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The youthful boy screams while his head is firmly held, a massive digit pressing into his cheek as his father's mighty hand holds him by the throat. This moment from The Sacrifice of Isaac appears in the Uffizi Gallery, evoking unease through the artist's harrowing portrayal of the tormented child from the scriptural narrative. It seems as if Abraham, instructed by the Divine to kill his son, could snap his neck with a solitary turn. However the father's preferred method involves the silvery grey blade he grips in his remaining hand, prepared to slit the boy's throat. A certain aspect stands out – whoever modeled as the sacrifice for this astonishing work demonstrated remarkable acting skill. Within exists not only fear, shock and pleading in his shadowed gaze but also profound sorrow that a guardian could abandon him so utterly.

He took a familiar biblical tale and transformed it so fresh and visceral that its terrors appeared to unfold right in view of the viewer

Viewing in front of the artwork, observers recognize this as a actual face, an accurate record of a young model, because the same boy – identifiable by his tousled hair and almost dark eyes – appears in two other works by Caravaggio. In every instance, that highly expressive face dominates the composition. In Youth With a Ram, he gazes mischievously from the darkness while embracing a lamb. In Amor Vincit Omnia, he smirks with a hardness learned on Rome's streets, his black feathery appendages demonic, a naked child running riot in a well-to-do dwelling.

Victorious Cupid, currently displayed at a British museum, constitutes one of the most embarrassing masterpieces ever painted. Observers feel totally unsettled gazing at it. The god of love, whose darts inspire people with frequently agonizing desire, is portrayed as a very tangible, brightly lit nude figure, straddling toppled-over objects that comprise stringed instruments, a musical manuscript, plate armor and an builder's T-square. This heap of items echoes, intentionally, the geometric and construction gear strewn across the ground in the German master's print Melencolia I – save here, the gloomy mess is created by this grinning Cupid and the turmoil he can release.

"Love sees not with the eyes, but with the mind, / And therefore is winged Cupid depicted sightless," wrote Shakespeare, shortly before this painting was produced around the early 1600s. But the painter's god is not blind. He stares directly at you. That countenance – ironic and ruddy-cheeked, staring with bold assurance as he struts naked – is the same one that screams in terror in Abraham's Test.

As Michelangelo Merisi da Caravaggio painted his three images of the identical distinctive-appearing kid in the Eternal City at the start of the 17th century, he was the most acclaimed sacred artist in a metropolis enflamed by Catholic renewal. Abraham's Offering demonstrates why he was sought to adorn sanctuaries: he could take a biblical narrative that had been portrayed many times before and render it so fresh, so unfiltered and physical that the horror appeared to be occurring directly in front of the spectator.

Yet there was another side to the artist, evident as quickly as he came in the capital in the winter that concluded the sixteenth century, as a artist in his early 20s with no mentor or supporter in the city, just talent and audacity. Most of the paintings with which he captured the holy city's eye were anything but holy. What may be the very first resides in London's art museum. A youth opens his crimson lips in a yell of pain: while stretching out his filthy digits for a fruit, he has instead been attacked. Boy Bitten By a Lizard is eroticism amid poverty: observers can see Caravaggio's gloomy chamber reflected in the cloudy waters of the glass vase.

The adolescent sports a pink blossom in his hair – a symbol of the sex trade in early modern art. Venetian artists such as Titian and Jacopo Palma portrayed prostitutes holding flowers and, in a work destroyed in the second world war but documented through photographs, Caravaggio represented a famous female prostitute, holding a posy to her bosom. The message of all these floral signifiers is clear: sex for purchase.

What are we to interpret of Caravaggio's erotic portrayals of youths – and of a particular boy in specific? It is a inquiry that has split his interpreters ever since he achieved widespread recognition in the twentieth century. The complicated historical reality is that the painter was neither the homosexual hero that, for instance, Derek Jarman presented on screen in his 1986 movie about the artist, nor so entirely devout that, as certain artistic scholars unbelievably assert, his Boy With a Basket of Fruit is actually a portrait of Jesus.

His initial works do make overt erotic suggestions, or including propositions. It's as if Caravaggio, then a penniless youthful creator, aligned with Rome's prostitutes, selling himself to live. In the Uffizi, with this thought in consideration, viewers might look to an additional initial work, the 1596 masterpiece the god of wine, in which the god of alcohol gazes calmly at the spectator as he begins to untie the black ribbon of his garment.

A few annums following the wine deity, what could have driven Caravaggio to paint Amor Vincit Omnia for the artistic patron the nobleman, when he was finally becoming almost established with important church commissions? This profane pagan god resurrects the erotic challenges of his initial works but in a increasingly powerful, unsettling way. Fifty years later, its secret seemed obvious: it was a representation of the painter's companion. A English traveller saw the painting in about 1649 and was told its subject has "the physique and countenance of [Caravaggio's|his] owne boy or assistant that laid with him". The name of this boy was Cecco.

The artist had been dead for about 40 years when this story was recorded.