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The youthful lad screams as his skull is firmly gripped, a massive thumb digging into his cheek as his father's mighty hand grasps him by the neck. This moment from The Sacrifice of Isaac appears in the Florentine museum, creating unease through the artist's harrowing portrayal of the tormented child from the biblical narrative. The painting appears as if the patriarch, instructed by God to kill his offspring, could break his spinal column with a single turn. However the father's preferred method involves the silvery grey knife he holds in his other hand, prepared to cut the boy's neck. A definite aspect remains – whoever modeled as Isaac for this breathtaking work demonstrated extraordinary expressive skill. There exists not just fear, surprise and pleading in his shadowed eyes but also deep grief that a guardian could abandon him so completely.

The artist adopted a well-known biblical tale and made it so vibrant and visceral that its terrors seemed to happen directly in front of the viewer

Viewing in front of the painting, observers recognize this as a actual countenance, an precise depiction of a adolescent model, because the identical boy – recognizable by his disheveled hair and nearly dark pupils – appears in two other paintings by the master. In each case, that highly emotional face commands the scene. In John the Baptist, he gazes playfully from the shadows while embracing a ram. In Amor Vincit Omnia, he smirks with a toughness acquired on Rome's streets, his dark feathery appendages sinister, a naked child creating chaos in a affluent dwelling.

Amor Vincit Omnia, currently displayed at a London museum, represents one of the most discomfiting masterpieces ever created. Observers feel totally unsettled gazing at it. The god of love, whose darts inspire people with frequently painful desire, is portrayed as a extremely real, vividly illuminated unclothed form, standing over toppled-over items that include musical devices, a musical manuscript, plate armour and an builder's ruler. This pile of possessions echoes, intentionally, the mathematical and construction gear scattered across the floor in the German master's print Melancholy – except here, the melancholic disorder is created by this smirking Cupid and the mayhem he can release.

"Love looks not with the vision, but with the soul, / And therefore is winged Love painted sightless," wrote Shakespeare, just before this painting was created around 1601. But Caravaggio's Cupid is not blind. He stares straight at the observer. That countenance – sardonic and ruddy-cheeked, staring with brazen assurance as he poses naked – is the same one that shrieks in terror in The Sacrifice of Isaac.

As the Italian master painted his three images of the same unusual-appearing kid in the Eternal City at the start of the seventeenth century, he was the most celebrated sacred painter in a metropolis enflamed by Catholic renewal. Abraham's Offering reveals why he was commissioned to decorate sanctuaries: he could adopt a scriptural narrative that had been depicted numerous times before and render it so new, so raw and visceral that the terror seemed to be occurring immediately before the spectator.

However there existed a different aspect to the artist, evident as quickly as he arrived in Rome in the winter that concluded the sixteenth century, as a artist in his initial 20s with no mentor or patron in the city, only skill and audacity. The majority of the works with which he captured the sacred city's eye were anything but holy. What may be the absolute earliest resides in London's National Gallery. A youth parts his crimson mouth in a scream of pain: while stretching out his dirty fingers for a cherry, he has rather been attacked. Boy Bitten By a Lizard is sensuality amid squalor: observers can discern Caravaggio's dismal room reflected in the murky waters of the transparent vase.

The adolescent wears a rose-colored blossom in his hair – a emblem of the sex trade in Renaissance art. Northern Italian artists such as Titian and Jacopo Palma portrayed prostitutes holding blooms and, in a painting destroyed in the second world war but known through photographs, the master portrayed a famous woman courtesan, holding a posy to her bosom. The message of all these botanical indicators is obvious: sex for sale.

How are we to interpret of the artist's erotic portrayals of youths – and of a particular adolescent in specific? It is a inquiry that has split his commentators ever since he gained widespread recognition in the twentieth century. The complicated past truth is that the painter was neither the queer hero that, for example, Derek Jarman presented on film in his twentieth-century film about the artist, nor so completely devout that, as certain artistic historians improbably claim, his Boy With a Basket of Fruit is actually a portrait of Jesus.

His early paintings indeed offer explicit sexual implications, or including propositions. It's as if the painter, then a penniless young artist, aligned with Rome's prostitutes, selling himself to survive. In the Florentine gallery, with this idea in mind, observers might turn to another initial work, the 1596 masterpiece Bacchus, in which the deity of alcohol gazes coolly at you as he starts to untie the black sash of his robe.

A several years following the wine deity, what could have motivated Caravaggio to paint Amor Vincit Omnia for the artistic collector Vincenzo Giustiniani, when he was finally growing nearly established with important church projects? This profane non-Christian god resurrects the erotic challenges of his early works but in a increasingly powerful, unsettling way. Fifty years afterwards, its secret seemed clear: it was a portrait of Caravaggio's companion. A British traveller saw Victorious Cupid in about the mid-seventeenth century and was told its subject has "the physique and countenance of [Caravaggio's|his] own youth or servant that laid with him". The identity of this boy was Cecco.

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