Senior Year Memories Ch. 35

"Is Mrs. Harker really that bad? She seems decent enough to me," I said.

Sabrina eyed me briefly, smirking slightly at a silent secret that she rather enjoyed. "Yes... I gather that would be your assessment."

I freaked out for a moment, wondering if she was going to spread any information on what Mrs. Harker and I had done, but it only stayed at the silent smirk.

Sighing, she nodded, then began to walk away from us, "Nevertheless, it's never too late to start planning for your future! My offer still remains!"

I watched her walk away appreciatively for one moment, before I felt a playful elbow in my side. Jennifer said, "Certainly seems like she could use some relaxation in her life."

"She might..." I said, considering, "But not today. I've got plans for this afternoon."

"Yes, but you never know where life might take you, right? Couldn't she just use a little..." Jennifer joked, thrusting her hips forward and making a joking grunting sound.

I rolled my eyes, laughing as I continued down the hall. Jennifer kept up with me.

"What? I was just having fun," she chided.

"I think I created a monster," I said.

"A good kind of monster?" Jennifer asked.

Taking my chance to elbow her back, I said, "The best."

"Hell yeah," Jennifer replied, pulling me in so she could kiss me on the cheek. "Still, doesn't help me fill up my afternoon."

I thought about this. "Alright, apprentice, let's try a homework assignment, then."

"Really?" she asked, intrigued. "What do you have in mind?"

Looking up and down the hall, I said, "I want you to find someone... someone you find really hot... and try to make a connection. You don't have to seal the deal or anything, but put yourself out there, give it a try..."

Jennifer looked a bit nervous at the suggestion, but she took a deep gulp and said, "Okay... okay. Okay."

She didn't sound very okay about this, and while getting laid was one thing, it didn't exactly help someone with all the social elements that came with a sex life at this school. I was working on a speech where I could detail this for her, but before I could, we were interrupted.

"Hey, Ryan!" a man called to me.

From down the hall in front of us came a couple I'd become pretty familiar with over the past couple months: Peter Nixon and Sasha Pearl. Peter was a football player and ladies' man, big and black and charming as all hell, while Sasha was a nerdy and glasses-wearing, but damn cute, redheaded cheerleader. I'd been tutoring Peter recently, while Sasha and I had had some... well, creative fun over New Year's at Dakota Lewis' house. Thankfully, Peter was not one to hold grudges on such things, as the two of us had become fast friends over the past weeks.

"Hey, guys," I said, waving for them as they approached. Jennifer couldn't take her eyes off of Peter, and she might have even licked her lips.

Interesting.

"Hi!" Sasha exclaimed, looking from me to Sasha. "You're Jennifer, right?"

"Yeah," Jennifer said, a little shyly at the taller cheerleader.

"You and Ryan are friends?" Sasha asked, curiously.

When it seemed like Jennifer wasn't ready to answer, I spoke up, "Yeah. I've been... tutoring, Jennifer lately."

Peter knew well that I had my hands full tutoring him, Kaitlyn and Jess, so he only gave Jennifer one good, long look before flashing me his charming smile. "That's awesome. Ryan's a helluva 'tutor', isn't he?"

Jennifer blushed slightly. "Oh, he's been great."

Sasha looked around the group, amused. "So, we're talking in code now? Can I talk in code too? Or would that make you uncomfortable?"

She addressed this question quite genuinely at Jennifer, who answered only by blushing a whole lot more.

"Oh no!" Sasha said, patting Jennifer on the arm comfortingly, "I didn't mean to do that! It was a joke, I swear, a goodhearted and thoroughly unloaded one! I'm so sorry!"

"I'm still working on my joke threshold," Jennifer said back, looking from Sasha to Peter. "And no need to feel sorry, I'm still learning."

"Give it time, you'll catch up quick around here," Peter said smoothly.

"Yeah?" Jennifer asked. At that, Peter grinned, and this time a smile joined her blush.

I could sense an opportunity here, one that I wanted to tee up to see if Jennifer would take it. "Say, Peter, Sasha... you two doing anything after school today?"

"We were gonna grab a bite to eat, then hang out for a while," Sasha asked. "Why?"

I looked at Jennifer, who had a faintly panicked look in her eyes, but one I wanted to help her past. "Well, I've been keeping Jennifer company the past few days with our tutoring sessions, but something came up for me today and I won't be around to help her out like I usually would. Any chance the two of you would be up for hanging out with her?"

This wasn't meant to be a specifically sexual invitation, more just a chance to get Jennifer comfortable around other people I knew she was attracted to. I could already see the sparkles in her eyes for Peter, and knew that Sasha could be a lot of fun for her too, and she needed an opportunity to see how she could develop this when I wasn't around.

Now it was just a matter of seeing if they'd want to help.

"I'm down if Sasha is," Peter said with his most charming smile. "Any friend of Ryan's is a friend of ours."

Sasha smiled brightly. "Sure! The more the merrier!"

Jennifer looked at them and me nervously, biting her lip again and looking like she wanted to hide. If she chose this moment to run off, I wouldn't have blamed her. This might have been a bit much for her to process right away, but I thought there was a good chance she could handle it...

Balling her hands into fists and then releasing them, Jennifer said, "I'd love to hang out with you guys. Thank you."

"Cool," Peter said.

"We'll meet you in the parking lot after school lets out," Sasha said, looking at me and raising an eyebrow with an idea of her own. "Or, do you want to join us for lunch so we can hash out details then?"

Jennifer looked at me. "You want to join them for lunch?"

"Go ahead," I said. "I have to drop something off at a locker, and I should probably be checking in at the Puma Press offices soon, been a bit overdue for that and I don't want Nadia to kill me. You have fun."

Smiling, Jennifer nodded and walked off with Peter and Sasha. "I think I will... thanks!"

I grinned at her, proud to see her so readily stepping out on her own. I didn't know if she'd get into any mischief with Peter and Sasha, but I hoped she would. Peter and Sasha were good people, and I knew they would be good for fun if Jennifer was looking for it.

I nodded to myself, walking down the twisting hallways of Regan Hills High with a spring in my step as I searched purposefully for a specific locker. Thanks to information I had gotten from Brooke, it didn't take long to find Brianna Roth's locker, and to slip inside the Valentine that I had secreted away in my backpack. Sure, I could have texted her to get my point across, but since she had taken the time out of her day recently to drop a Valentine by me, I was more than happy to return the thought.

It wasn't every day you invited a girl to dinner on Valentine's Day, after all.

I know what you're thinking, and I'm going to answer it now: why was I not doing dinner with my girlfriends, Brooke and Josie, for Valentine's Day?

Simply put, Josie and Brooke were the people I was going to end Valentine's Day with. I had told them about my plans for the month, and some of my ideas for the day itself, and they encouraged me to spread the love (or at least, lust) around, so long as I ended things with them. They had gotten a room at a nearby motel for their "big surprise" they'd both set up, and I knew I was supposed to show up there by 8 pm so we could enjoy whatever debauchery they had arranged. Until then, I could get up to whatever trouble I wanted.

Brianna Roth had been a girl I'd been meaning to do something with for a very long time. One of Kaitlyn's friends, Brianna was one of the first to know of my "gift" outside of Kaitlyn. She'd hit on me during those early days of September, dropping a pen and asking me to it up, giving me a sweet view up her skirt as she sat at her desk. Luck and timing had prevented us from ever fully hooking up, and while I had gone down on her in a disused art classroom, I wanted to do more.

And so, knowing that she was currently single, I wanted to take her out on Valentine's for dinner and... hopefully, quite a bit more.

Smiling, satisfied with my plan, I made sure that I'd slipped the card thoroughly into her locker before walking away.

"That isn't your locker..."

I grinned at the sound of her voice. "No, it isn't. That a problem?"

I turned to face Kaitlyn Pruitt, smiling as if I hadn't seen her in ages. She looked good. Really good. Her skin was still as soft and lightly tanned as ever, her silky, mid-back length black hair shining even under the shitty light of our school hallways. Today she wore a light, open jacket that exposed the tight, midriff-baring green t-shirt that barely concealed her massive tits, while her jeans were as tight as ever, accentuating her round ass and cheerleader's legs. Her pouty lips were curled in a playful grin, though still had a hint of her usual resting bitch face, while her eyes... big and brown, they looked at me with the best kind of "up to trouble" look I'd come to love from her.

"I guess it depends on what you're doing. Was that a Valentine?" Kaitlyn asked.

"It is," I said.

She continued, smirking cockily, "And does that mean that you and Brianna are finally gonna fuck? Because she's been wanting some of that cock since I first told her about you, and you've-"

"Been busy," I shot back. "And I don't know what is going to happen, but if sex is on the table... well, I won't say no."

Kaitlyn nodded. "Good."

"Good," I replied, walking down the hallway. I didn't want to leave Kaitlyn, but I did want to show her that I was willing to control the course of our interaction. She was surprised for a moment, but quickly caught up with me.

"So, Brooke tells me that you'll be spending Valentine's Day going to the dateless and bringing some 'joy' into their lives?" Kaitlyn asked.

I nodded. "And?"

"And..." Kaitlyn said, trailing off, before bringing the conversation around to what she clearly wanted. "...and I don't have a date, and could use a little of that joy, too."

She said this with her usual arrogance that she put on in public, but then leaned in and dropped to a softer, more genuine tone, "If you've got the time, that is."

I smiled. This was more the Kaitlyn I'd come to know over this year, the one who could get past her bitchy mean girl shit and be the friend she was capable of being before all the shit started.

"Walk with me?" I suggested.

"Of course," Kaitlyn said as I led her to a much less active hallway.

"So, how is it you, Miss Hot Shit Gorgeous Fucking Cheerleader, doesn't have a date for Valentine's Day? Pretty much every guy in our class would give up his left arm to be with you," I said.

She rolled her eyes at me. "I know it's that easy, but I don't want it to be that easy. Guys... in general, they're not interested in me, they're just interested in... this."

Kaitlyn waved down at her body, and I couldn't say that I didn't understand the issue.

"I'm looking for something different, even if it means I need to... cut back on certain exciting, sweaty, activities," she continued.

"I can see where that would be a problem," I said, peering around a corner and motioning for her to follow me once I saw the coast was clear.

"But that doesn't mean I don't still get horny as fuck, and there's only so many things the other girls can do for me. Sometimes a girl just needs a whole lot of dick, and that's where I'd like you to come in," she said, bluntly.

"I'm glad you think so much of me," I said, sarcastic and rolling my eyes.

Kaitlyn grabbed me, stopping me and pulling me in close to kiss me passionately. Never in a million years would she have done this in an open school hallway before, and even though the one we were now in was almost completely deserted, it still felt like a big deal from her.

"Ryan... you don't know everything you've done for me... you've helped me understand more about myself than I thought possible, and made me look at who I want to be in a different way. I think the fucking world of you, and I..."

She couldn't finish the last thought, instead biting her lip and looking up and down the hall. "You mean a lot to me, alright?"

I nodded. "I'm sorry. It was a bad joke."

"Yes, it was," Kaitlyn said. "But Lord knows I've made worse."

Kaitlyn pressed herself against me, leaning into my ear as her breasts crushed against my chest. She whispered so softly, so sweetly, that between that and her touch I couldn't help but be rock hard instantly.

"I want you, Ryan..." she whispered, her voice low and husky. "I fucking need you. I need your cock... I need your cum... I need how you make me feel..."

Realistically speaking, I knew how hard Kaitlyn fucked, and I should have passed. I still had a busy afternoon ahead of me once I got over to the Kent's house, and I probably should've saved my cock so I could stay in fighting shape.

On the other hand... Kaitlyn Pruitt really, *really* wanted to fuck me.

I cocked my head to the door on the opposite side of the hall of us, the closet next to Mrs. Lynn's classroom.

"Lucky for you, I know a place," I said.

Kaitlyn grinned, grabbing me by the hand and pulling me toward the closet.

The door to Mrs. Lynn's class opened, and out stepped Mrs. Lynn, carrying a couple of folders in one hand. She looked at us, both confused and intrigued.

"Hello, Mrs. Lynn," I said.

"Hi, Mrs. Lynn!" Kaitlyn said, looking like she was desperately trying to appear casual.

It didn't take more than one look at us for Mrs. Lynn to roll her eyes and say, "Just keep it down in there so you don't have Officer Brandy coming down on your asses, okay?"

Giggling, Kaitlyn and I looked at one another playfully, and she pulled me toward the closet.

***

It might go without saying that Kaitlyn and I, well, we couldn't exactly keep it down.

"GOD, YES! FUCK ME WITH YOUR BIG COCK! FUCK MY SLUTTY CUNT WITH YOUR COCK, HARDER! FUCKING HELL!" Kaitlyn roared as I did, well, precisely as she requested. Both of our pants and underwear were around our ankles, while Kaitlyn was bent over, hands against the wall as I fucked her from behind. With her shirt pulled up to her neck, her tits bounced wildly as I forced all ten inches of my thick cock roughly into her tight, clutching cunt. To this day, I can't say what exercises those cheerleaders did to keep their pussies so tight with how I fucked them, but Kaitlyn was remarkably adept at squeezing me with seemingly impossible force. Her pussy gripped me with every stroke, seemingly not wanting to let me go while I savagely pounded her.

With my hands on her hips, I got a great view of her jiggling ass, and even better control over this fuck... but that couldn't stop me from reaching up every so often to grab her magnificent DDs, pinching her nipples and squeezing her soft, bouncing flesh as I fucked her.

"Yeah, you like that?" I grunted.

"I fucking love it!" Kaitlyn squealed, looking back at me cockily.

Grinning, I reached down and smacked one of her magnificent ass cheeks, pulling an even louder squeal from her.

"God, you can be such an asshole when you're this cocky," she groaned, fucking back against me for all she was worth.

"And you like it that way, don't you?" I asked.

To this, Kaitlyn said nothing, but I took her moan as a good answer.

I thought another spank or two might motivate her to answer, and so I gave her a good slap to each of her magnificent, jiggling ass cheeks to encourage her to speak up.

"Don't you?" I repeated.

Kaitlyn looked back at me, practically snarling, "Fuck... you..."

I grinned, grabbing her hips and fucking her harder. "Actually, I'm fucking you."

She smirked back at me shortly before her eyes rolled back and her mouth dropped open in a deep moan. I knew Kaitlyn liked it hard, and rough, and I gave her the exact treatment she would cherish. She was skilled at using her body for giving and taking pleasure in the roughest, messiest ways, and I meant to be a good partner in that regard.

As her eyes fell back into place and she looked back at me with a silent understanding, I could feel that undeniable connection the to of us had. I had had sex with a lot of women this year, forged deep bonds of love and friendship, but what Kaitlyn and I had was its own unique thing. I could not tell you then where this would take us, whether we would be the best of friends or maybe even something more in time, but as I fucked her pussy deep and hard, and the two of us stared practically into each other's souls... I could feel the pleasure growing within me. Physical pleasure, to be sure, but something deeper, something that touched my very being as we reached the end of this carnal bonding between the two of us.

"Fuck me, fuck me, fuck me, fuck me..." Kaitlyn groaned, looking deeply into my eyes, her body shuddering with impending orgasm.

I leaned over, reaching around to squeeze her tits with both hands while I whispered in her ear.

"Cum for me... cum for me... *slut*," I hissed, putting extra emphasis on that last word in a way I knew would set her off.

It worked. Kaitlyn bucked against me, moaning loudly as the orgasm tore through her. I held her closely, still fucking into her as she cried out and her juices gushed down my cock, but soon I couldn't hold back either. Grunting loudly, I buried my cock deep within her pussy, unleashing a seemingly unending torrent of cum into her clutching, milking cunt.

I held her closely, leaning over and kissing her as we rode out our orgasms. As was often the case with Kaitlyn, the savagery of what we could do together when fucking was tempered by a softer, slower aftermath, the two of us making out gently while I softly massaged her tits. It felt good to be pressed against her, my sensitive cock still buried in her pussy as we held close to each other. It wasn't quite the same as it was with either of my girlfriends, but it was close enough that I didn't want it to end soon.

That lunch was ending soon, however, meant we didn't have much of a choice.

Kaitlyn pushed off of me, then fell to her wobbly knees, twisting around and giggling as she took my softening cock into her mouth. She suckled gently, briefly throating me before focusing back on the tip, making sure she got every last drop.

"That was... wow... I needed that," Kaitlyn said, giggling and standing back up on wobbly legs. She tried pulling her thong over her cum-soaked pussy, but if she meant to contain any of our juices, she was failing miserably. If that bothered her, though, she didn't let on.

"Thank you," I agreed. "That was pretty awesome."

Looking down at herself, Kaitlyn laughed, "You really shot me full of a lot of cum, you know? We keep going like that, one of these days you're gonna get me pregnant."

I laughed. "Yeah... that would be pretty crazy, wouldn't it?"

Pulling her clothes on gingerly, still shaky from our hard fuck, she shrugged and softly smiled. "I don't know... if I ever wanted to get knocked up... you know, a girl could do worse than you."

This took me for a moment of pause, and, I'll admit, perhaps a brief flaring of fear. It wasn't true terror, but a flash of the unknown and unexpected.

Kaitlyn saw this and placed a placating hand on my shoulder. "Relax, I'm not ready for that, not yet, I was just thinking. It's something I think about sometimes, the future, ya know? It's coming for all of us soon, and I guess I find myself seeing all the ways it could be."