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A youthful boy cries out as his skull is firmly gripped, a massive digit digging into his cheek as his father's powerful palm holds him by the throat. That scene from The Sacrifice of Isaac appears in the Florentine museum, creating distress through the artist's chilling portrayal of the tormented child from the scriptural narrative. It seems as if the patriarch, instructed by the Divine to sacrifice his son, could break his spinal column with a solitary turn. However the father's chosen method involves the silvery grey knife he holds in his other hand, prepared to cut the boy's neck. A definite aspect remains – whomever modeled as Isaac for this astonishing work displayed extraordinary expressive skill. Within exists not only fear, shock and pleading in his shadowed eyes but additionally deep grief that a guardian could betray him so utterly.

He adopted a familiar biblical tale and made it so vibrant and visceral that its terrors appeared to happen right in front of the viewer

Viewing before the artwork, viewers identify this as a real countenance, an accurate record of a young model, because the identical boy – recognizable by his disheveled locks and almost black pupils – appears in two other works by the master. In every case, that highly expressive visage commands the scene. In Youth With a Ram, he gazes playfully from the shadows while holding a ram. In Amor Vincit Omnia, he grins with a hardness acquired on Rome's streets, his dark plumed appendages demonic, a naked adolescent creating riot in a well-to-do dwelling.

Victorious Cupid, presently displayed at a British museum, represents one of the most discomfiting artworks ever created. Observers feel totally unsettled looking at it. Cupid, whose darts fill people with frequently painful longing, is portrayed as a very real, vividly illuminated unclothed form, standing over overturned objects that include musical instruments, a musical score, metal armor and an architect's T-square. This heap of possessions echoes, deliberately, the mathematical and architectural gear strewn across the floor in the German master's print Melancholy – save in this case, the melancholic mess is caused by this smirking Cupid and the mayhem he can unleash.

"Affection sees not with the vision, but with the mind, / And therefore is winged Cupid painted blind," penned the Bard, just prior to this work was produced around 1601. But the painter's Cupid is not unseeing. He stares straight at the observer. That face – ironic and ruddy-faced, looking with brazen assurance as he struts unclothed – is the identical one that shrieks in terror in The Sacrifice of Isaac.

As Michelangelo Merisi da Caravaggio created his three images of the identical unusual-looking youth in Rome at the dawn of the 17th century, he was the highly celebrated sacred artist in a metropolis ignited by Catholic revival. Abraham's Offering demonstrates why he was commissioned to decorate churches: he could adopt a biblical narrative that had been portrayed many times before and make it so fresh, so raw and physical that the horror appeared to be occurring directly before you.

Yet there was another aspect to Caravaggio, apparent as quickly as he arrived in the capital in the cold season that ended the sixteenth century, as a artist in his early twenties with no mentor or supporter in the city, only skill and audacity. The majority of the paintings with which he caught the holy metropolis's eye were anything but holy. What may be the absolute earliest resides in London's National Gallery. A young man parts his crimson lips in a scream of pain: while stretching out his filthy fingers for a fruit, he has rather been attacked. Youth Bitten by a Reptile is eroticism amid poverty: viewers can see Caravaggio's dismal room mirrored in the cloudy liquid of the transparent container.

The adolescent sports a pink blossom in his coiffure – a emblem of the sex commerce in Renaissance art. Venetian painters such as Tiziano and Jacopo Palma depicted courtesans grasping blooms and, in a work destroyed in the WWII but documented through images, Caravaggio portrayed a famous female courtesan, holding a bouquet to her chest. The meaning of all these floral indicators is clear: intimacy for purchase.

What are we to make of the artist's sensual portrayals of boys – and of a particular boy in specific? It is a question that has split his commentators since he achieved mega-fame in the twentieth century. The complex past reality is that the artist was neither the homosexual hero that, for instance, Derek Jarman presented on screen in his 1986 movie Caravaggio, nor so completely devout that, as certain artistic scholars improbably claim, his Youth Holding Fruit is actually a likeness of Christ.

His early works do make overt sexual suggestions, or including offers. It's as if the painter, then a penniless youthful artist, aligned with Rome's sex workers, selling himself to survive. In the Florentine gallery, with this thought in mind, observers might look to another early creation, the sixteenth-century masterpiece the god of wine, in which the god of wine gazes coolly at you as he starts to undo the dark ribbon of his garment.

A several years after the wine deity, what could have motivated the artist to create Victorious Cupid for the artistic collector Vincenzo Giustiniani, when he was finally becoming almost respectable with important church commissions? This profane pagan deity resurrects the erotic challenges of his initial paintings but in a increasingly intense, uneasy way. Fifty years later, its hidden meaning seemed obvious: it was a portrait of the painter's lover. A British traveller 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 Francesco.

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