The Most Perverse Sexual Rituals of the Roman Empress

Rome, 48 AD. The imperial palace, a gilded cage of power and deceit, lay silent beneath a moonless sky. Yet, while Emperor Claudius slept in his private chambers, oblivious to all that surrounded him, a woman moved with careful urgency along a secret corridor, each step betraying her rank.

She wore a coarse, cheap blonde wig meant to conceal the dark, nocturnal sheen of her natural hair. Her attire was that of a streetwalker: worn fabrics, no glittering jewelry, and none of the subtle cosmetics that distinguished a noblewoman; only the faint, earthy scent of Rome’s harsh streets clung to her dress. She moved swiftly, like a shadow through Rome’s twisting alleyways, keeping her face carefully hidden in the darkness. Her destination was the Subura district, the corrupt heart of the city, a filthy labyrinth where criminals hid, the poor struggled to survive, and cheap brothels glowed with a dirty light.

When she pushed open the heavy, creaking door of one of those houses, she stepped into the warm, perfumed air of vice. The madam, a hardened witness to Rome’s darkest nights, recognized her immediately, for the disguise was thin to those who truly knew her. There, she wasn’t called by her noble name but by another: Lyscisca, the she-wolf. This woman, who moved through the deepest corruption of Rome to sell herself to the lowest class, was none other than Valeria Messalina, Empress of Rome, the most powerful woman in the known world, and she was about to commit an act that would resonate throughout history.

Before delving deeper into that infamous night, it’s essential to understand who Messalina truly was and how she became the most scandalous figure in Roman history. She was born around 20 AD into one of Rome’s oldest and most respected families. Her lineage, woven with power, connected her directly to Augustus, Rome’s first emperor. This was more than just an aristocratic life; by Roman standards, she was true royalty. Fortune had bestowed upon her everything: immense wealth, extraordinary beauty, an untouchable social position, and an education befitting her noble birth. Ancient writers described her pale, luminous skin, hair like spun gold, and aristocratic features that set her apart from even the most beautiful women in Rome.

At around 17, she was married to Claudius, a man more than 30 years her senior. At that time, Claudius was far from the imperial throne; in fact, he was widely seen as a mockery by the Roman elite. He walked with a limp, spoke with a stutter, and sometimes drooled, leading many to believe he was weak or slow-witted. Even so, he had impeccable lineage, just like Messalina. Their marriage was a carefully arranged political alliance to unite two important branches of the imperial family. Then, in 41 AD, it all fell apart, and their lives were forever changed.

Emperor Caligula, the cruel ruler whose brief reign had filled Rome with fear, was assassinated by his own Praetorian Guard. He had descended into madness: he called himself a god, committed public infidelities with his sisters, even appointed his horse consul, and killed people for his own pleasure. The Praetorian Guard, whose duty it was to protect the emperor, finally had enough and killed him in a hidden corridor of the palace. Rome was suddenly left without a ruler, creating a dangerous power vacuum. The guards knew they had to act quickly before the Senate or rival armies could seize control.

Their search led them through the palace, where they found Claudius, Caligula’s uncle, hiding behind a curtain and trembling with fear. Instead of killing him, they brought him out and declared him emperor. It was almost a cruel joke, since Claudius had never been destined to rule. His own family had ridiculed him all his life for his illnesses and clumsy behavior, but the guards needed someone of imperial blood, and Claudius was the last living adult male descendant of Augustus, so he became emperor.

In a single instant, Messalina’s clumsy, stammering husband became the most powerful man in the world. She, at only about 21 years old, became the Empress of Rome. Overnight, she transformed from the wife of an obscure relative into the foremost woman of the vast Roman Empire. She now possessed boundless wealth, thousands of slaves, palaces, gardens, jewels, fine clothes, and the most exquisite foods. She had the power to grant favors, elevate families, destroy enemies, and, most importantly, she had given birth to Britannicus, Claudius’s true heir; one day her son would rule Rome, giving her unparalleled influence. Most women with such power and security would have been content knowing their children’s future was safe, but for Messalina, even that was far from enough.

The great Roman historians, including Tacitus, Suetonius, Pliny the Elder, and Juvenal, all wrote about Messalina, and what they recorded was nothing short of astonishing. According to the chilling accounts of ancient historians, Messalina possessed an insatiable sexual appetite, which she satisfied with relentless energy and, at times, in a scandalous manner, even in full public view. Her actions went far beyond mere love affairs, which, on their own, would have caused a huge scandal. She transformed her sexuality into a tool of power and intimidation. She selected the men who caught her eye—often married, frequently of considerable political influence—and set about seducing them. But these encounters were never romantic; they were acts of coercion. Rejecting the empress’s advances could bring catastrophe: a man could find himself falsely accused of serious crimes, stripped of his rank, or, most feared, face an untimely death as a consequence. Very few dared to refuse; they simply couldn’t. The Empress desired them, and a simple “no” could not become a death sentence.

Her targets were varied: powerful military commanders, prominent senators, and even actors and artists, which was especially scandalous since actors were considered socially inferior, barely above slaves. One of her most infamous lovers was an actor named Nestor. Her obsession with him grew so intense that when he tried to resist, she went directly to Emperor Claudius. She demanded that Claudius issue a decree forcing Nestor to obey the empress in all matters. Claudius, seemingly unaware of the nature of their relationship, astonishingly complied. Thus, Nestor was legally bound by imperial decree to sleep with the empress—a shocking absurdity. However, Messalina’s desires, as recorded by Juvenal, extended far beyond encounters with influential or attractive men. She led a secret life so incredible that few could truly comprehend it.

Juvenal describes how she would wait until Claudius fell asleep, disguise herself, and secretly slip out of the palace. Her destination was the Subura, Rome’s infamous red-light district. There, she worked in a brothel under the name Lyscisca, the she-wolf. Consider the audacity and the implications: the Empress of Rome, the highest-ranking woman in the civilized world, willingly working as a common prostitute in the city’s most dangerous and sordid quarter. Juvenal describes her standing in the doorway of her cubicle in the brothel, her breasts adorned with gold, luring men inside. She worked tirelessly throughout the night, attending to one client after another. Even when the brothel closed at dawn and she returned to the palace, her desires remained insatiable; dragging her exhausted body back to the imperial palace, she still craved more.

Naturally, one might think this sounds too outrageous to be true, and skepticism is understandable. Juvenal was a satirist whose writings often exaggerated to criticize Roman society. However, the important point is that multiple ancient sources recount similar stories, and one particular tale, both shocking and consistent, appears repeatedly in the historical record. This is the story of the ultimate sexual competition. The account is preserved thanks to Pliny the Elder, a respected Roman scholar and naturalist who documented facts rather than created fiction. Pliny relates that Messalina, driven by a peculiar ambition, sought to definitively answer one question: who possessed greater sexual stamina, an empress or a professional prostitute? She dared to challenge Scylla, one of Rome’s most famous courtesans, to a direct confrontation.

The rules were simple: each woman would have sex with as many men as she could in a continuous 24-hour period. The winner would be the one who had sex with the most men. This audacious event was not a secret; it was openly witnessed by members of the Roman nobility. Messalina organized it as a public spectacle, a perverse form of entertainment for the elite. The contest began. Scylla, a seasoned professional and aware of the importance of pacing herself, worked steadily throughout the night. By dawn, she had had sex with 25 men. It was an impressive feat of endurance; she was completely exhausted and could not continue. Messalina, however, pressed on. She did not stop at 25; she continued beyond 30 according to some sources, perhaps even more. She only stopped when there were literally no men left willing to participate; all those present had reached their limit. Messalina had won. The empress had defeated a professional prostitute in a sex marathon before a demanding audience of Roman nobles. Pliny records this as a fact in his Natural History, presenting it within a discussion about human versus animal sexual behavior, almost as an objective observation.

Pliny writes: “Messalina, wife of Claudius Caesar, considering this a prize worthy of an empress, selected one of the most notorious women of the prostitution profession to test herself and overcame her after 25 continuous embraces day and night.” He desperately begged Messalina to end his own life before the executioners arrived, offering her one last chance to preserve his dignity and avoid public humiliation or the brutal torment of an official execution. In Roman culture, choosing suicide in the face of inevitable death was considered an honorable act, a way to maintain at least some degree of control over one’s fate.

However, in that final moment, Messalina could not carry it out. She held a dagger in trembling hands, repeatedly pressing the cold steel against her throat, but her courage failed her at the last moment. She could not force herself to plunge the blade in, even knowing with absolute certainty that her future was over. She clung to life and thus waited. The soldiers arrived, led by a tribune of the Praetorian Guard carrying Claudius’s direct and implacable orders. They found her in the palace gardens, huddled beside her mother. There was no trial, no opportunity to defend herself, no chance to make a final plea to Claudius.

The tribune drew his sword, its cold steel heralding the end. Domitia Lepida held her daughter tightly, cradling her as the blade descended. Messalina died there, in the once-beautiful gardens, stabbed before her mother, her blood staining the marble pathways she had walked as empress. She was probably around 28 years old, having wielded the power of empress for only seven years. In that brief, turbulent period, she had become the most infamous woman in Rome, her name whispered in scandal throughout the city. Her son, Britannicus, Claudius’s heir, was only seven when his mother was executed. He never truly recovered from the trauma.

Claudius remarried quickly and pragmatically, taking Agrippina the Younger as his new wife. Ambitious and shrewd, Agrippina introduced her own son Nero into the imperial family and immediately began to undermine Britannicus. She tirelessly promoted Nero as Claudius’s legitimate heir. When Claudius died under suspicious circumstances, Nero ascended the throne. Shortly afterward, Britannicus died suddenly at a dinner party; most historians agree that Nero poisoned him. Messalina’s daughter, Octavia, was forced to marry Nero and suffered extreme cruelty; he later divorced her on fabricated charges of adultery and had her executed. Both of Messalina’s sons died young, violently and tragically, victims of the same political games their mother had played.

However, Messalina herself was not forgotten. She transcended mortality and became a legend. For two millennia, writers and artists have been fascinated by Messalina’s story. Poets composed verses in her name, painters depicted her scandalous life, sculptors carved her image in marble, and playwrights created dramatic works centered on her existence. During the Renaissance, she became a symbol of female sexual excess, a warning against unbridled lust. In the Victorian era, her story was used for moral purposes, cautioning against the dangers of uncontrolled female sexuality. In the 20th century, she reappeared in films and novels, always as the ultimate femme fatale, a woman whose appetites seemed insatiable.

Iconic depictions often show her in the notorious brothel, either standing provocatively in the doorway inviting clients or lying exhausted after her legendary contest with Scylla. These images became iconic motifs in Western art, shaping the social perception of female sexuality, power, and Rome itself. However, the story takes a more complex turn. Modern historians are increasingly re-examining what we thought we knew about Messalina. They critically analyze ancient sources, realizing that almost all accounts were written by her enemies or by historians who never met her personally, relying on often biased secondhand reports.

Patterns emerge in the charges against her: accusations of promiscuity, poisoning rivals, and manipulating her husband were the same calumnies routinely leveled at powerful Roman women who challenged patriarchal authority. Today, historians see that Messalina was, in fact, a shrewd and effective political operator. She influenced appointments to high office, managed extensive patronage networks, and strategically placed allies in positions of power. In essence, she used the tools of governance just as the emperors did. Yet, because she was a woman, her legitimate political maneuvers were constantly reinterpreted as sexual manipulation and scandal.

Even the famous story of her contest with 25 men could be entirely fabricated. Pliny the Elder, who recounted it, wasn’t in Rome during Messalina’s lifetime; he was a young student in northern Italy. He couldn’t have witnessed the event firsthand; he was simply repeating rumors and sensationalized accounts that circulated years after her death. Juvenal, the poet who described her exploits in the brothel, was writing satire decades later, deliberately exaggerating to criticize the supposed moral decay of Roman society.

The story of Messalina working in a brothel under a false name could also have been entirely fabricated by her enemies, deliberately constructed to utterly humiliate her memory. After all, in ancient Rome, if someone wished to destroy a woman’s reputation beyond repair, accusing her of prostitution was the most devastating tactic imaginable. But what if Messalina was nothing more than a young woman thrust into the dizzying and treacherous role of empress before she was truly ready? What if she was simply attempting to exert authority through the only avenues available in a male-dominated society? What if her ultimate downfall was the result of a single fatal political misstep when she naively allied herself with Silius?

Perhaps the scandalous sexual rumors are grotesque exaggerations or even outright fabrications intended retroactively to justify her execution and erase her from official records. Or perhaps some fragment of truth exists; perhaps she really did have numerous affairs, perhaps she really did use sex as a tool of influence and control. Perhaps she was genuinely extraordinary in her sexual activity by the standards of her time or even by ours. The uncomfortable truth is that we will probably never know for sure. The real Messalina has been lost in the turbulent mists of history, her authentic self obscured by centuries of myth, legend, and deliberate accusations.

What remains are the stories, the enduring legends, and the chilling claims. Regardless of their veracity, these accounts have profoundly influenced Western culture for 2,000 years. They have shaped our perception of female sexuality and power, provided endless inspiration for artists and writers, and become a permanent and undeniable part of the mythology of Rome itself. Whether the accounts are accurate or not, Messalina evolved into a symbol: a symbol of unbridled female sexuality, a symbol of how absolute power can utterly corrupt, a symbol of the decadent excesses of imperial Rome.

Her very name became synonymous with promiscuity for centuries. Calling a woman Messalina was one of the most damning insults imaginable. Yet there is a deeper layer to consider. Even if some of these scandalous accounts were true, even if she really did sleep with dozens or hundreds of men, what does that ultimately tell us? It illustrates a society in which women possessed almost no legitimate agency except through the often dangerous conduit of their sexuality. It reveals a culture so obsessed with controlling female desire that any woman who appeared to enjoy sex or use it for her own ends was instantly labeled deviant, monstrous, and dangerous. It forces us to confront how history is written by the powerful and how women’s narratives are frequently distorted to serve political agendas.

Messalina lived in a world where the title of empress granted immense privileges but offered very little real authority. She couldn’t enact laws, command armies, or fully control her vast estates. So what real power did she have? Could she influence her emperor husband? Yes. Could she carefully cultivate networks of loyalty and wield the powerful and dangerous influence of her own sexuality? Yes. If she used that power to extremes, and if the stories about her are even partially true, should we really be surprised? She was a young woman violently thrust into a dangerous and exposed position, surrounded by men constantly scheming for more power, desperately trying to survive and thrive in a system designed against her from the start.

When she overstepped the bounds, believing she could marry Silius and evade the consequences, the system reacted. It crushed her swiftly and brutally and then attempted to erase her from history altogether, demonizing her memory. The story of Messalina and the 25 men has survived for 2,000 years. It has been retold and embellished countless times, inspiring enduring art, literature, grand operas, and captivating films. It remains one of the most infamous and scandalous narratives of ancient Rome. Yet perhaps the true story isn’t about sex at all.

Perhaps at its core, it’s about the power of a young woman trying to carve out influence in a society that denied her legitimate avenues to do so; about the men around her, threatened by her growing power, who systematically destroyed her and manipulated her memory, turning her into a monstrous symbol of insatiable lust. Perhaps the real scandal isn’t what Messalina did or didn’t do in that brothel; perhaps the real scandal is how history treated her, how her complex story was twisted, weaponized, and manipulated, how it was transformed into a warning to intimidate women for centuries. We will never truly know the real Messalina; the historical record is too tainted, too politicized, too distant. But her legend survives, and that legend—whether based on fact, fiction, or a mixture of both—reveals something profoundly significant about Rome, about power, about human sexuality, and about the deceptive ways in which history chooses to remember the past.