Sinful Tutoring Next Semester Pt 06

This is actually the epilogue for both Sinful Tutoring Next Semester and the original Sinful Tutoring, but there's not enough space in the title to put Epilogue so I just wrote part 6. Even so, this is where things come to their (current) end. Hope you've enjoyed both this and the original series!

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"After that, things were pretty boring," Mistress Syn uttered lazily as I lay on the floor of her office, naked save for my new chastity cage, her bare, dirty feet resting on my face. "Although poor Dean Winslow probably wished he'd just left things well enough alone..."

Once I'd started officially working for the company, she and I had quickly gotten into a routine not unlike the one we'd had back in school. Whenever the urge took her, Mistress Syn would schedule an 'appointment' for me, and I would make my way to her office, head hung low in shame, and accept whatever humiliation or punishment she had in mind for me that day.

Some days, she would simply have me lick her boots or feet clean. Others she would bend me over her desk and fuck my ass with one of her many strap-ons. If she were in a bad mood for whatever reason, she would take it out of me with her cane or her whip or countless other new tools she'd picked up over the years.

Once in a while, she would make me come and see her after she'd finished up a workout at the company gym, then plop herself down on my face and force me to huff the scent of her sweaty ass until I was ready to pass out... Only to let me breathe for a few moments before doing it again.

Time had passed, but it had not made Mistress Syn any less wicked.

It didn't take me very long to come to the sobering realization that, just like back in school, I was not the only person she had under her thumb. In fact, nearly everyone of any importance in the company was one of Mistress Syn's Trinkets. I'd even watched the CEO exit her office one afternoon while I waited for my appointment, his face red with embarrassment and the unmistakable trace of dust and dirt from her boots on his lips. Neither of us said a word to one another, but the truth was abundantly clear.

That was when I knew for certain that I was really and truly fucked. There was simply no way of getting out from beneath her heel.

And yet, perhaps out of morbid curiosity, I still found myself driven to ask her how it was she'd gotten into such a position.

I thought she would berate me for asking such a thing, but oddly enough, Mistress Syn kindly told me all about it. Her tale took several appointments of course, but she made quite certain that I knew every single sordid little detail of her time in medical school.

From the humiliations she'd bestowed on her fellow students to the ones she'd brought about on the staff and even the Dean, all of them were quite familiar to me. I'd endured the very same ones in the past, as well as since I'd returned to my place at her feet.

Simply knowing what she had done- had continued to do, was further proof of just how weak I and countless others were. As well as how powerful Mistress Syn could truly be.

"Still, between my grades and having such important people in the palm of my hand, I had my pick of jobs when graduation came around- top of my class by the way Trinket," she added with a smile as she wiped her soles back and forth across my face. "It just so happened that one of my former Trinkets from College worked here... He was so very gracious, helped me get my foot in the door, as well in other places, and the rest is history."

I groaned as I ran my tongue across her dirt-covered soles, the taste of sweat, filth and boot leather as familiar to me now as it had been during our original time together. Even so, as I continued to worship her, another question made itself known. "Mistress, if I may ask... Why stay as the company doctor?"

It seemed to me a fair question, or so I thought. With so much raw power at her fingertips, she could easily usurp a member of the board or even the CEO's position, and no one would truly be able to question it without facing rather harsh consequences.

Moving her feet off my feet for a moment, she gazed down at me with those demonic-looking eyes of hers. Mistress Syn always made sure to wear those contacts whenever she and I had our 'appointments', and they were a constant reminder of her inherent wickedness.

"Silly Trinket... I didn't go through medical school all those years just to sit in some stuffy board room. I do enjoy making people feel better...."

She smirked, slipping the toes of her right foot into my mouth. Disgusting as they were, I sucked on them like my life depended on it- because I knew in my heart that it did. "Besides," she continued, moving her other foot back up to cover my face. "I love my job. Especially the benefits..."

Much as it pained me to admit, I couldn't quite blame her. I didn't know if her 'deals' with the other employees were the same as mine, but if they were....

Mistress Syn was already taking a fairly decent-sized cut of my pay to keep her ever-growing collection of pictures and videos from leaking. If she were getting the same from everyone else, on top of her own substantial salary... Well, that would certainly qualify as worthwhile benefits.

I returned my attention to her toes and soles, sucking, licking, sniffing and worshipping them while she watched, occasionally snapping fresh pictures to add to the veritable treasure trove of them she had of me alone.

Sometimes, when our appointments were over with, she'd send me back to work with a USB full of them some dating back to our College days, and just like back then tell me to watch them over and over while my pathetic little cock ached in its cage. Other times she would tease me with the contents, reminding me of all the things she'd made me do even as I prepared myself to leave her presence once more.

There was seemingly no end to her cruelty. But that wasn't the worst part.

Nor was the being constantly teased and denied while locked up tight, or paying again and again and again to keep my growing discretions hidden from the world at large. Those were all rough it was true, but they were nothing new to me.

Even hearing her talk about some of her other appointments while she fucked my mouth or my ass or caned the latter until it was so red I could barely sit down at my desk afterwards, although those were far from fun.

No, the worst part was a piece of information she had happily provided fairly early on in our newfound business relationship.

The knowledge that, when all was said and done, when the working day was over and done with and Mistress Syn had thoroughly humiliated, punished, and rinsed me and countless other men and women in the company, she would head home, safe in the knowledge that we were all locked up tight, and fuck her husband for all he was worth.

Mistress Syn had shown me a picture of him one afternoon, and while he appeared rather average-looking man with a bit of a dad bod, it was quite clear that she and he had a relationship I and many others could only dream of.

"He willingly gave me his submission Trinket," she whispered while preparing to give me a 'company-mandated prostate exam'. "And when he slides his big cock in between my feet or my tits or sticks it in my ass or my pussy, I tell him all about you and the other pathetic little slaves who wish they were in his place."

I groaned then as I do now whenever I think about it, about the two of them lost in each other's embrace. Knowing that someone out there was lucky enough to truly belong to her. To submit to her on a level well above my own. Someone who knows all about us, and who thrives off that knowledge. That is what breaks me time and time again.

He learned his lesson early on. One I and others will likely never stop learning.

It's Mistress Syns world.

We're just living in it.