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The young lad screams as his head is forcefully gripped, a large digit digging into his face as his parent's powerful hand grasps him by the neck. This moment from Abraham's Sacrifice visits the Florentine museum, evoking unease through the artist's harrowing rendition of the suffering child from the scriptural account. The painting appears as if Abraham, instructed by the Divine to sacrifice his offspring, could break his neck with a solitary turn. Yet Abraham's chosen approach involves the metallic steel blade he grips in his other palm, ready to slit Isaac's throat. One certain element stands out – whoever modeled as the sacrifice for this astonishing work displayed extraordinary expressive ability. There exists not only fear, shock and begging in his darkened gaze but additionally profound sorrow that a guardian could abandon him so completely.

The artist adopted a well-known scriptural tale and made it so fresh and visceral that its horrors appeared to happen right in view of you

Viewing in front of the painting, observers identify this as a real countenance, an precise depiction of a adolescent model, because the same boy – recognizable by his disheveled locks and nearly black eyes – features in two other works by Caravaggio. In each case, that richly emotional face dominates the composition. In Youth With a Ram, he gazes playfully from the darkness while embracing a lamb. In Amor Vincit Omnia, he grins with a toughness acquired on Rome's streets, his dark feathery wings sinister, a naked child creating riot in a well-to-do dwelling.

Amor Vincit Omnia, currently exhibited at a British museum, represents one of the most discomfiting masterpieces ever painted. Observers feel completely unsettled looking at it. The god of love, whose arrows inspire people with frequently painful desire, is shown as a extremely real, brightly lit nude form, straddling overturned objects that include stringed instruments, a musical manuscript, metal armor and an architect's T-square. This heap of possessions echoes, deliberately, the geometric and architectural equipment scattered across the ground in Albrecht Dürer's print Melancholy – except in this case, the gloomy mess is created by this smirking deity and the mayhem he can unleash.

"Affection sees not with the eyes, but with the mind, / And thus is winged Love painted sightless," wrote Shakespeare, just before this painting was produced around 1601. But Caravaggio's Cupid is not blind. He gazes directly at you. That countenance – sardonic and rosy-faced, looking with brazen confidence as he struts unclothed – is the same one that shrieks in terror in Abraham's Test.

As Michelangelo Merisi da Caravaggio created his multiple portrayals of the same distinctive-looking kid in Rome at the dawn of the 17th century, he was the highly celebrated sacred artist in a city ignited by religious revival. Abraham's Offering demonstrates why he was commissioned to adorn sanctuaries: he could adopt a biblical narrative that had been depicted many occasions previously and make it so new, so raw and visceral that the horror appeared to be happening immediately before the spectator.

However there existed another aspect to the artist, evident as quickly as he came in Rome in the winter that concluded 1592, as a painter in his early 20s with no teacher or patron in the city, just talent and boldness. The majority of the works with which he caught the sacred metropolis's attention were anything but holy. What could be the absolute earliest hangs in London's art museum. A youth opens his red mouth in a yell of agony: while reaching out his dirty digits for a fruit, he has instead been bitten. Youth Bitten by a Reptile is eroticism amid poverty: viewers can see Caravaggio's dismal chamber reflected in the murky liquid of the glass vase.

The boy wears a rose-colored blossom in his coiffure – a symbol of the sex commerce in early modern art. Venetian artists such as Titian and Palma Vecchio depicted prostitutes holding blooms and, in a painting destroyed in the WWII but known through photographs, the master represented a famous female courtesan, holding a posy to her chest. The meaning of all these botanical signifiers is obvious: sex for purchase.

What are we to make of Caravaggio's erotic depictions of youths – and of a particular adolescent in particular? It is a question that has split his commentators since he gained widespread recognition in the 1980s. The complex historical reality is that the artist was neither the homosexual icon that, for example, Derek Jarman put on film in his 1986 film about the artist, nor so entirely devout that, as some art scholars unbelievably claim, his Boy With a Basket of Fruit is in fact a portrait of Christ.

His early works do make explicit sexual implications, or even propositions. It's as if the painter, then a penniless youthful artist, aligned with the city's sex workers, selling himself to live. In the Florentine gallery, with this thought in mind, observers might look to an additional early work, the sixteenth-century masterpiece the god of wine, in which the god of wine stares coolly at you as he begins to undo the black sash of his garment.

A few years following the wine deity, what could have driven Caravaggio to paint Amor Vincit Omnia for the artistic collector Vincenzo Giustiniani, when he was at last becoming nearly established with prestigious ecclesiastical projects? This profane pagan deity revives the sexual provocations of his initial works but in a more intense, unsettling manner. Half a century later, its hidden meaning seemed obvious: it was a portrait of Caravaggio's lover. A British traveller saw the painting in about 1649 and was informed its subject has "the body & face of [Caravaggio's|his] own boy or servant that laid with him". The identity of this adolescent was Francesco.

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