These 12 Erotic Poems and Novels Throughout History Make Fifty Shades of Grey Seem Tame

“Signor Dildo (You ladies all of merry England)” (1673)

In November 1673, Mary of Modena arrived in London for her royal wedding to King Charles II’s brother, James, the Duke of York. Parliament objected to the match because Mary was an Italian Catholic. Despite his friendship with the king, John Wilmot, 2nd Earl of Rochester, one of the English Restoration period’s most popular satirists, frequently ridiculed the licentious court. Wilmot and his friends responded to Mary of Modena’s arrival with “Signior Dildo,” a satirical poem on the trade advantages of the diplomatic marriage.

Wilmot used the poem to comment that the women of England would be more than acceptable to the importation of dildos, referred to as “the Italian device” in Restoration England. Using personification to turn the device into an Italian nobleman who fascinated the women of the royal court, Wilmot and his friends sent a clear message: Charles II’s mistresses were more captivated by the nobleman, making a mockery of the king. With the release of “Signior Dildo” and “In the Isle of Britain,” which also criticized the king’s extramarital affairs, the furious Charles II banished Wilmot from the court, and their relationship never recovered before the poet’s death in 1680.

The Carnal Prayer Mat (1693)

Continuously banned since its publication in 1693, The Carnal Prayer Mat, attributed to playwright Li Yu, is no more graphic than erotica today, but its connection of religion and lust shocked seventeenth-century Chinese society. The author tells the story of the lustful scholar Weiyangsheng, who has multiple affairs with married women after surgically enhancing the size of his penis. One of the scorned husbands elopes with Weiyangsheng’s wife, Yuxiang, selling her into prostitution. When she reunites with her husband, Yuxiang is so ashamed that she commits suicide. Realizing his mistakes, Weiyangsheng castrates himself, devoting himself to religious prayer and seeking enlightenment.

Scholars treat The Carnal Prayer Mat as an allegory that satirizes popular Confucian works on reaching enlightenment. While the author does not judge the characters for their actions, there is a moral to the story that focuses on moderation in sex; overindulging in sexual activity can lead to one’s downfall. The novel satirizes late Ming and early Qing dynasty caizi jiaren literature, in which a scholar falls in love with a beautiful woman. While caizi jiaren texts focus on spiritual love, The Carnal Prayer Mat emphasizes sex as a fundamental aspect of relationships.

Fanny Hill (1748)

The erotic novel by John Cleland, Memoirs of a Woman of Pleasure, also known by its nickname Fanny Hill, scandalized eighteenth-century British society with its descriptions of prostitution, flagellation, and same-sex encounters. In an exchange of letters to her friend, a former prostitute reveals all of the juicy details of her former occupation, much to the chagrin of her friend. Cleland’s epistolary novel, published in 1748, remains one of the most censored books in history, enduring obscenity trials for over two hundred years after its initial publication.

In her letters to her unidentified friend, “Madam,” Fanny Hill reveals her past, describing her participation in a lesbian encounter with another prostitute, an orgy, and a flagellation session. Madam is shocked by much of what Fanny explains, such as witnessing a sexual encounter between two men. Fanny also details her fellow prostitutes’ sexual experiences, revealing a culture where the women encourage and congratulate each other on their skills.

As shocking as it was to its audience, Fanny Hill was a critical work of literature because it rejected the traditional form of the novel. It created a story in which sexual pleasure is not a shameful thing, becoming the first eighteenth-century British novel to do so. Epistolary novels were a popular genre, but sex was a taboo subject. The only mention of sexuality in British literature before the publication of Fanny Hill was in the form of conduct novels, which encouraged women to live honorably and reject the enjoyment of sexuality.

Despite challenging traditional conduct novels of the time, Fanny Hill still has characteristics of the literature of the age. It is a morality tale that extolls the virtues of British society, considering all non-heterosexual unions to be subversive and denouncing them. When Fanny writes to her friend about how she observed two men having sex, she obviously condemns it, using words such as “attack” and “harass” to describe it. The novel focuses on approving heterosexual unions and the importance of love matches, shown by the ending in which Fanny marries one of her first customers.

120 Days of Sodom (1785)

Four wealthy men retreat to the Chateau de Silling, a brothel located in an isolated eighteenth-century German castle. When they arrive, four madams share their many experiences with men that range from nonpenetrating sexual fetishes to violent encounters. The four men re-enact what they have just heard on the prostitutes of the castle, torturing and killing them. This isn’t a horror movie; it’s the plot of 120 Days of Sodom by the French nobleman the Marquis de Sade.

While the author describes horrific sex acts in graphic detail, he insists that the reader should not condemn the story because everyone disagrees on what should be considered “erotic.” The Marquis de Sade’s works are well-known for their sexual violence, using his own life experiences as inspiration. In 1785, French officials arrested the Marquis de Sade for assaulting prostitutes; while he was sitting in the Bastille, he wrote 120 Days of Sodom on a scroll of papers smuggled into his cell.

In early July 1789, after he created a disturbance, his jailers transferred him to Charenton Insane Asylum, but he didn’t have time to grab his manuscript. A few weeks later, on July 14, 1789, a French mob stormed the Bastille, initiating the French Revolution; the Marquis was devastated, reflecting afterward that he wept “tears of blood” at the loss of his manuscript. The scroll was later discovered, hidden in the walls of his cell.

The novel had its supporters despite its disturbing content of sexual violence. A Berlin psychiatrist anonymously published it in 1904, believing it was a critical study on sexual fetishes. In the 1950s, feminist existentialist Simone de Beauvoir reacted negatively to the French government’s plans to burn the original manuscript, analyzing the importance of the Marquis de Sade for highlighting man’s capability for evil. Some modern scholars identify 120 Days of Sodom as a satire of the Enlightenment works of the period that emphasize man’s virtues.

The French eventually accepted the Marquis de Sade’s contributions to French literature, declaring the original scroll a national treasure after years of legal struggle for ownership of the manuscript in 2017. Through 120 Days of Sodom, and his other works that explore the connection between sexual pleasure and violence, the Marquis de Sade’s name has served as the inspiration for sadism, the term used to designate sexual pleasure achieved through violence.

The Lustful Turk (1828)

Set in Georgian England, the epistolary novel The Lustful Turk tells the story of two English gentlewomen who become sex slaves in a harem in northern Africa. Writing to her friend Sylvia, Emily Barlow describes how Arab pirates kidnapped her during her journey to India in 1814. After Ali, the dey of Algiers, buys her, he brings her to his harem as his sex slave; after her encounter with Ali, Emily finds that his rough treatment of her awakens her sexuality.

Emily embraces her newfound lust, which offends Sylvia; Ali steals one of Emily’s letters, and he orchestrates the kidnapping of Sylvia herself. He arrives at the slave market, impersonating a Frenchman, deceiving her into marriage to save her from sexual slavery. They get married, and Ali returns to the harem with Sylvia, and he has sex with both Sylvia and Emily together. A new arrival castrates Ali before killing herself. Ali then has his missing parts preserved in wine and presents them as gifts to Emily and Sylvia before sending them back to England.

The story may seem far-fetched to us now, but the idea of being kidnapped by Arab pirates was eerily familiar to nineteenth-century British audiences. Even though the practice was in decline, Arab Barbary pirates had been attacking British ships and coastal towns for hundreds of years, making slaves of the people they captured. The idea of “white slavery” was well-known, and it instilled fear in everyone who lived on the English coast or sailed on the open sea because capture was always a possibility.

The fear of Arab pirates made its way into the literature of the time; non-Western settings in Georgian and Victorian novels became places that were the opposite of contemporary British values. Non-Western people, in particular, were characterized brutally, the opposite of civilized society. Literary scholars have analyzed the setting of the harem in Georgian and Victorian literature as a place of unrestrained morals and open sexuality, making the audience appreciate the refined British society in which they lived.

Venus in Furs (1870)

Leopold von Sacher-Masoch’s Venus in Furs is an exploration of dominant and submissive roles in sexual relationships, a behavior documented in ancient texts and art. In the novel, the European nobleman Severin von Kusiemski approaches the object of his desire, Wanda von Dunajew, and submits himself to her, wanting to be her slave. Despite her initial hesitation, Wanda becomes intrigued as Severin encourages her to treat him more cruelly.

Severin eventually reveals the root of his submissive behavior: his cruel aunt, who liked to wear fur, abused him in his childhood, making him thank her for beating him. When the couple travels to Florence, Severin poses as Wanda’s servant, and her mistreatment of him intensifies. Eventually, Wanda loses interest, finding that she would rather be the submissive partner to another man, and she leaves Severin. Sacher-Masoch concludes the story by stating that women can only be dominant or subservient to men and that men and women could never be equals.

Much like the Marquis de Sade, Leopold von Sacher-Masoch incorporated his sexual preferences in Venus in Furs. According to a memoir published by his first wife, Aurora von Rümelin, his sexual proclivities are shockingly similar to Severin’s character in the novel; she also detailed his multiple affairs, especially with an aspiring writer named Fanny Pistor, the inspiration for Wanda. In his 1967 study on the difference between sadism and masochism, “Coldness and Cruelty,” twentieth-century philosopher Gilles Deleuze identifies Venus in Furs as an autobiographical work, with its depiction of female sexual dominance that Sacher-Masoch employed in his personal life.

Sacher-Masoch rejects the prevailing notion that all men need to be the dominant partner in relationships through his exploration of Severin and Wanda’s relationship. In 1886, Austrian psychiatrist Richard Freiherr von Krafft-Ebing published his book Psychopathia Sexualis, in which he identified masochism, a term derived from Sacher-Masoch’s name, as the sexual preference of being under the power of a dominant partner. Sacher-Masoch was not happy with his name being used to describe a sexual fetish, yet we are still familiar with von Krafft-Ebing’s definition today. Sacher-Masoch’s name has become synonymous with the type of relationship that he describes in Venus in Furs, which is arguably his most famous work.

The Story of the Eye (1928)

In 1928, Georges Bataille published one of the most sexually disturbing and graphic novels of the twentieth century, and it is arguably one of the most shocking examples of erotica in the history of literature. In The Story of the Eye, the narrator and his lover, Simone, who has a fondness for inserting bulbous items into her body for sexual pleasure, indulge in multiple fetishes, such as exhibitionist sex, multiple partners, and orgies. Throughout the novel, the narrator describes his relationship with his girlfriend Simone and another woman, with their exploits becoming more and more depraved.

The callousness of the couple’s sexual exploits is enough to make the reader’s skin crawl. They have sex often in view of Simone’s mother. They include a mentally-ill woman in their relationship, who eventually loses her grip on reality. When she commits suicide, the couple has sex next to her dead body. Simone and the narrator leave the country, where they meet an English aristocrat who encourages their behavior. When the three visit a church, Simone seduces a priest and strangles him to death. The couple and the aristocrat escape to Andalusia where the aristocrat buys a yacht for them to continue their sexual debauchery.

Georges Bataille was an intellectual who explored the meaning of life and experience through his writing, incorporating constant themes of transgression and eroticism in his texts. While literary circles largely discredited his pornographic works in his lifetime, considered only for their inclusion of shocking sexual fetishes, later scholars have analyzed Bataille’s The Story of the Eye, as part of a twentieth-century literary movement called “literature of transgression.” The philosopher Michel Foucault used The Story of the Eye as a crucial work in the development of transgression as a literary device in his 1963 article “A Preface to Transgression.”

Transgressive themes are present throughout literature that provides social critique, especially in erotica that detail fetishes and sexual exploration. Characters in transgressive fiction feel trapped by society’s restrictions or codes of behavior, engaging in drugs, sex, or alcohol to rebel against these restrictions. Transgressive literature didn’t emerge as a particular genre until the twentieth century, fully reaching its height by the end of the century; it remains one of the most influential and commercially successful trends in literature today.

The Tropic of Cancer (1934)

As a member of “The Lost Generation,” Henry Miller was one of many expatriate writers and artists who found solace in Paris during the interwar years. Art and literature became autobiographical, describing the directionless feeling that writers and artists felt from their sobering experiences of surviving World War I. Literature explored the methods the writers used to find their way, such as drinking and engaging in open relationships. In his novel, The Tropic of Cancer, Henry Miller draws on his own experiences, weaving a semi-autobiographical tale just as famous for its observations on 1930s expatriate life as it is for its graphic descriptions of his main character’s sexual encounters.

How much of The Tropic of Cancer is factual is up for debate; Miller uses his own experiences and his friends and colleagues as inspiration while some names, dates, and events are entirely fictional. Many of the characters that the protagonist encounters are written as caricatures, making the book a social criticism as much as it is an erotic novel. Using stream-of-consciousness, Miller floats back and forth from the past to the present, making his story seem more like the musings of an impoverished writer frustrated at his situation in this course of his life.

The sexual encounters of Miller’s protagonist were so explicit that it was banned and censored in multiple countries, including the United States, Canada, the United Kingdom, and Finland. The United States Customs Service banned The Tropic of Cancer after its publication in France in 1934. In the early 1960s, when the American Publisher Grove Press published the novel, more than sixty plaintiffs in twenty-one states filed obscenity suits against retail booksellers. Since the United States Supreme Court ruled that The Tropic of Cancer did not have the characteristics of obscene literature in 1964, it has become one of the most important American novels of the twentieth century for what the New York Times considered the “free speech that we now take for granted in literature.”

The Story of O (1954)

When it comes to the most shocking erotic novels, The Story of O is usually at the top of everyone’s list. Playing out like a male dominance fantasy, a Parisian photographer’s lover René initiates her to the BDSM lifestyle by bringing her to a chateau, where a secret club trains her in the art of submission. When they arrive, to prove the strength of their connection, Rene tells O that he is giving her to his stepbrother as a sex slave.

Sir Stephen proves to be stricter than her lover, but that is the point: Rene wants to teach O how to be a submissive lover when there are no personal feelings involved. By summer, Sir Stephen has complete control over O, who sends her to a mansion of dominant female masters for further training. When O returns to Sir Stephen, he presents her to a party as a sex slave, and everyone at the party objectifies her in every possible way.

Written under the pen name Pauline Réage, French novelist Anne Desclos kept her identity a secret for about four decades; finally, before her death in 1998, she revealed that she had written The Story of O and why she had written it. While she was working for the French publisher Jean Paulham, who was also her boyfriend, he revealed that he was a fan of the Marquis de Sade. When he also told her that no woman could write like the eighteenth-century French nobleman, Desclos took the statement as a challenge, writing The Story of O as a love letter to Paulham.

The Story of O was a huge commercial success, winning the coveted Prix des Deux Magots literature prize in France in February 1955. The French courts brought obscenity charges against the author and the publisher. The charges were eventually thrown out, but the courts won the right to prevent the publisher and the unknown author from publicizing the book for many years. Many Feminists have heavily criticized the novel for its objectification and violence against women. A group of French feminists, Mouvement de liberation des femmes, publicly protested when a film based on the book was released, claiming that the book and the movie were offensive.

Lolita (1955)

The story of a literature professor who marries a woman to manipulate her preteen daughter into having a relationship with him, Vladimir Nabokov’s Lolita continues to be controversial over sixty years after its publication. Modern scholars have heavily criticized the novel for its use of hebephilia, a sexual attraction to prepubescent or early adolescent children, as an artistic motif and for reducing Lolita as an object of desire without any indication of her thoughts or feelings. Despite the criticism and the uncomfortable subject matter, Lolita has gained classic status, consistently included in “must-read” lists and topping multiple lists in best American literature.

Now that psychologists understand the mental impact of sexual abuse in childhood, Humbert’s manipulations of Lolita are especially troubling. Humbert consummates his lust for her by convincing her to demonstrate what she thinks qualifies as sexual activity. Bribing her for sexual favors, he threatens her that she will end up in an orphanage if she leaves him. Nabokov specifically references a case of child sexual abuse that inspired the novel. In 1948, fifty-year-old mechanic Frank Lasalle kidnapped and sexually assaulted eleven-year-old Florence Horner, posing as her father when they checked into hotels. Lasalle completely brainwashed Horner, threatening to send her to a juvenile facility if she didn’t comply.

“To a Dark Moses” (1973-1974)

Much like The Carnal Prayer Mat, the celebrated poet Lucille Clifton connects religious and erotic themes in her poem “To a Dark Moses,” making an important statement on the power of female sexuality. Using biblical imagery, Clifton represents herself as “the Burning Bush,” referenced in the Book of Exodus as the bush in flames on Mount Horeb, marking the location where God told Moses that he would lead the Israelites to Canaan. Clifton’s description of her lover, representing Moses from the biblical story, is graphic, using words such as “rod” and “serpent” to describe him.

Written in the midst of the feminist movement, a time when women’s sexual empowerment became part of the feminist rhetoric, Clifton uses the burning bush that was not destroyed on Mount Horeb as a metaphor for her sexuality. “To a Dark Moses” is a significant work of literature that celebrates women’s sexual power in general, stating that women do not need men to satisfy them, an idea that would become an essential component of sex-positive feminism that would emerge in the following decade.