Sinful Tutoring: Next Semester Pt. 05

As her first full year of med school began to draw to its close, Cynthia May looked back on everything she'd managed to accomplish.

Not simply academically- although she was doing rather well on that front, being at the top of most of her classes and getting tons of praise as well, but rather her ever-growing stable of submissive little Trinkets. Mistress Syn had been extremely busy.

Two more professors.

A half-dozen of her fellow students.

Even one of the lab techs.

But that still wasn't enough to satiate her. Mistress Syn wanted more.

Now it wasn't as if those ones hadn't been lots of fun to play with- and still were, all things considered. Nor had any of them been lacking in their continued devotion and servitude. Her tuition was more than paid up for the remainder of her studies, and she'd barely needed to dip into her personal funds for anything at all.

And that wasn't even accounting for the countless other ways they paid for the privilege of serving her.

Yet as good as it felt to tease, torment, and dominate countless men and women around campus, Mistress Syn couldn't quite shake the lingering feeling that she could be doing more. That something was missing from her collection. Something even better than all of this.

She wasn't quite sure when the idea had finally popped into her head, but once it had, it outright refused to leave. Mistress Syn had been lounging around her dorm looking over her class notes whilst being waited on hand and foot by a pathetic little creep from one of her lectures. He'd made the poor life choice of trying and failing to 'impress' her with an unsolicited dick pic, only to now find himself naked, caged and licking her boots after she'd threatened to send it to all his friends and family.

Somehow, sitting there lazily watching him clean the dirt and filth from the bottom of her boots while she studied and smoked, the idea finally made itself known. Perhaps it had always been there- having taken root after she'd proven that she could more or less enslave anyone she pleased regardless of their status.

Yet even then it had remained hidden, deep in the confines of her wicked mind, waiting for the right time to spring forth. And once it did, Mistress Syn knew precisely what she had to do.

Fuck it. She'd come this far. There really was only one fish left to catch in this particular pond. The biggest one around.

The Dean.

Now Mistress Syn had never actually met the school's Dean, but she was familiar with him. Dean Winslow was an older man- circling his fifties if not already firmly ensconced in them, with slightly greying hair and a quiet, subdued demeanor. He'd spoken at great length to her and the other new students at the start of their first semester, and once or twice she'd spotted him around campus chatting with various professors about one thing or another.

However, unlike everyone else she'd managed to lure into her web, she'd had no real personal interaction with him. That had to change.

And she knew just how to do it.

First, she'd have to get his attention. Luckily for her, she had plenty of ways to do such a thing. Including one who was currently licking up a fresh mouthful of dirt and dust off of her boot.

Gazing down at him with a wicked smirk, she blew smoke at him to get his attention. The little shit- a far cry from the wannabe player who'd sent her that picture of his pathetic manhood, looked at her like a well-trained puppy, and she tried not to laugh at the sight of him.

"Sorry, Trinket. Looks like some of the pictures I took of you will be leaving my phone after all.."

Her sub- a skinny little redhead who clearly regretted the foolish actions which had gotten him into this situation but knew it was too late to escape, could only stare at her with terrified eyes. Mistress Syn simply smiled. "Don't worry. You'll be in good company when I'm finished..."

It took a little work- she'd had to create an anonymous account for this plan to work, but once that was taken care of, it was simply a matter of posting several of the pictures she'd accumulated over the course of the last several months.

Cruel as she could be- and she most certainly could be, Mistress Syn wasn't stupid. If she wanted to retain the subs in the pictures she'd leaked, she had to make sure that they, like her, would be seen as the victims in this situation. Nothing too extreme or humiliating was released- simply a few naughty pictures of them and her engaging in some fun activities.

Well, fun for her at least.

After all, in each and every one of them, it was clear to anyone who dared to look closer that she was in control of every situation. Just as she intended to be of what would hopefully come next.

Less than forty-eight hours later, the campus was in an uproar.

Just as she'd expected, the narrative, as it played out, was that someone had hacked a student's private files and released some dirty pictures. People all throughout the school were both appalled and intrigued, especially as they began to realize they recognized the subjects of the pictures.

Especially Cynthia.

She noted the shocked glances of her peers in class, took their words of comfort as well as their criticisms in stride, and happily played the role of the innocent, 'embarrassed' victim, though she made sure to wink whenever she noticed some of her Trinkets go red when their roles were pointed out. Honestly, that made it all the more worthwhile- their humiliation, minor as it was compared to what else she could have leaked, was so much fun.

Regardless, this was only phase one.

Alas, the second part of her plan took a little longer than she'd hoped.

Over a week passed before things began to fall into place, but once they did, Mistress Syn knew what to do. Just as she'd expected, she awoke one morning to an important email from Dean Winslow, asking to meet with her to discuss the "horrible" situation.

Mistress Syn quickly agreed, but added she could only meet after classes finished on Friday evening. The Dean said this was fine, not realizing he was playing right into her hands, and within seconds of her closing her phone, she set out to prepare for their upcoming meeting.

When Friday afternoon at long last arrived, Cynthia May walked into the school's main building, looking in every way the 'proper' student. A white, long-sleeved dress shirt covered up her tattoos, a modest black and white skirt hung over a pair of black leggings, and even her choice of footwear- a pair of open-toed black heels, was made to appear far more demure than she was.

All part of the plan.

She waited to be called into Dean Winslow's office, a smile on her face as the wheels spun 'round in her wicked mind. This wouldn't be easy, and could very easily go wrong if she mistepped. But if she managed to pull it off...

It would be amazing.

After fifteen or so minutes, she heard her name and stood up, entered the Dean's office, and shut the door quietly behind her as she let her eyes fall upon Dean Winslow.

He was just as she recalled from the times she'd spotted him around the school, with his glasses hanging off the end of his nose and his grey hair a mess. But when he looked up at her, his shock was clear. The older man nearly did a double-take, and she was quite certain she knew why. Somewhere in his mind, he was trying to wrap his head around this innocent-looking young woman standing in front of him being the very same one in the pictures that had caused such chaos around campus.

After a moment or two, he regained his composure, but Mistress Syn had already cocked him. This might not be as hard as she'd thought. She happily took a seat in the empty chair in front of his desk and waited.

"Good afternoon Miss May... So sorry we had to meet under such terrible circumstances."

Mistress Syn nodded, continuing to play her role to a tee. "Thank you, sir. I'm just shocked by this invasion of my privacy..."

Seeing as the Dean tried to put on an almost fatherly smile in response which was clearly masking something else, she knew she had him right where she wanted him. He would never see it coming.

"Um, yes... I wanted to talk to you about that... Of course, we are looking into who may have leaked the photos, but in the meantime, I wanted to discuss some of their more... salacious content..."

The sheer fact that he seemed unable to vocalize what was in the pictures made her want to giggle, but Mistress Syn held back. She couldn't show her hand just yet, too much was at stake. "Salacious content? Such as?"

She made sure to bat her eyelashes a little as she asked and noted the slight shift in Dean Winslow's expression. He was trying to maintain his facade of control and authority, but it was clear that regardless of his status, he too found himself more than a little intrigued by the young woman sitting in front of him. Especially after what he'd seen of her in those pictures...

"Well," he began," trying not to stutter as he opened the pictures in question on his computer. "While I don't judge what anyone does in their private lives, some of this is quite...."

"Quite what?" Mistress Syn inquired, her tone still mostly innocent with only the slightest trace of wickedness.

He looked so vanilla, it was actually quite sad. She wasn't surprised he couldn't even put into words what it was about the pictures that bothered him, if anything truly did. Mistress Syn clearly had her doubts about that. The fact that his eyes kept darting back and forth from them to her told her that a part of him was already imagining himself in the same position as her other Trinkets.

"Soon," was all she could think as she continued to wait for the older man to explain himself.

"I'm sorry," he finally managed with a shake of his head. "It's just... These images seem rather degrading..."

"Oh?" Mistress Syn said with mock shock, bringing a hand up to her mouth as if the very idea baffled her. "Degrading in what way?"

She wanted to hear him say it. Wanted him to explain in detail what was in the photos. To see what got the biggest rise out of him so that she could use it against him before their little meeting was over.

It took him a few moments, and in that time she'd carefully re-positioned herself in the chair, making sure that Dean Winslow would be able to see the black lacy bra she was wearing beneath the white dress shirt. Just when it seemed like he was ready his eyes immediately fell upon it, and that completely threw him off.

Good. She wanted him as unprepared for her as he could be.

"Well," he continued, managing to tear his gaze away from her even though it went straight back to the pictures of her. "In several of them, you seem to have other students... um... You have them licking your boots."

The fact that he sputtered that out made her smile. "What's degrading about that?" Mistress Syn asked, turning up more of her wickedness without removing too much mock innocence. "I thought they were being quite sweet. You have NO idea just how dirty my boots can get walking around campus all day.

As she said that, she swiftly lifted one of her legs, seemingly to prove her point as well as to draw the Dean's attention to her shoes as well as her panties, which she'd made sure he'd get a good look at as her skirt rose and fell. His eyes widened at the sight of them, and Mistress Syn knew she was getting close.

"I... I mean," he struggled, looking back at the photos for his next point. "In others... they are clearly tied up and gagged..."

"Is that a problem?" She asked, batting her eyelashes once again. "It's just a little harmless bondage."

She could see his defenses breaking, and as they did, Mistress Syn leaned over, allowing the slightly open top of her shirt to offer him a glimpse of her tattoo-covered chest. The older man's eyes were clearly drawn to it, and as he continued to stare, she knew the time had come to spring her trap.

"Are you alright sir?" Mistress Syn asked, returning to her more 'innocent' tone. "You seem a little flustered...."

Dean Winslow was more than flustered, but he was desperately trying not to show it. "I... I'm fine... But these pictures..."

"Yes," she interrupted, staring at him with harsh eyes. "My private pictures... Which you clearly have on your computer."

The older man gulped, but this was exactly what she'd hoped. Within hours of everyone talking about the pictures, Mistress Syn had wisely deleted the post and the account they'd come from. She knew plenty of people had probably downloaded them but she didn't care about them. She cared that the Dean had done the same. He'd have to for a meeting like this, but it was also something that could easily be turned against him.

Like it was right now.

"I don't like the fact that you kept them... In fact, they were leaked over a week ago, and yet you only reached out to discuss it with me a few days ago... What were you doing with them the rest of the time?"

Mistress Syn was glaring at him, and Dean Winslow stiffened up in his seat. Panic was beginning to set in, but he still tried to maintain some sense of control over the situation. "Well, these... these things need to be properly examined..."

"Oh, I bet you examined them plenty," Mistress Syn added. "Bet you looked them over again and again."

She was leaning towards him once more, yet even though she was seated, it felt like she was towering over him.

"I... I would...." He stammered, but Mistress Syn did not let up.

"You would what? Stare at them, lust over them, wish it was you in them?"

This was risky, but Mistress Syn was rather certain that Dean Winslow was no longer in a state to catch on to the obviousness of her plan. The fact that he continued to stammer and stumble over his words was proof of that. "No, I mean... We needed to... To make sure..."

"Make sure of what?" Now she was standing and truly glaring at him, any trace of innocence replaced by simmering rage. "Make sure you could get off to them like the old pervert you are?"

Had he been thinking clearly, Dean Winslow likely would have caught on to her and taken charge of the situation. But he wasn't, and with this dominant young woman staring at him, he felt as helpless as could be. "No, not at all... I...."

He was sweating, shaking, and that was as clear a sign as any that the time had come to really hammer him. "First my privacy is invaded, and now you are keeping my private photos on your computer for your own filthy ends... It seems to me that you're not handling this with the seriousness it deserves... Maybe I should get the police involved..."

The look on his face spoke volumes. In any other situation, the involvement of the police wouldn't have sounded like a bad thing, but the web Mistress Syn had expertly woven over the course of the last several minutes made it sound like the worst thing ever. He did have the photos in question on his computer- they wouldn't like that, even if his reasoning had seemed sensible at the start.

"Please, no," he said, his eyes wide with fear and more than a little lust.

"Hmm, I'm not sure," Mistress Syn continued. "You seem so focused on those pictures, it doesn't seem right to leave the situation in your hands..."

She took a few steps around the desk until she was standing beside him, and with a quick glance, confirmed her suspicions. A noticeable bulge had formed in his pants, either from the pictures, her presence, her words, or a mix of the three. Mistress Syn looked from it to him to his computer screen- and the pictures of her and her other Trinkets plastered all over it.

Without warning, she pulled his chair away from the desk, forcing his bulge into the open much to his shock and embarrassment.

"I knew they were getting you excited!" She shouted, forcing Dean Winslow to cover his crotch in a panic. "You filthy old pervert. I'm definitely going to call the police now."

Turning on her heel, she kept her back to him for a moment and only took two steps before she heard his panicked fumbling behind her.

"No, please... I'm sorry... It's not what it looks like... it's.."

Looking back, she spotted a picture on his desk. One of him and an older woman- his wife clearly, a fact more or less confirmed by the ring on his finger. She grinned. "It's that wifey doesn't make you feel the way those pictures do, does she?" Her tone was wickedly seductive, and if Dean Winslow had any defenses left, they would have fallen then and there.

"No..." was all he said, his head hung low and his voice quiet.

"I didn't think so..." Mistress Syn continued, stepping back towards him. "But you've clearly been a naughty boy, and we can't have that..." Hands on her hips, she stared at the broken man seated before her and prepared to deliver the coup de grace. "If you want to keep this under wraps, I think you should kiss my feet."

Perhaps it was the unexpected stress of the situation, the way it had clearly gotten away from him, or the fact that somewhere deep inside he had wanted nothing more than to do just that ever since he'd first skimmed through the pictures of others doing the very same, but in that moment, Dean Winslow ceased to exist. The proud man who had overseen the school for decades was gone, replaced by an empty shell too terrified and turned on to think clearly.

Which is why he slipped out of his chair, onto the floor, and immediately pressed his lips to Mistress Syn's black-painted toes.

And as he kissed them, the sound of a camera flash echoed out in the otherwise quiet office. Followed by several more.

Looking up, Dean Winslow saw the phone in Mistress Syn's hand, as well as the wicked smile plastered all over her face. And in that moment, he knew he was really and truly fucked. Just like everyone else who had the poor luck of being the subject of those other pictures.

"I didn't say stop, did I Trinket?" She asked with a grin. "Keep kissing my feet. We have a lot to discuss."

With a sigh, he did just that, only stopping for a moment as Mistress Syn took a seat in his chair.

It was quite fitting after all. He was no longer in charge- of himself or the school proper anymore.

Mistress Syn was.

And she was going to make damn sure he and everyone else knew it.