by Anthology
I pick up the pace, grinding myself in deeper—harder—and I know there’s no way either of us will last long. Our bodies are too damn perfect for one another’s for more than five minutes of this. So I close my eyes and soak in every moment I can.
“Simon,” she whispers.
My pace is vigorous, and I barely hear her. My tongue is circling her areola, and when I hear the echo of her voice, my thrust quickens even more as I trap her small nipple between my teeth, feeling it pucker.
I’m so damn close—within seconds of coming. I feel the orgasm build as waves of euphoria encompass me.
“Simon?”
“Holy shit,” I sputter, unable to tame it any longer. She grips my hair harder, my thrusts become fiercer, and I lose any semblance of control as I pound into her, reveling as the last of the orgasm rips through. I grind my body against hers and I come quietly, yet crudely.
“Simon? You in there?” I hear the voice again along with a knock at my door. My heart races wildly as I open my eyes up and reach for the towel on the floor.
“Yeah, Ma. I’m here. I’m…resting,” I manage to choke out, feeling hot and flustered.
“Okay, I’ll leave you alone. We just got home and we’re going to go to bed,” Mom says quietly through the door.
I swallow. “Okay. Goodnight.” I clean myself off and throw the towel on my nightstand, knocking over the bottle of lotion, which makes me roll my eyes.
After putting my boxers back on, I climb into my empty bed and close my laptop, still feeling frustrated.
I don’t know how much longer this fantasy of my teacher will suffice. I want her so desperately sometimes that I wonder if my dick will explode if I don’t feel her wrapped around it soon.
I turn on to my side and close my eyes, thinking of her gorgeous face when I’ll see her at debate next week.
Chapter Two
I wake the next morning and hear the clattering of pots and pans in the kitchen. After a piss and quick stretch, I head straight for my desk and pull up my password-protected Excel sheets: my babies. I have an Excel spreadsheet for just about everything in my life.
The first document is a schedule of all the girls that I’ve said I’d keep in contact with after I’ve fooled around with them—cell phone numbers and addresses. I’ve also charted the dates, locations, and certain things they enjoyed: If she was a soft touch kind of girl. Did she expect sweet nothings whispered in her ear afterwards? Did she like it rough and hard? And could I get away with wiping my dick on her skirt and leaving without saying a word?
I set the alarm on my phone with a message with each girl’s name—as a reminder to text them at certain times for the next week—and stare at Andrea’s name.
She brought the total count to nine last week. Nine notches of sexual exploration. The ninth girl I’ve charmed, seduced, screwed, and promised to call the next day.
Glancing back up at my computer screen, I look at each of the names, then stop when I get to the bottom.
Andrea is what I categorize as the Volkswagen.
It’s not as bad as you think.
I first got the idea for categorizing girls based on cars a little over a year ago. For this category, its purpose is to say she’s efficient, but exotic in her own right. Not quite like the Ford—which will be explained later—Volkswagen means "people's car" in German. She’s sweet, has a lot of friends, and you’d never predict the kind of smooth and easy ride she gives just by looking at her.
Each girl is then categorized even further into a specific model—in this case, Andrea started out the evening as the Beetle—but by the time the night ended, she was a shiny new Passat.
Then there is the girl that every guy wants to be with and every girl wants to be. She’s the Jaguar. You know—the sleek, trim, beautiful model that’s all about showing off to your friends. It’s the ride you’ve dreamed about your entire life; you know it’ll be smooth, unforgettable, and unattainable.
Miss Shields is what I consider my Jaguar.
Not only after the animal—an animal who has a strong bite, does the majority of its hunting around dawn and dusk, and is more than likely to stalk-and-ambush its prey rather than chase it—but also after the original 1922 slogan of the British sports car: “Grace, Space, Pace.” The Jaguar is the kind of woman you don’t rush, unless it’s on her terms. She’s at the top of her food chain. And she’s the kind of woman you want to pamper and polish.
I’ve had sex nine times in my life—with nine unique and perfectly attractive girls. Not bad, considering I’m a senior in high school and just turned eighteen.
Now I’m looking for one more.
The mythical ten.
I decided a long time ago that ten was my magic number. Why? Ten is when I can say I’m experienced. When my sexual conquests hit double digits, I can feel confident enough to get Miss Shields.
I just need one more—one more willing participant in this game of the flesh—and then I can say I’m man enough to have her. Worthy enough. Because she’s the kind of woman that would expect only the best.
My body still buzzes from last night’s fantasy, and it hums from her imaginary touch. One day I’d capture my Jaguar.
The memory of our first encounter still lingers in my mind after all this time.
It was during a party over the summer between my sophomore and junior years of high school.
My parents were rich, so that afforded me a certain kind of status at my school. But I wasn’t a jock. And I wasn’t the fucking prom king. But in my own small world of geeks and outcasts, I was king. And the chicks ate my I’m-too-cool-to-hang-with-the-popular-crowd attitude with a fucking spoon.
That night at the party I’d stayed outside by the pool in the backyard most of the night, alone. Kids would come and go, and I could hear the laughter and music coming from inside the house, but I never ventured back in.
It wasn’t until about eleven o’clock that I questioned my presence there at all, and made my way around the house to get to my car.
And there she stood.
Miss Shields.
Well, she wasn’t exactly standing. She had just stepped out of a taxi and was attempting to walk into her house next door. But she kept stumbling and sobbing. After the taxi drove away, I found myself walking toward the weeping but sexy woman. She had fallen to her knees, and something about her had me reaching out and helping her up. And yeah, I couldn’t help but notice her pink panties underneath her skirt—something that gave my dick a five-alarm jerk alert—but I covered her up to give her some dignity. Then I helped her into the house and onto her couch.
She never did tell me why she’d been crying, but she didn’t need to tell me she’d been drinking. It was obvious. But after I served her a glass of water and she changed into a T-shirt and sweatpants, she was able to speak.
I had no idea who she was until she informed me that she was an English teacher at my school and she coached the debate team.
We talked well into the night. She listened to what I had to say. She acknowledged me. Now, the recollection is hazy and I can barely remember what we spoke about, but I had such a connection with her that night—so much more of one than I’d ever had with anyone. I fantasized about all the things we’d do, and all the places I’d take her. I even indulged in the thought of taking her to my getaway in the woods.
She even gave me a hug when I was about to leave. Physical contact, even of the nonsexual variety, from a hot woman was all I needed to indulge in a marathon tug-fest later.
You see, Miss Shields—in all of her vulnerable, hot teacher glory—had given me a glimpse of that seemingly unattainable goal that I wanted so badly I could taste it.
Because I, Simon Blackwell, III, was hot for my teacher, and I was going to seduce her right out of her skimpy, too-sexy-for-her-own-good panties if it was the last thing I did.
Everyone has that moment of definition, when the clarity of who you want to be is so vivid in your mind that you can’t turn bac
k once you’ve caught that glimpse. A goal that you see and then seek: it’s the moment you decide your future.
This was that moment for me.
Miss Shields was my Jaguar, and I planned to have one hell of a ride.
Chapter Three
Number Nine: The Volkswagen
September 2, 2014 (Two weeks ago)
Andrea, the Volkswagen, tugged at her bottom lip and uncrossed her legs, leaning toward me. Tilting her head, she reached back, taking down her dark ponytail.
She gave me a look—a look I’d grown familiar with in the past twelve months: she was going to let me kiss her.
I hadn’t quite figured out the third base signal yet. It seems to vary from girl to girl; I may need to start a spreadsheet on it. At our age they’re still shy, insecure, and aren’t experienced enough to know how to give guys like me the go-ahead. Most guys my age need a written invitation as their ‘sign,’ but I’ve been learning to pick up the subtleties.
I’m determined.
My eyes traveled down to the neckline of her shirt. She was hiding everything with her baggy sweater and tight jeans, but her eyes were giving her away. I briefly thought about what shade of pink her nipples were.
“What were we talking about?” she asked quietly, flirtatiously sweeping her hand through her hair.
I gave her my signature move—the one that I’ve heard most of the girls on the debate team giggle and whisper about—and slid off my glasses. She bit her quivering bottom lip. She must have heard the rumors that once I’ve done this, I had every intention of going as far as she’d let me.
I flashed a cocky smile and set them on my nightstand. My eyes flickered over to the doorknob to make sure the lock was set. Even though my parents weren’t due home for another week, I was still paranoid.
The flush that started at Andrea’s neck had moved to her cheeks, and her breathing shifted. She was easier to read than I thought she’d be. Or maybe I was getting better at recognizing the signs.
You know, the signs—the ones that let you know you’re about to tap that ass.
I closed the books on my bed and leaned down in front of her to set them on the floor. She gasped, thinking I was about to make a move, but my intentions were to prolong it as much as possible. In my experience with girls, the more I delayed the act, the quicker they came.
I sat back on the bed and patted the spot next to me in invitation. She swallowed loudly and nodded, her eyes wide with anticipation. Quickly rising from her chair, she moved to the space next to me and folded her hands over her lap, fidgeting with her thumbs.
“We were talking about uniforms,” I whispered, trying not to grin at Andrea’s obvious nervousness. It was such an ego boost knowing I got to a chick like that. “School uniforms.”
“Right!” she chirped, keeping her eyes away from mine. She shook her head and gained composure. “I don’t think I could wear a uniform every day. We have so many rules and restrictions that I don’t think I could handle the school telling me what I should wear too,” she added quietly, keeping her head down.
I lifted her chin so she was forced to make eye contact with me. “That’s good.” I smiled. “It’s a good start.” I grazed my thumb over her cheek and could already see my fly coming undone in the reflection of her hazel eyes.
I leaned into her and she stopped breathing altogether.
I smiled and swept her hair behind her ear so I could whisper into it—low and husky and with just the right amount of suggestiveness.
“But I’d like to see you in one of those skirts every day.” My hand moved down to her thigh and I grazed her inseam with two fingers, so that she was barely able to feel it. Her eyes pleaded with me to kiss her, and I grinned.
Yep, Andrea was definitely a Volkswagen: Reliable. Dependable. And oh so easy.
“You’re so smart, Simon. And you’re one of the most popular guys at school. All the girls want you. And you’re like…really hot,” she said a little breathlessly, closing her eyes, her cheeks burning with embarrassment by her admission.
I admit it all seemed like poorly filmed porn. The dialogue couldn’t get any worse. But it’s not like either of us were there for the quality of the conversation.
Okay, so maybe she was.
I chuckled. “Open your eyes.”
She exhaled. “I’m sorry. This is all a little surreal right now. And I’m really freaking nervous,” she added.
She needed reassurance. She needed to know that I was in the moment with her and that I would acknowledge her at school on Monday. Whether or not that was true—or if I’d even remember her name—was beside the point. She needed that cozy little blanket of knowing that I wasn’t using her.
Piece of cake. There was a reason I took Introduction to Performing Arts last semester.
“Do you have any idea how long I’ve wanted this moment?” I began, finding one of my go-to speeches I had prepared. “I’ve been watching you for weeks and hoping that Miss Shields would pair us up so that we could be alone. I’m just as nervous as you are right now. So whatever you’ve heard about me or think of my reputation, I can assure you: I don’t do this all the time.” I took her hand and placed it on my chest.
I looked down and scratched the back of my head, hoping she’d pick it up as nervousness.
Her swoon was how I knew I had her wrapped around my pinkie.
“This moment is as surreal for me as it is for you,” I added, taking her hand again and rubbing her knuckles.
“Oh, Simon,” she said, leaning in to kiss me.
I quickly closed my eyes and thought of Miss Shields. If she were Katie Shields, how would I react? What would she want me to do next? She’d be used to a more experienced man, one that wasn’t so eager.
This is what every girl in the past three years has been for me: practice. In every scenario I’ve been in, every sexual, kinky, or intimate moment in which I’ve partaken, I get to this point and close my eyes.
Katie Shields is waiting for me.
It’s always Miss Shields.
Chapter Four
There are a few things I am good at. School is one. Dropping panties is another. And arguing my ass off on the debate team is also at the top of the list.
But my passion is the debate coach.
It’s been three weeks since I turned eighteen. And every minute of it has played tug-of-war with my conscience. Turning eighteen has shone a whole new light on the potential I have with Miss Shields…I mean Katie. This is my senior year: my last year with her. My last chance to make something—anything—happen. And now that I’m eighteen, she doesn’t need to fight the attraction I know she feels toward me.
Because I’m legal.
Sweet, blissful, 100 percent okay to have sex with an older, sexier-than-any-high-school-girl, woman.
I just need to make sure I know what I’m doing when I finally decide to make a move. So all of these notches on my belt were essential.
If a fairy godmother or a genie in a lamp would’ve granted me one wish at the beginning of this school year, it would have been a total no-brainer: I would’ve wished for Miss Shields. I wanted every breath from her full lips, every dark strand of hair on her head, and all thirty-three inches of her inseam.
Miss Shields—or Katie, as I like to refer to her—isn’t like the adolescent females in my school. She doesn’t spend hours texting, posting, or pinning. She doesn’t bother with selfies or applying a fresh coat of lip gloss between classes. And you can bet your ass that all of her status updates use correct grammar.
Mmmm…correct grammar usage will get me every time.
Oh yes, Miss Shields is different all right. She has style and grace. She wears clothes that cover just enough skin to get my imagination going. Her long black hair falls to her waist, but no one knows this since she always keeps it up in a bun. And she wears stockings. Every. Day. The kind that stop at the thigh and have an inch or two of elastic lace holding them up.
Ah, the stockings. They pro
vided plenty of…um…stimulation for those lonely Saturday nights.
Good ol’ Miss Shields. Every teenage boy’s wet dream. And the only woman I could ever really want.
***
The bell rings as my last class ends. Mondays are always tough—especially if I’ve spent a recent evening with a girl like Andrea, a.k.a. the Volkswagen.
Avoiding them in the halls isn’t easy, because they’re looking for me. Of course they are: I’ve given them the best twenty to thirty minutes of their life (I was still working on my stamina, after all). So I usually have to take a different route to Advanced Physics and History of Russia just to keep my distance. There are days when evading the stage ten clingers feels like a full-time job.
You’re probably asking yourself how the word hasn’t spread through the debate team about my…behavior. Well I assure you, it has. There are almost thirty students on the team, and most of them are female. And as everyone knows, chicks talk. A lot. So why did they fall for my “charms” over and over again? Maybe it was curiosity. Maybe it was green-eyed jealousy—because what girl doesn’t want what their so-called friends have had? It doesn’t matter what they’ve heard, or even what they know to be true; they all think they’re going to be different from the one before—that somehow they’re going to be the one I decide to keep.
But there’s only one I want forever—and she doesn’t giggle when I walk into the room or think MTV’s Catfish is scintillating entertainment.
After spending an hour on homework, I set my phone down on my bed and stare at it.
It’s Monday.
My stomach rolls as I await my weekly text from Katie. This is, sadly, the highlight of my entire week.
She gets the debate topics on Mondays, and while the rest of the team gets them on Tuesdays, she’s always favored me and given me the information a day early.
That’s right: I’m her favorite. I just wish I got more out of the relationship than an early jump on the debate topics.
The anticipation pounds in my chest, and I walk to the window and look out to my car in the driveway. It was a gift from my father when I turned sixteen. It’s no Italian sports car, but it’s certainly the nicest car in the parking lot at school. Anything sexier than an Audi would raise eyebrows, anyway. I’d never want anyone to think I was a rich, spoiled brat with a small dick by getting a Maserati, Bentley, or—God forbid—anything convertible.