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A youthful lad screams as his head is firmly held, a large thumb pressing into his cheek as his father's powerful hand holds him by the neck. This moment from Abraham's Sacrifice visits the Uffizi Gallery, evoking distress through the artist's harrowing rendition of the tormented youth from the scriptural narrative. The painting seems as if Abraham, instructed by the Divine to kill his offspring, could break his spinal column with a single turn. However the father's chosen method involves the silvery steel knife he holds in his other palm, prepared to cut the boy's throat. One definite element stands out – whoever modeled as the sacrifice for this breathtaking work displayed remarkable acting skill. Within exists not only dread, surprise and begging in his shadowed eyes but also deep sorrow that a guardian could abandon him so completely.

The artist adopted a well-known biblical tale and made it so fresh and visceral that its horrors appeared to unfold right in view of the viewer

Standing before the artwork, viewers recognize this as a actual face, an accurate record of a adolescent model, because the same youth – recognizable by his tousled locks and almost dark pupils – features in two additional paintings by the master. In each case, that highly expressive face commands the scene. In John the Baptist, he peers playfully from the shadows while holding a ram. In Victorious Cupid, he smirks with a toughness learned on the city's alleys, his black feathery appendages demonic, a unclothed adolescent running chaos in a well-to-do dwelling.

Victorious Cupid, currently exhibited at a London gallery, represents one of the most discomfiting artworks ever painted. Viewers feel completely unsettled gazing at it. Cupid, whose arrows fill people with often painful desire, is shown as a very tangible, vividly lit nude form, straddling overturned items that comprise musical instruments, a musical manuscript, plate armor and an architect's T-square. This pile of items echoes, deliberately, the mathematical and construction gear strewn across the floor in the German master's print Melancholy – except here, the melancholic mess is caused by this grinning Cupid and the mayhem he can release.

"Affection sees not with the vision, but with the mind, / And thus is feathered Cupid painted sightless," wrote the Bard, shortly prior to this work was created around 1601. But the painter's Cupid is not blind. He stares directly at you. That face – ironic and rosy-faced, staring with bold assurance as he struts naked – is the same one that screams in fear in Abraham's Test.

As the Italian master painted his three images of the identical distinctive-looking kid in Rome at the start of the seventeenth century, he was the highly acclaimed religious painter in a metropolis enflamed by Catholic revival. Abraham's Offering reveals why he was sought to decorate churches: he could take a biblical story that had been depicted numerous occasions before and make it so fresh, so raw and physical that the terror seemed to be occurring immediately before you.

Yet there was a different aspect to Caravaggio, evident as soon as he came in the capital in the winter that concluded the sixteenth century, as a painter in his early twenties with no mentor or supporter in the urban center, only skill and audacity. Most of the works with which he caught the holy metropolis's eye were everything but holy. That could be the absolute first hangs in London's art museum. A young man opens his red mouth in a yell of agony: while stretching out his dirty digits for a fruit, he has instead been bitten. Youth Bitten by a Reptile is sensuality amid squalor: observers can discern Caravaggio's dismal room mirrored in the murky liquid of the transparent container.

The boy wears a pink flower in his hair – a symbol of the sex commerce in early modern painting. Venetian painters such as Titian and Palma Vecchio depicted prostitutes holding blooms and, in a painting destroyed in the WWII but documented through photographs, Caravaggio portrayed a famous female courtesan, holding a posy to her chest. The meaning of all these floral indicators is clear: intimacy for purchase.

How are we to interpret of the artist's erotic portrayals of boys – and of one boy in particular? It is a question that has divided his commentators ever since he gained mega-fame in the twentieth century. The complex historical truth is that the artist was neither the homosexual icon that, for example, Derek Jarman put on screen in his twentieth-century film Caravaggio, nor so completely pious that, as some artistic historians improbably claim, his Youth Holding Fruit is in fact a likeness of Jesus.

His initial works do make overt erotic suggestions, or including propositions. It's as if the painter, then a destitute youthful creator, identified with Rome's sex workers, selling himself to live. In the Florentine gallery, with this thought in mind, observers might turn to another early creation, the 1596 masterwork the god of wine, in which the god of wine gazes coolly at the spectator as he begins to undo the black sash of his robe.

A several annums following the wine deity, what could have motivated Caravaggio to paint Amor Vincit Omnia for the artistic patron the nobleman, when he was at last becoming nearly established with prestigious ecclesiastical projects? This profane non-Christian deity resurrects the sexual provocations of his early works but in a more intense, uneasy way. Half a century later, its secret seemed clear: it was a portrait of the painter's companion. A English visitor viewed Victorious Cupid in about the mid-seventeenth century and was informed its subject 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 artist had been deceased for about 40 annums when this story was recorded.