A Private Lesson You Wont Forget 05

Another piece inspired by the amazing content of the lovely Scarlet/ 'fortheloveofgloves'.

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As the first rays of morning sun peeked their way through the window of the guest room, you found yourself once again awake, although far from rested.

Which was not to say you hadn't slept- you most certainly had, and not once could you recall waking up in the middle of the night. However, even with all of that, you still felt exhausted, as if the previous day's events hadn't simply drained your cock and balls, they had drained your very energy. So weak were you, that you struggled to get out of bed, forcing yourself to rise so as not to be late.

After your bath- which had only slightly soothed your aching bottom and sore cock, you'd sat alone in your room with your thoughts on the day's lesson. As well as the one you'd heard being delivered in the next room.

The fact that Miss Scarlet had seemingly seen fit to do the very same to Miss Moore as the latter had done to you continued to whirl around in your mind and lingered there even after you were called for dinner.

As with those that had come before it, the meal was exquisite. Whoever Miss Vera's 'staff' were, they did a magnificent job again and again, yet this time around, it was quite apparent that the mood in the dining room was much different. Not simply due to the spanking you'd endured making it fairly difficult to sit and eat comfortably, but by the fact that the one Miss Moore had clearly received from Miss Scarlet had changed the other woman's tune ever-so-slightly.

There were no wicked smirks or glances sent your way from her this time around. Miss Scarlet had made sure of that.

So the three of you dined in uncomfortable silence, then you dutifully pulled out their chairs for them and held the door open, watching them walk up the marble staircase before daring to do the same. There was no further discussion of your next lesson, and you could thus only imagine what it could be.

More than once as you drifted off to sleep, you found your mind wandering and wondering just what the women had in mind for the following day. As it was, the only clue you'd been given was that it was related to self-control and stimulation, which could really and truly mean a great many things. Both good and bad.

Just as you had the previous morning, once you'd awoken, you cleaned up quickly in the en-suite bathroom before making your way to the bottom of the stairs, standing there waiting at precisely eight o'clock. Eyes forward, collar tight, and cock practically begging to see just what the two twisted ladies upstairs would be wearing today.

Though it still ached from the seemingly endless handjobs and orgasms you'd received from Miss Scarlet, your erection still seemed ready and willing to accept more, and though a part of you most certainly agreed, another questioned if it would even be possible for you to make it through another such lesson from the two women. Let alone several.

When they eventually made their way down the stairs- keeping you waiting and on edge in more ways than one, you were slightly disappointed to see that, once again, their gorgeous forms were hidden beneath their silken robes, with only slight glimpses of their chosen gloves to tantalize and tease you.

And yet, those were more than enough.

Miss Scarlet had chosen a pair of short, wrist-length black leather gloves, and though they paled in comparison to some of the other ones you'd witnessed her wearing, they still send made your mouth water and your cock stiffen. It wasn't the length that mattered- not really, but the power which was infused in them by Miss Scarlet's very presence. Simply being allowed to lay eyes on them was more than enough to reinforce her control over you, and you relished in it.

Miss Moore, on the other hand, wore the same white pair she'd had on the previous day and, like at dinner, seemed slightly less animated than she had at the start of things. The lesson Miss Scarlet had given her must have truly been something seeing as it had managed to render the other woman so silent.

You wondered if that would change what they had in store for you or not.

"Good morning," Miss Scarlet greeted you with a smile. "I do hope you are prepared for today's lesson. It's sure to be a thorough one..."

Unsure as you still were about what they had planned, you simply nodded, ready as you could possibly be for whatever awaited you. Then, you followed the ladies to the dining room, holding the door open for them once more before making sure they were both comfortably seated before taking a seat yourself.

It continued to amaze you just how easily you'd slipped into such a subservient role. Where once upon a time such actions would have been as foreign to you as keeping your trap shut, now they came as naturally as breathing. It seemed that, after learning how to do the latter as quickly as you had, the former simply came hand-in-hand with such overt submission.

Breakfast was a simple affair, and though you ate, your mind continued to reel with questions you dared not ask. What did they plan on doing to you today, and just how badly would you have to suffer for Miss Moore to 'learn' whatever lesson Miss Scarlet had thought up?

You didn't need to wait long to find out.

Before the meal was finished, Miss Scarlet looked over at you and giggled, easily reading your unease as well as your curiosity. "Would you like to know what today's lesson will entail?"

"Yes, Miss Scarlet," you answered almost instantly, those three words practically burned into your tongue even as every part of your body remained on edge as you waited to discover just what was coming your way.

"It's quite simple," she began, sipping a cup of coffee as she did, her eyes never once leaving yours. "We are going to see just how well you can remain focused on a task whilst being stimulated in several ways... Specifically, while being repeatedly teased and pegged."

The moment you heard that, your jaw nearly dropped.

Of all the things you had been forced to endure since Miss Scarlet had decided to 'teach' you, you had never once expected something like this. Being spanked and cropped was one thing, but pegged? You'd heard of it, of course- had seen it done in several pornographic videos online, but never before had you ever expected to experience it yourself.

"I think he's a little nervous," Miss Moore added, her tone far more playful than it had been the previous day, further proof of just how well Miss Scarlet's lesson had seemingly sunk in.

"Oh, that's quite understandable," Miss Scarlet continued. "But it is a very important lesson to learn. After all, if he can't remain focused at all times, what use is he to us?"

Her words stung, as did the wicked laughter which followed from both ladies, and you practically sunk into your seat. What was worse was the fact that you couldn't find any fault in what had been said. So much of your worth now seemed to revolve around serving these women, and if you couldn't do that, what good were you?

With a sigh, you tried to wrap your head around all of this. Around the fact that- once breakfast was over and done with, you were going to get pegged. There was nothing you could do about it, save hope that they would go slightly gentler on you than they had with the spanking.

Soon after that, the three of you finished up your meals and, once you'd pulled out their seat for them, Miss Scarlet pointed a gloved finger at the dining room door. "Head down to the dungeon and meet us by the door in the back corner. Do not open it until we arrive. Is that clear?"

You nodded. "Yes, Miss Scarlet."

As you held the door open for them, you watched as they made their way back up the stairs to prepare, and once they were out of sight, you slowly walked towards the dreaded basement door. Flicking on the light, you headed down the steps, your eyes trying in vain to ignore everything around you.

The last thing you needed was for your mind to wander, to think about what else the ladies could do with the various toys and tools down here.

Eventually, your gaze fell upon the aforementioned door, and though a part of you was extremely curious as to what awaited you on the other side and how it related to what they intended to do to you, you dared not disobey Miss Scarlet's orders. She'd told you to wait for them, and you would do so without question.

That said, as you stood there, your mind did start to wander. You pondered just how they intended to peg you- in the videos you'd seen, sometimes the person on the receiving end was bent over, similar to how you had been during your spanking. Other times they were on their backs, legs up in the air as the pegger fucked them for all they were worth.

Neither way appealed to you but, again, you had very little say in the matter. Miss Scarlet had decided that this was to be your next lesson, and all you could do was hope when all was said and done, your arse wouldn't be in nearly as much agony as it had been the day before.

You weren't all that optimistic.

After several minutes, the basement door opened up, and the sound of heels clicking against the steps rang out once again. You immediately stood at attention, waiting for them to arrive and, just as with each time before, you found yourself unable to do anything but stare longingly as they stepped into view.

Miss Scarlet had seemingly chosen to live up to her name, seeing as nearly all of her chosen outfit consisted of red leather. Short, wrist-length red leather gloves, a zipped-up red leather jacket, and black and red snakeskin-esque leather thigh-high boots. Only a short black leather skirt stood in opposition to the rest, but it didn't matter. Your cock began to twitch instantly, clearly excited by the sight of its true owner.

Miss Moore, on the other hand, had gone all black. Knee-high black leather boots, elbow-length black leather gloves, and a tight black leather corset wrapped around her ample bosom, she certainly exuded the look of dominance she'd shown off previously, even if you knew now that behind closed doors she was clearly as submissive towards the other woman as you were.

Before they reached you, however, they stopped by one of the walls whose contents you'd tried your best to ignore while you'd made your way through the dungeon, and in the pit of your stomach, you knew why. Each woman pulled down a harness, then slipped it over their waist and clicked it shut in preparation for what came next.

The strap-ons.

Much to your dismay, they didn't simply pick one each. Instead, Miss Scarlet and Miss Moore seemed to take down several seemingly at random, all of varying size, length and color. It appeared that this was not going to be a simple affair- they had every intention of seeing just what you could take.

You only hoped you wouldn't disappoint them.

Satisfied with their choices, the ladies finished their approach, Miss Moore affixing a fairly normal-sized pink, rubber phallus to the front of her harness before stopping in front of you. Miss Scarlet smirked at your obviously nervous expression, then motioned for the door.

Only now that you'd been explicitly given the command did you dare open it and, as you did, you found you were quite glad that Miss Scarlet had told you to wait. If you'd looked inside prior, odds were you wouldn't have managed to remain standing very long.

Inside the room was what could only be described as a medical bed of some sort, with stirrups at one end and a raised chair at the other. Even without asking, you were fairly certain you knew precisely what you were expected to do, but even so, you waited for instructions.

"Lay down," Miss Scarlet said, a red leather-clad finger pointing at the bed. Without a word, you took a seat, then laid down, the cool padding feeling rather nice against your bare skin. However, before you could truly enjoy it, the women each took hold of one of your legs, slipped them into the waiting stirrups and restrained them there in preparation.

Once your legs were secured, Miss Scarlet pulled some straps from the sides of the bed and wrapped them tightly around your upper body and arms, making sure you were well-restrained before joining Miss Moore at the bottom of the bench to admire her handiwork.

"Very good," she said, her eyes moving from yours, all the way down your body, and stopping on your already rather hard cock and raised, bare bottom. "Very good indeed."

Giving your erection a tug, she giggled as you moaned, the brief touch of her leather-gloved hand enough to force a few drops of precum out of the tip, then returned to the head of the bed and took a seat on the chair. Her boots hovered mere inches above your face, and your eyes stared up at their soles as Miss Scarlet began to speak.

"Now then, as I said, you will be expected to focus on a task whilst being stimulated. And that task is the kissing, licking, and worshipping of our boots. You will begin with mine, and Miss Moore will start administering the stimulation."

You gulped even as your eyes couldn't help but gaze longingly at the bottom of Miss Scarlet's incredible boots. However, she wasn't finished.

"Not only will you be expected to complete this task to our satisfaction, you must also prove to us that you can control your... urges."

She didn't need to elaborate further for you to understand the meaning of her words, especially after the previous day's lesson, but that only made you even more uneasy. Not only were they going to peg and tease you as well force you to worship their boots, they were going to do so with the explicit command that you not cum whilst they did so.

If you'd thought it had been difficult to remain focused on your task whilst Miss Moore had dutifully spanked your bottom and Miss Scarlet had stroked your cock, the idea of trying to do so alongside all of this seemed downright impossible.

"Of course, you won't be the only one whose self-control will be tested," Miss Scarlet added, her eyes locked on Miss Moore, whose aura of dominance shifted but for a moment. If nothing else, you felt that meant the odds would be slightly in your favor this time around.

"Miss Moore, you may begin whenever you'd like."

The moment Miss Scarlet said this, she lowered her boots onto your face, and though you could no longer see anything beyond their soles, you could clearly hear the sound of something squirting- likely lube for the strap-on. Something which was quickly proven to be true when you felt the cool, slick rubber tip of Miss Moore's cock slip inside your waiting anus.

This unexpected sensation caused you to flinch ever-so-slightly, although, between the restraints and the boots on your face, you couldn't really move about all that much.

"Remember," Miss Scarlet added, her accent somehow seeming far stronger now that she was quite literally towering above you. "You are to worship our boots as well. Do not keep me waiting."

With a sigh, you stuck out your tongue and began to run it slowly along the length of Miss Scarlet's sole, moving from the sharp heel down towards the toe and back again, stopping on occasion to plant small, gentle kisses upon the bottom of her boot. And as you did, Miss Moore began to push the strap-on deeper into your anus a little bit at a time, trying to get a feel for it even as your bottom tried to figure out what to do about it.

After a few tries, it eventually gave in, and the cool, rubber shaft pushed past your cheeks and filled your arse, forcing a groan from your lips. One of her gloved hands took hold of your leg to steady herself, while the other-

The other one wrapped around your erection and began to stroke it.

It felt amazing.

While your cock still ached, the moment Miss Moore's leather-clad hand took hold of it, all of that seemed to fade away. Even the sensation of her own slipping in and out of you slowly seemed to fade away into the background as her hand stroked your throbbing manhood.

Your tongue continued its mission of lapping at the soles of Miss Scarlet's boots, moving from one to the other and back again, but even that was proving rather difficult to focus on as your cock surrendered to the other woman's touch.

Focus. That was what you were supposed to do.

And you were already failing at it.

Though it was difficult, you pushed aside the thoughts of the pleasure Miss Moore was giving you out of your mind, instead putting your mind solely on the tasks at hand. And the moment you did that, the thrust from her cock began to increase, moving in time with her stroking of your cock.

You groaned. They were certainly not going to make this easy on you.