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A young boy cries out while his head is forcefully gripped, a massive thumb digging into his cheek as his father's powerful palm holds him by the neck. This moment from The Sacrifice of Isaac appears in the Florentine museum, creating unease through the artist's chilling portrayal of the suffering youth from the scriptural account. It seems as if the patriarch, instructed by God to sacrifice his son, could snap his spinal column with a solitary turn. Yet the father's chosen approach involves the metallic grey knife he holds in his other hand, ready to slit Isaac's throat. One certain aspect remains – whoever posed as Isaac for this astonishing piece demonstrated extraordinary expressive skill. There exists not only fear, shock and begging in his darkened gaze but additionally deep grief that a protector could abandon him so completely.

He adopted a well-known scriptural tale and transformed it so vibrant and visceral that its horrors appeared to unfold directly in view of the viewer

Viewing before the painting, viewers recognize this as a actual countenance, an accurate record of a young subject, because the identical youth – identifiable by his disheveled locks and almost black eyes – appears in two additional paintings by the master. In every case, that richly emotional face dominates the scene. In Youth With a Ram, he peers mischievously from the shadows while holding a ram. In Amor Vincit Omnia, he grins with a toughness acquired on Rome's streets, his dark feathery wings sinister, a naked child running chaos in a affluent residence.

Victorious Cupid, presently displayed at a London gallery, constitutes one of the most discomfiting artworks ever painted. Viewers feel completely disoriented gazing at it. Cupid, whose darts fill people with frequently painful desire, is portrayed as a extremely tangible, brightly illuminated unclothed form, straddling overturned objects that include stringed devices, a musical score, plate armour and an architect's T-square. This pile of possessions echoes, intentionally, the geometric and architectural gear strewn across the ground in the German master's engraving Melencolia I – save here, the gloomy mess is created by this smirking Cupid and the mayhem he can release.

"Affection sees not with the eyes, but with the soul, / And therefore is feathered Love depicted blind," wrote Shakespeare, shortly before this painting was produced around 1601. But Caravaggio's god is not blind. He stares directly at you. That countenance – sardonic and ruddy-faced, looking with brazen confidence as he poses naked – is the identical one that shrieks in terror in Abraham's Test.

As the Italian master painted his three portrayals of the identical unusual-appearing kid in Rome at the dawn of the seventeenth century, he was the most celebrated religious artist in a city enflamed by religious renewal. Abraham's Offering demonstrates why he was sought to decorate churches: he could adopt a biblical story that had been portrayed many times before and render it so new, so unfiltered and visceral that the terror seemed to be occurring immediately in front of the spectator.

Yet there existed a different side to the artist, apparent as quickly as he came in the capital in the cold season that ended the sixteenth century, as a painter in his early twenties with no teacher or supporter in the urban center, just talent and audacity. Most of the works with which he captured the sacred city's eye were anything but devout. What could be the very earliest hangs in the UK's art museum. A young man opens his red lips in a yell of pain: while stretching out his dirty digits for a cherry, he has rather been attacked. Youth Bitten by a Reptile is eroticism amid poverty: viewers can see Caravaggio's dismal room mirrored in the cloudy waters of the glass container.

The adolescent sports a pink blossom in his coiffure – a emblem of the erotic commerce in Renaissance painting. Northern Italian artists such as Tiziano and Palma Vecchio portrayed prostitutes grasping flowers and, in a painting destroyed in the second world war but known through images, the master represented a renowned woman courtesan, clutching a bouquet to her bosom. The message of all these floral indicators is obvious: intimacy for purchase.

What are we to interpret of the artist's erotic depictions of youths – and of one boy in specific? It is a question that has divided his commentators ever since he achieved widespread recognition in the twentieth century. The complicated historical reality is that the artist was not the homosexual hero that, for instance, the filmmaker presented on film in his twentieth-century movie about the artist, nor so entirely devout that, as some art scholars improbably claim, his Boy With a Basket of Fruit is actually a portrait of Jesus.

His initial works do make overt erotic implications, or even offers. It's as if Caravaggio, then a destitute youthful artist, aligned with the city's sex workers, selling himself to live. In the Uffizi, with this thought in mind, observers might look to another early creation, the 1596 masterpiece the god of wine, in which the deity of wine gazes calmly at the spectator as he begins to untie the dark sash of his robe.

A few years after Bacchus, what could have driven Caravaggio to paint Victorious Cupid for the art patron the nobleman, when he was finally becoming almost established with important church projects? This unholy pagan deity resurrects the erotic challenges of his initial works but in a increasingly intense, uneasy way. Fifty years afterwards, its hidden meaning seemed clear: it was a representation of Caravaggio's companion. A British traveller viewed the painting in about 1649 and was informed its subject has "the physique and countenance of [Caravaggio's|his] own boy or servant that laid with him". The name of this boy was Cecco.

The painter had been dead for about 40 years when this story was documented.