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A young boy cries out as his head is forcefully gripped, a massive thumb digging into his cheek as his parent's powerful palm grasps him by the neck. This scene from Abraham's Sacrifice appears in the Florentine museum, evoking distress through the artist's harrowing portrayal of the tormented youth from the biblical narrative. The painting seems as if Abraham, instructed by God to kill his son, could snap his neck with a single twist. Yet Abraham's chosen approach involves the metallic steel blade he holds in his remaining palm, ready to cut Isaac's neck. A certain element stands out – whoever posed as the sacrifice for this breathtaking work demonstrated remarkable acting skill. Within exists not only dread, shock and pleading in his darkened eyes but also deep sorrow that a guardian could abandon him so completely.

He took a well-known biblical story and made it so fresh and visceral that its terrors appeared to unfold right in front of you

Standing in front of the painting, observers recognize this as a actual countenance, an precise record of a adolescent subject, because the same youth – recognizable by his disheveled hair and almost dark pupils – appears in two other paintings by the master. In every instance, that highly expressive visage dominates the composition. In Youth With a Ram, he peers playfully from the darkness while holding a lamb. In Amor Vincit Omnia, he grins with a hardness learned on the city's alleys, his black feathery wings demonic, a naked child creating chaos in a well-to-do residence.

Amor Vincit Omnia, currently exhibited at a London museum, represents one of the most discomfiting artworks ever painted. Viewers feel totally disoriented looking at it. The god of love, whose arrows inspire people with often painful longing, is shown as a extremely real, brightly illuminated unclothed figure, standing over overturned objects that comprise musical devices, a music score, plate armour and an architect's ruler. This heap of items echoes, intentionally, the mathematical and architectural gear strewn across the floor in the German master's engraving Melencolia I – except here, the melancholic disorder is created by this smirking Cupid and the turmoil he can unleash.

"Affection sees not with the vision, but with the soul, / And therefore is feathered Love painted blind," wrote the Bard, just prior to this work was created around 1601. But Caravaggio's god is not unseeing. He gazes straight at the observer. That face – sardonic and ruddy-cheeked, looking with brazen confidence as he poses naked – is the identical one that shrieks in fear in Abraham's Test.

When Michelangelo Merisi da Caravaggio painted his multiple portrayals of the identical distinctive-looking kid in the Eternal City at the dawn of the 17th century, he was the most celebrated religious artist in a city enflamed by Catholic renewal. The Sacrifice of Isaac reveals why he was sought to adorn sanctuaries: he could adopt a scriptural story that had been depicted many occasions before and render it so new, so raw and physical that the terror seemed to be happening immediately before the spectator.

Yet there existed a different aspect to the artist, evident as soon as he arrived in the capital in the winter that ended the sixteenth century, as a painter in his initial 20s with no mentor or supporter in the city, just skill and boldness. The majority 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 art museum. A youth parts his red lips in a yell of pain: while reaching out his filthy digits for a cherry, he has rather been bitten. Youth Bitten by a Reptile is sensuality amid poverty: observers can see the painter's gloomy room mirrored in the cloudy waters of the transparent container.

The boy sports a rose-colored blossom in his hair – a symbol of the erotic trade in Renaissance painting. Venetian artists such as Titian and Jacopo Palma portrayed courtesans holding flowers and, in a painting lost in the WWII but known through photographs, Caravaggio represented a famous female prostitute, holding a bouquet to her chest. The message of all these botanical indicators is clear: intimacy for purchase.

What are we to interpret of Caravaggio's erotic depictions of boys – and of one boy in specific? It is a question that has split his commentators ever since he achieved widespread recognition in the twentieth century. The complicated past reality is that the painter was not the homosexual icon that, for instance, the filmmaker presented on screen in his twentieth-century film about the artist, nor so completely pious that, as some artistic scholars improbably claim, his Youth Holding Fruit is in fact a likeness of Jesus.

His initial paintings indeed make overt erotic implications, or even propositions. It's as if the painter, then a penniless youthful artist, aligned with Rome's sex workers, offering himself to survive. In the Uffizi, with this idea in consideration, viewers might look to an additional early work, the 1596 masterwork the god of wine, in which the god of alcohol stares coolly at the spectator as he starts to undo the dark ribbon of his garment.

A few annums following the wine deity, what could have motivated the artist to create Amor Vincit Omnia for the art patron Vincenzo Giustiniani, when he was at last growing nearly established with important ecclesiastical commissions? This profane pagan god resurrects the sexual provocations of his initial works but in a more powerful, unsettling way. Half a century later, its secret seemed clear: it was a representation of the painter's lover. A English visitor saw Victorious Cupid in about the mid-seventeenth century and was informed its figure has "the physique and countenance of [Caravaggio's|his] owne youth or assistant that laid with him". The identity of this boy was Francesco.

The artist had been dead for about 40 years when this account was recorded.