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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, things might get a little unrealistic from time to time, but it’s all in good fun, I swear. This is the first chapter of what I hope to be a long and ongoing series, and as a longtime Literotica fan, my first shot at ever writing anything along these lines, so, please be nice?
If you’d asked me at the beginning of my senior year at Regan Hills High School what I was looking forward to about it most, I’d have told you: the end of it. I know a lot of people like to go on about how high school is some of the best years of our lives, and that we’re supposed to embrace them for all their worth because we’ll miss them when we’re older. I don’t really know how that story started, but I know it’s fucking bullshit. High school is misery and psychological torture masked under the guise of getting an education, and that’s if you’re lucky enough to be popular.
Find yourself a few rungs down on the popularity ladder, and you’re in for a shitshow from day one to graduation.
Find yourself at the bottom of that ladder? Yeah, nice knowing ya.
I spent most of my high school career about a step above that bottom, not quite the most hated kid in school but sure as shit not anyone worth noticing either. Nobody looked to gawky and skinny Ryan Collins with the short brown hair and the glasses as anything more than a low level nerd at best and a piece of background scenery at worst. I had friends to be sure, a mix of similar low-rung outcasts, and I had my share of bullies looking to make my life a living hell, but not as many as some other kids. The one big thing I might’ve been known for wasn’t exactly something I boasted about (more on that later), which left me at a point of near-anonymity that was pretty fine going into senior year.
I was content to let the year just pass on by, keeping my head down and waiting for college to be my time to shine. I was plenty happy to put high school in my rear view mirror and never have to look back.
I probably could’ve pulled it off too, if some higher force didn’t seem to have other plans for me in that first week of school, even if I didn’t fully know it at the time.
“Ryan, can I ask you to stay behind for just a moment?” Mrs. Lynn asked me as class filed out for lunch. There were a few laughs and snickers by my classmates, but most were too focused on lunch to pay me much attention.
My throat lurched. It’d only been a week, not enough time for me to get in trouble, but it’s never fun getting asked to stay behind.
Especially by Mrs. Lynn.
Mrs. Brenda Lynn would’ve been my favorite teacher even if she weren’t the hottest teacher in school, but the fact that she was didn’t hurt matters either. In her mid-thirties and still new enough to teaching that the job hadn’t completely destroyed her yet, she was one of the only teachers I knew who actually understood how exciting history was and found ways of bringing it alive to the class. Beyond that, she was one of the few people who’s been consistently nice to me. I first had her for World History last year, and seeing me down one day, she asked me why, and I was in a mood enough that I broke down and told her about the assholes who’d been harassing me during lunch. Instead of ratting me out or causing a scene, she just opened up her room to me whenever I needed a place to hide away. Lunch with Mrs. Lynn became a regular thing whenever I couldn’t find it with my best friend, Tori, and I think that might’ve been the main thing that helped me survive junior year.
She was compassionate, funny, and smart, and, well, I mentioned ridiculously hot, right?
Yeah, that’s probably the main reason all the boys in school and a fair few girls paid attention to her. With short bobbed blonde hair and a cute face with a pouty-lipped smile that could brighten up any room, her glasses give her a kind of naughty librarian look that’d get you hard on first sight alone. Give her body a look, her large breasts, bubble butt and narrow waist, and you can see why the rumors that she used to be a porn star before she got into teaching.
She wasn’t, for what it’s worth.
Yeah, I’m not gonna claim I was too good to try looking her up. Crushes came easily for me, and the chance that there might be naked pictures of one of them circulating out there I could jack it to was too good to pass up. Finding that there weren’t any, though, didn’t give me the feeling of disappointment I’d anticipated, but rather made me feel guilty. Here I was, trying to find naked pictures of someone I really respected and liked and had helped me out when I was feeling like shit.
It made it hard to look her in the eye, because I could swear it felt like she knew. I don’t know how, but she knew, and outside of an amused smirk, she didn’t say anything.
No, kartal escort I had to be putting too much thought into this. Right?
I waited for the rest of class to file out before walking up to Mrs. Lynn’s desk.
“Yes?” I squeaked.
She laughed. “You’re not in trouble, Ryan. Far from it, actually. I wanted to ask you a favor.”
A favor. Well, that was about the exact opposite of being in trouble.
I could live with that.
“You’re one of the brightest students I’ve ever had, and I’m so happy that you tested into my AP class,” she said.
“Thank you for suggesting it. I’d never really thought of trying out for it, to be honest,” I said.
“Ambition’s not a four-letter-word, Ryan,” she said.
“I know, but, still, I never thought of it. So, thanks for that?”
“You’re welcome. It’ll look great on your college applications. As will this favor I want to ask of you,” she said.
That got my attention. Anything that could help me get as far away from Regan Hills as possible was welcome.
“I’m all ears,” I said.
“Good!” she replied, shuffling through the screen of her tablet. “While I know history and other subjects come easily to you, I’ve more than a few seniors who are… lagging. I know it’s only the first week of school, but there are some people who weren’t doing so well at the end of last year. Some who might be in trouble if these trends continue, and I’d really like to ensure that all my students will graduate with flying colors this year. So, I was wondering… would you be interested in doing some off hours tutoring?”
In truth, no, I really wasn’t interested in doing off hours tutoring. I didn’t like nearly enough of my classmates to want to help most any of them out during school hours, let alone on my own time.
“I’ll write you a really kickass letter of recommendation if you say yes,” she said, setting her tablet down and clasping her hands together pleadingly.
“And if I say no?” I asked, worried by what she wasn’t saying.
“I’d still write you that kickass letter of recommendation, so, this is really more a personal favor than anything else. Please? Pretty please? Pretty please with sugar on top?” she asked, batting her eyes playfully. While I was relieved, it didn’t help my problem.
If this had been any other teacher…
“Okay. I’ll do it,” I said.
“Yay! Thank you, so much. I’ve already got one student lined up. Can I give her your number?”
“Excellent. I’ll twist her arm into getting in touch with you later today,” Mrs. Lynn said, standing up from behind her desk. She closed the distance between us, wrapping me in a friendly and warm hug. It wasn’t the first time Mrs. Lynn hugged me, nor was it the first time the feeling of her large breasts pressed against me made me need to shift my backpack in front of my groin.
“Thank you, again. You’re gonna help a lot of people this year,” she said.
“It’ll, uh, be my pleasure,” I said.
If only I knew how true that was.
Whoever Mrs. Lynn wanted to get in touch with me didn’t call or text by the end of the day, so rather than hang around the library and hope for the best, I rode my bike home and vowed to enjoy the rest of my Friday.
Dad wasn’t home when I got in, not that was much of a surprise. Mom died back when I was in kindergarten (a freak fire at her office), and though the settlement and her life insurance was enough to ensure us a comfortable life in the stereotypical suburbia that was scenic Regan Hills, California, Dad’s never really gotten over it, I think. His industrial sales job worked him hard, too hard, I often think, twelve hour days up to six days a week, trips every other month that have him gone for up to two weeks at a time. He did this because it kept him distracted, and though I didn’t think it was healthy, I loved the guy and let him do what he needed to do. When he was around he was a really great dad, encouraging me and taking me on adventures, but, well, that meant he had to be around.
I got used to his schedule over time, though. Back when I was little, his hours meant I spent a lot of time with our neighbors the Martinezes, but since about fifteen, Dad was fine with me being on my own in the house. I hadn’t burned anything down in the times I was alone, he figured, so why keep bothering the neighbors? Since then, we were basically roommates; I’d learned to cook and keep the place clean while he worked his ass off so we could live this life, and he gave me the space to pursue my own hobbies.
Since those hobbies basically amounted to video games, comics and porn, I’m actually rather glad Dad gave me the space he did. Having to explain those to him felt like more trouble than it was worth.
After I locked my bike up in the garage, I went inside to my room, firing up my computer and pulling a brand new box of tissues from my drawer to keep beside it. While that booted up, I checked my Amazon account on my phone to check kartal escort bayan the status of a package. For my 18th birthday the week before, Dad had given me a small stack of Amazon gift cards and told me to go nuts, and not being the one to turn down that kind of freedom, I went a little nuts on ordering some new Funko figures, graphic novels and new games.
Per what I was seeing, the package was still out for delivery when I got home. I figured I could spend some time at the computer, jerk off a couple times, the package would arrive by the time I was done, I’d load up a game, and kick the weekend off in style.
At least that’s what probably would’ve happened if I hadn’t gotten a new text before I finished checking tracking.
Unknown: Mrs. Lynn says I have to talk to you bout tutoring
“Shit,” I said.
I was hoping this could wait until after the weekend. I could’ve pretended I didn’t see it, gotten back to them the next day and tried to arrange something, but I didn’t want to let Mrs. Lynn down. I texted back.
Me: Who is this?
There were at least three Kaitlyn’s in our class, but there was a sense of dread growing in my stomach that already knew who it was. I had to be sure, though.
Me: Which Kaitlyn?
Unknown: Fuck, Kaitlyn Pruitt, alright? Can we get this over with? Don’t got all day.
Kaitlyn motherfucking Pruitt. It just had to be her.
“Shit,” I repeated.
I’d known Kaitlyn for pretty much my entire life, I think. We went to elementary school, middle school and high school together here in Regan Hills, and for a while there, we might’ve even been friends once. Dad knew her mom from work, and we spent the odds and ends weekends playing together like only little kids whose parents know each other know how. She was pretty and nice and I was pretty awkward, so of course I had a crush on her. The crush lasted until about middle school, at which point my “crush” became more of a “crash and burn.” Being beautiful and personable and making her way through puberty with a lot more grace than the rest of us, she became very popular very fast, and with that popularity, she wasn’t so nice anymore. She became a cheerleader and seemed to embrace every possible cheerleader stereotype possible by being a stuck up bitch who looked down on everybody else.
There was a time once when I thought the old Kaitlyn might still be in there somewhere, but enough of her cold shoulder and public cruelties told me that I shouldn’t get my hopes up for her being much more than a Grade A, raging 18-year-old bitch.
And now, here she is, the first person Mrs. Lynn wants me to tutor.
It’s times like this I think fate’s got a pretty fucking intense sense of humor.
I sighed, trying to figure on a good strategy, and then texted her back.
Me: Okay. I work you in sometime this weekend or early next week maybe. What works for you?
Kaitlyn: Wanna get this over with. I’m at the library now. Where the f are you?
Me: Not at the library.
Kaitlyn: Then get to the library. I wanna get this over with.
Like I missed the first two times she said it. The side of me that wanted to make good with Mrs. Lynn and get this project off to a good start seriously considered leaving for the library.
Then there’s the part of me that remembered it’s Friday, didn’t give two shits about Kaitlyn Pruitt’s schedule, and that I didn’t want my package stolen from the front door as has happened a couple times.
Me: Can’t today. Waitin on a package, can’t leave the house.
Kaitlyn: wtf? I am not gonna wait on this shit. Get over here right tf now!
Typing that felt good, even if it meant I’d catch some fresh hell come Monday. She didn’t type any response for a good long moment, the screen just cycling on the … sign for a while, before she gave one last word.
Yeah, I knew then that Monday was going to be hell, but it was so worth it. Kaitlyn wasn’t the kind of girl who took no easily, and it felt pretty damn awesome to be the one to stick it to her.
For a little while, anyway.
It was about half an hour later when I heard the knock at the front door. Kaitlyn’s texts had put me in a foul mood, foul enough that I didn’t get around to jacking it like I planned, but not foul enough that things couldn’t have been saved with the thought of my package arriving.
“Sweet!” I exclaimed, whooping and pumping my fist because, yeah, I was exactly uncool enough to be whooping and pumping my fist when no one was around.
I ran to the front door and swung it open excitedly.
That excitement left the instant I saw Kaitlyn Pruitt standing there in all her glory.
Now, being a complete and utter bitch didn’t mean I couldn’t tell Kaitlyn was hot, because she was. Despite the perpetual half-sneer and resting bitch face, her face was the narrow kind of beautiful you’d find on a model. Large, deep brown eyes escort kartal above a small pointed nose and pouty lips, silky black hair so straight you’d think it couldn’t be real reaching down to her mid-back. Her skin was soft, unblemished and with just the slightest tan, but it was her body that really shone. When we were growing up together, she was always the scrawniest little thing, but when puberty hit her, it hit her like a ton of bricks. She now rocked what I’d conservatively assume to be a pair of DD tits and a real bubble butt of an ass that was nearly as insane as her boobs.
Standing in the doorway I could see she was dressed to accentuate all of her best assets in tight jeans, a faded pink t-shirt with a wide neck and a bare midriff, and a denim jacket on top that can cover her just enough to make it past the school dress code.
“You really left me out to fucking dry, you know that?” Kaitlyn said, storming past me into the house, dropping her backpack on the floor as she went.
“You’re here,” I said, still trying to wrap my head around what in the actual fuck was happening as I closed and locked the front door.
“Because you weren’t there, and because Mrs. Lynn’s got me backed into a corner enough that I’m here instead of getting ready for Addison fucking Gonzalez’s party,” Kaitlyn complained.
Cry me a fucking river.
This is what I thought. What I said was, “Well, I mean… how-“
“Oh, come on, I used to come here all the time, it’s not like I forgot the way, I’m not stupid,” Kaitlyn said. Her voice dripped with bitchiness, letting me know she wanted to be anywhere but here. All told, I wouldn’t have minded her being far away from here either.
“Except when it comes to history, apparently,” I joked.
Kaitlyn didn’t like my joke very much, but instead of tearing me a new one, she just stormed over to her dropped backpack. Bending over at the waist, she unzipped the pack and rooted around inside. I loved the view and took it in welcomingly, trying to burn it into memory and hoping to use it for jacking fodder later; if Kaitlyn Pruitt was gonna invade my house, I was going to try to get something out of it.
“Mrs. Lynn, that bitch-“
“She’s not a bitch,” I said, defensive.
Grumbling, Kaitlyn said, “No… she isn’t, but when it comes to shit like this? She gave me this paper, said you were supposed to sign it for each of our tutoring sessions to make sure I was attending, and that I was supposed to take a selfie of us together, studying, to prove it, it’s like she doesn’t fucking trust me and thinks I’m gonna cheat.”
I strongly considered pointing out to Kaitlyn that everyone knew she was a notorious cheater, but I figured I’d dug the screws in enough already and didn’t want to press my luck.
“Sounds like she thought that through pretty well,” I admitted.
“Yeah, well, I’m not gonna let it ruin my Friday night, or yours, if you’ll play ball,” Kaitlyn said, getting up and showing me the piece of paper. Mrs. Lynn had printed it up on her own stationary, giving me ten boxes to sign and date for ten tutoring sessions.
“So, you sign this paper right now in all the slots, we both smile for the camera, and I’ll be out of your hair and onto Addison Gonzalez’s shitshow of a party,” Kaitlyn said, forcing a smile that nearly interrupted her resting bitch face. I eyed the paper, seriously tempted to just do it to get her out of my hair.
I didn’t, though.
“No,” I said, screwing up all the courage I had.
“No? Why the fuck not?” Kaitlyn asked.
“Because I made a commitment to do this for Mrs. Lynn, and I’m not going to let her down,” I said.
If there was an answer that would’ve pissed Kaitlyn off more, I don’t know it. “That’s not-“
“Fair?” I interrupted. “No, this is entirely fair. Cheating, like you’re trying to do, that’s not fair.”
She put her hands on her hips. I didn’t know people did that in real life. “If you don’t… I’ll get my boyfriend to kick your ass.”
“You don’t have a boyfriend,” I interjected. “And though I’m sure you can get a boy to kick my ass, that wouldn’t change my position. You honestly think I haven’t had my ass kicked before?”
Truth was, if she did get a guy to kick my ass, I probably would’ve done whatever she wanted me to, but I was hoping it wouldn’t go that far because I really, really didn’t like getting my ass kicked.
Thankfully, she didn’t call my bluff. Instead, she dropped the show of force, all anger leaving her as she looked to me pleadingly. “Come on, Ryan. Please? I’ve got a lot of shit going on, and I can’t afford all the time being tutored.”
Between cheerleading and hanging out with her friends, I was pretty sure she could’ve found some time for her education, but I didn’t say this, because she then jumped in and said, “I’ll… I’ll be nicer to you in school. I’ll get my friends to be nicer to you too.”
As bribes go, this one wasn’t bad. It could’ve made senior year one helluva lot easier, and I was sorely tempted to take her up. She must’ve seen my indecisiveness, because she started rocking back and forth on her feet in anticipation.
Finally, I said, “I’m sorry, but I still… is tutoring really all that bad? So bad you gotta bribe your way out of it?”
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