Senior Year Memories Ch. 34

(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: 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 readers; your support and input really help make this possible.)

Previously, on Senior Year Memories: After greeting cute nerd Jennifer Cage on his doorstep, 18-year-old Ryan Collins hears her out on her desire to become his sexual apprentice. While he turns her down in the short term, he solicits advice from his nearest and dearest friends to help him make his decision. When February brings around a feeling of Valentines in the air, Ryan takes up the offer to join his co-worker on the paper, sexy Wiccan girl Leah Sartori, for a sexy spell to send good vibes of love and lust to the town of Regan Hills. The two of them took place in wild, ritualized sex before Ryan came to an epiphany where he decided to put his skills (and cock) to the test to help the lovelorn of Regan Hills, and decides to start by taking on Jennifer.

***

While it was still very much in the planning stages, I was definitely beginning to figure out the shape that February was going to take. The cast may not have been set in stone just yet, but there was a likely list of players, and between the Valentines I'd been receiving and some leads that Josie, Brooke and I had put together, it was looking like my dance card was going to be quite full if all my plans came to fruition.

Did I regret it, though?

No, not for a second.

I was actually excited to see where the month would be taking me. I was less nervous than usual, as my confidence had been slowly but steadily growing for some time by this point, but there were a few areas where I was still going into relatively uncharted waters that could still bring the nerves to the forefront.

Preparing, both mentally and physically, for what was going to happen with Jennifer, for instance... that was going to take some doing.

It was after school, and since Dad had that Viking cooking class he taught every other week, he was going to pretty much be gone for the night. I had also asked Josie and Brooke to stay away for a bit and give Jennifer her space; they were going to spend that time hanging out at Alice's house across the way, so they would be nearby for the juicy details.

That left me, alone, in the house, running around like a chicken with its head cut off as I tried to clean the place up. I got my room in order, got some snacks and drinks ready in the kitchen, showered and shaved, and managed to get dressed just in time in a comfortable t-shirt and sweat pants as I heard the knock at the front door.

"You got this," I said to myself as I approached the door. "She's coming here for your help. You want to help her, you know what you're doing, just relax and have fun. There's no pressure at all, you're just... helping her lose her virginity and introduce her to the world of sex at Regan Hills High and all that entails."

If I meant to lower the pressure, I failed. I should've just stuck with saying, 'You got this.'

Nodding, I said, "You got this."

Unlocking the door, I swung it open.

"Hello," I said, stepping to the side to welcome 18-year-old Jennifer Cage in.

"Hi," she said, meekly, stepping inside as I closed the door behind her. At 5'6", Jennifer was neither a big or truly small girl, but the way she carried herself I could tell she felt very small. She was pale and a little nervous-looking at the best of times, and now she looked like she wanted to hide behind her long, dark brown hair, but the way it was tied back in a tight ponytail, that wasn't going to happen. Her big brown eyes looked even bigger behind her trademark glasses, while her soft-looking lips were curled into a smile that hoped for confidence and couldn't find it. As expected, she was dressed in her paint-spattered overalls and a loose, long-sleeved shirt, and while she may not have been the most gorgeous girl in school at a glance, her round, friendly face was definitely leaning toward cute.

"You can set your backpack and shoes by the door," I explained, watching as she did so. "I've got some snacks and sodas in the kitchen if you want, or water, or, well, pretty much whatever, and I've already pre-ordered some pizza to show up in a bit."

"That all sounds good," Jennifer replied, her voice soft and quiet. "Got any more of those cookies?"

I laughed. The last time we talked here, we had done so over cookies that had been mysteriously left at the door by Karen Bowman, mother of my bully, Kyle. They were good cookies, but I was happy that I hadn't yet had to hear from her.

"Fresh out, sadly," I said.

"Oh, that is a little sad," she replied, though she was smiling. "I'll grab a soda first, I think."

Jennifer knew the way to the kitchen after our last encounter, but I led the way anyway. She grabbed a Sprite while I grabbed a Coke, and the two of us sat at the kitchen table, drinking opposite each other as we looked at one another. I was nervous about what was about to happen, but I knew that I couldn't be nearly as nervous as she was under the circumstances.

After all, it wasn't every day you lost your virginity.

"Are you alright?" I asked.

"I'm fine," Jennifer replied, her voice shaky and soft. "Why?"

"It's nothing, it's just... I know that what we're doing here is going to be a pretty big deal, and I want to make sure that what we're doing is something you *want* to do," I said.

"It is!" Jennifer said, quicker than she clearly wanted to as she leaned back in her seat, nervous. "I definitely want to do this, I'm just... well, I'm just a little nervous, that's all."

I smiled, reaching out across the table to touch her hand. She slowly warmed to my touch, turning her hand over so we could clasp them together.

"It's going to be fine, really," I said, reassuringly. "We take this at your pace, do whatever you want to do... and remember, this is something *fun*. If you're not having fun, there's no pressure to keep going."

Jennifer smiled at me again. "Thanks."

"No problem," I replied.

"No... it is a problem, well, it's sort of a problem," she continued, her voice rising with frustration and anger with every passing word. "I'm making it a problem when it shouldn't be, because I'm overthinking all this shit because my mom makes me overthink everything and I don't want to be overthinking everything, I just want to love myself and have fun instead of thinking about all the bullshit about sex that's been fed to me my entire life because I'm eighteen fucking years old and an adult and I can make my own choices and... and... I'm sorry, that's too much. Fuck, I'm messing things up again..."

I squeezed her hand. "You're not messing things up, I swear."

"Yeah?" Jennifer asked, looking down at her drink.

"Yeah. It'll take a lot more than that to scare me off," I said.

"Thanks," she replied. "It's... I'm nervous. That's okay to say, right? I'm nervous, maybe even a little freaked out, but this is something I want more than anything else I've ever wanted in life. I... no, it's more than a want. It's a *need*. It's this need I feel inside of me, and if I don't do something about it, it's going to burst like an appendix and flood me with madness until all I can do all the time is scream and... yeah, well, you get the idea. I'm nervous, that's the thesis statement."

"A completely fine one," I said.

Jennifer nodded, still smiling nervously, but a little more at ease. "Was it this hard for you?"

"What?" I asked, briefly checking to make sure I wasn't tenting my sweatpants.

"The first time you... were with a girl," she said, her pale cheeks flush with blush.

Thinking back to the first time I'd ever had sex just five months ago, I laughed. "It wasn't... well, I didn't have time to think about it, honestly. It just kind of happened. One minute I was expecting to tutor her, the next minute she was trying to bribe me, and then, what do you know, a little while later she was riding me until she drained my balls."

"Wow," Jennifer said.

"I didn't have a lot of time to mentally prepare for it and know what was happening at the time, I just... kinda let it happen. I liked it, don't get me wrong, and I spent a while just kind of rolling with the punches and enjoying experiences as I stumbled across them, but I guess... well, you caught me at an interesting time in my life," I said.

"What about it is interesting?" Jennifer said, then looking sheepishly back at her soda. "I'm not saying you're not interesting, I mean-"

"It's okay," I said, attempting to calm her. "I know what you meant."

"Okay, okay, good..." Jennifer replied.

"What I meant was that after a while of letting the year happen to me, I'm ready to make my mark on it in my own way, on my own terms. So, the two of us really can get a new start on things together," I said.

Jennifer thought about this, looking up at me with the sweetest, most hopeful smile I could remember seeing.

"Yeah?" she asked.

"Yeah," I replied. "Today, we have some fun, get you laid, and we set you on the path toward you making your mark on the year."

"Mmm," Jennifer said, relaxing into her chair. "I like the sound of that."

"I was hoping you would," I said. "So, to know exactly what I'm working with, I'd really just like to ask you what kind of experience you have, what you'd like to do and, really, get an idea of where we should begin things. I know you said that you've been practicing with toys, but, I just want to get a better idea."

"Yes, that makes sense," she said, taking a sip of her drink. "It's not like I've never done anything, it's more like I've never done anything with another person. Never been kissed, never had sex with anyone or anything in between. What I have done is watch a lot of porn, not that that makes me special or anything, I know, and I've got a few good-sized toys. I've practiced with them in my mouth, and..."

She quieted at this point, probably less familiar with talking about graphic sex details with another person. That was something I could help with.

"Where else?" I asked.

A little bashful, Jennifer replied, "And my pussy. And..."

"Your ass?" I suggested.

Without looking at me, but still smiling a naughty little smile in spite of her embarrassment, she said, "Yes."

Jennifer eyed me cautiously, probably trying to gauge my opinion of her, and when all I could do was smile back, she looked enthused.

"And did you like these things?" I asked.

Jennifer looked up at me, a little bolder. "It was... different than I expected."

"How do you mean?" I asked.

"Well... my mom never really gave the best impression of what sex was supposed to be like, that it was supposed to hurt and only bad things came from it, but when I saw everyone having their fun, and when I started watching porn and saw things that looked fun, things that brought out feelings inside of me... I had to try. I started touching myself, and when I liked how that felt, I knew I had to up my game, so I bought my toys. They were... they hurt a bit, at first, but after I figured out what I was supposed to do with them, then they felt good. Really good. I really liked making myself feel good with them, and... well, I've done it a lot," she admitted.

I could see her gaining enthusiasm with every word. She shuffled in her chair slightly with a bit of delicious discomfort as if reliving some of these more enjoyable memories. This was something I could work with.

"So that's what you've done... how about you tell me some more about what you want to do?" I asked.

Straightening herself up, Jennifer said with every bit of confidence she could pull together, "Everything."

I grinned back at her, nodding. "Everything can mean a lot of different things. I want to hear precisely what you would like to try."

When I said this, it seemed like she had been hit slightly at my response, but wasn't deterred. "Well, I... I want to be kissed, that's simple. I want to be fingered and I want to touch a guy's... cock. I want to do oral, give and receive. I want to have sex, vaginal, anal... I want to have sex with more than one guy at once. I'm not sure if I'm into girls too, but I think I am, and if I am I'd like to have sex with more than one of them at once. I think... I might be into some kinkier stuff, I'm not sure yet, and I might even like to touch myself, or even have sex, in front of an audience. These are just basic ideas, I mean, hopes and-"

"All things that can be arranged for," I said.

"Really?" Jennifer asked, hopeful.

"Really. I've been through a lot this year, and managed all of that and more. With a little practice, and a little experience getting you out with some others, I don't think you'll have any problems," I said.

Jennifer smiled broadly, an unrestrained smile of great hope and joy. "You mean that?"

"I mean that, seriously," I replied, squeezing her hand again. "I used to think Regan Hills was meant to chew up and spit out people like us, that we wouldn't stand a chance around all the beautiful people, but with a little help, and a little motivation, we can really have all the fun we always dreamed about, but never expected to have."

"I... I like that," Jennifer admitted.

"Good," I said, finishing my drink. "Should we take this to somewhere a little more comfortable, or would you like to stay here for a bit longer?"

She looked down at her can of Sprite for a moment, a wave of nervousness overtaking her. She nodded to herself quickly, briefly, I think psyching herself up, but it was hard to say.

"I think I need to stop listening to all the bullshit my mom tried to teach me over the years, and start focusing on what I want. I'm a fucking adult, I need to act like one and start charting my own course," Jennifer said with a great swelling of finality.

Standing up from her chair, she declared, "Yes. Let's go somewhere more comfortable."

I took her hand in mine and led her down the hall toward my bedroom. I was glad that I had cleaned up the usual mess that threatened to overtake my room, changing the sheets and blanket on my large bed. Jennifer looked up in some wonder at the walls, with my movie and video game posters, stacks of comics and vinyl figures peeking out from almost every corner.

"This is... yeah, I think this is exactly the kind of place I'd like to have lost my virginity in," Jennifer said, looking at me with some nervous amusement.

"Yeah?" I said, closing the door behind us. With the door closed and the curtains drawn, it was definitely darker in here now than usual, but with the couple lights I had, I was able to keep the room from completely turning into a cavern.

"Yeah. Feels like the better parts of home," Jennifer replied, smiling at me cutely.

"Happy to hear it," I said, sitting on the bed and leaving plenty of room for her to join me.

I saw the realization of this hit her face, a slight shudder passing through her body as she realized that this was it. If she had told me in this moment that she wasn't ready and simply bolted, I wouldn't have held this against her for a second, though for her own sake I was rooting for her. I wanted her to be able to do what she wanted to do, because I could remember exactly what it was like being where she was. Jennifer just needed to take this last step on her own...

She did. Jennifer sat down beside me on the bed with a strange blend of enthusiasm and hesitation, her eyes widening as she sent my bed rocking with the force of her landing, smiling and giggling after she settled down.

"Sorry!" Jennifer exclaimed.

"It's all good," I said, enjoying the closeness with her. She sat only a few inches away from me, the two of us nearly touching but not quite. "So, are you ready for this?"

Jennifer looked away from me for a moment before turning back and nodding. "I think I'm as ready as I'll ever be."

"Good," I replied. "Because your lips look very kissable, but I'd like to find out to be sure."

"Yeah?" she replied, smiling and leaning slightly closer to me.

"Yeah," I said, reaching up to take her face gently in hand. I stroked her neck gently, causing her to shiver, then guided my lips to hers as I gave her her very first kiss.

It was a very wet kiss, and she was as eager as she was nervous, but who isn't their first time out? I made sure I was receptive, and encouraging, gently pushing my tongue into her mouth to meet her very enthusiastic tongue. I didn't give her too much, just a taste, a tease, enough to entice her and keep her interested until I broke this brief kiss.

Jennifer looked at me dreamily, gasping and moaning slightly at the sudden absence of my lips on hers.

"How was that for a first kiss?" I asked.

Words took a while to find her, but when they did, she replied, "Magical. And wet."

I laughed. "That'll happen."

"Can we do it again?" Jennifer asked, enthusiastic.

"Of course," I replied, leaning in to kiss her some more. I'd had enough experience to slowly guide her as we continued kissing. Cautiously, I reached around her with one arm, pulling her in close beside me so we could more properly make out, and was encouraged when she did the same with me. It may not have started out the most earth-shattering make-out session in the world, but she was enthusiastic and a quick learner, and soon we became lost in each other. Jennifer let out soft, low mewling moans as we kissed, grinding gently against the bed as we made out.

I broke the kiss. "Pretty cool, huh?"

"Very cool," she answered, practically purring as she leaned in to kiss me harder.

I separated again, wanting to guide her in a direction she would like. "What do you want to do, right now?"

Jennifer thought for only a moment before rotating on the bed, swinging one of her legs over me so she could straddle me. She wrapped her arms around my neck while I wrapped mine around her back, the two of us holding each other close as we made out. Jennifer was getting more enthusiastic by the moment, and I was too, since she could no doubt feel my fairly large erection at this point, but as she ground against me, I was becoming all too conscious of the thickness of her rough denim rubbing against me.

"Now, don't take this as a complaint, or me trying to rush you or anything," I said, loving holding her close as she rubbed on me and we made out. "But your overalls are pretty rough on my cock."

Jennifer's eyes went wide, her face suddenly bashful. "Oh my god! I'm so sorry, Ryan!"

"It's alright, just communicating," I said.

"That's something I can fix, though," she said with some enthusiasm, hopping off of me and the bed and standing before me.

Without breaking eye contact, she pulled her phone from her pocket and put it on my bedside table, then unbuckled each strap of her overalls and let them fall to the floor. Then, with a playful, hopeful little smirk, she pulled her long-sleeved shirt over her head and tossed it aside as well, leaving her standing before me in a faded gray tank top, a comfortable pair of dark blue panties, and her socks.