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The youthful boy cries out while his head is firmly gripped, a massive digit digging into his cheek as his father's powerful palm grasps him by the neck. That scene from Abraham's Sacrifice appears in the Uffizi Gallery, creating unease through Caravaggio's harrowing portrayal of the suffering child from the biblical narrative. The painting appears as if the patriarch, commanded by the Divine to kill his son, could break his neck with a solitary twist. However the father's preferred approach involves the silvery grey knife he holds in his remaining hand, ready to slit the boy's throat. One definite element stands out – whoever modeled as Isaac for this astonishing piece demonstrated remarkable expressive ability. Within exists not just dread, surprise and pleading in his shadowed gaze but also profound sorrow that a protector could betray him so completely.

The artist took a familiar biblical story and transformed it so fresh and visceral that its terrors seemed to unfold directly in view of the viewer

Viewing before the painting, viewers recognize this as a real face, an accurate record of a adolescent model, because the identical boy – identifiable by his tousled hair and nearly dark eyes – features in several other works by the master. In each case, that richly expressive visage dominates the scene. In Youth With a Ram, he gazes playfully from the shadows while holding a ram. In Victorious Cupid, he grins with a hardness learned on the city's alleys, his black feathery wings sinister, a naked adolescent running riot in a affluent dwelling.

Victorious Cupid, presently exhibited at a London museum, represents one of the most discomfiting artworks ever painted. Observers feel completely unsettled looking at it. The god of love, whose darts fill people with frequently painful desire, is portrayed as a very real, brightly lit nude form, standing over overturned items that include musical instruments, a musical score, metal armor and an builder's ruler. This heap of possessions echoes, deliberately, the geometric and construction equipment scattered across the floor in Albrecht Dürer's print Melencolia I – except here, the gloomy disorder is caused by this grinning Cupid and the turmoil he can release.

"Love looks not with the eyes, but with the soul, / And therefore is feathered Love painted sightless," wrote the Bard, shortly prior to this painting was produced around the early 1600s. But the painter's god is not unseeing. He stares directly at you. That face – sardonic and ruddy-cheeked, looking with bold confidence as he struts unclothed – is the identical one that shrieks in terror in The Sacrifice of Isaac.

As the Italian master painted his three portrayals of the same unusual-appearing kid in Rome at the start of the seventeenth century, he was the highly celebrated religious artist in a metropolis ignited by religious renewal. Abraham's Offering demonstrates why he was sought to decorate churches: he could adopt a scriptural narrative that had been portrayed many occasions before and render it so fresh, so unfiltered and visceral that the horror appeared to be occurring immediately in front of you.

However there existed another aspect to the artist, apparent as quickly as he arrived in Rome in the cold season that concluded the sixteenth century, as a painter in his early twenties with no mentor or patron in the urban center, only skill and boldness. The majority of the paintings with which he caught the sacred metropolis's eye were anything but holy. What may be the very first resides in London's art museum. A young man opens his red lips in a scream of pain: while reaching out his dirty digits for a fruit, he has rather been attacked. Youth Bitten by a Reptile is eroticism amid poverty: observers can discern Caravaggio's dismal chamber mirrored in the murky liquid of the glass container.

The boy sports a pink blossom in his hair – a symbol of the sex trade in early modern painting. Venetian artists such as Tiziano and Palma Vecchio portrayed prostitutes holding flowers and, in a work destroyed in the second world war but known through photographs, the master represented a famous female prostitute, clutching a posy to her bosom. The meaning of all these botanical indicators is obvious: intimacy for purchase.

What are we to make of the artist's sensual depictions of youths – and of a particular adolescent in particular? It is a inquiry that has split his interpreters ever since he gained widespread recognition in the twentieth century. The complex past truth is that the painter was neither the homosexual icon that, for example, the filmmaker put on screen in his 1986 film about the artist, nor so entirely devout that, as certain art historians improbably claim, his Youth Holding Fruit is actually a portrait of Jesus.

His initial paintings indeed offer overt sexual implications, or even offers. It's as if the painter, then a destitute young creator, aligned with the city's sex workers, offering himself to live. In the Florentine gallery, with this thought in mind, observers might look to an additional initial work, the sixteenth-century masterpiece Bacchus, in which the deity of wine gazes calmly at the spectator as he begins to undo the dark sash of his garment.

A several annums following the wine deity, what could have driven Caravaggio to paint Victorious Cupid for the art collector Vincenzo Giustiniani, when he was finally becoming almost established with important church projects? This unholy pagan deity resurrects the sexual provocations of his initial paintings but in a increasingly intense, uneasy manner. Half a century afterwards, its hidden meaning seemed clear: it was a representation of the painter's companion. A English traveller viewed Victorious Cupid in about 1649 and was informed its figure has "the physique and countenance of [Caravaggio's|his] own boy or servant that slept with him". The name of this boy was Francesco.

The artist had been deceased for about 40 years when this story was recorded.