Usual disclaimer time: even though this story takes place almost entirely in a high school setting, all of the characters in this story are 18 years of age or older, and since we live in the big and wonderful world of porn, things can get a little too realistic at times, but I swear it’s all in good fun. This is the first chapter of what I hope will be a long and ongoing series, and as a longtime Literotica fan, this is my first attempt at writing anything along these lines, so please be kind?
*****
If you had asked me at the beginning of my senior year at Reagan Hills High School what I was most looking forward to, I would have told you: the end. I know a lot of people like to talk about how high school is the best time of our lives and that we should embrace it with all its values because we’ll miss it when we’re older. I don’t really know how that story started, but I know it’s complete bullshit. High school is traumatic and psychological torture under the guise of an education, if you’re lucky enough to be in it.
If you find yourself a few rungs behind on the popularity ladder, you will suffer from poor performance from day one until graduation.
Do you find yourself at the bottom of the ladder? Yes, nice to meet you.
I spent most of my high school career a step above that low level, I wasn’t the most annoying kid in school, but definitely not someone anyone would pay attention to. No one would have thought that the short brown haired, bespectacled, dumb and skinny Ryan Collins was a low level nerd at best and just a background scene at worst. Sure, I had friends who were just as low-grade outcasts, and I had my share of bullies who wanted to make my life hell, but not as much as the other kids. I may be famous for a big thing, but it’s not something I brag about (more on that later), which leaves me in a state of anonymity, which isn’t bad in my senior year.
I was content to let the year go by, keeping my head down, waiting for my time to shine in college. I’m happy to put high school in my rearview mirror and never have to look back.
If some higher power didn’t have some other plan for me during the first week of school, I might have succeeded, even if I wasn’t fully aware of it at the time.
***
“Ryan, can I ask you to wait a moment?” Mrs. Lin asked me as my classmates headed out for lunch. There were a few snickers from my classmates, but most were focused on lunch and didn’t pay much attention to me.
I choked up. It’s only been a week, not long enough to get me into trouble, but being told to stop is never fun.
Especially Mrs. Lynn.
Mrs. Brenda Lynn would have been my favorite teacher even if she wasn’t the sexiest teacher in school, but the fact that she didn’t hurt is a shame. She’s in her thirties and new to teaching, the job hasn’t completely destroyed her yet, and she’s one of the only teachers I know who really understands how exciting history can be and has found a way to bring it to life in a way that can be brought to the classroom. Also, she’s one of the few people who has always been nice to me. She was with me in my first World History class last year and one day she saw me feeling sad and asked me why, I was in a bad mood and I cried and told her about the idiots who bothered me at lunch. Whenever I needed a place to hide, she would open her room to me without chiding me or getting into an argument. Lunch with Mrs. Lynn became a regular thing whenever I couldn’t have lunch with my best friend Tori, and I think that was probably the main thing that helped me carry me through my junior year.
She’s kind, funny, smart and, did I mention she’s super sexy, right?
Yes, that was probably the main reason why all the boys and quite a few girls in school paid attention to her. She has short blonde hair, a cute face and a smile that can light up any room. Her glasses give her a naughty librarian look that is hard to understand at first glance. Take a look at her body, big breasts, bubble butt and tiny waist, and you will understand why she was rumored to be a porn star before she became a teacher.
Anyway, he isn’t.
Yeah, I wouldn’t say I’m great at trying to find someone. It’s easy for me to have a crush, and the possibility that a nude picture of one of them would be out there and I could grab them was an opportunity not to be missed. However, instead of the disappointment I was expecting, I felt guilty for not finding anyone. I’m here trying to find nude pictures of people I really respect and like and to help me when I’m feeling bad.
It became hard for me to look into her eyes because I could swear it seemed like she knew. I don’t know how she knew, but she just smiled and said nothing.
No, I might be thinking too much about this. Right?
I waited until the rest of the class was out before going to Teacher Lynn’s desk.
“Yes?” I shouted.
She laughed. “You’re not in trouble, Ryan. In fact, far from it. I have to ask you a favor.”
Ahsan. Well, it’s the exact opposite of being stuck.
I can live with that.
“Yes?”
She said, “You are one of the most intelligent students I have ever met and I am so glad you came to my AP class.”
“Thanks for the advice. To be honest, I never thought of trying it,” I said.
“Ryan, ambition isn’t a four-letter word,” she said.
“I know, but, I still haven’t thought about it. So, thanks?”
“You’re welcome. This will look great on your college applications. I want to ask you a favor,” she said.
This caught my attention. Anything that can help me get as far away from Mount Legion as possible is welcome.
“I’m all ears,” I said.
“Okay!” she replied, scrolling on the tablet screen. “Although I know that history and other subjects are easy for you, I have some seniors… who are falling behind. I know it’s only the first week of school, but some didn’t do so well at the end of last year, if these trends continue, some may be in trouble, and I really want to make sure that all of my students graduate with honors this year?”
Actually, no, I have no interest in tutoring in my free time. I didn’t really like my classmates and didn’t want to help most of them during class time, let alone during my own time.
“If you say yes, I’ll write you a wonderful letter of recommendation,” she said, holding down the tablet and folding her hands pleadingly.
“What if I say no?” I asked, worried about what she hadn’t said.
“I’m still going to write you that wonderful recommendation letter, so this is really more of a personal favor than anything else. Please? Very please? Please put some sugar in it?” she asked playfully. Although I was relieved, it didn’t help my problem.
If this were any other teacher…
“Okay. I’ll do it,” I said.
“Yes! Thank you very much. I already have a student in line. Can I give her your phone number?”
“Definitely.”
“Great. I’ll give him a hand to contact you later today,” Mrs. Lin said as she stood up from behind her desk. She closed the distance between us and gave me a friendly, warm hug. This wasn’t the first time Mrs. Lin had hugged me, nor was it the first time I had to shift my backpack to the front of my waist because of the pressure her large breasts felt on me.
“Thank you again. You’re going to help a lot of people this year,” she said.
“Well, it’s my pleasure,” I said.
I wish I knew how true that was.
***
The person Mrs. Lynn wanted me to contact hadn’t called or texted by the end of the day, so instead of hanging out at the library and hoping for the best, I rode my bike home, vowing to enjoy what little time I had left.
Dad wasn’t home when I moved in, which wasn’t surprising. Mom died when I was in kindergarten (in a massive fire in her office), and although the settlement and her life insurance were enough to ensure we could live a comfortable life in the conservative suburb of beautiful Mount Reagan, California, Dad never really recovered from it, I guess. I often thought his job in industrial sales was pretty tough, working twelve hours a day, six days a week, and traveling for two weeks at a time every other month. He does it because it distracts him, and although I don’t think it’s healthy, I love the guy and let him do what he needs to do. He’s a really great dad when he’s around, encouraging me and taking me on adventures, but, well, that means he has to be around.
But over time I got used to his schedule. When I was younger, his work hours meant I spent a lot of time with my neighbor Martinez, but from about age fifteen, Dad allowed me to stay home alone. He thought, I didn’t burn anything when I was alone, so why bother the neighbors? From then on, we were basically roommates; I learned to cook and keep the place clean while he did all the hard work so we could have a life where he gave me space to pursue my hobbies.
Since those hobbies were basically video games, comics, and porn, I’m really glad my dad gave me the space he had. Explaining these things to him felt like more trouble than good.
After locking my bike in the garage, I went into my room, turned on my computer, and pulled a fresh box of tissues out of the drawer and put it next to me. When it started, I checked my Amazon account on my phone to check the status of packages. For my 18th birthday the other week, my dad gave me a small stack of Amazon gift cards and told me to go crazy, but I wouldn’t turn down freedom, so I went a little crazy and ordered some new Funko dolls, graphic novels, and new games.
From what I saw, the package was still waiting for delivery when I got home. I thought I would spend some time in front of the computer, masturbate a few times, and by the time I was done, the package would arrive, I would load up a game and have a great start to the weekend.
At least, that’s what might happen if I don’t get a new text message before I finish checking the track.
Unknown: Mrs. Lin said I need to talk to you about counseling.
“Hey,” I said.
I expected it might have to wait until after the weekend. I could have pretended not to have seen it and contacted them the next day and tried to arrange something, but I didn’t want to disappoint Mrs. Lin. I messaged back.
Me: Who is this?
UNIDENTIFIED: Caitlin.
There were at least three Caitlins in our class, but I had a sneaking feeling I already knew which one she was. But I had to be sure.
Me: Which Caitlin?
Unknown: Fuck off, Caitlin Pruitt, okay? Can we get rid of this? Don’t have time all day
Fucking Caitlin Pruitt. It must be her.
“Fuck you,” I repeated.
I think I’ve known Caitlin almost my whole life. We went to elementary school, junior high, and high school together at Mount Legion, and for a while we may have even been friends. Dad met her mom while at work and we played together on the weekends, like kids whose parents know each other. She was pretty and nice and I was awkward, so of course I liked her. This obsession lasted until about middle school, when my “obsession” became more of a “crash and burn.” Pretty and charming, and living out her teen years more modestly than the rest of us, she quickly became popular, and with that popularity came a less sociable person. She becomes a cheerleader and begins to embody every possible cheerleader stereotype, becoming a smug bitch who despises everyone else.
There was a time when I thought the old Caitlin might still be in there somewhere, but her cold shoulder and open cruelty told me I shouldn’t expect anything more from her than a grade-A, angry 18-year-old bitch.
Now, here she is, the first person Mrs. Lin has asked me to teach.
In moments like these, I think fate has a very strong sense of humor.
I sighed, tried to think of a good strategy, and messaged her back.
I’m fine. I’ll probably work for you later this week or early next week. What works for you?
Caitlin: Want to finish this. I’m in the library right now. Where are you?
Me: Not in the library.
Caitlin: Then go to the library. I want to finish this.
Like I had missed saying this the first two times. Part of me wanted to compromise with Mrs. Lynn and get this project off to a good start, but I seriously considered going to the library.
Then, I remembered it was a Friday, I didn’t care about Caitlin Pruitt’s schedule, and I didn’t want my package stolen at the front door, as had happened so many times.
Me: Not today. Can’t go out waiting for the package.
I’m sorry.
Caitlin: What? I’m not going to wait for this nonsense. Come here now!
Not me
It feels good to type this, even if it means I’ll have to face some fresh hell on Monday. She didn’t type a reply for a long time, the screen kept spinning on the prompt for a while, and then she said her last words.
Caitlin: Asshole
Yes, I knew then that Monday was going to be hell, but it was worth it. Kaitlyn is not a girl who takes things easy, and it feels great to keep up with her.
For a while, anyway.
***
About half an hour later I heard a knock on the front door. Caitlin’s text message put me in a bad mood, bad enough that I didn’t have time to pick it up as planned, but not so bad that nothing could be saved until my package arrived.
“Sweetie!” I yelled, balling my fists because, yes, I was stupid enough to yell and ball my fists when no one else was around.
I ran to the front door and threw it open excitedly.
That excitement vanished when I saw Caitlin Pruitt standing there in all her glory.
Now, being a total bitch doesn’t mean I can’t see Caitlin being hot, because she is hot. Her face, despite her eternal half-sneer and resting bitch face, had the narrow beauty of a model. Big dark brown eyes, pointed little nose and pouty lips, and silky black hair so straight you’d think it couldn’t actually hang down to the middle of her back. Her skin was soft, blemish-free and only the slightest stain of a tan, but it was her body that really glowed. She was always the prettiest kid when we were growing up together, but when puberty hit her it hit her like a ton of bricks. She was now rocking what I traditionally think of as a pair of DD tits and a real bubble butt that was almost as insane as her tits.
Standing at the door, I could see that she was wearing tight jeans, a pale pink top with a wide collar, and a denim jacket that highlighted all her best features.
“You actually left him behind, did you know that?” Caitlin said, running into the house past me, dropping her bag on the floor as she went.
“You’re here,” I said and closed the front door, still trying to work out in my mind what was going on.
“Because you weren’t there and Mrs. Lynn backed me into a corner, that’s why I’m here instead of getting fucked by Addison at Gonzalez’s party,” Kaitlyn complained.
Make me cry like a river.
That’s my idea. I said, “Well, I mean…how-“
“Oh, come on, I’ve been here all the time, it’s not like I’ve lost my way, and I’m not stupid,” Caitlin said. There was enough venom in her voice that I knew she wanted to be anywhere but here. All in all, I don’t mind if it’s far away.
“Except for the history, of course,” I joked.
Caitlin didn’t really like my joke, but instead of tearing a new one for me, she scurried to her dropped backpack. She bent down, opened her bag and started rummaging around inside. I loved this scene so much, I embraced it happily, tried to burn it into my memory, and hoped to use it later to fish for bait; if Caitlin Pruitt invaded my home, I would try to get something out of it;
“Mrs. Lin, that bitch—”
“She’s not a bitch,” I argued.
Kaitlyn mumbled, “No… she’s not, but talking about this nonsense? She gave me this piece of paper and said you must sign every coaching session, we have to make sure I attend, and there has to be a selfie of us studying together to prove it, like she doesn’t trust me and thinks I’m going to cheat.
I strongly considered telling Caitlin that everyone knew she was a notorious liar, but I figured I’d screwed up enough and didn’t want to push my luck anymore.
“It seems like she’s thinking clearly,” I admitted.
“Yeah, well, I’m not going to let it ruin my Friday night or your Friday night if you want,” Caitlin said, standing up and showing me the paper. Mrs. Lynn printed it out on her letterhead and gave me ten boxes to sign and date for ten coaching sessions.
“So now you sign all the open spaces on this document, we’ll all smile for the camera, and then I’ll get out of your hair and go to one of Edison Gonzalez’s parties,” Caitlin said, her face filled with a happy, bitch-like face that almost interrupted her sentence punctuation. I looked at the newspaper and wished I could spare her from her worries by doing so.
but I do not have.
“No,” I said, mustering all my courage.
“No? Why not?” Caitlin asked.
“Because I promised to do this for Mrs. Lin, and I won’t let her down,” I said.
If there is an answer that will make Caitlin angrier, I don’t know. “Which is not–“
“Fair?” I interrupted. “No, it’s perfectly fair. Fraud, as you’re trying to do, is 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 have my boyfriend fuck your ass.”
“You don’t have a boyfriend,” I interjected. “Although I’m sure you could get a guy to kick my ass, it wouldn’t change my stance. Do you really think I’ve never gotten my ass kicked before?”
Truth is, if she let some guy fuck my ass I probably would have done what she wanted me to do, but I hope it wouldn’t go that far because I really don’t like getting my ass fucked.
Thankfully, he didn’t call my bluff. Instead, he dropped the show of force and all anger vanished as he looked at me pleadingly. “Come on, Ryan. Please? I have so much to do and I can’t be teaching all the time.”
Between cheerleading and hanging out with her friends, I’m sure she could find some time to get an education, but I said no because she then spoke up and said, “I will.. I will. If you are good at school, I will tell my friends to be good to you too.”
As far as bribes go, it’s not a bad one. It would have made the first year of high school a lot easier and I wanted to take her very seriously. She must have noticed my hesitation because she started rocking back and forth in anticipation.
Finally, I said, “I’m sorry, but I still…is counseling really that bad? So bad that you have to bribe your way out of it?”
