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A youthful boy screams while his head is forcefully held, a massive thumb pressing into his face as his parent's powerful palm grasps him by the throat. That moment from The Sacrifice of Isaac appears in the Florentine museum, creating distress through the artist's chilling rendition of the tormented youth from the biblical account. The painting seems as if Abraham, commanded by the Divine to kill his offspring, could snap his spinal column with a solitary twist. Yet Abraham's chosen method involves the metallic steel blade he grips in his remaining hand, ready to slit the boy's throat. A certain element stands out – whomever modeled as the sacrifice for this astonishing piece displayed extraordinary acting ability. Within exists not only fear, surprise and pleading in his darkened gaze but also deep grief that a guardian could abandon him so completely.

He took a familiar scriptural tale and made it so fresh and raw that its terrors seemed to unfold directly in view of the viewer

Viewing before the artwork, viewers recognize this as a actual face, an precise record of a adolescent model, because the same boy – recognizable by his tousled locks and nearly black eyes – appears in two other works by Caravaggio. In each case, that highly emotional face dominates the scene. In Youth With a Ram, he gazes mischievously from the darkness while embracing a ram. In Amor Vincit Omnia, he smirks with a toughness learned on the city's streets, his black feathery appendages demonic, a naked adolescent running chaos in a well-to-do dwelling.

Amor Vincit Omnia, presently displayed at a British gallery, represents one of the most embarrassing masterpieces ever painted. Viewers feel totally disoriented gazing at it. Cupid, whose arrows inspire people with often agonizing longing, is shown as a extremely real, vividly lit nude form, standing over overturned objects that comprise stringed instruments, a music manuscript, metal armour and an builder's T-square. This pile of possessions resembles, intentionally, the geometric and architectural equipment strewn across the ground in Albrecht Dürer's print Melencolia I – except in this case, the gloomy mess is caused by this smirking deity and the turmoil he can release.

"Affection looks not with the vision, but with the soul, / And therefore is feathered Cupid depicted blind," penned Shakespeare, just before this work was produced around the early 1600s. But the painter's Cupid is not blind. He stares directly at you. That face – sardonic and ruddy-faced, looking with brazen confidence as he poses unclothed – is the same one that shrieks in terror in Abraham's Test.

As Michelangelo Merisi da Caravaggio painted his three images of the same unusual-looking kid in the Eternal City at the start of the seventeenth century, he was the most acclaimed sacred painter in a metropolis enflamed by religious revival. Abraham's Offering demonstrates why he was commissioned to adorn churches: he could adopt a scriptural story that had been portrayed many times before and make it so new, so unfiltered and visceral that the terror appeared to be occurring immediately before you.

However there was another aspect to the artist, apparent as quickly as he came in the capital in the winter that concluded 1592, as a painter in his early twenties with no mentor or supporter in the urban center, just skill and boldness. The majority of the paintings with which he caught the sacred metropolis's attention were anything but holy. That may be the absolute first resides in London's art museum. A young man parts his crimson lips in a yell of agony: while reaching out his dirty digits for a cherry, he has instead been attacked. Boy Bitten By a Lizard is eroticism amid poverty: viewers can discern the painter's dismal room reflected in the cloudy liquid of the glass vase.

The boy sports a pink blossom in his coiffure – a emblem of the sex commerce in early modern art. Venetian painters such as Titian and Palma Vecchio portrayed prostitutes grasping blooms and, in a work destroyed in the WWII but known through photographs, Caravaggio represented a renowned female courtesan, holding a posy to her chest. The message of all these botanical signifiers is obvious: sex for sale.

What are we to make of the artist's erotic portrayals of youths – and of one adolescent in particular? It is a question that has split his interpreters since he achieved mega-fame in the twentieth century. The complicated historical truth is that the painter was neither the queer hero that, for instance, Derek Jarman presented on film in his 1986 movie about the artist, nor so entirely pious that, as some art scholars unbelievably claim, his Boy With a Basket of Fruit is in fact a likeness of Christ.

His early works indeed offer overt erotic implications, or including offers. It's as if the painter, then a destitute young creator, identified with Rome's sex workers, selling himself to live. In the Florentine gallery, with this idea in consideration, viewers might turn to an additional initial work, the sixteenth-century masterpiece Bacchus, in which the deity of wine stares coolly at the spectator as he starts to undo the dark sash of his garment.

A few years after Bacchus, what could have motivated Caravaggio to paint Victorious Cupid for the artistic patron the nobleman, when he was at last growing nearly established with prestigious church projects? This profane non-Christian deity revives the erotic provocations of his early paintings but in a more powerful, unsettling way. Fifty years afterwards, its secret seemed obvious: it was a representation of Caravaggio's lover. A English visitor saw Victorious Cupid in about the mid-seventeenth century and was told its subject has "the physique and countenance of [Caravaggio's|his] own youth or servant that slept with him". The identity of this boy was Cecco.

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