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A young lad cries out while his skull is forcefully held, a massive digit digging into his cheek as his parent's mighty hand holds him by the throat. That moment from The Sacrifice of Isaac visits the Uffizi Gallery, evoking unease through Caravaggio's harrowing rendition of the suffering child from the biblical narrative. The painting appears as if Abraham, commanded by the Divine to kill his offspring, could break his spinal column with a single turn. Yet the father's chosen approach involves the silvery steel knife he grips in his remaining hand, prepared to slit the boy's throat. A definite aspect remains – whoever modeled as the sacrifice for this breathtaking work displayed remarkable acting skill. Within exists not just fear, shock and begging in his shadowed eyes but also profound grief that a protector could betray him so completely.

He took a well-known scriptural tale and made it so fresh and raw that its terrors seemed to happen directly in view of you

Viewing in front of the painting, viewers identify this as a actual countenance, an accurate record of a young subject, because the identical youth – recognizable by his disheveled hair and nearly black eyes – appears in two additional paintings by Caravaggio. In every instance, that richly emotional face commands the composition. In John the Baptist, he peers playfully from the darkness while embracing a lamb. In Victorious Cupid, he smirks with a toughness acquired on Rome's streets, his black feathery wings demonic, a unclothed adolescent creating chaos in a well-to-do residence.

Victorious Cupid, currently displayed at a London gallery, constitutes one of the most embarrassing masterpieces ever painted. Observers feel completely unsettled gazing at it. The god of love, whose arrows inspire people with frequently agonizing longing, is portrayed as a very tangible, brightly illuminated unclothed form, straddling overturned objects that include stringed devices, a music score, plate armor and an architect's ruler. This pile of possessions echoes, intentionally, the mathematical and construction equipment scattered across the floor in Albrecht Dürer's engraving Melencolia I – except here, the melancholic disorder is caused by this smirking deity and the turmoil he can unleash.

"Affection looks not with the vision, but with the soul, / And therefore is feathered Cupid painted blind," wrote the Bard, shortly before this work was produced around 1601. But the painter's Cupid is not unseeing. He stares directly at you. That face – sardonic and rosy-faced, looking with bold assurance as he struts unclothed – is the identical one that shrieks in terror in The Sacrifice of Isaac.

When Michelangelo Merisi da Caravaggio created his multiple portrayals of the same distinctive-looking kid in the Eternal City at the dawn of the seventeenth century, he was the highly acclaimed religious artist in a city enflamed by religious renewal. The Sacrifice of Isaac demonstrates why he was commissioned to decorate churches: he could adopt a scriptural story that had been depicted numerous times previously and render it so fresh, so raw and visceral that the terror seemed to be happening immediately in front of you.

However there existed another aspect to Caravaggio, evident as quickly as he came in Rome in the winter that concluded 1592, as a artist in his early twenties with no mentor or patron in the city, only skill and audacity. Most of the works with which he captured the sacred metropolis's eye were anything but holy. That could be the absolute first hangs in London's National Gallery. A youth parts his crimson mouth in a yell of pain: while stretching out his filthy digits for a cherry, he has instead been attacked. Boy Bitten By a Lizard is eroticism amid squalor: viewers can discern the painter's dismal chamber reflected in the murky liquid of the transparent container.

The boy wears a pink flower in his coiffure – a emblem of the sex trade in early modern painting. Venetian artists such as Tiziano and Palma Vecchio portrayed prostitutes grasping flowers and, in a painting lost in the WWII but known through images, Caravaggio represented a renowned female prostitute, clutching a bouquet to her bosom. The message of all these botanical signifiers is obvious: sex for sale.

How are we to interpret of Caravaggio's erotic portrayals of youths – and of one adolescent in specific? It is a inquiry that has divided his commentators ever since he achieved widespread recognition in the 1980s. The complex past reality is that the artist was not the homosexual hero that, for example, the filmmaker put on screen in his 1986 movie about the artist, nor so entirely pious that, as some artistic historians improbably assert, his Youth Holding Fruit is actually a portrait of Christ.

His early paintings indeed offer overt erotic implications, or even propositions. It's as if the painter, then a destitute youthful artist, aligned with the city's sex workers, offering himself to survive. In the Florentine gallery, with this thought in mind, observers might turn to an additional early work, the 1596 masterpiece the god of wine, in which the god of alcohol stares coolly at you as he starts to untie the dark ribbon of his robe.

A few years following the wine deity, what could have driven Caravaggio to paint Amor Vincit Omnia for the artistic patron Vincenzo Giustiniani, when he was finally growing almost established with important church projects? This profane non-Christian deity resurrects the erotic challenges of his initial paintings but in a more powerful, uneasy manner. Half a century afterwards, its hidden meaning seemed obvious: it was a portrait of the painter's lover. A English visitor viewed Victorious Cupid in about the mid-seventeenth century and was told its subject has "the body & face of [Caravaggio's|his] own youth or servant that laid with him". The name of this adolescent was Francesco.

The painter had been dead for about 40 years when this account was recorded.