Sinful Tutoring - Lesson 05

This chapter would not exist without Synful Mistress's help. She gave me the ideas and got the ball rolling when I wasn't sure what to write next. Seriously, check her out. She's awesome.

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After my last lesson, I managed to get back to my dorm in one piece, my ass still red and reeling from the punishment Mistress Syn had given me. I felt as low as could be, a fact not helped by the Ziploc baggie in my pocket that contained a pair of her used panties.

My homework it seemed.

There was a time when the idea of having a gorgeous woman's panties in my possession- let alone being told to jerk off with them, would have sounded like a dream come true. But now? Now it was just another chapter in the ever-growing nightmare of submission my life had become ever since I had foolishly gotten involved with Mistress Syn.

Once I got inside, I locked the door behind me and sighed. Half the day was over and done, and all I had to show for it was a red ass and further humiliation on the horizon. Pulling the baggie from my pocket, I stared at the red and black lacy panties inside, the stains filling me with disgust.

Warily, I stripped out of my clothes, took a seat on the couch- nearly jumping in pain the moment my aching bottom touched the cushions, and picked up the Ziploc. Opening it, the strong scent of sweat poured out, and I knew without question that this particular pair was one Mistress Syn had worn quite a bit, as well as one which had likely been marinating in that clothes hamper for some time.

Much as I didn't want to, I slipped them out and placed them over my nose, the scent washing over me almost immediately, and began to slowly stroke my cock.

It wasn't easy to get hard, the pain from Mistress Syn's cane still prevalent, but I forced myself to keep going, stroking up and down my shaft while taking in shallow breaths. The scent of sweat was indeed strong, and though I could just barely smell what I gathered was her pussy juice somewhere underneath it, there wasn't enough for me to gain any enjoyment.

Only the smell of dirty, sweaty fabric going in and out of my nostrils while I stroked my cock, wishing I were smelling her pussy and ass instead.

It was humiliating to think about, yet a part of me continued to enjoy it.

Even with everything else that had happened- especially with everything that had happened today alone, I found it difficult to fully separate my growing lust from the source of it. Here I was, sitting naked in my dorm sniffing someone's used panties and masturbating while doing so.

Someone who had- by this point, forced me to sniff and lick their sweaty feet, smothered me with those same feet as well as their ass, made me clean their dorm from top to bottom while wearing a slutty maid's outfit, canned my backside, and had me paying for the 'privilege' of it all.

Twisted as it all was, I knew there was nothing whatsoever I could do about it. Mistress Syn had countless pictures and videos of our various 'lessons', let alone whatever videos she'd recorded while I was cleaning her dorm. Regardless of the context, even one of those would be enough to get me kicked out of school, and likely ruin my life.

So I stroked my cock, felt it grow harder and harder with each pass and each breath, felt the coming bliss of an orgasm and forced myself to stop.

The agony of denial was rough, and I felt tears form in my eyes for the second time today, but I knew this was only the beginning. Mistress Syn had demanded I do this over and over, every day until she said otherwise, and after today I dared not disobey her again.

As my cock slowly deflated from lack of contact, I slipped the panties back into the baggie and started to cry. I repeated this scene three more times before the day was through, each time getting myself so close to cumming before stopping. Each time it got a little easier, but I still felt so damn pathetic.

I tried to convince myself that this was fine. That I didn't really want to cum- which was a lie. After all of Mistress Syn's lessons, after being in her presence, I was beyond horny like it or not, but the idea of cumming whilst being forced to breathe in the scent of her well-worn panties still disgusted me.

At least, for a little while.

By the end of that first week, things started to change. I couldn't explain why- maybe some sort of weird association thing, but whereas before I'd needed to force myself to jerk off while sniffing those panties, now my cock sprung to life on its own. In fact, the moment I looked at the baggie, I started to get horny.

I didn't like that one bit, but there really wasn't much I could do about it. Mistress Syn had me by the balls in more ways than one, a fact she happily reminded me of that weekend. Though she did not grace me with her presence, she texted me late Sunday night, and her words, even on my phone, carried with them such incredible wickedness.

"Hope you've been doing your homework every day Trinket ;)..."

`There was no point sending a response, at least not one with words. Instead, I opened up my bank app and transferred a tribute to her. Payment for this latest lesson.

She replied with a black heart, and then nothing more, and I continued on as she had commanded, edging myself over and over even as my cock begged for a release I wasn't allowed to grant it. Only Mistress Syn could do such a thing, and I had my doubts she ever would.

As that first week ended and the next one began, I continued to do the same, but by the middle of it, I grew somewhat concerned. I hadn't seen or heard from her since that brief message, and by the following weekend began to question if, perhaps, she'd finally had enough fun with me or decided I'd finally learned my lesson.

It was a foolish thing to think of course, but given I'd managed to get myself into such a mess in the first place, it was no surprise I'd somewhat find a way to dig a deeper hole for myself even if I didn't mean to. Even so, after two weeks of edging, two weeks of denial, two weeks without any further lessons from Mistress Syn, I guess I wasn't thinking straight. Or at all.

You see, even with all of this going on, I tried to keep living my life just as I had before our first fateful meeting. I worked my part-time job, went to my classes and did my assignments, putting on the facade of a normal College student so that no one would suspect the truly deviant activities I'd found myself doing.

And during one of those classes, I made my next mistake.

I'd noticed her a few times before, but like with Mistress Syn before her, never managed to say a word to her. Her name was Jane, and she was short, cute and quite sweet. In essence, the very opposite of Mistress Syn, at least in attitude. Maybe that's what attracted me to her, the idea of maybe spending time with someone so different from what I was slowly growing used to.

On a whim, we started chatting, and I asked if she wanted to grab a coffee after class. She happily accepted, and for the first time since all this had started, I felt normal again. As if I had the possibility of a normal College student life regardless of everything else.

Looking back, I honestly wished she had said no. But then, I had no way of knowing what was going to happen.

When class let out, Jane and I made our way to the campus coffee shop, grabbed a table as well as our drinks, and started joking around. We talked about upcoming assignments and plans and so on, and for the most part, things seemed to be going very well. I actually considered asking her our proper when all was said and done, but that idea quickly vanished when I looked up and spotted someone staring at us from the other side of the shop.

Mistress Syn.

She was dressed fairly casual, at least compared to the last few times I saw her, with a black metal band t-shirt and a purple and black plaid shirt along with fishnets and leather boots. But the fact that she was here now, and clearly watching me, filled me with dread.

I tried to keep my conversation with Jane going, but my eyes continually made their way over to Mistress Syn. She watched us curiously for a few minutes but didn't say or do anything. She could easily have walked over and shown off one of the countless pictures or videos she had of me, but for whatever reason, she refrained. Simply finished up her drink and walked out without a word.

Even so, I was wary as could be, and when Jane and I finished up we said our goodbyes and figured we would see one another in class next week.

All the while, as the next few days went by I continued to edge, and waited with bated breath for Mistress Syn to make herself known once more. There was simply no way she wasn't working on a future 'lesson' for me, especially after spying me with Jane. And yet, oddly enough, I didn't see or hear from her at all.

Two weeks passed since that day, and still nothing. I should have been worried about that, but frankly, I had much bigger things to worry about.

Namely, the fact that Jane hadn't been to class since that day at the coffee shop.

Now it was quite possible she was busy with other classes, or sick, or something else entirely. Yet somewhere in the pit of my stomach, I had a sinking suspicion that something else had happened to her. Or rather, someone else.

It was Friday evening when I finally found out the truth.

I was in my dorm preparing to edge my now desperate cock once again when my phone rang. Mistress Syn had not previously deemed me worthy of receiving a phone call, preferring to show up outside my door or text. The fact that she was calling me now was disconcerting, but not nearly as much as what she had to say when I picked up.

"My dorm. Ten minutes. Be there or else."

Then she hung up, and I practically bolted out of my dorm towards hers, Ziploc

baggie still in my hand. My heart was beating in my chest with excitement and worry and a myriad of other emotions that frankly had no business lumping themselves together. Even so, after that message, I could only assume that whatever was waiting for me at her dorm would be quite unenjoyable.

I was half right.

After stopping along the way to pull out a tribute- better safe than sorry, I knocked on her door, and could only stare as Mistress Syn opened it with a wicked grin. One that suited her well given she was once more dressed to dominate, with a tight leather one-piece top, black fishnets, and those black knee-high leather boots I'd grown quite familiar with.

"Well well Trinket, so glad you could join us tonight."

Standing there, I was taken aback by the 'us', immediately worrying that perhaps she had brought in a friend of hers to aid in my continued humiliation, a fact that I have to admit I was strangely turned on by. But it wasn't a stranger waiting for me inside her dorm, but someone I knew.

Jane.

Kneeling by the couch, naked save for a collar and leash clamped around her neck, head hung low in complete and utter defeat.

My jaw dropped at the sight of her, and I didn't even realize I'd stepped inside until Mistress Syn shut the door behind us and locked it.

"Aww, surprised? You really shouldn't be. After I spotted you two getting cozy at the coffee shop, I decided to offer your little friend here some free tutoring. Wasn't that sweet of me Trinket?"

I had no words. My mind was reeling at the sight in front of me. Jane could barely look up from the floor, and I knew without asking that she was just as broken as I was. Completely and utterly torn down and rebuilt by Mistress Syn and her wicked whims.

Without waiting for me to respond, she walked over to Jane and patted her on the head like a puppy. "I told her ALL about our lessons, showed her the pictures and videos too... She thought I was being so mean to you. Can you believe that?" Tapping the toe of her boot on the floor, Jane dropped down to kiss the well-worn leather, and I sighed even as Mistress Syn grinned. "After a few lessons though, she started to come around. Didn't you bitch?"

Jane stopped kissing the boots in front of her for a second to answer sadly. "Yes, Mistress Syn."

I felt terrible knowing that someone else was now sharing my fate, especially seeing as it was due to my own foolish actions. I should have known better than to think that Mistress Syn was finished with me. Yet at the same time, a small part of me was also strangely turned on.

The idea of someone else submitting to her just as I had was arousing in a way I couldn't explain. My mind was torn between the two feelings, and I highly doubted I'd be able to reconcile them anytime soon.

Mistress Syn watched Jane for a moment before pulling her boot away and turning her attention back to me. "Forgetting something Trinket?"

In my shock, I'd forgotten to strip, and though I knew I should feel somewhat embarrassed given there was someone else here this time, someone who, up until this moment, I'd honestly considered asking out, seeing as they were in the same boat as me now it didn't seem to matter all that much.

Taking the tribute from my pocket, I placed it and the Ziploc baggie on the coffee table then removed all my clothes and put them on the table by the door. Then I too was naked and kneeling, and Mistress Syn smiled wickedly as she pointed out the panties. "Did you edge your pathetic dicklet Trinket? I hope you loved the smell of my dirty panties because that's all you deserve. Now crawl over here and join your little friend."

I did as she asked, feeling even lower now that she had essentially revealed my most recent lesson to Jane. I doubted she would ever be able to look at me the same way again after this, or I her. Kneeling beside her, our eyes glued to Mistress Syn's boots, I wished I could apologize for all of this, but knew that nothing could ever truly make up for what she'd been through.

"Aww, aren't you two so cute," Mistress Syn began, taking a seat on the couch and staring down at her handiwork. "You know Trinket, you two have so much in common now. In fact, you've both had the privilege of cleaning up my dorm. Didn't she do a good job?"

Looking around, it did seem cleaner than when I'd done the job, although that could have been due to my desire not to say anything contrary. "Yes Mistress Syn," I replied, and out of the corner of my eye, I saw Jane's eyes close. She had likely learned to say those three words just as easily as I had.

Mistress Syn giggled wickedly. "She was much more thorough too. In fact, my toilet has never looked cleaner."

My mind immediately went back to my own cleaning of the place, along with the worry of what she had in store for me. Looking at Jane, I saw disgust and dismay cover her face, and my stomach dropped as I realized just what she'd had to do. A fact Mistress Syn quickly confirmed.

"Your friend has a really useful tongue... But I guess you didn't have the chance to find out for yourself, did you Trinket?"

I hung my head low, and she let out a cruel laugh. "Aww, what's the matter? Don't you still want to kiss her? I'm sure her mouth tastes lemony-fresh after everything it cleaned."

Jane's eyes began to tear up, and much as I wanted to reach out and comfort her, I knew I wasn't able to. We were both so beyond fucked, and though I'd had plenty of time to come to that realization myself, it was clear to me she'd gotten a veritable crash course.

"Well, if you don't want it anymore, then I'll just have to have all the fun with it. Come here bitch."

With a snap of her fingers, Jane crawled over to Mistress Syn, and I watched as our shared owner slipped the bottom part of her one-piece to the side, revealing a freshly shaved fishnet-covered pussy. I'd never had the luxury of seeing her snatch, and regardless of everything else going on at the moment, I have to admit, the sight of it caused my already slightly erect cock to rise and gave me a joy I hadn't felt in some time.

A joy that was just as quickly taken away.

"Ah ah ah. No looking! Naughty Trinket. You don't get to watch. You will look at the floor and listen while your little friend eats me out."

I did as she commanded, and soon enough, the sound of Jane's mouth and tongue licking Mistress Syn's lips and lapping up her pussy filled the room. She took her time, slowly adding small moans to the air, causing my cock to grow even as it was continually denied. Just knowing that Jane was eating her out less than two feet from where I knelt was incredible yet cruel, and I could only look down and listen.

"Mm-mm, fuck that's good... Her tongue feels SO GOOD on my pussy," Mistress Syn taunted and teased. "I bet you wish you could see it, wish you could taste me Trinket... Or maybe stick that pathetic little dicklet of yours inside and fuck me. Bet you'd love that, wouldn't you?"

Without daring to look up, I answered the only way I could. "Yes, Mistress Syn."

Another evil laugh followed, one that was tempered with ever-growing moans of pleasure. "Too bad. You don't deserve that either, does he bitch?"

Jane stopped her worship of Mistress Syn's pussy. "No Mistress Syn."

She sounded so defeated, so broken, and it made me feel horrible even as my cock continued to grow harder and dribble out precum from the sound as well as the taunts.

"Isn't his dicklet so pathetic? Look at it getting hard when his Mistress teases him."

For the briefest of moments, Jane's tone changed as she looked over at me. Less sad and accepting, and slightly more cruel. As if the fact that she was only in this mess because of me had fully sunk in and she was going to take whatever smidgen of revenge she could. "Yes, Mistress Syn. So small and pathetic. It doesn't deserve your perfect pussy."

I don't know if she'd been trained to say that, but somehow I doubted it. I think that was Jane's true feelings and, given the situation we were now in, I couldn't blame her. Worse than that, having her agree with Mistress Syn only made my cock spew more precum.

"Good girl," Mistress Syn said, then guided Jane's face back to work. As she continued to tongue-fuck the fishnet-covered pussy of our shared Mistress, I knelt there silently listening, letting their words echo out in my mind. They were both right and I knew it- I did not deserve Mistress Syn's pussy. Hell, after this, I didn't deserve any pussy. I was pathetic.

The closest thing to a girlfriend I could have had was now eating out another woman's pussy, and likely doing a far better job at pleasing her than I could have done to either of them. If I hadn't already felt as low as could be during and after my other 'lessons', this one was certainly doing the job.

But I knew that wasn't what I was supposed to be learning this time around, it was simply a bonus. No, Mistress Syn was telling me, in no uncertain terms, that there was indeed no escape from her. I'd tried- maybe not intentionally but still, and look where it had got me.

Regardless of what had happened, regardless of how many days or weeks went by without a word, I was hers and hers alone. Mistress Syn owned me.

And now she owned someone else as well.

Her moans grew louder and louder, and before long they turned to cries and screams of pleasure. "Don't stop, don't you dare fucking stop," Mistress Syn uttered in between, and I listened as she came, the sounds of Jane making her climax filling my ears. It was even more humiliating than I'd expected, as I didn't even have the brief satisfaction of watching the act. I could only listen and suffer.

As Mistress Syn came down, she moaned gently even as Jane continued to lap up her pussy hungrily. "Good girl... You're already so much better than he is."

Even without looking up, I knew she was staring at me, and I felt even more pathetic than I had before. Once again, without touching me or doing anything to me physically, she was asserting her dominance over me with only her words. And I was loving it.