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The youthful boy screams as his skull is forcefully gripped, a large digit pressing into his cheek as his parent's mighty hand grasps him by the throat. This moment from Abraham's Sacrifice appears in the Uffizi Gallery, evoking unease through the artist's chilling rendition of the tormented child from the scriptural account. The painting seems as if Abraham, instructed by the Divine to sacrifice his son, could break his neck with a solitary turn. However Abraham's preferred method involves the silvery grey blade he grips in his other palm, prepared to slit Isaac's neck. A definite element remains – whoever posed as the sacrifice for this breathtaking piece demonstrated extraordinary acting ability. There exists not just fear, surprise and begging in his shadowed eyes but also profound sorrow that a guardian could abandon him so completely.

The artist took a familiar scriptural tale and transformed it so vibrant and raw that its terrors seemed to happen right in view of the viewer

Standing before the painting, observers identify this as a real countenance, an precise depiction of a young model, because the same youth – recognizable by his tousled locks and nearly dark pupils – features in several additional works by the master. In every case, that richly expressive visage dominates the scene. In Youth With a Ram, he peers mischievously from the shadows while holding a ram. In Amor Vincit Omnia, he smirks with a toughness learned on Rome's streets, his black plumed appendages demonic, a unclothed child creating chaos in a well-to-do residence.

Amor Vincit Omnia, currently exhibited at a British gallery, constitutes one of the most discomfiting masterpieces ever created. Viewers feel completely unsettled looking at it. The god of love, whose arrows inspire people with frequently painful longing, is portrayed as a very real, vividly illuminated unclothed figure, straddling overturned items that include stringed instruments, a music manuscript, metal armor and an builder's T-square. This heap of items echoes, intentionally, the geometric and architectural equipment scattered across the floor in the German master's print Melencolia I – save here, the gloomy disorder is caused by this smirking Cupid and the mayhem he can unleash.

"Love looks not with the vision, but with the soul, / And thus is winged Love depicted blind," penned Shakespeare, just before this work was produced around 1601. But the painter's god is not unseeing. He gazes directly at the observer. That countenance – ironic and ruddy-cheeked, staring with bold confidence as he poses naked – is the same one that shrieks in terror in Abraham's Test.

When Michelangelo Merisi da Caravaggio painted his three images of the same unusual-appearing kid in Rome at the dawn of the seventeenth century, he was the most acclaimed religious painter in a city enflamed by religious renewal. Abraham's Offering demonstrates why he was sought to adorn churches: he could take a scriptural story that had been depicted numerous occasions before and render it so fresh, so unfiltered and physical that the terror seemed to be occurring immediately in front of you.

Yet there existed a different side to Caravaggio, evident as soon as he arrived in the capital in the cold season that ended the sixteenth century, as a painter in his early twenties with no mentor or patron in the urban center, only talent and boldness. Most of the works with which he caught the holy city's eye were anything but devout. What could be the absolute first resides in London's National Gallery. A youth parts his red lips in a yell of pain: while stretching out his filthy fingers for a cherry, he has rather been attacked. Boy Bitten By a Lizard is eroticism amid squalor: observers can discern the painter's gloomy chamber mirrored in the murky liquid of the transparent vase.

The adolescent sports a pink flower in his hair – a emblem of the sex commerce in Renaissance art. Northern Italian painters such as Titian and Jacopo Palma depicted courtesans grasping flowers and, in a painting lost in the WWII but documented through images, Caravaggio represented a renowned female prostitute, holding a posy to her chest. The message of all these floral indicators is obvious: intimacy for sale.

How are we to interpret of the artist's erotic depictions of youths – and of a particular adolescent in particular? It is a question that has divided his interpreters since he gained mega-fame in the twentieth century. The complex past reality is that the painter was neither the homosexual icon that, for instance, Derek Jarman presented on film in his twentieth-century movie Caravaggio, nor so completely pious that, as some art historians unbelievably assert, his Youth Holding Fruit is in fact a likeness of Christ.

His early paintings indeed make explicit sexual suggestions, or including propositions. It's as if Caravaggio, then a penniless youthful artist, aligned with Rome's prostitutes, selling himself to live. In the Uffizi, with this idea in mind, viewers might turn to another early work, the sixteenth-century masterwork Bacchus, in which the deity of alcohol stares coolly at the spectator as he starts to undo the dark sash of his robe.

A few annums following Bacchus, what could have motivated Caravaggio to create Victorious Cupid for the art patron Vincenzo Giustiniani, when he was finally growing nearly established with prestigious church commissions? This unholy pagan god revives the sexual challenges of his early paintings but in a more powerful, uneasy manner. Half a century afterwards, its hidden meaning seemed clear: it was a portrait of Caravaggio's lover. A English traveller saw the painting in about the mid-seventeenth century and was told its figure has "the body & face of [Caravaggio's|his] owne youth or assistant that slept with him". The identity of this boy was Cecco.

The painter had been deceased for about forty years when this account was documented.