May served as a councillor for Durnsford ward on the London Borough of Merton from 1986 to 1994, where she was Chairman of Education (1988–90) and Deputy Group Leader and Housing Spokesman (1992–94). In the 1992 general election May stood unsuccessfully for the safe Labour seat of North West Durham, coming second to incumbent MP Hilary Armstrong by 12,747 votes (27. 6%) to 26,734 (57. 8%), with future Liberal Democrat leader Tim Farron coming third. May then stood at the 1994 Barking by-election, which was prompted by the death of Labour MP Jo Richardson. The seat had been continuously held by Labour since it was created in 1945 and Labour candidate Margaret Hodge was expected to win easily, which she did, with 13,704 votes (72. 1%). May came a distant third with 1,976 votes (10. 4%). Ahead of the 1997 general election, May was selected as the Conservative candidate for Maidenhead, a new seat which was created from parts of the seats of Windsor and Maidenhead and Wokingham. She was elected with 25,344 votes (49. 8%), almost double the total of second-placed Andrew Terence Ketteringham of the Liberal Democrats, who took 13,363 votes (26. 3%).