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The young boy cries out while his skull is firmly gripped, a large digit digging into his cheek as his father's mighty palm grasps him by the throat. This scene from Abraham's Sacrifice visits the Uffizi Gallery, creating distress through the artist's chilling rendition of the tormented youth from the biblical narrative. It seems as if Abraham, instructed by God to sacrifice his offspring, could snap his neck with a single twist. However the father's preferred approach involves the silvery steel knife he grips in his remaining hand, prepared to cut the boy's throat. A definite aspect stands out – whoever posed as the sacrifice for this astonishing work demonstrated remarkable expressive skill. There exists not just dread, shock and pleading in his darkened gaze but additionally deep sorrow that a protector could betray him so utterly.

The artist adopted a well-known biblical tale and made it so vibrant and raw that its horrors appeared to unfold directly in front of the viewer

Standing in front of the painting, viewers identify this as a actual face, an precise depiction of a young subject, because the same youth – identifiable by his disheveled locks and almost black pupils – features in several additional paintings by the master. In each case, that highly expressive face commands the composition. In Youth With a Ram, he gazes playfully from the darkness while embracing a ram. In Amor Vincit Omnia, he smirks with a hardness acquired on the city's alleys, his dark feathery appendages demonic, a unclothed child running chaos in a affluent residence.

Amor Vincit Omnia, presently displayed at a British museum, constitutes one of the most embarrassing artworks ever painted. Observers feel completely disoriented gazing at it. Cupid, whose arrows fill people with often agonizing desire, is portrayed as a extremely tangible, vividly illuminated unclothed form, straddling overturned objects that comprise musical devices, a music score, plate armour and an builder's ruler. This pile of items resembles, deliberately, the geometric and architectural gear strewn across the floor in Albrecht Dürer's print Melencolia I – save here, the melancholic disorder is created by this smirking Cupid and the turmoil he can unleash.

"Affection looks not with the vision, but with the soul, / And therefore is feathered Love painted sightless," penned the Bard, just before this work was created around the early 1600s. But the painter's god is not unseeing. He stares straight at you. That face – sardonic and ruddy-cheeked, staring with brazen confidence as he struts naked – is the identical one that shrieks in terror in The Sacrifice of Isaac.

When Michelangelo Merisi da Caravaggio painted his multiple images of the same distinctive-looking youth in the Eternal City at the dawn of the seventeenth century, he was the most celebrated religious painter in a city enflamed by religious revival. The Sacrifice of Isaac demonstrates why he was sought to adorn churches: he could adopt a scriptural story that had been portrayed many occasions before and render it so new, so raw and physical that the horror seemed to be happening immediately before the spectator.

However there was another aspect to Caravaggio, apparent as soon as he came in Rome in the winter that concluded the sixteenth century, as a painter in his early twenties with no teacher or supporter in the city, only talent and audacity. Most of the works with which he captured the sacred city's attention were anything but devout. What could be the absolute first hangs in London's National Gallery. A youth parts his crimson mouth in a yell of pain: while reaching out his filthy fingers for a fruit, he has rather been bitten. Youth Bitten by a Reptile is eroticism amid poverty: viewers can see Caravaggio's dismal room reflected in the cloudy liquid of the glass vase.

The adolescent wears a rose-colored blossom in his hair – a symbol of the sex commerce in early modern art. Venetian artists such as Tiziano and Palma Vecchio portrayed courtesans holding flowers and, in a work destroyed in the second world war but documented through photographs, Caravaggio portrayed a famous woman prostitute, clutching a bouquet to her chest. The meaning of all these botanical signifiers is obvious: sex for purchase.

What are we to interpret of Caravaggio's sensual depictions of boys – and of one boy in particular? It is a question that has split his interpreters ever since he gained mega-fame in the 1980s. The complex past truth is that the artist was neither the queer hero that, for example, the filmmaker presented on film in his twentieth-century film Caravaggio, nor so completely pious that, as some artistic historians unbelievably claim, his Youth Holding Fruit is actually a portrait of Jesus.

His early works indeed make overt sexual suggestions, or even propositions. It's as if Caravaggio, then a destitute young artist, identified with the city's prostitutes, offering himself to live. In the Florentine gallery, with this idea in mind, observers might turn to an additional early creation, the sixteenth-century masterwork Bacchus, in which the god of wine stares coolly at you as he starts to undo the black sash of his robe.

A several annums after the wine deity, what could have motivated the artist to create Victorious Cupid for the artistic collector Vincenzo Giustiniani, when he was at last growing nearly respectable with prestigious ecclesiastical commissions? This unholy pagan god resurrects the erotic challenges of his initial paintings but in a increasingly powerful, uneasy way. Half a century afterwards, its hidden meaning seemed obvious: it was a portrait of Caravaggio's lover. A English traveller viewed Victorious Cupid in about 1649 and was told its figure has "the physique and countenance of [Caravaggio's|his] owne youth or assistant that slept with him". The identity of this boy was Cecco.

The artist had been dead for about forty annums when this account was recorded.