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A youthful lad screams while his skull is forcefully held, a massive digit digging into his face as his parent's powerful palm holds him by the throat. That scene from The Sacrifice of Isaac visits the Florentine museum, evoking unease through Caravaggio's chilling portrayal of the suffering youth from the biblical narrative. It appears as if the patriarch, instructed by the Divine to kill his son, could snap his neck with a solitary turn. Yet the father's preferred method involves the silvery steel blade he holds in his remaining hand, prepared to slit the boy's throat. One certain aspect remains – whomever modeled as Isaac for this astonishing piece demonstrated remarkable expressive skill. There exists not just fear, surprise and pleading in his shadowed gaze but also deep grief that a protector could betray him so completely.

He took a well-known biblical story and transformed it so vibrant and raw that its terrors appeared to unfold directly in front of the viewer

Viewing in front of the artwork, viewers identify this as a actual face, an accurate depiction of a adolescent model, because the same boy – recognizable by his tousled locks and nearly black eyes – features in several other paintings by Caravaggio. In every instance, that highly expressive visage dominates the scene. In Youth With a Ram, he gazes mischievously from the darkness while holding a ram. In Victorious Cupid, he grins with a toughness acquired on the city's alleys, his black feathery wings demonic, a unclothed adolescent creating riot in a well-to-do dwelling.

Victorious Cupid, currently exhibited at a London museum, represents one of the most embarrassing masterpieces ever painted. Observers feel totally disoriented gazing at it. The god of love, whose darts fill people with often agonizing longing, is shown as a extremely tangible, vividly illuminated nude form, standing over toppled-over objects that comprise stringed devices, a musical score, plate armor and an architect's ruler. This heap of items echoes, deliberately, the mathematical and construction gear scattered across the ground in the German master's engraving Melencolia I – save in this case, the gloomy mess is created by this grinning Cupid and the mayhem he can release.

"Love sees not with the eyes, but with the mind, / And therefore is winged Love painted sightless," wrote the Bard, shortly before this work was created around 1601. But Caravaggio's god is not blind. He gazes straight at the observer. That countenance – sardonic and ruddy-faced, staring with bold confidence as he poses unclothed – is the identical one that shrieks in terror in Abraham's Test.

When the Italian master created his three portrayals of the identical unusual-appearing kid in Rome at the dawn of the 17th century, he was the most acclaimed sacred artist in a metropolis ignited by religious renewal. The Sacrifice of Isaac reveals why he was commissioned to adorn sanctuaries: he could take a scriptural story that had been portrayed numerous times before and make it so fresh, so raw and physical that the horror appeared to be happening immediately before the spectator.

Yet there existed a different aspect to Caravaggio, apparent as quickly as he came in the capital in the winter that ended 1592, as a artist in his initial 20s with no teacher or supporter in the urban center, only skill and boldness. The majority of the paintings with which he captured the sacred city's attention were anything but devout. That may be the very first resides in London's National Gallery. A young man opens his red lips in a scream of pain: while stretching out his dirty fingers for a cherry, he has rather been bitten. Youth Bitten by a Reptile is eroticism amid poverty: observers can discern Caravaggio's dismal room reflected in the murky liquid of the transparent container.

The adolescent wears a rose-colored blossom in his hair – a emblem of the sex commerce in Renaissance painting. Northern Italian artists such as Tiziano and Jacopo Palma depicted courtesans grasping blooms and, in a work destroyed in the second world war but documented through photographs, Caravaggio portrayed a famous woman prostitute, clutching a bouquet to her bosom. The message of all these botanical signifiers is obvious: sex for purchase.

What are we to interpret of Caravaggio's erotic portrayals of youths – and of a particular boy in particular? It is a question that has split his interpreters since he gained widespread recognition in the twentieth century. The complicated past truth is that the painter was not the homosexual icon that, for instance, the filmmaker put on film in his twentieth-century film about the artist, nor so entirely pious that, as certain art historians improbably assert, his Youth Holding Fruit is actually a portrait of Christ.

His early works do make explicit sexual implications, or including propositions. It's as if the painter, then a penniless youthful artist, aligned with Rome's sex workers, selling himself to survive. In the Florentine gallery, with this thought in consideration, viewers might turn to an additional initial work, the sixteenth-century masterwork Bacchus, in which the god of alcohol gazes coolly at the spectator as he starts to untie the black ribbon of his robe.

A several annums after the wine deity, what could have driven Caravaggio to paint Victorious Cupid for the artistic collector the nobleman, when he was at last growing almost respectable with prestigious ecclesiastical projects? This unholy non-Christian deity revives the sexual challenges of his early paintings but in a increasingly powerful, unsettling way. Half a century later, its secret seemed obvious: it was a representation of Caravaggio's companion. A English traveller saw the painting in about the mid-seventeenth century and was told its figure has "the physique and countenance of [Caravaggio's|his] owne youth or servant that slept with him". The name of this boy was Francesco.

The painter had been dead for about forty annums when this account was recorded.