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A young boy cries out while his head is forcefully held, a massive digit pressing into his face as his parent's mighty hand holds him by the neck. This scene from Abraham's Sacrifice appears in the Uffizi Gallery, creating unease through the artist's harrowing portrayal of the suffering child from the biblical narrative. It appears as if Abraham, commanded by the Divine to kill his offspring, could break his neck with a single twist. However the father's chosen approach involves the silvery steel knife he holds in his remaining hand, ready to cut the boy's throat. A definite aspect remains – whoever posed as the sacrifice for this astonishing piece displayed remarkable expressive skill. There exists not just fear, surprise and pleading in his darkened eyes but additionally profound sorrow that a guardian could abandon him so utterly.

He adopted a well-known scriptural story and transformed it so vibrant and raw that its horrors appeared to unfold directly in view of the viewer

Viewing before the painting, viewers identify this as a actual countenance, an accurate depiction of a adolescent subject, because the same youth – recognizable by his tousled hair and almost black eyes – appears in several other works by Caravaggio. In every case, that highly expressive visage commands the composition. In John the Baptist, he gazes mischievously from the darkness while holding a lamb. In Victorious Cupid, he grins with a toughness learned on Rome's streets, his black plumed wings demonic, a unclothed adolescent creating riot in a affluent residence.

Amor Vincit Omnia, presently displayed at a British museum, constitutes one of the most embarrassing artworks ever painted. Viewers feel totally disoriented looking at it. The god of love, whose darts fill people with often agonizing desire, is portrayed as a very real, vividly illuminated nude form, standing over toppled-over objects that include musical instruments, a musical score, plate armour and an builder's T-square. This heap of possessions echoes, deliberately, the mathematical and architectural equipment scattered across the floor in Albrecht Dürer's engraving Melancholy – except here, the gloomy disorder is caused by this smirking Cupid and the turmoil he can release.

"Affection sees not with the vision, but with the soul, / And thus is feathered Love painted sightless," penned the Bard, shortly before this work was created around 1601. But Caravaggio's god is not unseeing. He stares directly at the observer. That face – sardonic and ruddy-faced, staring with brazen assurance as he struts unclothed – is the identical one that shrieks in fear in The Sacrifice of Isaac.

When the Italian master painted his multiple images of the same unusual-appearing youth in Rome at the dawn of the 17th century, he was the highly celebrated sacred painter in a city ignited by religious renewal. Abraham's Offering reveals why he was sought to adorn churches: he could take a scriptural narrative that had been portrayed numerous occasions previously and make it so fresh, so unfiltered and visceral that the horror seemed to be happening immediately in front of the spectator.

However there existed another aspect to the artist, evident as soon as he arrived in the capital in the cold season that ended the sixteenth century, as a artist in his initial 20s with no teacher or patron in the urban center, just skill and audacity. Most of the works with which he captured the holy city's eye were everything but devout. That could be the very earliest resides in London's art museum. A youth parts his red lips in a yell of agony: while stretching out his dirty fingers for a cherry, he has instead been bitten. Youth Bitten by a Reptile is sensuality amid poverty: viewers can see Caravaggio's gloomy room reflected in the cloudy waters of the glass container.

The adolescent wears a pink blossom in his coiffure – a symbol of the erotic commerce in early modern art. Northern Italian painters such as Tiziano and Palma Vecchio portrayed prostitutes holding flowers and, in a painting destroyed in the second world war but known through photographs, the master represented a renowned woman courtesan, clutching a posy to her chest. The meaning of all these botanical signifiers is obvious: intimacy for sale.

What are we to interpret of Caravaggio's erotic depictions of boys – and of one boy in specific? It is a question that has divided his interpreters ever since he achieved widespread recognition in the 1980s. The complicated past truth is that the painter was not the queer icon that, for instance, the filmmaker presented on screen in his twentieth-century film Caravaggio, nor so entirely devout that, as some artistic scholars improbably claim, his Boy With a Basket of Fruit is in fact a portrait of Christ.

His early paintings indeed offer overt sexual suggestions, or even propositions. It's as if Caravaggio, then a destitute youthful artist, identified with Rome's prostitutes, offering himself to survive. In the Florentine gallery, with this idea in mind, viewers might look to an additional initial work, the sixteenth-century masterwork Bacchus, in which the deity of wine stares calmly at the spectator as he starts to untie the black ribbon of his garment.

A few years after Bacchus, what could have driven the artist to paint Victorious Cupid for the artistic patron the nobleman, when he was finally growing almost respectable with prestigious ecclesiastical projects? This profane pagan deity resurrects the sexual provocations of his early works but in a increasingly intense, unsettling manner. Half a century afterwards, its hidden meaning seemed clear: it was a representation of Caravaggio's companion. A English visitor viewed 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 name of this adolescent was Francesco.

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