Chapter 50: Sister In Harem?!

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"Oh… well, how long will that take?" Issei asked, his curiosity getting the better of him.

Several of the devils couldn't help but look at him with disbelief, wondering how he could be so upbeat and seemingly callous in such a critical moment.

"It'll probably last an hour or two," Sona informed him. "But what exactly do you want from me?"

"My childhood friends want to enroll in Kuoh Academy, but they have some rather unusual backgrounds, and you know how challenging it can be to get transfers approved without a little influence. So, I was wondering if you'd be willing to expedite their paperwork for me," Issei earnestly requested.

"Childhood friends?" Sona blinked, slightly taken aback by Issei's request.

"Yeah… they're just humans. Nothing you guys need to worry about," the dragon within Issei clarified.

"I suppose I could do that…" Sona said slowly, somewhat surprised that Issei would seek something so simple from her.

"Why should she? You're not willing to help us, so why should we help you?" challenged a white-haired freshman devil in Sona's peerage.

"Koneko makes a valid point," Kiba chimed in, nodding in agreement.

'Oh god… please don't tell me they're going to ask me to help Gremory just to get Xenovia and Irina enrolled,' Issei groaned inwardly, rolling his eyes at the potential predicament.

Sona regarded Issei with curiosity, her offer clear. "I would be willing to do that for you, Issei Hyoudou… if you agree to fight on Rias' behalf."

"Dang, talk about cornering me like this. Should've picked a better time to ask," Issei sighed, feeling a bit trapped by the unexpected turn of events.

Before anyone could respond, a vibrant orange-red summoning circle materialized in the room, followed by the sudden appearance of 16 individuals, all devils, with only one of them being male. Issei couldn't help but cringe at the sight of the male devil who stood before them, clad in a hideous burgundy suit, with a slightly scruffy appearance and a self-assured grin.

He sported medium-length blonde hair and striking blue eyes, exuding an air of arrogance and cockiness. His coat was casually open, and the white undershirt beneath was unbuttoned at the top.

"Well, well, well, Rias darling, are you prepared for our Rating Game?" the male devil chimed in with a smirk.

Rias responded with a stoic expression, "Yes…"

Unfazed by her response, he playfully taunted, "Oh, what's with the long face, darling? You're the one who wanted this, after all."

Rias glared at him, her resolve unwavering, "Even if you win, I'll never love or respect you."

The devil didn't seem perturbed by her words and confidently retorted, "You don't have to love Riser, darling… you just have to belong to him. Once Riser has Sirzech's baby sister in his harem, he'll be the most respected young devil in all of Hell. Then Riser Phenex will have the greatest harem in the world," he boasted.

'What an insufferable guy…' Issei thought to himself, observing Riser throw an arm around Rias, further adding to the tension in the room.

With an air of arrogance, Riser turned his attention to Rias' peerage, a disdainful grin crossing his face. "Is this your peerage, Rias? How cute… you don't even have half of Riser's. Not that it would matter anyway… because Riser is invincible!"

Unable to hold back, Issei interjected with a mix of amusement and annoyance, "Wow… is this dickhead actually referring to himself in the third person?"

The cocky blonde devil eyed Issei with arrogance, "And who might you be? Another one of Rias' temporary fillers, I presume? How amusing… she could only find one? Hahaha!"

"I wouldn't laugh at him, Riser… Issei is half-dragon, and he's no pushover," Sona intervened calmly, defending Issei's capabilities.

Unfazed, Riser laughed heartily and even pointed a finger at Issei mockingly, "A half-dragon?! Ahahaha!"

Issei felt his temper rising, but he maintained his composure, retorting, "I fail to see what's so funny about it."

"You believe a mere half-dragon could match the might of the esteemed House of Phenex?! Not even a full dragon could stand a chance against Riser! Look at this weakling! The thought of some half-breed dragon challenging Riser's ultimate harem peerage, let alone Riser himself, is laughable!" Riser sneered, reveling in his own arrogance.

Deep inside, Issei seethed with anger while outwardly remaining composed. No one had ever laughed at him like this, and he couldn't let it slide.

'This guy is probably the most insufferable devil I've ever encountered… Gremory wasn't exaggerating,' Issei seethed inwardly.

"A harem peerage, you say? Is that why you're surrounded by a bunch of weak little girls?" Issei couldn't help but laugh in disdain.

Riser's expression darkened, and he shot a venomous glare at Issei, "What did you say, you trash? Are you insulting Riser-sama's ultimate harem? You're just jealous of Riser's power and status. You'll never possess the power, women, or fame that I do!"

Issei regarded Riser with amusement, his confidence unshaken, "Wow, so you do know how to talk in the first person… and here I thought you were just an insufferable fool. But let's be clear; there's nothing about some bratty little bitch like you that I would ever envy. All I see in front of me are 16 devil girls. You're the punchline, pal."

"How dare you insult Riser-sama's manhood?!" protested one of Riser's knights angrily.

Issei smirked at them defiantly, "Yes, I dare. And you, sir, are delusional if you think this is the ultimate harem."

"Flamer?! What did you just call me?!" Riser's anger flared in response to Issei's remark.

Issei responded playfully, "Oh, my apologies. Would you prefer Riser-chan, then? Or maybe Riser-tan?"

"You have no idea who you're messing with," a blonde girl with distinctive drill curls chimed in, her voice filled with fiery determination. "We're phoenixes… immortal birds of fire. Riser Onii-sama will wipe the floor with some punk like you!"

Issei momentarily paused, clearly distracted by the girl's unique hairstyle. "Are those actual drill curl twin-tails!? Haha, I've never seen a girl with such impressive drills before! But wait… did you just call Riser your brother? What kind of guy puts his sister in his harem?"