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A youthful boy cries out while his head is forcefully gripped, a large digit digging into his face as his parent's mighty palm grasps him by the neck. That scene from Abraham's Sacrifice visits the Uffizi Gallery, evoking unease through the artist's chilling rendition of the suffering child from the scriptural narrative. The painting seems as if Abraham, commanded by the Divine to sacrifice his offspring, could break his spinal column with a solitary twist. Yet Abraham's preferred approach involves the metallic steel knife he holds in his other palm, ready to cut Isaac's throat. A certain aspect remains – whomever posed as Isaac for this astonishing work displayed remarkable acting ability. Within exists not only fear, shock and begging in his shadowed gaze but additionally deep grief that a protector could betray him so utterly.

The artist took a familiar scriptural tale and transformed it so vibrant and visceral that its horrors appeared to happen right in view of you

Viewing in front of the painting, viewers recognize this as a actual countenance, an accurate depiction of a young subject, because the identical youth – identifiable by his tousled locks and almost black pupils – features in two additional paintings by Caravaggio. In every case, that highly emotional face commands the composition. In John the Baptist, he gazes mischievously from the darkness while holding a lamb. In Victorious Cupid, he grins with a hardness acquired on Rome's alleys, his dark feathery appendages sinister, a naked adolescent running riot in a affluent dwelling.

Victorious Cupid, presently displayed at a British gallery, represents one of the most embarrassing masterpieces ever painted. Observers feel completely disoriented gazing at it. The god of love, whose darts inspire people with often painful desire, is shown as a very real, vividly illuminated unclothed form, standing over overturned items that comprise stringed instruments, a music score, plate armor and an architect's ruler. This heap of possessions resembles, intentionally, the mathematical and architectural gear strewn across the floor in the German master's print Melancholy – except here, the gloomy mess is caused by this grinning deity and the turmoil he can release.

"Love sees not with the eyes, but with the soul, / And thus is feathered Love painted sightless," wrote Shakespeare, shortly before this painting was produced around 1601. But Caravaggio's Cupid is not unseeing. He stares directly at the observer. That face – sardonic and rosy-faced, staring with brazen confidence as he struts naked – is the identical one that shrieks in fear in Abraham's Test.

As the Italian master created his multiple portrayals of the identical unusual-appearing youth in the Eternal City at the start of the seventeenth century, he was the most celebrated religious artist in a metropolis enflamed by Catholic revival. Abraham's Offering demonstrates why he was sought to decorate sanctuaries: he could take a scriptural narrative that had been portrayed many occasions before and make it so new, so unfiltered and physical that the horror seemed to be happening directly in front of the spectator.

However there existed a different aspect to the artist, evident as quickly as he came in Rome in the cold season that ended 1592, as a artist in his initial 20s with no teacher or supporter in the city, just skill and boldness. The majority of the works with which he captured the holy city's attention were anything but devout. What may be the very earliest hangs in London's art museum. A young man opens his crimson mouth in a yell of pain: while stretching out his dirty digits for a fruit, he has instead been attacked. Youth Bitten by a Reptile is eroticism amid poverty: viewers can discern the painter's gloomy room mirrored in the cloudy waters of the transparent vase.

The boy sports a pink blossom in his coiffure – a symbol of the sex trade in early modern painting. Venetian artists such as Tiziano and Palma Vecchio depicted courtesans grasping flowers and, in a work lost in the WWII but known through images, the master portrayed a famous woman courtesan, clutching a bouquet to her chest. The meaning of all these botanical signifiers is clear: sex for purchase.

How are we to make of the artist's erotic portrayals of boys – and of one boy in specific? It is a inquiry that has divided his commentators since he achieved widespread recognition in the 1980s. The complicated historical reality is that the artist was neither the homosexual hero that, for instance, Derek Jarman presented on film in his 1986 movie about the artist, nor so completely pious that, as some art scholars improbably claim, his Boy With a Basket of Fruit is actually a likeness of Jesus.

His early paintings do make explicit erotic suggestions, or including propositions. It's as if the painter, then a penniless young artist, aligned with Rome's prostitutes, selling himself to live. In the Florentine gallery, with this idea in consideration, viewers might turn to another initial creation, the 1596 masterwork Bacchus, in which the deity of alcohol gazes coolly at you as he starts to undo the black ribbon of his robe.

A several annums after the wine deity, what could have motivated Caravaggio to create Victorious Cupid for the art collector Vincenzo Giustiniani, when he was finally growing almost established with important ecclesiastical commissions? This profane non-Christian god resurrects the sexual provocations of his early works but in a more powerful, unsettling manner. Half a century later, its hidden meaning seemed clear: it was a representation of Caravaggio's companion. A English traveller viewed the painting in about the mid-seventeenth century and was told its figure has "the physique and countenance of [Caravaggio's|his] owne boy or assistant that laid with him". The name of this boy was Francesco.

The artist had been dead for about forty years when this story was recorded.