Book Club Memories Ch. 03

I laughed, then reached over to comfortingly squeeze one of her tits. "It's all good, really... I've seen and done a lot of weird stuff this year... that may have been up there, but it wasn't enough to scare me off."

"Clearly," she said, opening her eyes and looking down at my half-hard cock.

"Clearly," I replied. "And it's not like you're the only one; I think Brenda's got a thing for that too, if what we were talking about earlier's any indication. She said some of the rest of the club's kind of got a thing for it too."

"Oh, yeah, definitely... I know that's one of those fantasies that drives a lot of the other girls wild, and, I mean, let's just say that in a pornier world, in a year's time you'd probably see most of us here with new bundles of joy who look an awful lot like you," Cassandra replied.

I thought I already lived in a world that was about as porny as it gets, but, hey, to each their own.

"Yeah, I imagine..." I said, trailing off as I looked up and down her well-fucked body.

She scrunched up her eyes again as if approaching something she didn't want to approach. "It wasn't too weird for you, was it? Because I was just kind of riding a vibe there, figuring you'd be as nasty as the voice in the back of my mind often is, and I just kind of rolled with it and now I'm feeling incredibly self-conscious because-"

I interrupted her with a kiss, quick and to the point. "I'm fine. Really. I kinda liked it, honestly."

"Yeah? You did, really? You're not just saying that?" Cassandra asked.

"Not just saying it, and, yeah, it got me pretty hot... I mean, it's always nice to know you drive someone that wild, isn't it?" I suggested.

She laughed, a single, quick bark, but it looked like she'd calmed down some. "Yeah... yeah, it is... I knew I could get you going pretty decently there, but when you were on top of me... holy fuck, that was hot. I don't think a guy had ever fucked me that hard before. I'm gonna be walking weird for a while after this... but fuck, is it totally worth it."

"That was pretty hard," I admitted. I let the words hang that way, seeing how she'd pick them apart.

"'Pretty' hard?" Cassandra said. "You can go harder than that?"

Yeah, she got what I wanted her to get.

I nodded, then decided to see where I could lead this. "I mean, I wasn't holding back, and it all depends on position and how excited I get... like, if I were fucking your ass, I'd probably go at it harder than I did there."

Cassandra raised an eyebrow. "You know, that was actually a pretty decent segue into trying to fuck my ass."

Without pausing, I asked, "Did it work?"

She thought about this for a couple seconds. "No..."

I shrugged, then squeezed her tit again in commiseration. "Well, can't blame me for trying..."

Cassandra reached down, gently squeezing my cock. "You didn't let me finish, Ryan... I was saying that it didn't work, because I was already down for letting you slide your cock up my tight, perfect ass the first time I saw it. I was just hoping you'd still have the energy for it, because I know we've been working you sooooooo hard today."

I was having a hard time figuring out who was leading who at this point, so I just rolled with it. "I can be ready again soon."

"I'll help!" she chimed in, before crawling on top of me again.

Rather than try to force my cock into her pussy again, Cassandra worked her way down my body, kissing and licking me. She took distinct pleasure sucking on my nipples as she got to them, even nibbling slightly in a way that made me hiss and twitch from pleasure and pain. This only spurred on the fire in her eyes as she worked her way down, kissing her way toward my cock. She licked and sucked at it a little, feeling fucking amazing while she never once broke eye contact with me, but she was hardly finished there... fuck, no, she wasn't finished.

Running her tongue down the bottom of my shaft, she soon began to suck on my balls, tickling them and teasing them with her lips and tongue while slowly stroking my cock with one hand. It was about this time when I wondered why she was only jacking me one-handed, when I felt her other hand sneak along my ass. Without breaking eye contact, or her suction on my balls, Cassandra pressed a finger between my ass cheeks and...

"Fuck..." I hissed, groaning deeply as she pushed her finger into my ass.

Cassandra let my balls go free, grinning up at me naughtily as she continued stroking and fingering me. "Lauren told me you enjoyed that."

"She's not wrong," I whimpered. The pleasure was beginning to overwhelm me, and the moment she had penetrated my ass, I was suddenly hard as iron again.

"And it did seem to have the intended effect," Cassandra mused. "So... I could do this for a while, and it looks like you could take it for a while, but I need my ass filled and I need it filled soon. You ready for that?"

I thought on this for a second before I asked, "You got more of that oil?"

Cassandra grinned. "Of course!"

Now, there are a lot of ways that she could have lubed up my cock, but I really appreciated how she chose to first apply another coat to her tits, then decided to apply it to me with another quick, vigorous tittyfuck. She seemed pretty satisfied with this as well, moaning in time with my grunts as she pleasured me... goddamn was she a sight to behold. Cassandra Pruitt had always been the "cool mom" to me, but a mom all the same, someone to look up to and respect and admire, not... well, the vixen who was tittyfucking me before I railed her ass.

And yet, here we were.

Content that she had me lubed, she then got onto her hands and knees next to me. "Well? What are you waiting for?"

This was a very good question.

I got up on my knees behind her, and took a moment to admire her full, firm, and thoroughly round ass. The cheeks were remarkable, begging to be squeezed and spanked, the valley between hiding an asshole I'd buried my tongue in not so long ago... fuck, it took a lot not to dive back in and take another taste of her delicious asshole.

I slid my lubed-up cock between her ass cheeks, spreading the oil around and teasing her hole with the head.

Cassandra tossed her hair over her shoulder, looking back at me as she leaned back against my cock. "Come on, Ryan... I haven't had a guy fuck my ass in so long, and you said you could fuck me even harder..."

She squeezed her ass cheeks around my cock, twerking lightly against it as she massaged my shaft.

Biting her lip seductively, she continued, "Come on, Ryan... fuck me... fuck my slutty ass, please?"

I grabbed hold of my cock and lined it up with her tight hole. "Anything you say... Mrs. Pruitt..."

She shivered, grinning gleefully as she reached between her legs with one hand and began fingering her clit.

I pushed forward, roughly and with very little mercy. With this much oil, and her eagerness, there wasn't as much of a fight as I was expecting. There was resistance, to be sure, a pleasurable friction that had her grunting and pressing back against me as my titanic cock pushed into her seemingly miniscule asshole, but the moment I really started to press, I felt her opening up to me.

"Goddamn... goddamn it, fuck, fuck, fuck," Cassandra grunted, pushing back against me, her voice growly and bestial as she willed herself to take my cock. "I want it... I want it, I want it, I want it... I WANT IT!!!"

With this declaration, she pressed back against me, and I thrust forward, burying my cockhead and nearly half of my cock inside of her.

"Oh... oh god, FUCK! FUCK YEAH!" she squealed, fingering herself vigorously as she pushed back against me. "Oh, fuck, I was scared there for a second, but this... this is amazing, this is... fuck!"

"Wait'll you feel the rest of it," I said proudly. I pushed forward, burying a few more inches into her tight, hot hole, and then the last couple. Cassandra groaned and squealed as I violated her forbidden hole, her breathing ragged and her words now formless grunts as she dropped her head down and I bottomed out in her.

I held here, squeezing her ass and taking in the awesome feeling of being buried deep inside of her tightest hole.

As ever, when the impossible in my life had become suddenly and tantalizingly possible, I just had to take a second to soak everything in. Not that I'd take much more than a second, however... not when she'd gotten me this horny.

Whimpering, Cassandra turned back to look at me again. "W...w...wow... okay... okay, I can see why my friends love having you up their ass... it's... it's pretty fucking great..."

Smirking, I pulled back, then thrust back inside of her. "Kaitlyn fucking loves it too."

She moaned as I thrust in and out of her again. "That... that a fact?"

"Uh huh..." I grunted, grabbing hold of her hips as I began to fuck her proper. "She fucking loves taking my cock up the ass..."

Cassandra groaned loudly, quickening her pace as she fingered herself. "I knew I raised her to have quality tastes..."

Thrusting in and out of her rapidly now, I could only agree. "That you have, Mrs. Pruitt... that you have..."

Her eyes blazing, she stared back at me. "Now shut up and use me like a cheap whore..."

I couldn't deny her that, could I?

I'd like to say that the next minutes contained more of this witty banter, but I'd be lying if I did. Once you get in an ass as exquisite as Cassandra's and you really get going, there's really no turning back. With my hands on her hips and my cock driving in and out of her ass, I was a fucking machine consumed by our mutual pleasure. Her groans and squeals kept me going, the feel of her tight asshole squeezing my cock impressively pushing me to go after her harder and harder.

When my slightly lubed hands began to slip on her hips, I had to improvise some new uses for them. Wrapping her long hair around my hand and pulling back seemed to get her going pretty well, arching her neck and back so I could get a decent look at her wildly bouncing tits from this angle. With that look of pleasure in the pain in her eyes, I couldn't help but spank her.

SMACK!

SMACK!

SMACK!

Every impact made her sharply cry out, then push back against me harder. I pumped in and out of her with a fury that could barely be controlled. Rational thought had left us both as our passions took over, our only motivation now a seeming need for release.

Cassandra broke first, her asshole tightening intensely as she came loudly and wetly. I let her hair loose, letting her collapse to the bed while I shifted my hands to try to take hold of her hips again. Not far behind her, I soon pulled out of Cassandra, rapidly jacking my cock until I came across her ass and lower back. I was impressed by how much cum I still had in the tank, but it was enough to paint her pretty decently.

Unable to hold herself up anymore, Cassandra fell onto the bed, then rolled messily onto her back. I crawled up her body, my cock still spasming slightly as light spatters of cum fell onto her left tit, before I brought my cock to her face. Unhesitatingly, she sucked the last few drops out, then seemed to fall into a pleasant daze as she closed her eyes, humming softly as she continued to suckle on my cock.

With pleasure overwhelming my body, I had to pull away on my own, collapsing next to her on the bed as we both caught our breaths and quivered.

"So..." I said.

"Yeah..." Cassandra confirmed, grinning and looking positively radiant. "...I know you've been up to a lot this year, but I just gotta say, that's the best sex I've ever had with a man, hands down... fuck, Ryan, you are fantastic..."

"I'm not the only one," I said, looking up and down her well-fucked body with awe.

"Thank you..." she purred, snuggling up next to me messily. "So, after this, wanna clean up again, grab some food, and spend the night here? I know Lauren and Brenda had you last night, and if you want to go back to them, I totally get it (because... I mean, look at them), but-"

Kissing her, I said, "I'd love to."

"Cool," Cassandra said, draping an arm across my chest and sighing pleasantly.

"Cool," I agreed.

I looked up at the ceiling thoughtfully, realizing that while my life might be crazy more often than not these days, it was pretty fucking amazing too, and that while I didn't know what the next day would hold at this book club getaway, I didn't think it would lack for any more crazy or amazing.

For now, though, it felt pretty fucking good to lay here curled up next to Cassandra.

***

(Author's Note 2: Writing this story is something I do in my spare time for fun, so if you're enjoying this, please, please, please drop some stars, reviews, or shoot me some feedback, as these really keep me going (and please vote on any earlier chapters you enjoyed if you haven't already!). Though I may not always respond, I do love hearing from all of you and seeing that you're enjoying the series. It motivates me to continue writing more. You've all been wonderful and I can't thank you enough for all of your kind words and encouragement and yes, even the constructive criticisms!

Before I sign off, I've one last thing to say. It's been a rough few years, and in times like this, it becomes very easy to give in to anger and let that rule your life. I ask that, instead of letting anger run your life, take a breath, ask yourself if anger is really best in this moment, and if it isn't, try to consider putting some kindness out into the world instead. It's a rough world out there these days, and while that doesn't look like it will change anytime soon, it doesn't take much to make it just a little bit better. Please be good to yourselves, and to everyone else.)