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A youthful lad cries out while his head is firmly gripped, a massive thumb digging into his face as his father's mighty hand grasps him by the neck. That moment from Abraham's Sacrifice visits the Florentine museum, creating distress through Caravaggio's chilling rendition of the suffering child from the scriptural narrative. The painting appears as if Abraham, instructed by God to kill his son, could break his neck with a solitary twist. However Abraham's chosen method involves the silvery grey knife he holds in his remaining palm, ready to cut Isaac's neck. One definite aspect remains – whoever posed as Isaac for this breathtaking piece demonstrated remarkable acting ability. There exists not just dread, surprise and begging in his darkened eyes but also profound grief that a protector could betray him so utterly.

He adopted a familiar scriptural tale and made it so vibrant and visceral that its terrors seemed to happen right in view of you

Viewing in front of the artwork, observers identify this as a real face, an precise record of a adolescent model, because the identical boy – identifiable by his tousled locks and almost black eyes – features in two additional works by Caravaggio. In each instance, that highly expressive visage dominates the scene. In Youth With a Ram, he gazes playfully from the shadows while holding a lamb. In Victorious Cupid, he grins with a hardness acquired on Rome's alleys, his dark plumed wings sinister, a naked adolescent creating chaos in a affluent dwelling.

Victorious Cupid, currently exhibited at a London museum, represents one of the most discomfiting masterpieces ever painted. Observers feel totally unsettled gazing at it. Cupid, whose darts fill people with frequently agonizing desire, is shown as a extremely real, vividly illuminated nude figure, straddling overturned objects that comprise musical devices, a music score, metal armour and an architect's ruler. This heap of items resembles, intentionally, the mathematical and architectural equipment scattered across the ground in Albrecht Dürer's print Melencolia I – except here, the melancholic disorder is caused by this grinning Cupid and the turmoil he can release.

"Love looks not with the vision, but with the soul, / And thus is feathered Cupid depicted sightless," penned the Bard, just prior to this painting was produced around the early 1600s. But the painter's god is not blind. He stares directly at you. That face – sardonic and ruddy-cheeked, staring with brazen confidence as he poses unclothed – is the same one that shrieks in fear in The Sacrifice of Isaac.

As Michelangelo Merisi da Caravaggio created his three images of the identical distinctive-appearing kid in the Eternal City at the dawn of the 17th century, he was the most celebrated religious painter in a city enflamed by religious renewal. The Sacrifice of Isaac reveals why he was sought to adorn sanctuaries: he could take a scriptural narrative that had been portrayed numerous occasions before and make it so fresh, so unfiltered and physical that the horror seemed to be occurring directly in front of you.

Yet there was a different side to the artist, apparent as soon as he came in the capital in the winter that ended the sixteenth century, as a artist in his early twenties with no teacher or patron in the urban center, just talent and audacity. Most of the paintings with which he captured the holy metropolis's eye were everything but holy. That may be the very first resides in the UK's art museum. A youth parts his crimson lips in a scream of agony: while reaching out his dirty digits for a fruit, he has instead been attacked. Youth Bitten by a Reptile is sensuality amid squalor: observers can see Caravaggio's gloomy chamber mirrored in the murky liquid of the glass vase.

The adolescent wears a pink blossom in his coiffure – a symbol of the sex trade in Renaissance painting. Northern Italian painters such as Titian and Jacopo Palma depicted courtesans holding blooms and, in a painting lost in the WWII but known through photographs, the master portrayed a famous woman courtesan, holding a bouquet to her chest. The meaning of all these botanical indicators is obvious: sex for sale.

How are we to make of the artist's sensual depictions of boys – and of a particular boy in specific? It is a question that has divided his interpreters ever since he gained widespread recognition in the twentieth century. The complex past reality is that the painter was not the queer hero that, for example, the filmmaker put on film in his twentieth-century movie about the artist, nor so entirely pious that, as certain art historians unbelievably assert, his Boy With a Basket of Fruit is actually a likeness of Jesus.

His early paintings do offer overt sexual suggestions, or including propositions. It's as if the painter, then a penniless youthful creator, aligned with Rome's prostitutes, offering himself to live. In the Uffizi, with this idea in consideration, observers might look to another initial creation, the sixteenth-century masterwork the god of wine, in which the deity of wine stares coolly at you as he starts to untie the dark ribbon of his garment.

A several years following Bacchus, what could have driven the artist to paint Victorious Cupid for the art collector the nobleman, when he was at last growing almost established with important church projects? This unholy pagan god revives the sexual provocations of his initial works but in a increasingly powerful, uneasy way. Half a century afterwards, its hidden meaning seemed clear: it was a representation of Caravaggio's companion. A British traveller saw the painting in about 1649 and was informed its subject has "the physique and countenance of [Caravaggio's|his] owne youth or servant that slept with him". The identity of this boy was Cecco.

The artist had been dead for about 40 annums when this account was recorded.