yet… there’s a little more I’d like to do while I still got you so hard.”
Well, I didn’t hate the sound of that. “Oh yeah?”
“Mhmmm…” Sasha purred, kissing me again, then leaning in to whisper in my ear. “You still keep that little bottle of emergency lube in your pocket?”
“Yeah,” I replied, continuing my slow thrusts into her. “Never… leave home without it.”
“Mmm, good…” she continued, looking up at me with a playfulness that seemed quite dangerous. “Because… I want… I want you to fuck my ass…”
Now, I wasn’t a big fan of pulling out in the middle of a good, messy fuck, but an invitation like this was something that could definitely get me there. Quickly, I slid my cock out of Sasha, dropping her leg and letting her get both feet on the ground, wobbly though they may have been. While I bent over to fish into my pocket to pull out my emergency bottle of KY, Sasha turned around and bent over, bracing one hand against one of the mirrors while reaching back with the other to grab one of her ass cheek, parting it just enough to show me exactly where she wanted me to put my cock.
I looked at her puckered pink hole with no small amount of interest, especially when she began flexing her ass invitingly, giggling and teasing me as she looked over her shoulder at me.
“Come on, Ryan… you’re supposed to show me a good time tonight, right? And I think the perfect cap on this good time is you fucking my tight, sweet asshole,” Sasha said, her voice lilting and teasing and thoroughly enticing.
I looked on at this perfectly filthy sight and won’t deny that I was given some pause. Sasha had a magnificent ass, and with skin as pale as hers naturally was, her pink hole was shown off nicely, particularly as she flexed and winked it at me. I didn’t let the pause last long, however, as I soon had my cock lubed up in what might have been a record time, before dropping the bottle and lining myself up behind Sasha.
“Ready for this?” I asked.
“Always,” she giggled, continuing to look back at me hungrily.
It was only the tightness of Sasha’s asshole that prevented me from ramming it in all at once, not that she wouldn’t have been game for that. I gave her a little back and forth pressure, rocking my cockhead against her asshole, but as accomplished a cheer slut as any of the other girls on the squad, Sasha soon had no difficulty taking my cockhead into her tightest hole with the help of enough lube. She cried out, a sharp sound of pleasure and pain, flashing eyes at me that demanded more and would not be very patient in this matter.
Though the going was tight, our will to see this through was strong, and I continued sliding my cock into her tight, hot, gripping asshole until I was balls deep inside of her. Sasha groaned, a deep, guttural sound, quivering as she felt my length inside of her once more. Now with both hands braced against the wall, she dropped her head, catching her breath while I shivered and held my position, holding onto her hips.
“Mother… motherfucker,” she laughed to herself, still quivering. “Oh, fuck… fuck, that’s a lot of cock… so fucking much cock in my ass…”
“Too much?” I asked, squeezing her hips gently and pulling out ever so slightly, rocking back forward until I was buried completely within her again.
Throwing her hair over her shoulder so she could better look at me, Sasha laughed, “Not on your fucking life… come on, fuck my ass, Ryan… show me a good time…”
I smiled back at her, playfully spanking her ass. “Oh, I’ll show you a good time… not sure how long a good time, but I’ll show you one…”
She laughed again. “I’d say about ten inches long…”
I spanked her again, thrusting into her with an increasing pace. “I meant-“
“I know what you meant,” Sasha moaned in reply, pushing back against me. “You’ve been very good, and very patient… you just keep fucking me… fucking use my ass… I know it’s good, so perfect and cute, you just do whatever you want, and cum in me whenever you want to… feels so good… so fucking good… give it to me nice and hard, please?”
I nodded, and at her encouragement, I threw out any restraint and I fucked her ass. Hard. With her cries and yelps and moans of pleasure, with every dark little piece of encouragement she offered me, I gave it to her harder and harder. I’d had this pressure building up in me the entire night, needing every bit of restraint I had not to mess anything up in public, and to make sure that I gave Sasha the good time I’d promised her, and now that I didn’t have to hold back anymore, I didn’t. I pumped in and out of her asshole at an almost violent pace, taking my pleasure from her as she whined and moaned and cursed and pushed back against me harder. I looked down at her, taking in her beauty, and then in the mirrors that surrounded us, taken by the surrealness of the situation and wanting to make sure I’d burned this moment into my memory.
“Oh, fuck, fuck yes, fuck me, fuck me harder, Ryan!” Sasha squealed.
“Yeah, you like that, don’t you? You like me fucking your ass this hard?” I grunted back, spanking her again.
SMACK!
With another high whimper, she replied, “Fuck yes! God, I want you to fucking destroy me!”
“Yeah?” I asked.
“Yes!!!” Sasha proclaimed, arching her back to better push back against me as I fucked her. “Come on, fuck me, fuck me so hard I’ll have trouble walking, come on, give it to me, Ryan! Paint the insides of my ass with your cum, come on, do it, give it to me, cum in me, fill me up!”
“I’m getting there… gonna cum in you soon…” I warned.
This only seemed to drive her even more wild, her moans taking on a higher, whinier quality as she looked back at me. Sasha’s face was a mask of lust and raw animalistic need, and yet even that couldn’t stop her from smiling. Even when she was lost in the throes of sex, Sasha couldn’t help but being that sweet, fun-loving, even goofy beauty that I couldn’t help but feel an intense fondness for whenever we were together.
It was looking at her like this that finally set me off, I think. Having completely lost control, I groaned, loudly, burying myself deep within her ass and surrendering to the inevitable. My orgasm was hard, and intense, as pleasure from this lovely little date night coalesced and exploded all at once. It felt like I had to have absolutely flooded her ass with cum, a sensation Sasha seemed to agree with as she cooed at me.
“Oh god… I can feel it… I can feel it! There’s so much cum…” she giggled, wiggling her ass against me.
Needing some support, I leaned down into Sasha, catching my breath and coming down. She pressed back into me, turning her head to better meet me, kissing me tenderly on the lips.
Looking for something to say, I chuckled weakly, “So… everything you were hoping for… in a date night?”
“You could say that,” Sasha giggled, kissing me again. “Though get me off again while you’ve still got your cock up my ass, and I can give you a firmer answer than that…”
I laughed with her, reaching a hand down between her legs and finding her clit. In no time, I had her moaning, well on the way toward another orgasm of her own, something I couldn’t wait to see and feel.
Though I knew that the longer we spent here, the more we were pushing our luck at being caught, I thought we could handle just one more indulgence like this tonight. Of course, I also knew that with how hot and horny we’d gotten, we were done with the carnival for the day, and would be heading back to either my place or hers to keep the party going, an outcome I couldn’t say that I was opposed to.
Looking into Sasha’s eyes, listening to her sweet moans as I brought her closer to the precipice of another orgasm, I found myself laughing and thinking that I really had to send a thank you to Peter for asking me to fill in tonight.
Comments
JF
I love the setting and the creativity here!
