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The youthful lad screams while his skull is firmly held, a massive thumb digging into his face as his parent's mighty palm holds him by the throat. That moment from Abraham's Sacrifice visits the Florentine museum, creating distress through Caravaggio's chilling rendition of the tormented child from the scriptural narrative. It seems as if Abraham, instructed by the Divine to kill his son, could break his neck with a solitary twist. Yet Abraham's chosen method involves the metallic grey blade he holds in his other hand, ready to slit Isaac's neck. One certain aspect remains – whomever modeled as the sacrifice for this astonishing work demonstrated remarkable expressive ability. Within exists not just fear, surprise and begging in his shadowed gaze but also profound sorrow that a protector could abandon him so utterly.

He took a well-known scriptural tale and made it so vibrant and visceral that its terrors appeared to happen right in view of you

Viewing in front of the artwork, viewers recognize this as a real face, an accurate depiction of a adolescent subject, because the same boy – recognizable by his tousled hair and nearly black pupils – features in several additional works by Caravaggio. In every instance, that richly expressive visage commands the scene. In Youth With a Ram, he peers mischievously from the darkness while embracing a ram. In Amor Vincit Omnia, he smirks with a hardness learned on the city's streets, his dark feathery appendages demonic, a unclothed adolescent creating chaos in a affluent dwelling.

Victorious Cupid, currently exhibited at a British gallery, constitutes one of the most discomfiting masterpieces ever created. Observers feel totally unsettled looking at it. Cupid, whose arrows inspire people with frequently agonizing longing, is portrayed as a very real, brightly illuminated unclothed figure, straddling overturned objects that include stringed instruments, a music score, plate armor and an architect's T-square. This heap of possessions resembles, intentionally, the geometric and architectural equipment scattered across the ground in Albrecht Dürer's engraving Melencolia I – except here, the melancholic mess is caused by this grinning Cupid and the turmoil he can release.

"Affection sees not with the eyes, but with the mind, / And thus is winged Cupid depicted blind," wrote Shakespeare, shortly before this painting was created around the early 1600s. But the painter's Cupid is not blind. He stares straight at the observer. That countenance – ironic and ruddy-cheeked, looking with bold confidence as he struts unclothed – is the identical one that shrieks in fear in The Sacrifice of Isaac.

When the Italian master created his three portrayals of the same distinctive-appearing youth in the Eternal City at the start of the 17th century, he was the most celebrated sacred painter in a metropolis ignited by religious renewal. The Sacrifice of Isaac demonstrates why he was commissioned to decorate sanctuaries: he could take a biblical story that had been depicted numerous occasions previously and render it so fresh, so unfiltered and physical that the terror appeared to be happening immediately in front of you.

However there was another side to Caravaggio, apparent as soon as he came in the capital in the winter that ended 1592, as a painter in his initial twenties with no mentor or supporter in the urban center, only skill and audacity. The majority of the works with which he caught the sacred metropolis's eye were everything but devout. What could be the absolute first hangs in the UK's National Gallery. A youth parts his red lips in a scream of agony: while reaching out his dirty fingers for a fruit, he has rather been bitten. Boy Bitten By a Lizard is eroticism amid poverty: observers can discern the painter's dismal chamber reflected in the cloudy waters of the transparent container.

The boy wears a rose-colored flower in his hair – a emblem of the sex trade in Renaissance painting. Venetian painters such as Titian and Palma Vecchio depicted courtesans grasping flowers and, in a work lost in the second world war but known through images, Caravaggio portrayed a famous female prostitute, holding a posy to her bosom. The meaning of all these floral indicators is obvious: intimacy for sale.

How are we to make of Caravaggio's sensual portrayals of youths – and of one boy in particular? It is a inquiry that has split his commentators since he gained mega-fame in the 1980s. The complicated historical truth is that the painter was neither the queer icon that, for example, Derek Jarman put on screen in his twentieth-century movie about the artist, nor so entirely pious that, as certain artistic scholars unbelievably assert, his Boy With a Basket of Fruit is actually a portrait of Christ.

His initial paintings indeed make overt erotic suggestions, or even propositions. It's as if Caravaggio, then a penniless youthful creator, aligned with the city's sex workers, offering himself to live. In the Florentine gallery, with this idea in mind, viewers might look to another initial creation, the 1596 masterpiece the god of wine, in which the god of alcohol gazes coolly at the spectator as he begins to untie the dark sash of his robe.

A few annums after the wine deity, what could have driven Caravaggio to paint Victorious Cupid for the art collector Vincenzo Giustiniani, when he was at last growing nearly established with prestigious church commissions? This profane pagan god resurrects the sexual challenges of his early works but in a increasingly powerful, unsettling way. Half a century afterwards, its hidden meaning seemed clear: it was a representation of the painter's companion. A British traveller saw the painting in about 1649 and was told its figure has "the physique and countenance of [Caravaggio's|his] own boy or assistant that slept with him". The identity of this adolescent was Francesco.

The artist had been deceased for about 40 annums when this account was documented.