Harem Training System: Every Girl I Train Makes Me Stronger!

Chapter 36: 36. Training The Vice-Headmaster To Give Head! (Gone Terrible At First)**

The heavy, emotional tension in the room was suddenly punctured by a sudden, fierce determination in Catherine’s eyes. The jealousy was there, yes, but it was quickly being overtaken by her elven pride.

She was a scholar, a leader, and a woman of high standing; if she was going to do this, she was going to do it better than anyone else in the history of her race.

"Fine!" she declared, her voice cracking slightly with a mix of bravado and wine-induced stubbornness.

She looked up at him, her silver hair messy and her eyes blazing with a competitive fire. "If this is a ’discipline,’ then watch me, William!"

"I will not be a mediocre student! I will be the best... the absolute best at this!"

Before William could even offer a cautionary word, Catherine lunged.

Driven by a frantic need to prove her capability, she didn’t use the "refined" methods he had just taught her. She didn’t start with the lips or the gentle swirling of the tongue.

Instead, she threw her entire head forward in one singular, ambitious movement, attempting to take the entire massive head and a significant portion of the shaft into her mouth in one go.

"GULP! GAAAAAAH! HUK! HUK! HUK!"

The sound was violent and ungraceful. The sheer, uncompromising girth of his cock hit the back of her throat like a solid wooden pillar.

Her eyes bulged, watering instantly as her gag reflex went into overdrive.

"Mmph! Hnnngh! Gaaaah!"

She recoiled as if she’d been struck, pulling back so fast she nearly tumbled backward onto the floor. She collapsed against his thighs, coughing violently, her face turning a bright, frantic shade of pink as she tried to regain her breath.

"Cough! Hah... hah... hnnn... oh gods..." she wheezed, her eyes streaming with tears of pure, unadulterated shock. "It’s... it’s too... huff... it’s too much!"

"It’s like trying to swallow a dragon’s tooth!"

William stood there, his hands still resting on her shoulders, but his face had returned to that legendary, deadpan flatness. He didn’t laugh, though he wanted to; he didn’t even look surprised.

He just looked... tired. He stared down at her with the patient, slightly disappointed expression of a master instructor watching a student try to lift a heavy boulder with their teeth.

He let out a long, slow exhale, the silence stretching between them as he waited for her coughing to subside.

"Catherine," he said, his voice incredibly calm, almost clinical, despite the fact that he was standing there completely exposed. "That was... impressive."

"In terms of sheer, unbridled stupidity."

"Ah! Hnnn... how can you be so... so cruel?!" she protested, wiping her watering eyes with the back of her hand, her voice still shaky. "I was trying! I was trying to be the best!"

"You were trying to choke yourself to death is the correct answer, by the way," William corrected her bluntly.

He reached down, his fingers gently tilting her chin up so she had to look at him. "Listen to me..."

"You can’t rush a masterpiece, and you certainly can’t rush this."

"You’re dealing with a massive amount of volume here."

"You can’t just lunge at it like a starving beast."

He gestured toward himself, his expression unmoving. "You have to respect the scale."

"If you try to take it all at once, your body is going to fight you every single time."

"You have to ease in. You have to let your muscles relax, let your mouth adjust to the width, and let the sensation build slowly."

"You can’t skip the foundation of the lesson just because you want to reach the climax."

He leaned down slightly, his shadow falling over her flushed, embarrassed face. "This isn’t a sprint, Catherine."

"It’s a marathon. And if you keep rushing like that, you’re going to end the ’training’ before we’ve even finished the warm-up."

Catherine pouted, a small, wounded sound escaping her. "Mmm... hnnn... but it’s so big... it’s intimidating..."

"It’s supposed to be," William murmured, his voice softening just a fraction, a hint of a dark, knowing smirk finally returning to his lips. "Now, take a breath."

"Stop trying to conquer it, and start trying to feel it. Again. And this time... try not to die."

"Hmph!" she huffed, though she didn’t argue.

She took a deep, shuddering breath, her eyes refocusing on the massive, pulsing length before her, her hands reaching out once more, much more tentatively this time. "Aaaah... fine... slowly... hnnn... slowly..."

Catherine took a long, trembling breath, forcing the frantic energy of her previous failure to settle into a focused, singular purpose. She looked up at William one last time, seeing his calm, unmoving expression, and it gave her a strange sort of strength.

She wasn’t going to let a piece of flesh defeat her pride again.

"Mmm... hnnn... watch me, William," she whispered, a defiant glint returning to her eyes. "Slowly... yes..."

She leaned in, but this time, her movements were deliberate and controlled. She didn’t lunge; she drifted.

She began by pressing her lips softly against the broad, weeping tip of his cock, savoring the heat and the saltiness of his pre-cum. She used her tongue exactly as he had instructed, swirling it around the sensitive ridge, teasing the opening of her mouth with the sheer girth of him.

"Nnn... mmm... hmmm..." she hummed, the vibrations of her throat traveling up the shaft and sending delicious, low-frequency tremors through William’s entire body.

William remained stoic, his hands resting loosely on the table behind him. He felt the warmth of her mouth, the incredible softness of her elven lips, and the rhythmic, expert swirling of her tongue.

He didn’t gasp or cry out; he had been a man of experience long before this reincarnation, and he knew how to maintain his composure. He simply closed his eyes, a small, satisfied grunt escaping his nose as he felt her begin the real ascent.

Catherine began to slide him in, inch by agonizing, delicious inch. She focused on relaxing her jaw, consciously widening her mouth to accommodate the massive circumference.

As the head passed her teeth, she felt the pressure mounting, a heavy, stretching sensation that made her eyes water with pleasure.

"Ahhh... mmmph... hnnn..."

She pushed deeper, her lips stretching taut around the thick shaft. The sensation was overwhelming; the sheer mass of him felt like it was filling her entire being, stretching her throat to its absolute limit.

She could feel the pulse of his blood against her tongue, a rhythmic thudding that matched the beating of her own heart.

As she neared the halfway point, the urge to gag returned, a primal reflex screaming at her to pull away. Her throat constricted, and a small, muffled sound of distress escaped her.

"Mmmph! Gaaaah!"

But she didn’t stop. She thought of his words: the discipline, the training, the mastery.

She forced herself to breathe through her nose, to relax the muscles of her neck, and to embrace the fullness. With a final, determined surge of will, she pushed herself forward, taking the entire length into her mouth, driving the head of his cock all the way back until it pressed against the very back of her throat.

"HNNNNG GAAAAAHHHH!"

The sound was a muffled, choked scream of pure, unadulterated sensation. Her eyes rolled back in her head, and her entire body shuddered.

The feeling was immense, a massive, hard presence that seemed to occupy her entire soul. She was gagging, yes, her throat working hard to accommodate the intrusion, but it wasn’t the painful, frantic gagging from before.

It was a deep, heavy, soul-shaking sensation of being completely, utterly filled.

"Mmmph... hnnn... nngghhh... mmmppphhh!"

She held him there, her cheeks hollowed out by the sheer volume of him, her hands gripping his muscular thighs so hard her knuckles turned white. She was trembling, a fine, continuous vibration that ran from her head down to her toes.

The sensation of his massive cock deep in her throat, the heat, the pressure, the overwhelming musk of him—it was more than any elven woman had ever dared to dream of.

William finally let out a low, heavy groan, his fingers digging into the wood of the table. He didn’t lose his cool, but the sheer tenacity of her, the way she was braving the discomfort to achieve total immersion, was starting to push him to his limits.

"Good... nnngh... very good, Catherine," he rasped, his voice a dark, gravelly shadow of itself. "You’re... you’re actually doing it."

"You’re mastering the depth."

Catherine couldn’t respond with words, only with the frantic, needy sounds of her throat as she began to move, her head bobbing in a slow, rhythmic, and incredibly intense motion, her eyes fixed on him with a look of triumphant, lustful madness.

She was no longer just a student; she was a woman possessed by the sheer, massive reality of him.