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The young boy cries out while his skull is firmly gripped, a massive digit pressing into his cheek as his parent's mighty hand grasps him by the neck. This moment from The Sacrifice of Isaac visits the Florentine museum, evoking unease through the artist's chilling rendition of the suffering child from the scriptural narrative. It appears as if Abraham, commanded by God to kill his offspring, could break his neck with a solitary turn. Yet the father's chosen approach involves the silvery steel knife he holds in his remaining hand, prepared to slit Isaac's neck. A certain element remains – whoever posed as the sacrifice for this breathtaking work demonstrated remarkable acting skill. There exists not only fear, shock and pleading in his shadowed eyes but additionally deep grief that a protector could abandon him so utterly.

He adopted a familiar scriptural story and transformed it so fresh and visceral that its terrors seemed to unfold directly in view of the viewer

Viewing before the painting, observers identify this as a actual face, an accurate depiction of a adolescent model, because the identical youth – recognizable by his disheveled hair and nearly dark eyes – features in two other works by the master. In each case, that richly expressive visage commands the composition. In Youth With a Ram, he gazes playfully from the shadows while holding a ram. In Victorious Cupid, he grins with a hardness learned on Rome's streets, his dark feathery appendages demonic, a unclothed child creating chaos in a affluent residence.

Victorious Cupid, presently exhibited at a London museum, constitutes one of the most discomfiting masterpieces ever painted. Viewers feel completely disoriented looking at it. The god of love, whose arrows fill people with frequently painful longing, is shown as a extremely real, vividly lit unclothed form, standing over toppled-over items that comprise stringed instruments, a musical manuscript, plate armour and an architect's T-square. This pile of possessions echoes, intentionally, the geometric and architectural equipment scattered across the ground in Albrecht Dürer's engraving Melencolia I – save in this case, the melancholic disorder is created by this grinning Cupid and the turmoil he can unleash.

"Affection sees not with the eyes, but with the mind, / And thus is winged Love depicted blind," penned Shakespeare, shortly prior to this work was created around 1601. But Caravaggio's god is not blind. He gazes straight at you. That countenance – ironic and rosy-cheeked, looking with brazen confidence as he poses naked – is the identical one that shrieks in fear in The Sacrifice of Isaac.

As the Italian master painted his multiple portrayals of the same distinctive-appearing kid in Rome at the dawn of the 17th century, he was the highly celebrated sacred painter in a metropolis enflamed by Catholic renewal. The Sacrifice of Isaac demonstrates why he was commissioned to adorn sanctuaries: he could take a biblical story that had been portrayed many times previously and render it so new, so raw and physical that the terror seemed to be happening directly in front of you.

Yet there was another side to Caravaggio, evident as quickly as he arrived in the capital in the winter that concluded 1592, as a painter in his initial 20s with no mentor or patron in the city, only skill and audacity. The majority of the paintings with which he captured the sacred metropolis's eye were everything but holy. What could be the very earliest hangs in London's art museum. A youth parts his red lips in a yell of pain: while stretching out his filthy fingers for a cherry, he has instead 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 adolescent sports a rose-colored flower in his coiffure – a emblem of the erotic commerce in early modern art. Northern Italian painters such as Tiziano and Palma Vecchio portrayed courtesans holding flowers and, in a work destroyed in the WWII but known through photographs, Caravaggio represented a renowned female courtesan, holding a posy to her chest. The message of all these botanical indicators is obvious: sex for sale.

How are we to make of the artist's erotic depictions of boys – and of a particular boy in specific? It is a inquiry that has split his commentators ever since he gained mega-fame in the twentieth century. The complex historical truth is that the artist was not the queer hero that, for example, Derek Jarman put on screen in his twentieth-century movie about the artist, nor so completely pious that, as certain art scholars unbelievably claim, his Youth Holding Fruit is in fact a portrait of Christ.

His early paintings indeed make overt sexual suggestions, or even propositions. It's as if Caravaggio, then a penniless young creator, identified with Rome's sex workers, selling himself to live. In the Uffizi, with this idea in consideration, viewers might turn to an additional initial creation, the sixteenth-century masterpiece the god of wine, in which the deity of wine gazes coolly at the spectator as he begins to undo the black sash of his garment.

A few years following the wine deity, what could have motivated Caravaggio to create Victorious Cupid for the art patron the nobleman, when he was finally growing almost respectable with prestigious ecclesiastical commissions? This profane pagan god revives the erotic provocations of his initial paintings but in a more intense, uneasy manner. Half a century afterwards, its secret seemed obvious: it was a portrait of Caravaggio's companion. A British visitor viewed the painting in about 1649 and was informed its subject has "the physique and countenance of [Caravaggio's|his] own youth or servant that slept with him". The name of this boy was Francesco.

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