Senior Year Memories Ch. 43

As usual, the room was a mess that smelled of old clay and dry paint, its walls and cabinets plastered with old paintings and charcoal sketches that looked ominous in the mostly dark room that I'd stumbled into. As with most parts of the school that had been forgotten to time, it had clearly fallen into disuse and was used now more for the storage of disused furniture that nobody had any idea what to do with, but couldn't part with for one reason or another. Though the impressive space of the room would've made it great classroom space, it looked mostly like Regan Hills High School would rather forget that it existed.

Bad for them, but great for the aspiring artists, and those seeking out a lunchtime tryst...

"Hey, Ryan..."

Speak of the devil...

Her voice was halfway between sexily confident and timid, but as I turned to face the girl, I realized that I would have expected nothing less from my sometimes protégé, 18-year-old Jennifer Cage.

She looked about as lovely, and on brand, as I'd ever seen her around school. The 5'6", curvy brunette had her long, dark hair pulled back in a ponytail and wore a casual t-shirt and paint-spattered overalls that barely did anything to hide her impressive bust and ass. Her pale, soft skin prickled with gooseflesh as she stood there looking at me, while her lovely, well-rounded face beamed at me with a broad smile and lively brown eyes behind her glasses. When she'd first approached me about a month prior, she'd been a lonely art nerd and virgin who'd envied my senior year adventures and wanted to be taken under my wing. Though I felt thoroughly unqualified to be a teacher of this particular subject, I did my best, helping her break out of her shell.

And I helped her lose her virginity, which was pretty damn fun for both of us.

Though I hadn't spent as much time with her recently as I'd have liked, she still texted me periodically, keeping me updated on her adventures and making me thoroughly proud. I'd never thought I'd find myself in a position to have an apprentice, but here we were.

I liked to think the arrangement was good for both of us.

Looking over Jennifer, I grinned and prepared to greet her.

She was faster than I was, however, charging toward me and throwing her arms around my neck so she could kiss me deeply and enthusiastically. I returned the kiss, wrapping my arms around her, letting my hands drift down to squeeze her ass as we made out. Every time I'd kissed her, she only seemed to have gotten better at it, keeping it enthusiastic without letting any impatience overtake things as we kissed. Feeling her moaning against my lips, her tongue as eager to explore my mouth as mine was hers, I practically melted into her, the two of us really getting into the moment.

I had to break it for a moment, if just to catch my breath and smile at her, running my hands up the sides of her body. "Well, that's one of the more excited hellos I've had in a while."

Jennifer kissed the side of my neck, then smiled up at me. "Well, you were late, and we've only got so much time, and I want you, so... sorry if I'm a little hurried."

The little smile she had while saying that told me she was anything *but* sorry. I ran my hands up and over her large, DDD-cup breasts, squeezing them and making her moan, before I reached up to unclip the straps of her overalls.

"Well, let me make it up to you..." I said, kissing her and tugging her overalls down.

Jennifer groaned as I pulled the garment down, particularly as I reached the flare of her fairly epic hips. I again took a moment to enjoy running my hands over and gently squeezing her large, round ass, before I dropped the overalls around her ankles.

Lowering my voice, I hissed, "Now, bend over that table..."

Smirking at me appreciatively, she followed my instruction, leaning against a nearby art table and thrusting her ass out at me. I ran my hands lightly over the simple cotton underpants she wore before lightly tracing my fingers up to the elastic of her waistband.

I knelt down behind her, getting up close and personal with her curvy, underwear-clad ass. Playfully, I bit her on the ass cheek through her underwear, making her groan softly.

"You're such a fucking tease..." Jennifer chuckled, turning back to look down at me.

With one swift movement, I pulled her underwear down to the floor, revealing her bare ass to me. Playfully, I swatted her on the ass with one hand, the sharp sound particularly loud in this empty room, though not quite as loud as her surprised yelp.

"I've learned to be an *exceptional* tease, thankyouverymuch," I said, biting her on her now exposed ass before smacking her again. "So, I take that as a compliment."

"I meant it as one," she replied, a pleasant confidence to her voice as she jutted her ass out even more to me, better exposing her pussy lips to me. Even though it had been a minute since Jennifer and I had last hooked up, my mouth watered at the sight, fondly remembering her taste and her gorgeous pussy, framed by dark, well-trimmed pubic hair.

I looked at those glistening lips now and leaned in, inhaling her scent and groaning in spite of my efforts at trying to sound calm and cool. Jennifer clearly enjoyed this, moaning softly as she pushed her ass out toward me more.

"You want a taste?" she asked, wiggling her hips and pushing her pussy closer to my face. "Oh, I know you want a taste. I'd want a taste of me too if I had the chance. I've got a nice pussy... a *really* pretty pussy, and it tastes so fucking good... so you want a taste, don't you? I want you to lick my pussy like you know how I like it... I want you to eat me out until I'm cumming on your face. You want to do that, Ryan?"

I nodded, impressed. When I'd first started teaching her what I knew, Jennifer had been awkward and a little stumbling, though thoroughly enthusiastic. Now, however, she had a growing confidence that I rather enjoyed seeing unfold before me, and I was excited to see where it would take her next.

Playfully, I stuck out my tongue and ran it over her slit, lapping up her moisture and enjoying the way it made her moan a low, pleased cry of pleasure. She tasted good, better than I remembered, honestly, and it seriously tempted me to dive in and just go to town on her pussy. However, the way our schedules lined up lately, or *didn't* seem to line up, I felt like drawing this out if I could, and so took it slowly, exploring her folds without diving in. No matter how much she arched her back and pressed against me, no matter how much she tempted me, I kept it slow, which only made her groan all the more.

"Oh, you're being a real bastard about this..." she moaned, reaching up with one hand to squeeze her tits.

"Uh huh..." I replied simply, gently pressing my tongue into her folds and thrusting it in and out, never too deep, but just enough so that she'd know what I was capable of.

"Fuck..." Jennifer groaned, pulling her shirt up over her tits, then pulling her bra down. Not being able to see her beautiful DDD-cup breasts from this angle was a definite disadvantage of our current position, but knowing that she was lost to pleasure and squeezing her nipples made it well worth it.

After briefly running my tongue over her clit, I pulled back, leaving her whimpering and thoroughly hot and bothered.

It felt like the perfect time to keep up the tease, so as I reached up to lightly massage her clit, I said, "So... what've you been up to lately?"

Jennifer looked back at me as if questions should've been the last thing on my mind at the moment, but even though I had intended it as a tease, I was actually hoping to catch up with her a little. That brief blaze of fury and sexual frustration on her face might have been a problem, but then that look changed. Then there was a flash of that confidence that I'd been enjoying, and she quickly shot back to me.

"Well, if you eat my ass and finger my pussy a little harder than that, you might persuade me into divulging some of the juicier details of my life to date," Jennifer said.

As offers went, this was a pretty good one. You didn't have to twist my arm to eat a girl's ass, especially one as perfect and epic as Jennifer's, and after our earlier experiments with anal play, I knew this would get her off particularly hard.

She flexed her ass cheeks at me, exposing her tight, enticing hole. "So... what's it gonna be, Ryan?"

I think it should be little surprise at this point that I dove in, sliding two fingers from one hand into her pussy while I rubbed her clit with the other, while my mouth soon latched onto her asshole. I licked and sucked, running my tongue around her tight, forbidden hole with gusto, making her brace herself against the table while she moaned and writhed.

"Oh... oh, FUCK!" Jennifer cried out, laughing and moaning all at once. "That's... hahaha, oh fuck, that's amazing... fuck... fuck, fuck, fucking *fuck*! That's amazing, fuck, keep going, like that, please... oh, god, I love the feel of your tongue on my ass..."

I pulled back quickly, just long enough to ask, "So... weren't we catching up?"

Before she could complain, I dove back in, licking and sucking and actively tonguing her ass while I fingered her pussy. Rather than say anything, she stood there, moaning and shaking for a while, completely lost to this pleasure. I could've slowed down, teasing her and waiting for her to respond, but after enough teasing already, it seemed appropriate to indulge her this time.

Soon, even with my best efforts to get her off, Jennifer regained her wits, moaning as she replied. "I've been... fuck, I've been great! Goddamnit, keep going, FUCK!"

Rather than prod her anymore, I doubled my efforts, pleasing her with my fingers and tongue more eagerly while she writhed and moaned, letting her tell her story at her own pace. Admittedly, I made this a particularly challenging prospect for her to describe her own recent adventures to me, but that was part of the fun in its own way.

And if this had been the Jennifer I'd first really started chatting with one month ago, she probably would have been a moaning, crying mess at my efforts, barely able to string two sounds together, let alone words, but with her experiences this past month, she had her wits about her rather impressively.

Groaning and squeezing her tits, Jennifer explained, "Well... fuck... you know about me with Peter & Sasha... they're so fucking nice, god, yes, eat my ass like that, fuck, keep going... they introduced me to Cleo, who's a lot less nice, but likes her girls thick and knows what to do with me... I've gotten with a couple jocks, who were alright... a couple goth chicks, who were *much* better than alright... I've even started dipping my toes into the drama kids."

Even with my tongue working its way into her asshole, I couldn't help but smile at that thought. We'd talked about the drama kids some time back, and I knew Jennifer had some light crushes on more than a few of them. That she'd actually had the chance to make that fantasy come true in some capacity, well, that made me proud.

I speared my tongue into her ass, thrusting it in and out of her briefly and really getting her going. Jennifer was beginning to let herself lose it, her body tensing and quivering as I continued to finger and tongue her.

"Yes... yes... harder... more..." Jennifer moaned.

Pulling my tongue out of her ass, I smacked my lips and smiled. "Which drama kid?"

"Keep going... I'm close..." she whimpered, pushing her pussy and ass back against me. "It was... Zahra... Zahra Dashti."

Huh. Well, this certainly got a lot more interesting. Zahra, a pretty and kinda nerdy girl of Middle-Eastern descent, was one of the potential leads for the spring play that I was supposed to interview. Considering the fact that I didn't want to have to lean on Olivia any more than I had to to accomplish my paper assignments, if I had a potential in with someone who knew one of the four girls that I was supposed to interview, well, that was helpful, wasn't it?

So, maybe I went at Jennifer a little more enthusiastically than I already had been. I ate her ass and fingered her pussy with gusto, wanting to get her off and make it utterly devastating. I wanted to do this to please her, of course, but maybe I added a little extra hurry into the equation after she mentioned Zahra's name, squeezing her clit in such a way that she couldn't help but cum hard, and fast. Jennifer cried out quickly, clapping a hand over her mouth to ensure she wouldn't get too loud, while her pussy gushed and spasmed and overall completely lost it. The quiver and shake in her body got me thoroughly excited, making me treat her ass and pussy with all the more worship as she slowly came down from her messy orgasm.

"Fuck... oh... oh god... oh fuck..." Jennifer groaned, pushing me away gently as she wobbled to the nearest chair and sat down. "That was... fuck, you still spoil the hell out of me..."

Then, giggling lightly to herself, she added, "Makes me glad I'm saving my ass for you."

Still kneeling on the floor, I smirked. "I'm honored."

"You should be. A lot of guys have wanted to be the first, but I'm saving my ass for you. For now, anyway. I know you're busy, and with these encounters between us so few and far between, some lucky guy or girl might catch me in a weak and generous mood and... well, things can happen," Jennifer said, grinning with good humor.

I'd heard worse encouragement to get off my ass and fuck someone, and that it came from someone who a little over a month ago was making truly awkward come-ons and was so uncertain of herself, well, I couldn't have been prouder of her.

Jennifer must've caught my smile, because she returned it sweetly. "I'll return the favor, if you want. I'd love to blow you."

My cock twitched at the thought. "Sure. I'd really like that. Can I ask you something first, though?"

"You can ask me during; we don't have a lot of time left for lunch, and I'm *seriously* hungry for cock," she said, dropping to her knees from the chair and encouraging me to stand. I got to my feet, enjoying the way her shaky hands unbuckled my belt.

"Alright... how close did you get to Zahra?" I asked, groaning as she dropped my pants to the floor and playfully squeezed at my erection through my underwear.

"Beyond sex?" Jennifer replied, pulling my underwear down and freeing my thick, 10-inch cock so quickly it bounced upward, smacking her in the cheek. She giggled at the contact, playfully running her fingers over my shaft and stroking me, easily teasing out some precum once she began massaging the head.

She continued, "We're friendly enough, though I wouldn't really say we're close. Why?"

I explained why I was looking for Zahra, and for her part, Jennifer dutifully listened. She, of course, did this while first sucking, and then deepthroating my cock, which I rather enjoyed (she had *really* been improving her technique), even if it made it rather difficult for her to answer. I went into as much detail as I could, even if it was a challenge under my current circumstances, but I like to think I got all my points out there while thoroughly enjoying her amazing blowjob. Thankfully, my explanation wasn't very long, and by the end of it, neither was Jennifer's blowjob. I'd gotten pretty fucking turned on eating and fingering her, and with this cute and curvy and mostly naked art student kneeling before me and giving me some absolutely amazing oral, there was no way I could last very long.

After a few minutes like this, I grunted, grabbing Jennifer by the ponytail as I came down her throat. She swallowed to the best of her ability, her throat working overtime as she tried to take down the sheer volume of my cum. Without thinking, I pulled back slightly, and I could see her mouth filling, but impressively she managed to get every drop down without a mess. With only my cockhead in her mouth now, she licked the tip and swallowed the last bit playfully, before looking up at me.

"Good?" Jennifer asked.

"Good," I replied, dropping into a nearby chair for a moment. "Fuck, that was... that was good."

"Thanks!" she replied, smiling sweetly as she quickly got dressed. "I've been working on building my skills. It's a process, but practice makes perfect, and I *love* the practice."

I laughed. "I can tell. So..."

"Right," Jennifer answered, pulling her shirt over her head. "I mean, I can tell you all I know about, or you can find out for yourself. That's usually best, right? I can give you her phone number and you can text it out, or if you're adventurous... no, never mind, you probably don't want to do that."

Well, with an introduction like that, how could I *not* ask follow-up questions. "I can be adventurous."

She smirked. "I know you can be adventurous, it's just that there are degrees of adventure, and I know some of them are more within a comfort zone than others. And Zahra's..."

"Yeah, I still need to hear more. You can't not tell me at this point, you know," I replied.

Jennifer kept smirking. "Well, Zahra's really into LARPing, you know, Live-Action Roleplaying? It can be a little silly, but I think she enjoys doing it because she gets to act without a script and just cut loose. Well, anyway, she's got this group that meets at Macready Park once or twice a week, and I think today's one of their meet-up days. If you can get a costume, they'll probably let you in, and it would give you a more interesting way to get to know her. Should make for a much more interesting interview."

Alright, maybe Jennifer had me when it came to pointing out things that would and wouldn't be within my comfort zone. My previous experiences with role-playing games had been limited and unsuccessful at best, and that was without the pressure of needing to actually *play* a character in any serious way. It probably would have been a lot easier, all told, to simply get her phone number and text her, set up some meeting in a neutral location and interview her that way. I wouldn't have to worry about costumes and roleplaying and any of that mess, and could handle things on my terms.

But, where would the fun in that have been?

"Just what kind of costume should I wear, exactly?" I asked.

***

Once upon a time, I would have been incredibly self-conscious showing up to a public place on a day that wasn't Halloween wearing a faux-medieval fantasy costume. That version of Ryan Collins would have been petrified at the possibility of having to do something like that.

A lot of time had passed since I was that version of Ryan. Now, as I stepped out of the car wearing that exact costume, I was only *slightly* self-conscious and scanning the park for any looky-loos who might choose this exact moment to spy me and laugh.

So, all-in-all, this was improvement.

Two factors helped further comfort me in this unusual situation. The first was that my costume was actually pretty dapper, a long-sleeved, off-white tunic with laces down the front over soft gray pants and comfortable sandals, topped by a dark leather vest and a wide peasant's hat that kept the sun off my face. My glasses weren't exactly period appropriate, but still necessary if I wanted to do pretty much anything, but I didn't look as foolish as I could've. A little on the un-flashy side to be sure, and nothing fit perfectly, but considering the fact that these were borrowed as a favor, I wasn't going to complain too much. I could make the peasant chic look work for me.

The second factor aiding my comfort was the source of this costume, who also happened to be my ride and companion to Macready Park.

Or, to be more accurate, I was *her* companion on this day.

She stepped out of the driver's seat of her car, a flowing, silvery and pale blue dress seemingly hovering around her, every bit as ethereal as the archetype she was seemingly embodying. The slightest of heels made this normally 5'10" girl taller than me, while makeup accentuated her normally elegant physique and pale skin into looking all the more fantastical and otherworldly. With a pair of pointed ears poking out from the sides of her shimmering, long, wavy blonde wig, Mallory Dourif looked like she'd put every one of her cosplaying skills to work to appear an elven sorceress.