Senior Year Memories Ch. 36

(Usual Disclaimer Time: Even though this story almost entirely takes place in a high school setting, all the characters in this story are 18 years old or older, and since we're living in the wide wonderful world of porno-land here, where clichés roam free and things might get a little unrealistic from time to time, please remember it's all in good fun. This story is highly serialized, and though it's not 100% necessary to have read the whole story up until this point to enjoy the content of the chapter, it's definitely advisable to understand the ongoing plots.)

(Author's Note: First and foremost, I'd like to apologize for some of the more direct similarities between the striptease/lap dance scenes between Chapters 27 and 35, including lines I accidentally stole from myself when writing Chapter 35. Whoops, this is what happens when you write two chapters more than a year apart and have some similar interests come through in both. Anyway, as always, I want to give special thanks to fellow Literotica author Lil_kitty for her excellent work as my editor and acting as a second set of eyes on this chapter, and for letting me know what did and didn't work; if you get a chance, please check out her work and drop some stars if you enjoyed, she writes some very hot and fun stories. And of course, I also want to thank my wonderful patrons; your support and input really help make this possible, as did your votes ensuring the appearances of Rose, Fatima and Izzy in this chapter.

And, as ever, apologies for my limited Spanish, and any errors that may have come into play thanks to Google Translate.)

Previously, on Senior Year Memories: In the month of lust and love, 18-year-old Ryan Collins keeps himself busy, helping his new "apprentice" Jennifer Cage make new friends by introducing her to football player Peter Nixon and cheerleader Sasha Pearl, while sneaking a Valentine's invitation to busty beauty Brianna Roth. After a quick encounter with Kaitlyn Pruitt, Ryan makes good on a promise to his friend, Sarah, to seduce her mother, Viola Kent. Viola is stunningly gorgeous, and an ex-stripper, and after working his magic with the beautiful MILF, the two of them have some properly wild sex. Exhausted after such a serious fuck, Ryan returns home to girlfriend Brooke King, who helps him relax while he mentally prepares for one of his greatest challenges of the year: Valentine's Day.

***

Until senior year, Valentine's Day had to be one of my least favorite days on the calendar. When you've never had a date in your life, let alone a partner, the perception that everyone else is dating *but* you can be challenging to handle. Valentine's Day only magnified that, to every possible extreme. It seemed like everyone else had people they loved, places to be, and there I was, sitting alone at home and munching on whatever mandatory candy was given out at school to every student so nobody would feel left out. It was one of those things the part of me that was convinced I was intellectual found insulting, but, hey, free candy was free candy.

The one good thing I had on those previous days was my oldest and best friend in the world, Tori McNeil. The two of us would enjoy our sarcastic bitterness together on Valentine's, eating takeout, watching action movie DVDs and sneaking some liquor from her big sister, Rachel's, private stash. Those days when it was just us against the world, well, they made Valentine's feel a little less lonely, and even if things didn't work out the way I wanted to between the two of us, I still looked back on those days fondly.

There were times these days when I found myself wishing that things had gone differently, that I hadn't had sex with Tori and her mom, Lauren, *and* her sister, Rachel. Things might have been different, a little more like they used to be with my oldest friend still in my life. Maybe even, in all of this, that I could still be watching cheesy action movies with Tori on Valentine's Day...

I still found myself wishing this sometimes... but every day I found myself wishing with less strength. Rachel McNeil had become one of my best friends, and even though we lived states apart, I still considered her one of my closest confidantes and my go-to person for advice in all matters of life, love and beyond. I wouldn't trade the friendship we'd developed since November for anything.

And Lauren... well, she was just a lot of fun on those rare occasions she and I would see each other.

No, for everything that had happened, there was no going back now, and I was generally happier for it. Things with Tori may have been in a strange limbo right now, but without question, everything else in my life was immeasurably better. I had more friends than I'd ever had in my life, was having crazy amounts of sex all the fucking time, and had two girlfriends who I loved more than anything else in the world.

Life was good.

Life was *great*.

And I was going to kick this Valentine's Day's ass.

You see, ever since I helped Leah Sartori cast her lust spell, a February I'd had few plans for had come into a clear, and very horny, focus. I knew what I had to do to spread around a little bit of love and a whole lot of lust to those who could use it, and the most ambitious day of my plan was handily Valentine's Day.

It was going to be hard, and it would require a lot of strength of both will and body... but I knew I could do it.

I woke up drowsily and slowly on Valentine's Day, but managed to turn off my alarm before it went off. As I cleared my eyes, I looked around my room with excitement and anticipation. I had everything in order, the bundles of flowers, the boxes of chocolates...

"Good morning, Ryan," the girl said from beside me in bed.

I turned, smiling, to look at curvy brunette Jennifer Cage, keeping herself thoroughly wrapped up in my blanket and looking very comfortable as she reached beside the bed and pulled on her glasses. The sweet, pale girl wasn't wearing much more than her glasses and a pair of panties, but, tempting as it would have been to climb on top of her and get a nice fuck in to start the day, I knew better.

I had to know better today.

"And good morning to you, Jennifer," I said, leaning down to kiss her before I got out of bed and started getting dressed. Pulling on my glasses from the nearby bedside table was an excellent first start, allowing me to get a better look at the beautiful woman in my bed.

Bundling herself up comfortably in the blankets, the better to deal with the surprisingly cool day, she said, "You're up awfully early for a Saturday, aren't you?"

"I got a busy day planned..." I said, pulling on my jeans.

"Ah, that's right... Valentine's Day," Jennifer said, amused.

"That a problem?" I asked, smiling down at her.

"Not in the slightest, I just forgot myself for a moment," she said.

"It's all good," I said, sitting back down on the bed to pull on my socks and debate just what I had to do in what order. "I'm sorry I have to leave in such a hurry."

"It's alright, I've got plans of my own today, anyway," Jennifer said, smiling mischievously.

"Oh?" I asked, definitely needing to hear this.

"Yeah. I'm trying to put myself out there more, like you're encouraging, and I was thinking I might just head to the mall. Maybe catch a movie, maybe see what kind of trouble I can find. Sasha told me she knew of some hot guys heading there tonight that she might be able to introduce me to, so... there's hope, if I play my cards right," Jennifer said.

"You'll play your cards right," I said, confident.

"I know. It's still a little nerve-wracking, but it's going to happen," Jennifer said, smiling.

"Good. I want to hear all about it," I said.

"You will... I'm just going to enjoy my nest of blankets here for a little while longer, anyway," Jennifer said. Luxuriantly, she closed her eyes for a moment, before quickly opening them. "That won't be a problem with your father, will it?"

I laughed. "Nah, he's out today; the roller derby team he co-owns is in a pretty violent dispute with their longstanding blood rivals again, and he's the only one both teams trust to resolve it, so, he'll be gone for a while."

"Again?" Jennifer repeated.

"Oh, yeah," I answered. "Things like this happen all the time."

"Interesting..." she said, stretching out. "Don't worry, I'll be out before you have to worry about date night with your girlfriends."

"Actually, I'm meeting Brooke and Josie at the Stargazer Motel on the other side of town; they got a room for their big surprise," I clarified, quickly finding my wallet in my jeans and opening it up to check that the room key they'd provided was still there.

"Right," Jennifer said, shaking her head. "But you're having dinner here first, with...?"

"Brianna Roth," I said. Kaitlyn's beautiful friend had thankfully accepted my Valentine's invitation, and considering how long our flirtation had gone over the course of these past months, it was about time the two of us finally did something about that. Well, something more than me eating her pussy in an abandoned classroom, anyway.

"Nice," Jennifer admitted, nodding. "And this is after you go running around like a pornographic Santa Claus handing out orgasms to some lucky girls who really need them?"

I shuddered. "While I'd rather purge the image of a pornographic Santa Claus from my mind... yes, that is the general point."

"Sounds like you're going to need a lot of cum in the tank," Jennifer said.

Ah, that was going to be the challenge, wasn't it?

"Not exactly," I said, finding it almost as uncomfortable to discuss the plan as it was to think about.

"What's that mean?" she asked.

I explained, "I need to be prepared for everything that's planned tonight, which should be pretty fucking intense with the cast of characters involved, so... I'm actually not going to be cumming until the main event. For today, I'm just using my mouth and hands, and keeping anything and everything I have to away from my below the belt areas."

"Ouch," Jennifer replied. "I mean, for them, that's awesome because, well, it's your mouth and hands, but for you, that'll be rough. And you're going to be riding your bike around the whole time?"

"More or less. I'm going to try to catch some rides when I can, but, yeah, that's still a lot of time on the bike," I replied, not wanting to think about how that was going to treat a very full, very ready pair of balls.

"Ouch," she repeated. "I was going to show you my tits to, you know, motivate you on the way out, but I think the less time you're hard, the better, so, I don't think I'm going to do that."

Feeling the erection already growing in my pants, I said, "Too late."

"Oh. In that case," Jennifer said, briefly pulling back the blanket and flashing me her soft, luscious, DDD-cup tits. The flash was brief, enough to let me see her soft curves and suckable nipples, before she pulled the blanket back over her chest and smiled mischievously.

Walking toward my desk to grab the first flower and small box of chocolates, I jokingly said, "Tease."

"I'm learning," Jennifer said.

"I noticed," I replied, climbing over her to give her a quick kiss. "Happy Valentine's Day, Jennifer."

"Happy Valentine's Day, Ryan," she responded, smiling brightly. "You know, I never thought I'd be in a place where I could say that and mean it, but... I'm happy it's Valentine's Day."

Knowing exactly where she was coming from, it made me swell with pride to be able to bring this out of her as well.

"Good," I replied, standing up. "I'm happy to hear it."

I made my way for the door. "I'm gonna go be your porno Valentine's Santa now."

"Good luck!" Jennifer called after me.

Smiling and shaking my head, I quietly thanked Jennifer for the luck.

It seemed like I was going to need at least a little of it if I was going to survive the day.

***

Now, while a lot of today's itinerary had me running around the town of Regan Hills like a madman, that the first stop was close by made my life quite easy, even if I had to get there pretty early if I wanted to catch her before she went on her run.

With a flower in one hand and a small box of chocolates in the other, I exited the house with plans to walk next door. This was interrupted, however briefly, by the discovery of a tray of cookies with a small note attached to it, another attempt at a peace offering from Karen Bowman, mother of my former bully who was no doubt working some angle. I pushed the cookie tray indoors, and focused on ignoring it.

Nothing was going to get in my way today.

Steeling myself for the day ahead, I walked over to the house next door, up to the front porch, and rang the doorbell. I hoped I hadn't missed her, but knew that was a fair possibility. Maybe she'd already gone on her run, or maybe she'd gone out with her mom; the car was absent after all. Or maybe-

The door unlocked, and before me stood the beautiful Alice Talbot.

"Ryan!" she exclaimed in her lightly Australian-accented voice. "What are you doing here so early?"

The athletic beauty stood in a matching dark blue tank top and yoga pants, showing off much of her toned body, tight curves and dark skin. Her hair, beautiful dark curls she usually let free in an impressively loose afro, were tied back for running. While her face was as pretty as it ever was, when she saw me, she positively lit up with a look that made her even more beautiful, if that was possible.

"Happy Valentine's Day!" I said, handing her the flower and chocolates. "Can I come in?"

"Certainly!" she said, ushering me inside. "Mum's off at work today... but shouldn't you be with Josie and Brooke?"

"By most romcom plans, I should, but things are going to be a bit unconventional today. We do have plans to meet up later, but I've got other ideas, first," I explained.

"Really?" Alice asked, arching an eyebrow.

"Yeah," I said. "I can't stay long, but I did want to drop off the flower and the chocolate-"

"Which you did," she interrupted.

Without breaking stride, I continued, "-and see if you, I dunno, would like it if I ate your pussy? Or fingered you? Or both? Whatever it takes to give you a mind-blowing orgasm or two? Something a little more special than your usual Valentine's chocolates and flowers?"

Alice looked at me at first, disbelieving, before laughing. I stood my ground, and when she saw I was serious, I could see her chest rising and falling with anticipatory breaths.

"Oh, that wasn't a joke," she said, lightly licking her lips.

"No," I answered. "You told me that you didn't have any date for Valentine's, and if I didn't have any other plans, I would be here for you fucking you with all I had all day. Unfortunately, I need to do a lot of running around today, but if you'd like a couple of mind-blowing orgasms before I do, I am offering."

Alice looked at me with only the briefest consideration and said, "I think you know the answer to that."

***

"YES! YES! FUCK YES!" Alice moaned, leaning back into her bed as she ran her hands through my hair. With her top pulled up over her beautiful, bare C-cup tits and her pants and underwear a long-forgotten issue, I feasted on Alice Talbot's beautiful, shaved pussy as if it were my last meal.

"Yes, god, yes, fuck... right there, right there, you know what to do... you know how to treat a girl right..." she moaned, her eyes rolling back as the pleasure flowed through her.

I could have made a choice response or two to this, but with a mouth full of pussy, I would have to keep my quips to a minimum. With two fingers buried deep in her cunt, massaging her g-spot, my lips and tongue were primed to tease her lips, running over them oh so lightly before running more firmly over her clit. I had been with Alice a handful of times already and found her to be very responsive, but even if I knew how to make her cum quickly, I was going to draw this out.

It was Valentine's Day, after all... I had to make it memorable, right?

So, I teased her. I pleased her. I brought her to the edge, and then took her back, and then pushed her close to the edge once more. I made her a needy, whining, sex-driven beast, rocking her hips against my face and forcing my head between her legs with her hands, but I still kept rocking her back and forth.

For her part, Alice seemed to be having a pretty good time.

"Bloody hell... fuck me... fuck me with your mouth, Ryan, like that, please, make me cum, make me cum... god... fuck..." Alice groaned, squeezing her thighs tightly around my head. "You're gonna make me cum, do it, please, please make me cum..."

Her body had fallen into a state of tense, shaky, pleasurable readiness, and I didn't think backing off any more would have the desired effect. And so, I didn't back off next time. I massaged her G-spot more intensely, my tongue circling vigorously over her clit.

At this point, yeah, it didn't take too much for her to cum.

"HOLY FUUUUUUUUUUUCK!!!" Alice cried out, her thighs clamping down around my face as her juices flooded my mouth. I kept suckling away at her pussy, prolonging her orgasm for a few moments more, before easing up to let her come down.

Once she let go of my face, I propped myself up on my elbows to get a better look at her, and of course to give her a better look at me licking my lips.

"Why are you looking so smug there?" Alice teased.

"I think you know why," I replied.

"Oh, right, that," she laughed.

I crawled over her, leaning down to give her a long, lingering kiss, enjoying how eagerly she licked her juices from my face.

Feeling my erection against the side of her leg, Alice asked, "Would you like me to return the favor?"

I grinned, kissing her again. "Would I like to? Yes. Can I? Not today."

"Poor baby," she replied, a little teasing. "Needing to save up for later."

Playing back, I squeezed one of her nipples, hard. Alice winced, but then grinned back.

"Do you want another cum, or don't you?" I asked.

"I do," she replied.

"Then I'd play nice, if I were you," I said back, playful yet commanding.

Alice licked her lips. "Oh, I like this side..."

Climbing back down between her legs, I said, "I think you'll like this even more..."

Though she looked like she had something to say about this, Alice's words soon caught in her throat as I licked her clit again, and set about giving her an even better orgasm than the first.

Since I later succeeded in that, I considered this first stop to be a success. I only hoped the rest would work out so well...

***

"Mmm, yes... Ryan Collins, your tongue has true talent... yes, this would make for a happy Valentine's Day..." Rose Ferris purred. We were in her bedroom, an eclectic chamber of books, art supplies and mismatched used furniture that gave it a particularly bohemian style. I could have spent some true time studying all of her assorted treasures and rare books on nearly any other day, but when I was knelt behind her with my tongue buried in her ass and three fingers fucking in and out of her pussy, a more in-depth analysis would have to wait for another time.

The 5'8", lightly tanned hipster stood over me, her hands braced against the wall with her legs spread wide as I buried my face between her ass cheeks. Rose was, quite gloriously, naked, and while I couldn't fully appreciate her beautiful C-cups and shaved pussy, I was quite fine right where I was. A former cheerleader, Rose Ferris' ass was a true work of art, and I was in a prime position to appreciate it. I lavished her asshole with my tongue, running tight circles over it and pressing inside whenever I wanted to drive her truly wild. Though she was quite good at keeping up mellow appearances, I could tell she really enjoyed the impromptu DP I was giving her.

"Like that, right there," Rose said, turning just enough to look down at me. As ever, she still kept on her fedora and slightly oversized and never too dark sunglasses, looking down at me with that easy, relaxed smile that could make my heart beat faster with minimal effort.