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The youthful lad screams while his head is forcefully held, a massive thumb digging into his face as his parent's powerful hand holds him by the neck. That scene from Abraham's Sacrifice appears in the Uffizi Gallery, creating unease through Caravaggio's harrowing portrayal of the tormented child from the biblical narrative. It seems as if Abraham, commanded by the Divine to kill his son, could snap his neck with a solitary twist. Yet the father's chosen approach involves the metallic steel blade he grips in his remaining hand, ready to cut Isaac's neck. One certain element remains – whomever posed as the sacrifice for this astonishing work demonstrated remarkable expressive ability. There exists not only dread, shock and pleading in his shadowed eyes but additionally deep grief that a guardian could abandon him so utterly.

He took a familiar biblical story and transformed it so fresh and visceral that its terrors seemed to happen right in view of you

Standing in front of the painting, viewers recognize this as a actual countenance, an accurate depiction of a young subject, because the same youth – identifiable by his disheveled locks and almost dark pupils – features in two additional works by the master. In every instance, that richly expressive face commands the scene. In John the Baptist, he peers mischievously from the darkness while holding a ram. In Amor Vincit Omnia, he grins with a toughness learned on Rome's alleys, his dark plumed wings sinister, a naked adolescent running riot in a well-to-do residence.

Amor Vincit Omnia, currently exhibited at a British museum, constitutes one of the most discomfiting artworks ever painted. Viewers feel completely unsettled looking at it. The god of love, whose arrows fill people with frequently painful longing, is shown as a extremely tangible, vividly illuminated unclothed figure, straddling overturned items that include stringed instruments, a music score, metal armour and an builder's ruler. This pile of items resembles, intentionally, the geometric and construction gear scattered across the ground in Albrecht Dürer's engraving Melancholy – except here, the melancholic mess is created by this smirking Cupid and the turmoil he can unleash.

"Affection looks not with the eyes, but with the mind, / And therefore is winged Love painted sightless," penned Shakespeare, just prior to this work was created around 1601. But Caravaggio's god is not unseeing. He stares straight at you. That face – sardonic and rosy-cheeked, staring with brazen confidence as he poses naked – is the same one that shrieks in fear in The Sacrifice of Isaac.

As Michelangelo Merisi da Caravaggio created his multiple images of the same unusual-appearing kid in Rome at the start of the 17th century, he was the highly celebrated sacred painter in a metropolis ignited by Catholic renewal. The Sacrifice of Isaac demonstrates why he was commissioned to adorn churches: he could adopt a biblical story that had been depicted many times previously and make it so new, so raw and visceral that the horror seemed to be occurring directly in front of the spectator.

Yet there existed a different aspect to Caravaggio, evident as soon as he arrived in the capital in the cold season that ended 1592, as a artist in his initial twenties with no mentor or supporter in the urban center, only talent and audacity. Most of the paintings with which he captured the holy city's attention were everything but devout. What may be the very earliest hangs in London's National Gallery. A youth parts his red mouth in a yell of agony: while reaching out his dirty fingers for a fruit, he has rather been attacked. Boy Bitten By a Lizard is eroticism amid squalor: viewers can see Caravaggio's gloomy room mirrored in the cloudy liquid of the transparent container.

The boy sports a pink flower in his coiffure – a emblem of the erotic trade in early modern painting. Northern Italian painters such as Titian and Jacopo Palma portrayed courtesans grasping flowers and, in a work destroyed in the WWII but known through images, the master represented a renowned woman courtesan, holding a bouquet to her bosom. The message of all these floral indicators is clear: intimacy for purchase.

How are we to make of the artist's erotic portrayals of boys – and of a particular boy in specific? It is a inquiry that has split his commentators since he achieved mega-fame in the 1980s. The complex historical reality is that the painter was neither the queer hero that, for example, the filmmaker put on film in his twentieth-century film about the artist, nor so completely pious that, as some artistic historians improbably claim, his Youth Holding Fruit is actually a likeness of Jesus.

His early works do make explicit erotic implications, or including propositions. It's as if the painter, then a penniless youthful creator, identified with Rome's prostitutes, selling himself to live. In the Uffizi, with this idea in mind, viewers might look to another early work, the 1596 masterpiece Bacchus, in which the deity of alcohol stares calmly at the spectator as he begins to undo the black ribbon of his robe.

A few annums after the wine deity, what could have motivated Caravaggio to create Victorious Cupid for the art collector the nobleman, when he was finally growing nearly respectable with prestigious church projects? This profane non-Christian deity revives the sexual provocations of his initial works but in a more intense, unsettling manner. Fifty years afterwards, its secret seemed obvious: it was a representation of Caravaggio's lover. A English visitor saw Victorious Cupid in about 1649 and was informed its subject has "the body & face of [Caravaggio's|his] own boy or servant that laid with him". The name of this boy was Cecco.

The painter had been deceased for about forty years when this story was recorded.