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A young boy screams as his head is firmly held, a massive digit digging into his face as his parent's powerful hand holds him by the neck. That scene from The Sacrifice of Isaac appears in the Florentine museum, creating unease through Caravaggio's chilling portrayal of the tormented child from the scriptural narrative. The painting appears as if the patriarch, instructed by the Divine to kill his offspring, could break his spinal column with a single turn. However the father's preferred method involves the metallic steel knife he holds in his remaining hand, ready to cut Isaac's throat. One certain element stands out – whoever modeled as Isaac for this breathtaking work displayed extraordinary acting ability. Within exists not only dread, surprise and begging in his darkened gaze but also deep grief that a guardian could abandon him so utterly.

The artist adopted a well-known scriptural story and transformed it so fresh and raw that its terrors appeared to unfold directly in view of the viewer

Standing in front of the painting, observers recognize this as a real countenance, an precise record of a young model, because the identical boy – recognizable by his tousled hair and almost black pupils – features in two additional paintings by Caravaggio. In each instance, that highly emotional face dominates the scene. In John the Baptist, he peers playfully from the darkness while embracing a lamb. In Victorious Cupid, he grins with a toughness learned on Rome's alleys, his dark plumed wings sinister, a unclothed child running chaos in a well-to-do dwelling.

Victorious Cupid, presently displayed at a London gallery, constitutes one of the most discomfiting artworks ever painted. Observers feel completely unsettled looking at it. The god of love, whose darts inspire people with often agonizing desire, is portrayed as a very real, brightly illuminated unclothed figure, straddling toppled-over items that comprise stringed devices, a music manuscript, metal armour and an architect's T-square. This heap of possessions resembles, deliberately, the mathematical and construction equipment scattered across the ground in the German master's print Melencolia I – save in this case, the melancholic mess is created by this smirking Cupid and the mayhem he can release.

"Love looks not with the vision, but with the soul, / And therefore is feathered Cupid depicted blind," penned the Bard, just prior to this painting was produced around the early 1600s. But the painter's god is not unseeing. He gazes directly at the observer. That countenance – ironic and ruddy-cheeked, looking with bold assurance as he poses naked – is the same one that shrieks in fear in Abraham's Test.

When the Italian master created his multiple images of the identical unusual-looking kid in Rome at the start of the seventeenth century, he was the most celebrated religious artist in a metropolis enflamed by Catholic renewal. Abraham's Offering reveals why he was sought to decorate churches: he could take a scriptural narrative that had been portrayed many times previously and render it so new, so unfiltered and visceral that the horror seemed to be happening immediately before you.

Yet there existed a different side to the artist, evident as soon as he arrived in the capital in the cold season that concluded 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 caught the holy metropolis's attention were everything but devout. What could be the very first resides in the UK's National Gallery. A young man opens his red lips in a scream of pain: while reaching out his filthy fingers for a fruit, he has rather been attacked. Youth Bitten by a Reptile is sensuality amid poverty: observers can see the painter's dismal chamber mirrored in the murky waters of the transparent container.

The boy sports a pink blossom in his coiffure – a symbol of the erotic commerce in Renaissance art. Venetian artists such as Tiziano and Palma Vecchio portrayed courtesans grasping blooms and, in a painting lost in the second world war but documented through images, the master represented a renowned female prostitute, holding a bouquet to her chest. The meaning of all these floral signifiers is obvious: sex for purchase.

What are we to interpret of Caravaggio's sensual depictions of boys – and of one boy in specific? It is a question that has split his commentators since he gained mega-fame in the twentieth century. The complex past truth is that the painter was not the homosexual hero that, for instance, Derek Jarman put on screen in his twentieth-century film Caravaggio, nor so completely pious that, as certain artistic historians improbably assert, his Youth Holding Fruit is in fact a likeness of Jesus.

His initial works do make overt erotic implications, or even propositions. It's as if the painter, then a penniless youthful creator, identified with Rome's sex workers, selling himself to live. In the Florentine gallery, with this idea in consideration, observers might turn to an additional initial creation, the 1596 masterwork the god of wine, in which the god of wine gazes coolly at you as he starts to untie the black sash of his garment.

A several annums after the wine deity, what could have motivated the artist to paint Victorious Cupid for the art patron the nobleman, when he was finally growing nearly established with important church projects? This profane non-Christian deity resurrects the erotic provocations of his early works but in a more powerful, unsettling manner. Fifty years later, its secret seemed obvious: it was a portrait of Caravaggio's companion. A British visitor viewed the painting in about the mid-seventeenth century and was told its subject has "the physique and countenance of [Caravaggio's|his] owne youth or servant that laid with him". The identity of this boy was Cecco.

The artist had been deceased for about 40 years when this story was recorded.