Sinful Tutoring: Lesson Six Six Six

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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As I knelt there on the floor of Mistress Syn's dorm, the taste of my precum still fresh in my mouth, I wondered just how things could possibly get worse.

Honestly, after everything else that had happened, this really seemed to me like the peak of humiliation. Having Mistress Syn not only put my sweet classmate Jane through the very same ordeal she'd put me through was one thing, but being forced to listen to her fuck her while I wasn't even allowed to touch my cock? It seemed beyond cruel.

For the first few minutes after they'd gone into her bedroom, there was only the sound of Jane's footsteps and Mistress Syn's boot heels on the carpeted floor. Then came a few sounds I couldn't quite put my finger on, but I assumed were Mistress Syn getting ready to fuck Jane.

And then, just when I thought they were going to drag it out as long as they could, the creaking of bed-springs rose up and filled the air, followed by heavy breathing and the pounding of flesh on flesh. Even without seeing it myself, I knew what was going on just down the hall.

Mistress Syn was fucking Jane for all she was worth.

Outside of porn, as well as a very loud dorm neighbour I'd had in my first semester, I'd never had to other people having sex, and even then, had never truly realized just how humiliating it could be. Knowing that there were two beautiful women just down the hall having sex, and all I could do was listen to it? I felt so damn pathetic there weren't even words to describe it.

And still, through it all, my cock stood at attention. Loving every second of it.

The more I considered this, the more frightened I became as I realized how quickly Mistress Syn had taken control of me and my cock. The fact that something like this was more than enough to keep me both erect and on edge simply because she was involved? That was downright terrifying.

As the sounds grew louder, moans joined in, adding to the cacophony in the air, the soundtrack of my continued submission. Mistress Syn wasn't one to take her time it seemed- she was showing Jane, and by extension me, who was boss. And when those same moans became a scream, I knew the lesson had been learned by one of us.

But it was far from over.

Within seconds of the screams dying down, the bed-springs were moving again, and the whole ordeal started up once more. Mistress Syn wasn't giving Jane the chance to recover, instead doing exactly what she'd promised. Giving her a fucking I could only dream of giving either of them.

And knew I never would.

Even if my fortunes suddenly changed for the better, I knew I could never hope to satisfy either Mistress Syn or Jane.

The clock on the wall ticked by, eclipsed over and over by the sound of Jane's seemingly-endless climaxes. I lost count of how many orgasms Mistress Syn forced out of her, or how many she had herself simply from asserting her dominance over the other woman, but I knew they were both far more than I had ever given a woman. The cries and moans echoed out in my head, and I thought I would start to cry from the mix of them and my continued denial.

As the latest one subsided, however, I heard something else. The sound of Mistress Syn's boot heels on the carpeted floor of the bedroom heading towards the tiles of the hallway. She was coming for me, I was sure of that, but I still dared not look up to be sure.

Only when the sight of those boots plopped in front of my lowered head did I know for certain, and by then it was too late for me to do anything even if I'd wanted to.

Looking up, I noticed the sweat glistening off her body from the effort of continually fucking Jane, as well as the long, thick, black rubber phallus she'd used to do it. The strap-on was truly drenched, covered with Jane's juices as well as Mistress Syn's own, the entire thing a testament to just how many orgasms they'd each had.

My mouth watered at the sight of it, even though I knew I would never have the opportunity to taste them.

"Did you enjoy that Trinket?" She asked crudely, her lips smiling as wickedly as could be. "I hope so... Your little friend definitely did. That was probably the best fucking she's ever had."

I groaned, knowing she was likely right, as well as reading between the lines. She was reminding me, in no uncertain terms, that she was in charge, and that she had fucked Jane better than I could have even if I'd made it that far. It was cruel, it was emasculating, and it was one-hundred-percent true.

Had she only intended to reinforce that, it would have been enough to break me even more than I already was, but Mistress Syn was only getting started. "Well, the night is still young, and I have more planned for you. After all, you still need to learn your lesson, don't you Trinket?"

"Yes Mistress Syn," I uttered defeatedly, my head hung low as I tried to figure out what was left for her to do to me.

"Good boy... Follow me."

She headed back towards the bedroom, and for a moment I dared not move. After what had happened the last time I'd been in there, the idea of going back scared the shit out of me. Even so, I knew better than to keep her waiting, and quickly crawled on all fours into Mistress Syn's bedroom.

Once inside, I noticed Jane sprawled out on the bed. She too was glistening with a mix of sweat and her juices, face flush as she gasped for breath. Her pussy was beyond drenched, and I could see splashes of her cum all over the sheets. She'd certainly enjoyed herself.

Mistress Syn walked over to her and grabbed her by the hair, but unlike when she'd done similar to me, she pulled Jane up and planted a deep kiss on her lips.

Jane's eyes closed and she let out a small moan, fanning the flames of jealousy that had been sparking ever since she'd been granted the opportunity to lick Mistress Syn's pussy earlier. Though she too was a sub like me, it appeared she was getting far more preferential treatment than I was.

Breaking the kiss, Mistress Syn picked up Jane's leash and lead her off the bed and to her feet. With the boots on she towered over the other woman, yet as I remained on my hands and knees I felt like an ant in front of the two of them.

Jane looked down at me with a look of complete and utter disgust, likely due to both my getting her into this as well as seeing just what I was willing to do for Mistress Syn. Debasing myself over and over again for her amusement wasn't exactly the sort of thing that would endear me to someone like her.

"Come here Trinket," Mistress Syn said, patting the spot on the bed where Jane had only moments before been laying. "Crawl up here and get on your hands and knees for me."

I did as she commanded, even less sure what she had in mind for me than I already was, but the moment I assumed the position, I watched her hand Jane a strap-on of her own- a big, long, white rubber one, my eyes widening as hers filled with the same wickedness as Mistress Syn's.

Jane slipped the harness on and grabbed hold of the rubber cock now attached to her, a small smile spreading across her lips as she stroked it. Then she walked over towards my head while Mistress Syn made her way around the bed and stopped by my ass. She suppressed a giggle as she took in the sight of her previous handiwork, the marks faded but the memories of my punishment were still fresh as could be.

"I hope your ass missed me Trinket, because it's about to feel what your little friend did. And so you don't say a word, she's gonna do the same to your pathetic whore mouth. Open wide for her!"

Much as I didn't want to, it was clear I had no choice. Shutting my eyes, I opened my mouth and felt the tip of Jane's strap-on slip between my lips. Her hand then grabbed at my hair and pulled, and I heard her whisper. "Open your fucking eyes. I want you to watch."

Mistress Syn laughed. "You're coming along so nicely my little slut."

Jane smiled at the praise and let go of my hair. With a sigh, I opened my eyes. Watched the rest of the rubber phallus push its way into my mouth a little bit at a time. And before I could truly appreciate that, I felt Mistress Syn slip hers between my ass cheeks. It felt so wrong, so uncomfortable, that I wanted to scream, but Jane's cock made sure the only sound that came out of my mouth was a muffled "Ug."

"Mmm, you're so lucky I fucked her so many times," Mistress Syn teased from behind. "Means this thing is all lubed up for your... It slips in SO easily now..."

I groaned as Jane's strap-on slid in and out of my mouth, never pulling out fully but making sure she got as much in at a time as she could. I don't know if it was her first time doing anything like this, but she certainly acted like a pro, slowly fucking my face for all it was worth.

Humiliating as that alone would have been, with every slow thrust, I could smell her still-soaked cunt behind the rubber of the strap-om. And while I should have enjoyed that- especially compared to the other things I'd been forced to smell since falling under Mistress Syn's s way, the fact that I couldn't taste her, never would be able to, and knew that someone else had made her cum this hard... It removed any and all joy I could have gleaned from the experience.

"Mmm, that's right sweetie, fuck him real good. He's such a little whore, isn't he bitch?"

Jane looked up and Mistress Syn with a grin, then looked down at me, making sure her eyes were staring into mine as she spoke. "Yes, Mistress Syn. Such a pathetic little whore..."

Much as I wanted to shut my eyes, especially after hearing that, I dared not, and thus could only look at her as tears formed in my eyes from the dual assaults on my body and my nearly non-existent self-esteem. The continued humiliation from both these women was insane, and I felt like an honest-to-God whore. Only there to be fucked one way or another, and the more their twin strap-ons fucked my holes, the stronger that feeling grew.

As did my cock.

The fact that being fucked at both ends did not diminish my erection in the slightest further compounded my humiliation, and I felt even lower than I already had. A part of me was truly enjoying being used in such a way, and there was nothing I could do about it.

Mistress Syn seemed to notice, and upped the tempo on my ass, fucking it a little faster with each thrust before slowing down again. Every time the cold, pussy-drenched harness grazed my still aching behind, I had to hold back more tears, but it was plain for both of them to see that I was crying like a little bitch.

And they were loving every minute of it.

"Aww, poor Trinket... Here I thought you'd LOVE getting fucked by us... I mean, it's not like your pathetic little dicklet could ever hope to fuck either of us this good..."

"It's so pathetic Mistress Syn," Jane added, staring at my erect cock as it swung back and forth under my body while they fucked me. "Thank you for saving me from ever having him stick it in me."

Mistress Syn let out a maniacal laugh that shook the cock jammed in my ass, and she pulled it out just enough for me to believe for a moment she was finished with me. But she was only steadying herself and shoved the entirety of the strap-on back inside me a moment later. "You're turning into such a dirty little slut," she praised, staring at Jane across the bed. "I am definitely gonna keep you."

Jane blushed then grabbed my head with both hands to make sure I took every inch of her cock. I practically gagged as the tip of it grazed the back of my throat, but she did not let up in the slightest, nor did Mistress Syn. Her cock did the same, the tip deeper than I thought was possible.

The two of them seemed to sync up, keeping in time with one another as they slipped their strap-ons in and out. I shut my eyes for a moment, trying to force myself to get my head on straight in spite of my circumstances. I was beyond fucked- both literally and figuratively, but I wanted to at least try and keep a shred of my fading dignity. I'd already cried more than once, I couldn't humiliate myself any further.

Unfortunately for me, my cock had other plans.

Maybe it was the sensations in my mouth and my ass. Maybe it was the scent of Jane's pussy juices wafting into my nose with every new thrust. Maybe it was their taunting and teasing words or everything that Mistress Syn had said and done to me since the start. But whatever the reason, the orgasm I'd been denied since this whole mess started was begging to spill forth from my aching cock and balls, and there was nothing I could do to stop it.

Everything that had happened leading up to this moment- from that first 'lesson' in my dorm to my kneeling in the hallway listening to Mistress Syn fuck Jane, filled my mind and replayed over and over in a seemingly endless loop as their cocks fucked my mouth and ass in time.

Precum had been dribbling out of my cock since they'd first shoved their strap-ons in my holes, and now it was flowing like a faucet. I knew what was coming, knew it would likely not end well for me, but also knew there was nothing whatsoever I could do but let it happen and hope for the best.

In an almost perfect crescendo, Jane's cock slipped in between my lips, pressing my face against the harness and forcing me to smell her wetness up close once more, and Mistress Syn's was shoved so deep into my ass that her harness once more made contact with the cane marks she'd left on me, and as they both reached their targets I felt my body begin to shake with a sensation I'd almost forgotten.

Biting down on Jane's strap-on and clenching my ass cheeks around Mistress Syn's, I gave in and let the feeling wash over me as my desperate, aching cock finally let loose with all the cum that had built up in my balls from the seemingly-endless edging and torment it and I had been through.

The orgasm burst free, sending streams of hot, white cum straight down onto Mistress Syn's bed, and still, I shook with pleasure as well as fear. Beneath the joy of the long-awaited release was the realization that I had disobeyed Mistress Syn, and such a thing would not be tolerated.

Even before my cock finished dropping its load, I felt Mistress Syn and Jane cease their assault on my holes, and I quickly understood why.

They were both pissed.

"You pathetic little whore!" Mistress Syn screeched, pulling her cock out and spanking my ass hard. I yelped, even though it was still muffled by Jane's- though not for long as she too removed hers and took a step back. She looked down at me and shook her head, any enjoyment I may have had dissipating as quickly as it had arrived beneath their anger and disappointment.

"You made a mess on Mistress Syn's bed," she said coldly, moving her eyes to the pool of cum on the sheet below me.

Mistress Syn spanked my ass once more, then again for good measure, before stepping around me to stand by Jane. "He did indeed. Such a naughty Trinket. I told you you weren't allowed to cum without my permission. And you did anyway. You know what that means?"

I looked up at the wall behind them. At the cane, the paddles, and other toys she kept for such occasions. "Yes, Mistress..." I replied sadly, knowing there was nothing I could say or do to prevent my fate. "I need to be punished..."

That alone would have been bad, but Jane had another idea. "I think he should clean up his mess first Mistress Syn..."

"Oh, I agree," Mistress Syn replied, and my stomach dropped at the thought of licking up all of that cum. "It's only right."

But Jane wasn't finished.

"Could he... Could he lick it off our cocks?"

The look in Mistress Syn's eyes was hard to describe, a mix of ecstasy, wickedness, and more than a little pride. "That's fucking hot you little bitch... I think that's a great idea."

Mistress Syn pointed to the floor, and I crawled off her bed, trying not to touch my mess even as the thought of what they had just agreed upon made me ill.

I watched as Mistress Syn and Jane walked over to the puddle and slowly slipped their strap-ons into it, making sure to coat every inch of the rubber with my warm cum until they were both glistening beneath the fairy lights of the bedroom.

Then they stood before me, cocks in front of my face, and shoved them towards me. "Open up Trinket," Mistress Syn commanded, and I did, opening my mouth and taking her cock in my mouth. In and out she slid it, making sure to coat the inside with my juices. "Get your tongue into it whore. I don't want a drop of your loser load left behind when you're finished."

Jane smiled beside her, watching with academic interest and glee as I sucked Mistress Syn off and cleaned my cum like the pathetic whore I clearly was.

After a few minutes, Mistress Syn pulled out and went back to the puddle on the bed for more, leaving Jane to shove her cock into my mouth in its place. I did the same with hers, sucking and licking up my still-warm juices and fighting back another round of tears.

They alternated, one cock at a time, making sure they got as much of my cum as they could off the bed and into my mouth. I gazed up at one point while I sucked Jane's off and watched Mistress Syn lock lips with her once again, making out while I knelt there with a cock in my mouth.

If there was a moment in which I truly felt as low as I possibly could, that was it.

The sight of them kissing deeply while I sucked one of their strap-ons clean would remain burned forever in my mind.

And worst of all was knowing they weren't through with me yet.

After all, my punishment still remained.