The 35-year-old man was also jailed for two years for his offence, following an investigation into a paedophile ring.
The books include Anne Frank's Diary and the poems of Emily Dickinson.
Judge Paola Di Nicola reportedly hoped the books would help his 15-year-old victim understand the damage done to her dignity as a woman.
However, one author whose book was among those on the list told Corriere della Sera newspaper that it would have been better if the judge had read the works to the convicted man instead.
"Adolescence is not the time for reflection. What he did was much worse: an adult who, knowingly, paid for sex with a minor," said Adriana Cavarero, a philosophy professor at Verona university and author of Notwithstanding Plato.
The ruling follows a three-year investigation into a major paedophile ring in Rome that preyed on two girls aged 14 and 15 in the upmarket suburb of Parioli. The mastermind has been jailed for nine years.
The teenagers were lured into sex work with cash that they used to buy new clothes and the latest mobile phones, investigators said.
An Italian judge has ordered a man convicted of using an underage prostitute to buy her 30 feminist books and two feminist films.