After graduation, she took odd jobs in the theatre and her first novel, Oranges Are not the Only Fruit, was published when she was 24, which helped her win the Whitbread Award for a First Novel. Passion appeared in 1987. At that time, she became a full-time writer. Over the next years, she published Sexing the Cherry in 1989, Written on the Body in 1992, Art and Lies in 1994, The Power Book in 1995, Light Housekeeping in 2004 and so on. Oranges Are not the Only Fruit and Sexing the Cherry are the companion volumes. Readers can find coherent thoughts in the former , but in the latter, unconventional thinking can be easily found. Meanwhile, the rebellious consciousness developed from a spark in Oranges Are not the Only Fruit to a sea of a fire in Sexing the Cherry. 

Set in 17th century London, Sexing the Cherry is about the journeys of a mother, known as the Dog Woman and her adopted son, Jordan. The journey is in a space-time flux: across the seas and across time. The Dog Woman is somewhat grotesque. She is giant and hideous but her son feels pride of her. Over the journey, Jordan falls in love with Fortunata, a dancer who may not exist at all. In search for his lover, he goes across seas and time along with his idol, Tradescant, a botanist, explorer and traveler. On the way, he knows that Fortunata is the youngest one among the twelve princesses. The story is adapted from Shoes that Were Danced to Pieces , a classical fairy tale. Among these princesses, the fifth princess has the similar experiences with the witch in Rapunzel which is a new version rewritten by Winterson. In addition, the youngest princess tells Jordan a story of Artemis which is a parody of a Greek myth.