Justine (1797), Marquis de Sade

Sentenced to death in pre-revolutionary France, a young woman, Therese, recounts the traumas that led to her downfall. Therese is the assumed name of the eponymous heroine, whose horrific story of multiple sexual assaults from the age of 12 onwards resulted in de Sade’s imprisonment for the last 13 years of his life.

From the author who put the Sade in sadism, Justine's quest for virtue and her subsequent misfortunes make the misery of Samuel Richardson's Pamela almost appealing by comparison.

Women in Love (1920), DH Lawrence

"I do not claim to be a literary critic, but I know dirt when I smell it, and here is dirt in heaps-festering, putrid heaps which smell to high Heaven." A ringing endorsement of DH Lawrence's Women in Love from his contemporaries.

Like most of his other novels, Lawrence's sequel to The Rainbow (1915) provoked outrage for its sexual content. The Brangwen sisters' affairs and intertwining relationships in early twentieth century England are as much to do with emotional and intellectual connections as they are with sex.

Lady Chatterley’s Lover (1928), DH Lawrence

Lawrence was back in the bad books a few years later with the publication of his novel about an affair between an upper class woman and a working class man. Lady Chatterley’s Lover shocked audiences with its vivid sexual scenes and use of “unprintable language”. The author drew on his own unhappy relationships and other real-life examples of friends and acquaintances for the story.

Constance Chatterley’s husband is paralysed from the waist down due to a war injury. Sexually and emotionally unfulfilled in her marriage, she begins an affair with the gamekeeper Mellors.

Country Girls (1960), Edna O’Brien

Less sexually explicit in its content than some of the other titles in the list, Edna O’Brien’s first novel nonetheless paved the way for debate on female sexuality in an Ireland that had succeeded in repressing such topics.

Cait and Baba cast off their convent school upbringings for the lights of Dublin in the sixties. Exploring new relationships with men and escaping from the confines of rural life allows them to learn more about each other and themselves.

Valley of the Dolls (1966), Jacqueline Susann

“Love shouldn’t make a beggar of one. I wouldn’t want love if I had to beg for it, to barter or qualify it.” Susann’s roman à clef was the bestselling novel of the year in 1966 and her tale of female oppression in a patriarchal world has since sold 30 million copies worldwide.

The title refers to women as objects or playthings, but also pertains to her characters’ addiction to sleeping pills and antidepressants. Centred on the lives of three women – Anne, Neely and Jennifer – the book begins in the superficial world of Broadway in 1945 and follows the close-knit group of friends over the next 20 years.

Portnoy’s Complaint (1969), Philip Roth

With his explicit story of a “lust-ridden, mother-addicted young Jewish bachelor,” Philip Roth found fame and notoriety in sixties America. The book’s protagonist Alexander Portnoy delivers his complaints in a humorous monologue to his psychiatrist Dr Spielvogel. Graphic language and vivid descriptions of masturbation with various props, including a piece of liver, sparked huge controversy.

Banned in libraries across the US, Australia went one step further by deeming the novel a “prohibited import” and attempting to prosecute publishers and booksellers who carried it.

Fear of Flying (1973), Erica Jong

An important work in the development of second wave feminism, Erica Jong’s bestselling novel debunked traditional assumptions about sexuality and gender, coining a new phrase for a sex act along the way.

Isadora Wing is the book’s 29-year-old American narrator, a writer of erotic poetry stuck in an unfulfilling marriage. A trip to Vienna with her husband leads her to explore her fantasies with other men. Relating Isadora’s adventures and misadventures with a frankness usually reserved for male characters, Jong’s novel ignited the debate about women and sexual liberation in seventies America.

Forever (1975), Judy Blume

Still a favourite among teenagers almost 40 years after publication, Blume’s book offers a candid account of sex and virginity from a teenager’s perspective. Demystifying the topic and exploring notions of fidelity and monogamy, the American author’s bildungsroman looks at a seventies youth culture trying to escape from traditional mores.

In addition to the relationship between main characters Katherine and Michael, Blume also explores issues of depression, homosexuality and religion in one of her most enduring works.

Oranges Are Not the Only Fruit (1985), Jeanette Winterson

Winterson’s award-winning roman à clef tells the story of a young girl growing up in a strict Pentecostal community, who must break the ties of family and religion to forge her own path. Realising she is gay, a teenage Jeanette survives her isolated existence and her mother’s controlling nature through her love of books and education.

Winterson's excellent Why Be Happy When You Could Be Normal? (2011) is a non-fictional memoir account of a similar story.

Fifty Shades of Grey (2011), EL James

The book that changed the world's view of self-publishing, Fifty Shades of Grey became the first of a trilogy by EL James that has since has sold more than 100 million copies worldwide, translated into more than 50 languages. Anastasia Steele is a young college student, at once repelled and attracted to business magnate Christian Grey and his salacious proposals that include, among other temptations, a clothing budget, a personal trainer and a playroom full of BDSM equipment.

Originating as fan fiction to Stephenie Meyer's Twilight series, the Fifty Shades franchise has itself spawned a new generation of erotic fiction.