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The youthful boy screams while his head is forcefully gripped, a massive digit pressing into his cheek as his father's mighty hand holds him by the neck. This scene from Abraham's Sacrifice visits the Uffizi Gallery, creating unease through the artist's chilling portrayal of the tormented youth from the scriptural account. It seems as if Abraham, instructed by God to kill his son, could snap his spinal column with a single twist. However the father's preferred approach involves the silvery steel blade he holds in his remaining palm, ready to cut Isaac's throat. One definite aspect remains – whoever modeled as the sacrifice for this breathtaking piece displayed extraordinary acting skill. There exists not just dread, surprise and begging in his darkened gaze but also deep grief that a protector could abandon him so completely.

The artist took a well-known biblical tale and transformed it so vibrant and raw that its terrors appeared to happen directly in view of the viewer

Standing before the painting, observers identify this as a real face, an accurate record of a adolescent subject, because the identical boy – identifiable by his disheveled hair and nearly dark eyes – appears in several other paintings by the master. In every instance, that richly expressive visage commands the composition. In John the Baptist, he gazes playfully from the darkness while holding a ram. In Victorious Cupid, he smirks with a toughness learned on Rome's streets, his black plumed wings sinister, a naked child creating riot in a well-to-do residence.

Amor Vincit Omnia, currently exhibited at a British museum, represents one of the most discomfiting artworks ever painted. Viewers feel totally disoriented gazing at it. The god of love, whose darts fill people with frequently agonizing desire, is portrayed as a very tangible, vividly illuminated unclothed figure, standing over toppled-over objects that comprise stringed devices, a music manuscript, metal armor and an builder's T-square. This pile of items resembles, deliberately, the mathematical and construction equipment strewn across the ground in the German master's print Melencolia I – save in this case, the melancholic disorder is created by this grinning deity and the mayhem he can unleash.

"Affection looks not with the eyes, but with the mind, / And therefore is feathered Cupid painted sightless," penned Shakespeare, just before this painting was created around the early 1600s. But Caravaggio's Cupid is not blind. He gazes directly at the observer. That face – sardonic and ruddy-faced, looking with brazen confidence as he poses naked – is the identical one that shrieks in terror in The Sacrifice of Isaac.

When the Italian master created his three portrayals of the identical unusual-looking kid in the Eternal City at the dawn of the 17th century, he was the most acclaimed religious artist in a city ignited by religious revival. The Sacrifice of Isaac reveals why he was sought to decorate sanctuaries: he could adopt a biblical story that had been portrayed many times previously and render it so fresh, so unfiltered and physical that the horror appeared to be occurring directly in front of you.

Yet there existed a different aspect to Caravaggio, apparent as soon as he arrived in the capital in the winter that concluded 1592, as a painter in his initial twenties with no teacher or patron in the urban center, only skill and audacity. Most of the works with which he caught the sacred city's attention were everything but devout. That could be the absolute earliest hangs in London's National Gallery. A youth opens his crimson lips in a scream of pain: while stretching out his dirty fingers for a cherry, he has rather been bitten. Youth Bitten by a Reptile is sensuality amid squalor: viewers can see the painter's gloomy chamber mirrored in the murky liquid of the transparent vase.

The adolescent wears a pink blossom in his coiffure – a emblem of the erotic commerce in early modern painting. Venetian painters such as Tiziano and Jacopo Palma depicted courtesans grasping blooms and, in a painting lost in the second world war but known through images, the master portrayed a famous female prostitute, clutching a bouquet to her bosom. The message of all these botanical signifiers is clear: sex for purchase.

How are we to interpret of the artist's sensual portrayals of youths – and of a particular adolescent in particular? It is a inquiry that has divided his interpreters since he achieved mega-fame in the twentieth century. The complicated past truth is that the artist was neither the homosexual icon that, for instance, Derek Jarman presented on film in his 1986 movie about the artist, nor so entirely devout that, as some artistic historians improbably assert, his Youth Holding Fruit is in fact a likeness of Christ.

His initial works do make explicit sexual suggestions, or even propositions. It's as if Caravaggio, then a penniless youthful artist, identified with Rome's sex workers, offering himself to live. In the Uffizi, with this thought in consideration, viewers might look to an additional initial creation, the 1596 masterpiece the god of wine, in which the deity of alcohol gazes calmly at the spectator as he starts to untie the dark sash of his robe.

A several years after Bacchus, what could have motivated Caravaggio to create Amor Vincit Omnia for the art collector the nobleman, when he was at last growing almost respectable with prestigious church commissions? This profane non-Christian god resurrects the erotic challenges of his early paintings but in a more powerful, unsettling way. Fifty years later, its secret seemed clear: it was a representation of the painter's companion. A British traveller viewed Victorious Cupid in about 1649 and was informed its subject has "the physique and countenance of [Caravaggio's|his] own youth or assistant that laid with him". The name of this boy was Cecco.

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