In 1933, May served as the housekeeper for Max and Charmian Bond. One day, whilst cleaning the house Max introduced her to James, calling her an absolute treasure. She and James exchanged greetings before she returned to her work cleaning up the house. Over the next few days, James would come to learn that May's gruff exterior was just her shyness manifesting. As he got to know her better, he learned that she was kind-hearted and very devoted to his uncle Max.
She was later present when Bond awoke several days after the assault on Randolph Hellebore's estate. She was preparing breakfast and was there while Charmian explained to Bond the circumstances of Max's death. She attended the memorial service of Max alongside her husband. Bond bade goodbye to May right before he left for Eton.
May was the third to be interviewed for her position as James Bond's housekeeper, and was the only one of them not to fall for the man's ruse of being employed by the government's Tourist Department, and assured him that she wouldn't ask questions if he wouldn't lie to her, a display of her keen mind that earned her the job.
Forever and a Day (2018)
May had been working for Bond just over a year by 1950. One morning, after Bond returned from one of his trips away, she spoke negatively of the American attack on Chinju in Korea, having thought the world had had enough of war, and blaming Joseph Stalin, whom she had never really trusted, before leaving Bond to his breakfast.
When the time came for her reluctant retirement, May suggested that her niece Donalda take her place, and apprenticed her for a period of two weeks before handing over her duties entirely.