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The youthful boy cries out while his skull is forcefully held, a massive thumb digging into his face as his parent's mighty palm grasps him by the neck. That scene from Abraham's Sacrifice appears in the Uffizi Gallery, evoking unease through the artist's harrowing portrayal of the tormented youth from the biblical account. It appears as if the patriarch, commanded by the Divine to sacrifice his offspring, could snap his neck with a single twist. However Abraham's preferred approach involves the metallic steel blade he holds in his remaining palm, ready to cut the boy's throat. One definite aspect remains – whoever posed as Isaac for this breathtaking piece demonstrated remarkable acting ability. Within exists not only fear, shock and begging in his darkened eyes but additionally profound grief that a guardian could abandon him so completely.

The artist adopted a well-known biblical tale and made it so fresh and visceral that its terrors seemed to unfold directly in view of the viewer

Standing before the artwork, viewers identify this as a actual face, an precise record of a adolescent subject, because the same boy – identifiable by his tousled locks and nearly dark pupils – appears in several additional works by Caravaggio. In each instance, that highly expressive visage commands the scene. In John the Baptist, he gazes playfully from the darkness while holding a ram. In Amor Vincit Omnia, he grins with a hardness acquired on the city's alleys, his dark feathery appendages sinister, a unclothed child creating chaos in a well-to-do residence.

Amor Vincit Omnia, currently exhibited at a London gallery, represents one of the most embarrassing artworks ever created. Observers feel totally disoriented gazing at it. Cupid, whose darts inspire people with often painful longing, is shown as a extremely tangible, vividly lit unclothed form, standing over toppled-over items that include stringed devices, a music score, plate armour and an builder's ruler. This pile of possessions echoes, deliberately, the mathematical and construction equipment scattered across the ground in Albrecht Dürer's engraving Melancholy – save here, the gloomy disorder is caused by this grinning Cupid and the turmoil he can release.

"Affection looks not with the vision, but with the mind, / And thus is feathered Love depicted sightless," wrote the Bard, shortly prior to this painting was created around 1601. But Caravaggio's Cupid is not unseeing. He gazes directly at you. That countenance – ironic and ruddy-cheeked, looking with bold assurance as he struts unclothed – is the same one that screams in fear in The Sacrifice of Isaac.

When Michelangelo Merisi da Caravaggio painted his multiple images of the identical unusual-appearing youth in the Eternal City at the dawn of the seventeenth century, he was the highly celebrated religious artist in a city enflamed by Catholic renewal. The Sacrifice of Isaac reveals why he was commissioned to adorn churches: he could adopt a biblical narrative that had been portrayed numerous occasions before and make it so fresh, so unfiltered and visceral that the terror seemed to be occurring directly before you.

However there existed another aspect to the artist, apparent as quickly as he came in Rome in the cold season that ended 1592, as a painter in his initial twenties with no teacher or supporter in the city, only skill and audacity. Most of the paintings with which he captured the holy metropolis's attention were everything but devout. What could be the very earliest resides in London's National Gallery. A youth opens his crimson lips in a yell of pain: while reaching out his dirty fingers for a cherry, he has rather been attacked. Youth Bitten by a Reptile is eroticism amid poverty: viewers can see the painter's dismal chamber mirrored in the murky liquid of the glass vase.

The adolescent wears a rose-colored flower in his hair – a symbol of the erotic commerce in Renaissance art. Northern Italian artists such as Titian and Jacopo Palma portrayed prostitutes holding blooms and, in a work destroyed in the second world war but known through images, Caravaggio represented a famous woman courtesan, clutching a bouquet to her bosom. The message of all these floral signifiers is obvious: intimacy for sale.

How are we to make of the artist's erotic depictions of boys – and of a particular adolescent in specific? It is a question that has divided his commentators ever since he achieved widespread recognition in the 1980s. The complicated past truth is that the painter was not the homosexual hero that, for instance, Derek Jarman presented on film in his 1986 film Caravaggio, nor so entirely devout that, as certain artistic historians improbably assert, his Youth Holding Fruit is in fact a likeness of Jesus.

His early paintings do make explicit sexual implications, or even offers. It's as if Caravaggio, then a destitute young creator, aligned with the city's sex workers, offering himself to survive. In the Florentine gallery, with this thought in consideration, observers might turn to an additional initial creation, the 1596 masterwork Bacchus, in which the god of alcohol gazes coolly at the spectator as he starts to untie the dark ribbon of his garment.

A few annums following the wine deity, what could have motivated the artist to paint Amor Vincit Omnia for the art collector Vincenzo Giustiniani, when he was finally becoming almost respectable with important church commissions? This unholy non-Christian deity resurrects the sexual challenges of his initial paintings but in a increasingly intense, uneasy manner. Fifty years afterwards, its secret seemed clear: it was a representation of Caravaggio's companion. A British visitor viewed Victorious Cupid in about the mid-seventeenth century and was told its subject has "the body & face of [Caravaggio's|his] owne youth or servant that slept with him". The name of this adolescent was Cecco.

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