Senior Year Memories: Mrs. Pruitt (Patreon Exclusive Story!)

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

Hello my wonderful patrons! As this month's second Patreon Exclusive Story, I am quite excited to get to share this tale between Ryan and one of everyone's favorite MILFs, Mrs. Cassandra Pruitt! To all of you who voted for her in this story (and to those old-timers who helped create her), I can't thank you enough for your votes and support! As ever, I hope you enjoy reading it as much as I enjoyed writing it!

And, yes, if you're wondering in advance, this one definitely does involve Mrs. Pruitt indulging in one of her favorite kinks. If you're into it, enjoy; if you aren't, here's your warning.

-aimingtomisbehave33

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During senior year, sometimes sex came from a girl pursuing me, sometimes it came from me pursuing a girl, and sometimes it just came from good, old-fashioned happenstance.

In one of my more favorite of those latter instances, this particular encounter came about because we’d run out of flour.

It was my fault, really; I’d promised to bake some cookies for a get-together we were having in the Puma Press offices to finish off the next issue without actually checking to see if Dad had picked any up recently, and when I went to go get started, I found we were empty. It wasn’t an end of the world level problem, since I had a couple days to get them ready, but it did mean that after a long day at school I’d have to hop on my bike and swing on by the store to get some.

Thankfully, the store wasn’t that far off, and a few bucks lighter for my trouble, I soon had a bag of flour stashed in my backpack and was prepared to pedal on back home to get to some baking.

It was as I was pedaling across the parking lot on my way back, however, that I spotted the familiar sight of a beautiful, raven-haired woman loading up the back of an SUV with bags of groceries that she’d placed on the ground. Wearing a long, flowy dress, her long tresses held back with a simple tie, she may have looked more plain “mom” than the more glamorous (and less clothed) moments of hers I was more familiar with seeing, but that didn’t mean I didn’t feel a familiar stirring inside of me simply at the sight of her. I didn’t have to do anything… but the strong feelings she brought out inside of me had me hesitate for less than a second before changing course across the lot, swerving up behind her and slowing.

“Hey, Mrs. Pruitt!” I called out to her.

Turning to face me, I saw that beautiful face break out in a familiar smile, one of fondness and almost motherly pride… but also something distinctly more. A faint look of lust passed over her face, one that was unmistakable and every bit as familiar as that smile.

“Hey, Ryan…” Mrs. Cassandra Pruitt said, running her eyes over me thoughtfully. “Funny meeting you here.”

Though she was 37-years-old, Mrs. Pruitt had a youthful beauty to her that had me often thinking that she could have been her daughter, Kaitlyn’s, sister. Her narrow, gorgeous face may have seen more years to be sure, but her expressive, deep brown eyes and full, pouty lips gave her a look that fell somewhere between otherworldly beauty and porn goddess. She wasn’t wearing much in the way of makeup today, but her pale skin looked every bit as soft and touchable as ever.

And as she looked my body over, I’d be lying if I said I wasn’t checking her out as well. The flowery dress the 5’4” stunner wore was loose, but not enough to hide the fact that she had some serious curves… or my memory of what she looked like without any clothes at all. With tight, long legs leading up to a firm, round ass, well-toned abs and impressive DD-cup breasts, Mrs. Cassandra Pruitt was undeniably a knockout, the kind of woman that most men would be fighting over for even the slightest moment of her attention, and that I’d had some seriously intense sex with back during her “book club’s” annual getaway.

Memories of that weekend, and what the two of us in particular had done together, gave me this distinct feeling like my cock might burst through my pants at any moment. That didn’t happen, because my life, while improbable, still hadn’t gotten around to working on cartoon logic just yet, but given how overwhelming Mrs. Pruitt’s hotness could be it did seem thoroughly possible for the laws of my own reality to rewrite themselves as it felt convenient.

Until then…

“I could say the same of you… but since this is the best store in town, maybe it’s not that funny?” I suggested.

Mrs. Pruitt giggled to herself softly. “Oh, I don’t know… I can appreciate the occasional coincidence, especially when it means I get the chance to see you.”

“Same,” I replied, unashamedly checking her out. “You know, I still find myself thinking about the book club getaway… everything that happened there… that was crazy, wasn’t it?”

“Feels like ages ago, doesn’t it?” she suggested, sighing.

“Thoroughly,” I said, grinning. “I hope you’ve been managing well since?”

“Oh, life is life,” Mrs. Pruitt explained. “You probably know more of what’s going on in Kaitlyn’s life than I do, and things with the husband, well, they are what they are. I trust you’re doing well?”

“I mean, school’s busy, and when you toss in trying to date a few girls at once and having an active sex life beyond that, well…” I said.

She chuckled. “Oh, yes, poor you.”

“I never said poor me. I was just getting at it being a lot of juggling… not unlike you with those grocery bags there. Need a hand?” I asked.

Putting the last few bags in the back of the SUV, Mrs. Pruitt closed the door, then smiled at me. “I think I’ve got this.”

“Oh, well… maybe next time, then,” I said.

“Maybe…” she replied coyly, looking around. “Say, you wouldn’t happen to need a ride home by any chance, would you? I know it’s a bit of a ride from here, and I wouldn’t want you all tired out for whatever else you’re getting up to today.”

“I’ll be fine,” I promised, before replying. “But I won’t say no to a ride if you’re offering.”

“Oh, I’m offering,” Mrs. Pruitt replied almost gleefully. “You can mount the bike on the rack in back, and if you really want, I can blow you before we get going.”

Her offer took me aback for a second, but I couldn’t help but ask, “Yeah?”

“I mean, if that sounds like it’d be something you’d like?” she suggested, raising an eyebrow.

“Oh, it sounds fine by me…” I replied.

“Good,” Mrs. Pruitt said. “Because I haven’t gotten what I needed in a while, and I am desperate for some cum. In my mouth, elsewhere… I just need it.”

“Well, you’ll get it, then,” I said.

“Good,” she replied, smiling sweetly and cocking her head. “I need to return the cart, but the car’s unlocked; grab shotgun, and I’ll be there in a second.”

I might have set a record mounting my bike on the back of her SUV, running like the wind for the passenger seat as I set my backpack at my feet. Mrs. Pruitt joined me not long after I’d sat down, closing the door behind her and smiling seductively at me.

“I’d apologize for the brazenness, Ryan, but I have wanted you for some time since book club,” she said, looking down at my growing bulge with anticipation. “Pull your cock out…”

I might have been overly cautious, but I asked, “Don’t you want to go somewhere more… private first?”

“I should, but I’m hungry, and I want you now,” Mrs. Pruitt mewled, reaching over and squeezing my cock through my pants. “Come on, I need it, and you need it, why don’t we get it together? Might help take some of the edge off before we get down to anything else…”

“Anything else?” I asked.

Grinning as she worked at my belt, she explained, “Look… I’ll say that this is going to start with a blowjob, but then once I’ve gotten a nice helping of cum down my throat, I can’t stop there. Sucking your cock will lead to one or both of us getting naked, and if that happens, you know we’ll be fucking in the back of the car, and when we do that, all bets are off… especially if we start about my favorite kink that you know gets me going so deliciously. If we start talking about my little fantasy… then I’ll probably lose all control on you.”

I arched my back in my seat to better help her undo my pants, liking the thought of Mrs. Pruitt losing control. It wouldn’t take all that much to do it… I knew that she got particularly hot and bothered when talking about her kink for getting impregnated, and if that was what it took to take this to the next level, I had absolutely no problem doing it.

Until then, though… I quickly looked around, finding the windows tinted enough to not have to seriously worry about getting caught, and now satisfied that we had a fair amount of privacy, found myself looking forward to getting blown by one of the hottest women I knew.

Mrs. Pruitt tugged at my underwear like she was ripping through the wrapping on a Christmas present she was particularly excited for, freeing my thick, ten-inch-long erection in no time. Leaning in as she was, she couldn’t help but be hit on the cheek by freeing it, something that caused her to laugh to no end.

“Oh, god… oh, this is so fucking perfect… oh, Ryan, I’ve been missing you… you and your huge fucking cock…” she said, taking my erection in her hand and stroking me enthusiastically.

Though my precum wasn’t flowing yet, that wasn’t stopping Mrs. Pruitt, as she quickly leaned in and kissed my cockhead, swirling her tongue over the tip as she looked me in the eye. I groaned at this utterly overwhelming feeling of pleasure, running my hand through her raven locks and enjoying the smooth feel of her hair slipping through my fingers.

“I’ve missed you too, Mrs. Pruitt,” I replied, gently thrusting into her mouth. “So fucking much.”

She groaned as the cockhead slipped between her lips and stretched them obscenely, but soon let me pop from her mouth as she smiled up at me playfully.

“Yeah? You’ve missed this? You’ve missed all this motherly attention?” she teased, licking underneath my cockhead with slow deliberation.

I moaned. “Fuck, I think you know I have… god, there’s no one like you, Mrs. Pruitt.”

“Well, I’m glad you agree with that… because I sometimes doubt my husband knows what the fuck to do with himself…” Mrs. Pruitt giggled, leaning in to slurp at my cockhead again. “But, fuck, if you’ve been missing me so much, why haven’t you gotten in touch? We could’ve done this a lot sooner, and a lot more…”

It was hard to come up with a lot of rational explanations while my cock was being sucked like this, so I simply replied, “I’ve been busy…”

“With all those other sluts, huh?” she asked, sounding playfully jealous as she sucked on my cockhead some more. “You could have been having me, and all this, all this time, and you were off fucking all those other girls… I should be offended by that…”

She and I both knew that that was something that could never actually happen, but I also knew well that she liked to fantasize and play act some when she got particularly horny. Seeing this ultra-slutty, submissive and jealous side of her was a fun look on her, and combined with what she was doing to my cock, well, you could say I was quite turned on.

“Forgive me, Mrs. Pruitt?” I asked.

Sighing overdramatically, she replied, “If I must, Ryan…”

She smiled a silly, broad smile, then simply leaned in and inhaled my cock. With one suck, she managed to get just over half my length down, and with some concentrated bobbing, she was soon inhaling my entire length.

“Holy fuck!” I exclaimed, gripping her hair tightly and fucking up into Mrs. Pruitt’s mouth.

She didn’t respond to this, gagging and gurgling as she fucked my cock deep down into her throat. Whatever character she was putting on, her urgency and need for me was quite clear and very real. She wasn’t teasing anymore, this wasn’t some drawn out play we were acting out, no, she was fucking me with her mouth and throat and she wouldn’t be satisfied until I’d drained my balls down her throat.

At the rate she was going, that shouldn’t have been a problem. Mrs. Pruitt was so good at sucking cock, and so fucking hot, that I was sure she’d have me cumming in no time, which no doubt would have made her enjoyably smug. Like a lot of the MILFs of the book club, she seemed to take no small amount of pleasure in comparing herself to the rest of them, and while I wouldn’t go out of my way to rank them, I couldn’t deny that Mrs. Pruitt was painfully hot, and certainly ticked off a lot of my kinks. I mean, she had been one of my longest-term babysitters and a distinct mother figure in my life for so long, as well as the mother of one of my oldest friends… the naughtiness with her was off the charts, and it took a number of minor miracles not to pop off just at the sight of her.

Coming up for air, choking and trailing drool and precum between her lips and my cockhead, Mrs. Pruitt looked up at me and said huskily, “I want you to fucking cum for me, Ryan… I need a good snack to get me nice and ready for when we fuck… so if you’re holding back on me, I want you to stop right now, understand?”

Smiling down at her confidently, I gripped Mrs. Pruitt by the hair and pulled her back down, forcing my cock back into her mouth.

“Oh, I understand… and keep going like that, and you’ll get one soon… fuck, your mouth feels so amazing, Mrs. Pruitt… you’re fucking amazing… god, if you get me off like this… I’m going to make you cum so hard, so fucking many times… please, keep going, I’ve got a big load building up, and it’s all for you, all yours, please, just keep blowing me… keep blowing me and I’ll cum deep down your slutty fucking throat in no time, just… oh god, don’t stop!!!” I exclaimed.

Insatiable as she was, there was no chance that Mrs. Pruitt was going to stop. With one hand gripping the base of my cock and the other teasing my balls, she sucked my cock at a blinding pace, her head bouncing up and down in my lap rapidly. Gripping her hair more tightly, I fucked back into her, utterly using her mouth as she lost herself in this frenzied blowjob. Pleasure began to overwhelm me as my balls swelled, and before long, the inevitable occurred.

“God, it’s gonna be soon, Mrs. Pruitt…” I groaned, thrusting up into her. “Keep going and you’ll make me cum… gonna make me cum… cum… cumming soon… cumming… CUMMING!!!”

I warned her as best as I could, but she only seemed to take it as a challenge. Mrs. Pruitt only sucked my cock harder and harder, milking the orgasm out of me until I simply had no control over the matter. When I came, I came hard, grunting and filling her mouth with cum as she gulped it down lusciously, trying to keep up with my massive flow and mostly succeeding. Her cheeks bulged occasionally as she gulped down my cum, some of it leaking out of the corners of her mouth and down her chin, but as a woman who knew how to seriously suck cock, she managed to keep things from getting too messy.

I collapsed into my seat, pleasantly drained as the last vestiges of my orgasm left me, while Mrs. Pruitt sucked up the last few drops. Sitting up, she smiled, wiping my cum from her chin with the back of her hand and licking it clean, before smiling at me.

“Thank you… I have needed that,” Mrs. Pruitt laughed, taking a sip from a water bottle and swishing it around to clean her mouth out.

Still catching my breath and finding myself in disbelief from the power of that orgasm, I said, “You’re thanking me? Fuck, that was awesome.”

Taking another long swig, she replied, “Well, good, because that was really to take the edge off for you… I want to take my time when things get messier.”

Mrs. Pruitt’s tone became distinctly more mischievous with that last word, her smile growing playfully in a way that made my cock twitch.

“So, your place, or mine?” I asked.

She thought about this, shivering slightly. “I’ll be honest, I could do either, but there’s something so naughty about car sex and blowing you here like this… I want to go find someplace nice and private and fuck in the back. If that’s alright with you?”

Grinning, I replied, “Oh yeah… that sounds very alright.”

***

While I thought on where we might find a certain amount of privacy, Mrs. Pruitt was far ahead of me, driving us over to the nearby Blair Valley Shopping Center. The closest mall to Regan Hills wasn’t exactly a happening place anymore, and had enough problems going on inside that nobody would really notice anything happening outside. Pulling into one of the more out of the way and isolated parking lots, she parked, then stepping out so she could rearrange things in the back of the SUV. With the seats folded down, we had a good, long stretch of a flat surface that, while narrow, was positively bed-like, especially once she relocated some of the grocery bags to the passenger seat up front and stretched a blanket out over its surface.

I lay down in the back while she rearranged grocery bags up front, stripping down and pushing my clothes aside until I lay naked and waiting for her. My cock was back to full hardness quite quickly, which wasn’t much of a surprise with Mrs. Pruitt waiting on me eagerly, and I was looking forward to being able to repay that blowjob imminently.

Finally satisfied up front, Mrs. Pruitt opened up one of the side doors and joined me in the back, getting onto her hands and knees next to me and looking down over my nudity.

“Oh, fuck, Ryan… you’re positively hot… fuck, I feel like I could eat you right up,” she purred, pulling her dress over her head.

I watched her strip down with interest, seeing her lean body exposed to me once again, from her magnificent ass to her full, round, DD-cup breasts. Though still clad in a simple, matching dark blue bra and panties set, my mouth watered at the sight of her, knowing full-well what lay beneath her last garments.

“I think if we’re comparing who’s the hottest in this car, I’m quite far from first place in that competition,” I said, eyeing her hungrily. “Holy fuck you’re beautiful, Mrs. Pruitt.”

She grinned at me, climbing on top of me and kissing me. “So, it’s Mrs. Pruitt today?”

I grinned, reaching up to squeeze her bra-clad breasts. “If that’s cool with you? I can call you Cassandra, if you’d like, but I know how dirty you like it, and I like it pretty fucking dirty too, so… yeah, there’s something about calling you Mrs. Pruitt that really gets me hard.”

“I can see that,” Mrs. Pruitt purred, reaching down and stroking my cock. “My, my, my, you are a big boy, aren’t you?”

I pulled her in for a kiss. “Oh, you know that better than most.”

“Maybe I do…” she said, grinding her underwear-clad pussy against my cock. “Very well, if calling me Mrs. Pruitt gets you off any harder, I won’t stop you… but you’d better prepare to get nice and dirty for me, too.”

“Oh, you know I’m always happy to get dirty for you,” I growled, reaching behind her and unclasping her bra.

She giggled as I did this, getting up on her knees just enough to shed her bra and push it aside. Her large breasts now bared to me, her nipples hard and begging for attention, I couldn’t help but lean in and feast, suckling on her sensitive nubs hard, giving some deliciously firm pressure while swirling my tongue and making sure I gave her the exact pleasure she needed. Mrs. Pruitt moaned and groaned above me, grinding more insistently against my cock as she did so, her hips writhing against me with expert precision.

“Mmm, and you know just how dirty I like it… fuck… my husband, that’s not the kind of thing he can get into, when he can get into it… he doesn’t understand my dirty side like you do… he doesn’t understand that I need to be more than a wife and mother sometimes… that I need to be used like a dirty whore, that I need a big cock pounding me in every hole and filling me up…” she moaned, looking down at me.

Then, with a devilish grin, Mrs. Pruitt grinned down at me and stroked my hair. “…he’ll never understand my kink for being bred like you do… but you get me, don’t you? Because it gets you nice and fucking hard fantasizing about getting me pregnant, doesn’t it?”

I couldn’t deny a certain thrill coursing through my body at that point, my cock jumping as I thrust up against her in a way that made her squeal with joy. I’d have explained this better if my mouth wasn’t full of nipple at the time, but given its current state, you can understand my lack of eloquence.

Of course, I also didn’t want to forget to return the favor from that amazing blowjob earlier, and while our current position didn’t allow for the easiest access for me to go down on her, that didn’t mean I was without all the tricks I knew. Still suckling her tits, I slid a hand down her toned stomach and under her panties, savoring the feel of her landing strip before reaching her hot, wet, pussy lips.

Mrs. Pruitt groaned on top of me, rocking her hips to give my hand better access as she looked down at me hungrily.

“Oh, my, my, my… you’re eager, aren’t you?” she asked, rocking her hips against my hand.

“Of course… you don’t think I’d let a blowjob that amazing go unanswered, would you? No, before we get down to anything else, I am going to make you cum, Mrs. Pruitt… I’ll make you cum so fucking hard that you’ll be wet enough that I’ll be able to just slide my cock right inside of you without a bit of trouble,” I said, grinning up at her as I began to finger her clit.

Mrs. Pruitt bit her lip, moaning and rocking against my hand more aggressively. “Fuck, Ryan… that’s… mmm… you’re fucking perfect, you know?”

“I’ve heard this before, but that doesn’t mean I don’t like to hear it more,” I replied proudly, pressing my fingers against her clit and running them around in quick circles.

Even though lying in the back of her SUV wasn’t the best way for us to get into a number of positions, there was a certain thrill to the improvisation of the moment, especially combined with the semi-public nature of our exploits. This may have gotten me more hot and bothered than a relatively cramped position like this would normally allow for, and made fingering Mrs. Pruitt while she was on top of me particularly exciting.

That she really got into it certainly didn’t hurt matters either.

“Oh, god, Ryan…” Mrs. Pruitt moaned, rocking her hips against my hand. “That’s… mmm, not what I was hoping for, but it’s good… it’s so fucking good…”

Enjoying her pleasurable distress as she continued to writhe on top of me, I asked, “Well, if that’s not what you wanted, I can stop…”

“DON’T YOU DARE!” she cried out, pinning me down and looking at me with the sexiest, harshest eyes. “I mean… it’s good, but if I want to get fingered, I can just call up one of the girls from the book club… but you’re doing a great job and, I, mmm… fuck, it’s really hard to put together thoughts… sentences when you’re doing that… just, keep going, keep fucking going, please, it’s good… keep doing that and you’ll make me cum, I’m so fucking hot right now…”

I grinned, kissing her deeply as I continued to finger her. That I knew how to pleasure Mrs. Pruitt physically was something I didn’t question, as I had learned quite aggressively over the book club getaway every little button that would set her off and make her cum screaming… but the give and take of the mental aspect was something I was still getting a handle on. I’d learned over the course of senior year that some women genuinely just wanted raw, physical passion right now, while others needed more of a mental aspect to properly get going. Mrs. Pruitt definitely fell into the latter category, as although she could become a cock-hungry slut like the rest of her friends at a moment’s notice, the way to get her off the hardest, I’d found, was in taking her to the place she needed to be mentally to properly get going. Beyond just her impregnation kink, she could also be very submissive, wanting me to take charge and dominate her.

While it wasn’t the easiest task in the world, I’d somehow managed to do that while she was on top of me, which was certainly an exciting achievement for me today.

“You look fucking sexy like this,” I growled, kissing her again.

“Only because… only because you bring it out of me… ohgod… I’m so hot, so wet right now… you’re gonna make me cum, aren’t you?” she asked, blinking down at me as she looked on with hope.

Smiling my dark, dominant smile, I slowed my fingering of her clit and said, “Well… maybe I will, maybe I won’t… I haven’t decided on that yet…”

Mrs. Pruitt’s eyes flew open, needy and a bit frightened at the prospect that I might not make her cum. Without another word, I kept smiling, then fingered her even harder, speeding the circles around her clit as she moaned and cried out without restraint. The car windows seemed to rattle as I got her louder and louder, fingering her increasingly soaked cunt until I knew she would have no choice but to surrender to me.

This didn’t take very long, as after only a couple minutes at this increased pace, her muscles tensed and she rocked the car with the intensity of her orgasm, crying out. Her juices flooded all over my hand, utterly soaking her panties as I continued to finger her, loving the sight above me as the gorgeous MILF lost all control under my fingering.

I could have watched her shudder and wail like this for hours, but soon she couldn’t help but give out under the power of her orgasm, falling on top of me and panting as she begged quietly for me to stop. I didn’t want to, but I also didn’t want her to be overstimulated, either, so regretfully I pulled my fingers out of her.

Quickly, I grabbed Mrs. Pruitt and rolled over so that I was on top of her, forcing the fingers that I’d used on her pussy into her mouth. She sucked them luxuriantly, taking every drop of her delicious juices from me, and then continuing to lick and suck them just because it seemed she enjoyed licking and sucking whatever I put in her mouth. I groaned at her impeccable oral skills, smiling down at her before pulling my fingers out and kissing her.

“Oh… oh, that was good, Ryan… you were bad, but that was soooo good,” Mrs. Pruitt giggled, kissing me again.

“Well, what can I say, you have a way of bringing out my dominant side,” I said, kissing her and grinding my cock against her leg. “I trust that’s not a problem for you?”

“Oh, fuck, hardly,” she laughed. “I have to be too damn responsible too much of the time; get me behind closed doors and I’ll happily be your sub-slut. Throw me around, hurt me a little, fuck me until I can’t walk right… god, I love it… fucking use me…”

Laughing again as she heard herself talk, Mrs. Pruitt continued, “Ah, fuck, when I was young, all I wanted to do was be independent, now that I’m independent, all I want to be is responsibly used. I might have to talk to a therapist about that.”

“I’m sure it’s normal,” I said, kissing her. “God knows I’ve heard the same from your friends. It’s probably one of those things about perspectives changing with time, but I’m hardly an expert, so, I dunno. I wouldn’t stress about it if I were in your shoes, but, hey, mental health being what it is, you do what you gotta do for yourself.”

Smiling, she kissed me, before reaching down to try to shuffle her way out of her panties. “Well, then, since there’s nothing that wrong with this, I’d say I’m just about ready for a little extra irresponsibility.”

Raising my eyebrow, I asked, “Oh yeah?”

“Yeah,” Mrs. Pruitt giggled.

“How much irresponsibility?” I asked, shifting my position to better help her get naked.

“Well…” she replied, nibbling on my neck, then whispering into my ear, “Bury that cock in me and fuck me until I scream… and I mean scream… I want you to use my body however you want, fuck me as hard as you want, and cum inside me… I want to be drained, and I want to be filled… fuck, I want to be filled so much I’ll have no choice but to be your knocked-up slut by the time I get home… how’s that for irresponsible?”

“That’s… pretty fucking irresponsible,” I said after some thought. “And one I can thoroughly encourage.”

Grinning, Mrs. Pruitt took hold of my cock and stroked me eagerly, spreading my precum around nicely before she lined the head up with her pussy. She bit her lower lip as she did this, stuck in concentration, but her enthusiasm was so high that not even a moment’s concentration could hold her back for very long. She ran my cockhead over her pussy lips, spreading our juices, combining them and making sure we had a nice mix of natural lubricants ensuring this next part could get as messy as we needed it to.

“I’m glad we’re in agreement on this…” she continued, leaning particularly hard on her playful, whiny tone, “Now come on, Ryan, pleeeeeeease fuck me?”

It’s hard to explain exactly what her submissive side did to me, but it made my cock feel about as hard as it had ever felt, and all too easy for me to thrust forward and lodge my cockhead between her pussy lips. Mrs. Pruitt cried out pleasurably, wrapping her legs around my ass and pulling me forward, helping me (not that I needed the help, honestly) slide my cock inside of her until every one of my ten inches had disappeared. As ever when I had this delicious opportunity, I took a moment to savor Mrs. Pruitt’s tight, hot, wet cunt as it embraced my cock, squeezing me possessively as we became accustomed to each other and the feeling of our bodies against one another. Feeling her toned softness against me, with the swell of her breasts against my chest and that hot, squeezing sensation around my cock, I’d have been in heaven enough already, but looking down into her beautiful eyes, seeing her smiling up at me so serenely as if there was no place on Earth she would rather be… well, it was a pretty fucking sublime feeling.

I did what felt natural and leaned into her, making out furiously with the mother of the girl who’d taken my virginity. It was madness, I knew, that the two of us would get together like this, but when we did, nothing in the world could feel better. The intense history between our two families only made this situation naughtier, as I was now buried balls deep in one of my first crushes, readying to give her the fucking of a lifetime yet again as we had so many times at the book club retreat.

Content that we had savored this moment long enough, I pulled almost all the way out of Mrs. Pruitt, then thrust inside of her, burying myself completely inside of her with a swiftness that had her crying out in pleasure. It didn’t take long to develop a pace like this, making this fuck fast and wild as I gave myself over to my lust.

Not that I was the only one.

“YES!!!” Mrs. Pruitt cried out, rather enjoying the way we got her SUV rocking. “Oh, FUCK YES! I love it! I love it so much! Please fuck me harder, Ryan, I want it, I need it… I can take it! Fuck me, Ryan, fuck me harder… god, fuck, I never imagined you can be so good… so glad to know, so glad we can do this, god, your cock, it’s amazing, it fills me up so well, keep giving it to me, please, give me more of that fucking cock!!! Fuck, I’m so fucking glad Kaitlyn found you!!!”

I laughed, kissing her and groping her breasts with one hand as I did. “I’m sure… I was off the table until she seduced me… and then… holy fuck… you know how it went…”

“Uh huh…” she groaned, smiling and running a hand over my chest. “Though if I’d have known how hung you were, I’d have probably beaten her to it… made it the best goddamn belated 18th birthday present you’d ever had… holy fuck, keep going, keep going, keep fucking me, keep… give it to me, fuck!”

“So tight… so good… fuck, you’re so fucking hot,” I said, pumping into her at a blinding pace.

“Yeah?” Mrs. Pruitt moaned, locking her ankles behind my back to keep me fucking her.

“Oh, you know how hot you are,” I grunted. “You can feel my enthusiasm buried deep in you, can’t you?”

“Yeah, but as ladies like me get older, we like to hear it more and more… you’re not the only one who likes praise, after all. I may not be attracting the same kind of attention I’m accustomed to these days, but I certainly like it from you,” she replied cheekily, kissing my neck.

“Well, that’s a damn shame, because you’re one of the sexiest MILFs in the world, I’d bet… fuck, you’re so beautiful, and your body could make any man hard… these tits, that ass…” I groaned, continuing my rough, swift pace.

“Don’t forget this sweet, MILFy cunt…” Mrs. Pruitt responded playfully, squeezing me as I fucked her. “This cunt knows how to get the job done!”

“Don’t I know it…” I replied, my cock twitching inside of her. “You can feel them, can’t you? My balls swelling, getting ready to fill you with that potent cum that makes you scream and cry out in ecstasy so deliciously? Yeah, you drained them earlier, and you’re so fucking hot, so fucking good at this that you filled them again… filled them again so I can’t help myself but go crazy on you… fuck… so fucking crazy on you that I won’t be able to help myself soon, and that’s when bad things happen…”

“Oh?” she asked, raising an eyebrow. “What kinds of bad things?”

“Well, things like me being unable to stop fucking my good friend’s mom… where I can’t help myself but fuck you until you’re a screaming, cummy mess, and I can’t help but shoot my load deep into your waiting cunt… shooting a load so thick, so deep that you can’t help but get pregnant by the time we’re out of this car… those kinds of bad things…” I explained, my voice darkening as I progressed.

Mrs. Pruitt shivered, holding onto me tighter. “Oh, fuck, Ryan… you know how to talk to a lady…”

“Uh huh…” I agreed, pumping more firmly. “And you know how to take cock… feels so good…”

“Believe me, not as good as this feels…” she groaned, tightening her legs behind my ass. “I won’t last much longer, please… give it to me harder… come on, Ryan, give it to me harder, give me that thick cock, give it to me, please, I’m so close, you’re going to make me cum…”

I had to admit that she wasn’t the only one in this state. “Oh god, me too… this is going to be a big one…”

“Yeah? Got a nice load for me? Got a nice load to fill my needy cunt with?” Mrs. Pruitt asked, moaning lusciously as she rocked her hips against me.

“Yeah… holy fuck, yeah, it’s… god…” I groaned, losing myself in the moment, pounding into her with a greater ferocity as words abandoned me.

Thankfully, she caught my meaning well, moaning and keeping pace with me. “That’s it, right there, keep going, harder, like that, fuck, keep going, I can feel you swelling, and I need you to do that for me, need you to give me that cum… cum for me, Ryan, cum with me, fire it nice and deep, give me every drop… I need you to knock me up… get me pregnant… fucking breed me, Ryan, come on, I need it, I need it now… you’ll help fill my hot MILF cunt up, won’t you? Pleeeeeeeease?”

Fuck, there wasn’t a lot that delightfully whiny, needy tone couldn’t get me to do, and at this point, I was too far gone to do anything but give her that thick creampie she needed so badly. My hips a blur, I gave her every last bit of energy I had before I cried out in pleasure, burying deep inside of her and cumming, hard. Mrs. Pruitt exploded in her own matching ecstasy, shaking and bucking beneath me in her own orgasm as she held onto me tight, making sure I gave her every bit of cum she could drain from me. Fortunately for her, it felt like I had an absurd amount to give in that moment, flooding her pussy with a thick, creamy load that seemed to only set her off even harder.

Mrs. Pruitt gripped to me tightly, making sure to look me in the eye as we rode out our mutual orgasms with each other, reforging that intense bond that we had shared throughout the course of that unforgettable weekend with the book club. It was a pleasure that felt like it would go on forever, with the two of us locked away in the back of her car like this, but as with everything, we were soon taken in by that fall back to reality that comes with the clarity after an orgasm.

Collapsing into her, I kissed Mrs. Pruitt deeply, as she kissed me back with equal passion. These kisses were slower than our fevered, frenzied kisses from moments before, but as we calmed down and realized where we were and what we were doing, we couldn’t help but smile at each other, exchanging slow kisses as we chuckled and caught our breaths.

“Ahhh… fuck,” she giggled, loosening her grip around me. “That was good… really good. I was afraid for a moment I might squeeze the life out of you, I was cumming so hard.”

“Life? No. All my cum?” I laughed, looking down between us at the mess between her legs. “Yeah, I’d say you did a great job squeezing all that out of me.”

“Well, I’m not sorry,” Mrs. Pruitt sighed pleasantly.

“Who said anything about sorry?” I asked, trying to push myself off of her. “Ummm, I think you’ve got me locked in here.”

Realizing her ankles were still tight around my ass, she laughed softly, “Well, I gotta make sure to keep that cum nice and plugged in there if I want you to knock me up, don’t I?”

Laughing, I kissed her, and she finally unlocked her heels from behind me. Achingly, I pulled out of her, crawling down Mrs. Pruitt’s body so I could take a moment to suckle on her nipples.

“Ahhh… fuck…” she replied, her eyes rolling back.

Seeing that look on her face as I alternated between her breasts, I grinned. “I bet these got fucking huge when you were pregnant.”

Mrs. Pruitt laughed. “I mean, you know that big tits run in the family… Kaitlyn, me… fuck, my mom’s are still fucking huge, but, yeah, I’m sure if you actually did knock me up, they’d get even bigger… oh, fuck, your mouth feels so fucking good on me… my daughter’s lucky she gets you as often as she does.”

“Well, I’m lucky to know her… know both of you,” I replied. “Even beyond all the sex.”

“But the sex is fucking awesome,” she replied, laughing and running her fingers through my hair as I continued sucking her tits.

“Oh, definitely,” I replied, finally crawling back up her so I could kiss her, before I lay down on my back next to her.

Mrs. Pruitt wrapped my arm around her shoulders, and I held her in close.

“All fantasies and kinks aside, this… this is really nice,” she replied, smiling up at me.

“Seriously,” I said, kissing the top of her head. “I mean, the hardcore sex, that’s always great, but sometimes I think that this afterglow moment is seriously underrated… just holding each other, basking in all the wild sex and just feeling that high rolling over us?”

“Yeah, there’s nothing like it, really…” Mrs. Pruitt replied pleasantly, if a little sadly. “I don’t get it as much as I’d like these days, sadly… book club meetings aren’t as common as they could be, and god knows I’m not getting it at home like I’d like… I’m honestly grateful for your time. This is… well, it’s nice to indulge the sides of myself that I don’t get to tap into all that often. I know what we’re doing is particularly naughty, and that’s where a lot of the excitement comes from, but you’re a good guy, Ryan… ladies like me need guys like you a lot more than they get them, and I just want to reiterate how thankful I am for whatever of your time you are willing to spend with me. You really know how to make me feel young and crazy again.”

“Yeah?” I asked, smiling at her fondly as I kissed her again. “I’m… well, I’m glad to hear it. I wish I could say something comparable… I guess I’m still getting used to feeling wanted by women, and when they’re as hot as you? It’s kind of awe-inspiring, if I’m honest.”

Rolling over onto her front, propping herself up on her elbows so she could eye me better, Mrs. Pruitt said, “And you don’t think you’re awe-inspiring?”

“I mean, I know people still consider some of me to be,” I said, looking down at my mostly deflated cock and chuckling. “But there’s times I still feel like the me that started this year rather than the me I’ve become, and it’s hard to feel that inspired by that side of me. I know that me’s gone, but… I still need reminders of it sometimes, I think.”

Smiling warmly, Mrs. Pruitt pushed herself up on her elbows, showing her bare breasts to me. “And how are these for a reminder?”

I raised an eyebrow, pleased at the sight, and enjoying the feeling of life returning to my cock. “I mean… yeah, that’s definitely a good start… I think I’m remembering who I am now more distinctly.”

The playful sarcasm may have been thick in my voice, but Mrs. Pruitt seemed to enjoy the challenge.

“Really?” she purred, running a hand down my body. “I guess I’m going to have to show you just how awe-inspiring I find you then…”

“Oh yeah?” I challenged.

Kissing her way down my body, Mrs. Pruitt found her way between my legs, kissing my cockhead and smiling at me. “So, you want me to tell you in great detail about how I find your cock to be the biggest, most exceptional cock I’ve ever seen in my slutty life?”

“I mean…” I groaned, dropping my head back as she suckled on it for a moment. “If you want to stroke my ego, that’s certainly a good way to go about it.”

“Oh no, I’m not here to stroke egos… I’ve got better things to stroke,” she giggled, jacking enough life into my erection that I was hard again in no time.

Cassandra Pruitt… she was almost supernaturally good at this.

“Better things like this titanic cock…” she purred, kissing and suckling on my cockhead again with a delicious swirling of her tongue. “…and this is truly titanic. You know I used to be a party girl when I was younger, and I’ve seen so very many cocks in my time… but none of them like this. None of them this good, this fucking huge. You’ve probably got one of the best cocks on Earth, Ryan, and the fact that I get it in my life (among other places)… well, that really makes me a lucky lady, doesn’t it?”

I could’ve argued with her here over who was the luckier one, but as she looked up at me with those deep brown eyes of hers and went to town sucking my cock, what can I say, she knew what she was doing.

Knowing she had me right where she wanted me, Mrs. Pruitt confirmed, “You’re ready to go again, right?”

“Oh yeah… maybe a little slower this time, while I recharge, but I’m definitely ready for more of you…” I said.

Climbing on top of me, she grinned down at me, reaching down to grip my cock so she could line it up with her pussy. She kept like that for a moment, squatting above me and teasing the head against her entrance, still dripping with both of our mingled juices.

“A little slower, he says?” Mrs. Pruitt teased, applying a little of her weight to my cock.

I groaned as she began to sink my cock into her pussy. “At first… it’s… fuck, just give me a moment, ride me nice and slow, and we can go as hard as you want in a minute…”

“Mmm…” she groaned, sitting on my lap with my cock completely inside of her. “I’ll try my best… it’s a challenge sometimes, restraining myself around you… probably for the best we don’t see a lot of each other in public, in that case, because I probably wouldn’t be able to stop myself from dragging you off to the first quiet place I can find where I’d get you to fuck me until it’s not such a quiet place anymore… fuckyou’rebig… but you asked nicely, and you’ve helped me cum so hard, that I don’t think I could turn down any request you’d make… fuck.”

Looking up at her and taking in her beauty, as ever finding myself in a position where it felt like I was seeing her for the first time, I ran my hands up her sides with the lightest touch. Mrs. Pruitt shivered at this contact, groaning softly as she took in the sensations. She closed her eyes for just a moment, dropping her head back as she moaned louder, then looking down at me with one of the most painfully sultry looks I’d ever seen. Reaching up, I squeezed her breasts, pinching her nipples ever so softly, yet with enough emphasis to get her moving.

“So, slowly, then?” Mrs. Pruitt teased, beginning to deliberately rise and fall on my cock.

“To start with, sure…” I said, dropping my hands to her hips and gripping her firmly, helping guide her in a pace on my cock. “…but if you really want to be my knocked-up slut by the end of all this, you’ll probably have to ride me nice and hard by the end…”

She groaned at my words as they tickled her kink, dropping down on top of me so she could kiss me. “Ryan… you really have a gift with that silver tongue you’ve got…”

Grinning, I reached up and squeezed her ass while we made out. I thought of saying something witty, or at least playfully sarcastic in the moment, but seeing how perfect the moment was, I didn’t want to ruin it. I wanted to enjoy whatever may come with Mrs. Pruitt while we were together, and see if we could get her car rocking even harder this time.

Honestly, seeing Mrs. Pruitt pick up the pace as she rode me, I didn’t think that would be much of a challenge.