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The young lad cries out while his head is firmly gripped, a large digit pressing into his face as his father's mighty palm grasps him by the throat. This moment from Abraham's Sacrifice appears in the Florentine museum, evoking unease through the artist's chilling portrayal of the tormented youth from the biblical narrative. It appears as if the patriarch, instructed by God to sacrifice his offspring, could break his neck with a solitary twist. Yet the father's preferred method involves the silvery steel knife he holds in his other palm, prepared to cut the boy's throat. A certain element remains – whoever posed as Isaac for this astonishing work displayed extraordinary expressive skill. There exists not only dread, surprise and pleading in his shadowed eyes but additionally profound sorrow that a guardian could betray him so completely.

The artist adopted a well-known scriptural tale and made it so vibrant and raw that its horrors appeared to happen directly in front of the viewer

Viewing in front of the artwork, viewers recognize this as a real countenance, an accurate record of a young subject, because the same boy – identifiable by his disheveled hair and almost dark eyes – features in two other works by the master. In every case, that richly emotional face dominates the scene. In Youth With a Ram, he peers playfully from the darkness while holding a lamb. In Amor Vincit Omnia, he grins with a toughness acquired on Rome's streets, his black plumed appendages sinister, a naked child running chaos in a well-to-do residence.

Victorious Cupid, currently displayed at a British gallery, represents one of the most discomfiting masterpieces ever created. Observers feel totally unsettled looking at it. The god of love, whose arrows inspire people with frequently agonizing desire, is shown as a extremely real, vividly lit nude form, standing over overturned items that comprise stringed devices, a music manuscript, plate armor and an architect's ruler. This heap of possessions resembles, deliberately, the geometric and architectural equipment strewn across the floor in Albrecht Dürer's engraving Melancholy – save in this case, the gloomy mess is created by this smirking Cupid and the mayhem he can unleash.

"Love sees not with the eyes, but with the soul, / And thus is winged Love painted sightless," penned Shakespeare, shortly prior to this work was created around 1601. But the painter's god is not unseeing. He gazes straight at the observer. That countenance – sardonic and rosy-faced, looking with brazen assurance as he poses unclothed – is the identical one that screams in fear in Abraham's Test.

As the Italian master painted his three images of the identical unusual-looking kid in Rome at the start of the 17th century, he was the most celebrated religious painter in a metropolis ignited by religious revival. The Sacrifice of Isaac demonstrates why he was commissioned to decorate sanctuaries: he could adopt a scriptural story that had been portrayed numerous times before and render it so new, so unfiltered and visceral that the horror appeared to be happening immediately before you.

However there existed a different side to Caravaggio, apparent as soon as he came in the capital in the cold season that concluded 1592, as a artist in his initial twenties with no mentor or patron in the city, only skill and boldness. Most of the paintings with which he captured the sacred metropolis's attention were anything but devout. That may be the absolute first resides in the UK's National Gallery. A youth opens his crimson lips in a scream of agony: while reaching out his filthy digits for a fruit, he has instead been attacked. Youth Bitten by a Reptile is eroticism amid poverty: viewers can see Caravaggio's dismal chamber reflected in the cloudy liquid of the transparent vase.

The adolescent wears a pink flower in his coiffure – a symbol of the erotic trade in early modern art. Venetian artists such as Tiziano and Palma Vecchio depicted prostitutes grasping blooms and, in a work lost in the second world war but known through photographs, the master portrayed a renowned woman prostitute, holding a bouquet to her chest. The meaning of all these floral signifiers is clear: intimacy for purchase.

What are we to make of the artist's sensual portrayals of boys – and of one boy in particular? It is a inquiry that has divided his interpreters since he achieved mega-fame in the 1980s. The complex historical truth is that the artist was neither the queer icon that, for example, the filmmaker presented on film in his twentieth-century film about the artist, nor so entirely devout that, as some art scholars unbelievably assert, his Boy With a Basket of Fruit is in fact a portrait of Christ.

His initial works indeed make overt sexual suggestions, or including offers. It's as if the painter, then a penniless youthful artist, aligned with Rome's prostitutes, selling himself to survive. In the Florentine gallery, with this thought in consideration, viewers might turn to an additional early work, the sixteenth-century masterwork Bacchus, in which the god of alcohol gazes coolly at you as he starts to undo the black sash of his garment.

A several annums following the wine deity, what could have driven the artist to paint Victorious Cupid for the art collector the nobleman, when he was finally becoming almost respectable with important ecclesiastical commissions? This profane pagan deity resurrects the erotic challenges of his initial paintings but in a more powerful, unsettling way. Half a century later, its hidden meaning seemed obvious: it was a portrait of the painter's companion. A English visitor viewed Victorious Cupid in about 1649 and was told its subject has "the body & face of [Caravaggio's|his] owne boy or assistant that slept with him". The name of this adolescent was Francesco.

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