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The youthful boy cries out as his skull is forcefully gripped, a massive digit pressing into his face as his father's powerful hand grasps him by the neck. This moment from The Sacrifice of Isaac visits the Uffizi Gallery, creating unease through Caravaggio's harrowing portrayal of the tormented youth from the biblical narrative. The painting appears as if the patriarch, commanded by the Divine to kill his offspring, could snap his spinal column with a solitary turn. However Abraham's preferred approach involves the metallic steel blade he grips in his other palm, ready to slit the boy's neck. A definite aspect remains – whomever posed as Isaac for this astonishing piece demonstrated extraordinary expressive ability. There exists not only fear, surprise and begging in his shadowed gaze but also profound grief that a guardian could betray him so completely.

The artist adopted a familiar scriptural story and transformed it so vibrant and visceral that its terrors appeared to unfold directly in view of you

Viewing in front of the artwork, observers identify this as a actual face, an precise record of a adolescent subject, because the identical boy – identifiable by his tousled hair and nearly dark eyes – features in two other paintings by the master. In every case, that richly expressive visage commands the scene. In Youth With a Ram, he peers playfully from the darkness while embracing a ram. In Amor Vincit Omnia, he grins with a toughness learned on the city's streets, his black feathery wings demonic, a naked adolescent running riot in a affluent dwelling.

Amor Vincit Omnia, presently displayed at a London gallery, represents one of the most discomfiting artworks ever painted. Observers feel completely unsettled looking at it. The god of love, whose darts fill people with often agonizing desire, is portrayed as a extremely tangible, brightly illuminated nude form, straddling overturned objects that comprise musical devices, a musical manuscript, plate armor and an architect's ruler. This heap of items resembles, deliberately, the geometric and construction gear scattered across the floor in Albrecht Dürer's engraving Melancholy – save here, the melancholic disorder is caused by this grinning Cupid and the mayhem he can release.

"Affection looks not with the eyes, but with the soul, / And thus is winged Love depicted sightless," wrote the Bard, shortly prior to this work was produced around 1601. But Caravaggio's Cupid is not unseeing. He stares straight at you. That face – ironic and ruddy-cheeked, staring with brazen confidence as he poses naked – is the same one that shrieks in terror in Abraham's Test.

As Michelangelo Merisi da Caravaggio painted his multiple images of the same unusual-appearing youth in the Eternal City at the start of the seventeenth century, he was the most celebrated religious artist in a metropolis enflamed by religious renewal. The Sacrifice of Isaac demonstrates why he was sought to decorate sanctuaries: he could adopt a scriptural narrative that had been portrayed numerous occasions before and make it so new, so raw and visceral that the horror appeared to be happening directly in front of the spectator.

Yet there existed a different side to the artist, apparent as soon as he came in the capital in the winter that concluded 1592, as a artist in his early 20s with no teacher or supporter in the urban center, just skill and audacity. The majority of the works with which he captured the sacred metropolis's eye were anything but devout. What may be the absolute earliest resides in the UK's National Gallery. A youth opens his red lips in a scream of pain: while stretching out his filthy digits for a cherry, he has instead been bitten. Boy Bitten By a Lizard is eroticism amid squalor: viewers can discern the painter's dismal room mirrored in the murky waters of the transparent vase.

The adolescent sports a rose-colored flower in his hair – a emblem of the sex trade in early modern 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 images, the master portrayed a renowned woman courtesan, clutching a posy to her chest. The message of all these botanical indicators is clear: intimacy for sale.

What are we to interpret of Caravaggio's sensual portrayals of youths – and of one boy in specific? It is a inquiry that has divided his commentators since he achieved mega-fame in the 1980s. The complicated past reality is that the painter was neither the queer hero that, for example, Derek Jarman presented on film in his twentieth-century movie Caravaggio, nor so completely pious that, as some art historians unbelievably assert, his Youth Holding Fruit is actually a portrait of Jesus.

His early works indeed make overt sexual implications, or including offers. It's as if the painter, then a destitute youthful creator, identified with Rome's sex workers, selling himself to survive. In the Florentine gallery, with this idea in mind, viewers might look to another initial work, the 1596 masterwork the god of wine, in which the deity of wine stares calmly at the spectator as he starts to untie the dark sash of his robe.

A few annums after Bacchus, what could have driven Caravaggio to create Victorious Cupid for the artistic patron Vincenzo Giustiniani, when he was at last becoming almost established with important ecclesiastical commissions? This unholy pagan god resurrects the erotic provocations of his initial works but in a more powerful, unsettling manner. Fifty years later, its hidden meaning seemed clear: it was a portrait of the painter's lover. A British traveller saw Victorious Cupid in about the mid-seventeenth century and was informed its figure has "the physique and countenance of [Caravaggio's|his] own youth or assistant that laid with him". The identity of this boy was Francesco.

The painter had been dead for about forty annums when this story was documented.