Chapter 30

“Ah, a-aaah…”

As if the sheer magnitude of the pain had erased his ability to form words, Lino could only leak a continuous stream of agonizing groans. He desperately wanted to scream, but the terrifying realization that tensing his abdominal muscles would inevitably clench the hole currently impaled by the massive glans made him feel as though doing so would literally kill him.

“Once this part is inside, the rest will follow. Try not to be in too much pain, Sir Cliff.”

“Hngh, hk. Hnn… ah, ugh.”

Lowering his hips, Grondil relentlessly jammed the remaining portion of the massive head inside. Riiiiip. Lino hallucinated the horrific sound of his own flesh tearing. Blinking rapidly to clear the pooling tears from his eyes, he was met with the horrifying visual of the dark, monstrous chunk of meat completely vanishing inside him, dragging the surrounding skin of his buttocks inward with it.

“Hnnng… It hurts, it hurts so much…”

“Stop crying like a child.” Grondil chuckled, casually tossing out a remark that would be deeply alarming if directed at an actual child. “It’s a punishment. If you were enjoying it, it wouldn’t be much of a punishment, would it?”

“But still… Urgh! Ah, please, stop. P-Pull it out. Please? Ah!”

Reminding him that a punishment was meant to be endured, Grondil simply drove his hips down further. His cock was so absurdly long he had to physically guide it into the hole with his hand.

“Kk-hk.“

Unable to even draw a breath, Lino’s face drained of all color as he watched the gargantuan weapon invade his body. Desperately hoping this was all just a horrific nightmare—and praying that once the entire length was inside, he would finally wake up—he stared unblinkingly at the violation.

Lino’s already pale face somehow grew even more translucent, resembling a corpse. A broken, choking sound leaked from his parted lips, as if he were actively being strangled. Witnessing the severe physical reaction, Grondil finally let out a sigh and halted his seemingly endless, brutal invasion.

“Hk, haah… Hnngg…”

Only when the terrifying intrusion stopped did Lino frantically drag in ragged, desperate breaths. To avoid completely crushing Lino’s ass, Grondil slightly bent his standing knees. Lino’s entirely folded spine, screaming in agony, finally descended back toward the mattress. As his legs—rigid with pain and previously hovering in the air—finally touched the sheets, a long, shaky sigh involuntarily slipped from his lips.

“I suppose I’ll only put this much in for today. To think you swallowed this much on your very first time… I’m looking forward to our future.”

I’m starting to like this more and more, Grondil murmured, almost to himself.

In his entire life, Lino had never realized the phrase “I like it” could induce such profound, skin-crawling terror. And looking forward to the future? Did that mean the bastard fully intended to eventually shove that entire, snake-like monstrosity completely inside him?

While Lino was paralyzed by horror, Grondil lightly patted his ass, almost praising him for swallowing his cock so well. Then, agonizingly slowly, he began to pull his hips back.

“Ugh, ah… D-Don’t move. Hnng…”

A grotesque, visceral pain—as if his entire lower half were being forcibly ripped out—tore a sob from Lino as he begged the Duke to stop. The terrifying sensation that his internal organs were being dragged out alongside Grondil’s retreating cock filled him with absolute dread.

Hearing Lino’s desperate plea, Grondil simply let out a dry laugh. “Haha. Don’t be ridiculous.”

Grondil extracted his cock entirely, leaving only the massive glans lodged inside. In that brief moment of penetration, the shaft had seemingly absorbed the searing heat and moisture from Lino’s interior; the portion that had been inside was now noticeably darker and gleaming wetly.

“Since it’s your first time, I’ll be gentle.”

“G-Gentle…”

Lino stared at Grondil with a look of absolute, soul-crushing despair. Did the man genuinely believe the current atrocity fell under the category of ‘gentle’? If this was gentle, what horrifying acts constituted his definition of rough?

This is a punishment. He was going to endure this excruciating ‘punishment’ disguised as sex over and over again, until the Duke finally grew bored of him. Knowing with absolute certainty that his body would completely break long before the man’s interest waned, Lino squeezed his eyes shut tight.

Grondil’s cock drove inward once again. The horrifying sensation of his insides being forcibly pried open ignited at his tailbone, violently shooting up his spine to explode in his brain.

“Hngh!“

It hurt. There was nothing but pure, unadulterated pain. So this is why he called it a punishment. Squeezing his eyes shut, Lino couldn’t even wipe away the tears streaming endlessly down his face; his hands were entirely occupied with desperately shredding the bedsheets.

My throat is dry. Grondil flicked his tongue out, moistening his parched lips.

He meticulously maintained his promised depth, plunging in and pulling out with terrifying precision as he mapped Lino’s interior. As expected for a first-timer, it was impossibly tight. The constriction was so severe it bordered on painful, a far cry from the thoroughly broken-in, highly skilled partners he typically preferred.

Yet, rather than annoyance, a dark, ravenous thirst clawed at Grondil’s throat. He didn’t particularly indulge in carnal pleasures often, but he certainly wasn’t one to kick away a magnificent feast laid out perfectly before him. Aside from the utter lack of experience, everything about the man fit his tastes so flawlessly… no, he knew with absolute certainty he would never find another creature he desired more than the one currently pinned beneath him.

He had called it a punishment, but that was merely a convenient excuse; he knew perfectly well Lino would never have willingly consented if he had simply asked for sex. Therefore, Grondil fully intended to deliver a climax of absolute, mind-shattering euphoria.

Usually, just burying it this deep is enough to have them screaming in ecstasy.

He was acutely aware of exactly how long and thick his own cock was. He also knew precisely what happened to a partner when he selfishly shoved the entire length inside, which was why he meticulously maintained his current depth to prevent a literal bloodbath. Normally, penetrating this far was more than enough to automatically strike the prostate. His partners should be whining in pain while simultaneously sporting rock-hard erections from the overwhelming pleasure.

However, for some inexplicable reason, Lino was experiencing absolutely nothing but agony. He couldn’t possibly be impotent—he had just climaxed from a handjob mere minutes before penetration. Yet, every visible sign pointed to pure suffering: the hands violently strangling the bedsheets, the lips bitten so hard they threatened to bleed, the endless stream of tears leaking from tightly squeezed eyes, and the pale, limp flesh completely devoid of tension.

There wasn’t a single trace of pleasure to be found. Lino’s entire body was deathly pale. The only flushed skin was on his thighs and buttocks, entirely localized to where Grondil’s massive hands had gripped and slapped him.

“Hmm… is it hidden deeper?”

It occurred to him that his knight might possess a surprisingly coy, deeply hidden sweet spot. Imagining Lino’s utter mortification if he heard such an assessment, Grondil drove his hips forward, burying himself just a fraction deeper.

“Kk… Hrk…! Ugh… hurgh…”

The sensation of even deeper, untouched territory being violently forced open triggered Lino’s gag reflex. He frantically released the shredded sheets to slap a hand over his mouth. Because he had skipped a heavy breakfast due to a lack of appetite, only a small amount of acidic bile rose in his throat.

He explicitly promised he wouldn’t put it in any deeper. Why the sudden plunge?!

Lino shuddered violently against the agonizing sensation of his impossibly tight interior being relentlessly stretched further.

“S-Stop putting it… Ugh, haah…!”

“My apologies. However, I need to push a bit deeper so you can actually start enjoying this.”

“No, I don’t need to enjoy it, so just stop…! Ah! Hngh…?”

Lino desperately wanted to scream, This is a punishment, so I don’t need to feel good! Stop invading me! However, the desperate plea died in his throat, violently severed by an utterly alien sensation that exploded like lightning from somewhere deep within his forcibly stretched walls.

Until a split second ago, the agony had been absolute. It felt as though his body was being cleaved vertically in two, as if a red-hot iron skewer were relentlessly churning his insides.

But what the hell is this? The sensation still shot up his spine and pierced his brain, exactly like the pain. Yet, this bizarre, unfamiliar feeling teetered dangerously on the razor’s edge between agony and something entirely different.

“Haha.”

A dark chuckle slipped from Grondil’s lips, his brow furrowing. The internal walls, which had already been clenching with enough force to wring him dry, suddenly clamped down so viciously it felt as though they were trying to snap his cock in half. The pressure bordered on painful. And yet, he laughed. After listening to nothing but screams of pure agony, the sudden, breathless, sweet whine that finally tore from Lino’s lips made the crushing constriction entirely welcome.

“It seems my knight’s little switch is incredibly shy. It was hidden quite deep.”

Having finally struck the elusive sweet spot a few times, Grondil reached down and casually flicked Lino’s half-erect cock with his finger. With every tap, the angle of the erection visibly jumped. Amused by the responsive display, he began to gently stroke it. Almost instantly, the cock surged to full attention, pointing rigidly toward Lino’s flat abdomen.

His mind was already threatening to shatter from the alien sensations detonating in his rear; adding direct stimulation to his front caused Lino’s vision to literally flash white. It felt like fireworks were exploding behind his eyes.

“Hngh, ah! What is… Ah! Y-Your Highness, wait, please! Nngh! Ahh!”

“What else could it be? It’s the sound of the little chestnut I’m going to start pampering, telling me how much it likes this.”

“C-Chestnut? Hk!”

Why the hell is he talking about chestnuts right now?

Unable to comprehend Grondil’s bizarre analogy, Lino frantically tried to recall if the human body possessed an organ resembling a chestnut. However, the tsunami of pleasure violently surging from his lower half instantly annihilated any capacity for rational thought.

The searing heat pooling in his groin felt as though it were literally boiling in his lower abdomen. Is this really sex? What he did with women was definitely sex, and this was technically sex too. So why was it so fundamentally, terrifyingly different? Because it was with a man? Because he was on the receiving end?

Or… because the partner was this man…?

The confusing chestnut analogy vanished from his mind, replaced entirely by a terrifying new realization brought on by pleasure so intense his thighs were visibly violently trembling.

Such overwhelming, mind-altering ecstasy. He finally, terrifyingly understood the rampant homosexual affairs that had plagued the Order of St. Margia.

“Ah, aaah!”

Before he even realized it, his body had adapted to the brutal, relentless thrusting of Grondil’s massive cock. The agony vanished from Lino’s moans, replaced entirely by a higher, thinner, infinitely sweeter pitch of pure ecstasy.

Look at that expression. Anyone seeing that face would be perfectly justified in ripping off their pants and diving right in.

Lino’s prostate wasn’t just hidden incredibly deep; it was also abnormally small. Grondil realized that if he hadn’t selfishly pushed past his promised depth, the knight would have undoubtedly wept in pure agony until he passed out.

He looked so incredibly sweet, like he was coated in honey. His entrance was as tight as a needle’s eye, yet it yielded and stretched magnificently. Grondil had assumed a few careless thrusts would have him instantly drooling and whining in pleasure. But to his surprise, the prostate—which most partners could easily reach with just a finger—was buried shockingly deep and was unusually small.

“Sir Cliff, it appears you… are in very deep trouble.”