For the next four decades, Casanova devoted himself to the pursuit of pleasure and a lavish lifestyle. His working life, by contrast, was chaotic. He graduated from Padua University as a lawyer but felt an “unconquerable aversion” to the legal profession. Instead, he took holy orders. This started well. He landed a job working for a powerful cardinal in Rome, where he met the pope and persuaded him to allow him access to “forbidden books” and grant him special dispensation to eat meat on “fish only” days (on the grounds that fish “inflamed” his eyes). After being caught in a three-in-a-bed romp with two sisters and then arrested for gambling debts, he left the Church in a hurry, though a distinctly ecclesiastical flavor lingers on in the records of his romantic encounters (he “approaches the altar frieze,” “performs the gentle sacrifice,” and on one occasion “reaches the porch of the temple, without gaining free entrance to the sanctuary”). Casanova’s next temping job was as an officer in the Venetian army. Initially attracted by the smart uniforms, he almost immediately got bored with the repetitiveness of military life, so he had a stab at being a theater violinist, followed by trying his hand as secretary to a Venetian senator. And so it went on. Casanova’s charm and intelligence would get him work, after which he would be distracted by women, rack up huge gambling debts, and be forced to flee from his creditors. His story reads like half a dozen airport thrillers with the pages shuffled and put back together in the wrong order. He was a diplomat, mathematician, spy, alchemist, Freemason, card sharp, magician, entrepreneur, faith healer, actor, playwright, duelist, lawyer, physician, and finally, librarian. Fluent in Italian, French, Latin, and Greek, with a smattering of German, English, and Russian, he traveled some forty thousand miles and negotiated his way in twenty-seven different currencies. Work, for Casanova, was only about status: He would do anything for anyone, in any country, as long as it allowed him freedom and the semblance of wealth and influence. Throughout his life, most of his “income” came from gifts. When he needed serious money, he gambled:

Why did I gamble when I felt the losses so keenly? What made me gamble was avarice. I loved to spend, and my heart bled when I could not do it with money won at cards.

And he was good. Over the period covered by his memoirs, his winnings came to more than $11.7 million in modern terms, with his losses running at less than a million. The low boredom threshold he exhibited when trying to hold down a job never affected him at the card table. One marathon session of piquet lasted for forty-two hours without a break.

But gambling, however addictive he found it, was always a means to an end—and the end, with Casanova, was always a woman. “Love is three quarters curiosity,” he wrote—and his was insatiable: any woman, under any circumstance, was fair game. Tall and skinny with a beaked nose, bulbous eyes, and heavy eyebrows, he was not classically handsome, but it was his unshakable conviction that he—or indeed any man—could seduce any woman if she felt herself the sole object of his undivided attention. “I don’t conquer, I submit,” he explained. Women trusted him and he was an appreciative and considerate lover. He liked to give them pleasure and even practiced safe sex, using a variety of condoms made from sheeps’ intestines and linen or—if all else failed—half a lemon inserted as a kind of improvised diaphragm. His list of conquests is surprisingly modest given his reputation: He slept with perhaps no more than 140 women (a total trounced by Byron, when he lived in Venice, in just two years). On the other hand, it was enough to give him gonorrhea at least eleven times, and when he died in 1798, it was from a bladder complaint probably caused by repeated venereal infections.

The detail and humor of Casanova’s memoirs make for a compelling read. He relates that he lost his virginity to two sisters and that their lovemaking was punctuated by an impromptu dinner of bread and cheese. Falling for a castrato singer called Bellino, and convinced she was a woman in disguise, he groped her crotch, only to find an unmistakable bulge. Indefatigable as ever, he reasoned this must be a “monstrous clitoris,” and his persistence paid off. “Bellino” was indeed a woman called Teresa, who wore a false phallus to get around the papal ban on women singing in church choirs. Needless to say, she became his mistress. In Venice, he enjoyed a menage a trois with the French ambassador and a nun. He nearly seduced a beautiful young woman who turned out to be his own daughter by a former lover. A few years later, they met again and this time he deliberately seduced her and slept with her and her mother simultaneously. Untroubled by shame, he also bedded his niece, encouraged a twelve-year-old novice nun to fellate him through a grill, and seduced all five daughters from one family in exchange for rescuing their parents from ruin. But he didn’t get it all his own way. In London a courtesan called Marianne Charpillon refused to go to bed with him and then stole all his money. He was so upset by this that he decided to kill himself by jumping into the Thames, and only stopped when a friend persuaded him to go to a pub and get drunk instead. To get revenge, he trained a parrot to recite: “Miss Charpillon is more of a whore than her mother.” This so enraged Miss Charpillon that she took legal advice on whether she could sue a parrot for libel.

Casanova had better luck with the Marquise d’Urfe, one of the richest women in Paris, who was impressed by his deep knowledge of the Kabbalah. He convinced her that he could help her be reincarnated and that part of the necessary ritual involved his having sex with her. The Marquise was so physically repulsive he had to fake two of his three orgasms. This wasn’t his usual problem—he was afflicted by premature ejaculation through most of his life— although he claimed he could make love at least six times a night with the help of a special concoction of chocolate and egg white. He also fixed the oyster’s reputation as an aphrodisiac, sometimes eating fifty for breakfast, declaring that the best sauce for an oyster was his lover’s saliva. A special treat was eating live bivalves off a girlfriend’s breasts.

In 1755 Casanova’s sexual intrigues, combined with his dabbling in banned Masonic rites and magic, earned him a five-year sentence in Venice’s Piombi prison. He stuck it out for nine months before escaping by breaking through the roof of his cell and walking out of the main gates when they were opened the next morning. Forced to seek exile in France, he came up with his greatest and most lucrative financial scam—inventing the French national lottery. Now in his midthirties, he enjoyed a brief spate of wealth and fame, styling himself the Chevalier de Seingalt (an entirely bogus title). He met—and was disappointed by—Voltaire, arguing with him over religion; he discussed powered flight with Benjamin Franklin and taxation policy with Frederick the Great; and made friends with Lorenzo Da Ponte, Mozart’s favorite librettist. (It seems likely that Da Ponte’s masterpiece, Don Giovanni, was based at least in some part on Casanova, who may even have contributed to the writing himself.)

Casanova’s own literary ambitions never quite came together until the very end of his life. He wrote forty-two books, including a history of Venetian government, a history of Poland, and a much-admired translation of Homer’s Iliad into modern Italian. He even produced a five-volume science-fiction novel, Isocameron, which predicted the motor car, the airplane, television, and many other inventions. His plays were performed across Europe but he was never in one place long enough to capitalize on his reputation. Fame, money, and love all had a way of deserting him. He never came close to getting married, although he did, in his late twenties, fall heavily for a young Frenchwoman called Henriette:

They who believe that a woman is incapable of making a man equally happy all the twenty-four hours of the day have never known an Henriette. The joy which flooded my soul was far greater when I conversed with her during the day than when I held her in my arms at night.

Henriette was smart and cultured as well as beautiful, and she seemed to sense Casanova was in the grip of a pathology he couldn’t control. She turned the tables on him, and stole away in the night, having scratched a message on his bedroom window with her diamond ring. It said, “You will forget Henriette, too.” She also slipped 500 gold louis into his jacket pocket (worth about $45,000 today): the perfect “thanks, but no thanks” gesture. She had his number: clever, charming, and expensive to run. Casanova was bereft and cheered himself up the only way he knew how: more travel, more women, and more gambling. It would be easy to argue that he squandered his talents and that but for his addiction to sex, he might have ended up, in some way, as one of the great men of his day. Surveying the wreckage at the end of his life, he fantasized about the different course he might have taken:

If I had married a woman intelligent enough to guide me, to rule me without my feeling that I was ruled, I should have taken good care of my money, I should have had children, and I should not be, as now I am, alone in the world and possessing nothing.

Anyone familiar with his effervescent memoirs will see this as self-pitying, self-indulgent humbug: Casanova

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