Sinful Tutoring Next Semester

So right before I finished off Sinful Tutoring, I came up with this title and knew I'd have to do something with it. And after a little while, I figured out what. Unlike the previous story, rather that a single sub, this story will follow Syn as she toys with several new subs at her new school.

As with the previous story however, this wouldn't exist without the amazing content of the lovely Synful Mistress/Mistress Everlynn/Synful420B. If you like these stories you'll love her.

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She'd barely finished unpacking when it happened. A new record as far as she was concerned.

Cynthia May- aka Mistress Syn to countless drained and enslaved men back at her old school, had arrived at the dorms of the top medical school in the state earlier that late August morning and most of her things were unpacked and put away by mid-afternoon.

Her new room was a far cry from the one she'd had back in College, but she knew in time this one would feel just like home as well.

Especially once she got all her new toys.

While it was true that she'd left behind more than a few as gifts for her unexpected 'apprentice' Jane, the money she'd blackmailed out of her various Trinkets over her academic career had been more than enough to find some to take their place. Some were still in transit, some she was still finding suitable replacements for, but sooner or later, Cynthia would have everything she'd need to start having some real fun here.

That being said, classes didn't start for a few days, and with the unpacking part over and done with, she decided to relax a little bit.

Which involved stripping off her clothes- everything drenched in sweat from carrying in, moving around, and opening box after box in the late summer heat, and laying down on her bed wearing nothing more than a set of shiny purple lingerie. Another purchase provided by her very generous Trinkets.

Then she dug out her favourite wand, flicked it on, and within seconds, the familiar buzz began to echo out in the small bedroom. Cynthia pulled her panties to the side so as to allow the toy to make contact with her pierced, and already slightly damp, pussy.

The moment it did, a small moan slipped out from her painted lips, and the stress and soreness of the day slowly melted away underneath a veritable wave of pleasure.

A wave which was quickly broken by the sound of unexpected footsteps and an unfamiliar voice.

"Sorry to bother you but your door was open and-"

Within seconds the voice stopped in its tracks, and in its place was a young man standing in the doorway with wide eyes and a jaw nearly on the floor.

Cynthia looked up in shock and quickly put the wand to the side before allowing her panties to slip back over her pussy once more even as she took in the sight of the stranger standing before her.

The tag on his polo shirt read 'Shawn. Floor Supervisor,' although he seemed a little young for such an important position. In fact, he not only looked like he'd started that very day, but that he was fresh off the bus from somewhere far away from here.

Somewhere where they clearly didn't have women that looked like her.

Shawn's eyes were glued to Cynthia, to her tattoo-covered body, incredible chest and magnificent curves, accentuated by the purple lingerie she was wearing. In any other situation, coming upon someone like her in such a position would have been a dream come true.

But in this one? He was clearly in over his head.

"What the fuck?" Cynthia practically screamed, glaring up at the young man and making him step back in fear even as his face remained frozen in place from the unexpected sight he'd stumbled upon. "What, do you just go around barging into people's rooms or something???"

"I... I... um..." Shawn struggled to speak, his eyes refusing to leave the body of the nearly naked woman before him. He knew he should say something, anything, to defend himself, but the words simply refused to come. Granted, given she was dressed in her underwear, it was difficult to blame him for that.

But Cynthia certainly did.

"You what?" She continued, rising off the bed and staring him dead in the face, her demonic makeup only adding to the fear Shawn was already filled with. "Thought you could get a free show or something you pathetic little shit??"

Shawn gulped, truly terrified of Cynthia. She wasn't anything like the girls he'd known back home, and regardless of why he was actually there, it didn't seem to matter what he answered. She had clearly made up her mind on the situation, and anything he said would only make things worse.

And yet, he still tried.

"I'm sorry," Shaw began, stammering beneath her intense gaze. "It's just... I was checking which rooms were already occupied, and your door was open so-"

"So you decided to be a creep?"

Cynthia was standing right in front of him, and though he was an inch or two taller than her, at that moment Shawn honestly felt two feet tall. He wanted to defend himself further, but there didn't seem to be anything he could say. Which made what happened next all the worse, although he had no idea just how much worse things could get.

Once she'd finished asking her, more or less rhetorical, question, Cynthia's eyes moved down and quickly noted the bulge the young man was pitching in the crotch of his shorts. And the moment she spotted that, a familiar wicked idea sprouted in her already cruel mind.

Just because school hadn't officially started didn't mean she couldn't start giving out a few lessons.

Lessons Shawn was clearly in need of.

"Get on your fucking knees," Cynthia commanded, and the young man's eyes seemed to only grow wider with shock and surprise at that unexpected order.

When he didn't do what she'd said right away, Cynthia grabbed the collar of his polo shirt and pulled him down until he was on the floor in front of her. "You have a lot to learn bitch... Lucky for you, I'm a great teacher."

Dropping back onto the bed behind her, Syn held up her feet and presented them to the still-shocked Shawn. "Kiss my feet. Now!"

Shawn stared at the feet in front of him, and almost immediately, the smell of sweat made its way deep into his nose. Cynthia's feet reeked, and her soles were covered in bits of dust and dirt from a morning spent unpacking her things barefoot. But she didn't care and shoved her soles towards him to reinforce her command.

"I'm not gonna tell you again bitch. Kiss. My. Feet!"

With a gulp, Shawn leaned forward and pressed his lips to her filthy sole. The taste of dirt, dust and sweat invaded his mouth as the smell continued to wash over him. It was downright disgusting, but if he thought a single kiss would be enough to placate the wicked woman before him, he was dead wrong.

Cynthia kept her feet in front of him, pushing them closer until they were practically pressed against his face, and with a sigh, Shawn slowly began showering both soles with small kisses.

Smiling evilly, Cynthia reached for her phone and, without a word, began filming, making sure to get several good shots of Shawn's face and name tag even as he kissed her filthy feet and nasty toes like his life depended on it. He didn't know it yet, but it did.

"That's right, kiss every inch of them. Show me how bad you feel for barging in on me like a little fuckin' pervert."

Though he dared not say anything, Shaw did feel quite bad. Not simply for what he'd done- accidentally or not, but for what he was currently doing. Kissing a stranger's dirty feet made him feel downright awful, yet he dared not stop. The fear Cynthia had already instilled in him made damn sure he kept at it until she told him to stop.

Which she would.

Eventually.

But not yet.

Not when that bulge she'd spotted in his shorts only continued to grow.

Shawn had felt it, the sensation of his erection rubbing against his boxers only adding to his despair and embarrassment. He was getting hard from this. Or at least being so close to such a gorgeous, scantily-clad woman as Cynthia. It was honestly hard to tell, and he didn't want to think about it.

"Oh. My. God!" Cynthia exclaimed in mock surprise as she pulled her feet away for a moment. "Is your dick getting hard? Fuck, you really are a pathetic little pervert!"

Looking down, Shawn noted the bulge he'd honestly hoped had all been in his imagination, as well as the spots of precum starting to make themselves known against the dark fabric of his shorts. It was actually happening, and worse than that, she knew it. "Umm...."

"Shut the fuck up and pull down your pants," she commanded, and this time, Shawn did exactly as he was told. Within seconds, his shorts and boxers were touching the floor of her bedroom and his cock was standing at attention, erect and leaking. Cynthia smiled. "Start stroking that little dicklet and suck my toes."

She shoved her feet back in his face, making sure one of them penetrated his mouth. The look of utter disgust on his face made her wet, even more so when she watched his hand wrap around his cock and start slowly stroking it, the pleasure of such an act barely registering thanks to the taste of her toe jam and sweat filling his mouth.

"That's it bitch. Suck my dirty little toes like the whore you are... And don't you dare stop stroking that dicklet until I say so."

With one hand still filming Shawn, Cynthia picked up her wand and held it to her panty-covered pussy, getting back into the thick of things even as he continued to masturbate and suck her toes. It'd been far too long since she'd dominated anyone like this, she'd almost forgotten how good it felt.

The sound of the buzzing wand rung out, and as much as Shawn wanted to look up and watch Cynthia get herself off, the taste of her toes in his mouth, as well as the sole pressing against his face and slathering it with more dirt and sweat, kept his attention clearly focused on the task at hand.

As did the continued stroking of his erection.

It felt good- and more than a little risque, doing so in the presence of such a stunning woman as Cynthia, but it was also tempered by the utter depravity of everything else going on. This was clearly wrong, but there was nothing he could do about it save follow the orders he'd been given.

Cynthia kept filming, making sure she got plenty of footage of the man masturbating as well as him sucking her toes for all they were worth. He hadn't noticed her phone yet, and that made it all the sweeter. She even managed to switch feet around without interrupting her own fun, wanting him to clean all her toes before she even considered telling him to stop.

Shawn's hand was moving faster now, gliding along the precum-covered shaft, up and down his cock even as the taste and smell of her feet overtook his senses. Cynthia could feel his breathing getting heavier and heavier even with her foot in his mouth and knew he was getting close.

Good. Time for his first lesson.

"Mmm, you're so close, aren't you? So fuckin' close to blowing your pathetic load for me and my nasty feet... STOP!"

The moment she said those words, Cynthia pulled her foot free from his mouth, and Shawn gagged in surprise and joy, the latter quickly changing to sorrow as he let go of his aching cock and could only watch as precum continued to dribble out even as not pleasure came with it. A groan escaped his lips at the loss of any orgasm, but that was nothing compared to the feeling that overtook him when he at long last looked up and noticed the camera in her shaking hand.

"Aww...." Cynthia managed to say in between moans as the wand dragged an orgasm out of her and her panties became drenched in her juices. "Poor baby... But that's what you get for walking in on someone like that..."

Her moans mixed with a wicked laugh as she stopped recording, making sure to get a final shot of Shawn's face as the realization of what she'd done fully sunk into his foot-addled brain. "Hmm... school hasn't even started yet, and I bet if I showed this video around, it wouldn't look too good for you. I mean, a Dorm Supervisor sucking a new student's dirty toes and jerking off at the same time. That'd be downright humiliating, wouldn't it?"

Shawn nodded, his eyes practically filling with tears and his mouth unable to speak. Humiliating wasn't the word. He would be in deep trouble if that footage got out, regardless of how events had begun. After all, it would be her word against his, and he had walked into her room unannounced...

It was bad. No two ways about it.

But it was about to get worse.

"So, here's how it going to be, Trinket," she continued, looking down at him with a truly evil smile on her face. "If you don't want anyone to see that little video, it's going to cost you. A lot."

He gulped and waited for more, but it seemed that was the extent of her threat. Shawn could only nod as he pulled up his boxers and shorts, and once he did, he stood up and turned to leave the room with his head hung low in shame and embarrassment. But before he left her bedroom, he looked back and asked the only question he could think of.

"Who are you?"

Cynthia smiled evilly.

"You can call me Mistress Syn..."

And he would.

As would many others soon enough...