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A young lad screams while his head is forcefully held, a large digit pressing into his cheek as his parent's powerful hand grasps him by the neck. That scene from The Sacrifice of Isaac visits the Uffizi Gallery, creating distress through Caravaggio's harrowing rendition of the tormented youth from the biblical account. It appears as if the patriarch, instructed by God to kill his son, could break his spinal column with a solitary turn. However the father's chosen method involves the metallic steel knife he holds in his other palm, ready to cut the boy's throat. A definite element stands out – whoever modeled as Isaac for this astonishing piece displayed remarkable expressive ability. Within exists not only dread, surprise and pleading in his shadowed gaze but additionally profound sorrow that a guardian could betray him so completely.

The artist took a familiar scriptural tale and transformed it so vibrant and visceral that its terrors appeared to unfold right in view of the viewer

Standing before the artwork, viewers identify this as a actual face, an precise record of a young subject, because the same boy – recognizable by his disheveled hair and nearly black pupils – features in several other works by Caravaggio. In each instance, that highly expressive face dominates the composition. In Youth With a Ram, he gazes playfully from the darkness while embracing a ram. In Amor Vincit Omnia, he smirks with a hardness acquired on the city's alleys, his black plumed appendages demonic, a naked adolescent creating chaos in a affluent residence.

Victorious Cupid, presently displayed at a British museum, constitutes one of the most discomfiting artworks ever painted. Viewers feel completely unsettled gazing at it. Cupid, whose darts inspire people with often agonizing desire, is shown as a very tangible, vividly lit nude figure, standing over overturned objects that comprise stringed devices, a musical score, metal armour and an architect's T-square. This pile of items echoes, intentionally, the mathematical and architectural gear strewn across the ground in the German master's print Melencolia I – except here, the gloomy mess is created by this grinning Cupid and the mayhem he can unleash.

"Affection looks not with the eyes, but with the mind, / And therefore is feathered Cupid painted sightless," wrote Shakespeare, just before this painting was created around the early 1600s. But the painter's Cupid is not unseeing. He gazes directly at the observer. That face – sardonic and ruddy-cheeked, staring with bold confidence as he poses naked – is the same one that screams in terror in Abraham's Test.

When the Italian master painted his three portrayals of the same unusual-appearing youth in the Eternal City at the start of the seventeenth century, he was the highly acclaimed sacred painter in a metropolis enflamed by Catholic renewal. Abraham's Offering demonstrates why he was commissioned to decorate churches: he could adopt a scriptural narrative that had been portrayed many times before and render it so new, so unfiltered and physical that the terror appeared to be occurring directly in front of you.

However there was a different aspect to Caravaggio, evident as quickly as he came in Rome in the cold season that concluded the sixteenth century, as a artist in his early twenties with no teacher or patron in the urban center, only talent and boldness. The majority of the paintings with which he captured the sacred city's eye were everything but devout. What may be the very earliest resides in the UK's art museum. A young man opens his crimson mouth in a yell of pain: while stretching out his dirty fingers for a cherry, he has rather been bitten. Boy Bitten By a Lizard is sensuality amid squalor: observers can see Caravaggio's dismal chamber mirrored in the cloudy liquid of the transparent vase.

The adolescent sports a rose-colored flower in his coiffure – a symbol of the erotic commerce in Renaissance art. Venetian artists such as Titian and Palma Vecchio depicted prostitutes holding flowers and, in a work lost in the WWII but known through images, Caravaggio portrayed a famous female courtesan, clutching a posy to her chest. The message of all these floral signifiers is clear: intimacy for sale.

What are we to make of Caravaggio's erotic portrayals of boys – and of a particular adolescent in particular? It is a inquiry that has split his interpreters since he achieved widespread recognition in the twentieth century. The complicated historical reality is that the artist was neither the homosexual hero that, for example, the filmmaker put on screen in his 1986 movie about the artist, nor so entirely pious that, as some artistic scholars improbably assert, his Youth Holding Fruit is actually a portrait of Christ.

His initial works indeed offer overt erotic suggestions, or including offers. It's as if the painter, then a penniless youthful creator, identified with Rome's prostitutes, offering himself to live. In the Uffizi, with this thought in mind, observers might turn to another early creation, the sixteenth-century masterpiece the god of wine, in which the god of alcohol gazes calmly at the spectator as he starts to undo the black sash of his robe.

A few annums after Bacchus, what could have driven Caravaggio to create Victorious Cupid for the art patron the nobleman, when he was finally growing nearly respectable with prestigious church projects? This unholy pagan deity resurrects the erotic provocations of his early works but in a increasingly intense, unsettling way. Half a century later, its secret seemed clear: it was a representation of Caravaggio's companion. A English traveller viewed Victorious Cupid in about 1649 and was told its subject has "the body & face of [Caravaggio's|his] own youth or assistant that laid with him". The identity of this adolescent was Francesco.

The artist had been dead for about 40 annums when this story was recorded.