Book Club Memories Ch. 03

"But I like orgies..." I pouted.

"So do I, so do I, but you can't be fucking all the time. You need to recharge too if you're going to stay good for the rest of the orgy," she explained, squeezing me with the arm she had wrapped around me playfully.

I sighed, still pouting a little. "I know..."

Cassandra smiled. "Come on, things are going to look a lot better once I get you to my room, trust me."

"Okay..." I said, happy to have her steadying my balance, and even more for the closeness. I'd had a lot of love for Cassandra Pruitt over the years, standing in for my own mom after she passed away far too soon... and a lot of the familiar feelings surged through me here as we walked, her taking care of me as she always had. Admittedly, some things had also changed, like the fact that I was going to spend some of the rest of the day having sex with her, but all in all, there was a familiar, nice warmth between us that I needed right now.

There was little of that warmth, however, in the laughs I heard up ahead. Not evil, to be sure, but definitely the telltale sounds of a couple of MILFs a few glasses of wine in and having a good time cutting loose.

The first MILF I saw rounding the corner in front of us was one I was intimately familiar with. Lauren McNeil may have dressed back in her bright green bikini, but that didn't stop the 5'11", utterly stacked redhead from looking equal parts intimidating and gorgeous. The top was stretched to the max around her DDD-cup tits, and her long legs looked a little wobbly (though whether that was from a morning of sex with me, or the wine glass in her hand, I couldn't say), but she was a sight to behold, an Amazonian goddess that I had had the pleasure of taking to bed on multiple occasions.

However, the newest arrival who walked in behind her could have put Lauren's "Amazonian goddess" title to the test.

This woman was 6'0" of toned muscle, not too bulky but definitely noticeable, especially given how she was only wearing a tight white tank top (cut to show plenty of midriff) and cut-off jeans. Her soft, brown skin and dark, curly black hair that she'd tied back in a thick ponytail reflected her Latina heritage well, complimenting her utterly epic ass and thoroughly enormous EE-cup tits. While her face had a certain harshness to it most of the time, now her full lips were curved into a broad, toothy smile as she joked with Lauren, and her cold brown eyes sparkled with warmth and good cheer.

The new arrival was stunning by any objective standard, and yet I couldn't help but feel an instinctive fear upon seeing her in my current, vulnerable state.

After all, most every student at Regan Hills High School knew to fear school security officer Brandy Rivera. While I hadn't gotten on her bad side yet, I'd had a few close calls over the year, and I wasn't looking forward to any this weekend.

"Officer Brandy..." I gulped as Cassandra guided me toward Lauren and Brandy.

"She's harmless here," Cassandra said, before amusement took her voice. "Well, as harmless as you want her to be, anyway..."

Even in my tired state, my cock twitched a bit at that thought, but before I could let it become anything concrete, Lauren and Brandy noticed us.

"Ryan!" Lauren exclaimed, looking me up and down. "You look exhausted! Did I really take that much out of you?"

"Partly, though Wanda had a hand in that as well..." I muttered, smiling.

"She'll do that. Oh, you poor dear," she replied, hugging me close and kissing me sweetly.

"I'm taking him to get cleaned up and grab a nap, don't you worry, I'll have him back and in working order... eventually," Cassandra said, keeping her tone mischievous.

"Greedy whore," Lauren chuckled, letting me go and giving a quick kiss to Cassandra.

Cassandra shrugged. "If the shoe fits... fuck, you're looking really hot right now, Lauren..."

And with that, Cassandra kissed Lauren in a decidedly less quick fashion, the two of them soon passionately locking lips and pressing into each other while I still stood, now having to lean against the wall for balance.

As they made out, I became thoroughly aware that I was still naked, and that Brandy was looking at me while Cassandra and Lauren made out. Her eyes were thoroughly appreciative as she looked me over, especially as her eyes landed on my cock.

"Hey," I said, stepping away from Cassandra on my own slightly unsteady legs as she and Lauren took the moment to make out.

"Hey," Brandy said, her eyes still on my cock. "So, you're the infamous Ryan Collins."

"I'm not *that* famous, Officer Brandy," I joked.

She rolled her eyes. "That's not-"

"I know what infamous means, and that it's different from *in*-famous and... okay, I'm tired and getting stuck on old movie references... yeah, I'm Ryan Collins, that's me..." I murmured.

Brandy smirked. "I've never seen you in trouble, though the way I hear you sling that dick around school, that's kind of impressive."

"Thanks?" I said. "You almost caught me once, in the back of a van... but that's not important now."

"No, it really isn't. This is my fucking vacation, and I'm just here to hang out with friends, not worry about the husband and kids back home, and get *fucking* laid," Brandy replied.

The way she looked right now, I doubted getting laid would be a problem for her.

"I'd say you came to the right place," I said, smiling weakly.

"I'd say so..." she said, finally looking back up to my face. "Though if you want some of this, I'm gonna need you to rest the fuck up first, you know that, right?"

"Well, I owe Cassandra some private time..." I said, watching as Cassandra and Lauren continued to make out (and looked about three steps away from fucking in the hallway), "...but let's see where I am tomorrow."

"I'll fucking hold you to that; when they told me there'd be some huge fucking cock here, I got so damn excited 'cause I ain't had that in so fucking long, so you better be able to deliver, or I might have to punish the fuck out of you," Brandy said, smirking again.

Something told me she might enjoy punishing me no matter what, and looking at her, I doubted that I'd mind whatever kind of punishment she'd have to offer.

"I'll have to be good, then," I said.

"Not too good..." Brandy said, reaching out and running a finger along the underside of my now very hard cock. "So, if Cassandra's not gonna drag you off this second, can I suck your cock until she gets her shit sorted out? I haven't sucked a cock that fucking huge in, like, forever, and I need that down my throat so fucking bad. You can cum if you want, or not if you're saving it for her, which is also cool. You can see my tits too if you want."

Well, she was rather to the point, wasn't she? And she was looking so good, her tits nearly bursting out of her top, those wide hips and nice, thick, Latina ass just perfect for what I could unleash... I wasn't at my best right now, and couldn't do a whole lot, but seeing her moisten those full lips with her tongue, I had to say that she made a good case for her proposal.

Seeing as how Lauren and Cassandra looked like they'd be a moment, and since I was starting to feel a little stronger, I said, "Yeah, for a little while? And definitely more tomorrow?"

Smiling, Brandy dropped to her knees in front of me. "Awww, now that's the kind of fucking date I haven't gotten in, like, forever... thanks, Ryan, I'm lookin' forward to it already and I still got this python in front of me! Man, this weekend's off to a good start..."

I didn't want to boast about how great a weekend I'd already been having, so instead I just looked down at her, watching with some anticipation as she moistened her lips again, parting them slightly as she leaned forward to suck my cock.

This no doubt would have felt great, but it was something I would have to discover later (and, spoiler alert, I definitely did), as Cassandra's hand on my shoulder pulled me back a couple steps before Brandy could take me in her mouth.

"Oh, come on, Cassandra! That's fucked up!" Brandy protested. "I was just gonna suck his cock! And look at him! That cock needs suckin'!"

"Sorry, Brandy, you know I love ya, but Ryan here's exhausted and needs his rest, and I've been wanting him to myself since yesterday!" Cassandra said, lacing my fingers in hers as she started leading me back down the hallway.

Still kneeling on the floor, Brandy looked at us agog, then back to Lauren. "You believe this shit?"

Lauren laughed. "Of course, I do. You'll get your chance... how 'bout I vibe you 'til you forget all about it?"

"I ain't forgetting that anytime soon," Brandy said.

"What if I use a *really* strong vibe?" Lauren proposed.

I didn't get to hear what Brandy thought of this, but I did see her eyes staring holes in Cassandra and me as we walked away.

"Officer Brandy looks pretty pissed," I said.

"She runs kinda hot, but she's harmless," Cassandra admitted, going back to wrapping my arm over her shoulders to better support me. "If anyone's gonna be on the receiving end of that anger tomorrow, it's gonna be me, and I can take it."

She sighed, pleasantly. "Oh, can I take it..."

I thought about probing her more on her history with my school's security officer, but by this point, I had to admit that Cassandra was right. I was pretty well exhausted, and my mind was starting to wander. As hot as it was seeing Brandy drop to the floor so eagerly, I was finding myself welcoming a moment to cool off and recharge.

Cassandra clearly sensed this. "Let's get you to my room... get you that nice hot shower, and then a nap before we have any fun... how's that sound, Ryan?"

Teasingly, I rolled my eyes and said, "Okay, *Mom*."

A strange look crossed Cassandra's face, but rather than linger on it, she shook her head and laughed.

***

Alright, so I gave her a hard time over what she thought was right for me, but at the end of the day, she *was* right. A hot shower cleaned me of a day's worth of sweat and exertion, and by the time I'd buried myself in her bed, I was pretty fast asleep. It was one of those naps where the moment my head hit the pillow and I closed my eyes, I suddenly was opening them up again, only it was much, much later.

Groggily, as I woke up, I reached for my glasses on the bedside table, putting them on and checking the clock... fuck, had I really been out for four hours? I needed that, I guess, but, wow, I was really out, wasn't I?

"Ah, welcome back to the land of the living!"

I turned my head to the other side of the bed and saw a Cassandra Pruitt I was much more accustomed to seeing. Gone were her stylish sunglasses, replaced with her customary everyday glasses that wouldn't win style points anytime soon (but always made her look cute as hell). Her long, silky black hair was up in a casual bun, and rather than sexy lingerie, she wore a pair of pale pink pajama pants and a baggy, Cal State Los Angeles hoodie.

Overall, she looked more her casual, "cool mom" self I'd always known her as, rather than the seductress she'd seemed this weekend.

She'd clearly been watching something on her laptop when I woke up, and pulled out her earbuds, setting it aside.

"Whatcha watching?" I asked, probably sounding a lot groggier than I meant to.

"There's Something About Mary," she said, sounding only slightly embarrassed. "It dates me as a child of the 90s, but what can I say? It's still one of the better rom coms out there."

Racking my brain for the reference, I asked, "Isn't that the one about stalking?"

"Yeah. Rom coms have a really low bar to clear to be decent," Cassandra said, shrugging. "At least porn tends to have a certain kind of honesty to it."

"Sometimes," I agreed, yawning and stretching, sitting up in bed next to her. "I was never really one to watch it for the plot."

She rolled her eyes at me. "Why doesn't this surprise me? Teenaged boys..."

I don't know why this moment, of all moments, made me aware that I was still naked, and almost want to cover myself up as if she hadn't seen me naked a bunch this weekend, but there you have it. I was happy for the blanket still covering my lap as I got my bearings, though it did little to hide my obvious erection.

Cassandra was nice enough not to make mention of my discomfort.

"I'd have thought that you'd be out with the others... the party already dying down?" I asked.

"Hardly," she answered. "You missed a pretty round of screaming earlier... Valerie, probably. She was talking about how she could take pretty much anything up her ass, so Lauren challenged her with one of Viola's bigger strap-ons and... well, you get the idea."

"Screaming," I said, nodding.

"Screaming," Cassandra replied. "And while I like a lot of screaming and constant pleasure, sometimes you just want to be normal and relax for a few minutes too, get some private time, watch a rom com while one of your daughter's best friends sleeps naked next to you? Alright, that last part probably isn't all that normal."

"Probably more normal than you'd think in Regan Hills," I laughed.

She joined me, chuckling softly. "Yeah, the way things go around there... wouldn't surprise me for a second."

The way she laughed, it was familiar to me, and not just because I'd known her most of my life... no, the way she laughed was almost identical to the way Kaitlyn laughed. Maybe lacking the edge of Kaitlyn's laugh, but still, it was nearly perfect and a little unsettling, honestly. There was so much about these two women that was alike, with nearly identical bodies (though Cassandra had wider hips), and their faces were different from each other, even though they were both beautiful. I'd had sex with friends' moms before, but the tension between us, and everything that had already happened this weekend, made this a particularly charged moment.

"So..." Cassandra said.

"So..." I replied, a little nervous.

She shook a thought away, her smile nearly as nervous as I felt. "So, this is still weird, right?"

"A little, yeah," I admitted.

"Still good weird?" Cassandra asked.

Looking at her as she pulled her knees to her chest, still smiling at me hopefully, I answered, "Yeah. Still a good kind of weird."

"Oh, cool... that's awesome," she said, breathing a sigh of relief. "Because I know how horny comes and goes, and that the other ladies have been doing their best to drain you today, and when guys are drained, reality seems to hit them a lot harder... I was figuring that you might have been less interested in... this. Us."

I slid a little closer to her under the covers. "I don't think there's a way any guy could be less interested in you..."

Cassandra rolled her eyes. "Tell that to the guy on Kaitlyn's birth certificate. Gets me pregnant at eighteen and runs like hell, leaves everything to me... and my husband is a good man, and an amazing stepfather to Kaitlyn, but he's always been more focused on work than play, if you get my drift."

I quickly looked to apologize. "I'm sor-"

"Don't be sorry," she interjected. "You only meant to compliment, and you paid it as such. It's just that, well, we don't have the best luck in our family when it comes to men. Mom got pregnant with me when she was eighteen too (lucky she's not here, that woman's a cougar and she'd be all over you) and Dad ran off not long after, you already know my sad story, and Kaitlyn... well, the way she's going, she's probably going to keep the family tradition alive. At least I know that you won't run out on her when you get her pregnant."

"If," I corrected, without mentioning that Kaitlyn and I hardly practiced what you'd call safe sex.

"Sure," Cassandra said, smirking. "I've heard how you two go at it, so let's just say I know what the odds are... but that's not what matters now. What matters is... I know that this isn't exactly normal, what's going on between us, but I like it. You've always been good, to Kaitlyn, to me, and after how you've treated all of my friends, and knowing what you're packing... I want you, Ryan. And you still want me?"

"Is that really a question?" I asked without hesitation.

"After your little 'mom' joke earlier, I thought it might be," she said, still confident, if more than a little curious.

Ah, right, I had said that, hadn't I?

I tried my best to do damage control. "Can I blame it on being tired? Because I was really tired there... I'm not anymore, but... okay, being tired's not going to be sufficient, is it? Because I really, really do want to do all sorts of things with you, and-"

Cassandra laughed, lightly. "It's fine, Ryan."

"You sure?" I asked.

"Very sure," she said, putting a hand on my thigh and squeezing. "I know that there's some maternal feelings between you and Brenda and Lauren too, and lord knows that hasn't stopped you from fucking either of them... and Lauren's daughters for that matter, it's just as far as I know, you haven't really called either of them 'mom' before, even joking. I just wanted to make sure that everything was still cool between us."

This was getting a whole lot more Freudian than I was expecting (not that I was going to complain), and I was hoping to switch that around in a much more constructive manner.

"Everything is cool..." I said, confidently as I pulled the blanket down to expose my erection to her. "...everything is very, *very* cool."

Her eyes widened enthusiastically at the sight. Cassandra licked her lips.

"Well... it's good that we're on the same page about that, then..." she replied, smiling at me, then biting her lip.

I'd seen some "come fuck me" looks in the past that utterly destroyed me, but this was easily one of the best that I could remember. I kept expecting her to make a move, like so many of the other ladies of the book club, I expected her to be the aggressor... but she wasn't. Cassandra simply sat there, looking casually luscious, eying me and breathing heavily, her lips parted tantalizingly as her full bust rose and fell behind her sweatshirt.

Fuck, she was hot... and if she wasn't going to make the first move, well...

Alright, it might have been the last two days of being teased by Cassandra's body, so I might have kind of tackled her, throwing her onto her back on the bed while I climbed on top of her. She let out a sound of soft surprise, but then smiled up at me broadly as she looked at me on top of her, naked.

"I know that this is a little weird, but after this year, I've come to really enjoy weird... and what was it that you asked me yesterday?" I said, rubbing my cock against her clothed body as I smiled down at her. "You want things to get any weirder?"

Unhesitatingly, Cassandra replied, "God, yes."

"Good," I replied, leaning down to kiss her passionately.

Her lips felt good... god did they feel good. I shouldn't have been comparing her to Kaitlyn right now, but there was something familiar to this kiss... but something even naughtier, more exciting. I had seen so much from Cassandra these last couple days, and with her as one of my longest-standing crushes, everything felt like the culmination of one of my greatest fantasies. Pressing my body to hers, finally feeling those luscious curves against mine, her lips eagerly exploring her mouth, her tongue tentatively brushing against mine before getting much, much bolder... god, did it all feel right.

"Mmm, god yes..." Cassandra moaned as we made out, wrapping her arms around me and running them down my back. "God, this is so overdue... fuck, we should've done this ages ago..."

"We should've..." I agreed, kissing her.

"Yeah... if I'd known what you were packing, I'd have called you over for tutoring myself..." she giggled. "We could've been doing this all year."

"Well, we've got plenty of time to make up for," I said.

I leaned up just enough to reach down and grab the hem of her sweatshirt, and forcefully pulled it up over her breasts. Seeing her DD's exposed and bare, her nipples firm and begging to be sucked... well, I did what any sane person would do.