Mr. Sterling's Dilemma

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Young teacher wants his student.
10k words
4.65
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38

Part 1 of the 2 part series

Updated 06/11/2023
Created 02/11/2022
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"Janie, for God's sake, just go ask him."

I glance up, seeking out the irritated whisper I just heard. My best student, Caroline, is standing in the middle of the classroom beside Janie Greenberg's desk while Janie stares wide-eyed up at her. The whisper came from Caroline, if her apologetic smile in my direction is anything to go off of.

"Can I help you two?" I ask, glancing at the clock above the doorway. Everyone else filed out of the room about two minutes ago. I assumed Janie and Caroline were just slow movers.

"Janie has a question," Caroline says assertively, cocking her head in Janie's direction, at the same time that Janie blurts, "No, we're great, Mr. Sterling!"

"Okay..." I drawl, leaning back in my chair and folding my arms over my chest. I lock my gaze on Janie, who has started scrambling out of her seat. Her plaid skirt flounces around her thighs as she manages to climb to her feet. She is significantly shorter than Caroline, and she seems to gravitate towards the taller girl for comfort.

"You gave her a C on her last essay," Caroline says after a few more seconds of silence and staring.

"Which is totally fine!" Janie chimes in, an anxious smile spreading across her red face. "I feel great about it." When Caroline nudges her in the ribs, Janie scowls at her and then huffs. "Okay, well, I don't feel wonderful about it, per say. Um, I just would like to know what I did wrong? You didn't mark it or anything. Which is fine, I just--"

"Dear God, Janie, pull up a chair," I interject, sitting taller and pointing to one of the extra chairs at the front of the room. Janie fumbles her way over to it and sits down next to me, so close that one of her knees brushes my thigh. I shoot her a pointed look, and she rambles apologetically as she increases the distance between us. I already noticed her soft, shapely thighs, however, so the damage is done. Even encased in gray wool tights, they are lovely.

Caroline pats Janie's head and says she will wait outside, leaving us alone to sit in awkward silence.

"I don't have your paper memorized, Janie, I assumed you would provide it," I say flatly, folding my hands over each other in front of me. She looks embarrassed as she rushes to pull it out of her bookbag, but I am too disgruntled by her sudden proximity a few moments ago to really worry about it. Her eighteenth birthday was just a week ago, which makes my thoughts less illegal but still incredibly inappropriate, given my position.

She places the paper on the desk in front of her, and I notice her pale, shaking hands. I eye her speculatively, noting her soft-looking gray sweatshirt and, of course, the illustrious wool tights. She doesn't seem cold, but I still decide to ask.

"Chilly?" I inquire, nodding to her trembling hands. She flushes a truly fascinating shade of red, and I fight back a chuckle.

"I--well--no. Just nervous."

"Do you have a speech to give after this?" I ask, despite being pretty confident that she is just scared of me. It is a curse of my size: I am 6'5" and broad-shouldered, and I use working out as an opportunity to get out my restlessness at night, so I am much more muscular than the men this poor girl is used to seeing. I have seen people in grocery stores be visibly disturbed by my appearance, and I am sure she is no different.

"No, this is the speech," she grumbles, putting her chin in her hands as she leans her elbows on my desk.

"I don't mean to intimidate you, Janie," I say quietly, giving her what I hope is a reassuring smile. She furrows her brows and waves a dismissive hand.

"Oh, I'm not intimidated by you, I'm just scared you think I'm dumb and stupid," she explains, tucking a few light brown locks behind her ears. I chuckle and smile at her, relieved that she is just a perfectionist and not scared for her life.

"I don't think you are stupid at all. This material is difficult to understand, and you have done exceptionally well up until this point." She brightens at my praise, and I briefly wonder if praise plays a role in her pleasure in bed. Clenching my jaw, I look away from her and back to her assignment.

"That's a nice thing to say," she says, beaming at me now. I look away, uncomfortably charmed by the warmth of her gaze, and glance back down at her paper.

"Well, it's true, so don't get worked up over it," I grumble, mentally kicking myself when the smile slips from her pretty face. I distract myself by scanning her intro paragraph, which is lovely, hook and thesis more than accounted for. I write a red check next to it and move onto the next paragraph, where the trouble begins.

Janie scooches a little closer to peer over my bicep at what I am writing on her paper, and I have to restrain myself from tucking her beneath my arm to give her a better look. I do shift the paper closer to her, however, so things will be slightly easier.

"Okay, your first issue is your argumentative paragraphs," I begin, meeting her gaze. She has apparently been staring at my arms, and her cheeks are rosy when she realizes she's been caught. I am no better, though, so I didn't say anything, just clear my throat. "You explained both examples well, but you didn't connect them back to your thesis, and the connection wasn't clear enough by itself for that to slide. This week, just try to draw stronger conclusions. Don't assume that I'm on your wavelength. You have to take me to your thesis and keep me there. I took off ten points for each time you didn't connect back to the thesis, and then a couple points here and there because of grammar and spelling. It does not seem like you proofread this."

"Okay, I'm sorry," Janie says, eyes locked on her hands, which are clasped over one of her knees. She looks like she is near tears, and remorse rips through me. "I'll do better this week."

"I know you will," I assure her, offering her a small smile. It is barely a quirk of my lips, but it seems to lift her spirits, and some of the warmth returns to her soft dark eyes. "It's okay to screw up every now and then, Janie. It doesn't change my opinion of you as a student or a writer. I never want you to be near hyperventilation at the thought of talking to me about your grades, okay? I am here for a reason."

"Yes, I know," she says, nodding rapidly. A wayward brown curl settles against the curve of her cheek, and I resist the urge to tuck it back behind her ear. She waves her hands, gesturing to me as she speaks. "I just don't want you to think I'm a brat or anything, and I didn't want you to think that I was gonna try to negotiate for a better grade. I know I deserve whatever grade you give me, I just wanted to know why, you know?"

I nod because I do know what she means, but my idiot brain latches onto the part of her sentence where she mentioned negotiating for a better grade. It is hard to imagine innocent little Janie using her feminine wiles to get an A, but the idea is certainly enough to distract me from her words. And, based on my reaction to the warmth of her thigh, I would be putty in her hands if she ever tried anything.

"Well, I guess I'll be on my way, then," Janie announces, smiling nervously at my continued silence. I nod and stand, hoping she won't look down at my pants as I walk with her to the door. She smiles at me as she joins her friend in the hallway, all rosy cheeks and long hair, and I barely manage a nod before I shut the door and look away from her.

***

My newfound attraction to Janie Greenberg thankfully does not seem to be apparent to anyone but me. I avoid eye contact with her for a week after our after-school meeting, which isn't difficult since she is a rather quiet student, but I can't help but feel guilty, like I am punishing her for my own weakness. It isn't her fault that she has the curves and charm of a woman much older than herself. But that doesn't mean I am willing to put myself in temptation's way.

I have resigned myself to completely ignoring her existence, and it is going well until the Wednesday after I begin pretending she didn't exist. I am driving home in the pouring rain, listening to a podcast about Cyrus of Persia, when I see a familiar head of dark hair on the side of the road. I slow down to get a better look, and sure enough, the subconscious object of my fantasies is trudging through the mud on the side of the road, a knee-length raincoat hiding her shape from me. Thank God. A rain-soaked Janie would live in my brain for eternity.

"Janie?" I call, pulling to a stop beside her and rolling down my window. Rain hits my face, but I don't mind, entirely focused on Janie. I haven't let myself look at her for a week and a half, and the reminder of her sweet face is soothing. She is so lovely, feminine and rosy, if a little damp at the moment. "Can I give you a ride, sweetheart?"

Shit. I hadn't meant to call her "sweetheart," although she doesn't seem disturbed, jogging over to the passenger side and hauling herself into my car. Her coat rides up, exposing damp gray tights and the hem of her blue skirt.

"Thank you so much," she says, sighing in relief as I turn the heat up to full blast and point the vents in her direction. She relaxes back into the seat, breathing heavily, and starts blowing on her hands to warm them up.

"I think there's a towel in the glove compartment, if you need it," I tell her. I always keep towels in my car, given the propensity for rain in this town, but I am extra grateful to have them today.

She shoots me a thankful smile and finds the towel, immediately rubbing it along her thighs. I clench my jaw, cursing myself, and turn my attention to the road ahead of me as I put the car back in drive.

"Put your address in here," I order gruffly, opening my phone and handing it to Janie. She sets the towel down on her lap, pausing my torture for a moment, and follows my instructions. Once I know where I am going, I focus all my attention on the road and do my best to keep ignoring the woman--no, girl--beside me.

"I, uh--are you mad at me, Mr. Sterling?" she asks quietly ten minutes later. She lives rather far out from school, and we still have fifteen minutes left before we reach her house. I am glad I saw her. I can't imagine her making such a long walk in this weather.

"What?" I shoot a glance at her out of the corner of my eye, and she looks completely serious, her brows furrowed in concern as she stares down at her lap. "No, of course not."

"I just--well--you've been ignoring me. Like, really ignoring me. Big time. And I mean, it's not like you were focused on me in class before, obviously, but now it's like you're consciously choosing to pretend I'm not there. I mean, probability-wise, you should've at least accidentally looked at me at some point over the past couple weeks. You did before. So I feel like I did something," she explains, speaking quickly and stumbling over a few of her words.

The guilt returns, full force, and I exhale heavily as I try to figure out how to respond. I settle on honesty.

"I think you're pretty."

She is silent for a moment, and when I glance at her out of the corner of my eye, she is eyeing me incredulously as she methodically dries her hair with the towel. Her coat is unzipped now, and I can see her tiny skirt and that gray sweater again. God, it's not even a very appealing outfit, but she looks so soft and disgruntled, like a little kitten.

"So?" she says, finally breaking her silence.

"What do you mean, 'So?'" I ask, shooting her a brief glare before returning my attention to the road. She folds her arms across her chest and turns sideways so that she is facing me as best she can despite her seatbelt. "That's bad news, Janie. You are my student and a teenager. I am 31 years old. It's gross for me to find you attractive."

"No, it's not," she dismisses, waving one tiny hand and rolling her eyes. I resist the urge to bend her over my knee and show her exactly why my attraction is a problem. "I'm 18, so you're not a pedophile or anything, and besides, I've been built like a mother of 4 since I was 13. If you're attracted to women, and you can get past my face, it's normal that you would be attracted to me a little bit. I'm sorry you realized I had boobs halfway into the year, though, Mr. Sterling."

I growl under my breath, flexing my hands on the wheel at the nonchalance in her tone.

"It's not...damn it, Janie," I mutter, scowling at the road. "It's not your breasts, really. They are pretty well hidden, thank God. It's... you. Your cheeks and your mouth and hips and eyes and thighs. Your hair. All of you. You have for some reason become very attractive to me in the last week, and I know that doesn't make me a pedophile, but it does make me a creep. You are my student."

She is silent again, and she's blushing when I look at her, a tiny smile playing on her lips. Dear God.

"I find you attractive, and I can still look at you," she says quietly a moment later. "I don't ignore you. Because I'm not a baby."

"Yes, you are," I manage, gritting my teeth. "I bet you've never even been fucked."

She inhales sharply, and I can see shifting her hips out of the corner of my eye. I shouldn't have said that, but her reaction is worth it.

"Well. At least I'm not scared of my feelings," she sniffs, rolling her eyes. "And when I am... fucked... it will be at the hands of a man who isn't afraid of being attracted to me."

I pull over immediately. Shove the gear into park. Janie's breathing has increased, and she watches me, wide-eyed, as I throw the car door open and stride to the passenger side. She starts to speak when I open her door, but I put my hand over her mouth as I tug her body closer, stepping between her thighs. She's impossibly warm, and dry now, although I suspect she won't be for long. The rain has reduced to a drizzle, but it still gets my shirt damp as I run my gaze over her body. It's absurdly arousing, the sight of my body wedged between her curvy thighs. I take my hand off her mouth, and she's panting, watching me. She doesn't speak, though, as I step closer, pressing my tented crotch against her core. She moans, nearly falling backwards, but my hands on her keep her in place.

"This is why I can't look at you. This is why it's bad that I find you pretty. When I look at you, this is what I want to be doing. I want you to open your pretty legs and let me in, so I can fuck you like I know you need to be fucked. I want you to get on your knees and suck my cock until I come down your throat. I want you so badly, but nothing can ever happen," I growl low into her, feeling her perfect body trembling against mine. She's aroused, I can tell. I step away, and she whimpers in protest, earning a dark smile from me. She presses her thighs together and subtly grinds into the seat, trying to create some friction.

"Tomorrow, when I'm avoiding you like the plague, I want you to think about this, Janie, so that you'll remember why," I say, softer now, cupping her face in my hand and running my nose along her cheek. I'm soaked now, the drizzle having returned to a full rain, but I don't give a shit.

"O-okay," she whispers, hands locked around my biceps. When I go to pull away, she doesn't let go until I pry her fingers off me, and then she collapses back against the seat. I wonder if she came, although I can't imagine how.

I pull up to her house a few moments later, and she scrambles out of my car, sending a haphazard wave in my direction. I swear under my breath. Way to fucking go, idiot.

***

Janie is quiet for three days. She doesn't seem upset; she just sits quietly during class with her chin resting on her palm, gaze locked on me. She smiles when I look at her, and I breathe a sigh of relief each time. She doesn't seem uncomfortable with what happened, but she's not putting me in a weird position by trying to instigate something else. Which is more than I did for her.

The guilt consumes me, especially in the evenings. I go to a bar on Friday night, two days after giving Janie a ride home. A woman invites me to go home with her, and I happily agree, eager to get somebody else's thighs on my mind. It doesn't work, just fills me with a different guilt for being between two different women's legs over the course of three days.

In class on Tuesday, Janie wears stockings instead of tights. That is allowed in the dress code, and it's a flukey warm day in the middle of winter, so I understand why she did it. The sight of her black garters and sheer tights beneath her skirt makes my fingers curl into a fist when she swishes into my classroom.

Caroline is next to her, also in stockings, but my attention skims over her and returns to Janie. She meets my eyes and raises one eyebrow when she sees the scowl on my face.

"Good afternoon," I greet, clearing my throat after the bell rings. Janie crosses her legs, and her skirt rides up, exposing her black garters to me. I swear under my breath as I pull up the powerpoint I will be going over today. It's on Dante's Inferno. When I begin talking about the fifth circle, the home of sexual sinners, Janie smiles into her hand and winks at me.

Minx.

I travel around the classroom, handing back the essays from last week. Janie has returned to her roots of straight A's, and the relieved smile on her pretty mouth makes me want to touch her sweet face. As I'm walking past her desk, she slips a folded-up post-it note into my hand. I shoot her a cursory glance, but she's staring straight ahead, brushing her hair from behind her ear to shield her face. My pretty girl is not nearly as bold as she thinks she is.

I grit my teeth at the direction of my thoughts. Not my pretty girl, just a pretty girl.

I tell the class to pack up five minutes early so that I can read Janie's note and decide if I need to yell at her.

I want you to do it again.

It's vague, vague enough to be taken in a nonsexual context if someone else were to have accidentally seen it, thank God. I look at her, and she's animatedly speaking to Caroline, twisted around in her chair. Those fucking garters are still visible.

I know what she wants me to do again. She wants me to press my erection against her sweet pussy and tell her exactly what I wish I could do. I tell myself I don't want that, and that is enough for now.

"Janie," I call, just as the bell rings, crooking my finger to bring her to me. She says something to Caroline and then walks to me, pulling up a chair to sit in. She sits close like she did last time, and I clench my jaw, holding myself perfectly still until every student has left the room.

"D-do you need something?" Janie asks, clearing her throat and giving me a nervous smile. Now that we're alone, she's anxious. I can tell she's worried. Good. She shouldn't feel comfortable writing me dirty notes.

"I don't know, little one, it doesn't seem like I'm the needy one here," I say flatly, locking my gaze on hers. Her eyes widen, and she blushes, folding her arms across her chest. "What exactly did you want me to do again, Janie? Did you not understand something from the lesson? Should I go over it again?"

Her shoulders slump, and she scowls, pouting petulantly.

"You know what I mean," she mumbles, looking away from me and scooching down in her chair like a delinquent. It makes her skirt ride up, and I snap.

I stand up quickly, making Janie jump in surprise, and stride over to the door to close and lock it. I turn off the lights and close the blinds, but I turn on my desk lamp so that I can see her. Anyone walking by would just think I've left for the day.

I walk back to Janie, who is sitting wide-eyed in her chair by my desk. She looks nervous, but her gaze is dark, and I know that look: lust. She wants me to fuck her. I won't, but the thought certainly makes my cock harden.