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A youthful boy cries out as his head is firmly held, a large digit digging into his face as his parent's powerful hand grasps him by the throat. This moment from The Sacrifice of Isaac appears in the Uffizi Gallery, creating distress through Caravaggio's harrowing rendition of the tormented youth from the biblical narrative. It appears as if the patriarch, instructed by the Divine to sacrifice his offspring, could break his neck with a solitary turn. Yet Abraham's preferred approach involves the silvery steel knife he grips in his remaining palm, prepared to slit Isaac's throat. One definite aspect remains – whomever modeled as the sacrifice for this breathtaking piece demonstrated remarkable expressive skill. Within exists not only dread, shock and pleading in his shadowed eyes but also profound grief that a protector could betray him so completely.

He adopted a well-known scriptural story and transformed it so fresh and raw that its horrors seemed to happen right in front of you

Viewing in front of the artwork, observers recognize this as a real face, an precise depiction of a adolescent model, because the same boy – recognizable by his tousled hair and almost black pupils – features in several other paintings by the master. In every instance, that highly expressive visage commands the composition. In Youth With a Ram, he gazes mischievously from the shadows while embracing a ram. In Amor Vincit Omnia, he smirks with a hardness acquired on the city's alleys, his dark feathery appendages sinister, a unclothed child creating riot in a well-to-do dwelling.

Amor Vincit Omnia, presently exhibited at a London gallery, constitutes one of the most embarrassing masterpieces ever painted. Observers feel completely disoriented gazing at it. Cupid, whose darts inspire people with frequently painful desire, is shown as a extremely real, brightly lit nude figure, standing over toppled-over items that comprise musical instruments, a music score, metal armor and an builder's T-square. This pile of possessions resembles, deliberately, the mathematical and architectural gear strewn across the ground in the German master's print Melencolia I – except in this case, the gloomy mess is caused by this grinning deity and the turmoil he can unleash.

"Affection looks not with the vision, but with the mind, / And therefore is feathered Love painted blind," wrote Shakespeare, just before this painting was created around 1601. But the painter's god is not unseeing. He stares directly at the observer. That countenance – sardonic and ruddy-cheeked, staring with bold assurance as he struts unclothed – is the same one that screams in terror in Abraham's Test.

As the Italian master painted his multiple portrayals of the identical distinctive-looking kid in Rome at the start of the 17th century, he was the most celebrated sacred painter in a metropolis enflamed by Catholic revival. Abraham's Offering reveals why he was sought to decorate churches: he could take a biblical narrative that had been portrayed many times before and render it so fresh, so unfiltered and visceral that the terror seemed to be occurring immediately before the spectator.

However there existed a different side to the artist, apparent as quickly as he came in the capital in the winter that concluded the sixteenth century, as a artist in his initial twenties with no teacher or supporter in the city, only skill and audacity. The majority of the works with which he captured the sacred metropolis's attention were anything but holy. What may be the absolute first resides in London's National Gallery. A young man parts his crimson lips in a scream of pain: while stretching out his filthy fingers for a cherry, he has instead been bitten. Boy Bitten By a Lizard is sensuality amid poverty: observers can discern Caravaggio's dismal room mirrored in the cloudy waters of the glass container.

The adolescent sports a rose-colored flower in his coiffure – a symbol of the sex trade in early modern painting. Venetian artists such as Titian and Palma Vecchio depicted courtesans grasping blooms and, in a work destroyed in the second world war but known through photographs, the master represented a renowned woman prostitute, holding a bouquet to her chest. The meaning of all these botanical indicators is clear: intimacy for purchase.

What are we to make of the artist's erotic portrayals of boys – and of a particular adolescent in particular? It is a question that has divided his interpreters ever since he gained mega-fame in the 1980s. The complicated past truth is that the artist was neither the queer icon that, for instance, the filmmaker put on film in his twentieth-century movie Caravaggio, nor so entirely devout that, as some artistic scholars unbelievably claim, his Youth Holding Fruit is in fact a likeness of Christ.

His initial works do offer overt sexual suggestions, or even propositions. It's as if Caravaggio, then a penniless youthful artist, identified with Rome's prostitutes, offering himself to live. In the Florentine gallery, with this thought in consideration, viewers might look to an additional early work, the 1596 masterpiece Bacchus, in which the god of wine stares coolly at you as he starts to undo the dark sash of his robe.

A several annums following the wine deity, what could have motivated the artist to create Amor Vincit Omnia for the artistic collector Vincenzo Giustiniani, when he was finally growing nearly established with important church projects? This unholy non-Christian god resurrects the erotic provocations of his early paintings but in a increasingly powerful, uneasy way. Half a century later, its hidden meaning seemed clear: it was a portrait of Caravaggio's companion. A British visitor saw the painting in about 1649 and was told its figure has "the physique and countenance of [Caravaggio's|his] own boy or assistant that laid with him". The name of this adolescent was Cecco.

The painter had been dead for about 40 years when this story was recorded.