Pain, Pain, Go Away - Chapter 3: Scoring Points

One night she gets drunk and mistakes the most well-known Mafia boss for a host and intends to sleep with him.

Oh my! What should I do? It’s best to run away!

- Description from Novelupdates

When Simon dies, it turns out there's more to combat than lightning reflexes with his controller, and the path to becoming a hero is more brutal than he can imagine as he descends into The Pit. Death after Death is a dark, time loop/Isesaki story with roguelike elements, that explores some of the common tropes in a different light.

[Warning: Mature content, lemons, comedy, MILFs, NTR, and a villainous protagonist!]_____[Ding! Congratulations, Villain! Your survival chance is 0.01% unless you NTR every hidden boss in this world. Start now or perish!].....James Tanner’s life could be summed up in one word: boring. After barely a week of being a rookie cop, he met his end courtesy of a speeding red sports car.But death wasn’t the end. It was just the beginning.When James woke up, he found himself in Aurendral, inhabiting the body of a rich young master who had spent years blind due to a mysterious condition.Fortunately, the blindness vanished when James merged with the body, leaving him with perfect vision—and one massive headache.[Ding! Issuing First Death Mission: NTR the hidden boss in this region within 90 days… or perish.]What choice did he have? Forced into the role of a scheming villain, James Tanner was about to shatter conventions, steal hearts, and become the strongest and most fearsome seducer this world had ever known.Because if he was going to be a villain, he might as well be the best.[Note: MC takes other guys' women, they don't take his.]