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A youthful lad screams while his head is firmly gripped, a large digit digging into his face as his father's mighty palm holds him by the neck. This scene from Abraham's Sacrifice visits the Florentine museum, creating unease through the artist's harrowing rendition of the tormented youth from the biblical narrative. It appears as if Abraham, commanded by God to kill his offspring, could break his spinal column with a solitary turn. However the father's chosen approach involves the silvery grey knife he grips in his other palm, prepared to cut the boy's throat. A certain element remains – whoever posed as Isaac for this astonishing piece displayed extraordinary expressive ability. Within exists not only dread, shock and begging in his darkened gaze but additionally deep grief that a protector could betray him so completely.

He adopted a familiar scriptural tale and made it so fresh and raw that its terrors appeared to unfold right in front of the viewer

Standing in front of the artwork, observers identify this as a actual countenance, an accurate record of a adolescent model, because the same youth – recognizable by his disheveled locks and nearly black eyes – appears in two other paintings by the master. In every instance, that highly expressive face dominates the scene. In Youth With a Ram, he gazes playfully from the shadows while embracing a lamb. In Amor Vincit Omnia, he smirks with a toughness learned on the city's streets, his dark plumed wings demonic, a naked child creating riot in a affluent dwelling.

Amor Vincit Omnia, currently exhibited at a London gallery, constitutes one of the most discomfiting masterpieces ever created. Viewers feel totally unsettled gazing at it. Cupid, whose darts fill people with frequently painful desire, is shown as a extremely tangible, brightly lit unclothed figure, straddling toppled-over items that comprise stringed devices, a music manuscript, plate armour and an architect's T-square. This pile of possessions echoes, deliberately, the mathematical and construction gear strewn across the ground in Albrecht Dürer's print Melencolia I – except in this case, the gloomy mess is caused by this grinning Cupid and the turmoil he can unleash.

"Love looks not with the vision, but with the mind, / And therefore is winged Cupid depicted sightless," penned Shakespeare, shortly before this work was created around 1601. But Caravaggio's god is not blind. He gazes directly at the observer. That countenance – sardonic and rosy-faced, looking with bold assurance as he struts unclothed – is the same one that shrieks in fear in Abraham's Test.

As Michelangelo Merisi da Caravaggio created his three images of the same unusual-looking youth in Rome at the dawn of the 17th century, he was the highly celebrated sacred painter in a city ignited by religious renewal. The Sacrifice of Isaac demonstrates why he was commissioned to adorn sanctuaries: he could take a biblical story that had been portrayed many times previously and make it so fresh, so unfiltered and physical that the horror seemed to be occurring directly before you.

Yet there was a different side to the artist, evident as soon as he arrived in Rome in the winter that concluded the sixteenth century, as a painter in his early twenties with no mentor or supporter in the city, only skill and audacity. Most of the works with which he captured the holy metropolis's attention were anything but devout. That could be the very earliest resides in London's National Gallery. A young man parts his crimson mouth in a yell of pain: while reaching out his filthy fingers for a cherry, he has rather been attacked. Youth Bitten by a Reptile is eroticism amid squalor: observers can see Caravaggio's gloomy room reflected in the cloudy waters of the transparent vase.

The adolescent wears a rose-colored blossom in his coiffure – a symbol of the erotic commerce in Renaissance painting. Northern Italian artists such as Titian and Palma Vecchio depicted prostitutes holding flowers and, in a work lost in the second world war but known through images, Caravaggio portrayed a renowned woman courtesan, clutching a posy to her bosom. The message of all these floral indicators is obvious: sex for sale.

What are we to make of the artist's erotic portrayals of youths – and of one boy in specific? It is a inquiry that has split his commentators ever since he gained mega-fame in the 1980s. The complicated historical truth is that the artist was neither the homosexual hero that, for example, Derek Jarman presented on film in his 1986 film Caravaggio, nor so completely devout that, as certain artistic scholars unbelievably claim, his Boy With a Basket of Fruit is in fact a portrait of Christ.

His early works do make explicit sexual implications, or including propositions. It's as if Caravaggio, then a destitute young creator, identified with the city's prostitutes, selling himself to live. In the Florentine gallery, with this idea in consideration, viewers might turn to another early creation, the 1596 masterpiece Bacchus, in which the god of alcohol gazes calmly at you as he starts to untie the dark sash of his garment.

A several annums following the wine deity, what could have motivated the artist to create Victorious Cupid for the art collector Vincenzo Giustiniani, when he was at last becoming almost respectable with prestigious church commissions? This unholy pagan deity revives the sexual provocations of his initial paintings but in a more powerful, uneasy manner. Fifty years later, its secret seemed clear: it was a representation of Caravaggio's lover. A British visitor viewed the painting in about 1649 and was told its figure has "the physique and countenance of [Caravaggio's|his] own youth or servant that laid with him". The identity of this boy was Francesco.

The painter had been deceased for about forty annums when this story was recorded.