Senior Year Memories Ch. 15

I did as she said, adding myself to her contacts. She pulled in close to me, pressing close. For the first time I realized that I never knew how large her breasts were beneath the conservative, drab clothing she usually wore, but feeling them pressed against my arm was enough to warm my blood.

Hope whispered in my ear, "You know, if you were to accidentally swipe over to the next tab, you'd find some of my own dirty pictures. They probably aren't as varied as yours, but I guarantee they're more exotic. You can see me naked. You can see my tits, those nipples pressed into your arm before your eyes. You can see my pussy. My ass. What they're capable of."

I was tempted. Sorely tempted. Hope may not have been my usual type, but I'd learned that what people looked like wasn't the best way to judge what they could do sexually.

Hope continued, her voice deeper, huskier. "You think you know sex, but you don't know the depraved shit us band sluts get up to. Spend a night with me and I'll curl your toes and make it so you can't walk straight for days, and do you wanna know the best part? You'll come begging for more. You'll ask to see what more I can do for you, what the other band sluts can do, shit, even what me and Josie can do. Just try not thinking about fucking Josie's ass while she's got a fist buried wrist deep in my pussy, both of us screaming and begging for more. Try."

"Why would I want to try that?" I said, finishing adding myself to her contacts and handing her back the phone. I didn't look at her pictures, much as I wanted to, because I wanted to give this image that I was at least somewhat in control of the situation.

Hope nodded. "I like your confidence. We'll talk soon."

"Looking forward to it," I said, watching as she confidently sauntered into the band room, impressive for a girl who looked as naturally awkward as she did. A while back I never would've given a girl like Hope a second glance, mostly because I was shallow about what I'd found hot, and she was far from the peak of sexy. Cute, maybe, from the right angle, but far from hot, definitely awkward and a bit of an oddball. Now I couldn't help but watch her walk away, just wondering if she was every bit as freaky as she claimed to be.

For that matter, if the band girls were all as freaky as she claimed.

With everything going so well, it was about time for something to go wrong.

"Ryan Collins?" a soft, stern voice asked from behind.

"Yeah?" I said, facing this new presence, and was greeted by the sight of 18-year-old Marie Halpern. Slim and about 5'2" with long blonde hair held up in a bun, she couldn't have looked more like a stereotypical librarian if she tried. Her light blue, conservative knee-length floral dress, knee high socks and horn-rimmed glasses made her look almost out of a cartoon, but no, she was just another of my classmates. She normally looked like she had a stick up her butt, but today she stood particularly rigid, perhaps in an effort to intimidate me because I was taller. If she didn't look so stern all the time, her face could've been incredibly cute, but as it was it felt like she could stare down a charging bull.

"Mrs. Sullivan would like to see you. Now," she said. Mrs. Sullivan was our school librarian, and someone I'd only just run into a few days prior while she was putting up Thanksgiving decorations.

"Am I in trouble?" I joked.

"She wouldn't have sent me to look for you if you weren't," Marie said. I read her face for any hint of a joke, but it took me too long to realize that Marie didn't joke.

"Wait, you're serious?" I said.

"Yes," Marie said. "Come with me, please."

Marie took a few steps away, leading me toward the library. When I didn't follow, she turned to me and gave me an impatient wave.

Why would I be in trouble with Mrs. Sullivan? Overdue books? Even if I were, which I wasn't since I always returned things on time, that was just a fine. We were on normally good terms, friendly if not exactly friends, and I always respected the library, and...

Well, there was that time a few days back when Josie and I had gone down on each other in the stacks and... oh fuck.

"Okay," I said, nervously following Marie to the library.

***

I'd never really been in trouble at school, partly because I'd always tried to follow the rules, but mostly because I never really did anything worth getting in trouble over.

The old Ryan Collins, the one that existed before this year, did his homework, sucked up to teachers without being obnoxious about it, and never did anything more hardcore than occasionally flip out if someone owned him at Magic: The Gathering.

The new Ryan Collins... well, he wasn't exactly a criminal, but since having sex on school property was definitely against the rules, he wasn't doing so hot these days on the "not breaking rules" front.

So, while Marie silently guided me to the library, letting me in and closing and locking the door behind us, I was fantasizing about absolutely everything that could go wrong.

If I was lucky, maybe I'd just get a reprimand and that'd be the end of it. I could tearfully apologize and promise never to do anything that stupid again and maybe I'd even be smart enough to avoid doing it that way but that could be hard if things kept going as they had.

If I was unlucky, words like "detention," "suspension," and "expulsion" kept swimming through my head. I'd have Dad in my corner and might be able to get a couple other teachers to vouch for me, so the latter seemed unlikely, but I had no idea how "zero tolerance" our school's zero tolerance policies actually were, so any number of things could've happened. The vortex of shit my social life was currently slowly spiraling around seemed to pale in comparison to what might happen to my academic career.

That the librarian, Mrs. Claire Sullivan, was waiting for us among the tables and couches of the study area, didn't help my anxiety any. Normally a friendly, warm presence, today her pretty face was every bit as stern as Marie's. For a woman in her early forties, she usually looked rather luscious, and today was no different. Her shoulder-length, chestnut hair fell onto her dark blue sweater that held back a phenomenally large pair of breasts, and her equally dark skirt was short as ever, showing off her black stockinged legs and heels nicely.

This look was normally one that would've drawn some pretty inventive fantasies, but the way she leaned against a table, casually drumming her fingers on a polished wooden box sitting on the table, made me feel like I was being walked ever closer to my execution.

"Hello, Ryan," Mrs. Sullivan said. "Please, take a seat."

"Yes, Mrs. Sullivan," I said, wanting to get this over with. I set my backpack down on a nearby table, grabbed a chair and sat facing her.

I felt like I was sweating bullets, even though I was completely dry. My heart was pounding, I was shaking slightly, just waiting for the ax to fall and tell me just what kind of mess my life had become. Marie stood next to Mrs. Sullivan, looking down at me judgmentally through her horn-rimmed glasses, while Mrs. Sullivan just stood considering me, still drumming her nails on the wooden box. Was I supposed to talk first? Was she? Were they just going to stand there staring at me, waiting for me to crack like I was on some cop show?

When Mrs. Sullivan finally spoke, she didn't exactly take the angle I was expecting.

"Would it surprise you, Ryan, if I told you that this school library didn't get very much respect?" Mrs. Sullivan asked.

"Y-yes?" I said, hoping that was the right answer.

"Then you're an optimist. That's not a bad thing, but not very productive either. No, this library doesn't get much respect. The administration doesn't care about us outside of making sure we've got computers that run the barest minimum to say that they technically run. Outside of scattered donations, we haven't received any major influx of new books in nearly six years, and those we do have are in terrible condition, defaced, destroyed, lost and never to be seen again," Mrs. Sullivan said.

"I'm sorry to hear that, but..." I nervously said. I almost gulped down the last words, not sure I if I should say them, but then I added, "...what does that have to do with me?"

"Let her finish," Marie said sharply.

Mrs. Sullivan put her hand on the younger girl's wrist. "Now, now, Marie, that's not very polite, is it?"

Rocking uncomfortably back and forth on her feet, Marie said, "I'm sorry, Mrs. Sullivan."

There was something strange in the way they looked at each other, an almost silent, animalistic communication passing between them.

"We'll address your interruption later," Mrs. Sullivan said, tersely.

If she knew she was being punished, Marie didn't let it show with the slight smile that crossed her lips, "I understand."

Now, with the year I'd had so far, I would've had to be blind to have missed the tension that was in the air. I didn't quite know exactly what I was seeing, but I could sense something. I didn't know if it was something that might be able to get me out of the trouble I'd found myself in, but it was something that had me hopeful.

Mrs. Sullivan continued, "The greatest disrespect this library receives, though, is what the students do inside of it. They think that just because we've got computers that they can work around our parental filters and watch porn, load our already ancient system with viruses they can't handle. They think because the stacks are dark and private that they can smoke cigarettes, weed or worse, that they can use them for their private liaisons..."

She trailed off, staring me down, letting me stew in what I'd done.

"Ryan, I can't begin to say how deeply disappointed in you I am," Mrs. Sullivan said. "I thought you, of all people, would understand all the hard work I do to make this place into a temple of learning. I never imagined that you would be like the others, disrespecting the library, disrespecting me... like I said, I'm disappointed."

"Mrs. Sullivan, I didn't mean to disappoint you. It just sort of... happened," I said. It was a lame excuse, but it was the truth. Suddenly realizing the depth of the situation, I added, "I really, really don't want to be in trouble, but if I'm going to be, please don't get Josie in trouble too? We only met in here because I was trying to fix a mistake, and-"

Mrs. Sullivan cut me off with a wave. "It's very noble of you to fall on your sword, but that's not where I was going with this."

"It's not? But Marie said-"

"I told Marie to tell you you were in trouble because I knew it would get you in here. While I am upset and disappointed in you for disrespecting my library by messing around with Josie Wong without even being so kind as to ask for my permission, you aren't in trouble. You're quite free to go at any time without any fear of repercussion, but if you decide to stay... we can use this as a learning experience," Mrs. Sullivan purred.

Though by this point I'd relaxed and had a good idea where things were going, it didn't hurt to ask, "What kind of learning experience?"

"The kind of learning experience that begins with you standing up and taking off all of your clothes and letting us get a good look at you, to see if you're all the rumors make you out to be. After that, it might get a little messy, but you're intimately familiar with this particular brand of mess, aren't you?" Mrs. Sullivan said plainly.

I thought it might've been that kind of learning experience, but it was nice having a confirmation. Mrs. Sullivan looked at me with what might've been hunger, while Marie's face was harder to read. I could sense equal parts fascination, skepticism and discomfort on her face, her posture still rigid even as she rocked back and forth on her feet with more urgency. That this might be an opportunity to be with the both of them was a surprising one; I'd been with plenty of girls, a couple older women, and in more threesomes than I could count, but never with an older woman and a girl my age. The prospect was equal parts intimidating and interesting, especially with Mrs. Sullivan effectively a teacher.

I was happy for the opportunity to leave and even happier that I wasn't in any trouble, but did I want to stay? Did I want to see if this was going to get as weird as it felt possible?

If I'd put some serious thought into this I might've found some drawbacks, but the way my cock felt, rock hard and straining to break free from my jeans, I let it do the thinking in this one case.

I took off my shoes and socks and did as I was told, standing before Mrs. Sullivan and Marie. Heart beating faster for a very different reason than it was when I first stepped into the library, I pulled off my shirt.

Mrs. Sullivan raised a hand as if telling me to stop, preventing me from taking off my pants.

Marie was unimpressed. "He's not very muscular."

Mrs. Sullivan approached me, running her fingers lightly over my stomach and up my chest, one of her nails grazing my nipple and making me twitch. She said, "Never let a man's muscles fool you. Many men spend all their time in the gym and for their struggles only cultivate ornamental muscles. They look tasty, and yes, it makes them technically strong, but none of that means they actually have the kind of equipment you'd want, or the understanding of how to use it even if they did."

"I understand," Marie said, even though I wasn't completely sure she did understand the way she looked. She stepped forward, running her own hand briefly down my chest, before stepping away as if having touched a hot stove.

"Don't mind Marie," Mrs. Sullivan, stepping over to her aide. Gently, Mrs. Sullivan ran a hand down Marie's arm before ending cupping Marie's ass. Marie shivered, a soft moan escaping her lips.

Mrs. Sullivan continued, "When she came to me at the beginning of this year, Marie had limited sexual experience but was eager to learn. She came to me for advice about boys, and after a nice, long conversation I was convinced she had great potential. I offered to train her, to teach her to be the kind of slut the other girls wouldn't be able to match. She has proven an eager and proficient student, even if she could use some reminders on when to talk and when to listen."

Marie looked like she wanted to say something, but stopped herself when Mrs. Sullivan pressed on her ass.

"I have enjoyed teaching her, but I lack certain anatomy that would be helpful to complete her training. That, Ryan, is where you come in," Mrs. Sullivan said, looking down at my pants and licking her lips. I never got tired of that look of anticipation; it never ceased making me even harder than I expected possible.

"I've heard rumors of your endowment, but I never believed any of them to be possible until I saw you with Josie Wong. I was impressed. It took a lot of restraint not to push her away and show her how to truly suck a cock, but I had to satisfy myself with retreating to my office and coaxing Marie under my desk, not that she needed much coaxing," Mrs. Sullivan said, squeezing Marie's ass. Marie shivered again, clenching her hands tightly together as if trying to keep herself from touching herself.

"Did you see it, Marie?" Mrs. Sullivan asked.

"No, Mrs. Sullivan," Marie replied.

"And why is that?" Mrs. Sullivan asked.

"Because I wasn't doing my job. I should've been watching. Should've made sure that nobody was doing anything disrespectful in the library," Marie said.

"And you understand that's why I've been punishing you today?" Mrs. Sullivan asked.

"Yes, Mrs. Sullivan," Marie said, again shifting uncomfortably on her feet, though the look of satisfaction on her face told me that she probably liked however she was being punished.

"Now, tell me what you would've done if you'd seen that cock," Mrs. Sullivan said.

A little nervous, Marie cast her eyes down. "I would have touched myself."

"Is that all?"

"I would have touched myself a lot. And then I would've found Mrs. Sullivan so she could touch me, and then so I could touch her. I would have cum a lot," Marie said.

"And?" Mrs. Sullivan said, prompting.

"And..." Marie trailed off. "May I please see your cock, Ryan?"

"Why do you want to see his cock?" Mrs. Sullivan asked.

"I want to see it so I can touch it. I want... I want it in my mouth. I want it in my pussy. I want you to fuck me raw, and I want to fuck you even harder than that. I want your hot cum all over me, in me, everywhere. I want to watch you do all of that to Mrs. Sullivan too. I want the three of us to fill the library with screams while I'm learning to unleash my slutty side," Marie said. Her words came out nervously at first, but the longer she talked the more confident she sounded. It wasn't exactly the best dirty talk I'd received lately (and I'd received a surprising amount) since Marie wasn't quite a skilled seductress, not yet, but it seemed under Mrs. Sullivan's tutelage she was getting there.

"How did she do?" Mrs. Sullivan asked. "And I want an honest assessment, Ryan. Marie is learning and honesty is the best way for her to learn."

Looking to be diplomatic, I said, "It was good. Not perfect, but good. I'd be interested if she would've said that to me out of the library."

Mrs. Sullivan ran a finger along the side of Marie's neck and up under her chin. "Good, but not perfect. It seems we need to practice some more."

"I'm sorry, Mrs. Sullivan, it's just, with..." Marie trailed off.

Mrs. Sullivan sighed. "Very well. We're probably overdue to end your punishment for not catching Ryan and Josie sooner."

Marie smiled brightly, bending over a nearby table. Mrs. Sullivan walked up behind her, caressing Marie's ass, slowly pulling her skirt up and over her pert, tight little ass.

Two things at once surprised me about this view:

First, that Marie wasn't wearing any panties.

Second, that Marie had the end of a butt plug sticking out of her ass.

That would explain why she looked so uncomfortable.

"How long has that been there?" I asked without thinking.

"Since before I had her go looking for you," Mrs. Sullivan said, grabbing the end of the plug and slowly pulling it out of Marie's ass. "And that was quite a while ago."

"He was harder to find than I expected. Why would he have been at the band- OH, FUCK ME!" Marie exclaimed as Mrs. Sullivan pulled a very large butt plug from her ass. Mrs. Sullivan marveled at the sex toy before setting it down on the table next to her polished wooden box.

"Well, you did find him, that is worth some commendation," Mrs. Sullivan said, running a finger down to Marie's pussy and stroking her slightly. Marie whimpered with pleasure, looking back over her shoulder at Mrs. Sullivan and me. Mrs. Sullivan continued, "Of course, you did interrupt me, and I said we would address that."

Mrs. Sullivan took her finger from Marie's pussy and opened up the polished wooden box on the table. I craned my neck and got a good look at a surprisingly comprehensive collection of high end sex toys. Mrs. Sullivan rooted around through them before settling on pulling out a bottle of lube another butt plug and setting it down next to the first, showing it to be significantly larger.

Marie's eyes went wide at the presentation of this new toy, but not from fear. No, that was definitely a face of anticipation.

"Would you like to help with Marie's punishment, Ryan?" Mrs. Sullivan asked, generously pouring some lube on the new plug.

"Sure," I said, walking up behind Marie. For a girl without much of an ass, what she had looked very nice. Tight, fit, the kind of ass that could go for a while. I wanted to touch her, but not wanting to draw Mrs. Sullivan's ire, I didn't. Instead I stared into Marie's eyes as she looked up at me with anticipation. Any sternness she'd once had was now gone, replaced with nothing but primal want. It was a good look on her, one that I knew I'd become accustomed to.