In the beginning Masako had only thoughts of scoring Oliver as a husband to appease her family. They would have made a great match; both had supernatural abilities, were intelligent enough to be the best with their abilities, and both were stoic and beautiful. Neither cared much for emotions so it wouldn't even matter if it was a loveless marriage. The blackmail had started as a means to distance him from that childish assistant of his. Though Oliver himself was oblivious to it, she had noticed how he cared for the silly high schooler and she knew his interest would kill Masako's chances. She wouldn't risk it. And if she started developing feelings for Oliver what did it matter?
Despite her careful planning, however, Mai somehow managed to draw Oliver to her time and again. It was infuriating. It wasn't like she could bring herself to hate Mai either. The girl was too nice, too naïve. Masako found herself frustrated to no end. And then Urado's mansion happened. That was when Masako realized she was starting to fall for Mai.
As a result the nature of Masako's relationship with Oliver changed. No longer did she want to pursue a marriage with him. Instead, her blackmail was to ensure not only that Oliver wouldn't pursue Mai but to also protect her from the inevitable fallout when she learned "Naru's" true identity. It became a one-sided contest; how far were they both willing to go for Mai?
And then Naru found Gene. Masako stayed as close to Mai as possible knowing that heartbreak would be coming. She managed to find the time to corner Naru. "Don't hurt her," was all she could say. It was a plea for mercy that went unheard. The morning Naru's family left for England, Mai awoke in tears.
Masako ached for the girl she was falling for. So she made every effort to make Mai smile. It paid off. The two grew closer as a result and soon they were nearly inseparable whenever Masako's schedule allowed for it.
Two years passed and in that time Mai grew into herself in front of Masako's eyes. In all that time Masako had fallen more in love with Mai and was even working up the courage to tell her. She even had a day planned where she would take Mai out and tell her how important she was. Her plans were destroyed due to Naru making a reappearance in their lives. And while at first Mai seemed not to have fallen back to her feelings for Naru, she eventually caved. When Mai asked for advice Masako would simply reply, "Do whatever makes you happy."
Masako would never admit how much she was hurting. She found herself unable to deny Mai anything and even allowed herself to be pulled into Mai's wedding as the maid of honor. She didn't allow herself to cry. Mai seemed to sense her feelings and pulled her into a dance at the reception. "Will you be alright?"
Masako couldn't answer but vowed to stay in Mai's life in whatever way she was needed. She could adapt. It would be hard but…. then Oliver stole Mai away to London to run BSPR. She would have followed if not for Mai's words: "Please do something for yourself. We can visit each other all the time, but please don't build your life around me. I couldn't ask you to sacrifice your feelings like that."
It hurt. But Masako could see that Oliver had won and that Mai was happier for it. So she stayed. Worked on her career. And visited Mai whenever possible.
A/N: So in the spirit of posting at least something I've written in the last decade, I figured this might as well go somewhere since it's finished. (For those who follow other works of mine, I promise I'm getting back to them but it's taking some work since my writing style has changed.) If you'd have asked me when I first joined this fandom if I'd ever ship Masako with Mai I would have straight up laughed in your face. This particular fiction idea started out as a song prompt turned "what if?"
