This manga should never have established that having sex with a woman was a game winning requirement before the end of 365 days. He now has 2-ish viable options, even if they are crazy, he bangs one and he wins the game, game over but now author-san no longer makes that a thought in his mind, instead author-san wants us to believe that the MC is more into completing subjugation's than completing a game winning component, especially with a girl who no longer would kill him if she took his first time or whatever.