Sinful Tutoring: Final Lesson

This chapter legit would not exist (much like the rest of the series but more so) without Synful Mistress/Mistress Everlynn as she helped me come up with the idea for this one. If you haven't already, check her out.

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The semester was drawing to a close. Final exams had come and gone, and I'd somehow managed to pass all my classes. I should have been pleased, and had my situation been closer to what it had been at the start of the semester, I likely would have. Unfortunately, so much had changed since then, and not for the better.

My bank account was at the lowest it had been in some time, and not due to any change in my working hours or an increase in my usual expenses. Rather, all of it had instead gone to pay Mistress Syn for her various 'lessons', as well as to keep her from releasing any of the countless pictures and videos she'd taken since our first meeting.

Beyond that, I was at a personal low point, having been regularly humiliated and degraded by both her and Jane, to the point that I'd been sporting a chastity cage for several weeks and hadn't had the opportunity to cum in even longer. I was desperate for release, no matter the cost.

My cock was proof of that.

Though it remained locked up tight, it was constantly poking at the sides of its cage thanks to countless hours spent watching and re-watching all those same videos. My 'homework' for the times in which Mistress Syn was too busy with schoolwork or Jane to teach me a lesson in person.

And worst of all, worse than nearly anything else, was the undeniable fact that after months of this treatment, I was beginning to like it.

Much as I'd like to claim it was due to the attention- twisted as it was, of two gorgeous women, I could no longer shake the realization that it was more than that. I liked what they did to me. I liked being tormented and teased by Mistress Syn over and over. Relieving every incident likely didn't help matters, but then, that was the point. The more I watched our lessons, the more my cock grew to associate those things with pleasure.

Even if they were things I would have never deemed pleasurable in the past. Mistress Syn had completely and utterly reprogrammed me to the point that I yearned for her lessons. Which made it all the worse that I hadn't had one since our evening in the nursing department. I'd left that lesson so horny from the prostate milking that the moment I started up the USB my cock was dripping precum, and I groaned with desire with each new video.

Mistress Syn had warned me that, with finals coming, it was highly unlikely we would have another lesson, hence why I'd been commanded to do my 'homework' five times a day. Even so, I'd barely spotted her or Jane around campus, although when I did neither one as much as gave me the time of day, which made me feel even lower than I already did.

The few times I had seen them though, was more than enough to get my cock up and yearning, especially whenever I spotted the key hanging around Mistress Syn's neck. The key to my cage, my salvation, and my submission.

So it was that as the last few days of school began to taper off, I found myself regularly sitting in my dorm packing for the summer as well as wondering just what would happen next. Would I be given a lesson before the semester ended, or would I be denied even that? Would Mistress Syn at least unlock my cage before I headed home?

I didn't know, but I certainly hoped so.

As I finished up yet another box, my phone buzzed, and I immediately perked up at the thought that it would be Mistress Syn. It was, and her message, brief as it was, sent shivers down my spine.

"Miss me Trinket? I bet you do... I think it's time for your final lesson. Tomorrow, my dorm. Noon. Bring the biggest tribute you can. XOX."

I read and re-read her message countless times, my find fixated on the word 'final'. It was at that moment I recalled that Mistress Syn wasn't simply finished for the semester- she was finished up at this school. Unless by some figment of the imagination she'd failed one of her finals- something I highly doubted, she would be gone from my life in a matter of days.

And that filled me with a myriad of emotions.

On the one hand, with her gone, the fear of her releasing any of the videos and pictures seemed to lessen, as she wouldn't have much reason to do so. On the other, the fact that she would be gone for good meant our lessons would be done with, for better or worse.

As much as I'd grown to enjoy them- and I had, in a twisted and depraved sort of way, I didn't mind the fact that perhaps I could at long last return to a less humiliating life... But then, without Mistress Syn around to toy with me and tease me, what kind of life would that be? I longed for her control more and more every day and wasn't sure how I could go on without it.

Even so, I was more concerned with what her departure and my 'final' lesson meant for the cage locked around my cock. Would she remove it for good, or simply take the key with her when she left as a final, brutal humiliation? I didn't know for sure, all I knew was tomorrow, I would have my final lesson with my twisted, teasing tutor.

And I couldn't wait.

I finished up packing as much as I could, my mind awash with questions and desires, then I loaded up the USB for the fifth time that day. And as I sat there revisiting all my humiliations, my cock began to grow and leak while the rest of me shivered and groaned. What did she have in store for me? What could she possibly have left in that wicked mind of hers after everything else she had put me through?

And what would happen to me when all was said and done?

The next morning, I woke up bright and early and with morning wood practically glued to the sides of my cage. All night, my dreams had been filled with endless visions of Mistress Syn, and the horniness which had lingered ever since our last lessons only grew as I slipped the USB back into my laptop, intending to get as much 'homework' done before my final lesson as possible.

A little ways before noon, I finished up my third run-through of everything and headed out, making what I hoped would be my final stop at the campus ATM for such an occasion. I withdrew nearly one thousand dollars- almost all I had left, then made my way towards Mistress Syn's dorm. It all came down to this, and I was as ready as I'd ever be.

I knocked on her door at five to noon and waited nervously, shivering with anticipation. She kept me in suspense the whole time, only opening the door at exactly twelve 'o'clock, and once she did, my heart nearly stopped beating in my chest.

Mistress Syn looked amazing as always, her makeup on point and suitably demonic, and her choice of attire as fitting as could be. She wore her black leather corset, the zipper halfway down so as to show off her tits, a pair of purple fishnets snaking their way across her incredible legs, and a pair of black and red knee-high leather boots that practically begged to be worshipped.

My face must have betrayed my feelings seeing as Mistress Syn smiled wickedly before stepping back and allowing me inside.

Once there, she shut the door behind us and I immediately dropped to the floor, stripping off my clothes as she watched. "Very good Trinket. You've learned SO MUCH under my tutelage."

The moment I'd stripped off the last article of clothing, I pulled the money I'd taken out from the pocket of my shorts and handed it to her, head hung low in fear that it somehow wouldn't be enough. She took it, and a moment later, a black-painted fingernail slid under my chin and brought my face up to look at her.

A sweet smile spread all across Mistress Syn's glossy red lips. "I'm impressed Trinket. I really am. No one else brought along one this big."

I pondered her words as she walked over to the counter and placed the money aside. They didn't make sense to me, but at this point, I was so desperate for her that I scarcely had any brain cells left to think of anything while in Mistress Syn's presence. I simply wanted her to teach me my final lesson.

Picking up a collar and leash from the counter, Mistress Syn walked back over to me and clasped the former around my neck before leading me from her front door down the hall towards her bedroom. And though I'd been there countless times before, I still found myself taken aback when I crossed the threshold.

Especially this time.

The room was partially boxed up already, with a fair amount of Mistress Syn's toys and tools no longer out on display. More than that, there was a distinct lack of Jane this time around, and I considered that perhaps she simply wasn't needed for this particular lesson. I didn't know for sure and dared not ask.

Mistress Syn led me inside her room and shut the door behind her, then pulled me towards the bed, the leash held tightly in her hand the whole way. Once there, she gazed down at me with that familiar wicked look plastered all over her face and smirked. "Looks like your little dicklet is excited for your lesson... Have you been doing your homework Trinket?"

Looking down, I could see drops of precum on the floor, and I sighed. "Yes, Mistress Syn," I replied truthfully. "Five times a day as you ordered."

"Hmm, even today?" She asked.

"No... I only managed to do it three times today... I'm sorry Mistress."

I honestly felt regretful and worried that I was in trouble. For a moment she looked disappointed, but after a second she shrugged. "It's okay. As long as you boned up for your final, that's what matters. Especially for this particular lesson."

Relief washed over me for a second, only to be just as quickly replaced by curiosity. What did my 'homework' have to do with my final lesson?

Mistress Syn quickly explained.

"Consider this a final exam... A way to prove you really learned your lessons... And like any good final exam, it's cumulative. You're gonna get to do it all over again! Doesn't that sound fun Trinket?"

My eyes widened as I wondered just what she meant by 'all', but before I could even think to ask, she took a seat on the bed and plopped her boots

on the floor right in front of me. "Exam starts now."

Without a second thought, I dropped to the floor and began kissing her boots.

The instant my lips touched the dirty, well-worn leather, I was taken back to our earliest lesson, when she'd had to force me to do such a thing. Here I was now doing it without question, and enjoying it. She really had me well-trained, and now she was making sure of it.

Once I'd showered the toes of her boots in kisses, my tongue slipped out and I began licking them as well, running it along the toe of her left one and lapping up all the dust and dirt that had accumulated on it.

Where once upon a time I'd have found such an act disgusting, thanks to Mistress Syn's countless lessons, now it seemed only right to worship her boots in such a way. She deserved only clean, spotless boots, and I would gladly make sure that's what she got, one way or another.

Finishing with the toe of her left boot, I made my way up and along the shaft, moving my tongue in between the laces and holes and making sure I didn't miss a single spot. Every speck of dust, every piece of dirt, every unknown trace of something or other, I licked it up with impunity.

When I was certain I'd got it all, I moved down and attempted to lick her heel as best as I could. Mistress Syn lifted her boot slightly as I did, allowing me to get both it and the sole with my tongue even though I practically had to rest my head on the floor to do so. I licked at every inch of leather, making sure to be as thorough as possible.

Only then did I dare move on to her right boot.

I gave that one the same treatment as the left, cleaning the toe, shaft, heel and sole as best I could until it, like its twin, shined like new in the dim light of Mistress Syn's bedroom. And once I was finished- once I was certain I'd gotten every bit of dirt and dust off on them and into my pathetic whore mouth, I made sure to plant another kiss on the toe of each boot in reverence before gazing up at Mistress Syn.

She looked impressed. But she didn't say a word.

Instead, she undid the laces of each one and slipped off her boots, placing them to the side and presenting her fishnet-covered feet to me in their place.

The moment they left the confines of her boots behind, the smell of her feet hit me like a ton of bricks, bringing me right back to our first lesson. Even without saying anything, it was crystal clear to me that Mistress Syn had been wearing those boots for quite some time in preparation for this final lesson of mine.

Sweat glistened in the fairy lights of her room, and the smell only grew as it permeated the air around me. And yet, much as it should have turned me off as it once had, I found that now I didn't mind it so much... In fact, as it made its way into my nose my cock started to strain against the chastity cage even more than it already was.

I groaned in discomfort but pushed it aside before diving at her feet without question.

My tongue lapped at the sole of her right foot, licking up all the sweat and dirt that covered it, dipping in between the holes of her fishnets to make sure I got every spot. I drank in the scent of her stinky feet as it washed over me more and more, my cock leaking desperately as my mind surrendered to its desire for such a depraved and disgusting thing.

The sole taken care of, I made my way to her black-painted toes, taking each one in my mouth and sucking them as if they were the sweetest treat in the world- and in that moment, they were. My taste buds wept beneath the assault of foot sweat and toe jam, but I didn't care, worshipping Mistress Syn's toes one by one and licking in between them along the way.

Her left foot received the same treatment, the smell and taste of it driving me wild even as my mind and body were torn between disgust and delight. Having been denied even the smallest crumb of attention from my Mistress for so long made me want nothing more than to take everything she gave me.

And I would.

Happily.

When I was certain I was finished with her feet, I stopped, and Mistress Syn looked them over. She nodded but still did not say a word, denying me even the teasing taunts I'd grown accustomed to. Instead, she stood up and pointed at the spot between her legs on the bed, and immediately, I knew what was expected of me. As well as what lesson we were about to repeat.

I crawled closer and laid my head on the bed, staring up at her perfect, fishnet and panty-covered ass as she slowly brought it down onto my waiting face.

Unlike during our second lesson, I made sure to take a sizable breath beforehand, although once the full weight of her touched down I knew it wouldn't be of much use. My nose was immediately filled with the smell of her sweaty, panty-clad ass, and her cheeks pressed against my lips, practically swallowing my face between them.

My cock continued to strain against its cage, leaking copious amounts of built-up precum even as my lungs began to burn from the strain of holding my breath. Even so, I did not yield- Mistress Syn wanted to smother me with her ass, and I was going to let her do so for as long as she wished.

Sitting there, my mind jumped back to our second lesson. The exact moment she had proven just how much of a pathetic whore I was for her and her feet and her ass already. That was the moment everything had truly changed. When I had truly become hers.

And she was proving her ownership of me once again.

The breath I'd taken finally burst out, and my mouth was quickly filled with the ass sweat she'd built up. Between it and the smell and the lack of air, I was growing more and more light-headed by the second, but still, I refused to struggle or give up. I wanted- no, needed, to prove myself to Mistress Syn.

Just when I thought I couldn't hold out any longer, when I thought I would pass out, Mistress Syn stood up, and I gasped for air even as she looked down at me with a small smile. Again, she remained strangely silent, which I wasn't sure was a good thing or a bad thing.

Once I was able to breathe normally again, she picked up my leash and led me toward the end of her bed, a familiar spot for me. I looked around nervously, unsure if she had any of her tools around, but it did not appear that a punishment was in the cards for me. Which left only one other option.

Mistress Syn cuffed my hands to the bed as she had before, then let go of the leash and walked over to her dresser.

Where a familiar strap-on waited.

She slipped on the harness and gave the rubber cock a teasing stroke before making her way back over to the end of the bed. I heard the sound of something squirting and, a moment later, felt the cool sensation of a lubed-up cock slipping into my waiting ass.

Slowly, Mistress Syn slid the strap-on in a little bit at a time, toying with me every step of the way. Unlike when she and Jane had spit-roasted me, she was taking her good sweet time. The rubber cock simply slid in and out, keeping me on edge waiting for the eventual shove of its entire length.

After a few moments teasing, Mistress Syn pushed the cock deep inside, the tip of it practically tapping my prostate before she pulled it halfway out and pushed it back in again. In and out, keeping a steady tempo, the slick, cool rubber fucking me as I lay there taking it.

No tears filled my eyes this time, no despair. In its place, a sort of serenity. I was enjoying getting my ass fucked by Mistress Syn, and that in and of itself was disturbing. I'd fallen so far into depravity that even an act like this, something that would have turned me off completely before, now felt right.

My cock certainly agreed. It refused to soften or to stop dribbling out precum inside the cage.

The thrusts slowly increased in speed and frequency, Mistress Syn's cock beginning to truly fuck my ass for all it was worth. Her hands gripped my hips for support as she pushed all the way in and pulled nearly all the way out, leaving only the tip in my asshole before doing it again and again,

A moan escaped my lips, one of pure, twisted enjoyment, and the moment it did, I felt her pull out completely and tap my cheeks with the tip of her cock. Then Mistress Syn walked over and undid my restraints, still eerily silent.

Taking hold of my leash once more, she pulled me further onto the bed, pushing me onto my back, and tying my hands to the head of it, leaving my legs free. However, I knew she wasn't quite finished with me, seeing as she hadn't yet removed the harness or the strap-on.

What she did do, to my shock and amazement, was slip the key off her neck.

I watched as Mistress Syn took hold of my cage and unlocked it, then slid it off my aching cock and placed it on her dresser. My precum-encrusted erection sprung free and saluted her, and though she didn't say a word, a wicked smile took over her lips. She was quite pleased to see such submission and I was happy to offer it.

"You've done so well Trinket," she finally said, breaking the silence. "You've learned so much from your Mistress, haven't you?"

"Yes, Mistress Syn," I replied, still in shock at being freed from the cage and honestly willing to say anything to keep it that way.

"Good boy... I guess it's time I let you cum for real."

My eyes widened at the sound of that. I almost didn't believe my ears but quickly realized I'd heard her say it.

I watched her walk back over to the dresser, where a box of latex gloves waited. Mistress Syn slipped on a pair of purple ones and snapped them on, my cock snapping at attention along with them, much to her amusement. Then she returned to the end of the bed, lifted my legs up, and slid the strap-on back inside my ass.