Sinful Tutoring: Lesson Nine

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

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The week dragged on, but before I knew it, Friday at last arrived, and with it, whatever new lesson Mistress Syn had in store for me.

As ordered, I continued to watch the contents of the USB drive she'd given me three times a day, each time feeling more and more pathetic even as my cock strained against the confines of its cage. My traitorous member was truly enjoying reliving the torment of my previous lessons, even as the rest of me could scarcely fathom just how fucked my life had become.

There was just something about watching everything Mistress Syn had done to me that really hammered in the humiliation. It would be bad enough to simply remember it from memory, but to have to watch it all play out over and over on screen made it all the worse, as well as more real. There was no escaping the truth. Mistress Syn had me by the balls, in more ways than one.

Even so, late that afternoon when I received a text from her, part of me still shivered with a twisted anticipation at what was coming next.

The text consisted of a time, seven o'clock, as well as a number- 425, and I knew immediately what it meant. That didn't make me feel any better.

425 was a classroom number, one of the rooms in the nursing department across campus. I myself had never been there save for during a brief campus tour prior to my enrolment, but I knew the numbering of the classrooms and the buildings therein, and it quickly dawned on me that this was where I was to meet Mistress Syn and likely Jane for the latest of my lessons.

It had never occurred to me that whatever they had planned for me would take place on campus, in one of the classrooms, and now that it was, I was beyond nervous. While most classes had finished for the day, there always remained the distinct possibility of stragglers or staff or janitors hanging around the buildings.

Any number of people who could thus bear witness to my continued humiliation.

Still, I knew deep down I didn't have a choice. If I didn't go to that classroom tonight, Mistress Syn would ruin my life even more than she already had. Those pictures and videos would be released, and there would be nothing left for me but never-ending humiliation.

That said, a small part of me- the optimistic part if you will, clung to the vain hope that perhaps Mistress Syn would choose to unlock my cage and set me free tonight, both from my chastity as well as my servitude to her.

I doubted either possibility was in the cards, but it didn't hurt to hope.

A little before seven, I made my way across campus, making sure to stop by the ATM to withdraw a fairly large tribute for Mistress Syn, then headed for the nursing building. Even as it came into view, my mind reeled with worry as to what sort of lesson she could have in mind for me inside, as well as what would happen if anyone spotted us.

Outside the door, I took a deep breath and then headed inside. It was silent, the halls empty and dark, but at least no one else seemed to be hanging around. That was a plus. It took me a few minutes to find room 425, but eventually it came into view. Inside I could see a light, and though I was terrified about what awaited me, I knocked and waited.

After a moment, the door opened, and my eyes widened at what I saw.

Room 425 was a fully stocked medical examination room, much like one would find at a clinic or the hospital. And waiting inside for me, decked out in scrubs, were Jane and Mistress Syn.

Jane wore a pair of light blue ones which covered her body save for her bare feet, which she seemed to be showing off proudly. Mistress Syn, on the other hand, wore dark purple scrubs which matched both her hair and her makeup. Both of them eyed me with wicked smiles and as I stood there staring, I knew I was in deep trouble.

"Looks like our patient has finally arrived," Mistress Syn said with a smile. "Shut the door behind you and lock it Trinket."

I did as she ordered, feeling slightly better knowing the door had a lock, even though there were likely countless people on staff who would have a key. Then I placed the tribute on a nearby counter and dropped to my knees, where I waited for my Mistress's command.

"I don't know if you know this Trinket," Mistress Syn continued, stepping towards me, "but I'm in my final year of nursing. This week, we learned ALL about proper prostate health, and that got me thinking...."

My eyes widened at the mention of the word 'prostate', and almost immediately, I had a bad feeling I knew just what she had in mind. Something Mistress Syn quickly confirmed. "With finals coming soon, I figured I could kill two birds with one stone. Get some real hands-on learning, and give you your next lesson. Isn't that smart Trinket?"

I groaned in despair but knew I had to answer her anyhow. "Yes, Mistress Syn."

"Ah ah ah," she said, bringing her booted foot right in front of me with a thud. "Today you will refer to me as Nurse Syn, is that understood?"

With a gulp, I nodded. "Yes, Nurse Syn."

"Good patient. Now, take off your clothes and crawl over to the examination table."

As was the norm, I removed my clothes and placed them to the side, then knelt there bare-naked for a moment before crawling across the tiled floor towards the table beside which Jane and Mistress- or rather, Nurse Syn, were waiting. And once I got there, I stood up for the briefest moment before planting myself on the table.

"On your hands and knees," Jane began, and I positioned myself in such a way. I felt more embarrassed than normal, especially as my caged cock hung between my legs, where both Jane and Nurse Syn spotted it and giggled. "Hmm, the patients' balls seem awfully full Nurse Syn," she continued, poking at my swollen testicles.

"That's to be expected," Nurse Syn added, almost matter-of-factly. "If the patient has been doing his homework his balls would certainly fill up quickly with all that useless loser semen. And from the look of these, he certainly has been doing his homework regularly. Haven't you Trinket?"

"Yes Nurse Syn," I replied sadly. "Three times a day as you commanded."

"Such a good little patient you are," she said with a laugh as she poked at my caged cock. "Emphasis on the 'little' of course."

The two of them laughed out loud and my face turned red even as my cock began to grow within the confines of its cage once more. I hated the fact that such humiliation made me hard, but such was the power of Nurse Syn and the thoroughness of her lessons.

Once their giggles died down, Nurse Syn walked over to a nearby cupboard and removed a small box and bottle, then brought them over to the examination table. My eyes widened when I realized just what they were- latex gloves and lubricant. Even though she had told me what her plans for me were, somehow seeing the tools she planned to use made it all the worse.

"Nurse Jane, I believe our patient will require some extra treatment before we proceed... Have you prepared the foot treatment for him?"

"Yes, Nurse Syn. Just as you asked."

Jane leaned over by my ear and grinned. "I haven't washed my feet or socks all week. Just for you."

I groaned at the thought of Jane's filthy feet, but before I could do anything about it, Nurse Syn slid on a pair of purple latex gloves and snapped them, bringing my attention back to her even as Jane took a seat by the head of the examination table.

"Nurse Jane, begin foot treatment while I lube up."

The command had scarcely left Nurse Syn's mouth before Jane brought her legs up and planted her soles over my face, and almost immediately the smell of her feet shot through me like a bullet to the brain. They reeked, even more than Nurse Syn's had during some of our previous lessons, and the sweat and grime that had built up over the past week began to smear against my skin, forcing its way into my nose.

It took everything I had not to pull back in disgust, but I knew if I did I'd be in trouble. Much as it pained me, my only choice was to take it.

Just as I was about to take something else.

"I know you can take a cock up here," Nurse Syn said from behind me, rubbing a cool, lube-covered gloved finger around my asshole. "Let's see how you do with a finger."

Before I could react, I felt that cold, latex finger poke its way into my ass, and the unexpected sensation forced my body forward, shoving my face even closer to Jane's feet. She laughed, pushing back in kind so as to keep me in place, all the while Nurse Syn's gloved finger began to explore the nether regions of my anus.

"You see Trinket, the prostate is a gland found in the rectum. If you massage it properly, it can be highly beneficial to your health..." Her latex-gloved finger began to rub around inside me, seeking out its prey as she continued her explanation. "It's about two inches in and feels like a lump. At least, it'll feel like that to me. To you, it'll feel like-"

Deep inside my ass, her finger poked at something never before poked, and my body tensed up even as I practically yelped into Jane's feet.

"To you, it'll feel something like that," Nurse Syn added with a giggle, then continued to rub the spot with her gloved finger.

Odd as it seemed, this felt altogether different than when she had fucked my ass with her strap-on. Perhaps because that time, my focus had been on trying to deal with the dual assault on my mouth and ass courtesy of her and Jane. I was able to distract myself from one by focusing on the other, even if only for a moment.

With her finger playing around in there, I had no such luck. I felt it and only it, and Nurse Syn was only getting started.

"What's interesting is that, if someone has emptied their testicles in some time, a proper prostate massage can force semen out."

My eyes widened beneath Jane's stinky feet for the briefest of moments as I considered the possibility that I was at long last going to have a chance to cum properly for Nurse Syn. Alas, such hopes were just as quickly dashed as her other hand cupped my caged cock.

"Without any pleasure Trinket."

Then she and Jane laughed as the brief spark of hope in my eyes faded away. They were going to let me cum yes, but not in any way I would enjoy.

Even as that thought sunk in, I felt another gloved finger slip inside my asshole and join its friend, both of them slowly massaging the lump that was my prostate. And as they did, Jane slipped her right foot down my face, leaving a trail of sweat behind as her toes stopped at my lips.

I knew what she wanted, but prayed I was wrong.

"Say 'ahh' Trinket,' Jane said as she poked at my mouth. "These toes need to be sucked for the treatment to be successful."

"Excellent point Nurse Jane," Nurse Syn added. "You heard her Trinket. Open your mouth and suck on those sweaty toes."

Much as it pained me to do so, I opened my mouth and let Jane's filthy feet slip inside, the acrid taste of accumulated dirt and sweat overpowering my taste buds even as her other foot continued to rub against my face and torment my nose with its horrid scent.

"Hmm, you're taking two fingers quite well," Nurse Syn mused as her fingers moved back and forth and side to side within my rectum. "I wonder if you could take my whole fist."

A shot of fear coursed through me as she said that, much to her and Jane's shared glee. Both of them laughed as I turned red once more, this time from the assault on my senses as well as the sheer terror of being fisted, and only when their laughter died down once again did Nurse Syn take it back. "Don't worry Trinket. That wouldn't be beneficial for this particular treatment... But another finger might."

The cool sensation of the lube covering it did little to make me feel better as a third finger slipped inside, aiding the other two in raking their way across my prostate. I groaned through Jane's toes and she quickly switched feet, shoving the ones on her left foot inside while her right one took its place covering my face.

I don't know if it was the continued feeling of Nurse Syn's slick gloved fingers toying with my ass or the awful smell and taste of Jane's filthy feet on my face, but my cock- which had already been straining against its cage, was beginning to throb in a way I'd almost forgotten it could.

A way that used to be a good sign.

And that's when I heard it.

A drop.

Though I couldn't move my head to look with Jane's feet holding it in place, it was impossible to ignore the fact that something had dripped into something else, and it didn't take me long to realize what. Nurse Syn's 'treatment' was starting to work, and the more she worked my prostate, the more drops I heard, until after several seconds, they were replaced by what sounded like a fairly steady stream.

"Oh my God, look at that!" Jane said with glee as she finally lowered her feet from my face.

I struggled to breathe for a moment or two before taking the opportunity to move my head down to see what she was referring to. And when I did, I groaned with despair.

My cock was sending out a seemingly endless stream of cum, yet I barely felt a thing. No pleasure, nothing resembling an orgasm. Just an almost clinical emptying of my balls into a bowl which rested between my legs on the examination table.

"As I said Nurse Jane, proper prostate manipulation relieves the pressure without offering any pleasure... And it looks like our little patient had a LOT of pressure built up."

She let out a wicked laugh as her fingers continued to milk my prostate for all it was worth, her other gloved hand holding the cage steady so that my semen kept flowing into the bowl. All I could do was watch as the stream poured out from the caged tip of my cock with growing despair.

If I thought I'd been humiliated before, I was dead wrong.

The fact that I'd finally been allowed to cum, yet been denied any and all enjoyment that would normally come along with such a thing was bad enough. That it happened while Nurse Syn's gloved fingers were in my ass manipulating me like a toy and Jane's stinky feet were pressed against my face made it all the worse.

Yet none of that compared to the fact that I'd also never felt so horny in my entire life.

Somehow, being denied pleasure while still being drained in such a way as this left me longing, and I was beyond aroused. Not even when I sat there watching the videos Nurse Syn had taken of all our previous 'lessons' had I felt this way, and I struggled to understand just what it meant.

As the stream of semen began to taper off at last, Nurse Syn removed her fingers from inside my rectum and smacked my caged cock while she held the bowl right below it, making sure she got every last drop out. Then she slipped off her gloves and tossed them in a nearby waste disposal container and watched with glee as my cock began to return to its normal pathetic caged state.

I groaned with desire and denial as she stepped around to the head of the examination table where Jane stood waiting, a familiar phone in her hand filming. Nurse Syn's phone. I wasn't sure if she'd been filming the entirety of our lesson or just this part, but in truth, it didn't really matter. Whichever it was simply meant more blackmail material for Nurse Syn's ever-growing list of it.

"Very good Trinket," she said with a smile as she slipped on a fresh pair of gloves. "You were such an obedient patient, I think you deserve a treat." She ran a gloved finger across my sweat-covered lips as my eyes looked up at her. "Too bad I'm out of lollipops!"

She laughed in my face, and I sighed as she reached under me and took hold of the bowl, bringing it all the way to the front of the examination table. Only then did I realize what was expected of me, and even my over-aroused mind shuddered at the thought of it. "Eat up Trinket!"

With a sigh, I lowered my head towards the bowl, Nurse Syn pushing me down when she decided I wasn't moving fast enough. Then she held me there while my tongue slipped out and I began to lap up my cum like a dog, licking it out of the bowl while she and Jane laughed and filmed.

They kept the camera on me until I licked the bowl clean, and then Nurse Syn took it away and ordered me off the table.

Once I was back on the floor, she pushed a boot-covered foot towards me. I didn't need to be told what was expected of me, simply pressed my lips towards it and kissed the toe of her boot until she was satisfied.

She walked over to the counter and picked up the tribute I'd brought along, then shook her head. "You know what Trinket, I think I deserve an extra tribute after today's lesson. I mean, your pathetic little dicklet finally got to spew its loser load on purpose for a change."

I nodded. "Yes, Nurse Syn."

Then I started to put my clothes on, Jane and Nurse Syn watching me with disgust, but I knew they weren't simply going to let me leave.

And I was right.

"I don't know when your next lesson will be. Finals are coming up, and those are WAY more important than you'll ever be... But until then, I expect you to do your homework-"

"Five times a day" Jane interrupted, and Nurse Syn nodded.

"Yeah, five times a day sounds right. I want those balls so full they make your dicklet look even smaller!"

"Is that possible?" Jane asked, stifling a giggle that turned into a full-on laugh at my expense.

A groan escaped my lips. Three times had been rough, five would be downright brutal. Yet I knew just as they did that I would do it without question.

"Don't worry, I'll be sure to send you this one as well. Just so you'll have something new to torment yourself with. Aren't I so sweet Trinket?"

"Yes, Nurse Syn."

"You are so good to him Mistress," Jane said, wrapping an arm around Nurse Syn. "So kind to teach him all these important lessons."

Nurse Syn smiled and kissed Jane, then broke the embrace with a smile. "I know. I just can't stop giving."

They broke into a fresh round of laughter, then pointed at the classroom door. I unlocked it and left, drained and humiliated and still so damn horny that I knew that were I given the chance, I'd have begged them to do it to me all over again.

And that scared me even more than the idea of Mistress Syn releasing all the videos and pictures she'd taken of our 'lessons'.