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A young lad cries out as his skull is firmly held, a large digit pressing into his cheek as his father's mighty hand grasps him by the throat. This moment from Abraham's Sacrifice appears in the Florentine museum, evoking distress through Caravaggio's harrowing portrayal of the suffering child from the biblical account. It appears as if Abraham, commanded by the Divine to sacrifice his son, could break his neck with a single turn. However the father's preferred method involves the metallic grey blade he holds in his remaining palm, ready to slit Isaac's neck. A definite aspect remains – whomever posed as the sacrifice for this astonishing work demonstrated remarkable expressive ability. Within exists not just dread, surprise and begging in his darkened eyes but additionally profound sorrow that a guardian could abandon him so utterly.

The artist took a well-known biblical story and made it so fresh and raw that its terrors appeared to happen right in front of you

Standing before the artwork, viewers recognize this as a actual countenance, an precise depiction of a young model, because the same youth – identifiable by his disheveled locks and almost dark pupils – features in two additional works by Caravaggio. In each case, that highly expressive visage dominates the composition. In John the Baptist, he gazes playfully from the shadows while embracing a ram. In Amor Vincit Omnia, he grins with a toughness acquired on Rome's streets, his black plumed wings demonic, a unclothed child running chaos in a affluent residence.

Amor Vincit Omnia, currently displayed at a London museum, constitutes one of the most discomfiting artworks ever painted. Observers feel totally unsettled looking at it. Cupid, whose darts fill people with frequently agonizing longing, is shown as a very tangible, brightly lit unclothed form, straddling toppled-over items that comprise musical devices, a musical manuscript, metal armour and an architect's ruler. This pile of possessions resembles, deliberately, the geometric and construction gear scattered across the floor in Albrecht Dürer's engraving Melencolia I – except here, the gloomy mess is created by this smirking Cupid and the turmoil he can unleash.

"Affection looks not with the eyes, but with the soul, / And therefore is winged Cupid depicted blind," penned Shakespeare, just before this painting was produced around 1601. But the painter's Cupid is not blind. He stares straight at the observer. That countenance – ironic and ruddy-cheeked, staring with bold confidence as he struts unclothed – is the identical one that screams in terror in Abraham's Test.

As the Italian master painted his three images of the same distinctive-looking youth in the Eternal City at the dawn of the 17th century, he was the highly acclaimed sacred painter in a city enflamed by Catholic revival. Abraham's Offering demonstrates why he was commissioned to decorate sanctuaries: he could take a scriptural story that had been depicted many occasions before and make it so new, so unfiltered and physical that the horror seemed to be occurring immediately in front of you.

Yet there was a different side to Caravaggio, apparent as soon as he arrived in Rome in the cold season that concluded the sixteenth century, as a artist in his initial 20s with no teacher or patron in the urban center, just skill and boldness. Most of the works with which he caught the sacred metropolis's eye were anything but holy. What may be the very first hangs in London's National Gallery. A youth opens his crimson mouth in a yell of agony: while stretching out his filthy digits for a fruit, he has rather been attacked. Boy Bitten By a Lizard is eroticism amid squalor: viewers can discern Caravaggio's dismal chamber mirrored in the cloudy liquid of the glass vase.

The boy wears a rose-colored flower in his hair – a emblem of the sex trade in early modern painting. Venetian painters such as Titian and Palma Vecchio depicted courtesans grasping flowers and, in a painting lost in the WWII but known through images, Caravaggio portrayed a renowned woman prostitute, holding a bouquet to her bosom. The message of all these botanical indicators is clear: intimacy for sale.

How are we to make of the artist's sensual portrayals of boys – and of one boy in particular? It is a question that has split his interpreters since he gained mega-fame in the 1980s. The complicated historical truth is that the painter was not the homosexual hero that, for instance, Derek Jarman put on screen in his 1986 film Caravaggio, nor so completely devout that, as some artistic scholars improbably assert, his Youth Holding Fruit is in fact a portrait of Christ.

His early works indeed make explicit sexual suggestions, or including propositions. It's as if Caravaggio, then a penniless youthful creator, identified with the city's sex workers, selling himself to live. In the Florentine gallery, with this thought in mind, viewers might turn to an additional early creation, the 1596 masterpiece Bacchus, in which the deity of alcohol gazes coolly at the spectator as he starts to undo the dark ribbon of his robe.

A several years following Bacchus, what could have motivated the artist to create Amor Vincit Omnia for the artistic collector Vincenzo Giustiniani, when he was finally becoming nearly established with important church commissions? This profane pagan deity revives the sexual challenges of his early paintings but in a increasingly powerful, uneasy way. Half a century later, its hidden meaning seemed obvious: it was a representation of Caravaggio's lover. A English traveller viewed Victorious Cupid in about 1649 and was told its figure has "the physique and countenance of [Caravaggio's|his] owne youth or assistant that laid with him". The name of this adolescent was Cecco.

The painter had been deceased for about 40 annums when this account was documented.