The Duke let out a quiet sigh. Then he ran a hand through his hair, and a moment later came the sound of something being undone.
Oh.
It was the sound of the Duke unbuckling his belt. He took hold of both ends lightly, folded it in half, pulled it taut, and slapped it lightly against his own palm a few times — testing the weight of the impact. The sound rang sharp and clear in Ivan’s ears, and his immediate future began to take shape before him. Tonight, sleeping flat on his back was almost certainly out of the question.
Anticipating that he wouldn’t be able to sit properly for quite some time, Ivan nearly let his mouth curl upward just from the thought of it. Catching himself, he barely managed to pull his mind back into line and bit down hard on his lip — then quickly ducked his head in case the Duke was watching. The faint metallic taste of blood seeped from the cut. And at the very same moment, the arm holding the belt swung wide.
Crack—!
“Ngh……!!”
The belt cut through the air with a vicious sound and came down on Ivan’s backside without warning. It wasn’t a full-force strike — the Duke had swung lightly. But light by the Duke’s standards was something else entirely, and the belt was leather to begin with, which made it twice as painful as a bare hand. Even a casual swing from someone like the Duke — how gentle was that really supposed to feel to Ivan? A single strike left a vivid red mark seared into Ivan’s skin.
The soft, supple flesh of his backside shook from the impact. The sudden blow startled Ivan so completely that any proper sound died in his throat. The stimulation silenced him before he could form words.
And that became an added fault. In the shock of the moment, Ivan had failed to do what he was naturally expected to do each time the belt came down. The Duke reacted with visible displeasure, and when he let out a sigh, Ivan realized his mistake too late and rushed to open his mouth.
“Haah.”
“Ah…… one, one……!”
Every time he received punishment by caning, he was required to count aloud. That had been the most basic rule established through all the training he’d received until now. But thrown off by the sudden strike and the stray thoughts that had been drifting through his head, Ivan had lost focus and missed it entirely. He trembled and drew his legs inward. The Duke would raise the severity of the punishment in proportion to Ivan’s mistake — that was a given. It was going to hurt, but knowing that it meant that much more pleasure on the other side, Ivan felt as though he might lose control right then and there.
“Again.”
“Yes…… yes.”
The word again left the Duke’s mouth. That meant starting the count from the beginning. Ivan swallowed a moan and clenched his backside tight. With the tension in his muscles, the round, soft flesh dimpled slightly. The Duke trailed the end of the belt lightly along it before lifting it again and bringing it down sharply against the desk right next to Ivan’s bracing hands. It was a warning — and a clear indication of the Duke’s irritation.
“Do it properly. Unless you want to end up in pieces like before.”
The Duke said nothing about how many strikes there would be, or how hard they would come. He seemed to intend to keep going until he was satisfied — or until Ivan couldn’t take any more. Ivan quietly predicted he wouldn’t be walking properly today, and kept his backside clenched. And then the punishment began again.
Smack, crack! Crack!
“One! Two……! Ngh! Thr-three…… hgh……!! Four!”
The belt sliced through the air with a sharp, merciless sound. It came down again and again on Ivan’s backside without reprieve, leaving red marks blooming across the skin. Heat radiated from the beaten flesh. The struck areas began to swell visibly within moments. The belt fell left and right in alternating strikes, evenly across both sides. Because of it, Ivan’s composure — his body, his expression — was on the verge of unraveling entirely.
“Hah……! Ah! Five, si-six, ugh……! Hgh! Se-sevennnn……!”
Ivan forced the numbers out through broken sobs. His pronunciation was slipping, blurred by tears. Before he’d even reached ten, Ivan’s posture had visibly collapsed. The arms that had been straight were now bent, his upper body was sinking lower by degrees, until eventually he was slumped forward against the desk. And yet his chest still wasn’t fully touching it — just barely — so the Duke, watching that, curved one corner of his mouth upward.
He usually manages to hold out a bit longer — why is he falling apart so quickly today. The Duke turned that thought over and swept his gaze over Ivan’s body to find the reason. He considered that it might be a matter of stamina — his cock had been wrung dry both the night before and again just moments ago — but the more likely culprit was still the toy buried inside him.
With every strike of the belt, it wasn’t only his backside that was being stimulated. Every time that soft flesh shook from the impact, the toy would have shifted and ground against Ivan’s inner walls — and that sensation would have made it all the harder to endure.
Pain and pleasure hitting simultaneously — of course someone as easily undone as Ivan couldn’t simply hold his ground. The Duke paused in his steady rhythm of strikes and let his gaze drop a little lower. With his posture collapsed, even the legs he’d been keeping clenched had fallen slightly apart, trembling uncontrollably. Between Ivan’s parted thighs — his cock, hanging limp and spent. Yet it was still leaking without decency, still announcing the shamelessness of Ivan’s indecent, wretched body without fail.
The Duke wordlessly lifted his gaze again. That few number of strikes, and his backside was already flushed deep red and swollen. Looking at those thoroughly punished cheeks, the Duke could almost feel the ache of it himself. But he paid it no mind. What held his attention instead was the handle of the toy protruding between those reddened cheeks, and the hole around it — struggling, or perhaps savoring — clenching and rippling as though it refused to let go.
Ivan was barely holding onto his senses, undone by the presence of the toy running through him. Just enduring the strikes was already at its limit — but with every blow of the belt, the toy was jostled and sent rocking deep inside him, sending stimulation rippling through his inner walls. Because of it, Ivan was losing his footing far more quickly than usual. All he could do was force his legs straight each time they tried to buckle and keep himself upright by sheer will.
He should have been pushing his upper body back up, but his arms had gone too weak to manage it. He tried to stay still against the pulsing, throbbing ache in his backside and hole, but his body refused to cooperate. If anything, now that the strikes had paused, the burning sensation grew even more acute — and Ivan let out a low, pained sound as he pressed his cheek against the desk, at least slightly cooler, trying to find some relief. But even that brief reprieve wasn’t given to him for long.
“Hah……! Ah!!”
The strikes came again. But this time they were different from before. The belt — which should have been coming down on his backside — didn’t land on his backside at all. Instead it struck hard and directly against the hole between his cheeks, right where the toy was buried. The impact drove the toy deeper than it had already gone, grinding into his inner walls, while the hole itself began to burn and swell — and the combination of pain and pleasure was beyond description. Ivan was so startled he couldn’t call out a number, and his upper body collapsed the rest of the way.
Even his chest, which had just barely been hovering above the surface, came down fully against the desk, scattering and disordering the documents. His knees bent, and the backside that had been lifted so high sank down with them. Watching that, the Duke smiled to himself — a cold, satisfied smile that Ivan couldn’t see.
“Again.”
Ivan had missed the count. Which meant it was starting from the beginning once more. Ten strikes, twenty strikes, forty — nothing had been decided. But what was clear was that the range of punishment now included not just his backside, but the hole filled with the toy replica as well. Ivan knew for certain that he wouldn’t be able to hold out if he took it there again. He might lose control entirely — come helplessly, make a mess, and black out on top of it. Genuinely flustered now, Ivan shook his head and tried calling out to the Duke to buy himself even a moment — but the Duke had already raised his arm before he could finish.
Just as he’d feared, the belt was no longer aimed at his backside. It was aimed at the hole. The sound of it slicing through the air rang viciously through the room, and with each stroke, the toy thrust deep and then pulled almost out in rapid succession, churning against the ridged inner walls — and as the hole itself swelled and burned, the pain and pleasure became something beyond any words.
“Ah! Wait, Master…… ah! Hah! Stop—…… ah……!”
The stimulation was overwhelming. Ivan couldn’t count — couldn’t manage anything at all — just bucked his hips wildly and thrashed, toppling and scattering the documents on the desk, some of them tumbling to the floor. His toes scrabbled and curled and stretched in a frenzy as though trying to flee. But the more he struggled, the more firmly the Duke said again — not reducing the force at all, in fact increasing it as he swung the belt. With full force behind it, the belt came down again, harder than before, directly on Ivan’s hole — and Ivan’s hips snapped violently upward, his head jerking back.
Whatever composure he’d been barely clinging to was gone. His eyes had gone slack and unfocused, his mouth had fallen open, drool running from his lips — making his current state unmistakable — and his eyes had rolled back, pupils losing their focus entirely, showing all too plainly just how deeply he was feeling it.
But unfortunately, at that angle, the Duke couldn’t see the expression that had completely fallen apart. Perhaps because of that, the Duke didn’t stop. The strikes passed ten, passed twenty — and the belt kept cutting through the air.
By this point Ivan was on the very edge of losing consciousness. What remained of the rational part of his mind that had been trying to maintain his expression had dissolved entirely — and with every blow that sent his hips rocking upward, he was putting on a display in front of the Duke of someone grinding their hips back like an animal in heat. The fluid that splattered across the floor with every deep arch of his back showed in stark terms just how many times he had come and how intensely he had been feeling it. Watching that sight, the Duke — who had been continuing to strike throughout — finally paused after the thirtieth blow.
“Hgh…… hh, ah……!”
But Ivan’s trembling didn’t stop. The thread of rationality had clearly snapped — desperate sounds poured from him and rang through the room, and between his legs and across the floor below, everything was slicked and stained with what he’d been leaking all through the punishment. Taking in that sight, the corners of the Duke’s mouth were still lifted.
Striking Ivan like this was satisfying something deep in the Duke’s appetite. What he really wanted was to beat him all over his body and spend the entire day taking him apart over and over again — watching Ivan sob and cry and lose his mind entirely beneath his hands. But in Ivan’s current state, one more strike and his body would clearly give out.
The Duke surveyed him with something like pleased deliberation, deciding where to place the final blow. Then he raised his arm once more and brought the belt down. It didn’t land on the backside. It didn’t land on the hole.
Crack—!!
“Hah!!”
