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A youthful lad screams while his head is firmly held, a massive digit digging into his cheek as his father's mighty hand holds him by the neck. That moment from Abraham's Sacrifice appears in the Florentine museum, creating unease through Caravaggio's harrowing rendition of the suffering youth from the scriptural narrative. It seems as if Abraham, instructed by God to kill his son, could break his spinal column with a single twist. Yet the father's preferred approach involves the silvery steel blade he holds in his remaining hand, ready to cut the boy's throat. One definite aspect remains – whomever posed as Isaac for this astonishing piece demonstrated remarkable acting ability. Within exists not only fear, surprise and pleading in his darkened eyes but additionally profound grief that a guardian could abandon him so completely.

He adopted a well-known scriptural story and transformed it so vibrant and raw that its horrors appeared to happen right in view of the viewer

Standing before the artwork, viewers identify this as a real countenance, an accurate record of a young subject, because the same boy – recognizable by his tousled locks and nearly dark pupils – features in two additional works by the master. In every case, that highly expressive face commands the scene. In John the Baptist, he gazes playfully from the darkness while holding a ram. In Victorious Cupid, he grins with a hardness learned on the city's streets, his dark feathery appendages demonic, a unclothed child running chaos in a affluent dwelling.

Victorious Cupid, presently exhibited at a London museum, represents one of the most discomfiting masterpieces ever painted. Observers feel completely disoriented gazing at it. Cupid, whose darts fill people with often painful longing, is portrayed as a very tangible, brightly illuminated nude form, standing over toppled-over objects that comprise stringed instruments, a music score, plate armor and an builder's ruler. This heap of items echoes, intentionally, the mathematical and construction gear scattered across the ground in the German master's engraving Melencolia I – save in this case, the gloomy disorder is caused by this grinning Cupid and the mayhem he can unleash.

"Love looks not with the eyes, but with the soul, / And therefore is feathered Love painted blind," penned the Bard, shortly prior to this painting was produced around 1601. But Caravaggio's Cupid is not unseeing. He gazes directly at you. That countenance – ironic and ruddy-cheeked, looking with bold confidence as he poses naked – is the same one that screams in terror in The Sacrifice of Isaac.

As the Italian master created his three images of the same unusual-looking kid in the Eternal City at the start of the seventeenth century, he was the highly acclaimed sacred painter in a metropolis ignited by religious revival. Abraham's Offering reveals why he was sought to decorate sanctuaries: he could take a biblical narrative that had been depicted numerous occasions previously and render it so fresh, so unfiltered and visceral that the terror appeared to be happening immediately in front of the spectator.

However there was a different aspect to the artist, evident as soon as he came in the capital in the winter that concluded 1592, as a painter in his early 20s with no mentor or patron in the urban center, only skill and audacity. The majority of the works with which he captured the holy city's eye were anything but holy. What could be the very earliest resides in the UK's art museum. A young man parts his crimson mouth in a scream of pain: while reaching out his dirty digits for a fruit, he has rather been attacked. Youth Bitten by a Reptile is sensuality amid poverty: viewers can discern Caravaggio's dismal chamber reflected in the murky waters of the glass container.

The adolescent wears a pink flower in his hair – a emblem of the sex commerce in early modern painting. Northern Italian painters such as Titian and Palma Vecchio depicted courtesans grasping flowers and, in a painting lost in the WWII but known through images, the master portrayed a renowned woman courtesan, holding a posy to her chest. The message of all these botanical indicators is clear: intimacy for sale.

What are we to make of Caravaggio's erotic portrayals of boys – and of one adolescent in specific? It is a question that has divided his commentators ever since he gained widespread recognition in the twentieth century. The complex historical reality is that the artist was not the homosexual icon that, for example, the filmmaker put on film in his twentieth-century film about the artist, nor so entirely devout that, as some art historians improbably claim, his Boy With a Basket of Fruit is actually a likeness of Jesus.

His initial works do make explicit erotic suggestions, or even propositions. It's as if the painter, then a penniless young creator, identified with the city's sex workers, offering himself to survive. In the Florentine gallery, with this idea in consideration, observers might look to an additional early creation, the sixteenth-century masterpiece Bacchus, in which the god of wine gazes coolly at you as he starts to untie the black ribbon of his robe.

A several years after Bacchus, what could have driven the artist to create Victorious Cupid for the artistic collector the nobleman, when he was at last growing almost respectable with prestigious ecclesiastical commissions? This profane pagan god resurrects the erotic provocations of his initial paintings but in a more powerful, unsettling manner. Fifty years afterwards, its secret seemed obvious: it was a portrait of the painter's lover. A British traveller saw the painting in about 1649 and was told its subject has "the physique and countenance of [Caravaggio's|his] owne boy or assistant that laid with him". The identity of this boy was Francesco.

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