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A youthful boy screams while his head is firmly gripped, a massive digit digging into his cheek as his father's mighty palm holds him by the neck. This scene from The Sacrifice of Isaac appears in the Uffizi Gallery, creating unease through Caravaggio's harrowing portrayal of the suffering youth from the scriptural account. It seems as if Abraham, commanded by the Divine to sacrifice his offspring, could snap his neck with a solitary turn. However the father's preferred method involves the metallic steel blade he holds in his other palm, prepared to cut Isaac's throat. A certain aspect remains – whomever modeled as Isaac for this breathtaking work demonstrated remarkable expressive skill. Within exists not only fear, surprise and pleading in his darkened gaze but also profound sorrow that a protector could betray him so completely.

The artist took a familiar biblical story and transformed it so vibrant and visceral that its terrors seemed to happen directly in front of the viewer

Viewing in front of the artwork, viewers recognize this as a real face, an accurate record of a young model, because the identical boy – identifiable by his disheveled hair and nearly black pupils – features in two other works by the master. In each case, that richly expressive face commands the scene. In Youth With a Ram, he gazes mischievously from the shadows while holding a lamb. In Victorious Cupid, he smirks with a hardness learned on the city's streets, his black plumed appendages demonic, a unclothed adolescent running chaos in a affluent dwelling.

Amor Vincit Omnia, currently exhibited at a British gallery, constitutes one of the most embarrassing artworks ever painted. Viewers feel totally disoriented looking at it. Cupid, whose arrows fill people with frequently painful longing, is portrayed as a extremely real, vividly illuminated unclothed figure, straddling overturned items that comprise musical instruments, a music manuscript, metal armour and an builder's ruler. This heap of items resembles, deliberately, the mathematical and construction equipment scattered across the ground in Albrecht Dürer's print Melencolia I – save in this case, the melancholic disorder is created by this smirking Cupid and the mayhem he can release.

"Affection looks not with the eyes, but with the mind, / And therefore is winged Love depicted sightless," wrote Shakespeare, shortly prior to this painting was created around 1601. But Caravaggio's god is not blind. He stares straight at you. That face – sardonic 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 created his three images of the same unusual-looking kid in the Eternal City at the dawn of the 17th century, he was the highly celebrated sacred painter in a city enflamed by religious revival. Abraham's Offering reveals why he was sought to decorate churches: he could take a scriptural story that had been depicted numerous occasions previously and render it so fresh, so unfiltered and visceral that the terror seemed to be happening immediately before the spectator.

Yet there existed another aspect to Caravaggio, evident as soon as he came in Rome in the cold season that ended 1592, as a painter in his early 20s with no teacher or supporter in the urban center, only talent and boldness. The majority of the paintings with which he caught the holy city's attention were everything but holy. What may be the very first hangs in London's art museum. A young man opens his red mouth in a yell of agony: while stretching out his filthy fingers for a fruit, he has rather been bitten. Youth Bitten by a Reptile is sensuality amid poverty: viewers can see the painter's gloomy room reflected in the cloudy liquid of the glass vase.

The adolescent wears a pink flower in his hair – a emblem of the sex commerce in Renaissance painting. Northern Italian painters such as Titian and Jacopo Palma depicted prostitutes holding blooms and, in a painting lost in the second world war but known through images, the master portrayed a renowned female prostitute, holding a bouquet to her chest. The meaning of all these floral signifiers is clear: intimacy for sale.

What are we to make of Caravaggio's erotic depictions of boys – and of a particular adolescent in particular? It is a inquiry that has split his commentators ever since he achieved mega-fame in the twentieth century. The complicated historical reality is that the artist was not the homosexual icon that, for example, the filmmaker put on film in his twentieth-century film Caravaggio, nor so completely pious that, as some artistic historians unbelievably claim, his Youth Holding Fruit is in fact a likeness of Christ.

His initial works do offer overt erotic suggestions, or even offers. It's as if Caravaggio, then a destitute youthful creator, identified with the city's sex workers, selling himself to live. In the Uffizi, with this idea in consideration, observers might turn to an additional early creation, the sixteenth-century masterwork Bacchus, in which the god of alcohol gazes calmly at you as he starts to undo the dark ribbon of his garment.

A several years following the wine deity, what could have driven the artist to create Victorious Cupid for the artistic patron the nobleman, when he was finally growing nearly established with important church commissions? This unholy pagan god resurrects the sexual challenges of his early paintings but in a more intense, unsettling way. Half a century later, its hidden meaning seemed clear: it was a representation of the painter's lover. A British traveller viewed the painting in about 1649 and was informed its subject has "the body & face of [Caravaggio's|his] own youth or assistant that slept with him". The identity of this boy was Francesco.

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