Sinful Tutoring Next Semester Pt 04

She felt him grow harder beneath her. His manhood pulsating with desire, aching for her and everything she could offer him. He was so fucked, and she knew it.

Things had been pretty boring for Cynthia all things considered. Her second semester of med school had begun, and though she had continued to toy with her newfound Trinkets as often as she could, it was starting be feel all too easy. She had them where she wanted them, and they did as she commanded whenever she deemed them worthy of being in her presence.

But as fun as owning such pathetic fucks as them was, she wanted more. A challenge.

And one afternoon, she found it.

She'd been sitting in class, half paying attention to the lesson half scanning the room for potential prey, although no one was jumping out at her. They all reminded her of the ones already under her thrall- ensnaring them would be too easy, and too much of the same.

Then it hit her. The professor!

Professor Daniels was in his early forties, with a bit of a dad bod, but otherwise quite easy on the eyes. He was also in a position of authority, and that tickled Mistress Syn's fancy. If she could draw him into her web... Well, the sky was the limit.

The question was how. Her previous victims had more or less fallen into her lap. He would be a little more difficult. But she relished the challenge and set out to observe him for possible weaknesses.

It took a few weeks, but Mistress Syn began to gather a few useful bits of information. First, he was unmarried- not only were his hands free of any rings, but she'd also heard him talking to a colleague in the halls about his unwanted bachelorhood. That would certainly make things a little easier.

Besides that, she had made sure to note which of her female classmates Professor Daniels seemed to focus his attention on. Even though it was the winter semester, plenty of girls still showed up to class in revealing clothing- herself included, and that allowed her to figure out just what he was into.

Breasts- which didn't surprise her one bit, seeing as she had met very few men who could manage to gaze upon a pair of pretty fun bags and still manage to put a coherent sentence together. Legs- thank you to the girls who thought a skirt was appropriate attire in sub-zero temperatures.

And boots.

That little tidbit had come about not thanks to anyone else, but due to her own offhand decision one morning before class.

She was in a hurry, and rather than dig out something better suited to the weather, Mistress Syn had simply slipped on the closest piece of footwear she had.

This just so happened to be a pair of knee-high black and red leather boots.

Even though her pants- it really was cold out, covered most of them, enough of the shiny leather was still visible- as was Professor Daniel's bulge when she walked past him on her way to her seat. Mistress Syn had noticed the familiar look in his eyes as his mind struggled to return to itself after spotting such a sexy pair of boots, but even when it did, he had unknowingly signed his death warrant.

Oh yes, she had him. Now it was simply a matter of putting this knowledge to good use.

She wasn't stupid- if she acted too quickly he was liable to notice the trap closing in on him and escape. That could not happen. If she were to ensnare him, she needed to move slowly. Set the trap, bait it, then wait for Professor Daniels to fall right into it.

To do that, she made sure to get to class early for the next two weeks. Not only that, but she took a seat as close to the front of the room as she possibly could. And for the cherry on top of the tantalizing toxic sundae that she was, Mistress Syn arrived each day wearing something she was certain to catch his attention.

Every low-cut top that showed off her bountiful bosom was pulled out of her closet. All the skirts and stockings she could slip on to make sure her legs were on full display. And course, as many different pairs of boots as she could get her greedy little hands on.

The first day she did this, Professor Daniels was practically bowled over. He struggled to get through the lesson, although every time his gaze made its way over to her, Mistress Syn feigned ignorance, knowing it would drive him crazy.

The second day, he spent almost the entire class behind his desk, and she was rather certain that was to hide the pronounced erection he was sporting. It took everything she had not to giggle at his obvious discomfort, but she managed. She couldn't let him know she knew the effect she had on him.

By the fifth day, he seemed to have a handle on things, or at least he thought. Mistress Syn had prepared for this and made sure to arrive that morning with enough time to sit directly in front of him, as well as to set a little something up for later. There was no way for him to ignore her, and she made sure that as he stumbled through the day's lesson, her eyes were focused on him the entire time.

She honestly thought he was going to cum in his pants then and there.

When class let out, she remained seated for a moment, then made her way over to his desk. And the moment he saw her, Professor Daniel looked like he was going to have a heart attack.

"Cynthia.... How... How can I help you?"

Mistress Syn smiled her more innocent-looking smile. "I had some questions about next week's midterm... Do you have a few minutes to discuss it?"

In truth she knew his schedule- this was his only class for the day, and usually, he would go to his office afterwards to prepare future lessons. At least, normally. Though she had no proof of it, she was rather certain the last few times he'd gone there his mind had been on something besides classwork.

"I... um..." He stumbled, his eyes clearly trying and failing at not staring directly at her tattoo-covered chest. "I guess..."

"Good," Mistress Syn said with a far more wicked smile. Then she made her way around his desk and got as close as she could without it appearing inappropriate. She wanted to play the innocent student role a little while longer to lull him into a false sense of security.

Once there, she made up something about the midterm- an exam she was already more than prepared for, and watched as Professor Daniel attempted to answer her with some form of clarity. It was clear his focus was somewhere else, and she was enjoying every minute of it. Like a cat with a mouse, toying with her prey a little before going in for the kill.

After a few minutes more, she finally sprung the trap. "Are you alright Professor? You seem a little distracted..."

Looking up from his desk, Professor Daniels's eyes met Mistress Syn's, and the devilish look behind her demonic contacts spoke volumes. He gulped, unsure of what to say or do given the situation, but it wasn't his decision to make. It was hers. And she was about to make it.

"I've noticed you staring the last few days... And at other girls before that..." Mistress Syn began, taking a step away from her instructor so that he could have a better look at all of her.

A black sleeveless v-cut top hung over her shoulders, happily showing just enough of her inked cleavage to get his mind rolling. Tight purple leggings hugged every inch of her strong legs, the sight of them getting his blood flowing in exactly one direction.

And of course, the red and black leather boots that she'd worn the first day he'd truly noticed her.

He didn't stand a chance.

"Like what you see sweetie?" Mistress Syn asked, her voice a little less innocent this time, and she revelled in the fact that Professor Daniels was completely speechless. Good, she didn't need him talking anyway. Trinkets rarely had anything worthwhile to say, especially while she was putting them under her spell.

Taking a few steps forward, she carefully lifted a leg into the air to show it off as well as to plant it, followed by the rest of her, on his desk. Mistress Syn was facing him, and Professor Daniel's eyes were unavoidably focused directly on her chest. "I think you do..."

He gulped, his mind trying to come up with something, anything, which could prevent what was clearly about to happen. Professor Daniel didn't want to get in any trouble, but it was plain to see that trouble was exactly what Cynthia had in mind. And worst of all, he didn't think he could stop her.

The truth was, he couldn't. But Mistress Syn wanted to let him dream for a while.

"I.. This... I can't..."

Mistress Syn smirked. "Can't do what? Can't drink in the sight of a sexy student sitting right in front of you? That hasn't stopped you before..."

She giggled, and he turned red as could be. There really was no way of denying it- Cynthia must have noticed him eyeing her, as well as other students. The fact that she was now using that information against him didn't take away from the obvious truth of the matter.

"Don't worry Trinket," she continued, her tone far more seductive now, "I won't tell... At least, not unless you want me to..."

Professor Daniels's eyes went wide, fear overtaking desire for a moment at her insinuation. "No... please..."

Another smile, this one looking like a predatory ready to pounce upon its prey. "Hmm, I don't know... And I don't think you do either... Here, let me help you focus a little better."

Without warning, Mistress Syn planted her boots onto his chair, both of them nestled there between his legs and the toes of them mere inches from his bulging erection. "I noticed you couldn't keep your eyes off these babies... You like my boots, don't you Trinket?"

Moving them closer, she gently tapped at Professor Daniel's erection with the tips of her boots, and even through his pants he could feel the smooth leather. "Mmm, yes...." he moaned, much to her enjoyment.

"I bet you've jerked your cock thinking about my sexy boots after class, haven't you? Don't you dare lie!"

Her tone shifted in an instant, going from seductive to serious before he had a chance to react. Instinctively, Professor Daniels responded. "Yes!"

Mistress Syn giggled as his face shifted, the realization of what he had just admitted making itself known. "Hmm, such a pathetic little Trinket you are, fantasizing about your students' boots, jerking your cock in reverence to them... Bet you've dreamed about kissing them, haven't you?"

Before he could answer, Mistress Syn moved right right leg off the chair and brought her booted foot to his face. It was level with his mouth, and she slyly pushed the toe of it against his lips.

Without a second thought, Professor Daniels kissed it, and whether he realized it or not, he had just sealed his doom.

"Good Trinket," she cooed, watching as her professor continued to kiss the toe of her boot. "I love watching a man worship my boots...It gets me so wet..."

As she spoke, she moved a hand down towards her legging-covered crotch and slipped it past her waistband. Her pussy was already soaked simply from drawing him deeper into her web. She would be practically drenched by the time she was finished toying with him.

Professor Daniel moaned, opening one eye to watch Mistress Syn play with herself. After a few moments, she pulled the boot away, only to replace it with her glistening fingers. "Mmm, take a good long sniff Trinket... Breathe me in."

He did as she commanded, his eyes closing as the scent of her wetness engulfed him. Fuck, this was wrong, he knew it, but he could not stop himself. Cynthia was weakening his resolve more and more by the minute, and she was only getting started.

Once she was certain he'd gotten a good whiff of her, she slipped off the desk. "Lock the door Trinket. We don't want anyone to interrupt, do we?"

Practically tripping over himself, Professor Daniel rushed from his desk to the classroom door, locked it tightly and headed back to where Cynthia was waiting for him. As he approached her, a part of his mind seemed to realize that he had just shut off his only means of escape, but he didn't care. He wanted- no, needed, to know what this seductress had in store for him.

Once back at his desk, Mistress Syn pointed at his chair with a black-painted fingernail and said "Sit Trinket," suppressing a giggle as her professor did so, already so well-trained. "And take those pants off. You won't be needing them."

Professor Daniels didn't need to be told twice. Within seconds his pants were crumpled up on the floor beside his chair, and he could only watch as Cynthia made her way towards him, plopped into his lap, and wrapped her legs around him like a hungry python.

There was no turning back now. If there ever was.

The sensation of her warm body and slightly damp leggings pressed against him was incredible, and that was nothing compared to her magnificent breasts threatening to engulf his face. He could feel her, smell her, practically taste her, and though it was wrong he didn't care. Cynthia was clearly in control of the situation, and all Professor Daniel could do was follow her lead.

Slowly, she began to rub herself against him, her legs squeezing him and pulling him ever closer to his doom. Mistress Syn allowed his face to graze her chest, denying the prize he so desperately sought. With every movement, she could feel the bulge in his boxers grow larger, and she knew that he was close.

And that just wouldn't do.

"Do you like what I'm doing to you, Professor?" She asked, her tone all business even as her body continued to give him pleasure like never before.

Struggling, he managed to respond. "Yes...."

"Mmm, I bet you'd give anything for me to keep doing this, wouldn't you?"

This was the next stage of her plan- hanging another piece of bait in front of him to see if he would take it. Mistress Syn didn't doubt that he would, but she wanted to be sure before she finished him off completely.

"Yes...." He replied, his eyes torn between her chest and her eyes which were staring directly at him. "Do you... Do you want me to pass you?"

It seemed the obvious answer- that she was doing this to get a passing grade, although that didn't make much sense. Cynthia was already one of the top students in his class, but then, why else would she be doing this?

"Oh no," she said, her tone one of mock shock and indignation that he would think such a thing. "I don't need that kind of help, Professor... In fact, I don't want you easy... I want you hard."

She practically whispered that last word in his ear, her hot breath against his face more than enough to make him melt. Just hearing her say it made his cock grow, and between her words and her movements, he didn't think it was possible for him to get any harder.

But Mistress Syn knew otherwise.

Sliding off him, she pulled his boxers down, allowing his cock to spring out. It was pretty nice all things considered, certainly bigger than her usual Trinkets but still smaller than most of her toys. Even so, it would do.

Dropping to her knees, Mistress Syn brought her lips towards it, drops of glistening precum practically begging to flow free from the tip. As her mouth closed in, her hot breath blew against his aching manhood, but just as it seemed like she was about to slip it inside, she moved away with a giggle.

"Ugh..." Professor Daniel groaned, the momentary denial more than enough to break him even more than he already was. "Please... Please finish me off."

Mistress Syn smirked, then repeated the same wicked dance, getting close to his cock, letting him think she was going to touch it, only to leave him hanging with nothing more than hot air and her cruel laughter. "Aww, what's the matter Trinket? Don't like my 'blowjob' skills?"

She blew another bit of hot air towards his cock, then watched as it flopped around in desperation. Oh yes, she most certainly had him now.

Standing up once more, she plopped back down onto his lap, this time with her back facing him, and her legging-covered ass practically crushed his erection. Professor Daniel cried out, a mix of pleasure and pain coursing through him as she popped up then down again, bouncing her ass up and down on his cock over and over.

Somehow he grew even harder beneath her. His manhood was pulsating with desire, aching for her and everything she could offer him. All she had to do was make sure he could offer something else in return.

"Do you want this Trinket?" Mistress Syn whispered, spinning around and straddling him once more, her eyes locked on his, the sight of the sheer desperation and desire in them making her even wetter than before.

"Yes," Professor Daniel sputtered, any rational thought he may have had long since passed, crushed beneath the weight of his student seductress.

"What'll you give me to let you cum?" She asked, her face momentarily turning into a mockery of an innocent puppy dog look that belayed her nefarious intentions.

Professor Daniels struggled, both physically and mentally, but knew she wouldn't wait for an answer. So he said the only thing he could think of. The truth, even if he wasn't completely aware of it yet. "Anything you want."

There it was. Music to her ears.

"Anything you want Mistress Syn."

She waited a moment to see if he would catch her drift, if he would fully embrace his newfound reality and what it entailed. Only then would she know for sure that the trap had indeed sprung and captured him hook, line and sinker.

Gazing up at her, eyes filled with tears of need and longing and more than a little submission, her professor spoke five words that held more power than a thousand others could ever hope to. "Anything you want Mistress Syn."

The moment he said it, she knew she had him. And while she would normally leave him hanging, his cock was far too good to waste. But that didn't mean he would truly enjoy it.

Rising off of him, Mistress Syn returned to his desk and moved her boots so they rested right in front of his cock. "Show me. Show me how you jerked off thinking of me and my sexy boots every day after class. Show me just how much you want to be my pathetic little Trinket."

Taking hold of his cock, Professor Daniels immediately began to stroke it, his hands a blur as they slid along, spurred onward by the precum he had spilled as well as a need to do as she had commanded. He wanted to show Mistress Syn just how badly he wanted her and her boots.

It only took three minutes. Three minutes of jerking, three minutes of staring at her and her boots, three minutes of absolute submission towards her, for his cock to explode. And when it did, streams of hot cum shot out and right onto Mistress Syn's waiting boots.

Professor Daniels kept stroking, almost unable to stop, his eyes nearly rolling back into his head as the orgasm she had teased out of him made its presence known. He swore every single drop of cum in his body had been expelled, yet even then he did not stop stroking until his arms seemingly lost all strength.

And when they did, he opened his eyes, just in time to see Mistress Syn recording every second on her phone. She smiled as realization and regret filled his face, but if he thought that was the worst of it, he was dead wrong.

"Don't worry Trinket, I made sure to bring in one of my cameras before class. I recorded everything. I just wanted a nice closeup of you cumming all over my boots."

Her professor groaned in despair, the full scope of everything sinking in. She might not have wanted him to pass her, but she did want anything and everything else he could offer. And now she had the means to get it.

But still, she wasn't finished with him.

Lifting her legs, Mistress Syn presented her now glistening boots of him, his eyes taking in the sight of all his cum. "Clean these up Trinket. I don't want to walk back to my dorm with a drop of your pathetic loser load on them."

With a sigh, he leaned over and began to lick her boots, the mix of sweet leather and salty cum filling his mouth with every pass of his tongue. All the while, Mistress Syn kept on filming, much to his chagrin. Then again, there was nothing he could do about it.