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The young lad screams as his skull is forcefully gripped, a massive thumb digging into his face as his parent's mighty palm holds him by the throat. This moment from The Sacrifice of Isaac appears in the Florentine museum, evoking unease through the artist's harrowing portrayal of the suffering youth from the biblical narrative. It appears as if the patriarch, commanded by God to kill his son, could snap his neck with a solitary turn. However Abraham's preferred method involves the silvery grey knife he grips in his remaining hand, ready to cut the boy's neck. A certain aspect remains – whomever modeled as Isaac for this astonishing work displayed remarkable expressive ability. Within exists not just fear, shock and begging in his darkened gaze but additionally profound grief that a guardian could betray him so utterly.

He adopted a familiar scriptural tale and made it so fresh and raw that its terrors appeared to unfold directly in view of the viewer

Standing before the painting, observers recognize this as a actual face, an precise depiction of a adolescent subject, because the same youth – identifiable by his disheveled hair and almost dark eyes – features in several other works by the master. In each instance, that richly emotional visage commands the composition. In John the Baptist, he peers playfully from the shadows while embracing a ram. In Amor Vincit Omnia, he grins with a toughness acquired on Rome's alleys, his black plumed appendages sinister, a unclothed adolescent running riot in a well-to-do residence.

Amor Vincit Omnia, presently exhibited at a London museum, constitutes one of the most discomfiting artworks ever created. Viewers feel completely disoriented gazing at it. The god of love, whose arrows fill people with often painful longing, is portrayed as a very tangible, vividly lit unclothed figure, straddling overturned items that include musical instruments, a music manuscript, plate armor and an builder's T-square. This heap of items echoes, deliberately, the mathematical and construction equipment scattered across the floor in Albrecht Dürer's print Melancholy – except in this case, the melancholic disorder is created by this smirking Cupid and the mayhem he can unleash.

"Love looks not with the vision, but with the mind, / And thus is winged Love depicted blind," wrote Shakespeare, shortly before this work was produced around the early 1600s. But the painter's Cupid is not blind. He stares straight at you. That countenance – ironic and ruddy-faced, staring with brazen confidence as he poses unclothed – is the identical one that shrieks in fear in Abraham's Test.

As the Italian master created his multiple portrayals of the identical distinctive-looking youth in the Eternal City at the dawn of the 17th century, he was the highly celebrated religious painter in a metropolis ignited by religious revival. Abraham's Offering demonstrates why he was commissioned to decorate churches: he could adopt a biblical story that had been portrayed numerous occasions before and make it so fresh, so unfiltered and visceral that the terror appeared to be occurring directly in front of the spectator.

Yet there was a different side to Caravaggio, evident as quickly as he came in Rome in the cold season that ended the sixteenth century, as a painter in his early 20s with no teacher or patron in the urban center, only skill and audacity. Most of the works with which he captured the holy metropolis's attention were everything but devout. What may be the very first hangs in London's art museum. A youth parts his red lips in a scream of agony: while stretching out his dirty fingers for a fruit, he has instead been attacked. Youth Bitten by a Reptile is sensuality amid squalor: viewers can discern the painter's dismal chamber reflected in the cloudy liquid of the transparent container.

The boy wears a pink flower in his hair – a symbol of the sex trade in early modern art. Northern Italian painters such as Tiziano and Palma Vecchio portrayed prostitutes grasping flowers and, in a painting destroyed in the second world war but known through photographs, Caravaggio portrayed a renowned woman courtesan, clutching a bouquet to her bosom. The message of all these botanical signifiers is obvious: sex for sale.

How are we to interpret of Caravaggio's sensual depictions of boys – and of a particular boy in particular? It is a question that has divided his interpreters since he gained mega-fame in the twentieth century. The complex historical reality is that the artist was not the queer hero that, for instance, Derek Jarman presented on film in his 1986 movie Caravaggio, nor so completely pious that, as some artistic historians unbelievably claim, his Youth Holding Fruit is actually a portrait of Christ.

His initial paintings indeed offer overt sexual implications, or even propositions. It's as if the painter, then a destitute youthful artist, aligned with the city's sex workers, offering himself to survive. In the Florentine gallery, with this idea in mind, observers might look to an additional early creation, the 1596 masterpiece Bacchus, in which the deity of wine gazes coolly at you as he begins to undo the black sash of his robe.

A several annums after the wine deity, what could have driven Caravaggio to paint Amor Vincit Omnia for the artistic collector Vincenzo Giustiniani, when he was finally growing almost respectable with prestigious ecclesiastical commissions? This profane non-Christian deity resurrects the sexual challenges of his early paintings but in a increasingly intense, uneasy manner. Fifty years afterwards, its hidden meaning seemed clear: it was a portrait of Caravaggio's companion. A British visitor saw Victorious Cupid in about the mid-seventeenth century and was told its subject has "the physique and countenance of [Caravaggio's|his] owne youth or servant that slept with him". The name of this boy was Cecco.

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