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A youthful lad screams while his skull is firmly held, a large thumb pressing into his cheek as his parent's powerful palm grasps him by the throat. That moment from The Sacrifice of Isaac visits the Florentine museum, creating unease through the artist's harrowing portrayal of the tormented child from the biblical account. It appears as if Abraham, commanded by the Divine to sacrifice his offspring, could break his neck with a single twist. Yet the father's preferred approach involves the metallic grey knife he grips in his remaining palm, ready to slit the boy's neck. One definite aspect stands out – whomever modeled as the sacrifice for this breathtaking work demonstrated extraordinary expressive skill. Within exists not just dread, shock and pleading in his darkened eyes but also profound grief that a protector could abandon him so utterly.

The artist took a familiar scriptural story and transformed it so fresh and visceral that its terrors appeared to happen right in view of you

Viewing before the artwork, viewers recognize this as a actual countenance, an accurate depiction of a adolescent subject, because the identical boy – identifiable by his disheveled locks and almost dark pupils – appears in two other works by Caravaggio. In each instance, that highly emotional visage commands the scene. In Youth With a Ram, he gazes playfully from the darkness while embracing a lamb. In Amor Vincit Omnia, he grins with a hardness learned on Rome's alleys, his black plumed wings sinister, a naked adolescent running chaos in a affluent residence.

Victorious Cupid, presently exhibited at a London gallery, constitutes one of the most discomfiting masterpieces ever painted. Observers feel completely unsettled looking at it. Cupid, whose arrows inspire people with often agonizing longing, is portrayed as a very tangible, brightly lit unclothed figure, standing over toppled-over objects that include musical devices, a music score, plate armor and an architect's ruler. This heap of items resembles, deliberately, the mathematical and construction equipment scattered across the ground in Albrecht Dürer's print Melancholy – save here, the gloomy mess is caused by this grinning Cupid and the mayhem he can release.

"Love looks not with the eyes, but with the mind, / And thus is winged Love painted blind," wrote the Bard, shortly prior to this painting was produced around 1601. But the painter's god is not unseeing. He stares directly at you. That face – sardonic and rosy-cheeked, looking with bold assurance as he struts naked – is the same one that shrieks in terror in The Sacrifice of Isaac.

As Michelangelo Merisi da Caravaggio created his multiple portrayals of the identical distinctive-appearing youth in Rome at the start of the 17th century, he was the highly acclaimed religious painter in a metropolis ignited by religious renewal. The Sacrifice of Isaac demonstrates why he was commissioned to adorn churches: he could take a biblical narrative that had been portrayed numerous times previously and make it so new, so unfiltered and physical that the terror seemed to be happening immediately in front of the spectator.

Yet there was another side to Caravaggio, evident as soon as he came in the capital in the cold season that ended 1592, as a painter in his initial twenties with no mentor or patron in the urban center, only talent and audacity. The majority of the paintings with which he captured the holy metropolis's eye were anything but holy. That could be the absolute first resides in London's art museum. A youth parts his red lips in a scream of pain: while stretching out his dirty digits for a cherry, he has instead been attacked. Youth Bitten by a Reptile is eroticism amid poverty: observers can discern the painter's dismal chamber reflected in the cloudy liquid of the glass vase.

The adolescent sports a rose-colored blossom in his hair – a symbol of the sex commerce in Renaissance painting. Northern Italian painters such as Tiziano and Palma Vecchio depicted courtesans grasping flowers and, in a painting destroyed in the second world war but documented through images, Caravaggio portrayed a famous woman prostitute, holding a posy to her bosom. The meaning of all these botanical indicators is obvious: sex for purchase.

How are we to make of Caravaggio's erotic depictions of boys – and of one boy in particular? It is a question that has split his interpreters since he achieved mega-fame in the twentieth century. The complicated historical reality is that the artist was not the queer icon that, for example, Derek Jarman put on film in his twentieth-century movie Caravaggio, nor so entirely pious that, as some artistic historians improbably claim, his Boy With a Basket of Fruit is in fact a portrait of Jesus.

His early paintings indeed make overt erotic implications, or even propositions. It's as if Caravaggio, then a penniless youthful artist, identified with Rome's sex workers, selling himself to survive. In the Uffizi, with this thought in consideration, viewers might turn to an additional initial work, the sixteenth-century masterwork Bacchus, in which the god of alcohol gazes coolly at the spectator as he begins to untie the black sash of his robe.

A few annums after the wine deity, what could have motivated the artist to create Victorious Cupid for the art patron the nobleman, when he was finally growing almost established with important church projects? This profane pagan deity resurrects the sexual challenges of his early works but in a more powerful, unsettling way. Fifty years afterwards, its hidden meaning seemed obvious: it was a representation of Caravaggio's companion. A British visitor saw the painting in about 1649 and was told its subject has "the body & face of [Caravaggio's|his] owne boy or servant that slept with him". The name of this boy was Cecco.

The painter had been dead for about forty years when this story was documented.