Sinful Tutoring - Lesson 04

Yet another piece inspired by the amazing Synful Mistress. Check her out if you haven't already. You won't be disappointed.

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If I thought I'd earned myself a reprieve from any future lessons after Saturday's cleaning spree, I was dead wrong.

When Monday morning came around, I was woken up by the sound of someone pounding on my door like a madman.

Groggily, I threw on some clothes and stumbled out of my room towards it, unsure who could possibly be knocking this early and why. But the moment I opened the door, I realized that not only could it be one person, it was indeed them.

Mistress Syn.

And she was pissed.

"You pathetic little shit!" She bellowed, pushing me inside the dorm and slamming the door behind her in a rage.

I had no idea why she was here now, let alone so angry. I'd cleaned her dorm just as she'd asked, and in half the time too. Had I forgotten something? No, I was certain I'd followed every instruction she had left behind for me. I'd even double-checked to make sure.

But it seemed I was wrong.

Before I could even attempt to speak, Mistress Syn slapped me across the face, and I instinctively dropped to my knees in fear and submission. But that wasn't enough. Not this time.

"Stupid fuckin whore, you can't do anything right, can you?"

She reached down and slapped me again, and though my cheek was burning with pain, I dared not move a muscle, hoping she would explain why she was angry with me.

"What did I do?" I managed to sputter out, and she answered with one more slap before taking a seat on my couch, glaring down at me all the while. As the pain subsided I was able to take in the sight of her- black fishnets that seemed to cover her arms and legs based on what little I could see under the coat she wore and a familiar pair of black knee-high leather boots. Were the situation any different, I'd certainly find the sight quite lovely, but now? I was terrified.

"You seriously don't know? Wow, you're even dumber than I thought."

Reaching into her bag, she removed the slutty maid outfit I'd worn two days earlier and tossed it toward me. "You didn't clean this when you were finished you stupid fuck. I walked in and saw it sitting there with your pathetic loser precum stains all over it!"

It honestly hadn't even crossed my mind at the time to clean the outfit she'd had me wear, but now that she was pointing it out, I felt like a complete and total idiot. Of course, I should have cleaned it, especially since I knew I'd left some... marks behind during my cleaning.

But she wasn't finished making me look like the fool that I clearly was.

"What, did you need a fucking note for that too? Is your little foot whore brain as tiny as your cock? Does it need to be TOLD to clean up after itself? Fuck!"

I started to sputter out an apology, but she wasn't through. "And worse than that, you didn't bother to leave a tribute when you left! Not a single bill was there waiting for me. Did you not learn your lesson yet? I. OWN. YOU. Unless you want all those pictures and videos I have of you to wind up all over campus?"

My eyes widened at the reminder of her threat, and I shook my head in fear, much to her momentary joy. "Didn't think so. That means you pay me for the privilege of being my little Trinket. Got it?"

Once again, I felt like a moron. Of course, she expected me to leave behind some money, yet that had completely slipped my mind.

Luckily, Mistress Syn was going to make damn sure I would never forget again.

Standing up, she grabbed me by the hair and pulled me from the floor. "Get your wallet. Looks like your next lesson is going to be right now. I don't have class, and if you do, you're skipping it today. Understand?"

I didn't have any class, thank God, but I also wasn't sure what sort of lesson she had in mind. Then again, given she had warned me that if I messed up cleaning her dorm there would be punishment, and I had seen plenty of ways she could do so while I was there.... I could only imagine whatever she had in store for me would not be good.

Dragging me out the door, she let go of my hair and started walking "Follow me Trinket. We have a stop to make."

I did as she ordered, and after a few minutes of walking across campus- which was mostly empty this early in the morning, the school ATM was in sight. Mistress Syn intended to get that tribute one way or another, and I knew if I didn't give it to her I'd be in even more trouble than I already was.

Once we reached it, she pushed me inside the little inlet where the machine waited, glaring at me as I pulled out my bank card. I took three-hundred dollars cash out, hoping it would be enough to redeem myself, as well as to pay for whatever lesson she had in store for me today.

When I turned to look back at her, however, she did not look the least bit pleased, so with my head hung low, I pulled out another two hundred and crossed my fingers.

Once outside, I handed her the bills, and Mistress Syn sighed. "Not bad. But you still need to learn a thing or two to make sure this doesn't happen again. Come on Trinket."

We started walking again, and soon enough I spotted her dorm, and I knew in my gut that the punishment I feared was likely coming. My head remained low as if I were a condemned man on his way to the gallows, only execution would be much swifter than whatever Mistress Syn was planning.

I followed her inside, and once she shut the door, she turned and glared at me. "Forget your other lessons already Trinket?"

Without a word, I stripped out of my clothes and placed them on the same end table I'd left them on Saturday.

Mistress Syn looked at my morning wood- still erect even after he scolding of me, and scoffed. "So pathetic. I yell and scream and slap you around and your little dicklet is still rock-hard for me. You really are a fucking little bitch, aren't you Trinket?"

What else could I say? "Yes, Mistress Syn."

She smirked for a moment, then removed her coat to show me the rest of her outfit, and my jaw nearly dropped to the ground.

I was right about the fishnets- she was wearing a full bodysuit of them, and had that been all it would have been more than enough. But on top of that- at least on the top, was a black leather corset with an opening which showed off her ample, fishnet-covered chest. Along with the boots, she certainly looked the part of a dominatrix, and I knew from experience she possessed the attitude and skills to be one as well.

"Like what you see, Trinket?" She asked teasingly, knowing from the look likely plastered all over my face, as well as my now leaking cock that I did. "Thought so... But that'll be the only pleasure you get. Today's lesson is pain. It's the only way you'll learn."

My face sank but I dared not say anything. Instead, I watched Mistress Syn pull a collar and leash from her bag and attach the former around my neck before clicking the latter to it. "On your knees Trinket."

I did as she said, and she took hold of my leash before leading me out of the living room, past the kitchen and bathroom, down the hallway, and into her bedroom.

It was exactly as it had been on Saturday, and my eyes widened at the memory of what I'd seen there two days prior.

All of Mistress Syn's toys.

Kneeling there in the doorway, I watched as Mistress Syn let go of my leash and walked over to the wall, slowly running her fingers across each tool as she considered which one she was going to use on me. None of them seemed enjoyable, but at least the cane and riding crops might hurt far less than the flogger or paddles.

"Hmm," she said eventually. "I just can't seem to decide... Maybe I'll use them all on you." Mistress Syn looked back and giggled at the fear and despair that was painted on my face at the very thought of that, following it up with a laugh that would have sounded sweet in almost any other context. "Aww, don't worry Trinket. It's too early for that much of a workout... At least this time."

I shuddered at the thought of there being a 'next time', and this particular lesson hadn't even started yet.

Eventually, Mistress Syn seemed to decide on the cane, much to my momentary relief. I knew it was still going to hurt, but compared to the larger paddles... Maybe I could survive this...

"This will do for now... Crawl to me Trinket."

With a sigh I did so, stopping by her bed, where Mistress Syn removed the leash. "Lay down," she said, and once I was half on her bed I understood why. I hadn't noticed when I'd cleaned here, but there were leather cuffs at each corner of the bed, and my arms were now being fitted into the two at the bottom. "So you don't struggle too much," she giggled, tightening the restraints while I lay there, ass in the air and cock pressed against her bed. I felt vulnerable and embarrassed, but she was only getting started.

Once I was properly restrained, Mistress Syn moved over to her nightstand and removed what I thought at first glance was a dildo, but as she brought it closer to me my eyes widened. It was, sort of. But it was more of a gag, with the rubber cock end meant for my mouth.

"Open wide Trinket," Mistress Syn commanded, and with trepidation I did, watching as she shoved the dildo end between my lips and secured the straps behind my head. "I don't want you waking up my neighbours with your cries... And you will be crying when I'm through with you."

I gulped at the sound of that, then could only stare ahead as Mistress Syn walked around me, her boots tapped against the carpeted floor until she was standing behind me. Never in my life had I experienced any sort of corporal punishment, even a simple spanking from my parents, so this was going to be something entirely new.

"It's time for your lesson, sweetie... Just remember, you brought this on yourself."

Within seconds, the sting of the cane against my bare ass filled my body with pain, and I bit down on the dildo gag. Before I could even process it, it struck again, just barely grazing my balls as it nipped at my cheek. I could already feel tears beginning to form in my eyes, and Mistress Syn had only just started.

Two more strikes and the tears started to fall in earnest. "Oh, I forgot to tell you," she said with a giggle, "But one of those cameras I told you about? It's right above my bed. Smile for it Trinket."

I looked up and spotted a small red light above her bedframe, pointed right at me. Even if I were able to, I doubt I could have managed a smile in my current state, but just the idea that I was once more being recorded made me groan with shame as well as a small amount of pleasure.

Here I was, splayed out across her bed, dildo gag in my mouth, ass in the air being beaten by her cane, all on camera, and my cock refused to soften in the slightest. I'd never truly considered the idea that I would enjoy being humiliated in such a way, but the more Mistress Syn abused and controlled me, the more I liked it.

Her cane struck again, harder now, one on each cheek without letting up. I cried and moaned into the gag, and she giggled at my agony. "Mm, I love that sound Trinket. It's the sound of submission. Aren't you lucky you have Mistress Syn to teach you such important lessons?"

I muffled an almost unintelligible 'Yes', and she replied with another strike.

My eyes landed on a clock on her bedside table. We'd only been at this ten minutes, and my ass was already in more pain than I ever thought possible. And still, she continued her assault.

After ten more minutes and over a dozen more strikes, Mistress Syn stopped for a moment, but if I thought she was finished I was dead wrong. Instead, she walked over to a clothes hamper in the corner, dug around in it until she found whatever she was looking for, then made her way to where my head lay on her bed.

"Here Trinket, this should help you a little bit" she giggled, and I looked to see a handful of dirty socks in her hand. I could smell them almost immediately, but could do nothing but watch as she shoved plopped them in front of me and pushed my face into them. "Take a big whiff sweetie."

Like it or not, I did so, and the strong stench of sweaty, dirty socks filled my nostrils and stung my eyes, causing even more tears to fall. I didn't know how long these had been rotting there in that hamper, but it was long enough that they made the smell I'd experienced during my first 'lesson' seem quaint.

Then she walked back to the end of the bed, picked up the cane, and got back to it. Within two minutes Mistress Syn had begun a rhythm, one strike per cheek, five times in a row, then a short rest before starting it up again. My ass ached and my nose burned but I could do nothing but lay there and take it, my cries and screams continually muffled by the gag as well as the pile of socks my face was buried in.

And still, precum leaked from my erect cock. After such an assault I would have sworn it would have finally gone flaccid, but it refused. Instead, it grew, feeding off the abuse being heaped on the rest of my underside, and I hoped that wherever it was dripping, Mistress Syn wouldn't notice.

After nearly ten more rounds, scarcely a half hour since we'd begun, she stopped. My ass ached, would likely be black and blue for some time, and tears trickled out of red eyes and down my face, leaving little drops on the gag and the socks beneath.

"So, did we learn our lesson Trinket?" Mistress Syn asked as she made her way over to my head and pulled it free from the socks before removing the gag.

I struggled for a moment before answering with the most pathetic tone I think I have ever used. "Yes, Mistress Syn.."

"Hmm, I don't think you have," she continued, grabbing my chin hard and moving my tear-stained face up to face her. "What did you learn?"

With a sigh, I replied. "To clean up my messes and always bring a tribute for you Mistress."

She smiled a cruel smile as she undid the restraints and freed me. "Good Trinket... Not you get to prove it."

For a moment I didn't know what she was getting at, but once she re-attached the leash and pulled me up and towards the end of her bed, where Mistress Syn pointed to the spot my legs and cock had previously been hanging.

And more importantly, to the puddle of precum resting on the pair of filthy socks she had placed there without my knowing.

"Open your mouth bitch," she commanded while pointing to the floor, picking up the socks and holding them in front of my face even as I dropped to my knees. "You're going to clean these right fuckin now."

My eyes widened as she shoved the socks inside my mouth, the acrid taste of her sweat, accumulated dirt, and my own salty precum making for a disgustingly strong cocktail. I wanted to spit them out, but the look on Mistress Syn's face told me in no uncertain terms that if I dared do such a thing another lesson would follow, and given how much my backside already ached, I doubted I could manage another one today.

So I sucked.

Sucked on those filthy socks like a lollipop, even as the filth filled my mouth and dribbled down my throat. Mistress Syn sat down on the bed and watched me with a wicked smile, the leash still in her hand as she used my mouth as her own personal washing machine.

It took almost a half-hour before she let me stop, and by then all I could taste was her socks. My taste buds were aflame with the disgusting aftertaste, and even when I opened my mouth and presented the socks to her, I had my doubts I would ever be able to rid myself of the memory of them.

"Not bad," Mistress Syn said, looking over my handiwork before tossing the socks into the pile with the rest and returning her attention to me. "But the maid's outfit will need to be properly cleaned. Bring it to a professional and make sure they get every trace of your pathetic precum out of it. I don't care how much it costs, you will get it done. Understand?"

I nodded. "Yes, Mistress Syn."

Rising from the bed, she led me by the leash over to her clothes hamper, the smell of filthy clothes strong even with the lid closed. She then reached inside and dug around until she found a pair of well-worn red panties that caught my attention not simply due to how sexy they looked, but how dirty. I could clearly see stains all over them and shuddered at what she had in mind for them.

"I'm not sure when your next in-person lesson will be Trinket. I have exams next week, so you'll have to do some hands-on learning." She giggled at her own words, though I wasn't sure what she was getting at just yet. "You are going to edge that pathetic little dicklet of yours every day while sniffing my dirty, sweaty panties."

My heart sank and my stomach turned. My head was still reeling from the scent of Mistress Syn's socks, the thought of having to sniff her panties made me shudder. While they would perhaps smell a little better than her socks, it was the principle of the matter.

But she didn't seem to care.

"I want you to stroke that little cock over and over and over and over while you sniff them, thinking about my sweet pussy and perfect ass. Neither of which you will EVER get to experience. Little whores like you have to make do with Mistress Syn's scent and nothing more. Oh, and don't you dare cum. If you do, I will beat your ass again, and I won't go as lightly next time."

The fact that she considered what she had done to me 'light' terrified me, and my eyes moved towards the other tools which she had chosen not to use on me today. I didn't want to experience any of those anytime soon, or ever. That meant I had to do as she ordered.

"Yes, Mistress Syn."

She led me out of the bedroom by the leash, pulled a small Ziploc bag from a cupboard and slipped the panties inside. Then she undid the leash, removed the collar and kicked my extremely sore ass. "Put your clothes on and get the fuck out of my sight you little bitch. I have studying to do, and you have work to do."

Crawling over to the table by the door, Ziploc held tightly in my teeth, I slowly put on my clothes, jolts of pain coursing through me as my boxers and pants rubbed against my aching behind, much to Mistress Syn's amusement. Then I slid the bag into my pocket, opened the door and left, the memory of my punishment fresh in my mind as well as on my ass.

While my next lesson might not be for some time, I would not forget this one. Nor what it had taught me.

Mistress Syn not only owned me, but she could make me suffer in more ways than one.

And most importantly of all, that I enjoyed it.