Great game, but it seems to be impossible to race with black d. as the races take place in midnight but I can't bring out my motorcycle and Rei at the same time.
Since you can only bring Rei with you at midnight if you interact with her to go to work at the casino, but when you go back home, you go to sleep automatically and can't take Rei with you. If you took out your motorcycle to go to work at the casino, which is the only way to get it out at midnight, Rei won't be with you.
Tldr: You can't take both the bike and Rei with you, making it impossible to race with black d.