Senior Year Memories Ch. 33

(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: So, it's been a while for a long-needed break and hiatus, but Senior Year Memories is back! After some soul-searching and review, I am working on this story once again, looking to make it leaner and more direct than it had gotten in the last handful of chapters, and back to something that's much more manageable on a regular basis. We'll see how well I hold to that, but, thank you for your patience, and I'm looking forward to sharing some of the adventures to come! 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.)

Previously, on Senior Year Memories: At the beginning of January, 18-year-old Ryan Collins made a promise to the skater he was tutoring, Jess Garza, that if she improved her grades by the end of the month, he'd have sex with her. After she made good on her end of the bargain, she took Ryan to her van to fuck, only for them to be interrupted by the school safety officer. Running off in the middle of the day, they took shelter at the apartment of Jess' weed dealer, Lana Granger, to get high and have some inventive three-way sex to celebrate. Getting home, Ryan discovered two surprises. The first, was a tray of cookies left behind by the mother of his archnemesis, Kyle Bowman. The second, was cute, meek and nerdy art student, Jennifer Cage, asking to become Ryan's sexual apprentice.

***

It was the last night of January, and there I was, sitting in the kitchen of my home at a table opposite Jennifer Cage, still completely fucked into exhaustion and reasonably stoned as we ate cookies and milk. That the cookies had been provided by the mother of my longtime bully, Kyle Bowman, was another problem for another time, because I still needed to sort out the Jennifer situation.

Now, if I'm being honest, if I'd thought at the beginning of this school year that I'd end it with a girlfriend, I likely would have imagined a girl like Jennifer. We were both nerds, both similarly invisible at school, and both leaning toward the average end on appearances. Even with the long-sleeved shirts and paint-splattered overalls, her hair up in a ponytail and face largely hidden behind a fairly large pair of glasses, I could definitely tell that she was leaning toward the cute side, with smooth, pale skin and big, expressive brown eyes. Her guarded smile, when she chose to show it, was actually rather bright and lovely.

"So... you want to be my 'apprentice'," I said, the words still sounding alien to me. I was trying to process her request, which would have been odd under normal circumstances, but was outlandish in my currently high state.

"Yes, that was, uh, my general intention," Jennifer replied.

"Sorry, I've had a long day and I'm pretty wasted. You're gonna have to clarify your definition of 'apprentice' for me." With sitting up being a true challenge, I was feeling dull and direct.

Her eyes darted to me, then away from me, clearly in discomfort over having to spell things out for me.

"Look, I know you barely know me and I barely know you and this is a lot to put on you all at once, and... and I'm bad at this, not doing a good job, I'm being stupid..." Jennifer said, her words as fast and nervous as I was slow and sluggish. All I could do was gesture for her to continue.

Jennifer gulped, pulling herself together and explaining, "Well... I want to have sex."

"I got that," I replied.

"A lot," she said.

"Okay... and that hasn't happened?" I asked.

"No," she replied.

"Why not?" I asked.

"Because it's not that easy," Jennifer said.

I looked Jennifer up and down, and though I couldn't see much with the way she was dressed, the cuteness potential I saw seemed really at odds with this fact. With that in mind, I took a stab at what seemed the most likely explanation.

"It's a confidence thing?" I asked.

She nodded. "Yeah... I know what I want... I have a pretty good, you know, sex drive, and I really want to have sex. Whenever I'm at school, all I'm thinking about is how everyone else seems to be having sex but me, and I'm tired of it, but I don't want to rush into it either. I don't just want to go out there and have sex with random people like I'm whoring myself just so I can say I've done it; I want to be in a place where I can *choose*. That's the hard part. If I could learn from you, get some tips on how you became as 'popular' as you are, I think I could really start having the year I want," Jennifer explained.

"And it's a year full of sex?" I asked.

"Yes... I mean yes, but not *just* sex. I want that, but I also want attention, and friends... a little popularity never hurts either... Basically, I want the experience you've had. I want to be seen! I want to surprise Regan Hills High School, like you did, and I want to do it before I miss my chance," Jennifer said, smiling nervously.

I thought about what she said, and it was a lot to take under consideration. I'd tutored people in academic studies, but sex and relationships were something else entirely. I had gained a lot of firsthand experience in these fields, to be sure, but was still new enough at it that I couldn't think of myself as an expert. On top of that, my experience with virgins was limited, and more often than not, I was happy to let the women I was with lead the way and just enjoy the ride. Being looked up to as the one with experience felt truly daunting.

I tried shaking my head to get some clarity amongst the weed haze. It didn't work, so I had to ask, "And just to be clear, you're suggesting that we..."

"Have sex? Oh, yes, that was part of the plan I was really hopeful for," Jennifer said, smiling more brightly. "I've heard that you're really good, and, uh, big, and very caring, and I think someone like you would be very good to help me with my 'virgin' issue, if that's something you're up for, of course."

There was that V-word again, making me shuffle in my seat nervously.

Jennifer must have noticed this, because she started speaking more rapidly and nervously, "But you don't have to worry about me; I've been, uh, training with some sizable toys, and though I'm sure they've got nothing on you, I don't think you'd actually hurt me, and I think from what I've done and what I've seen in porn and think I can do that I might be, you know, really good for a first-timer and really fun for you?"

She bit her lip in what felt like a practiced attempt at seduction, as she got up and moved into the chair next to me. Her hand fumbled aimlessly on my crotch, before her misguided grip closed a little too hard on my balls. When she realized her mistake, she quickly backed off.

"Sorry! Sorry, that wasn't supposed to go like that, stupid, stupid," Jennifer muttered, looking down and shaking her head.

"You're not stupid," I said.

"I definitely feel stupid! If I wasn't, that wouldn't have happened and we'd be all, you know, messing around right now instead of me messing everything up!" Jennifer exclaimed, standing up and stepping away, nervous and a little afraid.

I should have gotten to my feet and calmed her down, but tired and high as I was, I stayed in my seat as I said, "You're not messing anything up, you're just inexperienced, it's cool. And, being fully honest, my balls are so drained it'd practically take a necromancy spell to get me back. Aside from that... it took me a long time to get anything close to what I'd call confident, and I still have to battle my insecurity all the damn time. It's fine, really."

I motioned for her to retake her seat next to me, and she accepted.

"So... you'll teach me?" Jennifer asked, her eyes hopeful.

"I... I don't know," I said, and seeing her begin to react negatively, I added, "I had a very long day and I am both high and exhausted. I don't know if I can make the best decisions right now when I can barely sit up."

"Sure," Jennifer replied, sounding anything but sure.

"I can see that you're nervous. And... honestly, I need you to be sure that this is what you really want, and that I'm the guy you want to guide you. I can barely guide myself half the time and usually rely on other people to tell me what direction's up," I said.

She balled her hands up, but then released them, some nervous energy dissipating.

"I did come here asking specifically for your help, didn't I?" Jennifer said, her voice slightly firmer.

She had a point there.

"A lot of experienced people really helped me out this year when I needed it most. So... yes, it makes sense to help you. Just... let's think on it, okay? Guiding someone I barely know into this life, it's a lot of responsibility. So, why don't we both take a couple days and think this out?" I suggested.

"A couple days? You're just trying to get rid of me, aren't you?" she replied, skeptical.

I pinched the bridge of my nose. "I need time to recover from today, and I've got some obligations this weekend that make time a little difficult to juggle. Please don't think I'm saying no, I'm not saying no, but I want to be sure I'm the right person for, uh, the job. Does... is that acceptable?"

I reached across to her, gently touching one of her nervously balled hands. Though she nearly recoiled instinctively, she didn't fully leave. That was something.

Taking a breath, Jennifer said, "Yes."

"Cool. Then why don't we sit here and eat some more of these delicious cookies baked by my archnemesis' mom and get to know each other? No pressure for anything else tonight?"

Nervously, Jennifer smiled at me, "Yeah. I'd like that."

"Me too," I described, taking another cookie. "Because these are pretty good cookies, and I've still got the munchies."

"I don't, but they are good," Jennifer admitted. "Why did your archnemesis' mom bake you cookies?"

I laughed. "It's a long story."

"Well, you're not kicking me out anytime soon, right?" Jennifer said.

Come to think of it, I wasn't either. Dipping my cookie in milk, I said, "Well, it all begins around homecoming..."

***

"Oh, god yes! Fuck me! Fuck me harder!" she moaned, the girl beneath me wrapping her arms around me as I rapidly slid my cock in and out of her pussy. The muscles of her cunt gripped me tightly, squeezing and pulsing as they encouraged my orgasm. Luckily for her, I wasn't a greedy sort, and though I'd already made her cum twice with my mouth, I wanted to make it happen again with my cock buried deep within her.

"So good... you're so fucking good..." I groaned, looking down at her sweet, smiling face as I defiled her pussy. I wished that we could get louder, but given the circumstances a bit of discretion was important.

We didn't want to be interrupted, after all.

Her legs hooked over my shoulders, I had her bent in half as I roughly fucked her with all ten inches of my thick cock. She might as well have been made of rubber for how easily I could twist her and bend her in any position that suited our dirty needs.

Our dirty needs that were rapidly reaching their necessary conclusion. Her eyes, already looking so big behind her glasses, widened in a look I knew all too well, and with discretion in mind I put a hand over her mouth as she tensed up, crying out loudly in orgasm as she shook against me. The way she clamped down on my already quite swollen cock, I had no choice but to cum as well, releasing deep inside of her. Pleasure overtook me as I tried to give her every last drop, each thrust weakening me further but feeling oh so good.

Both of us panting, I climbed off of her and laid down beside her in her bed. It was narrow, but so were the two of us, so we could mostly manage.

"That was... wow..." I admitted, looking over at her admiringly. Only covered by a blanket from the waist down, I got the perfect view of her firm tits, rising and falling with each breath, the flush way her cute face looked after sex that I'd come to enjoy so.

"Tell me about it," she replied, smiling at me. "You know, I think we get better at that every time."

"You might be right," I said, smiling back.

After all, who was I to argue with Sarah Kent?

The petite and toned blonde cheerleader lay back in her bed looking sublimely satisfied, her head turned to me so she could look at me with her bright green eyes behind her trademark horn-rimmed glasses. When I'd first met her this year, I thought that she was one of the shyest people I'd ever met.

Getting to see her blossom over the past months had been one of my favorite parts of the year.

That getting to see her blossom also tended to involve seeing her naked and fucking her in any number of creative positions, well, that was all a bonus. She was definitely hot, with a toned body from all her years in dance, a tight ass, soft yet firm B-cup tits that looked oh so delicious right now, and a face that could brighten an entire room every time she smiled. In a way, I related to her more than most of the girls I'd met this year. I mean, she was definitely more sexually experienced than I was at the beginning of the year, but we'd both had similar levels of confidence that we needed to work through. I liked to think that we'd helped each other, and though we both still had a ways to go, we made great friends.

"We should really actually get around to studying at some point, shouldn't we?" I asked.

"Yeah... three times enough to wear you out?" Sarah asked in reply.

I laughed. "I sure hope so."

This wasn't entirely a lie. I'd come over to Sarah's house this weekend so we could have a bit of a study date, her helping me out in math while I helped her out in history. I had every intention of going through with this, but when she greeted me in her pajamas looking so cute and innocent and horny, well...

Okay, I couldn't be blamed for letting her tackle me to the bed that first time, letting her suck me until I was nice and hard, then her riding me until we both came hard, right? That was just to get it out of our systems.

After that, we really meant to study, but when she got up on her tiptoes to get a book from the shelf and I saw her pajama bottoms fall just enough to show me her ass... well, okay, I got nice and hard again, and I couldn't help but bend her over her bed and fuck her ass hard until she was screaming into a pillow.

That was the second time. We both stripped down and washed up after that, vowing to stop having sex and actually study.

You can see how well that worked out.

"Me too... I need a good grade on this test," Sarah said.

"You'll be fine," I said.

"I know, but I want to be better than fine. I want to kick that test's ass," Sarah said, smiling proudly.

I smiled back. "Then I'll help you kick its ass."

"Good," she said, leaning over to kiss me. "Because if you can get Kaitlyn into shooting range of straight-A's, I know you can get me a step and a half past acing it."

"I'll do what I can," I replied.

"I know," she repeated, kissing me again. "Don't get me wrong, I love the cheer squad and they've done miracles for my sex life, not that things were ever bad fooling around with Josie, Hope, Fatima and Mia, but outside of Dakota, Sasha and Brooke, they're not much help for academics."

"Oh? And how are things on the cheer squad?" I said, willing my cock out of any hardness and finding it very difficult when reminiscing on the New Year's party I spent fucking the majority of the senior cheerleaders.

"Busy. Dakota rides us hard, but she's fair, and she's a great dancer and smart enough person to respect my input, which is helpful. We haven't done anything like New Year's since, if that's what you're asking, but we've been having *some* fun," Sarah teased, smiling at me almost shyly. "Brooke's been introducing me around to some of the football players, and it's been... nice."

"Nice?" I asked, laughing.

"Nothing like you, but you're not always available, and sometimes, sorry, a girl needs a good dick or five, and a lot of them can give good dick," Sarah laughed back.

Fuck I loved hanging out with Sarah. She was always a breath of fresh air, just happy to relax and have some no pressure fun together. She was one of the nicest, sweetest, and smartest girls I knew, which is what brought me around to a subject I'd broached earlier, but we'd been too busy with sex to actually approach.

"So, have you put any thought into what I was talking about earlier?" I asked.

Sarah stroked her chin with a finger and then asked, "Was it about how you can't believe how tight my ass stays for how much you've fucked it? Because I keep telling you, dance girls know how to keep it tight."

"No, I was-"

"I know what you meant, silly," Sarah laughed, looking up at her ceiling as she thought. "Jennifer."

Ever since I sobered up after my day with Jess, I'd been uncertain about how exactly I wanted to handle the responsibility of introducing Jennifer into my world. While part of me wanted to invite her in with open arms (among other things), I just wasn't sure that I was the right person to do such a thing, and that even if I was, I was afraid of messing things up. Slowly and quietly, I'd been going around to some of the people (save for Josie and Brooke, who I knew would encourage me to fuck around no matter what) I trusted the most and asked for advice.

Kaitlyn said I should go for it, and that if I was too afraid, she'd be happy to have another slut in training.

Rose said it was an interesting idea, but that if I wasn't comfortable with it, that could end messier than anyone wants.

Mrs. Lynn said that if it's Jennifer's choice, then I should encourage her to follow her path. Then Mrs. Lynn sent me a tit pic. Gotta love Mrs. Lynn.

Mrs. McNeil on the other hand said it sounded like Jennifer was uncertain and confused, and might need to talk with someone she was close to to be sure.

Jess texted me a couple of big thumbs up.

Alice was cautious, but urged me to sit down and talk with her.

Dakota sounded enthusiastic for the idea, but since I think I might have interrupted her sitting on Haley's face, I couldn't be sure.

Naturally, Rachel McNeil offered the best advice during one of our long-distance Skype sex sessions, telling me to talk with Jennifer now that my head was clear, and tell her how I was feeling and see if I could get a better understanding of where her head was.

That... was probably the best advice, but it didn't mean I wasn't going to keep asking around to see if someone might have had the magic bullet that would explain everything. Something within me seriously hoped that Sarah would be the one to possess it.

"I know her, a little," Sarah said.

"You do?" I asked.

"She's quiet, keeps to herself mostly, and it's not like most of us quiet and shy types are all in this one big club-"

"Or formerly quiet and shy types," I interjected, poking Sarah playfully.

"Hey, I'm still mostly quiet and shy, now I'm just quiet and shy and dressed like a cheerleader. The guys go crazy for it. Girls too, actually," Sarah admitted, rather proudly. "I'm doing damn good for myself."

"No kidding," I replied.