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A young lad cries out while his skull is forcefully held, a large thumb pressing into his face as his parent's mighty hand grasps him by the neck. That moment from The Sacrifice of Isaac appears in the Uffizi Gallery, evoking unease through the artist's harrowing portrayal of the tormented youth from the scriptural account. The painting appears as if Abraham, instructed by the Divine to sacrifice his son, could break his neck with a solitary twist. However Abraham's chosen approach involves the metallic grey blade he holds in his other hand, prepared to cut Isaac's throat. A certain aspect stands out – whomever modeled as Isaac for this astonishing piece displayed remarkable expressive skill. Within exists not just dread, shock and pleading in his darkened gaze but additionally profound grief that a protector could betray him so utterly.

He took a well-known biblical tale and made it so vibrant and raw that its horrors seemed to happen directly in front of the viewer

Standing in front of the artwork, observers identify this as a actual countenance, an precise depiction of a young subject, because the identical boy – recognizable by his tousled hair and almost dark eyes – features in two additional works by Caravaggio. In each case, that richly emotional face commands the scene. In John the Baptist, he peers playfully from the darkness while holding a ram. In Victorious Cupid, he smirks with a hardness acquired on the city's alleys, his black plumed wings demonic, a unclothed child creating riot in a affluent dwelling.

Victorious Cupid, currently exhibited at a London gallery, represents one of the most discomfiting masterpieces ever created. Observers feel totally disoriented gazing at it. The god of love, whose arrows inspire people with frequently agonizing longing, is portrayed as a very real, vividly lit nude figure, straddling overturned items that comprise musical instruments, a musical score, plate armor and an builder's T-square. This pile of items resembles, intentionally, the geometric and architectural equipment scattered across the floor in the German master's engraving Melancholy – except here, the gloomy disorder is created by this grinning deity and the mayhem he can unleash.

"Love looks not with the eyes, but with the mind, / And therefore is feathered Cupid depicted blind," penned the Bard, just prior to this painting was produced around 1601. But Caravaggio's Cupid is not unseeing. He gazes directly at you. That countenance – ironic and ruddy-faced, looking with bold confidence as he poses naked – is the identical one that screams in fear in Abraham's Test.

When Michelangelo Merisi da Caravaggio created his multiple images of the same distinctive-looking kid in the Eternal City at the start of the seventeenth century, he was the most acclaimed religious painter in a city enflamed by Catholic renewal. The Sacrifice of Isaac reveals why he was commissioned to decorate sanctuaries: he could adopt a biblical story that had been portrayed many times before and render it so fresh, so unfiltered and physical that the horror seemed to be occurring directly in front of the spectator.

However there was a different side to Caravaggio, apparent as quickly as he arrived in the capital in the winter that ended the sixteenth century, as a painter in his initial twenties with no teacher or patron in the urban center, just skill and boldness. Most of the works with which he caught the holy metropolis's attention were everything but devout. What may be the very earliest resides in London's art museum. A young man parts his crimson lips in a scream of agony: while stretching out his filthy fingers for a fruit, he has rather been bitten. Boy Bitten By a Lizard is sensuality amid poverty: observers can discern Caravaggio's dismal room mirrored in the murky waters of the glass vase.

The adolescent sports a pink blossom in his coiffure – a emblem of the erotic commerce in Renaissance painting. Northern Italian painters such as Titian and Palma Vecchio depicted courtesans grasping flowers and, in a painting destroyed in the second world war but known through photographs, the master portrayed a renowned woman courtesan, holding a bouquet to her chest. The message of all these floral signifiers is obvious: intimacy for purchase.

How are we to make of the artist's erotic portrayals of youths – and of one boy in specific? It is a question that has split his interpreters ever since he achieved mega-fame in the twentieth century. The complex past truth is that the artist was not the queer icon that, for example, Derek Jarman presented on film in his twentieth-century movie Caravaggio, nor so completely pious that, as some art historians improbably assert, his Youth Holding Fruit is in fact a likeness of Christ.

His initial works indeed offer overt erotic suggestions, or including offers. It's as if Caravaggio, then a penniless youthful artist, identified with the city's prostitutes, offering himself to survive. In the Uffizi, with this thought in consideration, observers might turn to an additional early creation, the sixteenth-century masterpiece Bacchus, in which the deity of alcohol stares coolly at you as he begins to untie the dark sash of his garment.

A several annums following Bacchus, what could have motivated Caravaggio to paint Victorious Cupid for the art patron the nobleman, when he was at last growing almost respectable with important church projects? This unholy non-Christian deity revives the sexual provocations of his early works but in a increasingly powerful, uneasy way. Fifty years afterwards, its secret seemed obvious: it was a portrait of Caravaggio's companion. A British traveller saw Victorious Cupid in about the mid-seventeenth century and was told its subject has "the physique and countenance of [Caravaggio's|his] owne boy or servant that slept with him". The name of this adolescent was Cecco.

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