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A youthful lad cries out while his skull is firmly held, a massive digit pressing into his face as his parent's mighty palm holds him by the throat. This moment from The Sacrifice of Isaac appears in the Florentine museum, creating unease through the artist's harrowing portrayal of the tormented youth from the biblical account. It appears as if Abraham, commanded by the Divine to sacrifice his son, could break his neck with a single twist. Yet Abraham's chosen method involves the metallic grey blade he grips in his other hand, prepared to slit the boy's neck. One certain element remains – whomever modeled as Isaac for this astonishing piece displayed remarkable acting ability. Within exists not just fear, shock and pleading in his darkened eyes but also deep grief that a guardian could betray him so utterly.

The artist adopted a familiar scriptural story and transformed it so fresh and raw that its terrors seemed to unfold right in front of you

Viewing in front of the artwork, viewers recognize this as a real countenance, an precise record of a adolescent model, because the same boy – identifiable by his disheveled locks and almost dark eyes – features in several other paintings by Caravaggio. In each case, that richly emotional face dominates the scene. In John the Baptist, he peers playfully from the darkness while embracing a ram. In Amor Vincit Omnia, he grins with a toughness learned on the city's streets, his black plumed appendages demonic, a naked adolescent running chaos in a well-to-do dwelling.

Amor Vincit Omnia, presently displayed at a London gallery, constitutes one of the most discomfiting artworks ever created. Viewers feel totally unsettled gazing at it. Cupid, whose darts inspire people with frequently painful longing, is shown as a extremely tangible, vividly lit unclothed form, straddling toppled-over objects that comprise stringed devices, a music manuscript, plate armor and an builder's ruler. This pile of possessions resembles, intentionally, the mathematical and architectural gear scattered across the ground in the German master's print Melancholy – except in this case, the gloomy disorder is caused by this smirking deity and the turmoil he can unleash.

"Affection looks not with the eyes, but with the soul, / And therefore is winged Cupid depicted blind," penned the Bard, just before this work was created around the early 1600s. But Caravaggio's Cupid is not blind. He stares directly at you. That countenance – ironic and rosy-faced, staring with bold confidence as he poses naked – is the identical one that screams in terror in Abraham's Test.

As Michelangelo Merisi da Caravaggio painted his three portrayals of the same distinctive-appearing kid in the Eternal City at the start of the seventeenth century, he was the most celebrated sacred painter in a metropolis ignited by religious revival. The Sacrifice of Isaac reveals why he was commissioned to adorn churches: he could take a biblical story that had been portrayed many times before and render it so new, so unfiltered and physical that the terror seemed to be happening directly before the spectator.

Yet there existed another aspect to Caravaggio, apparent as soon as he came in the capital in the cold season that ended the sixteenth century, as a artist in his early twenties with no mentor or patron in the urban center, just talent and audacity. Most of the paintings with which he caught the sacred metropolis's attention were everything but devout. That could be the absolute earliest resides in London's National Gallery. A young man parts his crimson mouth in a scream of agony: while stretching out his dirty fingers for a cherry, he has instead been bitten. Youth Bitten by a Reptile is sensuality amid squalor: viewers can see the painter's dismal room reflected in the murky liquid of the glass vase.

The boy sports a pink flower in his hair – a symbol of the sex trade in early modern painting. Northern Italian artists such as Titian and Jacopo Palma depicted courtesans grasping flowers and, in a painting destroyed in the WWII but known through images, the master portrayed a renowned female courtesan, holding a bouquet to her bosom. The message of all these floral indicators is obvious: intimacy for sale.

How are we to make of Caravaggio's sensual depictions of boys – and of a particular adolescent in specific? It is a question that has divided his interpreters since he achieved mega-fame in the 1980s. The complicated past reality is that the artist was not the queer icon that, for instance, the filmmaker put on screen in his 1986 movie Caravaggio, nor so entirely devout that, as certain artistic historians improbably assert, his Youth Holding Fruit is in fact a portrait of Christ.

His initial works do offer explicit sexual implications, or including propositions. It's as if the painter, then a penniless youthful creator, aligned with the city's sex workers, offering himself to survive. In the Florentine gallery, with this idea in consideration, observers might look to an additional initial work, the sixteenth-century masterwork Bacchus, in which the god of wine stares calmly at you as he begins to untie the dark ribbon of his garment.

A several years after Bacchus, what could have driven Caravaggio to paint Victorious Cupid for the artistic patron the nobleman, when he was finally becoming nearly established with prestigious church commissions? This unholy non-Christian god resurrects the sexual challenges of his early works but in a more powerful, uneasy manner. Fifty years later, its secret seemed obvious: it was a portrait of Caravaggio's companion. A British visitor viewed the painting in about 1649 and was informed its subject has "the body & face of [Caravaggio's|his] owne boy or assistant that laid with him". The identity of this boy was Francesco.

The artist had been deceased for about forty years when this account was documented.