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The youthful boy screams as his head is firmly gripped, a large digit digging into his cheek as his father's mighty palm holds him by the neck. This moment from The Sacrifice of Isaac visits the Uffizi Gallery, creating distress through the artist's harrowing rendition of the tormented child from the scriptural account. It appears as if the patriarch, instructed by God to sacrifice his offspring, could break his spinal column with a solitary turn. However Abraham's preferred approach involves the silvery steel knife he grips in his remaining palm, prepared to slit Isaac's throat. A certain element stands out – whomever modeled as the sacrifice for this astonishing work demonstrated remarkable acting skill. There exists not just dread, surprise and begging in his shadowed eyes but also profound grief that a guardian could betray him so utterly.

He took a well-known biblical story and transformed it so vibrant and raw that its horrors appeared to unfold right in front of you

Viewing in front of the artwork, viewers recognize this as a actual countenance, an precise record of a young subject, because the same youth – identifiable by his tousled hair and almost dark eyes – features in several additional paintings by Caravaggio. In each instance, that richly emotional face commands the scene. In John the Baptist, he gazes mischievously from the shadows while holding a lamb. In Victorious Cupid, he smirks with a hardness learned on Rome's streets, his dark feathery wings sinister, a naked child running chaos in a well-to-do dwelling.

Victorious Cupid, presently exhibited at a London gallery, constitutes one of the most embarrassing masterpieces ever painted. Viewers feel totally disoriented gazing at it. The god of love, whose darts inspire people with frequently painful longing, is shown as a very tangible, vividly lit unclothed form, straddling toppled-over objects that comprise stringed instruments, a music score, metal armor and an architect's T-square. This heap of possessions echoes, intentionally, the mathematical and architectural gear strewn across the ground in Albrecht Dürer's engraving Melencolia I – except in this case, the gloomy disorder is caused by this grinning deity and the turmoil he can unleash.

"Love looks not with the eyes, but with the mind, / And thus is feathered Cupid painted sightless," penned Shakespeare, shortly prior to this painting was created around 1601. But the painter's god is not unseeing. He gazes directly at the observer. That face – sardonic and ruddy-cheeked, staring with brazen assurance as he struts naked – is the same one that shrieks in fear in The Sacrifice of Isaac.

As Michelangelo Merisi da Caravaggio painted his multiple images of the identical distinctive-appearing kid in the Eternal City at the dawn of the seventeenth century, he was the most acclaimed sacred painter in a metropolis ignited by religious revival. The Sacrifice of Isaac reveals why he was commissioned to decorate churches: he could take a scriptural story that had been depicted many times previously and render it so new, so raw and physical that the horror seemed to be occurring directly before the spectator.

However there existed a different aspect to the artist, apparent as quickly as he arrived in Rome in the winter that ended the sixteenth century, as a painter in his early twenties with no mentor or patron in the city, only talent and boldness. The majority of the works with which he caught the holy city's eye were everything but devout. What could be the very earliest hangs in London's National Gallery. A young man opens his red mouth in a scream of agony: while reaching out his filthy fingers for a cherry, he has instead been attacked. Boy Bitten By a Lizard is eroticism amid poverty: observers can discern Caravaggio's dismal chamber mirrored in the murky liquid of the transparent container.

The boy sports a rose-colored flower in his hair – a emblem of the sex trade in Renaissance art. Venetian artists such as Tiziano and Jacopo Palma portrayed prostitutes holding flowers and, in a painting lost in the second world war but documented through photographs, the master portrayed a famous woman courtesan, holding a bouquet to her bosom. The meaning of all these floral signifiers is clear: sex for sale.

How are we to interpret of Caravaggio's erotic portrayals of youths – and of one boy in particular? It is a question that has split his interpreters ever since he achieved mega-fame in the 1980s. The complicated past truth is that the artist was neither the homosexual hero that, for instance, Derek Jarman presented on film in his twentieth-century film about the artist, nor so entirely devout that, as certain art scholars unbelievably claim, his Boy With a Basket of Fruit is actually a portrait of Jesus.

His initial paintings indeed make explicit erotic implications, or including propositions. It's as if Caravaggio, then a penniless young artist, identified with Rome's prostitutes, offering himself to live. In the Uffizi, with this idea in mind, viewers might turn to an additional initial work, the 1596 masterwork the god of wine, in which the god of alcohol gazes calmly at you as he starts to undo the black ribbon of his garment.

A few annums after Bacchus, what could have driven Caravaggio to create Amor Vincit Omnia for the artistic collector Vincenzo Giustiniani, when he was at last growing nearly established with important church commissions? This profane non-Christian god resurrects the sexual provocations of his initial works but in a more intense, uneasy way. Fifty years later, its secret seemed clear: it was a portrait of Caravaggio's lover. A English visitor viewed Victorious Cupid in about the mid-seventeenth century and was told its figure has "the body & face of [Caravaggio's|his] own youth or servant that slept with him". The name of this boy was Francesco.

The artist had been dead for about forty years when this story was documented.