Knowing Brother - Chapter 41

Untolerated by heaven, a boy was restricted by the most powerful spell.

Jiang Bai woke up one day and found with shock that he had transmigrated to a parallel world that is similar to Earth. There, he was granted a cheat system to help him forge the path of a tyrant in this new world. He was now stuck in this parallel world body, the body of a weak and cowardly person. Join Jiang Bai as he rose to the top in this new world!

- Description from Novelupdates

I, Hyoudou Issei, am a 2nd Year High school student and my age is equal to the number of years I haven’t had a girlfriend. And, someone like me got a girlfriend! I’m sorry buddies, I will walk the path of becoming an adult before you guys! – That’s how it was supposed to be, but why did I get killed by my girlfriend!? I still haven’t done anything yet! Are there no Gods in this World!? And, the person who saved me is the most beautiful girl in my school, Rias Gremory-senpai. I learned the shocking truth from her who isn’t a God but a Devil. “You have reincarnated as a Devil! Work for me!” Lured by Senpai’s breasts and treats, my life as a reincarnated Devil began. So the “Academy×Love Comedy×Battle Fantasy” starts here with just aggressive and worldly desires!

She was drugged by her ex-boyfriend and had her first night with a mysterious man.