Night fell quietly as the two returned to the Shinomiya residence...
While Diego was taking his bath, Shinomiya Kaguya—face flushed with shyness—approached Hayasaka Ai in a pose full of deliberate show-off energy.
She hugged the heart plushie, cleared her throat twice, and began her provocation: "Ya~ Whose cute plushie is this?"
"?" Hayasaka Ai stared at her with narrowed eyes ꐦ≖ ≖.
What is milady up to now?
"Oh~ So this is the cute plushie Brando-kun won for me on our very first date~"
"...Dio kissed me."
Hayasaka Ai understood exactly what Shinomiya Kaguya was trying to do. Her irritation meter rose—currently at 65%.
Shinomiya Kaguya's competitive spirit ignited. Forgetting past lessons, she decided to go head-to-head with Hayasaka Ai.
Next, Shinomiya Kaguya inexplicably started parading back and forth in front of Hayasaka Ai, shaking her head constantly to flaunt her low bun hairstyle.
"Ya~ Who tied this super cute hairstyle for me? Oh, it was Brando-kun~ Hayasaka, did Brando-kun tie your hair on your first date too? I'm really curious~?"
"...Dio kissed me."
Damn it, Hayasaka—is that the only line you know?!
Shinomiya Kaguya's eyes slowly widened. Her competitive drive surged again.
Hayasaka Ai's irritation meter rose further—currently at 81%.
"Hayasaka, can you say anything else?!" Shinomiya Kaguya refused to back down. "It's just a kiss—what's so great about that? I can do it too!"
"...Dio didn't kiss you."
Hayasaka Ai's irritation meter reached 99%.
"Are you underestimating me, Hayasaka?" Shinomiya Kaguya hugged her flat chest, turned her head away with a huff, and—despite having no confidence—stayed stubbornly defiant. "Tonight I can make Brando-kun kiss me too."
"Heh, is that so?!"
Just a mere milady—daring to look down on me like this!
Hayasaka Ai sneered inwardly: Milady, you're out of luck. You'd better still be able to smile tonight!
This was the honest truth!
This woman had gone full red-hot rage mode. Irritation level: 200%.
Tap tap tap...
"Huff— Feels so good after a bath—" Diego emerged from the bathroom wrapped in a bath towel, steam rising from his toned physique. He glanced around curiously and asked, "By the way, where's my, Dio's, room?"
"Ahaha... for some unknown reason, there are no guest rooms available." Shinomiya Kaguya gave an awkward laugh in explanation.
This was a lie!
This woman was already scheming hard!
If there were no guest rooms, given Brando-kun's personality, he might suggest sleeping together. After all, her bed is plenty big...
Then, with a man and woman alone in a room, it would be perfectly normal for something to happen—like a kiss, for example...
"..." Diego scanned the area. His expression froze. He hissed. "Wait wait wait—you're saying in this huge house, there are no guest rooms?"
"I, Dio, have nowhere to stay again... This is really troubling..."
To be fair, Shinomiya Kaguya did understand Diego's personality quite well—he really was already calculating how to crash in someone else's room.
But she still hadn't known him long enough to escape Hayasaka Ai's scheme.
Diego pondered for a moment. His gaze skipped over Shinomiya Kaguya and landed straight on Hayasaka Ai, who wore a "dangerous" smile. A certain sentence echoed in his mind.
[If you have nowhere to sleep tonight, remember to come find me.]
That's right! Hayasaka Ai had planted the seed early in Diego's mind to come sleep in her room—that was her absolute confidence.
And most importantly—her Christmas present.
"Maid-san————, come sleep with this Dio————!!!" Hayasaka Ai finally got to hear the words she wanted.
Hoist...
Letting Diego sling her over his right shoulder, on the way back to his room, she cast a glance toward Shinomiya Kaguya and grinned wickedly.
"Heh!"
Bam!
The door to Hayasaka Ai's room slammed shut.
Click...
The lock engaged—from Hayasaka Ai.
This is payback, right? This is payback, right? How is this anything but payback?!!
Shinomiya Kaguya's eyes slowly widened.
Right now Hayasaka and Brando-kun were alone together in a locked room...
Shinomiya Kaguya broke into a cold sweat. She stumbled anxiously yet carefully to Hayasaka Ai's door, pressed her ear against it, and tried to listen for any sounds inside.
Damn it! Why buy such good soundproofing?! I can't hear anything at all?!
Tomorrow I'm firing whoever suggested this door!
They didn't do the sacred thing, right...
I've read in books—normal unrelated men and women alone in a room will inevitably end up doing that in the end.
No... no way.
Hayasaka is a very cautious girl. She wouldn't easily do that with someone she doesn't like...
Oh no—she super likes Brando-kun!!!
No no no—sure, she's the type to do anything to achieve her goals, but when she's not angry, her actions still have some conscience. Compared to the private staff dorm provided by the Shinomiya family, she probably prefers a more romantic setting, right?
It's fine, it's fine. Even though she's terrifying when angry, when she's not angry everything's okay—when she's not angry—
[Heh!]
She seems super angry?!
Remembering the dangerous smile Hayasaka Ai gave before entering the room, Shinomiya Kaguya clutched her head in despair.
Nooo—the President's first time is about to be taken by Hayasaka?!
Shinomiya Kaguya's once-firm conviction wavered in that moment. Shocked speechless, mouth agape, she nearly started knocking.
I just wanted to brag a little about how happy my first date was—in front of Hayasaka, just like she once bragged to me! Am I really that bad?!
Shinomiya Kaguya couldn't sleep at all.
Meanwhile, inside Hayasaka Ai's room...
Hayasaka Ai hooked her arms around Diego's neck, smirking wickedly as she asked: "Dio, has anyone ever forced a kiss on you?"
"Hm? You mean..." Diego looked up, but his next words were cut off by Hayasaka Ai's following action.
She tugged his collar downward with slight force, closed her eyes, and leaned in hard.
Chuu!
She did it!!!
Diego was forcefully kissed by the sulking Hayasaka Ai!!!
"Huff... huff... No one has before. The first person to force a kiss on you isn't anyone else—it's me, Hayasaka Ai!" After their lips parted, Hayasaka Ai panted with flushed cheeks, pointing her thumb at herself.
Once again, the tables had completely turned. And Diego—who from beginning to end had firmly believed offense was the best defense—how did he react to being the one forcefully kissed?
First Frieren, now Maid-san—this great one... is thoroughly pissed!!!
Have I been too relaxed, letting people keep offending my, Dio's, supreme dignity?!
Snap! Snap!
Veins bulging on his forehead, Diego slowly widened his eyes. From a spatial rift he pulled out Hayasaka Ai's Christmas present—that purple ribbon—and gave it a couple of casual tugs, producing sharp whipping sounds.
He piled on an evil grin, very satisfied with its quality.
"You actually dared to provoke me, Dio... You've got guts..."
"I, Dio, am a carnivore..."
Diego's eyes burned with feral hunger, as he stared down at Hayasaka Ai. The purple ribbon her Christmas gift dangled loosely from his fingers. He gave it a tug, the sharp snap of silk cutting through the heavy silence like a promise. Hayasaka's breath caught, her earlier boldness flickering beneath the heat rising in her cheeks. She'd stolen that kiss to push him, to claim a piece of control, but curve of his grin told her she'd just unleashed something far more dangerous.
"You really think you can provoke me, Maid-san?"
Hayasaka's pulse hammered in her throat. She knew Dio his arrogance, his dominances new, intoxicating. "Dio, I—" she started, voice already trembling with want, but he silenced her by seizing her chin , forcing her gaze up to his blazing blue eyes.
"Shut up," he ordered, thumb dragging across her bottom lip, prying it open. Then his mouth crashed down on hers. His tongue shoved past her lips without asking, claiming every corner of her mouth, tasting the faint sweetness she still carried from earlier. Hayasaka moaned into him, hands flying to clutch his shoulders, nails biting into hot skin as she tried to match his ferocity.
He growled against her lips, one hand fisting in her pale yellow hair and yanking her head back sharply to expose the delicate line of her throat. He broke the kiss only to attack her neck teeth scraping, sucking hard enough to bloom dark marks across her skin.
"You started this,"
"Now you finish it my way."
Hayasaka whimpered, thighs already pressing together at the rough promise in his voice.
"Dio… you're being so mean," she teased breathlessly, but the words dissolved into a sharp gasp when his hand slid down her side, fingers digging into her waist with bruising strength as he dragged her flush against him. His thick, heavy cock pressed insistently against her inner thigh through the thin barrier of her skirt.
"Mean?" He laughed. "You haven't seen mean yet." In one motion he flipped her onto her back, pinning both wrists above her head with a single large hand. The purple ribbon came into play immediately—he looped it around her wrists with practiced speed, knotting it tightly to the headboard. The silk bit into her skin, a delicious sting that made her squirm.
Hayasaka tested the bonds, tugging once, twice. Her breathing turned shallow and quick. "Dio… what are you—" Her question ended in a choked moan as he ripped her maid blouse open. Buttons flew across the room. Cool air hit her flushed skin; her lacy bra barely contained her heaving breasts. He didn't pause to admire. His mouth descended, teeth catching one nipple through the fabric and tugging hard while his tongue flicked relentlessly over the peak.
"Ahhn!" Hayasaka arched sharply off the bed, pleasure spiking through her like lightning. His free hand shoved her skirt up roughly, fingers hooking into her soaked panties and yanking them aside without ceremony, he plunged two thick fingers straight into her dripping heat, curling them viciously against that sensitive spot inside.
"Nnngh… Dio…" Her hips jerked involuntarily, walls fluttering around the sudden intrusion. He pumped fast and hard, thumb grinding merciless circles over her swollen clit. Wet, obscene squelching sounds filled the room with every thrust of his fingers.
"Squelch… squelch… schlick…"
"You're already this soaked just from a kiss?" he taunted, voice thick with amusement. "Pathetic. But fuck, you feel good clenching around me like that."
Hayasaka's head thrashed against the pillow, moans spilling freely now. "D-Dio… too fast ahh… I'm gonna…"
He pulled his fingers out abruptly, leaving her empty and aching. She whined at the loss, hips lifting instinctively, chasing the friction. Diego grabbed her thighs, spreading them wide with bruising grips, nails leaving crescent marks on her soft skin. He rubbed the fat head of his cock along her slick folds, coating himself in her arousal, teasing her entrance without pushing in.
"Beg," he growled, leaning down until their noses brushed. "Beg for my cock, Maid-san. Tell me how badly you want to be fucked."
Hayasaka's pride shattered under the throbbing need between her legs. "Please Dio fuck me… please…I need it… need you inside me…!"
His grin turned feral. With one savage thrust he buried himself to the hilt, stretching her open around his thick length. Hayasaka screamed, the sudden fullness bordering on pain, her walls spasming wildly as she struggled to take him.
"Nnngh… ahh… too big… Dio… !"
He didn't give her time to adjust. He set a punishing rhythm immediately, hips snapping forward with brutal force. Each deep thrust slammed her into the mattress, bedframe creaking under the onslaught. Skin slapped wetly against skin, loud and obscene.
"Plap plap plap plap
"Fuck look at you taking it so well," he grunted, leaning down to bite her shoulder hard enough to leave teeth marks. "Screaming like a little slut already."
Hayasaka's moans turned high and broken, tears of overstimulation gathering at the corners of her eyes. "Dio ahhn… deeper… please… harder…!"
He growled, hooking her legs over his shoulders to fold her in half, driving even deeper. The new angle let him batter her cervix with every punishing stroke. Her body shook with each impact, breasts bouncing wildly.
"Schlick schlick plap plap "
She came suddenly, violently walls clamping down like a vice around him as she screamed his name. Her release soaked them both, dripping down his balls. But Diego didn't slow. He fucked her straight through her orgasm, prolonging the waves until she was sobbing, oversensitive and trembling.
"D-Dio… too much can't ahhn…!"
"Take it," he snarled, gripping her hips hard enough to bruise as he pounded relentlessly. "You wanted this. Now you're gonna cum again on my cock."
He pulled out abruptly, flipping her onto her stomach. Hayasaka barely had time to gasp before he yanked her hips up, forcing her onto her knees. One hand fisted in her hair, pulling her head back sharply while the other guided his slick cock back inside her from behind.
"Ah…!" She cried out at the deeper penetration, face pressed into the pillow as he began thrusting again hard, fast, animalistic.
"Plap plap plap plap "
He reached around, fingers finding her clit and rubbing vicious circles while he railed her from behind. Hayasaka's moans turned into desperate, keening cries, body shaking as another orgasm built impossibly fast.
"Dio gonna cum… gonna cum again…!"
"Do it," he growled, yanking her hair harder. "Cum all over my cock like the needy little slut you are."
She shattered a second time, walls pulsing and fluttering around him as she screamed into the pillow. Her legs gave out, but Diego held her up, fucking her through the aftershocks until she was limp and trembling.
Only then did he let himself go thrusting deep one final time with a guttural roar, spilling thick ropes of cum inside her. He stayed buried to the hilt, grinding slowly as he emptied every last drop.
They collapsed together, both panting harshly. After a long moment, Diego loosened the ribbon around her wrists, rubbing the red marks gently a rare moment of care amid the roughness. He pressed a surprisingly soft kiss to her temple.
"Not bad… for your little provocation," he murmured, voice still rough. Hayasaka, utterly spent and covered in marks, could only smile weakly against his chest, already plotting how to push him again next time.
But for now, she simply curled closer, savoring the ache between her thighs and the possessive way his arms locked around her.
The night was far from over.
Diego pulled back just enough to let Hayasaka catch her breath, her lips swollen and glistening from the brutal kiss. Her chest heaved, nipples already stiff and aching beneath the torn remnants of her blouse. He traced one finger down the center of her sternum, slow and deliberate, watching goosebumps rise across her pale skin.
"You're shaking already," he murmured, voice thick with dark amusement. "And I've barely started."
Hayasaka tried to glare up at him, but the effect was ruined by the way her thighs trembled. "You talk too much, Dio."
His grin sharpened. In one smooth motion he wrapped the purple ribbon around her throat—not tight enough to cut off air, just enough to remind her who held the leash. He gave a gentle tug, forcing her chin up further.
"Open that smart mouth again," he ordered, "and I'll make sure you can't talk at all."
She parted her lips in defiance—and he immediately fed two thick fingers inside, pressing down on her tongue. Hayasaka moaned around the intrusion, the sound wet and muffled. He pumped slowly, letting her saliva coat his digits while his other hand palmed one breast roughly, thumb flicking the sensitive bud.
"Mmph… nngh…"
He pinched her nipple hard enough to make her back arch, then rolled it between his fingers in slow, cruel circles. Every twist sent jolts straight to her core. Her hips rolled uselessly against nothing, seeking friction he refused to give.
"Look at these pretty tits," he growled, squeezing the soft mound until it spilled between his fingers. "Begging to be played with. You love it when I'm rough, don't you?"
Hayasaka could only whimper in response, drool slipping from the corner of her mouth around his fingers.
He withdrew them with a wet pop, strings of saliva connecting her lips to his hand. Before she could speak he shoved her down flat on her back again, straddling her ribcage. His cock thick, flushed, and leaking hovered just above her chin.
"Time to put that mouth to better use."
Hayasaka's eyes widened, but the ribbon around her throat tightened just enough to make her gasp. She opened wide without being told twice.
Diego fed the head past her lips slowly at first, letting her adjust to the girth. Then he pushed deeper—past her tongue, toward the back of her throat. Her gag reflex kicked in immediately; she choked wetly around him.
"Gllk! Hrrk!"
He groaned at the tight, spasming heat. "That's it… take it deeper."
One hand fisted in her hair, holding her steady while he rocked his hips in shallow thrusts. The other kept tension on the ribbon, controlling exactly how much air she could pull in. Every time she struggled for breath he eased back just enough to let her gasp, then plunged forward again.
"Slurp… gluck… gluck… hrrrk…"
Tears welled in her eyes, mascara streaking down her cheeks. Yet she never tried to pull away. Instead her tongue flattened against the underside of his shaft, swirling messily as she hollowed her cheeks and sucked.
Diego's head fell back. "Fuck good girl. Just like that."
He let her work him for several long minutes—slow, sloppy, obscene—until his balls drew tight and his breathing grew ragged. Then he pulled out with a wet pop, strings of spit connecting her swollen lips to his glistening cock.
"Not yet," he rasped. "I want to feel you come apart one more time first."
He flipped her onto her stomach again, yanking her hips up high. Hayasaka's arms were still bound above her head; she could only press her cheek into the pillow and arch her back, offering herself completely.
Diego knelt behind her, dragging the leaking head of his cock through her drenched folds. He teased her clit with it, slow circles that made her sob with need.
"Dio please inside!"
He gave one shallow thrust just the tip then pulled out completely.
She whined, hips pushing back desperately.
"Beg properly."
"Please fuck me need your cock need it so bad !"
Satisfied, he slammed home in one brutal stroke, bottoming out so hard her whole body jolted forward. The ribbon around her throat pulled taut as he wrapped the free end around his fist, using it like reins.
"Plap plap plap plap "
He fucked her relentlessly, hips snapping forward with punishing force. Each thrust drove the air from her lungs in sharp, broken moans.
"Ah… ah… ah… Dio…!"
He reached beneath her, fingers finding her clit again and rubbing fast, merciless circles. The dual stimulation had her shaking, thighs quivering, walls fluttering wildly around him.
"Gonna… gonna come… Dio…!"
"Come," he snarled, yanking the ribbon just enough to make her gasp. "Come all over my cock now."
She shattered with a scream, back bowing, inner walls clamping down so hard it dragged his own release closer. But he forced himself to hold back, riding out her orgasm with deep, grinding thrusts until she was limp and trembling.
Only then did he pull out, flip her onto her back again, and hook her legs over his shoulders in a deep mating press. Her knees nearly touched her chest; the angle let him sink impossibly deeper.
"Look at me," he growled.
Hayasaka's hazy eyes found his. Tears streaked her face, lips parted on desperate pants.
He thrust back inside slow this time, deliberate, letting her feel every thick inch splitting her open.
"Nnngh… Dio… too deep…!"
He leaned down, folding her in half, forearms braced on either side of her head. His mouth found hers again messy, open-mouthed, tongues tangling as he began to move.
Long, powerful strokes. Each one dragged against every sensitive spot inside her.
"Plap… plap… plap…"
She moaned into his mouth, high and needy. Her bound hands scrabbled uselessly at the headboard. Her heels dug into his back, urging him deeper.
"Harder… please… Dio…!"
He obliged snapping his hips faster, harder, pounding her into the mattress. The bedframe slammed rhythmically against the wall.
"Thump thump thump "
Hayasaka's moans turned into continuous, broken cries. "Ah… ah… ah… coming… coming again…!"
This time he didn't hold back. He fucked her straight through her climax, chasing his own release with brutal, stuttering thrusts.
"Fuck gonna fill you up take it all "
With a guttural groan he buried himself to the hilt and came hard, thick pulses flooding her depths. Hayasaka whimpered at the heat, walls fluttering weakly around him as she rode the last waves of her own orgasm.
They stayed locked together for long moments, breathing harshly. Finally Diego eased her legs down, untied the ribbon from her wrists, and gathered her against his chest.
Hayasaka curled into him, boneless and sated, a small, dazed smile curving her swollen lips.
"…You're still a bastard," she mumbled against his skin.
Diego chuckled low, pressing a surprisingly gentle kiss to her forehead.
"And you're still mine."
The room fell quiet except for their slowing breaths and the faint, satisfied hum Hayasaka let slip when he lazily stroked her hair.
...
Day Two...
Having stayed up all night, Shinomiya Kaguya—with two massive dark circles under her eyes—finally saw Diego emerge from the room.
"...Feels freaking amazing—truly refreshed!"
Also having stayed up all night, Diego was in top form. He even felt he could effortlessly win the love of everyone from eighty-year-old grannies to thousand-year-old elf maidens.
"Tch. That's what you get for pissing me, Dio, off."
Diego's gaze swept over. With a smile, he walked straight toward Shinomiya Kaguya, glanced back at the room behind him, and lowered his voice: "By the way, Shinomiya—I'm taking a few days off for Maid-san. Just casually three days. She paid the price for offending me, Dio. From the looks of it, she's probably not getting out of bed anytime soon... Really troubling. Looks like I have to pay the price too—skip class for a few days to take good care of her..."
Whatever Diego said next gradually faded from Shinomiya Kaguya's hearing.
Her expression went blank. She nodded numbly, then shot like an arrow into Hayasaka Ai's room—leaving Diego blinking in confusion.
"Eh? So Shinomiya actually has sprinting talent?"
After Shinomiya Kaguya entered the room, she first caught a faint whiff of blood, then saw Hayasaka Ai asleep under the covers.
"Ha... Hayasaka! Are you okay—?!"
"No more...! I really can't continue...! I won't dare anymore...! If this keeps up, I'm gonna break!!!" Hearing someone call her, Hayasaka Ai jolted. In her half-asleep daze, she shouted again.
It's too late—!!
Hayasaka... Hayasaka has already... taken... my first...!!
Why did things turn out like this?
It was me—I was first. Whether meeting him or getting to know him, I was clearly the first person to encounter him...
No one told me Hayasaka was this real!!!
Tears welled in Shinomiya Kaguya's eyes. She crouched pitifully on the floor, clutching her head, forced to accept the bitter fruit of her own actions.
"Ka... Kaguya-milady..." Hearing the familiar voice, Hayasaka Ai trembled as she propped herself up and reached out toward Shinomiya Kaguya.
"Hayasaka! You're not mad at me anymore?!"
"Can't... get mad anymore... Dio—he—he's not human at all... and he didn't treat me like a human either..."
Having been treated like a small piece of bread spread with white cream all night—especially in vulnerable spots—Hayasaka Ai, heavily injured, passed out again.
"Wait—don't sleep yet! What was the first time like?!" Shinomiya Kaguya grabbed Hayasaka Ai's shoulders and hurriedly asked. "I'm really curious—tell me quick!"
"This is paid content."
"I'll pay! I'll approve three days' leave for you!"
Don't think I don't know—Dio already said he'd request three days off for you. Damn milady trying to freeload me!
"Heh... Who told milady to have zero experience sleeping with a boyfriend? Asking this is so cute~" Forced boot-up for two seconds, she left behind one mocking line before shutting down again.
Waaah—I won't make Hayasaka angry ever again!
This was the first time Shinomiya Kaguya cried so loudly.
Today's victor: Shinomiya Kaguya, crushing defeat! Hayasaka Ai, unable to rise again!
(Shinomiya Kaguya: I personally saw Brando-kun enter Hayasaka's room and not come out all night. If I'd known bragging would lead to this...)
(Somehow still unsatisfied Hayasaka Ai: If I provoke Dio into anger again next time, maybe I can...)
...
"Roar—my first time, huh?"