(Usual Disclaimer Time: All the characters in this story are 18 years old or older, and since we’re living in the wide wonderful world of porno-land here, where clichés roam free and things might get a little unrealistic from time to time, please remember it’s all in good fun.)
(Author’s Note: This story requires a little explanation before we get too deep into it. Book Club Memories is a much-requested spin-off tale from my vaguely epic story Senior Year Memories, taking place between chapters 40 and 41 of that tale. All of you who have read that far in the story will hopefully enjoy the continuation of various storylines, but as for the rest of you, I want to let you know now that it is NOT necessary to be a Senior Year Memories expert to enjoy this story. I’m doing my best to write it as both a continuation, and a story that will stand on its own for your reading pleasure. I hope you all enjoy!
Further, I would like to thank the readers whose votes helped determine some of the action of this story, as well as helping create the character of Mrs. Cassandra Pruitt. As always, I want to give special thanks to fellow Literotica author Lil_kitty for her excellent work as my editor and acting as a second set of eyes on this chapter, and for letting me know what did and didn’t work; if you get a chance, please check out her work and drop some stars if you enjoyed, she writes some very hot and fun stories.)
***
FRIDAY
***
We’d been on the road for about an hour and a half, and by the reckoning of Lauren’s GPS, we’d nearly reached our destination. The suburban landscape of Regan Hills, California had given way a while back to that empty sort of infill you get once you get out of the bigger cities in SoCal, with outlet malls, big box stores and highways as far as the eye could see. A while past that came some semblance of rolling hills and a forest’s edge, with small towns and family farms our new landscape.
Where we were now, though, was just forest, plain and simple.
“Looks like the kind of place you’d film a horror movie,” I mused, looking out the window to see the late afternoon light still somewhat filtering through the evergreen trees. “You know, the kind where a bunch of nubile camp counselors looking to get laid are stalked by a masked psycho from behind the trees with something sharp in one hand and a whole lot of Freudian excuses in the other? I’m not saying that’s definitely going to happen or anything, I’m just noting that… well, that it looks like it *could*.”
“You’ve got one hell of an imagination,” Lauren said.
“I’ve had this accusation thrown at me before,” I admitted.
“And more than that… you need to get out more, Ryan,” she continued, flashing her brilliant, toothy smile. “The world’s not out to get you, and there’s more out there than just city, you know.”
I grinned. “I’d have to convince my dad to buy me a car first.”
My dad had nothing against me driving, and I did already have my license, but he said he wanted to wait for the right moment before getting me a car. I didn’t know what that right moment might be, but, it felt like it was still a ways off.
“Have you thought about getting an afterschool job? Getting a car on your own?” Lauren suggested.
“I have, but with schoolwork and finals up ahead and the school newspaper… I don’t know where I’d find the time these days,” I admitted.
Lauren smirked. “And those are the *only* reasons you don’t have time?”
I laughed. “I mean, my social calendar was a lot fuller this year than I had expected.”
“I’d bet. Mine has also been unexpectedly busy… and I think I have you to blame for some of that,” she said.
“I haven’t heard you complain,” I said, looking at her.
Lauren kept her eyes on the road, but her smile broadened ever so slightly more. “Oh… I would never complain about your attention, Ryan… but let me know if you want help convincing your dad on the car situation. I could always bust some heads, put the screws to him for you.”
“I’m sure you would… but I’ll be fine. I’ll get my car when I get my car,” I said.
“Alright,” she shrugged, “But if you change your mind, again, head busting, I can do it; I’m stronger than I look!”
I smiled, knowing well that she could. Mrs. Lauren McNeil was an old family friend, as she was my best friend, Tori’s, mother, and since Tori and I were pretty well attached at the hip as kids, she was pretty well almost always there for the ride. I’d looked up to her as a surrogate mother figure of sorts at first, in those years after my own mom died, and later she might well have been one of my first crushes. I always knew her as a strong woman, capable of doing anything she wanted to no matter the opposition, and I didn’t doubt she could “bust some heads” if she really wanted to.
At 5’11” (taller when she wore her heels, as she usually did), and very fit for a woman in her early 40s, Lauren was a fairly imposing woman on physicality alone, but when you looked at her and took in her beauty… she could be downright intimidating. Her youthful, gorgeous face with its high cheekbones and porcelain skin could easily light up with her bright smile, or easily break you with one harsh look from her cool, blue-green eyes. Her hair, long, straight and shimmering red, so soft you wanted to run your fingers through it, fell to her mid-back, and was currently tied back with a simple hair tie. As a woman who generally favored casual clothing, or corporate chic, it was interesting to see her wearing something in between these two styles today, with a light blue, knee-length skirt, and a pale yellow, short-sleeved button-up blouse that positively strained over her ample chest.
Yeah, it was hard not looking at her throughout the ride, but given the smiles she shot my way periodically, I knew she liked these glances.
We’d made it for most of the ride like this with small talk and listening to the radio, but now that we were getting closer, it felt like it might be time for some more pointed discussion.
“So… do you guys do this often?” I asked.
“Retreats? Not… not very often,” Lauren explained. “We try to get book club meetings going once a week or so, but long weekend retreats like this we can only usually manage once a year or so. It’s hard getting everyone’s schedules together, and finding a good rental house like this at a decent price…”
Her voice held some nostalgia, and more than a little of something pleasantly darker. Lauren shivered in her seat slightly, her cheeks blushing as her eyes sparkled with a certain naughtiness.
Knowing what I knew about this “Book Club”, that wasn’t all that surprising. I’d come to know a handful of this club’s members over the course of senior year, and had gleaned enough details to know that there was more to this book club than reading a recent bestseller and bitching about their husbands over glasses of rosé.
No, the leader of this club, Viola Kent (mother of another of my good friends, Sarah), had done well over time to evolve the club into something considerably more… unique, I guess you’d say.
Officially, Viola would have called herself a self-employed dance instructor and entrepreneur, running a number of lucrative side hustles out of her home. Unofficially, she was a retired stripper who these days made some serious cash teaching pole-dancing classes and selling sex toys, a side business that had seeped its way into the book club she ran.
What started out as just a new venue to make money had become, in time, a way for a number of the wives and mothers of Regan Hills to get together and fool around with each other, relieving stress and getting laid when those opportunities had proven few and far between.
By what I had been told, I was likely the first man to have ever been invited to one of their meetings, let alone their long weekend getaway. Knowing as many of the ladies who’d be attending as I did, I wasn’t that nervous, but I’d be lying if I said there weren’t some butterflies in my stomach.
“I know I’ve probably asked this a million times already, so if I’m being annoying, I’m sorry, but you’re all certain it’s cool for me to be here, right? I mean, Viola invited me, but I don’t want to be intruding, you know?” I asked.
Lauren laughed, softly. “Relax, Ryan. The other ladies are dying to see you… I think you’re going to be the belle of the ball, honestly. Or would it be beau of the ball? I’m not even sure that’s a thing, but it might be somewhere. Who cares, really… you’re going to be popular. You better be ready, though, you know these are going to be a hard four days, right?”
Now it was my turn to laugh. “I can handle it.”
“You say that now, but you don’t know what these ladies are like unleashed. You’ve only seen some of them before, and one on one at that… get us together, and things can get a little crazy,” Lauren explained, smiling at me with a hint of mischief.
I wasn’t sure if I was meant to be frightened or intrigued by this description, so I asked, “Only a little crazy?”
She rolled her eyes. “Okay, very, very crazy… hot and wet and sweaty and… look, I could try to describe it, or you could see it for yourself. It won’t be that much longer.”
“I guess not,” I said, eying the GPS. The road around us had become a well-maintained dirt path some time ago, and things were beginning to feel quite isolated, but it said we were close to our destination.
“In fact…” Lauren replied, looking behind her briefly before pulling her car over to the narrow shoulder to our right. She turned off the engine, then looked at me. Her breath was increasing ever so slightly, the flush that had started in her cheeks spread as she bit her lip.
“Yeah?” I asked, grinning with anticipation.
“I don’t know how much time I’ll be able to have you to myself this weekend… there are a lot of ladies, after all, who want to vie for your time… what would you say if I suggested we spend a little time in the backseat before we made it to the cabin?” she asked, fluttering her eyelashes at me and smiling a hopeful, vaguely silly smile.
I didn’t say anything, because I didn’t have to say anything.
I stepped out of the car briefly, before reentering through the passenger side rear door. Lauren soon followed, sliding in and sitting next to me. Without a center console between us like in the front seat, there was nothing stopping us from sliding up next to each other. Nothing stopping us from getting a *lot* closer, honestly.
Lauren looked at me, hopeful.
I leaned in and kissed her. Her full lips melded against mine in a familiar fashion, her mouth soft and eager as she moaned against my lips. Her hands, quick and strong, fumbled for my belt and began to undo my pants, while mine soon found their way onto her blouse. When someone like Lauren McNeil wants you to grope her chest, some of the softest, roundest DDDs in the world, you take that opportunity.
So, yeah, I squeezed her tits while we made out, feeling her firm nipples poking through her top as she continued moaning and writhing against me. Finally, I did find those buttons, opening up her top and pulling out her bra-clad tits. The need to see her breasts brought a primal side to me, one that couldn’t be fought easily, and was enough to make me break the kiss.
“Mmm, it’s been too long since you’ve seen these, hasn’t it?” Lauren purred, toying with the heavy-duty clasp at the front of her bra.
Silently, I nodded. She grinned, undoing the clasp and freeing her massive, perfect tits for me. Her nipples stood out rock-hard and begging to be sucked on, and… well, I wasn’t one to pass up opportunities like that, not anymore.
And so I ducked down, kissing and licking and suckling at Lauren’s tits, making her moans take on a higher, more desperate tone as we furiously grabbed at each other. She’d finally gotten my belt undone, then unbuttoning and unzipping the front of my jeans. I could feel one of those swift, strong hands of hers rubbing my large erection through my underwear, her moans now taking on a lower sound of appreciation and anticipation.
“So big… oh, I’ve needed this again… I’ve needed this for so long…” Lauren moaned, finally pulling enough of my underwear down to fish out my very hard, very large cock.
Admittedly, it’s not to everyone’s taste, but having a thick, ten-inch-long cock had made my senior year a lot more memorable than it might have otherwise started out as. I’d been blessed to have found myself with a number of women who were more than happy to play with such a monster appendage, and lucky for me, Lauren was particularly talented when it came to handling such big cocks.
Her hand slowly trailed up and down my shaft, cupping the thick head and running her thumb over it until she could coax out a bead of precum. My lips still wrapped around one of her nipples, I hissed as she began to spread that precum around, that bead soon becoming a steady flow at her instruction as she began to expertly jack my cock. She was good at this… *real* good at this, so good it was taking a lot of restraint to not just let loose here and now. Lauren really knew how to work a cock, and if I did nothing but sit right here, sucking on her tit and letting her jack me off, it would only be a matter of minutes before she had me cumming.
Well, two could play that game.
With a free hand, I reached beneath her skirt, feeling a pair of lacy panties that barely covered her pussy. There was a distinct, moist heat coming from behind them, and Lauren moaned quite lustily at the slightest contact that I made.
I let her nipple pop from my mouth and grinned up at her as I pushed her panties to the side and began to finger her hot, needy pussy. Lauren’s mouth dropped open as she leaned her head back against the seat, moaning and writhing as she rocked her hips against my fingers. I may not have had the decades of experience with sex that she had, but I’d had one hell of a year, and had become quite familiar with how to make a pussy feel good. I explored her outer folds, running light yet firm circles over her clit for a while, before delving deeper and fucking two fingers in and out of her impressively tight cunt, before pulling out and repeating the process again.
I teased her every bit as much as she teased me, toying with her, getting her close to the edge and not letting her cross it. We sat side by side like this for some time, pleasuring each other with our hands while occasionally exchanging deep, lusty kisses as we tried to see who broke first.
This would prove an interesting contest, particularly because this wasn’t the first time Lauren and I had been in more or less this exact position. We knew each other’s bodies well and how to make each other feel deliciously good, but we also knew how to play the long game. I knew she wanted some time where she could keep me to herself before we arrived at the getaway, and I was more than happy to indulge her.
I mean, how could I not?
But even in as ecstasy-inducing a battle of wills as this, someone was bound to break eventually.
“Oh god…” Lauren mewled, whining and looking at me with such beautifully needy eyes. “…if you keep doing that, I’m going to cum…”
“You want that?” I asked, grunting as I did absolutely everything I could to put off my own orgasm.
She bit her lip in consideration, then shook her head. “I need you inside of me when I cum. Please, Ryan?”
She didn’t have to flutter her eyelashes with such a sweet desire to fuck the life out of me to convince me, but it didn’t hurt her case either.
I pulled my fingers from her pussy, and she let go of my cock. Though the backseat of her car didn’t exactly allow for a lot of room to move around, Lauren managed to swing one of her long, shapely legs over mine and climb on top of me. She bunched up her skirt around her waist with an eagerness that bordered on frantic, pulling her panties to the side. I was granted a view of her pussy lips, so pink and wet, framed by her nearly untamed bush of a fiery red that matched her hair. The scent of her arousal filled the car, intoxicating and enough to drive me wild.
I’d more or less been in this exact position before, but that didn’t make it any less exciting to be in this position.
“You’re so fucking hot…” I groaned as she leaned into me, gliding her pussy lips up and down my shaft.
“I know…” she replied, pulling my shirt off and tossing it aside with such force she almost took my glasses with her. Running her fingers down my recently defined chest and abs, she replied, “And you’ve grown into an exceptional young man.”
I leaned in, kissing her. “I like to think I’m still an exceptional work in progress.”
“Whatever you have to tell yourself,” Lauren replied with a chuckle, reaching between her legs to grab my cock, guiding it toward her pussy. “I know what I know…”
I groaned as she rubbed my cockhead against her lips. She was so wet… so fucking hot… I needed her in this moment like I needed air to breathe, and I was well past the point where only a tease would suffice.
I hissed sharply as the head popped inside of her tight cunt, a sound that was soon drowned out by her loud moan. Lauren looked down at me with such want, such hunger, and began to lower herself slowly onto my cock.
Nothing could have held me back from feasting at this point. I leaned in, suckling at her nipples with my hands planted firmly on her ass, squeezing and massaging her as she continued her agonizingly sweet descent down my cock, pleasure flowing through my body as I filled her impressively tight pussy a little at a time. Her moans, her high whines and sharp intakes of air became a symphony to my ears as I continued to ravenously devour her tits.
Finally, she was seated on my lap completely, every inch of my cock buried deeply within me. Briefly there was silence, the only sounds filling the car her ragged breathing, and the sound of my mouth on her tits. Even this was stopped by Lauren when she pushed my head away from her chest, looking me in the eye as we took in this moment.
Ever since the two of us had started fucking around with each other, there had been a distinct intimacy between Lauren and me, and I could feel it now. Here we were, completely and utterly joined, and we couldn’t stop looking each other in the eyes and sharing these slight smiles. Right here, like this, she suddenly looked younger, more alive than she often did back home, and in a moment that might also have been giddy, she leaned in and kissed me, throwing her arms around me to hold me close to her. It was a long, lingering kiss that brought out a warmth deep inside of me, one that only got hotter as her pussy muscles began to squeeze and massage my cock.
She held me there like this for quite a while, savoring this special heated intimacy the two of us shared, enjoying the feel of me being buried deep inside of her… but soon, she began to writhe in my lap. With the most impressively practiced skill, she rocked her hips, slowly bouncing up and down on my cock while building to a pace that I knew would get hot sooner rather than later, because while the two of us did share a certain intimacy, whenever we got hot and heavy with one another, we tended to fuck like maniacs.
Though she couldn’t get very acrobatic considering the limited space we were in, Lauren more than made up for it with enthusiasm as she roughly rode me.
And as she indulged in her rarely used dirty talk.
“Oh fuck, oh fuck, I’ve missed this cock… I’ve missed this big fucking cock… god, I can’t get this at home, I can’t get fucked like this, not like I want, not like I deserve, god, this is amazing… you’re amazing, Ryan, you fill me up, so deep, so fucking hard…” Lauren said, leaning into my face and making sure I had a mouth filled with tit.
I grunted, squeezing her ass and helping her fuck me, making sure she was nice and full while I eagerly sucked at her tits.
Letting her nipple fall out of my mouth for a moment, I said, “You’re so fucking hot… glad we had this time before things get crazy… fuck… you’re so beautiful, your body’s amazing, and your pussy, fuck, how are you still this tight?”
She laughed, leaning down to kiss me before continuing, “I take care of myself, and I take care of you… honestly, we’re all better off when we’re taken care of, aren’t we?”
“You know it,” I grunted, smacking her ass and making her mewl appreciatively.
“Don’t get me wrong… I’m looking forward to meeting up with the others… they can make me cum soooo gooooood… but when you need some cock, and I mean serious cock, and you’re the only serious cock that’s going to be around, well, don’t blame me for being a little greedy now…” Lauren moaned, riding me and smiling down at me with a mischievous grin.
“I wouldn’t dream of blaming you…” I said. “I’m looking forward to meeting everyone too.”
“You mean *fucking* everyone?” she replied, smirking and kissing me.
I smacked her ass extra hard for this one, the sharp sound echoing through the car and making her cry out in mixed pain and ecstasy.
“That too…” I grunted, feeling my balls start to swell. “Fuck… you keep going like this, you’re gonna make me cum.”
“That was the idea,” Lauren laughed, riding me even harder. “I’m so close, too… come on, hold on just a little longer, Ryan, let me have that big cock a little longer… make me cum… come on, keep fucking me, keep fucking me, harder, harder, like that, make me cum, make me cum, fuck, I’m almost there, keep going, keep going, FUCK, MOTHERFUCKER, I’M CUMMING! I’M CUUUUUUMMMMMMMMMING!!!!”
As usual, Lauren was quite vocal when she came, but when she came against me this time, there was a particular strength to it I found impressive. Her gushing pussy clamped down on me, milking my cock as she wrapped her arms around me, shuddering and shaking violently with her own orgasm. I held her close, but with the bliss of her exquisite orgasm massaging my cock well past the edge of what I could handle, I couldn’t hold back any longer. I thrust deep inside of her, cumming and cumming hard, filling her clutching pussy with what felt like a pent-up gallon of cum.
Our bodies alight with pleasure, we writhed against one another for a good, long while, holding each other close and catching our breaths as we tried to hold onto this moment for some time. I looked into her beautiful eyes, grinning at the way her cum-addled state made her smile in a pleasantly goofy way.
I couldn’t help myself but lean in and kiss her, to which she kissed me back eagerly. This first kiss was fiery, followed by shorter, more tender kisses.
When we finished kissing, I looked at her fondly, brushing some of her red hair behind her ear. I’d known Lauren McNeil for so long, and felt a fondness for her that nearly overpowered me. I was beyond happy that we had had this moment to share before things really got crazy, but I couldn’t deny that I was looking forward to some of that crazy adventure as well.
Sighing, I said, “I think we should really hit the road soon. They’re gonna wonder where we are.”
Rolling her eyes, Lauren answered, “I guess… but that was really, really fucking fun…”
“Yeah,” I agreed, laughing. “Yeah, that was really good.”
Climbing off of me, she chided, “But you better not have used up all your energy here! A whole bunch of my friends are going to be there this weekend, and they’re going to need that dick too!”
Chuckling softly, I replied, “I’m 18-years-old and gonna be spending a weekend surrounded by gorgeous MILFs, I’m gonna be fine… I’m gonna be just fine…”
I didn’t add ‘I think’ to the end of that sentence, because I wanted my bravado to cover any lack of confidence I might have had, and thankfully Lauren was nice enough not to draw any attention to any shaky enthusiasm I had.
Don’t get me wrong, I was greatly looking forward to a long weekend away with gorgeous older women, but at the same time, I was a realist.
Enthusiastic as I was, I knew I had my work cut out for me.
***
So, right around this time, I’m imagining anyone reading this is having one of two responses.
1) Who the fuck is this guy and why’s he so familiar with fucking his best friend’s mom?
or
2) Hey, Ryan, finally glad you’ve made your way around to meeting up with the book club!
If you’re in the latter camp, you’re probably familiar with the adventures I’ve been having during my senior year of high school, my “Senior Year Memories” as one of my closest friends dubbed them, and I probably don’t need to tell you who I am.
If you’re in that former camp, though, I guess some quick introductions are in order. I mean, I could’ve started out this way, but so many of these stories kinda start with the lead character introducing themselves and describing themselves and how hot they are, and it can get repetitive, I thought a little of the good old “in media res” would keep it exciting and interesting.
If it wasn’t, sorry, and if it was, then, yay me, I did something right.
So, right, before we get back to the action, it’s introduction time…
My name is Ryan Collins, and I turned 18 just before my senior year of high school. If you’d have asked me at my sparsely-attended birthday party, I would have told you I was a boring, skinny, 5’11” nerd who looked so plain he’d never stand out in a crowd, who lived in the most boring town on earth: Regan Hills, California. As a town, it looked like suburbia from an 80s movie, albeit a suburbia that had seen slightly better days, and while I might have noticed that our fair town seemed to have a disproportionate number of gorgeous women with unusually impressive assets, I never thought that would mean anything to me. After all, I was a dateless nerd, and even if I had a huge cock, it wouldn’t matter to my senior year. The life I lived seemed like it’d be the life I would always live, with nothing changing, and while that wasn’t exciting, it was something I’d learned to accept.
Through a serendipitous series of events that rely on a lot of cliché, suspension of disbelief and porn logic, one of the popular cheerleaders at school, Kaitlyn Pruitt, found out about how big my dick was, and just as quickly, I wasn’t a virgin anymore. Then she told her friends, and their friends told their friends, and suddenly I was having a lot of sex with a lot of girls at school… and I was in fucking heaven.
The year wasn’t always great; I dealt with some trouble, heartbreak and pain (both physical and emotional), but I also found myself in the best shape of my life, with two hot girlfriends I loved more than anything, and had more friends than I knew what to do with anymore with all the girls I’d met this year.
One of the most curious developments of the year, though, had occurred with the women I’d gotten together with who weren’t my classmates… as I had gotten together with a handful of teachers, and my friend’s moms. I’d found a number of older women in Regan Hills to be desperate for love and attention that they weren’t getting at home, and I was more than happy to provide it when the opportunity arose.
What I hadn’t anticipated, though, was that a lot of these women were friends. I hadn’t known about the book club, or that in time they might set their sights on me and want me to attend one of their meetings, let alone one that was going to be considerably more than just a casual get-together. By the time I’d been invited to make a special appearance at their annual weekend getaway in early March, I’d learned to go with what life threw at me and see where adventure called.
That’s probably enough introduction, yeah? Why don’t we get back to previously scheduled erotica, currently in progress…
***
It was less than a five-minute drive to get to the lake house once we’d fully dressed and more or less got ourselves back to some semblance of looking normal. There was no way we could actually pass for normal, but, this wasn’t exactly going to be a weekend where that would matter too much.
From the outside, the rental house itself was impressive, two stories and expansive, with a style that made it look at once modern and like a rustic lodge. It sat in its own little patch of clearing in the trees, the afternoon shimmer of the lake beyond just visible in the distance. A gravel driveway separated the dirt road from the house itself, leading to an open garage and a parking lot-like area, where there were already three cars in place.
“We’re late,” I said.
“Actually, we’re pretty early; a lot of the ladies won’t be able to show up until tomorrow or Sunday,” Lauren explained as she pulled over to the side of the parking area. “Viola’s definitely already here, as for the others… I didn’t get a good look at their cars, but I’m sure we’ll have a fair bit of company tonight.”
She shuffled around in her seat slightly, licking her lips without clearly thinking about it. I knew that she was familiar with a lot of the ladies of the book club, but I thought then that I was about to find out just *how* familiar she actually was with them.
Lauren parked her car, and I was glad to step out of it. I was never one who did well with really long car rides, and though the company was great (and our brief detour even better), it felt good to stretch the road out of my system. It was a nice day, feeling reasonably warm as it usually did here in Southern California and with a feel to the air that said Spring was right around the corner.
Lauren soon joined me in stretching, looking far more graceful and put together than my random grunting and flailing about, before she headed over to open the trunk. I joined her around the back of the car, picking up my backpack (which looked fairly insignificant when compared to the large bag she’d put together for the weekend) and a couple of the reusable grocery bags full of food that she had stashed away. It seemed like a lot, but given how there were supposed to be eleven of us here this weekend… I guess it was better than going hungry.
I was about to make some inane joke about her having bought enough to feed an army, when I was cut off by the sound of a very familiar voice calling out to us.
“Lauren! Ryan! I’m so glad you two could make it!” she called out to us.
My heart skipped a beat as I set down the bags, and turned to face Ms. Viola Kent.
Viola was the single mother to one of the best friends I’d made this year, Sarah, a sweet, blonde band geek with dreams of being a cheerleader. With some persuasion, I’d talked Sarah into trying out for the squad, and being one hell of a dancer, and now she was living the dream as part of Regan Hills High School’s cheerleading squad. It was as our friendship (both in and out of the bedroom) grew, that Sarah asked a favor of me, and wanted me to seduce her mother. After all, Viola was a woman who worked so hard and barely dated, and Sarah only wanted her happy… it seemed a crazy favor at the time.
Until I saw Viola Kent, anyway.
As it happened every time I saw her, when I saw her walking toward us across the gravel parking area, I was convinced that Viola was one of the most gorgeous women on the face of the Earth.
For a woman in her early 40s, she easily looked about fifteen years younger. With soft brown eyes that I knew hid a playful, energy, currently hidden behind a pair of sunglasses, lightly tanned skin, and a casual grin peeking through her delicious lips, her face held a beauty that always captivated me. Her head was cocked back slightly, giving her ruby-red colored lips and daintily pointed nose time to shine, while her long, raven hair cascaded around her bare shoulders. In fact, a lot of skin was on display on her 5’7″ frame, since she seemed to be wearing not much more than a black bikini top and a colorful, ankle-length sarong that only hid one of her shapely legs. Her fit, dancer’s body was on good display, with the sarong hugging her hips and nice ass well, and while the bikini top didn’t show much of her pert B-cups, it was hardly what I would call conservative.
My jaw was known to drop in her presence, and I don’t think this time was any exception.
“We’re glad to see you, too!” Lauren practically squealed, bounding over to Viola and wrapping her arms around her in a hug, before looking back at me. “Well, I know *I’m* glad to see you; it seems Ryan might have forgotten what words were.”
“I tend to have that effect on young men,” Viola said, smirking at me before looking up and planting a kiss on Lauren’s lips. If this kiss was a surprise at first, Lauren soon leaned into it, kissing Viola back deeply in a way that might well have made both of them moan just so slightly.
This was just enough to snap me out of my confusion. “Oh, uh… hi, Viola.”
“Hello yourself, Ryan,” she said, breaking the kiss with Lauren. “I see you two couldn’t wait until you got here?”
I’d have asked how she knew what we’d been up to, but it was better not to underestimate Viola.
I shrugged. “Sorry.”
“It was my fault,” Lauren said, blushing. “I couldn’t help myself… and I got a little greedy. You know how it is. I swear, I didn’t wear him out; he’s got enough in the tank for the whole weekend”
“Oh, I do know how it is,” Viola purred, reaching down and swatting Lauren on the ass hard enough to get a good SMACK sound.
Lauren yelped. “Hey!”
“Oh, come on, you know you love a good spanking, and that by the end of the night that ass is going to be nice and pink,” Viola replied, looking at me with a smirk.
That was an image that got me hard again.
Lauren blushed, then looked around almost as if she wanted to say “not in public”, but since we were in the middle of nowhere, that would have just been silly. Instead, she said nothing.
“The others are inside already?” Lauren asked.
Viola nodded. “Yeah, Cassandra, Brenda and Valerie are already here. They’re it for the night as far as I know, but we’ll have more coming in tomorrow.”
An eager smile crossed Lauren’s face. “Well, I think I should go inside, then…”
“Do whatever you want; I’d like to borrow Ryan for a minute, first,” Viola said.
“Sure,” I said.
Before Lauren could add anything else, Viola interjected, “And when I say a minute, I mean it’s just going to be a minute. Don’t get those very wet panties in a bunch; I’m not going to tie him up in my room and lock him in there all weekend for my own use… though that might be fun. We’ll head on in soon.”
“Alright,” Lauren said, picking up some of the grocery bags and sauntering away. “But if you need a rescue, Ryan… you know who to call for!”
The way Lauren’s beautiful ass swayed as she walked, I knew she was putting on a show for Viola’s and my benefit.
Viola chuckled softly once Lauren was out of earshot. “Ah… this *is* going to be a fun weekend, isn’t it? Oh yes, it starts out all cuddles and orgasms, but then the claws come out, and things get *really* interesting…”
Looking her over, I looked for something profoundly interesting to say to Viola, and instead settled on, “You look amazing, Viola.”
“I always look amazing,” Viola said, tossing some of her hair behind her head and smiling brilliantly. “But I do feel exceptionally good today. Thank you. You’re not looking too bad there yourself, Ryan.”
“Thanks,” I replied, looking down, a little embarrassed. As a guy who still viewed himself as a tall, skinny nerd in glasses, it took some reminders sometimes that I’d put on a fair bit of muscle this year, and wasn’t half bad to look at anymore.
“Though, if I might offer a suggestion that might make the weekend go a bit easier…” Viola said, her voice confident and calming.
“Of course, what is it?” I asked.
She looked me up and down, not quite hungrily, but with a certain avid curiosity in her eyes.
“When it comes to our weekend getaways like this, I want to make it clear that it’s not a constant, multi-day-long orgy. There’s a lot of us just hanging around, relaxing in each other’s company, with the sex completely casual and always agreed-upon between us. I want to make it clear that there are no expectations, and if there’s anything you don’t want to do, you don’t have to do it, and if you’re worn out, you can crash whenever you want,” Viola explained.
“Thank you,” I said, more relieved than I expected. “That’s good to know.”
“However…” she continued, reaching out to me and touching me on the shoulder. “If you are game for some action soon, I’d recommend a change of clothes. Easy access is kind of the name of the game around here, and in those moments in which you are dressed, might I recommend not wearing any more than you have to? I’m sure you have some swim trunks in your bag, and if the weather holds, that shouldn’t be more than you need, right?”
That sounded fair, and the way she was touching my shoulder, I took her meaning quickly. I pulled off my shirt, tossing it on top of my bag, and stood shirtless before her.
“Better?” I asked, enjoying the way Viola looked at my chest, abs and arms.
“Much…” she said, reaching out and touching my chest and making an appreciative, purring-like sound.
Showing her that two could play that game, I did the same, reaching out and squeezing her left tit through her bikini top, then sliding my fingers beneath beneath. Her firm breast felt absolutely amazing in my hand, her nipple boring into my palm, and when she started to moan softly, I pulled the fabric of the cup underneath her breast and exposed it to the world.
“You’re right, easy access does have its charms,” I said, loving the look of her bare tit and how firmly her nipple stood out.
Smiling devilishly, she said, “You have no idea…”
For emphasis, she pulled the opening of her sarong to the side, exposing her shaved pussy to me. It was a fleeting glance, but enough to show me that she was quite excited, and already glistening.
“You’ve been busy,” I said.
“I have,” Viola purred.
“With whom?” I asked.
“Oh, where’s the fun in kissing and telling?” she laughed, softly, covering herself up. “Ah, I am so excited for you… there is absolutely no way you can know what you’re in for. Not yet, anyway… but there is a fair possibility we might destroy you this weekend,” Viola replied.
“I can take it,” I said. “I’ve been destroyed before. Ask me about New Year’s sometime.”
“We’ll see, we’ll see…” Viola said, turning around on her feet and slowly walking back toward the house. “We might have a few chores that require a man’s touch for you before we get settled in for the night, think that will be a problem?”
Picking up the remaining bags from where I’d set them by Lauren’s car, I caught up with her and said, “No, no problem at all…”
***
The interior of the house was spacious, and every bit as simultaneously modern and rustic as its exterior. Though Viola let me inside, she soon peeled off to do her own thing. I didn’t know the layout of the place yet, I didn’t even know where I’d be sleeping yet, but I was here now, and I was going to enjoy every minute of what this long weekend would hold.
After getting lost a little in my search for the kitchen, I soon found the dining room, and then followed the voices from there toward the kitchen.
Well, one voice really, accompanied by some occasional moaning sounds.
“All I’m saying is, you may not have fun cooking, but I have fun cooking; it’s all a matter of perspective. It’s not all just about throwing the right things in at the right times and hoping it comes out well enough to be enjoyed by our indifferent husbands and kids, it is science! Creation! Mastery of the periodic tables and showing our dominance over primordial forces that once seemed magic to our earliest ancestors. To them, I would look like a wizard! To myself, I am simply a scientific explorer navigating the treacherous waters of culinary insight, and hoping to bring some joy to the world!” the speaker proclaimed, her voice familiar in her enthusiasm.
Her audience, on the other hand, just kept moaning softly.
I peeked inside the kitchen, finding the source of the voice: Dr. Valerie Chan, one of Regan Hills High School’s finest science teachers.
At 32 years of age and 5’2″, she was a favorite of many students because of her boundless enthusiasm for science and teaching, and was a favorite of the rest because she was fucking hot. While short in stature, the Chinese-American beauty was utterly stacked, with a round, bubble butt and D-cup tits. Her shoulder-length, silky black hair framed a face that was used to joy, with full lips often held in a broad, toothy smile, and dark eyes that easily expressed her enthusiasm. Unlike Lauren or Viola, I hadn’t actually screwed around with Valerie before, but I wouldn’t have minded it at all, and I’d heard through the book club grapevine that she was interested in me.
Looking at her now, I could barely restrain myself from drooling. She wore a pair of tight, cutoff jeans that barely covered her entire ass, and a tight t-shirt that was cut off so high underneath her tits I saw a fair bit of underboob. I could see quite a bit of her pleasantly-tanned skin, enough to make my cock twitch firmly in my pants.
She was putting groceries away in the kitchen, unmindful of my presence and looking utterly luscious as she reached for shelves and stashed things away.
She was also quite good at ignoring the two women making out on the other side of the kitchen. A blonde woman with a great ass and big tits, wearing nothing but a purple bikini, had Lauren pinned to a kitchen cabinet and was kissing and groping her big tits passionately. The way she moaned, Lauren was very much into this, about as much as I was into the show itself. These two seemed in a world all their own as Valerie continued on enthusiastically talking about cooking and science, leaving this a perfect image by my estimation.
It wasn’t one that could last forever, not if I wanted to finish my chores.
I cleared my throat.
While Lauren and the blonde didn’t stop for even a second, Valerie turned to see me and started, bringing her hand to her chest in surprise.
“Ryan! Fuck!” she laughed, “You nearly scared the shit out of me.”
“Sorry! Wasn’t my intention,” I laughed, stepping out of the doorway and into the kitchen. “Just came to drop off some more groceries.”
“Please, please, bring ’em right over here, I’m working on creating a system, and once that system’s in place, you can bet your ass I might actually know what I’m doing,” Valerie laughed.
It was after this laugh that she looked at me, and I mean *really* looked at me for the first time, and I think I saw her breath catch in her chest. Having her friends describe the times we had together was one thing, but no doubt Valerie still viewed me as one of her skinny, nerdy science students. This view seemed to give her pause, then the corners of her smile turned upwards appreciatively.
“My, my, my… let me get a look at you…” she said, coming over to me, then taking the grocery bags and my backpack from my hands and setting them on the floor. Looking at my muscles, she asked, “May I?”
“Be my guest,” I said.
“Thanks!” Valerie replied, perky and enthusiastic, as she ran her soft fingers over my arms, squeezing gently, before working her way across my chest, then down my stomach to my groin. My erection was quite prominent even through my jeans, and she rested her hand on it gently and squeezed.
“Oooh, this is nice… very, very fucking nice… these girls aren’t lying, and you’re way bigger than my husband, though, don’t tell him I told you,” she continued, her tone mischievous as she batted her eyes at me playfully.
“Since I have no idea who he is, that shouldn’t be a problem,” I responded, looking down at her impressive chest and smiling.
“Oh, where are my manners, you wanna see my boobs? Most of the boys at school want to see my boobs, I hear. None of them have yet, so you’d be the first,” Valerie continued, quickly.
“A lot of the girls wanna see them, too,” I explained, before nodding. “And, yes please.”
“You got it!” she exclaimed, giggling and quickly pulling up her top.
Her D-cups were truly impressive, as tanned as the rest of her and with no tan lines (which raised a lot of fun questions), with prominent, very suckable nipples. Had she not dropped her top at that moment and re-covered them, I might have done something to her then and there.
“Just a tease, for now!” Valerie continued, enthusiastic as always. “We’re going to see plenty of each other later, and I’ve wanted to see plenty of you for a very long time now… but when you’re in the kitchen, a little clothing is generally a good idea for safety, not that I can convince Brenda over here…”
“Okay, I’ve been distracted long enough,” a pleasantly sultry voice said from across the room as the blonde finally disentangled herself from Lauren, then turned around to greet me. “Hello, Ryan.”
Grinning, I said, “Hello, Mrs. Lynn.”
Mrs. Brenda Lynn was my AP History teacher, and easily my favorite teacher in school long before the two of us had started having sex. In a roundabout way, she sort of started my crazy year by convincing me to tutor Kaitlyn. It wasn’t long before Brenda found out about how Kaitlyn and I started having sex, then seduced me herself and… well, now I was here, and all the more fortunate for it.
At 5’3″, Brenda looked stunning for a woman in the later end of her thirties, with a faintly pale, soft-skinned and toned body that most porn stars would kill for shown off amazingly in her bright purple bikini. Her wider hips held a pretty epic ass, while her beautiful, round, DD-cup tits were barely held in by the small bikini top. Her face, friendly and pretty, still held my attention most. Her blonde hair, cut in a bobbed haircut, framed beautiful blue eyes and a bright smile. While I’d gotten used to her looking tired in the beginning of the school year, ever since we’d started screwing around, there was a certain spark to her that I just couldn’t get enough of.
“Hello, Ryan…” she said, striding toward me with a purpose. “I know you’ve probably heard this a bunch already, but thank you, so much for coming…”
Before I could get in a word edgewise, she threw her arms around me and pulled me in for a passionate kiss, almost as if claiming me in front of her friends. I guess since she got a lot of this year started for me, she did have a little more claim than most. It was a deep kiss, one that curled toes and excited parts of you you never knew could be excited. Brenda crushed her body against mine, her nipples hard through her bikini top pressing into my bare chest, before she broke the kiss just as abruptly.
“It’s… wow… it’s, ummm… I’m happy to be here,” I said.
“Gee, go and hog him all for yourself, why don’tcha,” Valerie said, rolling her eyes.
“I tried that first,” Lauren interjected with some amusement. “But *I* remembered how to share.”
“No doubt after you drained his balls,” Brenda replied, reaching down and cupping my package. “Thankfully, I know you’re good to go pretty quick. That’s going to come in handy this weekend.”
“I imagine it would,” I said, licking my lips and looking down at her. “I’m definitely not going to ignore you.”
“You’d better not,” she replied, pulling me in for another quick kiss, before adding, “You have a room for the night?”
“Not that I know of,” I replied.
“Lauren and I are sharing a king-sized… I’m sure we could squeeze you in tonight,” Brenda said.
Lauren nodded. “Better to grab you now, especially when these other ladies’ll probably want you on other nights.”
“I’d like to do more than grab you now…” Brenda said, squeezing my cock through my pants.
“We all know what you’d like to do to him,” Lauren said, amused and rolling her eyes.
I smirked. “I… well, I’d like to do something with you right now, but Viola put me to work; I carried in the groceries, she wants me to take in the firewood bundles from in back. Then I can be all yours.”
“You better hold to that,” Brenda called after me as I turned on my feet and walked toward the sliding glass doors that led to the rear of the house.
I slid one open and stepped outside, and for the moment, took in what you could easily call majesty. In the distance, the forest and shimmering lake looked utterly gorgeous, with not another soul in sight for miles by the looks of things. However, since the great outdoors and I didn’t get along the best, I also had the option of taking in the house’s expansive pool area, with an impressively sized pool, hot tub and barbeque nook… yeah, I could definitely imagine some debauchery occurring here.
“Ah, you’ve made it, at last!” a playful voice called form beside me.
I knew that voice. I’d know that voice anywhere. I knew she’d be here, and still I felt my heart beat a little heavier at the thought of her presence.
I gulped, turning to look at the woman stretched out on one of the pool’s deckchairs, and said, “Hello, Mrs. Pruitt.”
She laughed, softly and replied, “Please… it’s Cassandra! For how long we’ve known each other, this weekend, it’s Cassandra!”
“Sure… Cassandra,” I replied, trying to figure out just what exactly I was feeling about this.
Of all the women here, 37-year-old Cassandra Pruitt was probably the one I’d known for the longest. By sheer virtue of her and my dad working at the same company when I was very little, she became a family friend, and since her daughter, Kaitlyn, was my age, I’d often be sent over to play at her house when Dad was working long hours on one of his many other projects. For a while, Kaitlyn and I were friends, but when puberty hit and she became popular (and bitchy), we’d gone our separate ways. Since Kaitlyn and I both turned 18 and reconnected this year, I’d not had many chances to see Cassandra again, except in the occasional comings and goings at Kaitlyn’s house.
Looking at the woman lounging on the deck chair, I had the opportunity to remember exactly why she was one of my earliest crushes.
Even at her age, she could have been mistaken for Kaitlyn’s sister. At 5’4″, this pale-skinned and dark-haired beauty wore a black, silk robe that barely went down to her mid-thighs, and even with the help of a belt was having a tough time holding in her impressive curves. Firm, long legs led to wide hips, and if she parted her thighs even slightly I’d no doubt be able to tell whether or not she was wearing panties from here. Her DD-cup tits strained the top of the robe, allowing me to see a fair expanse of cleavage that came close to making my mouth water.
Her beautiful face bore a fair bit of amusement as she observed my thunderstruck appearance. With shoulder-length, silky black hair cascading around her face against the chair’s pillow, she looked up at me with big brown eyes behind a modest pair of sunglasses, her full, pouty lips, painted a bold red for the occasion, curled into a shining, smile as she tilted her pointed chin in my direction.
Finally breaking the awkward silence, she continued, “You know, for how frequently I’ve seen you around the house recently, I have to admit, it’s surprising that we haven’t had much more of a chance to catch up.”
“Oh, uh, yeah. Sorry about that,” I said.
She laughed casually, giving off the cool-mom vibes I’d always enjoyed when I was a kid. “Don’t worry about it. After everything I’ve heard from the others… well, I understand you’re having a busy year. Not a lot of time to slow down and catch your breath, right?”
Calming slightly, I smiled. “Not really, no. I haven’t been trying to avoid you or anything either, I swear, but… well, I gotta admit that this isn’t exactly how I expected to talk to you in any proper capacity either.”
“It can be a little awkward, can’t it?” Cassandra proposed.
“A little, yeah,” I replied, happy that she understood.
Seeing that this might take more than a moment, I sat on the edge of a chair close to her.
“Well, you don’t need to worry about me. When I’m here, I’m just here to chill, and I have no intentions whatsoever of adding more stress to anyone else’s day… I’m here to relax, and… well, you know what we book club girls do when we get alone…” she suggested, her lips staying curled in a rather playful smile.
“Drink wine, talk shit about your husbands, screw around with each other, and maybe, occasionally, actually talk about a book on occasion?” I suggested, finding it suddenly easier to look at her, wondering just what, if anything, she was wearing beneath that robe.
Cassandra laughed. “Ah, so I see you’ve been told *exactly* how things go around here.”
“I have,” I said, eyes darting back to her face, then back to her body. “I don’t have a husband to talk shit about, but I like to think I can keep up with all of you on the rest of it.”
“I’m glad you think you’re that capable,” she replied. “I’ve heard from some of the others about just how capable you are, and I think I’m willing to find out for myself at some point, if it wouldn’t be too weird for you, but the confidence is nice to hear… it wouldn’t be too weird for you, would it? I know what you and Kaitlyn do in your free time, and I wouldn’t want to interfere with that, or make things awkward between you two…”
“It wouldn’t be weird for me,” I said, before amending. “Maybe a little weird, but not in a bad way, I swear. But a little weird can sometimes work out pretty great, right?”
“That’s what I’ve come to understand…” Cassandra admitted, looking me up and down, appraising, shifting in such a way that she revealed another couple inches of cleavage. “When I first joined this club, I really thought it was going to be about reading books and talking about them, but once you’ve attended your first meeting… your life will never quite be the same. It was weird for me at first too, now it’s just, well, what we do.”
I nodded, my eyes now lingering on her newly exposed skin. “When… well, when I started seeing Kaitlyn, and she started introducing me to her friends, it was, yeah, definitely kind of weird at first, but, weird became good and normal pretty quick.”
“Then I’m glad we understand each other,” she replied, biting her lip slightly and looking down at the bulge in my jeans. “So… you want things to get any weirder right now?”
Yeah, my heart skipped another beat at this question.
“Maybe… maybe a little,” I admitted.
Cassandra grinned. “Hmmm… I have an idea. This might be a little, this might be a lot, but there’s only one way to find out, isn’t there?”
“What do you mean?” I asked.
“This,” she replied, grabbing hold of her robe’s belt, undoing the light knot she had done at the middle, and then opening the robe up so I could see what she was wearing underneath.
Which, in this case, was nothing.
Her tits were firm and high and looked absolutely enormous in her lounging position, her body toned, and her pussy… fuck, did it look good. A decent landing strip led to full, engorged lips, moist with a faint but distinct dampness that made me smile. I don’t know if she was turned on by our conversation, or if she had been doing something before I got here, but seeing her naked for the first time, only one word seemed appropriate.
“Wow,” I said, my voice shaky.
“Wow?” Cassandra laughed, squeezing her tits before running her hands down her abs, settling them on her inner thighs. “I rank wow… ah, I haven’t heard that from my husband in a while. I like that enthusiasm.”
“Hey, we’ve all said wow about you before!” Brenda called out, approaching us.
I had been ready to take this moment to the next level, and was hard as a brick, so even an interruption as welcome as Brenda and Viola, both of them carrying folded up towels, approaching us brought a bit of a disgruntled growl from me.
“I know, but sometimes you want to hear it out of a young man. Given the girls my daughter tends to accompany herself with fighting for Ryan’s attention, I’m glad to see I can still compete with them!” Cassandra quipped.
“Oh, you definitely stack up,” I said, unable to look away from her naked body.
“I know I want a taste,” Viola said, dropping the towel she’d been carrying at the foot of Cassandra’s chair, then kneeling on it.
The women of the book club all seemed to enjoy their little power games, establishing who was on top and who was the best. I didn’t deny them whatever fun they took out of this, because frankly, well, it was fun for me to watch.
When it came in the flavor of watching Viola kneel down and kissing Cassandra’s inner thighs… well, it was a lot more than fun to watch.
“Ooooh, yeesssss…” Cassandra hissed as Viola’s tongue grazed her pussy lips.
“Mmm, yes, still tasty,” Viola confirmed, lowering her sunglasses enough to wink at me before she dove in and continued eating Cassandra’s pussy.
It was a good show, and Viola knew exactly how to perform for all of her audiences. Cassandra was quite responsive, writhing and moaning in ecstasy as Viola expertly ate her pussy. I could have watched this slow, passionate sex act for some time.
So, of course, this is when my attention was stolen by the sound of a towel being thrown at my feet.
“They could be at this for a while,” Brenda said, leaning down to kiss me again. “And while I like to watch as much as the next person, I’m also in serious need of some of your big fucking cock *right* now…”
The way she looked at me with those “come fuck me eyes”, my cock might have gained an extra inch then and there. I didn’t wait, didn’t hesitate, I quickly fumbled at undoing my pants, then pulled them and my underwear down. My erection sprung free, standing tall, and from between my legs, Brenda let out a slight gasp of awe. It was far from the first time she had seen my cock, but that response still managed to excite me.
I wasn’t the only one excited.
“So… oh god… that’s the cock I’ve been hearing all about?” Cassandra moaned, dropping her head back as she writhed against Viola’s face. “That’s… that’s nice.”
“Wait ’til you feel it inside of you…” Brenda replied lustily, kneeling on the towel she’d dropped between my legs and stroking my cock as if it needed more life brought to it. “I’ve fucked Ryan more times than I can count this year, and I just can’t get enough of him… you’d be doing yourself a serious disservice, Cassandra, if you don’t fuck him before the weekend is out.”
“Maybe…” Cassandra moaned, sounding both interested and a little conflicted. “Fooling around with the rest of you girls, that’s one thing… but we’ve never done anything with guys here… that might be a bit of a line for me to cross…”
Pulling her face from between Cassandra’s thighs, Viola climbed on top of her and pressed her fingers into Cassandra’s pussy. “Hey, we’re all about whatever you’re comfortable with this weekend… but you’d be cheating yourself if you denied yourself what Ryan is capable of. The boy’s not just equipped, he’s something of a genius when it comes to pleasuring a woman…”
“Very…” Brenda replied, now freely spreading precum up and down my cock. “…and so very, very tasty, too…”
Looking up at me with her lips parted in anticipation, Brenda stopped stroking me for a moment. I groaned like a wounded animal, needing her to continue with what had felt so fucking good… and I think this was where she wanted me. She looked up at me, chidingly, as if telling me to be patient and things would get even better. I looked over to Viola fingering Cassandra, the two women moaning and kissing and writhing up against one another, then back to Brenda.
She smiled up at me, then reached behind her back, untying her bikini top and freeing her massive tits. Her nipples looked almost as hard as my cock, and were I in any other position, I would have had my mouth on them in a heartbeat.
I took a sharp intake of breath at seeing them, making Brenda smile even more. “I’ll never get tired of that reaction.”
“I’ll never get tired of seeing you naked,” I replied quickly, my cock twitching with need.
“I know,” Brenda said, smirking as she reached down and untied the side knots of her bikini bottom, dropping it to the floor.
She now knelt naked before me, her pussy with its neatly trimmed pubic hair now visible to me. It was an amazingly lewd sight, and one that I couldn’t help but be excited by.
Moaning, she reached between her legs, fingering herself before bringing her hand up to me. Two of her fingers glistened with juice.
“I’ve been so fucking wet since I got here… so fucking horny, thinking about the others here… but I’ve been waiting for this cock. I… well, I really fucking need to suck it… you want me to suck your cock, Ryan?” Brenda asked, offering her fingers for me to suck on.
I grinned. “I think you know the answer to that.”
Without another word, I leaned in, sucking the juice from her fingers, groaning as I took in her sweet, musky taste. I’d become quite familiar with Brenda’s taste over the course of the school year, but even now, I couldn’t get enough of it. Even after I’d cleaned her fingers of any juice, I kept sucking, wanting, no, *needing* every last drop, ever hint of her taste.
I might have been overeager, but given her smile as she pulled her fingers from my lips, this pleased her to no end.
Without a word, she dropped that hand back between her legs, grabbed my cock with her free hand, then leaned in and effortlessly sucked my entire ten inches down her throat.
“Holy shit…” Cassandra groaned. I wasn’t sure if it was because of Brenda’s amazing blowjob skills, or if it was because of what Viola was doing with her pussy, but I was pretty well past caring at this point. Between watching the two MILFs fucking next to me, and the one who was giving me the blowjob of a lifetime, I was in heaven.
Brenda looked up at me, her eyes big and oh so sweet-looking for how dirty she was, bouncing up and down on my cock as she easily fucked me with her face. Between her swirling tongue and the perfect amount of pressure she could put into this blowjob, my cock felt glorious, stronger than ever and ready for another round.
I knew that Brenda liked dirty talk, so I did my best considering how distracted I was. Interlacing my fingers with her hair so I could properly fuck her face, I grunted, “That’s fucking nice… keep sucking my cock, fuck, suck my cock, slut, take it all, take fucking all of it, god, your mouth feels so good. Your lips, your tongue, fuck, everything, feels so good…”
Brenda pulled her mouth from my cock, coughing and smiling slightly as she continued stroking my cock with her free hand. “Yeah? You like that? You like fucking your hot slut of a teacher’s face? You want to cover me in cum, don’t you? Or do you want to fill my mouth?”
“Do I have to choose?” I asked, my balls swelling as she continued expertly manipulating my cock.
She smirked. “No, you don’t. All you have to do is wait for me to cum before you can fire off… you think you can do that? I’m sooooo close… sucking you off gets me so hot… please, let me cum, then you can cum…”
Without waiting for an answer, she leapt back in, sucking my cock with a desperate fervor. Brenda writhed and moaned as she energetically sucked my cock, pressing her tits against my inner thighs as she brought me to heaven. The way she was tensing, and the goosebumps that had broken out on her skin, I knew that she didn’t have very long before she would cum… but I couldn’t guarantee that I would make it very long at this point.
I looked over to Viola and Cassandra in the chair next to me. Cassandra’s moans had taken on a high, rapid tone, and soon she turned to look at me, our eyes locking as she was close to orgasm. I couldn’t say why, but as she hit that precipice, she reached out her hand to me.
I reached back, interlacing my fingers with hers. An energy, something thoroughly unexpected but powerfully hot, seemed to leap between us, driving us both to an edge we hadn’t expected.
“OH GOOOOOOOOOOOOOOOD!!!” Cassandra cried out, cumming hard under Viola’s expert fingering efforts, her body writhing and jolting as wave after wave of pleasure crashed through her.
I was close, so close at this powerfully erotic sight alone as Viola mercilessly kept fingering Cassandra, but soon I didn’t need to worry about this.
Brenda cried out against my cock, cumming hard as she continued writhing on her knees. Rather than affect her skills, she somehow only blew me harder, removing any restraint I might have been able to hold in the moment as I grunted and came hard myself. I could barely feel my legs for how amazing my body felt, but this didn’t stop Brenda as she continued to suck. She swallowed the first few shots like a pro, but as the volume soon became too much, she pulled my cock out of her mouth. Streaks of cum blasted across her face, her neck and her tits, leaving her positively covered in my cum.
When my orgasm subsided, and I fell back in my chair, Brenda laughed.
“Fucking amazing, I’m just covered!” she said, running her fingers through it.
Though she still basked in the afterglow of what she’d done to Cassandra, Viola smoothly climbed off of her and knelt next to Brenda.
“Hey, hey, save some for the rest of us!” Viola declared, leaning in and sucking some of my cum off of Brenda’s nipples.
She moaned at the taste, and Brenda moaned at getting her tits sucked by an expert like Viola.
I just looked over at Cassandra and let go of her hand, feeling a little out of my league all of a sudden. “Is it always like this?”
“Close to it,” Cassandra admitted, fanning herself off. “But we might be extra horny today because we’ve got a hung young man with us. With a new toy like that, I don’t think you can blame us for being a little crazier than usual…”
I laughed, then leaned back in my chair, looking at the sky with some amusement. Feeling triumphant, I declared, “This weekend’s gonna fucking rule!”
***
As day rolled into night, we finally got settled in. I helped carry in the bundles of firewood, the remaining groceries, and even helped the ladies with their bags. I was ogled, and did a fair bit of ogling myself, and maybe even walked in on an occasional something happening between a couple of the book club ladies. Nothing quite so steamy as what happened by the pool, but still pretty fun to accidentally walk in on. I knew we were all just recharging, waiting for the right moment for things to escalate.
That moment came a little while after dinner, with the sun a distant memory. Once our stomachs had settled, the six of us changed into swimsuits and retired to the hot tub. I gotta say… sitting in a hot tub surrounded by five gorgeous MILFs in their skimpiest bikinis, it was something I could definitely get used to.
“Please, Viola, tell me this place has a stripper pole!” Lauren laughed, a glass of wine in her hand as she looked across the tub to Viola.
“Did you expect anything less of me?” Viola laughed, reaching across the hot tub and clinking her own glass against Lauren’s. “Of course this place has a stripper pole. I know how to plan ahead, and I promise you won’t be disappointed.”
“We’d better not be. You have seen Viola strip, haven’t you, Ryan?” Lauren asked.
Sandwiched between Viola and Valerie, I might have felt on the spot here, but I wanted to show these women that I could keep up with them.
“Oh, yes, I have seen her put on a show. She really knows how to work the pole,” I said, smirking.
This got some laughs from the collected book club. Things had gotten a little rowdier since the alcohol started flowing, and I got the impression the night was only going to get wilder from here.
“Ryan, I’ve been meaning to ask… how are you doing with your post-senior year plans?” Cassandra asked.
Her tone was perfectly pleasant and curious, the kind of tone that a friend of the family would make under more normal circumstances. Nevertheless, I gulped, because this was a bit of an undecided subject, but one I could reasonably deal with.
“I was thinking about heading to the community college first, something that’d hopefully help me figure out what I want to do with my life without spending too much money. Dad’s got some saved up for me already for that purpose, so, I think all I really have to do is just pick up an application and hope for the best,” I said.
“Smart fucking move,” Valerie replied, nodding. “Get those general eds out of the way first and cheap. I’ve got friends who will be paying off grad school student loans by the time they’re great-grandparents… avoid those if you can.”
Brenda and Lauren added their own affirmative responses to that sentiment, which made me feel a little better.
“Are you sure you don’t want to aim higher than that?” Cassandra asked, still curious. “You seem quite bright, I’m sure your grades are good enough to get you some attention.”
“My grades are alright,” I said.
Valerie laughed. “Alright? Ryan, you’re better than alright, stop selling yourself short! The world’s gonna underestimate you enough, it’s better if you’re not making it any easier for them.”
The way she said that made me feel warmer inside, but maybe that was just the tub. Or the way her massive breasts looked in her black, barely-there bikini.
Seeing where my attention had wandered, Valerie smiled and teased, “I mean, you haven’t even fucked me yet, and you’re still earning A’s in my class.”
“Hey!” Brenda shot back, playfully. “He was earning A’s in my class too before we started having sex. And the grades he’s earned since are still legitimate, thankyouverymuch. The sex is just a very nice bonus for both of us.”
“Exactly,” I replied, nodding at Brenda. “And, thank you, incidentally.”
“Oh, no problem!” Brenda exclaimed, licking her lips.
“See, this is what I mean! You’re getting great grades; you could try for so much more!” Cassandra said, sympathetic yet only slightly pushy.
“Cassandra, remember, we’re here to relax and have fun…” Lauren said. Sitting next to Cassandra, Lauren took this opportunity to playfully poke her in the side.
Cassandra yelped. “I’m just trying to help out! I mean, Lauren, after his mom passed, we both practically raised him, I thought you’d be on my side in encouraging-”
“Lauren?” Viola interrupted, her voice playful yet firm.
“Yeah?” Lauren replied, clearly happy for the interruption.
“I think Cassandra could use a distraction,” Viola suggested, firmly.
“So do I,” Lauren said, setting her drink down on the edge of the hot tub, then reaching over her head to pull off her bikini top. Her massive tits now freed, Lauren grabbed Cassandra by the back of her head, and pulled her into her exposed breasts.
“See?” Lauren joked, moaning softly as Cassandra instinctively sucked on her tits. “Isn’t this much more fun than giving Ryan a hard time about college?”
Cassandra pushed herself away, looking both angry, but amused. “What the fuck was that?”
“A distraction,” Lauren said proudly.
“A pretty hot one, too,” Brenda agreed, pulling off her own top and tossing it outside of the hot tub.
Crossing her arms over her chest, Cassandra huffed, “If you think the two of you showing off your amazing tits is going to shut me up… well, you’re probably right. I think I forgot where I was for a moment.”
“Then the distraction was a success!” Lauren declared, pulling Cassandra’s face into her tits briefly, before letting her go again.
“You’re gonna pay for that, Red,” Cassandra warned playfully, before turning her attention back to me. “Sorry about that, Ryan. I’ll stop trying to be a mom and just be the hottest bitch here instead.”
For emphasis, Cassandra pulled off her own top. Staring at the buffet of beautiful breasts, I responded, “Oh, don’t worry about it, Cassandra… I’ll be fine. It seems like we’re all going to be fine pretty soon.”
“You’re damn right about that,” Lauren replied, pulling Cassandra into her lap.
The two women soon had their arms wrapped around one another, kissing each other deeply as they groped each other. With hands soon disappearing beneath the water, I was also willing to put money on there being a fair bit of fingering occurring.
“You know, Brenda, I’m suddenly feeling pretty fucking left out,” Viola said, pulling her own top off and freeing her beautiful, bare B-cups, then reaching beneath the water to free her bikini bottom before tossing both pieces out of the hot tub.
Looking at her hungrily, Brenda reached down and pulled off her own bottom before replying, “Well, we wouldn’t want that… not after you took the time to set up this slutty little club…”
Brenda hardly objected as Viola climbed over her and straddled her hips, leaning in to passionately kiss her. The two women intertwined like this worked matched the other couple well, all four of them writhing and touching one another and looking hot as fuck. My cock was as hard as it had ever been in my life, and I found myself suddenly wanting to do absolutely everything and everyone all at once.
I looked to my right, at Valerie as she sat watching the others in some awe.
“This is so fucking hot, isn’t it?” she asked, reaching down between her legs with both hands. The way she was moving and softly moaning, I knew she was touching herself, which might have made me even harder in this overcharged moment.
“Seriously,” I replied, licking my lips as I eyed her. “Though it really feels like we’re now the ones being left out here, doesn’t it?”
“A little,” Valerie agreed, before looking at me and grinning. “You know we don’t have to be left out, though, right?”
“I guess we don’t,” I said, sliding closer to her and wrapping an arm around her shoulders.
Her 5’2″ frame felt positively tiny next to me, but the way she looked up at me so expectantly, with a big goofy grin and some of the sultriest eyes I’d ever seen, I knew there wouldn’t be any problems between us. Her skin felt so soft against my arm, her body pressing into mine feeling so perfect…
Without breaking eye contact, Valerie reached behind her back and undid her top, dropping it outside of the hot tub. I was given another magnificent view of her amazing D-cups, her dark, firm nipples standing out enticingly. Then, reaching beneath the water, she wiggled in her seat, and soon pulled off her bottom and dropped it with the top.
“Your turn,” she said, looking down at me expectantly.
“You’re not going to get the greatest view,” I said, arching my back so I could pull off my shorts and then drop them on top of her swimsuit. “But, at least we’re on even terms.”
“Yay,” Valerie purred, climbing up and straddling my hips.
My cock was sandwiched between us, but I could distinctly feel her hot, moist pussy against me, even underwater.
Pressing her tits against my chest, Valerie leaned in and looked up at me with the dreamiest eyes.
“You know, I’ve wanted to do this for a very long time,” she explained, lowering her voice in the best attempt to get us some privacy. “I’ve been hearing stories about you for so long, and I knew that I had to get some time with you for myself. And it’s not just because of your cock, or your tongue… but they all tell me that you’re so nice, and you listen, and I could just use that in my life sometimes, you know? But something never lined up for us, and even with the book club I’ve just been getting hornier and hornier… With how often my husband’s away for work, and probably fucking around… the urge for cock’s been really strong, but finding the right opportunity, that’s always been the challenge.”
I leaned in and kissed her deeply. Valerie was an enthusiastic kisser, throwing her arms around my neck and pulling in close, her tongue darting into my mouth as we explored one another. It felt… well, it felt fucking amazing kissing her.
With the greatest effort, I broke the kiss and asked, “So… how’s this for the right opportunity?”
“It felt good so far, but it seems likely we’re going to have to repeat the experiment to be certain,” she giggled, leaning in and kissing me again.
I ran my hands down her back before finding her full ass, squeezing her as she ground against me. She had a truly glorious ass, simultaneously firm and soft, and my squeezes seemed to only excite her further.
Rocking her hips to rub her pussy against the base of my cock harder, Valerie leaned her head against my chest and said, “Fuck… I love getting my ass played with… I never get that at home… and these ladies can scratch that itch, but sometimes you need a man’s strong hands groping your ass, you know?”
“Oh, I have absolutely no problems with ass,” I said, smiling at her. “I’m kind of an ass connoisseur, you might say.”
“I might hold you to that,” she grunted, shifting positions and sliding her pussy further up my cock. “You like that?”
“Uh huh…” I moaned, looking forward to feeling her tightness wrap around me.
She didn’t do that, not here, and instead slid back down, pulling me in close so she could whisper in my ear. “I’m not gonna fuck around Ryan. I want you. I want you bad, but for our first time, I want you to myself, and somewhere far more comfortable than a hot tub. You cool with that?”
“Cool. I’m very cool with that,” I answered, quickly.
“Good,” Valerie replied, taking my hand and climbing out of the hot tub.
Dutifully, I followed after her. I couldn’t take my eyes off of her body, glistening in the low lights of the pool area as she dripped with water. Her face looked so lively and energetic, much like the enthusiastic science teacher I knew from school, but somehow seemingly, well, even more *herself*. It was a good look for her, and one that I couldn’t wait to see more of.
Grinning widely, Valerie looked over her shoulder and called after the others, “We’ll be right back! Or maybe not, I don’t know; Ryan and I are gonna fuck!”
“Enjoy!” Viola called out over the chorus of moans coming from the hot tub.
With Valerie leading the way and her grip tightening on my hand, I knew that we would soon do more than enjoy ourselves.
***
While it might not be the steamiest of transitions, after getting out of the hot tub and making our way over to her room, Valerie talked me into taking a quick shower and cleaning up a little before we made our way toward her bed. She was committed to wanting to make this comfortable too, not allowing me to get too far in the shower no matter how much I groped and teased, but she knew what she wanted and made that fairly clear, so I backed off and followed her direction.
As I lay down on the sheets after the shower, cleaned and dry, my cock standing tall and proud as it had ever since we were in the hot tub, I briefly looked at the large mirror beside the bed before turning my attention to watching her dry her hair with a towel. I looked between her legs, seeing her shaved pussy with its very prominent lips, clearly moist and not just because she was drying herself off.
She looked tasty. I licked my lips.
“Don’t get me wrong, I think the hot tub’s as sexy a place as anyone,” Valerie explained, looking positively luscious as she ran the towel vigorously through her hair. “But mostly just on paper. Between the chlorine and the risk of pushing water in places you don’t want it pushed, and all of us in there at once, it can be something like a petri dish that I’d rather not think about too hard. Don’t let it stop you, and I won’t let it stop me, I’ve had plenty of fun in hot tubs before, and I don’t think anyone in that tub’s in that kind of danger because this isn’t that kind of story, but, when you’ve got the option for a shower and a bed, I think I’m gonna take it. Wouldn’t you?”