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A youthful boy cries out as his head is firmly gripped, a large digit pressing into his cheek as his parent's powerful palm holds him by the throat. That scene from The Sacrifice of Isaac appears in the Florentine museum, evoking unease through Caravaggio's chilling rendition of the suffering child from the scriptural account. The painting seems as if the patriarch, instructed by God to kill his son, could break his neck with a solitary twist. However Abraham's chosen method involves the metallic grey blade he grips in his other hand, prepared to slit Isaac's throat. One certain element remains – whoever modeled as the sacrifice for this astonishing work demonstrated extraordinary acting skill. There exists not just fear, surprise and pleading in his shadowed eyes but additionally deep sorrow that a guardian could abandon him so completely.

The artist took a well-known scriptural story and made it so vibrant and raw that its terrors appeared to happen right in view of the viewer

Standing before the painting, observers recognize this as a actual countenance, an precise record of a adolescent model, because the same boy – identifiable by his tousled locks and almost dark eyes – features in two additional paintings by the master. In each instance, that highly expressive face dominates the composition. In Youth With a Ram, he gazes mischievously from the shadows while embracing a lamb. In Victorious Cupid, he smirks with a hardness acquired on Rome's streets, his dark feathery wings demonic, a unclothed adolescent running riot in a affluent residence.

Victorious Cupid, presently exhibited at a London museum, constitutes one of the most embarrassing artworks ever created. Observers feel completely unsettled gazing at it. The god of love, whose arrows fill people with frequently painful longing, is portrayed as a very tangible, brightly lit nude figure, straddling overturned items that comprise musical instruments, a musical score, plate armour and an builder's T-square. This heap of possessions resembles, intentionally, the mathematical and construction gear strewn across the ground in the German master's engraving Melancholy – save here, the melancholic disorder is created by this grinning Cupid and the turmoil he can release.

"Love sees not with the vision, but with the soul, / And thus is winged Cupid depicted sightless," wrote Shakespeare, shortly prior to this work was produced around the early 1600s. But the painter's god is not blind. He gazes directly at the observer. That countenance – sardonic and rosy-cheeked, staring with bold confidence as he struts naked – is the identical one that shrieks in terror in The Sacrifice of Isaac.

As Michelangelo Merisi da Caravaggio painted his multiple portrayals of the same distinctive-appearing kid in the Eternal City at the start of the seventeenth century, he was the highly acclaimed sacred painter in a metropolis enflamed by religious renewal. The Sacrifice of Isaac demonstrates why he was commissioned to decorate churches: he could take a biblical story that had been depicted many times before and make it so fresh, so unfiltered and visceral that the terror seemed to be happening directly in front of you.

However there was a different side to Caravaggio, evident as soon as he arrived in Rome in the winter that concluded the sixteenth century, as a artist in his early 20s with no mentor or supporter in the city, only skill and boldness. Most of the paintings with which he caught the holy metropolis's eye were everything but holy. What may be the absolute first resides in London's National Gallery. A young man parts his red mouth in a scream of agony: while stretching out his dirty digits for a cherry, he has rather been attacked. Boy Bitten By a Lizard is eroticism amid poverty: observers can see Caravaggio's gloomy chamber reflected in the cloudy liquid of the transparent container.

The boy wears a rose-colored flower in his coiffure – a symbol of the erotic trade in Renaissance painting. Northern Italian artists such as Titian and Palma Vecchio portrayed courtesans holding flowers and, in a work lost in the WWII but known through photographs, the master portrayed a renowned woman courtesan, clutching a bouquet to her bosom. The meaning of all these botanical signifiers is clear: intimacy for sale.

What are we to make of Caravaggio's erotic portrayals of boys – and of a particular adolescent in specific? It is a question that has divided his interpreters since he achieved widespread recognition in the twentieth century. The complex past reality is that the painter was not the queer hero that, for example, Derek Jarman put on film in his twentieth-century movie Caravaggio, nor so entirely devout that, as certain artistic scholars improbably assert, his Youth Holding Fruit is actually a portrait of Christ.

His early works do offer explicit sexual implications, or even propositions. It's as if the painter, then a penniless youthful creator, aligned with the city's sex workers, offering himself to survive. In the Florentine gallery, with this thought in consideration, viewers might look to another initial creation, the sixteenth-century masterwork the god of wine, in which the deity of wine stares calmly at you as he starts to undo the dark sash of his garment.

A few years after the wine deity, what could have motivated Caravaggio to create Amor Vincit Omnia for the art patron the nobleman, when he was at last growing nearly respectable with prestigious church projects? This unholy pagan deity revives the sexual provocations of his early paintings but in a increasingly intense, uneasy manner. Half a century later, its hidden meaning seemed obvious: it was a portrait of Caravaggio's companion. A English traveller viewed the painting in about the mid-seventeenth century and was told its subject has "the physique and countenance of [Caravaggio's|his] own youth or assistant that laid with him". The name of this adolescent was Cecco.

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