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A young lad cries out as his head is forcefully gripped, a large digit pressing into his cheek as his father's powerful hand holds him by the neck. That scene from The Sacrifice of Isaac appears in the Uffizi Gallery, creating distress through Caravaggio's harrowing portrayal of the tormented youth from the scriptural narrative. The painting appears as if Abraham, commanded by the Divine to kill his offspring, could break his neck with a solitary turn. However Abraham's chosen method involves the silvery steel blade he holds in his other hand, prepared to cut Isaac's throat. A certain element remains – whoever posed as Isaac for this astonishing piece demonstrated extraordinary acting skill. Within exists not just dread, surprise and pleading in his darkened eyes but also profound grief that a protector could betray him so completely.

The artist adopted a well-known scriptural story and transformed it so vibrant and raw that its terrors seemed to unfold directly in view of you

Standing in front of the painting, viewers identify this as a actual face, an precise record of a young model, because the same youth – identifiable by his disheveled hair and nearly black eyes – features in two other works by the master. In every instance, that highly expressive visage dominates the composition. In John the Baptist, he peers playfully from the darkness while embracing a lamb. In Victorious Cupid, he grins with a toughness acquired on Rome's alleys, his black plumed appendages sinister, a naked adolescent running riot in a well-to-do dwelling.

Victorious Cupid, currently displayed at a British museum, constitutes one of the most embarrassing artworks ever painted. Observers feel totally unsettled looking at it. The god of love, whose arrows fill people with often painful desire, is shown as a very real, brightly lit unclothed figure, standing over toppled-over items that include stringed instruments, a musical score, metal armor and an builder's ruler. This heap of items echoes, deliberately, the mathematical and architectural gear strewn across the floor in Albrecht Dürer's print Melancholy – save in this case, the melancholic disorder is created by this grinning deity and the turmoil he can release.

"Affection sees not with the vision, but with the mind, / And therefore is winged Cupid painted blind," penned Shakespeare, just prior to this painting was created around 1601. But Caravaggio's god is not unseeing. He stares directly at the observer. That face – ironic and ruddy-cheeked, looking with bold confidence as he struts unclothed – is the identical one that shrieks in terror in The Sacrifice of Isaac.

As the Italian master created his three portrayals of the same distinctive-looking kid in the Eternal City at the start of the 17th century, he was the most celebrated sacred artist in a metropolis enflamed by religious renewal. Abraham's Offering reveals why he was sought to decorate sanctuaries: he could adopt a scriptural story that had been depicted numerous times previously and render it so new, so raw and visceral that the horror seemed to be occurring immediately before the spectator.

However there was a different aspect to the artist, evident as soon as he arrived in the capital in the winter that concluded 1592, as a artist in his early twenties with no mentor or supporter in the urban center, only skill and boldness. Most of the paintings with which he caught the holy city's eye were everything but holy. That may be the very earliest hangs in London's art museum. A youth opens his crimson lips in a scream of pain: while stretching out his filthy fingers for a fruit, he has rather been attacked. Youth Bitten by a Reptile is eroticism amid squalor: observers can discern Caravaggio's gloomy room mirrored in the cloudy waters of the glass vase.

The adolescent wears a rose-colored blossom in his coiffure – a emblem of the erotic commerce in Renaissance painting. Venetian painters such as Tiziano and Palma Vecchio portrayed courtesans holding flowers and, in a painting destroyed in the WWII but documented through photographs, the master represented a renowned woman prostitute, clutching a bouquet to her chest. The message of all these floral indicators is obvious: sex for sale.

How are we to interpret of the artist's sensual portrayals of boys – and of a particular boy in specific? It is a inquiry that has split his commentators ever since he achieved mega-fame in the twentieth century. The complicated past reality is that the artist was not the queer icon that, for instance, Derek Jarman presented on screen in his twentieth-century movie about the artist, nor so completely devout that, as some artistic historians improbably claim, his Boy With a Basket of Fruit is in fact a likeness of Jesus.

His early paintings do make overt erotic suggestions, or even offers. It's as if Caravaggio, then a penniless young creator, identified with the city's prostitutes, selling himself to live. In the Uffizi, with this thought in consideration, viewers might look to an additional initial work, the 1596 masterwork Bacchus, in which the god of alcohol gazes coolly at the spectator as he begins to undo the dark ribbon of his robe.

A several years following Bacchus, what could have motivated the artist to create Victorious Cupid for the art patron Vincenzo Giustiniani, when he was finally growing almost respectable with important church commissions? This unholy pagan god resurrects the erotic provocations of his initial works but in a increasingly powerful, uneasy manner. Fifty years afterwards, its secret seemed clear: it was a representation of the painter'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] own boy or assistant that laid with him". The identity of this boy was Francesco.

The artist had been dead for about 40 years when this story was documented.