Cherreads

Chapter 5 - Chapter 5: Reload to MILF Route

When I was here for the first time, I didn't have a moment to truly appreciate how the mansion looked.

Well, I did later.

It screamed old money—not the flashy, tasteless kind, but the deep, silent, suffocating kind.

It was the kind of place that spoke of aristocratic grace layered over a foundation of political dynasty so entrenched in Japan that even blue-blooded aristocrats from Britain had to beg to become sons-in-law of the Sawamura Family.

All of this in what the rest of the world might call a backward island nation.

It certainly makes a sick kind of sense, then. If the Sawamura Family had a Death Note—the thing that killed me in my previous timeline—or a direct connection to it

This world has shocked me once again by revealing it was never ordinary.

There are layers of hidden mystery I hadn't even glimpsed in my first life, or even my second.

Is this the reason someone could take my head off without me feeling a single spark of pain, without even a sensation of separation from my own neck?

Wonderful.

If I had that kind of power…

This time, I was met by Eriri's mother.

She was still gentle, still elegant, just as she was when we first met.

Not yet the woman she would become—that indifferent, chilling figure who seemed to have every thread of fate under her control.

Yeah.

In that other timeline, she seemed not to have aged.

Time never touched her.

She remained flawless, her beauty sharpened into something almost icy, classical, breathtaking.

Such a powerful woman…

The thought twists in my gut, lower. A dark, hungry pulse of desire.

I wanted to tear that flawless kimono from her body, silk ripping under my hands as I exposed the pale skin beneath.

I wanted to bend her over the polished mahogany tea table, hike the fabric up around her hips, and drive into her from behind—hard, relentless, claiming every inch of that untouchable grace.

I imagined gripping her twin-tails like reins, pulling her head back as I fucked her raw, her elegant composure shattering with every thrust.

Her soft gasps turning into desperate moans, her perfect posture crumbling as her body arched beneath me, slick and trembling.

I wanted to feel her tighten around me, hear that refined voice break as she begged—not the poised matriarch of a dynasty, but a woman reduced to pure need, dripping wet, completely mine.

Fuck.

The fantasy alone had my cock aching, a low throb of hunger pulsing through me.

The sheer taboo of it—the violation of everything she represented, the thrill of dragging a queen down into the dirt and making her crave it—set my blood on fire.

Sayuri, noticing the intensity of my gaze, immediately put her doubt on the table. "Is there something wrong with me, Itou-kun?"

"No, auntie… It's nothing like that," I answered, my voice dropping slightly as I instinctively slipped into the role I needed to play—the inexperienced person, the virgin boy utterly dazzled by a beauty he'd never encountered before. I lowered my head, letting a hint of flustered awe color my tone. "It's just… you're so beautiful…"

For a mature and lethally perceptive woman like Sayuri, this was fatal attraction. In this world where women held the power, they craved a man whose attention was captured wholly and solely by them. My unguarded, subconscious admission was a direct hit.

"Ara… such a sweet boy." A low, pleased chuckle escaped her lips, the sound rich with satisfaction. "If you don't mind, let me accompany you while you stroll around the house, Itou-kun." Her demeanor shifted seamlessly as she turned to Eriri, her gaze turning stern. "Eriri, you should head to school now. You're already late."

"You're so noisy, Mother. I'll go without you having to tell me!" Eriri stomped her foot on the floor, a flash of childish defiance in her eyes, before snorting and leaving with a deliberately rude flourish.

I understood the difference. With inexperienced, insecure girls like Eriri, a façade of confidence and controlled aggression worked—it projected strength they lacked. But with Sayuri? That strategy would be a catastrophic mistake. It would only make me look like a transparent playboy, a liar she'd see through in an instant. That was undoubtedly why she had monitored my every interaction with her daughter for two decades with such unrelenting suspicion.

"Don't mind her, Itou-kun," Sayuri said, her voice softening back into that gentle, comforting tone as she turned her full attention back to me. Her gaze was unnervingly direct, those perceptive eyes never leaving my face—more precisely, they were locked straight onto my own, reading every micro-expression. "Eriri just misses her father terribly. She often acts out when she's feeling lonely."

Even though her exterior was always stern with Eriri, I knew this woman possessed a chilling, maternal ferocity. She would not hesitate to kill anyone who dared to act inappropriately toward her daughter.

So, I played my part perfectly, offering a defense that painted me as understanding and kind. "It's fine, auntie. I know she doesn't mean it. Underneath it all, she's actually very nice."

Her smile widened at my words, a flash of genuine maternal pride shining through.

"Then, I sincerely hope the two of you can get along well in the future, Itou-kun…" she said, the promise—or perhaps the warning—hanging delicately in the air between us.

However, that was not the rhythm I wanted. If I let this continue, I would be gently guided back onto Eriri's preordained route—a path I had walked in previous timelines.

It would slam shut any chance I had with this woman, the one I truly craved, the one I longed to possess and breed, but could never reach in all my previous, futile attempts.

So, I shattered her plan.

I dropped the façade of the polite, understanding boy and instead embraced the raw, impulsive ignorance of a virgin who had zero emotional intelligence.

I stood up abruptly from the sofa, the movement jerky and charged with false desperation.

"Auntie," I blurted out, the words clumsy and too loud. "I like you. Please… go out with me."

Sayuri was visibly taken aback. For a moment, a thick, stunned silence hung between us, freezing the air in the room.

Then, she burst out laughing.

It wasn't a gentle chuckle, but a low, genuine, and eerily knowing laugh that seemed to echo from a place of deep, dark experience.

"Itou-kun… my love is not some cheap, easy thing. It is suffocating. My previous husband couldn't stand its weight. He withered away and died in depression because of it. Please… don't speak of this again if you don't understand what you're asking for—"

Before she could even finish her warning, I moved. I closed the distance, grabbed her wrist to stop any retreat, and kissed her.

It wasn't gentle or seeking permission; it was a forceful, claiming press of my lips against hers, a physical interruption of her speech and her control.

My cock was already painfully erect, straining against my pants.

I made no attempt to hide it, letting my entire body broadcast my desire.

I looked at her with my lust completely naked in my eyes, every raw intent easy for a woman like her—a woman who needed to see and catalog everything—to read.

For a control-obsessed woman like Sayuri, a man like this—unreadable not because he was calm, but because he was a storm of simple, hunger-driven impulses—was a perverse favorite.

A smirk touched her lips the moment we separated from the kiss, a spark of dark amusement replacing her shock.

This was what she preferred.

"Itou-kun…" she said, her voice a purr of regained composure. "Sit down. We can… talk about this again later. For now…"

 Her eyes dropped pointedly to the blatant bulge in my trousers. "Let me take care of your more immediate need."

I obeyed, lowering myself back onto the sofa as instructed.

She sank gracefully to her knees before me, her movements deliberate.

Her fingers hooked into the waistband of my trousers and underwear, pulling them down in one smooth motion to free my aching cock.

She took me in her hand, her grip firm and knowing.

Her thumb traced slow, teasing circles around the sensitive head, her eyes locked on mine. "Do you want me to continue, my eager little boy?"

"Yes, auntie… please…" I gasped out, layering my voice with intense, boyish lust, letting my gaze scream the hunger to shove my cock past her lips and fuck her mouth without restraint.

And true to the persona of someone with zero self-control, I didn't wait.

I surged up from the sofa again, my movements rough and impatient.

I guided the swollen head of my cock to her parted lips.

She opened her mouth for me almost subconsciously, a flash of dark pleasure in her eyes as I began to thrust into the wet heat of her mouth, setting a frantic, shallow rhythm.

"Auntie… this is so good… Ah… I'm gonna cum!" I moaned, the words guttural and unrestrained.

My hands instinctively fisted in her twin-tails, holding her head steady as my hips jerked forward one last time.

I erupted, releasing a massive, pulsing flood of cum directly down her throat.

She choked briefly, her body tensing, but she never pulled away.

She swallowed every last drop, her throat working around me until I was completely spent.

When I finally slipped out, she wore a satisfied, almost maternal smirk, a thin strand of saliva and seed connecting her lip to my softening shaft.

"Good boy," she murmured, her voice husky.

She drew my head against the incredible softness of her plump chest, cradling me as she gently stroked my hair. "Rest now, Itou-kun. Regarding school, I will inform them of your absence today."

Sensing the restless, predatory energy still simmering in my spent body, she carefully disentangled herself.

She guided my head back onto the sofa cushions with a firm gentleness, then stood up, smoothing down her clothes.

"Anyway," she said, her composure fully restored, her tone shifting back to one of practical hospitality. "I will let the servants know which room is yours. If you have any needs, just tell them."

This time, she didn't even mention her daughter.

Even her answer to my confession was deliberately ambiguous.

More tellingly, she didn't refuse our growing intimacy, which, in this unspoken language, signaled a clear acceptance.

The most damning proof was her possessiveness: by not invoking her daughter's role in caring for me, she silently claimed that territory for herself.

Despite this small victory, I didn't allow a triumphant smirk to touch my lips.

I merely offered a humble, grateful nod, the perfect picture of the earnest young man she believes I am.

All the while, my mind was already racing ahead, plotting the meticulous steps to uncover this woman's secrets, to lay bare the mysteries of this world she seems to gatekeep, and to dominate her completely—but only after I have achieved every one of my own, deeper objectives.

For now, though, let's play our assigned roles to perfection.

I shall be the devoted, virgin boy, and she can luxuriate in her part as the indulgent sugar mommy.

We'll see how long the script holds.

More Chapters