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A youthful boy cries out as his head is forcefully held, a large digit digging into his face as his father's powerful palm holds him by the throat. That moment from Abraham's Sacrifice appears in the Florentine museum, creating unease through the artist's chilling portrayal of the tormented child from the scriptural account. It appears as if Abraham, commanded by God to kill his offspring, could snap his neck with a single twist. Yet the father's chosen method involves the silvery grey blade he grips in his other palm, prepared to cut Isaac's throat. A certain element remains – whomever modeled as Isaac for this breathtaking piece displayed extraordinary expressive ability. There exists not just dread, shock and pleading in his shadowed gaze but additionally profound sorrow that a guardian could abandon him so utterly.

The artist took a familiar scriptural tale and made it so fresh and visceral that its horrors appeared to unfold directly in front of you

Viewing in front of the artwork, viewers recognize this as a real face, an precise depiction of a adolescent subject, because the same boy – recognizable by his tousled locks and almost dark pupils – features in several other paintings by the master. In every case, that highly expressive visage commands the scene. In Youth With a Ram, he gazes mischievously from the shadows while embracing a lamb. In Amor Vincit Omnia, he smirks with a hardness acquired on Rome's streets, his black feathery appendages sinister, a naked child creating chaos in a well-to-do residence.

Victorious Cupid, presently exhibited at a London gallery, constitutes one of the most embarrassing masterpieces ever created. Viewers feel completely disoriented gazing at it. Cupid, whose arrows inspire people with often agonizing longing, is portrayed as a extremely real, vividly lit nude form, standing over overturned items that include stringed devices, a musical manuscript, plate armor and an builder's T-square. This pile of possessions echoes, deliberately, the geometric and architectural gear strewn across the ground in the German master's engraving Melancholy – except in this case, the melancholic disorder is created by this smirking Cupid and the mayhem he can unleash.

"Love sees not with the eyes, but with the mind, / And thus is feathered Cupid depicted blind," wrote the Bard, just prior to this work was created around 1601. But the painter's Cupid is not unseeing. He stares directly at the observer. That countenance – sardonic and ruddy-cheeked, looking with brazen assurance as he poses naked – is the same one that shrieks in terror in The Sacrifice of Isaac.

When the Italian master painted his multiple portrayals of the identical unusual-appearing kid in Rome at the dawn of the seventeenth century, he was the most acclaimed sacred painter in a city enflamed by Catholic revival. The Sacrifice of Isaac demonstrates why he was sought to adorn churches: he could take a biblical story that had been portrayed numerous occasions before and render it so fresh, so raw and visceral that the terror appeared to be occurring directly before you.

However there was a different side to the artist, evident as soon as he came in the capital in the winter that ended the sixteenth century, as a painter in his initial twenties with no teacher or supporter in the city, just skill and boldness. The majority of the paintings with which he captured the holy metropolis's eye were anything but devout. What may be the very earliest hangs in London's art museum. A youth parts his crimson mouth in a scream of pain: while stretching out his filthy digits for a cherry, he has rather been bitten. Youth Bitten by a Reptile is sensuality amid poverty: observers can see the painter's dismal chamber reflected in the cloudy liquid of the glass container.

The boy sports a rose-colored blossom in his coiffure – a symbol of the sex commerce in early modern painting. Venetian artists such as Titian and Jacopo Palma depicted courtesans holding blooms and, in a work destroyed in the WWII but documented through photographs, Caravaggio portrayed a renowned woman prostitute, clutching a bouquet to her bosom. The meaning of all these botanical indicators is clear: intimacy for purchase.

What are we to make of the artist's sensual portrayals of youths – and of one adolescent in particular? It is a inquiry that has split his interpreters since he achieved widespread recognition in the twentieth century. The complicated historical truth is that the artist was neither the queer hero that, for example, the filmmaker presented on screen in his twentieth-century movie about the artist, nor so entirely devout that, as some artistic historians unbelievably assert, his Youth Holding Fruit is in fact a portrait of Christ.

His early paintings do offer explicit erotic suggestions, or including offers. It's as if the painter, then a penniless youthful creator, identified with the city's prostitutes, selling himself to live. In the Florentine gallery, with this idea in mind, observers might turn to another initial work, the sixteenth-century masterwork the god of wine, in which the god of alcohol stares coolly at you as he begins to undo the dark sash of his robe.

A few years following Bacchus, what could have motivated Caravaggio to paint Amor Vincit Omnia for the artistic collector the nobleman, when he was at last growing nearly respectable with important ecclesiastical commissions? This unholy non-Christian deity revives the sexual provocations of his early paintings but in a increasingly intense, unsettling way. Fifty years later, its hidden meaning seemed clear: it was a portrait of the painter's companion. A British visitor viewed Victorious Cupid in about the mid-seventeenth century and was informed its figure has "the physique and countenance of [Caravaggio's|his] owne youth or assistant that laid with him". The name of this boy was Francesco.

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