Sinful Tutoring: Lesson Eight

If you haven't checked out the amazing lady who continues to inspire this story (Synful Mistress) you are missing out. She is awesome, and well worth a look.

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The rest of that night and the following days were nothing sort of pure, unadulterated agony, and not for the reasons I'd originally expected.

Which wasn't to say the residual pain in my backside from Jane and Mistress Syn's dual assault on my bare behind, let alone the thorough fucking I'd been given at both ends, although those seemed to linger far longer than the original punishment I'd received had. But rather, the lesson that Mistress Syn had sent me home with did most of the damage.

Once I got back to my dorm, I cleaned myself up, eyeing the chastity cage locked around my cock as I did, then plugged the USB into my laptop. Slipping on my headphones, I proceeded to watch the contents of the drive, and though I thought I'd known what to expect in doing so, I was dead wrong.

You see, during my walk home, I'd foolishly tried to convince myself that revisiting the history of my humiliation at Mistress Syn's hands wouldn't be so bad. That perhaps I could separate myself from the truth of my situation, and likewise convince myself that the pathetic specimen I'd soon see on my screen was not me.

I quickly realized how futile a gesture that was.

There was simply no way to ignore the cold hard truth of the matter as it presented itself on my laptop screen. Mistress Syn had broken me in more ways than one, and all I could do was bear witness to just how thoroughly she had done so.

The drive began with a slideshow of pictures from our very first lesson, with Mistress Syn's smelly, sweat-drenched shoved in my face, and me there naked and hard getting hard from it. These were followed by screenshots taken from the various videos which were sure to follow, and seeing them all again made me feel as low as I thought I could ever feel.

But then the videos started.

The playlist which followed the slideshow was longer than I'd anticipated, and I saw that Mistress Syn had indeed documented each and every lesson we'd had.

I watched myself get smothered by her feet and ass, be teased by her soles and punished by her toys. Watched as I cleaned her dorm from top to bottom in that sissy maid outfit- an outfit I needed to pick up whenever I dropped off her sheets to be cleaned. Drank in my continued humiliation over and over.

And all the while, much as I wished otherwise, my cock grew, clearly enjoying reminiscing about all of this. It quickly discovered its new home in the chastity cage, however, and the discomfort of that made itself known almost immediately. I couldn't even draw the slightest bit of pleasure anymore. Mistress Syn had made sure of that.

Had that been all, I might have been alright. Might have been able to withstand the barrage of pictures and videos again and again as I'd been ordered to do. Even with the chastity cage denying me, I could have been alright. But true to her wicked ways, Mistress Syn had included something else on the drive. Something she knew would break whatever sense of self I may have still had.

Her 'lessons' with Jane.

When I'd first arrived at her dorm earlier that evening, I'd witnessed Jane kneeling naked by her feet and assumed that she'd gone through the same torment I had prior. Mistress Syn had even alluded to such a thing, the idea of which had made me feel worse than I already had.

But it had all been a facade.

Rather than videos of Jane being forced to worship Mistress Syn's dirty feet or clean up her dorm or heaven forbid lick her toilet, I was instead presented with footage of the two of them hanging out and planning this evening's lesson in exquisite detail.

Things began rather normal, with Jane arriving at Mistress Syn's dorm, and based on their conversation, it was plain to see that at some point prior, she'd been told that Mistress Syn had some information about me that she wished to share.

I'd expected this, given she'd told me that Jane had been horrified by the things she'd done to me.

But she hadn't.

She'd been intrigued.

The video continued with them sitting on Mistress Syn's couch looking at the same pictures and videos I'd just watched myself and with each one, Jane seemed to grow more and more interested. It appeared that the meek, innocent-looking classmate I'd thought to get close to was just as twisted as Mistress Syn was. The difference was, she'd never had the chance to experience any of the things she'd fantasized about firsthand.

Mistress Syn and I changed all that it seemed.

"So wait," Jane said as she stared at the screen. "He just does all this?"

"Well, not at first... I told you he was checking me out right? Well, I decided he needed to be taught a lesson.."

She flipped through more photos on her phone, likely going back to the beginning, but that was enough to hook Jane, based on her expression.

"I had to force him, but he deserved it... And after our first 'lesson', he learned his place... Besides, he knows if he ever disobeys me he's fucked. See?"

Jane's eyes lit up as she looked at picture after picture and video after video. All the blackmail material Mistress Syn had collected on me thus far.

"Wow... I can't believe I was even the slightest bit interested in him."

That hit me hard, but she was just getting started.

"Oh my God, he's actually dressed like a maid!" She laughed, pointing at the screen with abject glee. "I thought you were joking, but he's really cleaning your place like that... That's amazing!"

"That's nothing," Mistress Syn said with a smile. "Watch this."

Though I couldn't see what was on the phone, I could hear the sound of my punishment, and the look in Jane's eyes as she watched Mistress Syn beat my backside, was enough to tell me she was not only into what she was seeing, she wanted in. A fact she quickly made known.

"Do you think I could have a go at him?"

Mistress Syn seemed to think this over for a moment, then nodded. "I don't mind sharing... But there have to be some ground rules."

"Of course."

The two of them discussed their plans, and I had to admit, they were quite thorough. Jane would miss a few classes so as to mess with my head, then Mistress Syn would tell me to come to her dorm where they would make me believe that she had done the same to her as she had to me, further breaking my spirit. Then they would humiliate me and punish me as both another lesson and a way for Jane to have a real taste of things.

It was clear that something long dormant inside her had been awakened by the revelation of my abject submission, and being given the chance to give in to such desires at long last was too much for her to resist.

Especially when Mistress Syn added the proverbial cherry on top.

"If we're gonna do this, you're gonna have to submit a little too... But don't worry, you'll have a lot more fun than he ever will... I tend to spoil my girls... What do you say?"

The look on Jane's face spoke volumes, not simply about her desire to be part of this, but something else. Something which told me that she, like me, had likely harboured a slight interest in Mistress Syn from afar, and was now being given the opportunity to indulge in it in a way I would never be able to.

Then she said something which pushed me even more over the edge than everything else had.

"I'd say... Yes, Mistress Syn."

With a smile on her lips, Jane kissed Mistress Syn hard and the two of them began to make out in earnest, a scene which would have seemed extremely hot to me before all of this had happened, but now did little more than torment be further. Especially as the video didn't end there, but instead continued with the make-out session turning into a round of full-blown clothes-torn-off dirty sex.

The sound of their shared moans rang in my ears as I watched them go to town on one another, with Mistress Syn eating Jane out for all she was worth and Jane returning the favour. I lost count of how many times they got one another off, and as my eyes filled with tears and my cock leaked precum into its cage, I knew why Mistress Syn had wanted me to watch all of this. It wasn't simply to relive my past humiliations over and over again, although that was certainly a big part of it.

It was to drive home just how pathetic I was. Not simply in her eyes, but in Jane's as well.

Seeing Jane not only agree to join in the humiliation and domination of me but to willingly give herself to Mistress Syn for the chance to do so, was more than I could bear.

Having one gorgeous woman continually degrade, dominate and destroy me was one thing. Having another join in for fun was a whole other.

Before watching all of this, a small part of me had retained a spark of hope. That perhaps, if the day ever came when I managed to escape from Mistress Syn's clutches, I'd still have a chance at a normal relationship with a woman. But now, seeing how easily another woman could see me as little more than a pathetic slut, I knew that would never happen. All I was, all I would ever be, was a useless Trinket for Mistress Syn and anyone else she decided to share me with.

That video ended with the two of them laying side by side in the afterglow of countless orgasms, but it was followed by several others just like it. Mistress Syn and Jane making out, fucking one another, some slight spanking of Jane that seemed tame compared to everything my behind had been through, and discussing just what they were going to do to me.

Somehow, watching them have sex without another while openly talking about me so dismissively- almost like foreplay, was beyond brutal, and though I knew the only videos left which could possibly come after these, I wanted them to come sooner than later rather than witness more of this.

Eventually, they did, the playlist moving on to tonight's events. My arrival at Mistress Syn's dorm, her presentation of Jane as another victim of her wicked whims, my being forced to listen to them go at it followed by their dual strap-on assault and punishment of me. Fresh as all these events were in my mind, seeing them again only reinforced just how pathetic I truly was.

And yet, even watching myself get fucked in both ends before being forced to clean my own cum off their strap-ons wasn't nearly as humiliating as knowing that Mistress Syn and Jane had planned all of this, conspiring to break whatever spirit I may have had left.

Worst of all, that they had succeeded.

When the playlist finally ended, I stared at the lack screen of my laptop for a few moments, the lingering pain in my behind as well as the ever-growing discomfort for the chastity cage holding back my desperate, precum-leaking cock, was nothing compared to the heavy weight in mind as everything came crashing down around me.

I didn't know what to do, so taken aback was I by everything I'd just experienced and witnessed. While once upon a time I would've been angry to have been misled in such a way, I knew now there was no point. After all, what could I do, complain about it? Mistress Syn had simply decided to add another 'tutor' to our lessons, and all I could do was accept that.

In the meantime, I did the only thing I could think of.

I started up the playlist again.

As everything played out in front of me yet again, my eyes and cock cock

began to leak in unison, a shared display of humiliation, especially once I reached their conversation videos once more. Somehow, seeing Mistress Syn and Jane discuss my previous lessons as well as the most recent one whilst they fooled around like it was the most normal thing in the world was far worse than any punishment I'd received so far.

And I knew this was only the beginning.

Mistress Syn not only had more than enough blackmail material on me to ruin my life multiple times over, she now had a willing and eager accomplice helping her out.

I was really and truly screwed, and she knew it.

After two more play-throughs of the entire USB, I went to bed, but I didn't have a restful sleep. Between my still-aching behind and the uncomfortable cage around my cock, as well as the things now playing in a loop in my mind, it was impossible for me to do anything but lay there and suffer.

Yet I still repeated this same self-flagellation the next two days, my weekend a veritable mashup of watching the videos and slideshows and reinforcing this latest lesson as I waited for Mistress Syn to call on me for my next one. And each time I watched, I felt more and more worthless.

I was truly nothing, not even a speck of dirt on the bottom of her boots. And worst of all, I was beginning to enjoy that fact.

Maybe it was all my previous lessons coming together in my mind, of simply the continuous revisiting of them in video form, but the more I watched, the more my cock reacted to my humiliation and punishment with zeal. It was almost like it was being programmed to react in such a way, and frankly, at this point, it wouldn't surprise me if that was part of Mistress Syn's 'lesson plan'- to break me to the point where I would be turned on only by her humiliating me.

I hoped not, but either way, I really didn't have a choice. If she said 'Jump', all I could say in return was 'How high" and she knew it.

In between all of this, I managed to bring her sheets to the cleaner and picked up the maid outfit I'd left there, trying my best to ignore the questioning look of the employee there. There really was no way I could explain any of this without digging a deeper hole for myself, so I didn't bother.

Luckily for me, they managed to clean the sheets quickly, and there were no residual stains left over from my little 'accident'. I even managed to drop both them and the outfit outside her dorm before Monday came around, along with a rather large tribute in payment for Friday's lesson.

But if I thought things would get better once classes started up again, I was wrong.

Up until that week, I'd only ever really seen Mistress Syn around campus sporadically, but now? Now she seemed to be making an effort to cross paths with me as often as she could. She never said a word to me of course, nor did she acknowledge my existence in the slightest, but she did make sure I could see the key hanging around her neck whenever she saw me.

The key to my cage.

Every time my eyes landed on it I felt even lower, knowing in my heart just how

badly she had me by the balls. There was nothing I could do about my chastity, and seeing the key just hanging there only reinforced that fact. She was revelling in the power she had over me, and she wasn't alone.

For the first time in weeks, Jane returned to class, but the demure girl I'd first chatted up was long gone. In her place was a woman who had so clearly been corrupted by Mistress Syn that even people who knew nothing about our situation could see the change.

Jane was dressed very similar to Mistress Syn, with fishnets and boots and a top that showed off her assets, as well as makeup that was almost exactly the same as Mistress Syn's own. The only thing missing were tattoos and piercings, but I wouldn't be surprised if those followed as Mistress Syn moulded her new plaything in her image both for fun and to add further humiliation to my day-to-day life.

She took a seat across from me, and just like Mistress Syn, didn't acknowledge me at all.

What she did do, however, was tease the ever-loving fuck out of me.

At various points throughout the lecture, my eyes were drawn to her fishnet-covered legs as they stretched out and crossed in full view of me, the leather boots she was sporting pointing at me and making my cock strain against the chastity cage every time.

The more she did it the redder I got, and more than once I saw her shoot me a wicked smirk. Jane knew exactly what she was doing, and she was enjoying every second of it.

I could not recall a single thing we learned that day, my mind completely focused on the continuous teasing from Jane, and when class let out I watched as she made her way over to me with a wicked grin and slid a hand towards my crotch. It was impossible not to feel the chastity cage beneath my pants, and Jane smiled once her fingers touched it. "Glad to see you're still locked up tight," she said as she groped my cage when no one was looking.

Had that been the extent of it, it would've been enough to add to my seemingly never-ending humiliation, but Jane wasn't finished with me.

Or rather, Mistress Syn wasn't.

"I have a message for you Trinket. Mistress Syn wanted me to tell you that your next lesson will be this Friday. But not in your dorm or hers..."

My eyes widened at this revelation, my mind filling with worry that they intended to do something to me in a far more public setting. My fear was all over my face, and Jane had to suppress a giggle at the sight of it. "Don't worry, it'll still be behind closed doors... Just different ones than you're used to."

Then she squeezed my caged cock one more time and grinned. "Keep up with your homework. Mistress Syn wants you to watch those videos at least three times a day... And so do I."

Jane winked at me, then headed out of the class with me following behind. Once I reached the hallway I watched her meet with Mistress Syn and the two of them walk off together hand-in-hand, and I just knew that whatever they had planned for this next lesson, it was going to be something far worse than I'd experienced so far.

With a sigh, I headed back to my dorm, wondering just what they had in store for me come Friday, and knowing I had at least two more play-throughs of their video torture of me to go before the day was done.

And much as I hated to admit it, I was looking forward to it.