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The young boy screams while his head is firmly held, a large digit digging into his cheek as his parent's mighty hand holds him by the throat. That scene from The Sacrifice of Isaac visits the Florentine museum, creating unease through Caravaggio's harrowing portrayal of the tormented child from the scriptural narrative. It appears as if Abraham, commanded by the Divine to kill his offspring, could break his neck with a solitary turn. However the father's chosen approach involves the metallic grey knife he holds in his remaining hand, ready to slit the boy's throat. A definite aspect remains – whoever posed as the sacrifice for this astonishing work demonstrated extraordinary acting ability. Within exists not just dread, shock and pleading in his darkened gaze but also profound grief that a guardian could betray him so completely.

The artist adopted a familiar biblical tale and transformed it so fresh and visceral that its terrors seemed to happen directly in view of the viewer

Standing in front of the artwork, viewers identify this as a real countenance, an accurate depiction of a adolescent subject, because the same youth – identifiable by his disheveled hair and nearly black eyes – appears in two additional works by Caravaggio. In each case, that highly expressive face dominates the scene. In Youth With a Ram, he peers mischievously from the darkness while holding a lamb. In Amor Vincit Omnia, he grins with a toughness learned on the city's alleys, his dark plumed wings sinister, a unclothed child running riot in a well-to-do residence.

Victorious Cupid, currently exhibited at a London gallery, constitutes one of the most embarrassing masterpieces ever created. Viewers feel totally unsettled gazing at it. The god of love, whose darts inspire people with frequently agonizing longing, is portrayed as a extremely real, brightly lit nude form, straddling toppled-over objects that include stringed instruments, a musical manuscript, plate armor and an builder's ruler. This pile of items echoes, deliberately, the mathematical and architectural equipment scattered across the floor in the German master's engraving Melancholy – except here, the melancholic mess is created by this grinning Cupid and the turmoil he can release.

"Affection looks not with the eyes, but with the mind, / And thus is winged Love painted blind," penned the Bard, just before this work was produced around the early 1600s. But the painter's Cupid is not blind. He gazes directly at the observer. That countenance – sardonic and rosy-cheeked, looking with brazen confidence as he struts unclothed – is the identical one that screams in fear in The Sacrifice of Isaac.

When Michelangelo Merisi da Caravaggio painted his multiple portrayals of the identical distinctive-looking kid in Rome at the dawn of the 17th century, he was the most celebrated sacred artist in a metropolis ignited by religious renewal. Abraham's Offering demonstrates why he was sought to adorn sanctuaries: he could adopt a scriptural story that had been depicted many times before and make it so new, so unfiltered and visceral that the horror appeared to be occurring immediately in front of the spectator.

Yet there was a different side to Caravaggio, apparent as soon as he arrived in Rome in the cold season that ended 1592, as a artist in his initial 20s with no mentor or patron 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 could be the very first hangs in London's National Gallery. A young man parts his crimson mouth in a scream of agony: while reaching out his dirty fingers for a cherry, he has rather been attacked. Boy Bitten By a Lizard is eroticism amid squalor: observers can discern the painter's dismal room mirrored in the cloudy liquid of the transparent container.

The adolescent sports a pink blossom in his coiffure – a symbol of the sex commerce in early modern art. Northern Italian artists such as Titian and Jacopo Palma portrayed courtesans holding blooms and, in a painting destroyed in the WWII but documented through photographs, the master portrayed a famous woman courtesan, holding a bouquet to her chest. The message of all these botanical signifiers is obvious: sex for sale.

What are we to interpret of the artist's sensual portrayals of boys – and of one boy in specific? It is a question that has divided his interpreters since he gained widespread recognition in the 1980s. The complicated historical reality is that the painter was not the queer hero that, for instance, Derek Jarman put on screen in his 1986 film Caravaggio, nor so entirely devout that, as certain artistic scholars unbelievably assert, his Boy With a Basket of Fruit is in fact a likeness of Jesus.

His early works indeed make explicit erotic suggestions, or even propositions. It's as if Caravaggio, then a penniless youthful artist, identified with the city's prostitutes, offering himself to survive. In the Florentine gallery, with this thought in consideration, observers might look to another early work, the 1596 masterwork the god of wine, in which the deity of alcohol stares calmly at you as he starts to untie the black ribbon of his robe.

A several years following the wine deity, what could have motivated Caravaggio to paint Victorious Cupid for the artistic patron Vincenzo Giustiniani, when he was finally growing almost respectable with prestigious church commissions? This profane non-Christian deity revives the sexual challenges of his early paintings but in a increasingly intense, unsettling manner. Half a century later, its hidden meaning seemed obvious: it was a representation of Caravaggio's companion. A English traveller viewed Victorious Cupid in about 1649 and was told its figure has "the body & face of [Caravaggio's|his] own boy or servant that laid with him". The identity of this adolescent was Cecco.

The painter had been deceased for about forty annums when this account was recorded.