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The youthful boy cries out as his head is forcefully held, a large thumb pressing into his face as his father's mighty hand grasps him by the neck. This moment from The Sacrifice of Isaac appears in the Uffizi Gallery, creating unease through Caravaggio's harrowing portrayal of the tormented youth from the biblical narrative. It seems as if the patriarch, commanded by God to sacrifice his son, could snap his neck with a solitary twist. Yet the father's chosen approach involves the silvery grey blade he holds in his remaining hand, prepared to cut Isaac's throat. A certain element remains – whoever modeled as Isaac for this breathtaking piece demonstrated extraordinary expressive ability. Within exists not only fear, surprise and begging in his shadowed gaze but additionally profound sorrow that a guardian could abandon him so utterly.

The artist took a familiar scriptural story and transformed it so vibrant and raw that its terrors seemed to unfold directly in front of the viewer

Viewing in front of the artwork, observers recognize this as a real countenance, an accurate depiction of a young subject, because the identical boy – identifiable by his tousled locks and nearly dark pupils – appears in two other paintings by Caravaggio. In each instance, that richly expressive visage commands the scene. In John the Baptist, he peers mischievously from the shadows while embracing a ram. In Victorious Cupid, he smirks with a hardness learned on the city's streets, his dark plumed wings demonic, a naked child creating chaos in a affluent residence.

Victorious Cupid, currently exhibited at a London gallery, represents one of the most discomfiting artworks ever painted. Observers feel completely unsettled gazing at it. The god of love, whose arrows inspire people with often agonizing longing, is shown as a very real, vividly lit nude figure, standing over toppled-over objects that comprise stringed devices, a musical manuscript, plate armour and an architect's T-square. This pile of possessions resembles, deliberately, the geometric and construction gear scattered across the ground in the German master's engraving Melancholy – except in this case, the melancholic disorder is created by this grinning Cupid and the turmoil he can release.

"Love looks not with the vision, but with the soul, / And thus is winged Cupid painted blind," wrote the Bard, just prior to this painting was produced around 1601. But Caravaggio's Cupid is not blind. He gazes straight at the observer. That countenance – sardonic and rosy-cheeked, staring with bold confidence as he poses unclothed – is the identical one that screams in terror in The Sacrifice of Isaac.

As the Italian master painted his multiple portrayals of the same distinctive-appearing kid in Rome at the dawn of the 17th century, he was the most celebrated sacred painter in a metropolis enflamed by Catholic revival. Abraham's Offering reveals why he was commissioned to adorn sanctuaries: he could take a scriptural narrative that had been depicted many occasions before and render it so fresh, so unfiltered and physical that the terror seemed to be happening immediately in front of the spectator.

However there was another aspect to Caravaggio, apparent as quickly as he came in Rome in the winter that concluded the sixteenth century, as a artist in his initial twenties with no teacher or patron in the city, only talent and audacity. The majority of the paintings with which he caught the sacred city's attention were everything but devout. What could be the absolute first hangs in the UK's art museum. A youth opens his crimson mouth in a scream of pain: while stretching out his filthy digits for a cherry, he has rather been attacked. Youth Bitten by a Reptile is eroticism amid squalor: observers can discern Caravaggio's gloomy room mirrored in the murky liquid of the glass vase.

The adolescent sports a rose-colored blossom in his hair – a emblem of the sex commerce in Renaissance art. Northern Italian artists such as Tiziano and Jacopo Palma depicted courtesans grasping blooms and, in a work destroyed in the second world war but known through images, Caravaggio represented a famous woman prostitute, holding a posy to her chest. The meaning of all these botanical indicators is clear: intimacy for purchase.

What are we to interpret of Caravaggio's sensual depictions of youths – and of a particular boy in specific? It is a inquiry that has divided his interpreters since he achieved widespread recognition in the twentieth century. The complex past truth is that the artist was not the queer hero that, for instance, the filmmaker presented on film in his 1986 movie about the artist, nor so completely pious that, as some art scholars unbelievably claim, his Youth Holding Fruit is actually a likeness of Christ.

His initial paintings indeed offer overt erotic implications, or even offers. It's as if Caravaggio, then a destitute youthful artist, aligned with Rome's sex workers, selling himself to survive. In the Uffizi, with this idea in consideration, viewers might look to an additional early creation, the sixteenth-century masterwork the god of wine, in which the god of wine stares coolly at you as he begins to untie the dark sash of his garment.

A few years after the wine deity, what could have motivated the artist to create Victorious Cupid for the art collector Vincenzo Giustiniani, when he was at last becoming almost respectable with important church commissions? This profane pagan god resurrects the erotic challenges of his initial works but in a increasingly intense, unsettling manner. Fifty years later, its secret seemed obvious: it was a portrait of the painter's lover. A British traveller viewed the painting in about the mid-seventeenth century and was told its figure has "the body & face of [Caravaggio's|his] owne boy or assistant that slept with him". The identity of this adolescent was Francesco.

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