The emperors of Rome could be wise, just and kind. They could also be vindictive, cruel and insane. And most of all, they could be the worst perverts the world has ever seen — at least according to ancient historians like Suetonius, Pliny, and Cassius Dio. Here are nearly a dozen of the most immoral, disgusting behaviors the rulers of the ancient world indulged in... supposedly. Chances are most of these were rumors made up by political enemies or gossiping plebs. But hey, just because they may not be true doesn't mean they're aren't still entertainingly perverse.
The Emperor Claudius married his brother's daughter Agrippina (his brother being long dead, thank goodness). "[H]is affections were ensnared by the wiles of Agrippina, daughter of his brother Germanicus, aided by the right of exchanging kisses and the opportunities for endearments offered by their relationship; and at the next meeting of the senate he induced some of the members to propose that he be compelled to marry Agrippina, on the ground that it was for the interest of the State; also that others be allowed to contract similar marriages, which up to that time had been regarded as incestuous." Yes, Claudius didn't just make niece-marrying legal, he made it patriotic!
2) Hiring Anal Sex Experts
No judgments on anal sex here, but putting professional anal sex experts on the imperial payroll is a bit much. "On retiring to Capri [Tiberius] devised a pleasance for his secret orgies: teams of wantons of both sexes, selected as experts in deviant intercourse and dubbed analists, copulated before him in triple unions to excite his flagging passions." In case these pros were somehow not up to the tasks Tiberius put them too, he had a sex library full of illustrated works so he could just point to what he wanted.
3) The Animal Game
Nero was so into being as depraved as possible — he supposedly defiled every single part of his body — that he had to think up some pretty original ways to keep it fresh. "[H]e at last devised a kind of game, in which, covered with the skin of some wild animal, he was let loose from a cage and attacked the private parts of men and women, who were bound to stakes, and when he had sated his mad lust, was dispatched by his freedman Doryphorus."
Say what you want about Caligula, but he was really, really good at incest. "He lived in habitual incest with all his sisters, and at a large banquet he placed each of them in turn below him, while his wife reclined above." His sister Drusilla was his favorite, having had sex with her when he was but a boy, and when they were grown, he simply took her from her legal husband for more fun. His other sisters, he was somewhat less fond of, and thus he only often prostituted them. So he wasn't just a sister-fucker, but a sister-pimp. Fun!
5) Sex Rest Stops
Here's an idea you've probably never had to make those long road trips more enjoyable: Set up stops full of prostitutes along your way! And when you do, thank Nero. "Whenever he drifted down the Tiber to Ostia, or sailed about the Gulf of Baiae, booths were set up at intervals along the banks and shores, fitted out for debauchery, while bartering matrons played the part of inn-keepers and from every hand solicited him to come ashore." Better than vending machines, that's for sure.
In terms of sexual depravity, Nero even put Caligula to shame by going to the source (so to speak) and having sex with his own mother Agrippina. How did people know? "[S]o they say, whenever he [Nero] rode in a litter with his mother, he had incestuous relations with her, which were betrayed by the stains on his clothing." Later, when Nero was Emperor, people tried to keep him from fucking his mother, mostly because they were afraid that would Agrippina would get too much power from the relationship. It should probably go without saying that eventually Nero tried to murder his mother by putting her on break-apart boat, right?
7) Creating an Imperial Brothel
Caligula was fond of spending money, but not so good at making it. After depleting the coffers at one point, he had the bright idea to turn the palace into an impromptu whorehouse. "To leave no kind of plunder untried, he opened a brothel in his palace, setting apart a number of rooms and furnishing them to suit the grandeur of the place, where matrons and freeborn youths should stand exposed. Then he sent his pages about the fora and basilicas, to invite young men and old to enjoy themselves, lending money on interest to those who came and having clerks openly take down their names, as contributors to Caesar's revenues." Rest assured, those who enjoyed themselves on credit eventually paid up, one way or another.
8) Part-Time Prostitution
The Emperor Elagabalus, who ruled from 203-222 AD, outdid Caligula in this regard: Elagabagus set up a brothel in the palace… and pimped himself. "Finally, he set aside a room in the palace and there committed his indecencies, always standing nude at the door of the room, as the harlots do, and shaking the curtain which hung from gold rings, while in a soft and melting voice he solicited the passers-by. There were, of course, men who had been specially instructed to play their part. For, as in other matters, so in this business, too, he had numerous agents who sought out those who could best please him by their foulness. He would collect money from his patrons and give himself airs over his gains; he would also dispute with his associates in this shameful occupation, claiming that he had more lovers than they and took in more money." If only all politicians were so... flexible when it came to balancing the budget.
9) Making a Man His Wife
I'm not talking about gay marriage here, at least not really. I'm talking about Nero taking a man and "making him a woman" in the worst way possible: "He castrated the boy Sporus and actually tried to make a woman of him; and he married him with all the usual ceremonies, including a dowry and a bridal veil, took him to his house attended by a great throng, and treated him as his wife." Eunuchs — when having sex with men and women just isn't enough any more.
Emperor Tiberius loved to swim, and he apparently also loved being pleasured by children. In a feat of inspiration, he managed to combine both these hobbies into one: "he trained little boys (whom he termed tiddlers) to crawl between his thighs when he went swimming and tease him with their licks and nibbles." It's like the world's most perverted aquarium!
I'm sorry, did you think Tiberius' "Tiddlers" were bad? He also used to get blowjobs from babies. "Unweaned babies he would put to his organ as though to the breast, being by both nature and age rather fond of this form of satisfaction." AAAUUGH.
Dishonorable Mention: Messalina
While not technically an Emperor, as wife of Claudius Messalina was an Empress, and she has the honor of having one of the earliest gangbangs in record history. And it was a contest, too! "Messalina, the wife of Claudius Cæsar, thinking this a palm quite worthy of an empress, selected, for the purpose of deciding the question, one of the most notorious of the women who followed the profession of a hired prostitute; and the empress outdid her, after continuous intercourse, night and day, at the twenty-fifth embrace." Needless to say, when Claudius found out he was so depressed he ended up marrying his niece. Oh, and had Messalina killed, obviously.