Sinful Tutoring: Lesson Seven

I legit can't believe how many parts I've written for this story in such a short time. Such is how amazing a muse Synful Mistress has been. Seriously, check her out. My words don't truly do her justice.

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After several minutes, Mistress Syn broke the embrace and she and Jane looked over my work to make sure I hadn't left a trace of cum on either of their strap-ons.

"Not bad," Mistress Syn said dismissively. "Guess that mouth of yours is good for something."

Jane giggled, then the two of them undid their harnesses and placed the strap-ons on the shelf with Mistress Syns other toys. Even though I should have been relieved, I knew that their assault on my holes had only been the appetizer. The main course still remained.

"It's time for your punishment," Mistress Syn commanded, pointing to the end of her bed. "Assume the position Trinket."

Crawling over, I draped my arms out so that she could restrain me once more. And as I did, I watched Jane move the bedsheet, and in a moment I understood why.

Not all of my mess wound up on their cocks. They'd left a little more for me to take care of, and they had the perfect way for me to do so.

By sticking my face in it.

"Good girl," Mistress Syn said, smacking Jane on the ass as she finished restraining me and causing the other woman to blush.

Any and all despair Jane had shown when I'd first arrived had seemingly vanished. Whatever cruel lessons Mistress Syn had taught her these last two weeks had faded away, replaced by a wickedness that matched her own. A wickedness that sent shivers down my spine.

Once I was well-secured, my face inches above the small pool of cum, I could only watch as Mistress Syn and Jane walked past me and headed over to the wall. And though there was no way for me to witness their selection process, a moment later that both returned to my line of sight to proudly show off their chosen tools.

Mistress Syn held the same cane she'd used on me the last time, and Jane had picked a riding crop. They gazed down at me and drank in my fear as well as my continued submission, and I dropped my face into the still-warm cum and waited for my next lesson to begin.

The familiar sensation of the cane on my bare ass cheek shot through me almost immediately, and I cringed as the sticky mess slid across my lips. I knew the moment I opened it I'd get another taste, but also know that if I dared scream in pain there would be even harsher punishment.

So I gave in and did it.

My mouth was immediately filled with the disgusting taste of cum and fabric, as well as traces of sweat and Jane's own dried juices. I wanted to gag but Jane's crop struck my cheek hard, stinging in a completely different way than the cane had, forcing me to take in more of the sheet as well as my load, gagging myself even as they continued their assault.

Another strike from Mistress Syn followed, then one from Jane, and before I shut my eyes I spotted the clock on the bedside table. Barely five minutes had passed since they'd begun, and tears were already streaming down my face. Two more from each of them struck me, and my ass, already aching from the thorough fucking it had received, had no choice but to take it.

And still, they were just getting warmed up.

Before I could even attempt to recover, more strikes rained down on it, this time one on each cheek. Mistress Syn's cane slapped against one as Jane's riding crop hit the other, the stereo attacks sending waves of agony through my body I'd never thought possible.

"He's such a slow learner," Mistress Syn said, followed by another shot from her cane. "Not like you my sweet little bitch."

"Thank you Mistress Syn," Jane replied happily, nailing my bare ass with two quick whips from the riding crop.

"Good girl," Mistress Syn added. "You can learn a lot from her Trinket," she accented her words with another swat. "Like to thank me for this. In fact, you better start thanking us after every hit or things are going to get so much worse. Understand?"

I couldn't fathom how things could possibly get worse, but I also didn't want to find out. I knew what she wanted, and though I didn't want to do such a thing, I knew better than to disobey her again. Besides, at this point, why bother pretending I had any dignity left at all?

I'd been fucked in both ends and been made to lick and suck my cum off a pair of thick, rubber cocks. This was just the cherry on top of the submission sundae Mistress Syn had ordered.

Letting go of the cum-drenched bedsheet gag, I felt the dual sensations of the cane and the crop on my likely reddening ass, and through tears, said the four words which now seemed to come to me as easily as breathing once had. "Thank you Mistress Syn."

Another thwack, followed by an admission of thanks. Each and every time one of them hit me, I held back cries of pain but dared not forget to say those words which now felt like life and death at this point. And every time I spoke them aloud, every time I found myself thanking these women for their continued assault on me, the lower I felt.

I was thanking them for punishing me.

Thanking them for beating my ass red and still not letting up. Worst of all, my cock- which had momentarily shriveled up after it had finally had its unplanned release, was starting to get hard again. It was thoroughly enjoying the fact that the rest of me was in utter agony, and that made things even worse.

Looking back at the clock, I watched time slowly go by. Ten minutes, fifteen, twenty. A smack from the cane, one from the crop, one from each. Neither Mistress Syn nor Jane letting up for very long. And still, I thanked them each and every time with tears in my eyes and my face pressed against the cum-drenched bedsheet.

After the most recent one- I'd honestly lost count of how many times each of them had hit me, I thanked Mistress Syn, but this time it seemed to be the wrong thing to say. Because instead of following it up with another blow, she stopped and asked me something unexpected.

"Thank me for what, Trinket?"

My eyes widened in surprise. I was so taken aback by her unexpected question, so unsure of what to say, that I was completely unprepared for the strike from her cane. One which told me in no uncertain terms that she wasn't in the mood to wait for me to answer her.

I had to think fast, to figure out just what it was Mistress Syn wanted me to say.

But I couldn't.

And they made me pay for that.

A barrage of strikes rained down on my aching ass cheeks, at least a dozen from each woman in the span of a minute. I shoved my face into the bed to muffle the scream which threatened to escape me, my tears mixing with my juices and sticking the sheet to my face.

"He really is a slow learning Mistress Syn," Jane added coldly, though she didn't hit me again much to my relief.

"Oh, I know... Honestly, I thought he'd have figured it out by now," Mistress Syn replied rather dismissively. "But I guess stupid little whores like him need as many lessons as they can get before they sink into their itty-bitty brains."

Much as I hated their belittling of me, the fact that no further blows followed it gave me some momentary relief. However, I knew it wasn't going to last. I heard the two of them head back toward the wall and shivered wondering what else they had in store for me. I doubted they were finished, but what further punishment did they have for my apparent ignorance?

The sound of the toys being placed back on the wall followed, as did the sound of others being taken down. Before I could consider which they'd taken this time, they had already walked over to the side of the bed, and I could only stare in fear at the wooden paddles now in Mistress Syn and Jane's hands.

Both of them looked down at me with disgust, and I felt as low as I possibly could without either of them needing to say a single word.

They returned to the end of the bed, and less than a minute later I felt an entirely different kind of pain than I was used to. One of the paddles slammed into my already tender flesh, and though I thought I'd run out of tears to cry, somehow my body managed to find some more, and they quickly began to flow down my face as the other paddle struck.

If I'd thought the cane and crop had been painful as it could get, I was dead wrong. They were child's play compared to the paddles.

It didn't help matters that these covered far more space than the other toys had, which meant no part of my reddening cheeks was safe from the dual assault of Mistress Syn and Jane.

And they were certainly making sure they got every inch of my ass as red as they possibly could.

Though a part of me had thought to cry out in thanks after each swat, I knew that if I did Mistress Syn would demand an answer, and I still didn't have one to give her.

All I could do was kneel there by the end of her bed as they paddled my ass for all it was worth, wracking my brain trying to figure out just what it was that I was supposed to learn from all of this. What lesson was Mistress Syn trying to teach me this time?

At first, I assumed it had something to do with my foolish orgasm, but given this punishment was due to that mistake, it had to be something else. Something beyond this moment. Something which had, perhaps, begun the very moment Mistress Syn had first entered my life.

Ten minutes passed, the blows not letting up, nor my tears stopping in the slightest. My cock, at long last, had deflated, the pain from the paddles too much for even it to handle now. And yet, I continued to struggle, to figure out the point of all of this.

And then, a light bulb switched on in my pain-addled brain, and I finally understood.

"Thank you Mistress Syn" I practically screamed even as the latest blow still felt fresh against my skin.

"For what, Trinket?" She asked, something in her voice telling me that I wouldn't have another chance at this. This was it, the moment of truth. If I was wrong, if the answer I'd stumbled upon wasn't exactly what she wanted to hear, then I was finished. And so was my ass.

"Thank you for showing me what a pathetic little whore I am... For punishing me when I disobey you, for granting me the privilege of being fucked by you. For teaching me again and again and again that you own every single part of me, and for allowing me to pay you for such important lessons...."

It all flowed out of me so easily, so naturally, like it was the most normal thing in the world to say. And yet still I shut my eyes in fear, half-expecting to be wrong. For another blow to follow, for the punishment to begin anew, or that, perhaps, a far worse one would instead begin in its place.

Instead, the restraints around my wrists were undone, and as I slowly slid my arms free, I gazed up at Mistress Syn who looked down at me with a small smile from the side of the bed.

"Good Trinket... You're finally learning your place."

I watched her take the paddle from Jane and placed them both back on the wall alongside her other tools. Even though my body ached from my punishment, I felt good. Happy to have given the correct answer in the end.

But that happiness was short-lived, as Mistress Syn walked over to the shelf of sex toys and removed something small and metallic.

My eyes widened as I realized just what it was. As well as what it meant for me.

A chastity cage.

"Still, I think you need a bit of a study aid to make sure these lessons stick," Mistress Syn continued as she approached the end of the bed. "After all, you did break my rules. You need to learn to control that pathetic little dicklet of yours. This should help."

Then she handed me the cage and, without even saying a word, I understood what was expected of me. Of course, Mistress Syn had no desire to touch my cock with her bare hands, which meant I had to lock myself up for her. Yet another humiliation, and one which was truly in my hands.

With a sigh, as well as beneath the gaze of both Mistress Syn and Jane, I slipped my flaccid cock inside and shut the cage around it.

"A perfect fit," Mistress Syn added with a giggle. "I was a little worried I wouldn't be able to find one small enough for you Trinket."

Her giggle became an evil laugh, and Jane quickly joined in, much to my dismay. Then she handed me a small padlock and waited for me to lock the cage.

Knowing what it meant, knowing both what it symbolized as well as what would likely happen to me from here on out, I knew I didn't have any say in the matter. All I could do- all I'd been able to do since this whole thing had started, was what Mistress Syn told me to do.

So I locked the cage around my cock and handed her the key.

"Good Trinket," Mistress Syn giggled, and I watched her slip the key onto a chain and hang it around her neck. "I want you to be able to see this whenever I'm around. Whenever you spot me around campus or when I'm standing outside your door. I want you to remember only I can unlock that little bitty dicklet of yours."

I sighed. "Thank you Mistress Syn."

She smiled, then pointed at her feet. "Kiss my boots slut, and thank me for tonight's lessons... I expect a big tribute for them."

Dropping to the floor, I planted a kiss on the toe of each one of her faded leather boots. "Thank you Mistress Syn," I said softly, the cool metal of the cage an entirely different sort of discomfort compared to the fiery agony of my extremely red ass.

Jane stifled a laugh at my humiliation but said nothing, and Mistress Syn took a step back before motioning to the bed. "I want that sheet cleaned by Monday by the way. Your loser load better not have left any stains on it, or there will be hell to pay. Understand?"

I nodded, my eyes wide with fear, and once I made it to my feet I gently pulled the sheet off and prayed that I'd be able to get it cleaned for her. Maybe I'd bring it to the same place I'd brought the maid outfit- the maid outfit I still needed to return to her. "Yes, Mistress Syn."

For a second or two, I thought Mistress Syn was finished with me for the evening, but as I watched her walk over to the desk in the corner of her bedroom and remove a USB from the laptop sitting on it, I realized I was wrong. "Until our next lesson, I want you to take a little refresher... You are going to watch all these videos- but don't worry, they're just copies. I still have ALL the originals in a safe place."

It took me a moment to process what was on the USB, as well as why she wanted me to watch them, but once it did... Mistress Syn wanted me to relive all of my past humiliations, to make sure I never forgot them.

As if I ever could.

"Now, go put your clothes on and get the fuck out of here. Your little friend and I still have a few more lessons to take care of tonight..."

She slapped Jane's ass once more, then licked the side of her face in a show of pure dominance, Jane shivering as she did. Whatever Mistress Syn had in store for her, it was a far cry from what she had done to me.

With my head hung low and the stained sheets and USB in my hands, I made my way out of the bedroom, not daring to turn around to see just what it was they were going to do next. I'd seen and heard more than enough of that tonight.

Over by the front door, I put my clothes back on slowly, holding back a cry as my boxers and pants touched my aching behind as well as pushed the cold metal of the chastity cage closer to my cock. It was going to be a long, awkward walk back to my dorm, and I could only hope no one else would be out and about to see me and ask questions I didn't have answers for.

Opening the front door, I took a step outside just as the sound of a vibrator rang out from Mistress Syns bedroom, followed by more moans of pleasure. I had a fairly good idea what was going on inside. With a sigh, as well as the sheet wrapped in my arms and the USB in my pocket, I headed out of the dorm, somehow feeling even more pathetic than I had when I'd first arrived.

As well as knowing that, odds were, I'd feel even more so after my next lesson.