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The young lad cries out while his skull is firmly gripped, a massive digit digging into his cheek as his parent's powerful hand grasps him by the neck. That scene from Abraham's Sacrifice appears in the Uffizi Gallery, evoking distress through Caravaggio's harrowing portrayal of the tormented child from the biblical account. The painting seems as if Abraham, instructed by God to kill his son, could break his neck with a single twist. Yet Abraham's chosen approach involves the metallic steel blade he grips in his other palm, ready to cut the boy's throat. One definite aspect stands out – whoever posed as Isaac for this astonishing work demonstrated extraordinary expressive ability. There exists not only fear, surprise and begging in his shadowed gaze but additionally profound sorrow 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 appeared to happen right in front of the viewer

Viewing in front of the artwork, viewers recognize this as a real countenance, an precise depiction of a young subject, because the same youth – identifiable by his disheveled locks and nearly dark pupils – features in several other works by Caravaggio. In each case, that highly expressive visage commands the composition. In John the Baptist, he peers playfully from the darkness while holding a ram. In Victorious Cupid, he smirks with a toughness learned on Rome's streets, his black feathery wings demonic, a naked adolescent creating chaos in a affluent dwelling.

Victorious Cupid, presently exhibited at a British gallery, constitutes one of the most embarrassing masterpieces ever created. Observers feel totally disoriented looking at it. Cupid, whose darts inspire people with often painful longing, is shown as a very tangible, brightly illuminated nude figure, straddling toppled-over items that comprise musical instruments, a music score, metal armor and an architect's ruler. This pile of possessions echoes, intentionally, the mathematical and construction gear scattered across the floor in the German master's print Melencolia I – save in this case, the melancholic disorder is caused by this smirking Cupid and the turmoil he can release.

"Love looks not with the vision, but with the soul, / And thus is feathered Love depicted sightless," penned Shakespeare, shortly prior to this work was created around 1601. But the painter's god is not unseeing. He gazes straight at the observer. That countenance – sardonic and ruddy-cheeked, looking with brazen confidence as he poses naked – is the same one that screams in terror in The Sacrifice of Isaac.

When the Italian master created his multiple portrayals of the same unusual-looking youth in Rome at the start of the 17th century, he was the most celebrated sacred artist in a city ignited by religious revival. Abraham's Offering demonstrates why he was sought to decorate sanctuaries: he could take a scriptural narrative that had been depicted many times previously and render it so fresh, so raw and visceral that the terror seemed to be occurring immediately before you.

However there was a different aspect to Caravaggio, evident as quickly as he came in Rome in the cold season that concluded 1592, as a painter in his initial 20s with no mentor or supporter in the urban center, just skill and boldness. The majority of the paintings with which he caught the sacred metropolis's eye were anything but holy. What could be the absolute earliest resides in London's National Gallery. A young man parts his red mouth in a scream of pain: while reaching out his filthy fingers for a fruit, he has instead been bitten. Boy Bitten By a Lizard is sensuality amid poverty: observers can see the painter's gloomy chamber reflected in the murky waters of the transparent vase.

The boy sports a rose-colored flower in his hair – a symbol of the erotic trade in Renaissance art. Venetian painters such as Tiziano and Palma Vecchio portrayed prostitutes grasping flowers and, in a painting destroyed in the second world war but documented through images, Caravaggio represented a renowned female courtesan, holding a bouquet to her bosom. The message of all these floral signifiers is clear: intimacy for purchase.

What are we to interpret of Caravaggio's sensual portrayals of youths – and of a particular adolescent in specific? It is a inquiry that has split his commentators ever since he gained widespread recognition in the twentieth century. The complex historical reality is that the painter was neither the queer hero that, for instance, Derek Jarman put on screen in his twentieth-century film Caravaggio, nor so entirely pious that, as some artistic scholars improbably assert, his Boy With a Basket of Fruit is actually a likeness of Christ.

His initial paintings indeed offer explicit erotic implications, or even offers. It's as if Caravaggio, then a penniless youthful artist, identified with Rome's prostitutes, offering himself to live. In the Uffizi, with this idea in consideration, viewers might look to an additional early work, the 1596 masterwork the god of wine, in which the god of alcohol gazes calmly at the spectator as he begins to undo the dark ribbon of his garment.

A several annums after the wine deity, what could have driven Caravaggio to paint Amor Vincit Omnia for the art collector Vincenzo Giustiniani, when he was at last growing nearly respectable with important ecclesiastical commissions? This unholy pagan deity revives the erotic provocations of his initial paintings but in a increasingly powerful, unsettling way. Fifty years afterwards, its secret seemed clear: it was a portrait of Caravaggio's lover. A British visitor viewed Victorious Cupid in about the mid-seventeenth century and was informed its figure has "the body & face of [Caravaggio's|his] owne youth or servant that laid with him". The name of this adolescent was Francesco.

The painter had been deceased for about 40 annums when this account was recorded.