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A youthful boy screams as his skull is forcefully gripped, a massive digit digging into his cheek as his father's powerful hand holds him by the neck. That moment from Abraham's Sacrifice appears in the Florentine museum, evoking unease through the artist's chilling rendition of the tormented child from the biblical account. It seems as if Abraham, instructed by God to kill his son, could break his spinal column with a single turn. Yet the father's preferred method involves the metallic steel knife he holds in his other palm, prepared to slit the boy's neck. A definite aspect stands out – whomever posed as the sacrifice for this breathtaking work displayed extraordinary expressive skill. There exists not only dread, surprise and begging in his darkened eyes but additionally profound sorrow that a guardian could abandon him so utterly.

The artist adopted a familiar biblical story and made it so vibrant and visceral that its horrors appeared to unfold directly in front of you

Viewing in front of the painting, viewers identify this as a real face, an precise record of a young model, because the same boy – identifiable by his tousled hair and nearly black pupils – features in two other paintings by the master. In each instance, that highly emotional face commands the scene. In John the Baptist, he peers playfully from the shadows while holding a lamb. In Victorious Cupid, he grins with a hardness acquired on Rome's alleys, his dark plumed wings sinister, a unclothed adolescent running riot in a well-to-do dwelling.

Victorious Cupid, presently exhibited at a London museum, represents one of the most discomfiting masterpieces ever painted. Viewers feel completely disoriented gazing at it. The god of love, whose darts inspire people with often painful longing, is shown as a extremely tangible, vividly lit nude form, straddling toppled-over objects that include musical devices, a musical score, metal armour and an architect's T-square. This heap of items echoes, intentionally, the geometric and architectural gear scattered across the floor in Albrecht Dürer's print Melencolia I – save in this case, the melancholic disorder is caused by this smirking Cupid and the turmoil he can release.

"Affection looks not with the eyes, but with the mind, / And therefore is feathered Cupid depicted blind," penned the Bard, shortly before this work was created around the early 1600s. But the painter's god is not blind. He gazes straight at you. That countenance – sardonic and rosy-cheeked, staring with bold assurance as he poses unclothed – is the same one that shrieks in fear in Abraham's Test.

When the Italian master created his multiple portrayals of the same distinctive-looking kid in the Eternal City at the dawn of the seventeenth century, he was the most acclaimed sacred painter in a metropolis ignited by religious revival. Abraham's Offering reveals why he was sought to adorn churches: he could adopt a scriptural narrative that had been depicted numerous occasions previously and make it so new, so raw and visceral that the horror appeared to be occurring immediately in front of you.

Yet there existed another side to the artist, apparent as quickly as he came in the capital in the winter that concluded the sixteenth century, as a artist in his initial twenties with no teacher or patron in the urban center, only skill and boldness. The majority of the paintings with which he caught the holy city's eye were anything but holy. What could be the absolute earliest hangs in London's National Gallery. A young man opens his crimson mouth in a scream of agony: while reaching out his filthy fingers for a cherry, he has instead been bitten. Boy Bitten By a Lizard is eroticism amid squalor: viewers can see Caravaggio's dismal chamber reflected in the cloudy waters of the glass vase.

The adolescent wears a rose-colored blossom in his hair – a symbol of the erotic trade in early modern art. Venetian painters such as Titian and Palma Vecchio portrayed prostitutes holding flowers and, in a work destroyed in the WWII but known through photographs, the master portrayed a renowned female courtesan, holding a bouquet to her chest. The message of all these floral signifiers is obvious: sex for sale.

How are we to make of the artist's erotic portrayals of boys – and of a particular adolescent in particular? It is a question that has split his interpreters ever since he gained widespread recognition in the twentieth century. The complex historical reality is that the artist was not the homosexual hero that, for instance, Derek Jarman presented on screen in his 1986 movie about the artist, nor so entirely devout that, as some artistic historians unbelievably claim, his Youth Holding Fruit is actually a likeness of Christ.

His initial works do make overt sexual suggestions, or including offers. It's as if the painter, then a penniless young artist, identified with Rome's sex workers, offering himself to live. In the Florentine gallery, with this thought in consideration, viewers might look to another early work, the 1596 masterpiece the god of wine, in which the god of alcohol gazes coolly at you as he starts to untie the dark sash of his robe.

A several years following the wine deity, what could have driven Caravaggio to create Amor Vincit Omnia for the artistic collector the nobleman, when he was at last becoming almost respectable with prestigious church commissions? This profane non-Christian deity resurrects the erotic challenges of his early works but in a increasingly intense, uneasy manner. Fifty years afterwards, its secret seemed obvious: it was a representation of Caravaggio's lover. A English visitor viewed Victorious Cupid in about 1649 and was told its figure has "the body & face of [Caravaggio's|his] own boy or servant that slept with him". The name of this adolescent was Francesco.

The artist had been deceased for about forty annums when this account was documented.