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A young boy cries out while his head is forcefully gripped, a massive thumb digging into his cheek as his parent's powerful hand grasps him by the throat. This moment from The Sacrifice of Isaac visits the Uffizi Gallery, creating unease through the artist's chilling rendition of the suffering youth from the scriptural account. The painting seems as if Abraham, instructed by the Divine to kill his offspring, could break his spinal column with a solitary twist. Yet the father's preferred approach involves the metallic steel blade he holds in his other hand, prepared to slit the boy's neck. A definite aspect stands out – whomever posed as Isaac for this astonishing piece displayed extraordinary acting ability. There exists not just fear, shock and begging in his shadowed eyes but also deep sorrow that a guardian could abandon him so utterly.

He took a well-known biblical story and made it so vibrant and visceral that its terrors appeared to unfold right in front of the viewer

Viewing in front of the painting, viewers recognize this as a real countenance, an precise depiction of a young subject, because the identical youth – recognizable by his disheveled locks and almost black pupils – features in several other paintings by Caravaggio. In every instance, that richly emotional visage dominates the scene. In John the Baptist, he peers playfully from the shadows while embracing a lamb. In Victorious Cupid, he grins with a toughness acquired on Rome's streets, his black feathery appendages demonic, a unclothed adolescent running chaos in a well-to-do dwelling.

Victorious Cupid, presently displayed at a British gallery, constitutes one of the most embarrassing artworks ever created. Observers feel completely disoriented gazing at it. The god of love, whose arrows inspire people with frequently painful longing, is portrayed as a very tangible, vividly illuminated unclothed form, standing over toppled-over items that include stringed devices, a music score, metal armour and an builder's ruler. This pile of items echoes, deliberately, the mathematical and architectural equipment scattered across the ground in the German master's print Melencolia I – except here, the melancholic mess is caused by this smirking deity and the turmoil he can release.

"Affection looks not with the eyes, but with the soul, / And therefore is feathered Love painted blind," wrote Shakespeare, just prior to this work was created around the early 1600s. But Caravaggio's god is not blind. He stares straight at you. That countenance – sardonic and ruddy-faced, staring with bold assurance as he poses unclothed – is the identical one that screams in fear in The Sacrifice of Isaac.

When the Italian master created his three portrayals of the identical unusual-looking kid in Rome at the dawn of the seventeenth century, he was the highly acclaimed religious artist in a city ignited by religious revival. Abraham's Offering reveals why he was commissioned to decorate churches: he could adopt a biblical narrative that had been depicted many occasions previously and render it so new, so raw and physical that the horror seemed to be happening directly in front of the spectator.

Yet there existed another side to the artist, evident as quickly as he arrived in the capital in the winter that ended 1592, as a artist in his early twenties with no teacher or supporter in the urban center, just skill and audacity. Most of the works with which he captured the sacred city's attention were anything but devout. That could be the very earliest resides in the UK's art museum. A young man parts his red lips in a yell of agony: while stretching out his filthy fingers for a cherry, he has rather been bitten. Boy Bitten By a Lizard is sensuality amid poverty: viewers can see the painter's dismal room reflected in the cloudy liquid of the transparent container.

The adolescent sports a rose-colored blossom in his coiffure – a emblem of the erotic trade in early modern painting. Northern Italian artists such as Titian and Jacopo Palma depicted prostitutes holding flowers and, in a work lost in the WWII but known through photographs, Caravaggio represented a renowned female courtesan, holding a posy to her chest. The meaning of all these botanical signifiers is clear: sex for sale.

What are we to make of the artist's erotic portrayals of youths – and of one boy in particular? It is a inquiry that has divided his interpreters since he gained widespread recognition in the twentieth century. The complex historical reality is that the artist was not the homosexual hero that, for example, Derek Jarman put on film in his 1986 film about the artist, nor so completely devout that, as certain artistic scholars improbably claim, his Youth Holding Fruit is in fact a likeness of Jesus.

His early works do offer overt erotic implications, or even offers. It's as if the painter, then a destitute youthful creator, identified with Rome's sex workers, offering himself to survive. In the Uffizi, with this idea in consideration, observers might look to another early work, the 1596 masterwork Bacchus, in which the god of alcohol stares calmly at the spectator as he begins to untie the dark ribbon of his garment.

A several annums following Bacchus, what could have motivated Caravaggio to paint Victorious Cupid for the artistic patron the nobleman, when he was at last becoming nearly respectable with prestigious ecclesiastical commissions? This profane non-Christian deity revives the sexual challenges of his early paintings but in a increasingly powerful, unsettling way. Fifty years later, its hidden meaning seemed clear: it was a representation of Caravaggio's lover. A British visitor saw Victorious Cupid in about 1649 and was informed its figure has "the physique and countenance of [Caravaggio's|his] own youth or assistant that slept with him". The identity of this boy was Francesco.

The artist had been dead for about 40 annums when this story was recorded.