(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.
