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The young boy cries out as his head is forcefully gripped, a large digit digging into his cheek as his parent's mighty hand holds him by the neck. That scene from Abraham's Sacrifice visits the Florentine museum, creating distress through Caravaggio's chilling portrayal of the suffering child from the scriptural narrative. The painting appears as if Abraham, instructed by God to kill his offspring, could snap his spinal column with a solitary turn. However the father's preferred approach involves the metallic grey knife he holds in his other palm, prepared to cut the boy's throat. One certain element remains – whomever modeled as Isaac for this astonishing work displayed remarkable acting skill. There exists not only fear, surprise and pleading in his darkened eyes but also deep sorrow that a protector could betray him so utterly.

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

Standing before the painting, observers recognize this as a real countenance, an accurate depiction of a adolescent subject, because the identical youth – recognizable by his disheveled locks and nearly black pupils – appears in several additional paintings by Caravaggio. In every case, that highly emotional visage commands the scene. In John the Baptist, he peers mischievously from the darkness while holding a lamb. In Victorious Cupid, he smirks with a hardness acquired on Rome's streets, his black feathery wings demonic, a naked child running chaos in a well-to-do dwelling.

Victorious Cupid, presently exhibited at a British museum, represents one of the most embarrassing artworks ever painted. Observers feel completely unsettled looking at it. The god of love, whose darts fill people with often agonizing desire, is shown as a very tangible, brightly illuminated nude form, standing over toppled-over objects that include stringed devices, a musical score, plate armor and an builder's ruler. This pile of possessions resembles, intentionally, the geometric and construction gear strewn across the floor in Albrecht Dürer's print Melancholy – save in this case, the gloomy disorder is created by this smirking deity and the mayhem he can unleash.

"Love looks not with the eyes, but with the soul, / And therefore is winged Cupid painted sightless," penned Shakespeare, just prior to this painting was created around the early 1600s. But the painter's god is not blind. He stares straight at the observer. That face – ironic and rosy-faced, looking with bold confidence as he struts unclothed – is the same one that screams in fear in The Sacrifice of Isaac.

When Michelangelo Merisi da Caravaggio created his multiple portrayals of the same unusual-looking youth in Rome at the start of the 17th century, he was the most celebrated sacred artist in a metropolis enflamed by Catholic revival. Abraham's Offering demonstrates why he was commissioned to decorate churches: he could adopt a scriptural narrative that had been depicted numerous times previously and render it so fresh, so raw and visceral that the horror seemed to be occurring immediately in front of you.

Yet there was another side to the artist, apparent as quickly as he arrived in the capital in the winter that ended 1592, as a painter in his early 20s with no teacher or supporter in the urban center, only skill and boldness. The majority of the works with which he captured the sacred city's attention were everything but devout. What could be the absolute earliest hangs in London's art museum. A young man parts his crimson lips in a scream of agony: while stretching out his filthy fingers for a cherry, he has rather been bitten. Youth Bitten by a Reptile is eroticism amid squalor: observers can discern the painter's dismal room mirrored in the cloudy waters of the glass container.

The boy wears a rose-colored flower in his hair – a symbol of the sex commerce in early modern painting. Northern Italian artists such as Titian and Jacopo Palma depicted prostitutes holding blooms and, in a painting destroyed in the second world war but known through photographs, the master represented a famous female courtesan, holding a posy to her chest. The meaning of all these floral indicators is clear: intimacy for sale.

How are we to interpret of the artist's erotic portrayals of boys – and of a particular boy in particular? It is a question that has divided his interpreters since he gained widespread recognition in the 1980s. The complex past reality is that the artist was neither the homosexual icon that, for instance, the filmmaker presented on screen in his 1986 film about the artist, nor so completely devout that, as some art historians unbelievably claim, his Boy With a Basket of Fruit is in fact a portrait of Christ.

His early works indeed offer overt erotic implications, or even offers. It's as if the painter, then a destitute youthful creator, identified with the city's prostitutes, selling himself to survive. In the Uffizi, with this thought in mind, viewers might look to another early creation, the sixteenth-century masterwork Bacchus, in which the god of wine stares calmly at you as he begins to undo the black sash of his garment.

A several years after Bacchus, what could have driven the artist to paint Victorious Cupid for the artistic collector the nobleman, when he was finally growing almost established with prestigious church projects? This unholy pagan deity resurrects the erotic provocations of his early works but in a increasingly powerful, unsettling manner. Fifty years later, its secret seemed obvious: it was a representation of the painter's lover. A English visitor viewed the painting in about the mid-seventeenth century and was told its figure has "the body & face of [Caravaggio's|his] own youth or assistant that slept with him". The name of this adolescent was Cecco.

The painter had been deceased for about 40 years when this account was documented.