Senior Year Memories Ch. 15

Having fully lubed the butt plug, Mrs. Sullivan gave it to me. "Until today, the one I pulled from her was the largest she's ever taken. Let's set a new record for her together."

Tentatively, I lined the cone-shaped toy up with Marie's ass, teasing it around her tight little hole. Even though she'd already had a sizable toy in there, you wouldn't know it for the modest resistance I felt. Still, I pushed the plug forward, relishing Marie's sharp intake of breath, the way she gripped the edge of the table slightly, that soft little moan as I pushed it in further.

"More, please," she whispered.

I didn't want to push it in more. What I wanted to do was pull off my pants, whip out my cock and fuck Marie's pussy and ass silly, spraying her down with my cum. The anticipation was killing me, but this new game was too hot not to enjoy. I pressed the plug in further, watching as her asshole stretched obscenely around it, enjoying the way she shuddered more intensely with each fraction of an inch her ass was stretched.

It almost didn't seem like she could take the last flared out portion of the base, it just seemed too wide, but with a yelp and a pop it slid into her ass, only the end of the plug sticking out.

"Very good," Mrs. Sullivan said. "Now, Marie, do you think you've learned your lesson about interrupting?"

"Oh, god yes, Mrs. Sullivan," Marie purred.

"And will you be interrupting me again?" Mrs. Sullivan said.

"Many times," Marie promised.

Mrs. Sullivan shook her head, an amused smile on her face. "Clearly, I've got a lot more to teach."

Clearly I'd underestimated how depraved even the quietest corners of Regan Hills High School were.

Mrs. Sullivan gently grabbed Marie by the hips and coaxed her to stand up. With a plug this large inside of her, Marie was unsteady on her feet, but she followed the librarian's instructions eagerly, first turning around and then dropping to her knees. Looking down at her as she looked up at me hopefully, Marie looked so inviting. If she only moved forward another half a foot, she'd have been able to suck my cock if it were out, but I was sure Mrs. Sullivan staged it this way for a reason.

Mrs. Sullivan walked behind me, pressing her large, sweater-clad breasts against my back. Even through the sweater, I could feel her nipples, hard and thick like bullets pressed against me. Reaching around, Mrs. Sullivan rubbed my cock through my jeans.

"That got you excited, didn't it? Seeing her moaning and shaking like a whore as you pushed that toy into her?" Mrs. Sullivan whispered into my ear.

"I was excited already, but... yes, that was definitely hot," I said.

"Good. Why don't we show Marie how hot you think it is?" Mrs. Sullivan proposed, reaching around to undo my belt, dropping my pants to the floor, then pulling down my underpants to join them. My cock in all of it's ten-inch-long, thick glory, stood out proudly, getting first a sound of approval from Mrs. Sullivan, and Marie's jaw actually dropping open. The precum at the tip was already flowing freely, a small drop of it even dripping slowly off the head in a strand.

"That can't... that can't be real," Marie said, gaping at it.

"Oh, I assure you, it is. Never underestimate a man based on his looks. Some of the most traditionally handsome men you'll find may boast a three inch dick or might not be able to get you off with a map and the best vibrator you'll find, while those you underestimate may have the skills of a sex god or a cock like this," Mrs. Sullivan said, reaching around, slowly, expertly jacking my cock.

I groaned. "I like to think I bring the skills and the cock. I'm... oh man that feels nice... I'm really proud of my abilities to make girls cum."

"And we intend to make use of both," Mrs. Sullivan said. Somehow, she leaned in closer, close enough to completely crush her breasts against her back, letting me know that she was still completely clothed and completely in charge while whispering huskily into my ear. "The thing I love about young guys like you is that you've got stamina to spare and can cum like fountains, and rest assured, I want your stamina and your cum. I want to train Marie, but I want what you've got, and I'm going to get that first, but I want you to last, and if you're going to last, we'll need to drain these balls of yours a little first. There's a lot of ways we could do this, but wouldn't me jacking you off until you drain them all over Marie's pretty little face be the most fun?"

"Yes," I agreed.

Mrs. Sullivan kissed the side of my neck. "Good boy."

To Marie, louder, she said, "Let down your hair and take off your dress, Marie."

Without question, Marie let down her bun, spilling golden locks that fell to her mid-back, then pulled her pretty little floral dress over her head. Her slender body with her B-cup tits, their pretty pink nipples pointed up at me, were a sight to behold. Her pussy had a faint rectangle of blonde hair above it, while her pussy lips, bright pink and engorged as thick as I've ever seen, were completely soaked. Her juices coated her thighs, some even dripping onto the floor.

"Doesn't she look luscious?" Mrs. Sullivan asked, jacking me more forcefully.

"Yes," I admitted. Wearing only her horn-rimmed glasses, knee-high socks and black shoes, Marie was the very definition of luscious.

"You have no idea what this girl is capable of, what I've made her into. I don't think she's aware either, but trust me, today we'll both find out," Mrs. Sullivan whispered to me, punctuating her sentences with kisses to my neck that drove me wild.

"Mrs. Sullivan?" Marie asked.

"Yes?"

"Can I... can I suck him? Please? Pretty please?" Marie asked, her voice full of need.

"No. Right now, you're just going to kneel there and watch," Mrs. Sullivan said. "But if you're good and you share with Ryan the story of why you came to me, you may touch yourself. I think he'll find it quite enjoyable."

"Okay," Marie said begrudgingly, running her hands down her tits, tweaking her nipples before they traveled down to her pussy. Urgently she began to masturbate, the scent of her pussy filling the air. Mrs. Sullivan must have known how long she was liable to last, because she began jacking me more insistently, reaching around with her other hand to fondle my balls.

"I met a guy over the summer," Marie said breathily as she fingerfucked herself. "I thought he was a nice guy, that he liked me, but he wasn't nice, he didn't like me."

"What did he want?" Mrs. Sullivan asked.

"He wanted to fuck me. He wanted me to suck his cock and put his cock in my little cunt. He wasn't a nice guy, but he was nice to me until we got our clothes off. Then he just asked me to suck his cock, which I tried, then lie back in the back seat of his car, which I did. Then he fucked me for less than a minute and came on my thigh, and he took me home. Didn't even make me cum, and didn't ever call me back after that," Marie said, her voice taking on a higher tone as she got closer.

"Sounds like an asshole," I said.

"That was my thought," Mrs. Sullivan agreed.

"When school started, I needed to talk to someone, but I didn't know anyone really. I thought... I thought I'd done something wrong, and that I needed to know what to do so I could be better. I... oh god... I knew I could talk to Mrs. Sullivan, and that she'd give me good advice, but I didn't know what she could show me, what she could teach me, how I wasn't wrong and I could take control of my own sexuality and use it to take charge of my life," Marie said, shaking softly, almost ready to cum. I wasn't far behind joining her with Mrs. Sullivan's skilled hands.

"And you've been such a wonderful student," Mrs. Sullivan said.

"Thank... thank you..." Marie whimpered.

"Are you ready for your reward?" Mrs. Sullivan asked, jacking me even harder, pulling me ever closer and closer to bursting.

"Yes, please, yes, Mrs. Sullivan!" Marie moaned.

"Then cum for me my little slut in training. Cum for me right now and receive your reward," Mrs. Sullivan said, her breath hot against my neck, my cock close to bursting.

"I am, I am, I'M CUMMING! I'M CUUUUUUUUUUUUMMMMMMMMIIIINNNGGGGG!!" Marie wailed.

Her body was wracked by a powerful orgasm as she fingerfucked herself into oblivion, a flood of juices splashing on the floor around her fingers.

"Fuck!" I grunted at the sight as Mrs. Sullivan coaxed my own orgasm free. I hadn't anticipated its power with her talented fingers, but it was hard, the first shot splashing against Marie's face, into her wide open, moaning mouth. Mrs. Sullivan was an expert at aiming, though, making sure the next two massive shots similarly hit her mouth and chin, one glancing off her cheek and hitting her glasses, while several more landed on her tits, cum rolling down her toned stomach, some of it even making it all the way down to her pussy while she still fingerfucked herself.

It felt as if my entire life was being drained through this one orgasm, spread out across Marie's beautiful flesh, but Mrs. Sullivan still kept coaxing, still kept jacking me until the flow began to sputter, the last few drops squeezing out onto her hand.

Once I was completely drained, Mrs. Sullivan stepped out from behind me, licking my cum off of her hand.

"I don't know what lesson you were teaching, but I like it," I admitted.

"A simple, but often hard discovered lesson, that the first time a boy cums will often be the shortest. That sometimes, in order to maximize your enjoyment, you'll need to get him off first, then get him going again for the main event," Mrs. Sullivan said.

"I can do that," Marie said, looking at the cum all over her in awe, running her fingers through it, licking some of them off rapturously.

"That has yet to be seen, but I have faith in you," Mrs. Sullivan said, then turning to me. "You'll want a picture of her, no doubt?"

"If that's okay?" I said.

"Only if you promise you'll touch yourself while looking at it," Marie said.

"That... won't be a problem," I replied.

"Good," Marie said, striking a suitably profane pose, spreading her pussy lips while looking up at me, smiling sweetly and completely covered in cum. I stepped out of my pants, grabbed my camera and a quick picture that promised to be a favorite later.

The moment I put my phone back, Mrs. Sullivan grabbed me by the wrist and pulled me over toward one of the study area's couches.

"Marie, take one of the towels from the box and clean yourself up. I'm going to spend some time getting better acquainted with Ryan. Once you're clean, I expect you to come right over here so we can continue your lessons," Mrs. Sullivan said, getting an approving coo from Marie.

Mrs. Sullivan tossed me onto one of the soft, clean couches and sat down next to me. She was still fully clothed and I was still naked, and right now I wasn't sure she could've been any hotter.

"I'm not your first older woman, am I?" she asked, running a finger under my cock.

"What makes you think that?" I asked, shivering from the contact.

"Most boys your age lose their mind around a woman of my experience the first time, becoming overeager puppies who shoot their wad at the lightest touch. You held out admirably, even under the exquisite ministrations of my hands," she said, inching her short skirt higher, revealing more of her stockinged legs, then her creamy inner thighs, then uncontested proof that Marie wasn't the only one around here who didn't wear panties. A dark patch of hair framed thick, juicy lips and an intoxicating aroma I knew I wanted to become more familiar with.

"Care to show me what your hands are capable of?" Mrs. Sullivan asked.

"With pleasure," I said, reaching between her thighs and running my fingers up and down her wet slit. Mrs. Sullivan groaned approvingly as I explored her folds, applying pressure to her clit with my thumb and running light circles around it.

"Not a bad beginning," she said, undoing the buttons of her sweater one at a time, revealing her body and her massive bra-clad tits to me when she was done. Good lord, they had to be at least an E-cup.

"Wow," I said as she tossed the sweater aside.

"Wow is right," she replied. I kept fingering her, enjoying the sounds she made, the way it made her body writhe with pleasure. Leaning back onto the couch, she rubbed her hands over her body, her hips rocking in time with my fingers.

"Would you like to see my tits?" she asked, rubbing the pronounced bumps through the black fabric of her bra. I nodded. She said, "Then come here."

She pulled me in close, leaning in so we were kissing. Her lips were soft and tender even if her intentions weren't, and we made out on the couch as if we were the only people in the world. To say I'd never fantasized about doing this with Mrs. Sullivan would be a lie, but like many a fantasy I'd had before this year it was something I never thought was actually possible. At this point I should've realized that anything was possible if I put myself in the right position for it, I just had to be on the lookout for those opportunities.

Take Mrs. Sullivan removing her bra for example.

Seeing her giant tits laid bare, the wide pink areola of her nipples, the points almost as long and thick as the first joint of my thumb, was a definite opportunity. So, while I could've continued kissing her delectable lips, I instead leaned down, taking one of those wonderful nipples in my mouth, licking, sucking, nibbling and enjoying her responses. She had very sensitive nipples, which when combined with my fingering her pussy led to some pretty great enjoyable results. Though she hadn't even cum yet, her juices soaked my hand.

I'd gotten lost in sucking on her nipple, so lost I hadn't even noticed that Marie had snuck up on Mrs. Sullivan's other side, sucking on her other available tit. Her eyes locked on mine as we did so, and for how deliciously obscene she looked (even freshly cleaned of my cum), she was so cute. I think she might've even smiled at me as we both continued sucking on Mrs. Sullivan's tits.

I couldn't help myself. I leaned in, kissing Marie around Mrs. Sullivan's nipple. We then broke away, kissing each other. While Mrs. Sullivan's kisses were slow and sensual, Marie's were energetic and passionate, her tongue darting into my mouth, dueling with mine. That I never stopped fingering Mrs. Sullivan through all of this is something of a minor miracle, I think.

"Alright, that's enough of that, for now," Mrs. Sullivan said, breaking us apart. She got up from the couch, guided Marie away and leaned me down flat on my back.

"Are you ready for two lessons at once?" Mrs. Sullivan asked.

"Definitely," Marie replied.

"Good," Mrs. Sullivan said, not giving me much time to wonder what two lessons might entail before she pulled up her skirt, straddled my head and sat on my face. Far from the first time a woman sat on my face, I knew to get to work, discovering with my mouth that her pussy was every bit as juicy as my fingers discovered. I devoured her voraciously, loving her flavor and to lick up every drop I could. Considering the way she was flowing, that task meant I'd likely be licking her for a while.

"First lesson, oh, yeah, right there Ryan, good boy... god, your first lesson, Marie, is to ensure your pleasure. While Ryan here is no doubt, mmmm, fuck that's nice, while Ryan's no doubt a very considerate lover, and is very, very good at eating pussy, you won't always guarantee every man you're with is that way on his own. Only go with a man who promises pleasure, but make sure he holds to that promise, make sure he makes you cum at least once before you allow him inside you. Penetrative sex alone is never a guarantee for an orgasm, and you don't want him saying he's 'too worn out' to attend to your pleasure after he's filled you with cum," Mrs. Sullivan said.

"I understand, Mrs. Sullivan, thank you," Marie said. From the sounds I heard, I was pretty sure that Marie was attending to her own needs quite efficiently with a vibrator right now. "And what is my second lesson?"

"I could bend over right now and take Ryan in a 69," Mrs. Sullivan boasted. "But... ooh, that's a nice spot, Ryan, put that tongue in deeper. Deeper, I said! Yeah, like that. He liked it when I talked about sucking his cock, but that would rob you of a valuable learning experience. I've seen you take strapons nearly this big, but are you prepared to deepthroat this giant fucking cock?"

"I thought you'd never ask," Marie said confidently, and though I couldn't see it, I felt wet warmth envelop my cock as Marie took me in her mouth. For a girl with as limited experience as she had, she did an amazing job, taking almost half my length in one bob before opening her throat up and forcing the rest of me down. The tightness was insane, and if I weren't at full hardness before, I'm sure I got that way in Marie's throat. She bobbed up and down, coached on rhythm and technique by Mrs. Sullivan the entire way.

"Mmm, you're both doing such a good job, such a good job, that's a nice fucking blowjob, keep going on him like that, but not too hard, no, can't have him cumming, can't make him cum, not until we've fucked properly, not until, oh god, so close, keep going Ryan, right there, keep eating, keep licking, keep doing whatever you're doing, right there, right there, RIGHT FUCKING THERE, FUCK, I'M CUMMING, I'M CUMMING!!"

A flood of juices filled my mouth and covered my face as Mrs. Sullivan came, her body writhing above me as she was jolted and rocked by the heavy orgasm. I'd have loved to have joined her and filled Marie's sweet, talented mouth with my cum, but I wasn't that close yet, and something told me Mrs. Sullivan wouldn't have been all that happy with me anyway.

She said she wanted me first, and I didn't want to disappoint.

"That's enough for now, Marie, you've done well," Mrs. Sullivan said, climbing off of me. I don't know which sight was more beautiful, seeing Marie's mouth stretched around my cock or looking up at Mrs. Sullivan through the valley of her massive tits, flush from her orgasm, her face a mask of pure satisfaction.

Marie let my cock plop free from her mouth. "Thank you, Mrs. Sullivan."

Mrs. Sullivan guided me off the couch, and with my cock as hard as it was she could've asked me to do pretty much anything at this point and I'd have said yes. That she pulled up her skirt and laid down on her back the couch was a good start. That she looked up at me with the most unexpectedly perfect "come fuck me" eyes was another. Looking so perfect with her tits spread out and her long, stocking-clad legs spread for me invitingly, I honestly couldn't tell you what I was waiting for.

I realized what that was when she said, "I'm not going to mince my words. I want you to fuck me, Ryan, and I want you to watch us while you fuck yourself silly with that vibrator, alright Marie?"

"Yes, Mrs. Sullivan," Marie said.

"And Marie?"

"Yes?"

"Take the plug out," Mrs. Sullivan commanded.

"Why? Have I been suitably punished?"

"Not yet, but we can address that later. I want you to take it out now, the reasons why will become apparent when it's your turn with Ryan," Mrs. Sullivan said.

I'm not entirely sure if there were words hidden in Marie's squeal of glee (though it sounded like there might've been), but there were definitely words in her moan as she removed the butt plug.

"Oh, FUCK!"

Marie could've been screaming about a coming stampede for all I cared at the moment, all I knew was that I was standing over Mrs. Sullivan and she wanted me to fuck her. Though it was awkward climbing on top of her on the couch, she was able to wrap her legs around me as I lined my cock up with her pussy lips.

"Do it. Push inside. Fuck me like you've always wanted to," she moaned.