Chapter 1
As the midday sun rose to its zenith, Anonymous spun in his chair, a pencil in each hand as he air drummed in a bid to stave off the boredom.
One more hour, he thought. Just one more hour for the staff lunch to run its course and he could then escape his office and take a more proactive role in his duties. Not that he’d be one to complain. After all, Principal Celestia did set him up with a surprisingly decent package, especially considering what was for all intents and purposes an entry level job. A surprisingly spacious second-floor office with a view of the soccer field, paid holidays and vacations and a surprising amount of freedom in the way he went about fulfilling his duties. Yes, one could certainly do a whole lot worse than this cushy gig.
Well, supposedly cushy.
In truth, he did not know what to fully expect, this being his first day on the job. He’d already met a number of his new colleagues, using this opportunity to inquire about the former sex counselor and why he’d abandoned such a seemingly decent job.
Exhaustion and fatigue.
That’s more or less what it all amounted to, and after she’d had a fair number of drinks on her, Vice Principal Luna let it slip that, under ‘advice’ from her sister, she’d been exhaustively searching for the perfect candidate. He must be young, Celestia insisted, in the prime of his life and in exceptional physical health to keep up with the more rigorous aspects of the job.
Vice-Principal Luna, ever the thorough recruiter, naturally insisted she get a firsthand account of his skills, and after locking the door to her office, Anonymous then proceeded to give her an exhaustive demonstration of his talent. One and a half hours later—spent, panting and disheveled—Luna declared him to be a perfect fit for the role and hired him on the spot.
She presented him with a thick stack of papers. The usual stuff, guidelines, rules and expectations for his role as the new sex-ed counselor. Included was a suggested diet plan and exercise regimen that would keep Anonymous in tip top shape. He thought it to be a moot affair, seeing how he’d already done an exemplary performance, and Luna readily agreed. That said, she did warn him against becoming complacent and slacking off, proclaiming her energetic young students would run him ragged if he allowed himself to falter.
Of course, fitness was only a part of it. The job also required a specific type of mindset. Patience and empathy were crucial when dealing with young students still getting accustomed to the deluge of hormones that flooded their bodies and wreaked havoc with their emotions.
Anonymous shuddered as he too recalled this particular time in his life. Puberty sucked. A condition not exactly helped by taking legions of horny, stressed out, socially impaired, anxiety-ridden time bombs and cramming them together like sardines all in one place.
If nothing else, at the very least he could take some pride in helping his young, impressionable charges ride out some of the worst aspects this period in their lives would bring.
Speaking of, where were they? He’d done fuck-all these past four hours. Probably to be expected. If these high schoolers were anything like he and his friends back in the day, they were probably still trying to shake off the dregs of sleep.
A telltale chime snapped him out of his musings, and he turned to his computer to see a notification from Vice-Principal Luna. He smiled as he scanned the contents of the message. In ten minutes, she’d send a student his way—a repeat troublemaker by the name of Rainbow Dash.
Anonymous pulled up her file. A spirited jock with no shortage of infractions on her record. An excitable short temper that incited arguments, fights and the like. Subpar grades. No surprise, yet Anonymous shook his head at the latest in a long line of grievances against the young girl, and was in the middle of conceiving a plan for how he’d deal with the irascible girl when a knock on the door signaled her arrival.
Smoothing his dress shirt and tie, Anonymous adopted a professional-yet-casual stance and called, “Enter.”
The knob on the door turned slowly, and it opened as such. Rainbow Dash(she certainly lived up to her name) entered with an air of sullen resignation, a hand picking at the hem of her skirt as she tried to look about the room with what was probably meant to be cool indifference.
“Rainbow Dash, I presume?” Anonymous said pleasantly.
Rainbow grunted what might have been an affirmative.
“Please, take a seat,” Anonymous said, motioning to the comfy armchair on the opposite side from where he sat.
She did so, grumbling something under her breath.
“Didn’t quite catch that,” Anonymous said.
“I said it’s a waste of time,” Rainbow said, her arms folded, speaking properly for the first time. Her voice had a slightly rough, raspy quality to it, which Anonymous found charming. “Just give me detention and let’s get this over with.”
Anonymous smiled. “I don’t give out detentions.”
Her features softened somewhat in confusion. “So why am I here?”
“We are here to talk. About you, to be precise.”
She shrugged. “Talk, then.” And looked away.
Anonymous resisted the urge to sigh. “Do you know why you were brought here?”
Rainbow rolled her eyes. “I got in trouble, duh.”
“And what was it you did that got you in trouble?”
A faint tint of red colored her cheeks.
“Allow me to elaborate, if you will. You are here because you tried to force yourself on a boy. Is that the right of it?” Judging by the way her face flared a tomato red, he had the right of it.
In a flash, she stood over him, both palms laid flat atop the desk. “It’s a lie!” she said heatedly. “I wasn’t gonna force him to d-do that! I just... just...” she trailed off as Anonymous held up a hand.
“Let’s not get wrapped up in accusations. Sit, please.” She did so, the bright red hue not leaving her cheeks. “Rainbow,” he said patiently. “We all have urges. It’s natural to want to act on them, to want to explore them with another, but only if that second party agrees to it.”
Rainbow made a frustrated groan. “I know that. I know, okay? It’s just... sometimes it...”
“It’s too much, right?”
“Yes!” she said, throwing up her hands. “There’s times all I can think of are boys! A-and, and... doing things with them. To them...” she trailed off in a whisper, looking away in embarrassment.
“Have you,” Anonymous said carefully. “Tried getting closer to them? In a friendly pretext, with no ulterior motives.”
She rubbed her arm. “I mean, I try, but... but then I start thinking about...” She shook her head. “What does it matter anyway? They’re too intimidated by me! I’m too much for their soft little skulls!”
Anonymous frowned. Not because he didn’t believe her, but rather because he did. Rainbow carried herself with an air of confident, aggressive femininity. He’d stake his job on it in that she came on way too strong and scared off any potential partners. A problem that must be rectified before it grows into something harmful.
“I’ve noticed your grades have tanked this past semester. Any particular reason why?”
Red-faced, Rainbow turned away, shrugging.
“Do you perhaps have trouble focusing?”
“...Maybe,” she muttered.
“Thinking about boys?”
She blushed more heavily.
“Have you tried softening your approach? Toning down the intensity?”
Rainbow fixed him with a strange look. “Wha... why?”
“You might find them to be more receptive.”
She scoffed. “As if! Boys like a confident, feminine girl. My mom says so!”
“And how’s that working out for you?”
Rainbow bit her lip and looked away, sullen.
“Look,” she said. “You’re a guy. You wouldn’t understand.”
“Try me.”
“It’s like...” she floundered for a moment and made a frustrated sound. “Look, I know boys like girls with a certain... body type.” She brought both hands within a foot of her pert chest and made a vague motion. “I have a few friends who... I mean, I’m not built like them, so... so...”
“Would you stand up for me?”
“I... wha?”
“Stand up.”
Rainbow blinked owlishly, but did as told. Anonymous followed suit, leisurely walking around his desk and Rainbow herself, stopping behind her. She barely reached past his chest. Rainbow gasped as his hands cupped her modest breasts.
“They’re quite lovely Rainbow,” he said, softly kneading them. “You have nothing to be ashamed about.”
She mumbled something.
“Come again?”
She turned her head to look him in the eye, her features softened. Vulnerable.
“You’re a teacher. You’re supposed to say that.”
Anonymous smiled. “Am not, to both counts.” In one swift motion he grabbed the hem of her shirt and tugged it up past her chest. Another motion and her breasts were freed to the cool air of the office, her perky blue nipples stiffening under the ambient temperature.
Rainbow bit her lip, eyes closed, her hands balled into fists. Soft, squeaky whimpers, barely audible, could be heard as Anonymous lightly pulled and rolled her nipples in his fingers. Knowingly or not, Rainbow pressed her back to him, arching her chest, hoping to prolong the pleasure.
“Rainbow,” Anonymous said calmly. “Your teachers and I want what’s best for you. That’s the whole point of school.” His hands retreated, resting on her shoulders. “And at the risk of sounding like an old man, I know what it’s like. I’ve been there. Not that long ago, actually.”
Firmly, but gently, he turned her around to face him. The brash girl now subdued, her head slightly lowered, not meeting his gaze. Her eyes snapped up as she heard him trying to hold back amusement.
“What?” she said, a bit of the fire back in her voice.
“You are so cute,” he said and used a finger to boop her nose.
She batted it away and grumbled, “I’m cool, not cute.” Her lips twitched into the ghost of a smile.
“In all seriousness,” Anonymous continued. “We need to do something about the way you approach boys.” She frowned. “I assume you want to graduate high school with at least one boyfriend under your belt?”
She flushed even deeper and said, “Yeah.”
He played with her nipples again, teasing them. Rainbow’s breathing grew heavier.
“I’d like you to do something for me,” Anonymous said. “Next time you talk to a boy, I want you to try and be a bit softer. More patient.”
She scoffed. “What, you mean masculine?”
“As you are now, I mean.”
Rainbow stiffened and looked him in the eye.
Anonymous smiled. “Not hard at all, is it?” She remained silent. “Trust me, Rainbow. Boys like a girl who knows when to let her guard down.”
“O-okay,” she mumbled. “I guess I can try it.”
“I’m glad you agree. But there is still one issue to deal with.” At her questioning look, he said, “Your grades?”
Her face scrunched up. “Oh.” She sighed. “Look, it’s just hard to focus sometimes. I’m always thinking about boys and... a-and sex and...” she made a vague gesture with her hand.
“Fortunately, I believe we can do something about that now.” Anonymous then stopped playing with her nipples, much to Rainbow’s dissatisfaction, and instructed her to turn around and bend over, hands resting atop the sturdy wooden desk.
“Like this?”
“Perfect.”
His fingers then found purchase on her skirt and the leggings beneath it and promptly pulled them down, leaving Rainbow’s bare ass proudly on display. She squirmed slightly, glancing back with a hopeful, almost shy look in her eyes.
“Well,” Anonymous said, running the back of his hand across her smooth, tight bottom. “You take good care of your body.” She shivered under his touch.
“’S flat,” she mumbled, looking away.
“Nonsense,” he said. His fingers traced a path to her moistening slit. “It’s athletic. You’d be surprised how many guys are into that.”
Blushing, she turned her head to look, lips quirked into a cocky smirk.
“Like you?”
“Exactly.”
Rainbow moaned as his fingers carefully entered her, stroking the folds of her pussy. She bit the collar of her jacket in a bid to muffle the sounds of pleasure that threatened to spill from her lips. His fingers stretched her inner walls with surprising delicacy, patiently rubbing them as they gradually tunneled deeper, deeper inside her.
He pulled out. Rainbow lay flat against the desk, hands balled into fists, panting, her body heaved as she took large breaths.
There was the unbuckling of a belt, the telltale flutter of fabric hitting the floor. Shakily, Rainbow turned her head to chance a peek. Anonymous stood at full mast, glistening with precum. She gulped as he drew nearer, her hammering heart made it difficult to hear anything but the pounding of blood. His hands found purchase in her hips, holding them in a surprisingly firm, yet gentle grip.
He thrust his hips methodically, his dick trailing back and forth beneath her soaking folds in rhythmic motions, coating himself in her slick fluids. Rainbow did not remain idle. Her hips bucked experimentally, hoping to grind herself onto his thick, almost searing manhood. Her technique was far from refined and left her wanting, something she noted grudgingly.
Satisfied he was slick enough, Anonymous then pulled back. Rainbow met his eyes questioningly. His mouth opened and closed. Was he talking? Probably. The blood in her ears pounded even more intensely, to the point she couldn’t make out the words.
Frustrated and aching for release, Rainbow spread her legs, lifted her hips and wiggled her pert butt in the hopes he’d take the hint.
Anonymous needed little encouragement. He lined himself up with her entrance and, carefully, began to push.
Rainbow sucked in a breath as a girthy, meaty something opened her up, wracking her body with waves of sensations that treaded the line between ecstasy and agony. Her nails clawed at his desk, her back arched as he slowly, slowly filled up her aching tunnel.
When he at last hilted himself, and when she felt his pelvis make contact with her bottom, Rainbow exhaled a long, shuddering breath. She chanced another look back. Anonymous was flushed, his chest heaving. Rainbow smirked at knowing she had this effect on him, that she and her body could crack that professional image he’d been putting up for her benefit.
She clenched herself around him, her smirk growing as his face immediately gave away the effect. No words were said as they locked eyes and, with a knowing glint of his own, he met her challenge head-on. His hands still on her hips, he gradually pulled out, the tip of his cock still inside her and in one smooth motion he filled her up anew.
She was powerless to resist and moaned in response. Anonymous seized this moment of weakness and showed no mercy, withdrawing and hilting himself in smooth, powerful thrusts. His hand then found her stiff nipple, tweaking it, pinching it, eliciting a surprisingly girly whine from the headstrong athlete.
Wet slaps and heaving breaths filled up the office. Rainbow had long given up and lost herself to the pleasure. Anonymous was not far behind, but restrained himself. This was for Rainbow first and foremost, after all.
Her first climax came hard and it shook her to her core. Her back arched almost to the point of concern, her knuckles white as she gripped the rim of the desk, her mouth opened to the heavens in a silent scream.
Offering her leeway, Anonymous slowed down his efforts. His thrusts became softer, gentler. At some point he’d maneuvered her lithe body so that she now lay with her back to the desk, her toned, slender legs propped onto his broad shoulders.
Rainbow’s hands clutched at her hair, all but growling in pleasure as the new angle allowed Anonymous to touch an even deeper part of her. His mouth found one of her nipples, lightly sucking it, and her second orgasm followed soon after. More mellow this time around, but no less satisfying.
She came again eventually. Once, twice more, who could say? At some point her mind blanked out, the unrelenting waves of pleasure blurring together in a single, hazy fog.
Spent, panting, barely cognizant of the world around her, Rainbow laid there as Anonymous carried her to a nearby couch and cleaned her up, dabbing her with moistened towels, wiping the horribly sticky mess they’d made as best he could.
“Wow,” she said faintly, one arm over her belly, the other resting atop her head as she remained on the couch. “That was... it was...”
“A relief, no doubt,” Anonymous said as he finished smoothing out his tie. “You’ve been pent up for a while. Am I right?”
Rainbow nodded. Anonymous walked behind his desk and bent down, returning with a large bottle of orange sports drink and a packet of peanut butter crackers which he offered to Rainbow.
“Drink. You’ll need it.”
It wasn’t until she took that first sip that Rainbow realized how parched she was. The bottle was emptied in seconds. The crackers followed suit, then a healthy burp.
“S’cuse me,” she said, covering her mouth.
Anonymous smiled as he took a seat beside her. “How do you feel? More... clearheaded, I hope?”
Rainbow’s brow furrowed as she pondered this. “You know what? Yeah... I can,” she hesitated. “My thoughts are not as jumbled. I can think more clearly now.”
“Then from this point on, you have no excuse.” At Rainbow’s questioning look, he continued. “You can’t concentrate in class because sex is on your mind, right?”
She huffed. “Okay, okay, I get it. I’ll do better from this point on.”
“And?”
She rolled her eyes. “And I’ll be gentler and more patient with boys. And not force myself on them.”
“That’s what I like to hear.” And with a slap on his knees, Anonymous stood. “And as much as I’ve enjoyed our time together, I believe you still have classes to attend to.”
Rainbow nodded and followed suit. She hesitated as she stood at the threshold of the door.
“Yes?”
“Can I...” She turned to face him; a bit unsure. “Is this a one-time thing? Can I... c-come back?”
“That depends entirely on you. This was meant to help you, Rainbow. Help clear your head so you can better focus on your studies. It’s not a pleasure house.”
She stepped closer, a fire in her eyes. “B-but if I can do it... if I get better grades and, and behave and stuff. Can I come back then?”
“If you keep your promise?” He ruffled her hair playfully, much to her annoyance. “You can come as little or as often as you like.”
“Deal!” she said and, before Anonymous could react, she was suddenly in front of him. She stood on her tiptoes, her lips lightly brushed his, and just like the wind she was gone.
Anonymous stood there, befuddled. He smiled and shook his head. She really was a nice kid. A bit rough, but full of promise. He was about to close the door to his office when his stomach vociferously voiced its protests. He looked to the clock. Five minutes before lunch was over.
His rigorous session with Rainbow would have tired the hardiest man under normal circumstances, yet he’d been fueled with nothing but coffee for the better part of the day. He needed nourishment. So with that in mind, Anonymous threw open the door to his office and made a mad dash for the well-treaded path to the school cafeteria. It was chicken pot pie day today and he had nothing but excellent memories of it during his time at Canterlot High School.
In fact, he thought as the smell of food drew closer and closer, I think I’ll have two pot pies.