A Private Lesson You Wont Forget 09

Not long after a silent dinner was held, and though neither Miss Scarlet nor Miss More said a single word, that alone spoke volumes.

You were in rather deep trouble.

To be fair, you'd been in trouble from the very start. The moment you'd laid eyes on Miss Scarlet and decided to be a proper little arse to her rather than simply keep your mouth shut. And ever since that fateful day, everything you'd done, everything that'd been done to you, and been solely to teach you a lesson.

One it appeared you still hadn't manage to learn.

When the meal ended, you pulled out their chairs and held open the door for them just as you had the previous days, but neither woman as much as acknowledged your existence. They simply walked out of the dining room, down the hall and up the stairs as if you weren't there at all.

You followed a few seconds later, yet by that point they were long gone, and you crawled into the guest room alone, head hung low and mind reeling with worry about what was coming for you. After everything you'd been put through since your arrival, what else was there left for them to possibly do?

The study break itself was winding down, but there was still plenty of time for Miss Scarlet to teach you a little more.

When morning came around, a loud knock on the door roused you from your uneasy slumber, and you rolled out of bed and onto the floor before opening it as wide as you could.

Miss Scarlet was waiting on the other side.

As she had before, she was dressed in a robe, with only the smallest glimpses of her gloved hands- short black leather ones from the look of things, as well as her black leather heels, showing from beneath it. Your eyes moved from them to hers, and she gazed down out you with her hands on her hips.

"Good morning... Miss More and I have already eaten breakfast. Go and grab something to eat then meet us downstairs. I have a very special lesson planned for you."

Then she walked away, the clicking of her heels on the floor vanishing as she entered her room and shut the door. With a sigh, you began to crawl out of the room and down the hallway, knowing that nothing good awaited you downstairs but knowing after yesterday not to disobey Miss Scarlet.

Breakfast awaited you in the dining room, just as it had the past several days, prepared by the unseen staff. You ate alone, the silence only broken for a moment by the sound of Miss Scarlet and Miss more descending the stairs, opening the basement door, and heading down to wait for you.

Much as you wanted to take your time, you knew the clock was ticking.

Once your plate was clean you left it on the table, dropped back down to the floor, and headed out into the hallway. Gazing up at the basement door, you felt like a man heading for the gallows. You pressed an ear to it, in a vain hope that you might hear something that would provide you with an idea of what they were going to do to you down there. Alas, only silence greeted you.

Whatever it was would be a surprise. One you were not looking forward to receiving. With a sigh, you reached for the knob, turned it, and carefully crawled down the stairs into the waiting dungeon.

At first, you couldn't see either Miss Scarlet or Miss More anywhere. But once your hands and knees touched down on the cold floor, the former's voice called out to you. "Over here," was all she said, forcing you to figure out just where 'here' was'. The dungeon was vast, and you passed by several terrifying sights as you made your way along. A cage, the bench you'd been thoroughly spanked upon, canes and whips and strap-ons and countless other things you dared not even name.

After a few moments, you looked over and noted a small room off to the side with an open door and a light on. And upon crawling to it, you spotted three things.

Miss Scarlet.

Miss Moore.

And a chair.

Miss Scarlet looked incredible as always, with a shiny black leather skirt, glossy stockings and a pair of knee-high black leather boots. A sheer top showed off her lovely breasts- held back by a dark purple brassiere, a black tie hanging off her neck and nestling between her bosom. Shoulder-length purple leather gloves completed the ensemble, and along with her red-painted lips and lovely red hair cascading down her shoulders, she looked every part the strong, stern, domineering teacher you'd come to know.

Miss More had chosen a very similar look, with a longer black leather skirt which hung just past her stocking-clad knees, a pair of black patent leather heels adding an inch or two to her height even as she already towered over you. An olive green long-sleeved top vanished into a pair of elbow-length black leather gloves, and she watched you kneeling in the doorway with a grin.

And yet, lovely as the two wicked women standing before you looked, your attention was firmly drawn to the chair in between them.

At first glance, it looked to be a throne of some sort, which, given what you were quite certain the owner of this house- the eponymous Miss Vera, did for a living, came as little surprise. But upon closer inspection, you realized if it was, it certainly wasn't for her or either of the ladies. Several restraints could be seen on the arm rests, legs and back, and the seat appeared to be a little shorter than one would expect.

"Come in," Miss Scarlet said, beckoning you closer with a purple-gloved finger, and you did as she commanded, crawling towards her, Miss More and the waiting chair. Once you reached them, she pointed to it, and with a gulp, you rose to your feet and took a seat.

As expected from your initial glimpse, the seat was indeed a little short and, much to your surprise, your cock and balls hung off the edge of it. Before you could begin to process that, however, the two women began to wrap the restraints around your arms, legs and waist, and within minutes, you were firmly attached to the chair, with no hope of escape.

Confident you were well secured, Miss Scarlet and Miss More pulled some nearby stools closer to the chair and sat down, the latter placing a bowl on the floor beneath the chair. Even seated they managed to tower over you, and though you shrunk beneath their gaze, their eyes were focused almost entirely on your already rather hard cock.

"Now then," Miss Scarlet continued, looking from you erection to your worried expression, "I had another lesson planned, as you well know. But seeing as your failed the previous one, I felt something else was required."

A shiver ran down your spine as you recalled how cross she'd been the day before, and you worried and wondered and what this new lesson would be.

"I've thought long and hard about this," she added, emphasizing the words long and hard as she spoke, "and I've decided it is the only way you're going to learn."

Miss More picked up a small leather ball gag from a table behind the chair and slipped it into your mouth. "So you keep quiet," was all she said, and once it was secured around your head, it was clear you wouldn't be saying anything anytime soon."

"Very good," Miss Scarlet said, her purple-gloved hand moving down to your exposed member and allowing a single finger to touch it. Your cock immediately began to flail about uncontrollably, in a desperate need to feel her gloves once again. "I told you before, I believe in positive reinforcement... But it seems that isn't enough for a naughty student like you... It appears you require something far more drastic. A firm touch if you will."

Across from her, Miss More smirked, and though you weren't sure what she was getting at, a part of you desperately wanted to find out. Given the positions you were all in, as well as the fact that no toys or tools could be seen, you couldn't figure out what they were going to do.

And then, without warning, you got an idea.

Miss Scarlet's gloved hand returned, took hold of your cock, and began to stroke.

The unexpected sensation caused you to stiffen up in your seat, but with all the restraints, you couldn't move all that much. Instead, you struggled for a moment before forcing yourself to settle down and take it, your teacher-turned-tormentor's gloved hand slowly moving up and down your shaft.

This was not what you'd expected at all, but you intended to enjoy it.

As with every time before, the sensation of her gloved hand on your body was amazing, and you groaned with pleasure from behind the gag as Miss Scarlet took her sweet time moving it along the length of your shaft. If this was to be your punishment, you'd gladly accept it.

Your eyes moved over to Miss More, who was still sitting across from the other woman. But in the time since Miss Scarlet had begun the lesson, her colleague's gloved hand and slipped beneath her leather skirt and, though you couldn't see what she was doing, the small moans already slipping free from her own lips told you enough.

Miss More was getting herself off while Miss Scarlet teased you, and the sight of that made your cock even harder. The purple-gloved hand wrapped around your shaft continued to gently stroke, making you groan even louder even if the sounds were muffled behind the gag.

This didn't seem like a punishment. It felt more like a reward.

Which should've been your first clue that things weren't what they seemed.

Alas, in that moment, such thoughts barely had the chance to enter your mind, so focused were you on the sights and sounds of Miss More playing with herself and the sensations of Miss Scarlet stroking your manhood for all it was worth. Everything felt so good, you would've given anything to stay in this moment forever.

However, the gloved hand slipping and sliding along your now-throbbing cock picked up its pace, spurred onward by the precum it had picked up from the tip along the way, and as Miss More's moans grew louder beside you, the same pleasure coursing through her began to rush through you as Miss Scarlet brought you to the very edge.

And pushed you right over it.

Your cock exploded, and her gloved hand expertly milked out every last drop, streams of cum pouring out and into the bowl beneath the chair. Miss More cried out in ecstasy as her own orgasm came to a head, and though her own gloved hand seemed to slow down beneath her skirt, the afterglow remained plastered all over her panting face.

Then she stood up, smoothed out her skirt, and switched places with Miss Scarlet.

Without a word, she took hold of your now-flaccid cock with her cum-drenched black leather fingers, and began to stroke it ever-so-slowly, spurring it back to life even though it clearly wanted nothing more than to take a moment to recover from the orgasm it had just experienced. Alas, no such luxury was afforded it, and instead, Miss More simply ran her gloved hand up and down your shaft just as Miss Scarlet had moments before.

At first, Miss Scarlet simply sat and watched, seemingly pleased with her colleague's eagerness. Once she seemed satisfied that Miss More was following her example, she did the same.

Right before your eyes, a purple gloved hand slid beneath her skirt, the other one making its way over to her breast, and all you could do was watch with wide eyes as Miss Scarlet began to massage her tit whilst simultaneously fingering her pussy with her gloved hands.

Never in your wildest dreams had you ever conceived of the possibility that you would be given the opportunity to watch Miss Scarlet do such a thing, yet much as you wanted nothing more than to watch her bring herself off, you found your attention forced back to your slowly-returning erection.

Miss More's black leather-clad hand had indeed brought it back to life, and to your surprise, she was drawing out more precum even though you'd only just cum. She didn't say a word, simply stroke your shaft with an almost clinic approach, and you were torn between her total dismissal of you and your erection and the absolute pleasure Miss Scarlet was seemingly experiencing beside you.

Her moans rang out in your ears, and just as with before, the strokes increased in speed. Before you knew it, the same sensation which had flowed through you only minutes before returned in earnest, and your cock began to spurt out globs of white, sticky cum.

Good as it felt, the fact that Miss More made sure that every last drop was milked out before she dared let go caused you a slight bit of discomfort, one which was quickly brushed aside as the groans of pleasure from beside you turned into screams. Miss Scarlet's face was as red as he name, and her purple leather fingers teased her nipple and clit with reckless abandon, leading her to cum in a way that made your own orgasms seem tame by comparison.

That said, you struggled to steady yourself- having two earth-shattering orgasms in such close succession somehow seeming even more draining that any you'd experienced before.

It wasn't as if the ladies hadn't managed to make you cum over and over again in the days prior- they most certainly had. But those times had been tempered with much less desirable outcomes. Somehow, experiencing such a thing without also being spanked, fucked, or forced to worship their boots, made the whole thing feel a whole lot different.

Yet just as with those times, they had only just begun.

You watched as Miss Scarlet and Miss More switched places once again, and almost immediately, a purple-gloved hand wrapped around your thoroughly spent shaft. The sensation of the cool, smooth leather mixed with both your and Miss Scarlet's juices made you groan, and that was before she even started to stroke you.

This time, however, Miss More decided to join in the fun, taking hold of your balls and gently cupping them in her black leather-clad hand. Two gloves toying with you in such a way was incredible- or would have been, had you not already felt exhausted as could be from the two orgasms you'd already experienced.

Your teachers, however, did not seem to feel the same way.

They kept at it, stroking and teasing and toying with you even as your cock struggled to rise to the occasion a third time. After a few moments it managed, much to your surprise, but soon enough succumbed to the wicked whims of the women in charge of both it and you.

A third orgasm followed, only this one was less pleasurable than those which had come before. In fact, it felt as if your body was struggling not simply to find the means to do what was expected of it, but to enjoy it as well.

Which wasn't to say you didn't enjoy it- but as Miss More and Miss Scarlet switched places once again, you slowly began to realize that this wasn't the reward it had seemed at the start. It was indeed a punishment, one you could barely wrap your head around.

And once Miss More picked up your shriveled up, cum-drenched cock and stated to stroke it yet again, the groan that slipped out from behind the ball gag was not one of pleasure, but one of utter dismay.

Miss Scarlet chose to ignore your balls, instead running a gloved finger along your bare chest, stopping to tease your nipples as she'd teased her own, and though it felt good- or should have felt good, the longer she did it, the more torturous the whole thing became.

You gritted your teeth, bit your lip, and gripped at the arm rests as tightly as you could, but still neither she nor Miss More let up.

As the fourth orgasm poured out of you, tears began to fall from your eyes, and though you could not say a word, it didn't seem to matter. The agony beginning to course through your body was almost indescribable.

At least when they had spanked and fucked you, it was easy to focus on the pain- that made the pleasure of orgasm after orgasm tolerable. But now? Now that it was the only thing, you began to realize that it could be much much worse than anything else you'd experienced.

Miss Scarlet began to play with your cock and balls, and as she did, Miss More stood up and moved behind the chair. She clamped a leather-clad hand over your mouth and nose, and the scent of leather- mixed with both hers and your juices, quickly filled your nostrils even as her other hand picked up where the other woman's had left off, teasing your now quite sensitive nipples.

Never before could you conceived of anything like this- of a situation in which things which you should be enjoying were being used to pushing you in such a cruel way. Given the chance, you'd have taken a dozen more spankings, or a thick rubber cock in your ass again and again. Anything but this.

And still, they did not stop.

Six, seven eight, you soon lost count of just how many times the ladies forced your sore and aching cock to stand at attention and spurt out whatever meagre amounts of cum were left in your extremely spent balls. Your face was red from the effort as well as the continuous smothering from each woman's gloved hands, but they refused to leave you be. They simply started up again, and you had no choice but to sit there and take it, your moans and cries and pleas held back by the gag.

Yet that wasn't even the worst part. That was the fact that, unlike during your previous lesson, this time there was no explanation, no rhyme or reason. In fact, neither Miss Scarlet nor Miss More had spoken as much as a word since they'd begun, which only made things worse. You wanted desperately to know what the point of this was, but all you could to was gaze at them through tear-stained eyes as yet another orgasm rocked your weakening frame.

Your cock ached more than you ever thought possible, even after everything else it had been through this week. The head of it as purple now from the constant attention as Miss Scarlet's gloves, which still held it in their grasp. More tears fell as the last few drops dripped into the bowl beneath you, and you hung your head in exhaustion and despair. All of this- the constant, seemingly-never-ending torment as well as the silent treatment was unbearable. You want to cry out, to beg them to stop, or to at least tell you why they'd chosen to do this instead of countless other possible 'punishments', but you couldn't say a word.

They started up again, and as they did, you stopped struggling. There was no point anymore, if ever there had been. Drained as you were- emotionally, physically, and most certainly sexually, it seemed to be the only viable option. At this point, you were little more than a useless piece of meat. A mindless body to be used again and again by these women.

Which, the more your thought about it, had been true from the start.

Everything they had put you through- from the first lesson with Miss Scarlet after class, had been to bring you here. To a state of complete and utter defeat, as well as one in which the only option, the only possibility left, was to become whatever they wanted.

You hung your head in defeat, and as you did, Miss Scarlet's hand milked out one last orgasm.

"Are you ready?" She asked, forcing you to look up at her with tear-stained eyes.

Miss More undid the ball gag, and once it was out of your mouth, you took a breath and answered. "Yes, Miss Scarlet."

"I thought so," she continued with a smile. "This lesson was just what you needed."

Taking hold of your face with her cum-drenched gloved hand, she held your gaze firmly in her own. "Positive reinforcement can only go so far, especially with naughty students like you... And sometimes, we need to push it as far as we can go. To where pleasure and pain become one and the same.... And when that happens...

Her other hand moved back to your cock, and you felt yourself tense up before she even brushed against it. A wicked smirk covered her face at your reaction, and she immediately pulled the glove away. "When that happens, it's clear that the student in in your complete control."

Letting go of your face, Miss Scarlet and Miss More moved to the front of the chair. And as they stood there, towering over your seated and defeated form, you knew what they were looking for. Any trace of the arrogant, disrespectful student you'd once been.