10 Books Dirtier Than 50 Shades Of Grey

Over the years, countless books have caused outrage for their explicit depictions of sex and frank discussions of sexuality. For decades, novels were banned for featuring any mentions of "lewd conduct" at all. It may be hard to believe, but there was a time when even writing about sex between married couples was too taboo for many readers. Even recently, the kinky relationships between the characters in the best-selling Fifty Shades of Grey series have shocked many readers.

E.L James' book became a legitimate phenomenon shortly after being published in 2012. The novel was immediately controversial for its depiction of a BDSM relationship and sex life. Millions of readers flocked to the novel to see what all the fuss was about, and it has since been adapted into a soon-to-be blockbuster film.

The director and producers of the film have admitted that, in order to avoid an NC-17 rating, the film will not be as sexually charged as the source material. Many believe the novel is simply too racy for a wide release. However, some critics have noted that far more explicit works of literature were written before Fifty Shades of Grey.

Listed below are a handful of the books that are even dirtier than 50 Shades of Grey.

10 Portnoy's Complaint- Philip Roth


Like many of the authors on this list, Philip Roth is both critically well-regarded and infamously controversial. Also like many of the other writers on here, the author has been challenged countless times throughout his career for his use of thinly-veiled autobiographical elements. This use of Roth's life as a source of inspiration was never more scandalous than in Portnoy's Complaint.

Written from inside of the title character's mind, the novel shocked audiences in the 1960's with its frank, and frankly hilarious, descriptions of sexuality. One particularly controversial scene, which saw the book's "hero" find a very unusual (and unsanitary) use for raw liver, proved a step too far for even the most liberal critics. The novel was denounced as depraved filth, and was of course a massive success.

9 Tropic of Cancer- Henry Miller


Once again, another author on this list is accused of exploiting their real life for material. In fairness, Henry Miller made no secret of the fact that his book Tropic of Cancer was a partially autobiographical work. However, this was the least controversial element of the book.Throughout the novel, lengthy passages describe Miller's sex life in great, all-encompassing detail. The book dedicated entire paragraphs to climaxes, and pages to foreplay. As a result, Miller's masterpiece was banned and branded "obscene". This soon lead to a landmark court case centered around defining the limits of free speech in America. The novel was eventually published, and remains considered a classic of twentieth century literature.

8 Lady Chatterley's Lover- D.H Lawrence


D.H Lawrence's Lady Chatterley's Lover is a love story about an affair between the upper class Constance and her gamekeeper Oliver. Nowadays, the novel is viewed as an early classic of the modernist literature movement. At the time of its release, however, most readers were far more interested in the sex scenes and dirty language that they had heard the book was filled with. When the book was released, it was immediately branded "immoral" by English censors, and was banned for years in Canada, America and Japan as well. The book was one of the first to use four letter words and feature lengthy, explicit sex scenes. It was a combination that both horrified censors and delighted audiences.

7 Story of the Eye- Georges Bataille


Many of the books listed here were remarkable at the time of their writing for their explicit depictions of sex. However, in the last few decades, sex has become more widely and openly discussed. It takes a lot to shock the modern reader, and many once scandalous texts nowadays seem tame.

This is not true of Georges Bataille's Story of the Eye, at all. First published in 1928, the author and intellectual's short novella tracks the twisted relationship of two teenagers that ends in tragedy. Despite the innocent synopsis, the book is far from Romeo and Juliet. Bataille's work describes in nauseating detail some of the most bizarre depravity ever written, involving public nudity, murder, and a stomach-turning use for the titular eye.

6 Venus in Furs- Leopold von Sacher-Masoch


For many of our readers, Fifty Shades of Grey will be their only introduction to the kinky world of BDSM. But while Christian Grey keeps his lover on a short leash for much of the series, few books have featured male heroes dominated by their female love interests. Venus in Furs, written in 1870, was one of the earliest depictions of this still controversial topic. It tells the partially autobiographical story of a young man, who meets a young woman who begins a relationship with him, and eventually dominates both his personal life and his love life.

Like the Marquis de Sade, the author's name was used to refer to the phenomenon he documented in his writing after his death. Masochism, the enjoyment of having pain inflicted on oneself, is named after Leopold Von Sacher-Masoch.

5 Justine- Marquis de Sade


If it weren't for Fifty Shades of Grey, many readers would have never heard of BDSM (Bondage, Domination, Sadism and Masochism). However, without the work of the Marquis de Sade, sadism would not even exist.

The infamous writer gave his name to sadism, which describes the enjoyment of inflicting pain, when he wrote Justine. The book delights in the torturous sex life of its heroine, the long-suffering Justine. Even modern readers are both appalled and aroused in equal measure by the book's descriptions of depravity and debauchery.Even more shocking was the evidence that, in his real life, the troubled author may have enacted many of the disturbing acts featured in Justine.

4 Story of O- Anne Desclos


Like de Sade's Justine, Story of O blurs the line between reality and writing. The book's author stayed anonymous for years after its release, afraid to identify herself with the explicit, erotic text. The story of the novel has a few similarities with E.L James' bestseller, centered around a young woman who takes part in a submissive relationship with a powerful man. However, Story of O is made of significantly stronger stuff than the Fifty Shades series.

The heroine of the story is shared by countless men across the novel, as you read on you will discover that she enjoys the entire journey. The novel remains a shocking read over fifty years on, and many critics believe that Desclos makes a serious point about society's treatment of women through the story.

3 Myra Breckinridge- Gore Vidal


Gore Vidal was a highly respected intellectual when he authored Myra Breckinridge in 1968. He had written numerous novels and had also adapted acclaimed writers like Tennessee Williams for the screen. As a novelist and critic, he was set to become one of the defining voices of the post-war generation.

Myra Breckinridge was one of the most bizarre novels of the sixties. The plot initially revolves around a young woman looking to use kinky sex as a way to control the men around her. Things grow complicated when the heroine is revealed to be a man mid-way through gender-reassignment surgery. The plot only grows stranger from here, and the erotic mischief throughout the book leaves Fifty Shades of Grey seeming positively tame.

2 Couples- John Updike


American author John Updike was one of the first writers to introduce casual sex to highbrow literature. His novel Couples focuses on married swingers, a group both topical in the sixties and still shocking nowadays.

It seems that no amount of whips and chains will ever compete with the old-fashioned shock of stealing away another's lover. The book focuses on ten separate couples who sleep with each other, with the circle encompassing happy newlyweds and crumbling marriages. The internal lives of each couple are thoroughly explored. Their sex lives are also shown in close-up, in some incredibly raunchy excerpts which shocked America upon the book's release.

1 Ulysses- James Joyce


Nowadays, James Joyce's 1922 magnum opus Ulysses is best known for being one of the greatest- and most difficult- novels ever written. Charting a day in the life of its three main characters, the book was endlessly innovative and went on to redefine literature for the coming century. However, at the time of its release Ulysses was better known as one of the most controversial- and most explicit- books of its time. The book was so unbelievably shocking that it was banned before Joyce had even finished writing it.

Joyce wrote much of the novel as a look into the minds of Dublin couple Leopold and Molly Bloom. Both characters, however, have filthy minds, and their thoughts are both beautifully written and full of sex, adultery and all sorts of thoroughly adult material.

More in High Life