My name is Ryan Collins. If you already know me, fantastic, pull up a chair and feel free to continue on with my adventures. If you don't, here's a little backstory to catch you up.
I turned 18 right before my senior year at Regan Hills High School, and because I was an almost friendless nerd I expected it to be a year like any other.
To my surprise, it's been anything but.
I thought I was doing a simple favor for my favorite teacher when I agreed to tutor cheerleader Kaitlyn Pruitt. Kaitlyn was an old friend I hadn't talked to since we were little, ridiculously hot, and a major league bitch who didn't want anything to do with tutoring. She offered me a handjob as a way out, and being that I'd never so much as touched a girl before, I took her up on it.
She didn't count on me having a ten-inch long and very thick cock.
I didn't count on her being so enamored with it.
The two of us had sex, and while that should've been the end of it, it wasn't. You see, Kaitlyn had friends, and those friends had friends, and my reputation sort of started to grow. I got to fool around with cheerleaders, teachers, Goths, band geeks and gamers and everything in between. I knew Regan Hills High had some of the hottest girls I'd ever seen, I just never knew how many there were. And how creative they were. It's been a year run by cliché and happenstance, and I'm willing to call myself a lucky fucking guy for the crazy experiences I've had.
I've had a lot of fun this year, made a lot of friends. Even found a girlfriend, who may be the kinkiest girl in a school full of kinky girls.
I've made some mistakes too, lost my best friend. That one still hurts.
The bottom line: I had a lot of adventures this year, some of which I haven't found a good way of fitting into my main story but still deserve telling.
This is one of those stories.
***
Generally, I've learned to seize opportunities when they come. After a lifetime spent thinking I wasn't good enough or that nothing good would ever come my way, senior year had taught me to seize the day. Sometimes that wasn't always the best approach, but more often than not I'd been rewarded for taking chances.
Sometimes, though, an enticing opportunity came up that gave me pause, because I had to weigh the pros and cons of something that could potentially blow up in my face.
Take the e-mail I received on that cold and wet Friday in winter.
"Ryan,
I hope this message finds you well. I've been thinking a lot about what happened between us back in November, the good and the bad. Though I could have done without the bad, I believe that ultimately more good than bad has come from it. Don has shown remarkable restraint in remaining faithful while vehemently encouraging me to take advantage of the "hall pass" he's granted me so I can better make up for the time he cheated on me.
Well, today I'm going to finally take advantage of that. I've gotten a room (# 402) at the Pinewood Hotel in Blair Valley, and will be there tonight after 5:30. I'm content to have the room to myself if I must, let Don's imagination run wild with what I might be doing, but if you're available I would enjoy your company. More if you'd be willing.
I know things between you and Tori have been strained of late, and I'll understand if that causes you to turn down my offer. I'm sorry that what transpired at Thanksgiving damaged your friendship as severely as it has, but I'm not sorry about what we did. You showed me more compassion and excitement than I've received in a long time, and we were two consenting adults who found a way to bring some happiness into each others' lives on an otherwise bad day. God knows there could certainly be more happiness going around these days. Tori may not approve, but since when does she completely rule our lives?
I hope to see you, but if I don't, I hope you have a lovely day.
Sincerely,
Lauren"
Lauren McNeil. Mother of my former best friend Tori. I won't go into agonizing detail about what happened, since I've gone over that one at length in my main story and don't want to linger on it any longer than I have to, but the short version's this:
Tori was my best friend, and I had a crush on her. I maybe also had a bit of a crush on her mom growing up, since she was hotter than hell. After my senior year got as crazy as it did, Tori and I had sex and I told her I loved her. She said she didn't want to be in a relationship with me, which I thought I was fine with, but when she wound up falling for a girl she met on Halloween, April Martel, I didn't handle things as well as I might've.
Mrs. McNeil was there to comfort me after I didn't take this news well, and since she was nursing her own bad news at the time with her husband, Don, cheating on her, we both kind of fell together and had sex. It was awesome, and certainly inventive, even if we both knew it was a terrible idea.
Flash forward to Thanksgiving, and I'd also befriended Tori's older sister, Rachel, and with one thing leading to another in the way my crazy life goes (and because I really liked Rachel), I wound up having sex with her at the McNeil house while Thanksgiving dinner was still in the oven. Tori found out I'd had sex with her mom and her sister and... well, things didn't end on a happy note. Tori and I weren't friends anymore, and I'd stopped holding out any serious hope that I'd hear from her.
I still fooled around with Rachel sometimes on Skype, but Mrs. McNeil... Lauren (it was so hard to know what to call her in my head sometimes after what we'd shared), she was another issue entirely, one that I wasn't sure I knew how to handle.
Unlike Rachel, who was more than a state away, Lauren lived only a matter of blocks away from me. I'd been over to her house almost as much as my own when I was growing up, and after we'd had sex I couldn't pretend I didn't want her anymore. I hadn't made any move to reconnect with her because I didn't want things to get any worse with Tori, but with things with her about as bad as they could get...
The e-mail gave me a lot to think about.
I had a rare Friday without plans, and memories of what had happened between Lauren and me back in November swimming in front of my eyes (made easier by the pictures of her in the Senior Year Memories album on my phone), I had to pro-con the situation to decide.
Pro: The sex would be great
Con: If she found out, Tori would want to kill me
Pro: Tori was already about as mad at me as she could get, so I doubted it could get any worse
Con: If she found out, Tori would want to kill me
Pro: I really liked Mrs. McNeil; she was fun to hang out with and talk to, and it had been a while since we'd last talked
Con: If she found out, Tori would want to kill me
Pro: The sex would be really, really great
Con: If she found out, Tori would want to kill me
It was a tough call, but let's be honest, you knew coming in here how this story was going to go, didn't you?
***
Okay, so, fun fact. Contrary to popular belief, even down here in Southern California we have seasons. They're random and they don't behave like they do pretty much anywhere else in the country, but they do exist. They even come in their own flavors: mild and apocalyptic.
The winter rainstorm that came as I rode my bike over to the Pinewood Hotel in Blair Valley fell under that apocalyptic description. It was cold, the drops were heavy and came in sheets, and as usual in this area, once it began to rain people on the roads lost their fucking minds. How I survived the half hour ride to Blair Valley is the kind of arduous adventure that Tolkien or Martin would talk about in lengthy detail, but since that's a voyage I'd rather forget I'll forego it in favor of getting to the part of this story I much prefer to remember.
The Pinewood Hotel was, on the outside, much less quaint and cozy than its name would imply and was more a five story, gray business hotel for on the go travelers who wanted to be near but not too near an airport. Though I got some odd glances as I chained my bike up underneath an overhang outside and walked through the lobby while soaked to the bone and shivering, I walked with enough purpose that nobody tried to slow me down or stop me.
Still dripping and half-frozen and telling myself that this had better be worth it, I rode the elevator to the fourth floor and found Room 402.
I knocked, and seconds later when the door opened, I knew that this trip had been entirely worth it.
"Oh my god, Ryan! Tell me you didn't ride your bike here!" Lauren McNeil said, her eyes wide as she looked me up and down.
While this would have been a perfect time for a witty retort, seeing her always had a way of taking my breath away.
Though in her early 40s, Mrs. McNeil took really good care of herself through a regular regimen of yoga and running. Matching my 5'11" height, her face had a youthful beauty to her that had always made her a lot more relatable than most moms. With flawless, porcelain pale skin and long, straight red hair that went to her middle-back, she was as stunning as ever. Though wrapped in a fluffy white bathrobe, it did little to hide the insane body I knew was there. DDD tits and an amazing, round bubble butt, all accompanied by a tight, fit body...
Yeah, she left an impression.
When words finally found me, I said, "I won't tell you that, then."
"Please, come in, come in!" she said, taking me by the wrist and guiding me inside, closing and locking the door behind us. For how Spartan the hotel appeared, it was a nice room with a king-sized bed, a large flat screen TV and windows that looked out over a dark and stormy Blair Valley.
She continued, If I'd have known you'd have tried to bike today, I'd have driven over, or sent you an Uber. Why didn't you get a ride?"
"It's surprisingly hard to grab a ride on a Friday?" I said, not wanting to admit that I just hadn't thought of asking for a ride.
"Well... that was foolish, but thank you for coming," she said, pulling me into a soft, warm hug. It was a warmth I liked, the kind that reminded me of good days before things had gotten complicated between us. Realizing I didn't mind the complications that much, especially with how welcoming and familiar the hug felt, I returned the hug with as much warmth as I was capable of.
"You're freezing, aren't you?" Mrs. McNeil said, letting me go.
"Little bit," I admitted.
She laughed. "I know I wanted to bring you here to seduce you, but when I suggest you strip down and take a shower now, that's the mom in me talking. We need to warm you up so you don't freeze to death in my hotel room (housekeeping would pitch a fit, wouldn't they?); get you under some hot water so you'll feel like a new man. Does that sound good?"
It sounded better than good, but I repeated, "Little bit."
"Come on," she said, wrapping her arm around my shoulder.
She looked good. She felt good. Fuck, she even smelled good.
I couldn't help but lean in and kiss her. It surprised her, briefly, but she soon kissed me back eagerly. Our tongues briefly grazed one another, tasting, probing, with no urgency or franticness and only a fondness and warmth for one another exchanged. It could have gone on longer, led to something more immediate, but with as much time as we wanted before us and no chance for interruption, there was something unhurried to it that I really liked.
Smiling at me, Mrs. McNeil said, "Come on, hop in the shower; I'll figure out something to do with those wet clothes."
"Thanks," I said gratefully, taking off my jacket and walking toward the bathroom.
***
She was right: standing under the spray of hot water really did make me feel like a new man. I don't know how long I was under the hot, steamy spray, but I was enjoying the nice, large shower/tub combo her hotel room had to offer. When I might have felt shaky and uncertain when I got here, a little time spent in the heat made me feel more like myself again.
Her kiss lingering on my lips brought back memories I really liked, and even if I'd been crazy to ride here, it all of a sudden felt very worth it.
I thought back to our encounter back in November. We had a good time. A really good time. The kind of time that brought my erection to life in all its glory. I really wanted to touch myself, but had to remember that Mrs. McNeil was there waiting in the next room, looking for-
The bathroom door opened. I looked through the clear shower curtain as Mrs. McNeil stepped in, closing it behind her.
"Wow, you've really worked up some steam in here," she said.
"They've got good water here," I said, trying to sound cool with my newfound vigor and confidence and utterly failing.
"Any chance you'd want an old lady to help you heat things up even more?" she said.
"You're not old; you're a goddess. And yes, I'd enjoy the company," I replied.
"Oh, you've still got that silver tongue," she said with amusement, dropping her bathrobe to the floor. When I'd first gotten in, part of me suspected that she wasn't wearing anything underneath, but seeing all of her pale, toned and absolutely naked body revealed... it was quite nice. Her DDD tits with their large, thick nipples and wide pink areolas looked positively mouthwatering, while the warm pink lips of her pussy were topped with a well-trimmed landing strip of fiery red hair.
"You know where you want me to put that tongue?" I asked, turning so she could better see my hardness.
Giggling softly, she slid the shower curtain to the side, climbed inside and said, "I can think of a few ideas..."
I closed the curtain while she stepped under the water, her pale skin flushing almost immediately as the hot spray coursed down her body. She ran her hands through her hair, making sure to get completely soaked, before turning with an impossibly sexy look. Looking so luscious my cock may have even grown a little bit extra, she bit her lip softly.
I couldn't say who made the first move, but we were in each others' arms in a flash, her tits pressed against my chest as my cock rested against her belly, the two of us making out furiously as months of pent up frustration and desire for more time together burst out at once. Our hands roamed over our bodies, though I couldn't help but grab her sweet, sweet ass. It was the perfect mix of soft and tight, utterly delectable, the kind of ass I wanted to bury my face in until she screamed (and, who knew, we might make that happen).
Mrs. McNeil rolled until her back was against the wall, then reached down and gently grabbed my cock, lining it up with the tightness of her pussy. I didn't need any further instruction, thrusting upward slightly and burying almost my entire length in her tight, hot, wet cunt.
"Fuck!" she groaned, grabbing my ass and pushing me even further until I was buried completely inside her. "Fuck I needed this, fuck I've wanted this... fuck, fuck that's so fucking amazing!"
"You're not so bad yourself," I said, savoring her wet warmth, lingering on how much like home it truly felt. "You're really wet."
Smiling, Mrs. McNeil kissed me. "Absolute honesty: I didn't know if you'd be coming here or not, so once I checked in, I got naked and spent some quality time with my Hitachi. My goal was to cum so many times tonight, tomorrow and Sunday morning that I lost count whether you came here or not."
Playfully, she squeezed my cock with her pussy muscles. In response, I slowly started thrusting in and out of her, making her groan. She continued, "Obviously, I love my well-worn Hitachi and how it can make me cum like just about nothing else ever could, no offense, but it lacks a certain human connection. I want to be fucked by someone who knows how to use their fingers, their mouth, their... cock, but more than that, I want to be fucked by someone I care about, and respect. In short, I really want to be fucked by you, which is why I'm very, very, very glad you were able to make it here in one piece."
"Me too," I replied, fucking her harder against the wall.
Now, if you've read my story so far, you probably know that I don't have the highest opinion in the world of shower sex. Screwing around while standing up is difficult enough as is, and with the added difficulties of everything being soaking wet and hotter than hell while trying to stand on a surface without the greatest traction, it can be less than fun. That being said, when you've got the right partner (especially one with some height on her so you don't destroy your knees), it's easy to get lost enough in the moment enough to ignore such problems.
Mrs. McNeil definitely fell under that "right partner" category.
"God, fuck me, Ryan, right there, like that, FUCK! I've missed this cock, I've really needed some serious cock like you wouldn't believe!" she exclaimed as I fucked her against the wall.
"Well, I've got that!" I grunted, holding on for dear life and thrusting into her as hard as I could.
"And now you've got a real woman's pussy. Best you're, FUCK! Best you're ever gonna find! Because I've got the experience, the fucking body, the skill, I'm built to fuck like none of those high school girls you're wasting yourself on and... FUCK!" she exclaimed as I reached down behind her, pressing the tip of my finger against her asshole.
"FUCK! You know what I like!" she said, her eyes blazing as she kissed me hard.
"And I know how to give it," I said, trying to match her level of cockiness. While normally one of the sweetest people you'd find, I'd found that Lauren McNeil had a habit of dirty trash talk when she got horny, and though I wouldn't talk shit about any girl I'd ever been with, I was willing to encourage this for how much fun she was having. Especially when her pussy was so tight, so sweet, her body such perfection that it might just drive me over the edge here and now...
This wasn't my ideal position for sex. I liked greater access to the body, and with someone pressed against the wall there is only so much flexibility. I was plenty warm by this point, and though I was definitely having fun, I was eager to transition us over to the bedroom for some real, serious fucking.
However, when properly motivated, I'd found my share of tricks to get things moving along.
While the two of us were properly braced against the tub, I kept one hand on her ass and dropped my other to her clit, fingering her vigorously while I continued to piston in and out of her. While she'd been moaning and crying out with ecstasy already, this only amplified her pleasure as I kept fucking her.
"Oh god, fuck, you motherfucker you're gonna make me cum, gonna make me cum you motherfucker..." she groaned, looking at me sternly yet hungrily.
"You like calling me a motherfucker, don't you?" I grunted, squeezing her clit slightly.
Mrs. McNeil squealed. "It's kind of apt, isn't it?"
"How's this for apt?" I said, slowing my thrusting just enough that I could give a renewed burst of energy with my fingers on her clit. It took all the self restraint I could to not just fuck her into oblivion and cum deep inside her tight, wet pussy, but since it seemed like she'd been looking forward to this even longer than I had, I wanted to make it memorable.
It worked.
"FUCK!" she cried out, her body going rigid against mine, then shaking uncontrollably as the orgasm overtook her. I felt her legs go weak and did my best to hold her up, all without giving up my delicious attack on her clitoris. I kept it going as long as I could, thoroughly enjoying as wave after wave of pleasure took her over. It wasn't easy holding onto her, especially as her pussy clamped down onto me, trying to coax my own orgasm out, but somehow, thankfully, I did.
As her orgasm waned and sanity returned to her eyes, she leaned over and kissed me hungrily.
"I've needed that," she practically growled.
"Glad to provide," I said, kissing her again.
Reaching down, she gingerly pulled my cock from her pussy. "You gave me one helluva cum, now it's my turn to return the favor..."
Unhesitatingly, Mrs. McNeil got down on her knees and practically inhaled my cock, burying its entire length in her throat in one bob before pulling back so she could suckle on the head like a lollipop. She looked up at me with loving eyes that were a sharp contrast to the lewdness with which she worshipped my cockhead with her tongue and lips. She rolled her tongue over it, sucking on it with loud, luxuriant pops of her lips before inhaling my cock again and again, sucking on me with a vigor that was truly amazing.
Taking my cock from her mouth again, she looked up at me smiling, speaking with an unbearably sweet voice punctuated by licks or sucks to my cockhead while her hands slowly jerked my shaft. "You helped me cum really hard, and I appreciate that, but you don't have to hold back anymore. I want you to cum for me. I want you to fill my mouth with your seed and then have you watch as I swallow all your sweet juice. Cum for me, drain your balls in my fucking mouth, Ryan."
"Yes, Mrs. McNeil," I groaned as she took my cock back into her mouth and truly went to town.
I put my hands in her hair, truly lost to the pleasure as she gave me one of the greatest blowjobs I'd ever had. I felt my orgasm building, faster and faster, almost ready to burst, the pleasure building, ready...
"Oh god, I'm cumming, I'm cumming, I'M CUMMING!" I warned, holding onto her head tightly as the dam broke. I fired shot after shot into her mouth and she did her best to swallow it all, but it was a flood the likes of which I'd only rarely accomplished. She tried to keep up with swallowing it, but eventually it was too much. She took her mouth from my cockhead and I watched as a few last, stray ropes blasted her lips, her chin and even her massive tits. The water that sprayed down around us washed a fair amount away, but it was still an impossibly lewd sight I wanted to have burned into my memory forever.
Once I stopped cumming, still glad to be on my feet, I looked down at her as she smiled at me sweetly, then opened her mouth to show the positive lake of cum she'd gathered inside. Then, with one final, resounding gulp, she swallowed it all down.
"Delicious," she said, smacking her lips.
If it were possible, I'd have taken her right then and there again, but with my cock drained and the heat of the shower starting to get to my head, I said, "That was amazing, but I think I need to step out and dry off now."
"Good idea," she said, getting back to her feet and kissing me on the lips. "Give me a couple minutes to do my hair, and I'll join you in the bedroom?"
I smiled. "Sounds great."
***
A couple minutes turned out to be closer to twenty, half in the shower and half listening to a hairdryer through the bathroom door, but since I was lounging on a comfy bed, regaining my strength and watching TV, I was pretty content. I'd just had some pretty amazing sex with Lauren McNeil, and barring any disasters, I was looking forward to some more with her soon.
(Spoiler Alert: there were no disasters.)
It was a couple moments after the hairdryer off before the bathroom door opened again. Mrs. McNeil stood in it, posing sexily. She ran her hands through her long hair and let it cascade down around her as if she were in a shampoo commercial, only one where the model was completely naked.
"That was... nice," she purred, sauntering over to me on the bed.
"Seriously. That was more than nice," I said, still in absolute awe of her body.
"I know, but I didn't want to set too lofty a set of expectations for what's coming next," she said, plopping down face-first on the bed beside me and laughing playfully. I didn't know what to admire more, the lovely smile that crossed her face, the way her immense breasts pillowed out underneath her, or the marvelous peak of her ass.
Instead of choosing just one thing, I decided I'd rather enjoy the whole picture.
"So..." she said. "...how've you been doing? We haven't talked much since..."
"Thanksgiving," I finished, not much caring for how the word sounded. As one of the more miserable days of my life, it was one I didn't want to think about any more than I had to, but Lauren was right; we hadn't talked much since then. We'd chatted a little in December after I began my mad Christmas effort to do something nice for every woman I'd had sex with and I'd gotten her husband to stop cheating on her, but not much since then.
Even though my cock had a mind of its own when it came to what I wanted to do next, the thought of catching up with someone I really liked had a way of holding it at bay for a time.
"Pretty good, actually. Really hectic with the holidays, but good. I've got a lot of friends now. Even got a girlfriend," I said.
Her eyes went wide for a moment, almost worried. "She's okay with this?"
I laughed. "Are you kidding? She loves this. She loves me coming back with stories and then fucking me like crazy afterward. I'm very discreet, and she knows how to keep a secret, but... yeah, things are good with us. Really good."
Looking relieved, Mrs. McNeil replied, "Oh, good. I know... I know things are a little weird on my side of all of this, but I wouldn't want any of what's going on with me to reflect badly on you."
"I'm cool," I said.
"Good," she replied.
"How about you? How've you been doing?" I asked.
She sighed, rocking her head back and forth. "Some good, some bad, but more good than bad. Since I like to get the bad out of the way first... Tori's still... she's still figuring herself out, after everything on Thanksgiving. That girlfriend of hers, April, has been really good at smoothing things over, but Tori and I have our good days and our bad."
"I'm sorry about that," I said.
"Well, it happened, and it probably needed to happen in one way or another. Tori needed to understand some of the harsh truths about her dad, and that she doesn't have sole claim over what you do with your life, and the sooner she understands them, the sooner she'll get her head on straight," Mrs. McNeil said.
I nodded. "Yeah. Yeah, that sounds like Tori."
"Yeah," she grumbled, clearly wishing things were easier. "In better news, Don's been really trying to make things up to me after you got his mistress to break things off with him. Rachel and I have really been talking, and though we've still got our issues, I think we've made some breakthroughs lately."
I had nothing but good feelings toward Lauren's older daughter, Rachel, so this greatly warmed my heart. "I'm really glad to hear that."
"I'm glad to be living it," Mrs. McNeil admitted. "And... believe it or not, I've actually been getting out more."
"Dating?" I asked.
She laughed. "No, nothing like that. I realized that I was spending too much time identifying myself as either a successful businesswoman or a dedicated mom, but with both of my girls 18 or older, I realized I needed to start taking care of myself and getting to meet people more. So I joined a 'book club'."
"I can't help but hear the air quotes when you say the phrase 'book club'. Spill it," I said, teasing her.
"Well, officially it's a book club, but it's mostly an excuse for a lot of us moms to get together, drink wine and dish on our sex lives. Or lack thereof," Mrs. McNeil said.
"Sounds like fun," I said.
"It has its moments," she said, with a sly smile. "Especially when Viola Kent brings out the case she uses for one of her side businesses and tries to sell us on her products."
"Oh? What does she sell? Makeup? Tupperware? Protein bars?" I asked.
Without even a hint of embarrassment, Mrs. McNeil said, "Sex toys."
"Oh," I said. That made sense for how smug Lauren was.
She reached over the edge of the bed, grabbing her white Hitachi magic wand vibrator.
"It's a lucrative business, especially when there's so many housewives out there, in our fair town and beyond, who need a little more than they're getting at home. I love Don, but I don't think he can make me cum as hard as this bad boy can," she said, beaming with pride.
Getting a bit of an idea, I said, "Show me."
"Show you?" she asked.
"Yeah. Cum for me. I'm always busy when I try to make you cum, I think I'd like to just watch it happen," I said.
Of all the things I could've said, this one seemed to take her off guard the most. She smiled, almost blushing, and said, "Okay."
Mrs. McNeil rolled over and scooted up the bed so she was sitting against the headboard, and I slid up to join her. Somewhat timidly, she turned the vibrator on and pressed its buzzing head against her clit.
"Mmmm, fuck..." she groaned, tensing up slightly as the powerful vibrator went to work on her.
"Looks nice," I said.
"Nice doesn't even begin to cover it," she said, her eyes rolling back before she closed them entirely.
"I know, but I didn't want to set too lofty a set of expectations for what's coming next," I said, repeating what she'd told me earlier.
She barked a short, harsh laugh, then turned the vibrator up an extra setting.
"Ohmygod, ohmygod, ohmygod fuck, fuck, fuck!" she said, bringing a hand up to cup one of her tits and squeeze her nipple. I was tempted to help her out, but I wanted to watch her do this to herself. I wanted to watch her cum, in part because I thought there was nothing quite as perfect as watching a woman cum, but also because this seemed to be getting an interesting reaction from her. I didn't think she was used to putting on a show, but despite some initial nerves, she was really getting into it.
Her eyes opened again, locking onto mine as she began rocking her hips against the powerful toy.
Giving her something to look at, I began jacking my already hard cock.
"Yes, like that, jack that cock for me, fuck, keep going like that, right there, fuck, fuck, fuck," she whined, rocking her hips faster and faster as she continued vibing herself. I wasn't entirely sure who she was talking to, but I had no intention of jacking off any more than I was. I had plans for my cum, and this wasn't the time.
With a sudden lurch, her body jerked explosively as she cried out in a high, formless sound of pure bliss. The orgasm took her almost by surprise, but she rode it out marvelously, getting every last jolt of pleasure that the vibrator had to offer her.
Mrs. McNeil looked at me expectantly, setting the vibrator aside.
I smiled at her devilishly. "You're not done with that yet, are you?"
With an equally wicked grin, she replied. "You're not jealous?"
"Not in the slightest. Keep cumming for me; I'll let you know when I'm ready."
Licking her lips and bringing the toy back to her pussy, she said, "Deal."
I watched her cum three more times after that with the vibrator pressed firmly to her clit, each one bringing out a more uninhibited, wild side to a woman I already knew to be fairly uninhibited and wild. The first time she came, she screamed so loud I would have sworn the neighbors would pound on the wall.
The second time she came, they actually did.
The third time might have been a show at the Bellagio fountain for how much she squirted on the bed, an act that took her almost by as much surprise as it did me, but one that finally broke my admittedly impressive restraint.
I couldn't watch anymore, not when she was looking so positively delicious. I dove between her thighs, pushed her toy to the side and placed my mouth on her sopping cunt, licking and sucking like my life depended on it. I always loved going down on the women I was with, because I loved giving pleasure as much as I loved receiving it, and for the act's unique ability to unlock the side of them they usually kept hidden from the world.
With your face buried between their thighs, your tongue going to work on their pussy, you can often see the person they wished to be that society would never let them be, and it was a side I always loved to bring out, if just for a little while.
That Mrs. McNeil happened to have a particularly delicious pussy was only icing on the otherwise very tasty cake.
"God yes! Fuck, fuck, fuck, fuck, fuck!" she exclaimed, digging her fingers into my hair as she frantically gyrated her hips against my face. "Oh fuck I've missed that tongue, missed those lips, keep going, keep going, like that, fuck yes, god you know what I need you motherfucker, right there, keep fucking going, like that!"
I wasn't quite as efficient as her vibrator, but I still knew what I was doing. Though it took a while longer than her toy, it wasn't all that long before my tongue (with a little help from my fingers to push things over the edge), had her cumming against my face.
With my mouth still on her moist, quivering lips, I looked up at her through the insane canyon of her cleavage. With tousled hair and half-lidded eyes, her face was one of pure lust, a lust that was only just rising.
Forcefully, she pushed me onto my back, climbing onto my hips and sinking my cock deep into her pussy.
"Your turn," she grunted, bouncing up and down on me energetically.
"If you insist," I said, planting my hands on her jiggling ass as she rode me and rode me hard.
"I do insist," she said, bending over just enough to hang her beautiful tits above my mouth. I took the hint and suckled on them. It was no easy task for how furiously she was riding me, but where there's a will, there's a way, and I definitely had the will.
Mrs. McNeil continued, "I insist because you've got a nice, thick, young cock and you know how to show a lady a good time. It's not every guy who'd make sure I got off before anything else, and I want to return the favor. So, I'm gonna fuck you, or you can fuck me, whatever works, but we're not gonna stop until you've filled my tight pussy with your cum, okay?"
I agreed with her, but with a mouth full of tit the only sound that came out was one I'd hesitate to even attempt to put into words here, so let's just agree that I agreed with her and get on with the sex?
I'm cool with that if you are.
While there's nothing in life quite like having a fit, redheaded MILF bouncing on your cock, I'd been rock hard and building to an orgasm for quite a while now. I needed to get off, and even though I knew she was more than capable of getting the job done, I was close to an animal by this point.
Wrapping my arms around her and pulling her in close, I rolled on top of Mrs. McNeil and started fucking her. Considering the squeals of pleasure this got from her, I figured this was the right move.
"GOD, YES!" she roared as I pistoned in and out of her like a machine. "FUCK ME, RYAN! FUCK ME SO FUCKING HARD YOU MOTHERFUCKER! FUCK ME, MAKE ME FUCKING SCREAM, FILL MY FUCKING PUSSY WITH CUM, FUCK, FUCK, LIKE THAT, LIKE THAT YOU MOTHERFUCKER, KEEP FUCKING ME, GODDAMN IT'S SO FUCKING GOOD!"
While I loved her dirty talk about as much as I loved anything else in this world, her mouth was so tempting that I couldn't keep away from it. I kissed her almost as hard as I fucked her, the taste of her pussy still fresh on my lips. Almost voraciously, she returned the kiss, licking and sucking her own taste from me.
My hips were a blur at this point, my cock almost taking a full stroke with each thrust. The pleasure of her pussy was overwhelming, but it was the whole package that was Lauren McNeil, her beauty, her kindness, her warmth and how insanely hot she was, that set my mind ablaze. It wasn't just one thing that set off my orgasm, but when it came, when I roared formlessly and fired what felt like a fire hose's worth of cum deep inside of her pussy, it felt like it was a long time coming.
I almost blacked out from the pleasure, but pulling back at the last moment, I climbed off of her once I was completely drained and lay down beside her. We stayed like that for a while, panting, sweaty and basking in the afterglow of some pretty quality sex.
After a silence, she said, still panting, "I should've reminded you, when I get horny, I get a little crazy."
"I remembered... from last time," I replied, panting.
"Good," she replied.
We were silent for a while longer, when a thought that had been bugging me for a while finally came out, "Not that I'm complaining about being naked with you, but what happened with my clothes?"
Mrs. McNeil laughed, "I sent them down to the hotel's laundry. They should have them back here in a bit."
"Cool," I replied.
"Why? Did you think I'd thrown your clothes out so you wouldn't be able to leave here and I'd be able to make you stay here with me forever?" she said with a raised eyebrow.
"Not exactly, but the thought hadn't slipped my mind," I said.
Smiling, she rolled over and kissed me. "Would if I could, but the room's only paid through until Sunday morning."
The full scope of what she was saying began to hit me. "So you've got this room for two nights, one day?"
She nodded, but when she spoke again her voice was almost timid. "I needed some time away from the world, and it felt like it might be enough. Why?"
This wasn't exactly something I'd planned out in advance, but the more the idea spread, the better it sounded. I proposed, "Well... I don't really have any plans this weekend; if you're looking for some company for more than tonight... I'd be game for that."
"Yeah?" she said, her eyes twinkling at me sweetly.
"Yeah," I replied.
"I mean... I'd hoped, but I didn't want to assume, and-"
I cut her off with another deep kiss. It would be a little while before I'd be able to do anything, but I wanted to make it a promise of what I meant to do from there.
Mrs. McNeil got my message. She was in a daze for a moment after we broke the kiss, but once she got her senses back, she smiled at me devilishly. "I just want you to know, that if you stay here, there's gonna be a lot of sex. And I mean... a LOT of sex."
"I figured," I said, smiling.
"I knew you might, but I want you to understand something, I intend to have all the sex with you. Every chance you're able, I want your cock in my mouth, my cunt, my hands, between my tits or buried deep in my ass. I want you to fill every hole I've got with as much cum as you've got. I want you to make me scream every bit as much as I want to push you to your limits, and I intend to push you as close to your limits as possible. I've told you before that I may go crazy on you, but if you agree to stay with me... you'll see crazy like you never knew possible," she said
I looked down at my cock, which had already regained some of its capabilities. Her eyes trailed and saw that as well, and encouraged, she gently wrapped her hand around me, slowly jerking me back to life.
"So... are you sure about this?" she asked.
Unhesitatingly, I replied, "Positive."
Nodding, Mrs. McNeil crawled down the bed and planted a single kiss on my cockhead.
"This is gonna be fun," she said, inhaling my entire length.
***
Now, I'd had some marathon sex sessions before, but spending half a weekend with Lauren McNeil might just have put any of the rest to shame. When we weren't eating takeout delivery or sleeping or regaining our energy while watching the hotel's laughably bad (but undeniably hilarious) pay-per-view porn channel, we were fucking, a lot. To go into exact detail would take a full novel's worth of words, but a few choice images come to mind.
Her feet on my shoulders as I pounded down into her ass for all she was worth.
Fucking her from behind, her tits pressed up against the glass window as we both overlooked the dark and rainy Blair Valley.
Waking up with her lips wrapped around my cock on the first day, only to return the favor by waking her up on Sunday with my mouth on her pussy.
Cumming all over her lubed up tits, watching as she tried to catch drops on her tongue and only wound up with a cum splattered face.
And then there was our finale, our last morning together, where we fucked for everything we were worth. By the end, I had what might have been the single lewdest picture added to the Senior Year Memories photo album on my phone, as right after I filled her ass with one more load of cum, Lauren rolled over and spread her legs wide, revealing her face and tits to be covered with, while her stretched out pussy and asshole leaked, my cum. It was a glorious, painfully erotic sight.
But, like many good things in life, it was one that couldn't last.
After we felt good enough to stand, we got showered off, got dressed, grabbed some food at the complimentary continental breakfast downstairs, and checked out. The hotel people seemed to be glad to be rid of us, but I don't think either of us minded for the marathon sex weekend we'd had.
We picked up my bicycle, packed it up in the back of Lauren's car, and then took the dark and rainy drive back to Regan Hills, and our real lives.
We hadn't talked a lot that morning, perhaps because the end of this encounter felt so bittersweet, but by the time we got close to my house it couldn't be avoided.
"I had a really good time with you," Lauren said.
"Me too," I said.
"I can't... it's all so complicated... I can't promise we'll be able to do this again, but I'd like to, sometime, if we can make it work," she said.
Putting my hand on her thigh comfortingly and knowing there was a good chance we'd never be able to do this again, I said, "Me too."
"You're really good at this," she said, smiling.
"I think you've got me beat," I replied.
"Well, I may have the looks, and the skill, but you've got the skill so..." she trailed off, jokingly.
Laughing, I poked her in the side.
Finally at my house, she pulled into the driveway. It was about as final as it could have been, but it was still a moment neither of us wanted to end. All we had to accompany us was the sound of the rain, which had become an impressive downpour by this point. As far as we were concerned, there might have been no real world beyond this car.
We looked at each other awkwardly for a moment, then broke down and began to make out. It was frantic and furious and the last ditch effort to not have to end this lost weekend of lust, but damn did it feel good.
"If you... finger me one more time... I'll give you the best blowjob you've ever had," Mrs. McNeil groaned.
Since that sounded like an excellent way to end things, I reached underneath her skirt and said, "Now who's the one with the silver tongue?"
***