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A young boy screams while his head is firmly gripped, a massive digit digging into his face as his parent's mighty hand grasps him by the throat. This moment from The Sacrifice of Isaac appears in the Florentine museum, evoking distress through the artist's harrowing portrayal of the suffering youth from the scriptural account. The painting seems as if the patriarch, commanded by God to kill his son, could break his spinal column with a solitary twist. Yet Abraham's preferred approach involves the metallic steel knife he holds in his other palm, ready to cut the boy's throat. One definite aspect stands out – whoever posed as Isaac for this astonishing piece displayed remarkable expressive skill. Within exists not just dread, surprise and pleading in his darkened eyes but additionally deep grief that a protector could abandon him so utterly.

The artist took a well-known biblical tale and made it so fresh and visceral that its horrors seemed to happen right in view of the viewer

Viewing in front of the painting, viewers identify this as a real countenance, an precise depiction of a young subject, because the identical youth – identifiable by his disheveled locks and nearly dark pupils – features in several additional paintings by Caravaggio. In every instance, that highly expressive visage dominates the scene. In John the Baptist, he peers playfully from the darkness while holding a lamb. In Victorious Cupid, he grins with a hardness acquired on Rome's alleys, his dark feathery wings demonic, a naked adolescent creating chaos in a well-to-do dwelling.

Amor Vincit Omnia, currently displayed at a London gallery, constitutes one of the most embarrassing masterpieces ever painted. Observers feel completely unsettled gazing at it. Cupid, whose arrows fill people with often agonizing longing, is shown as a extremely tangible, brightly lit unclothed form, straddling overturned objects that include musical instruments, a music manuscript, plate armour and an architect's T-square. This pile of possessions resembles, deliberately, the mathematical and architectural equipment scattered across the floor in the German master's engraving Melencolia I – except here, the melancholic mess is created by this grinning deity and the turmoil he can unleash.

"Affection looks not with the vision, but with the soul, / And thus is winged Love depicted sightless," wrote the Bard, shortly prior to this work was created around 1601. But Caravaggio's Cupid is not blind. He stares directly at the observer. That countenance – sardonic and rosy-cheeked, staring with brazen assurance as he struts naked – is the identical one that screams in terror in The Sacrifice of Isaac.

As Michelangelo Merisi da Caravaggio created his multiple portrayals of the identical unusual-appearing youth in the Eternal City at the start of the 17th century, he was the most celebrated sacred painter in a city enflamed by religious revival. The Sacrifice of Isaac reveals why he was commissioned to adorn churches: he could take a biblical narrative that had been portrayed numerous occasions before and make it so new, so raw and visceral that the terror seemed to be occurring immediately in front of you.

Yet there existed a different side to the artist, evident as quickly as he came in the capital in the winter that concluded 1592, as a artist in his initial twenties with no teacher or supporter in the city, only talent and boldness. The majority of the works with which he caught the holy metropolis's attention were anything but holy. That could be the absolute earliest resides in London's National Gallery. A young man parts his crimson mouth in a scream of agony: while reaching out his dirty fingers for a fruit, he has rather been attacked. Boy Bitten By a Lizard is eroticism amid poverty: observers can discern the painter's dismal chamber mirrored in the murky liquid of the glass vase.

The adolescent wears a pink blossom in his hair – a symbol of the sex commerce in Renaissance art. Northern Italian painters such as Tiziano and Palma Vecchio portrayed courtesans grasping flowers and, in a work destroyed in the WWII but documented through images, the master represented a renowned woman courtesan, holding a posy to her chest. The message of all these botanical indicators is clear: sex for purchase.

How are we to interpret of Caravaggio's erotic portrayals of boys – and of a particular boy in particular? It is a inquiry that has divided his interpreters since he gained widespread recognition in the 1980s. The complicated historical truth is that the artist was neither the queer hero that, for example, Derek Jarman put on screen in his 1986 film about the artist, nor so completely pious that, as some art historians improbably claim, his Boy With a Basket of Fruit is in fact a portrait of Christ.

His initial works do make explicit erotic suggestions, or including propositions. It's as if the painter, then a penniless youthful artist, aligned with the city's sex workers, selling himself to survive. In the Uffizi, with this thought in consideration, observers might look to an additional early creation, the sixteenth-century masterpiece the god of wine, in which the deity of alcohol gazes coolly at the spectator as he starts to untie the dark ribbon of his robe.

A few years following Bacchus, what could have driven the artist to create Amor Vincit Omnia for the artistic collector the nobleman, when he was finally becoming nearly established with prestigious church commissions? This profane pagan god revives the sexual challenges of his early paintings but in a more powerful, unsettling manner. Fifty years afterwards, its secret seemed obvious: it was a representation of Caravaggio's lover. A English visitor saw Victorious Cupid in about the mid-seventeenth century and was informed its figure has "the body & face of [Caravaggio's|his] owne youth or servant that laid with him". The identity of this boy was Cecco.

The artist had been dead for about forty annums when this story was recorded.