Debauchery is Underrated

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Summary: An infamously shrewd Guild Leader who got Isekai'd into the MMO game Eldar Online, awakens to find himself trapped in yet another game-like world. Starting from scratch, he quickly finds himself accumulating a party of 'hopeless hotties'-- beautiful women with terrible character builds and sexual proclivities that get in their ways at the worst possible times. But instead of complaining about it or trying to fight it, he leans into it and does the best he can with the material he has. After all, he knows a thing or two about kink, himself, having originally come from modern-day Earth. His exploits will soon have each of them wondering what they've gotten themselves into.

Author's Notes: I watched Konosuba long ago, and I couldn't help but feel like Best Girl Darkness deserved a responsible Dom. So when FiftyFiftyFifty posted Hopeless Hotties, a CHYOA about a Konosuba-type situation with basically three Darknesses in the party, I couldn't resist making a fanfic of that, replacing the MC with everyone's favorite "Villain in Glasses" from Log Horizon. I'm still writing new chapters, and I have a tendency to update the old chapters to retcon in the foreshadowing, so watch out for that. If something doesn't make sense, check the Story Map for any Chapter Updates that may explain/justify it.

Shiroe slowly came to his senses, laying in an unfamiliar field. His memories of his past life... two past lives...? ...were a distant blur. He instinctively raised his hand to his chin, but Eldar Online's in-game UI didn't pop up. Was he finally back on Earth? He closed his eyes, and tried to focus on his stats and abilities. From somewhere deep within himself, he found a version of what he was looking for:

Shiroe
Level 1 Tactican
Empathetic Insight - know allies' strengths
(Unspent Ability Slot)

So it was back to basics. He was still in a game-like world, but an unfamiliar one, and his character progression had been completely reset to zero.

So be it.

Shiroe didn't know if it was possible to regain his memories, or to get back home. He didn't know any of this world's rules yet. He didn't even know how worked here. But he did know one thing.

In a past life, he had mastered the rules of the game. And even though it had earned him the nickname "the Villain in Glasses," he had changed the world. (He hoped, for the better.)

If he'd done it before, he could do it again.

He only hoped that his own arrogance wouldn't be his downfall.