The Author is an Extra, The MC is a Reincarnator - Chapter 44 First Job [1]

James Woodrow has transmigrated into a strange world of magic as student in the prestigious Ainsworth Magic Academy. Oh and with him came the gigolo system. Watch how he navigates this strange world full of conspiracies while putting the system to full use by getting all the most beautiful MILFS on the campus.

From the outside, Nana’s life seemed simple. She had everything she had ever wanted: a cute but rascally pair of twin brothers, a best friend, and her own restaurant. Nana couldn’t ask for anything more; she was happy and content in her life.

After Reincarnating into Naruto World at the Warring State Era as an Uzumaki, Masahiko thought that he got a useless System. He lived for 48 years as a normal, below average Uzumaki Shinobi.

That changed when he finally knew how the system works the day of his 49th Birthday!

- Description from Novelupdates