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The young boy cries out while his head is firmly gripped, a large thumb digging into his face as his father's powerful hand holds him by the neck. That scene from The Sacrifice of Isaac appears in the Uffizi Gallery, evoking distress through Caravaggio's harrowing portrayal of the tormented child from the scriptural account. The painting appears as if the patriarch, instructed by the Divine to sacrifice his son, could snap his neck with a single turn. However Abraham's chosen approach involves the metallic grey blade he holds in his remaining hand, prepared to slit Isaac's throat. A definite element stands out – whoever modeled as the sacrifice for this astonishing piece displayed extraordinary acting ability. There exists not only fear, surprise and begging in his shadowed gaze but additionally profound sorrow that a guardian could abandon him so completely.

He took a familiar scriptural story and transformed it so vibrant and raw that its terrors appeared to unfold directly in view of you

Viewing before the artwork, observers recognize this as a real countenance, an accurate record of a young subject, because the same boy – identifiable by his tousled hair and nearly dark pupils – appears in two other paintings by Caravaggio. In every instance, that highly expressive visage commands the scene. In John the Baptist, he peers mischievously from the shadows while embracing a lamb. In Amor Vincit Omnia, he smirks with a toughness acquired on Rome's alleys, his black plumed wings sinister, a naked child running riot in a affluent residence.

Victorious Cupid, currently exhibited at a London museum, constitutes one of the most discomfiting artworks ever created. Observers feel completely unsettled gazing at it. The god of love, whose darts fill people with frequently painful desire, is shown as a very real, vividly lit unclothed figure, standing over overturned items that comprise musical devices, a music score, metal armor and an architect's ruler. This heap of possessions resembles, deliberately, the geometric and construction gear scattered across the floor in the German master's engraving Melencolia I – except in this case, the melancholic disorder is caused by this grinning Cupid and the mayhem he can release.

"Love sees not with the vision, but with the soul, / And thus is feathered Cupid depicted blind," wrote Shakespeare, shortly before this work was produced around 1601. But Caravaggio's Cupid is not blind. He stares directly at the observer. That face – ironic and ruddy-cheeked, staring with brazen confidence as he poses naked – is the same one that shrieks in fear in The Sacrifice of Isaac.

As the Italian master created his multiple portrayals of the same unusual-looking youth in Rome at the start of the seventeenth century, he was the most celebrated religious painter in a city ignited by Catholic renewal. The Sacrifice of Isaac reveals why he was sought to adorn churches: he could adopt a scriptural story that had been portrayed numerous occasions previously and render it so new, so raw and visceral that the horror appeared to be occurring directly in front of you.

However there was a different aspect to the artist, evident as soon as he came in Rome in the cold season that concluded the sixteenth century, as a artist in his initial twenties with no mentor or supporter in the city, only skill and audacity. The majority of the paintings with which he captured the holy metropolis's eye were everything but devout. That could be the very first resides in London's National Gallery. A youth parts his crimson mouth in a yell of pain: while reaching out his dirty digits for a cherry, he has rather been bitten. Boy Bitten By a Lizard is sensuality amid poverty: viewers can see the painter's dismal room mirrored in the murky waters of the glass vase.

The boy sports a pink flower in his hair – a symbol of the sex trade in Renaissance painting. Venetian artists such as Titian and Jacopo Palma depicted prostitutes holding flowers and, in a painting destroyed in the WWII but known through images, Caravaggio portrayed a famous woman courtesan, clutching a bouquet to her chest. The message of all these floral indicators is obvious: intimacy for purchase.

What are we to interpret of Caravaggio's sensual depictions of youths – and of one boy in specific? It is a inquiry that has divided his commentators since he gained widespread recognition in the 1980s. The complicated past reality is that the painter was neither the homosexual icon that, for instance, the filmmaker presented on film in his 1986 movie Caravaggio, nor so entirely pious that, as some art scholars unbelievably assert, his Youth Holding Fruit is in fact a likeness of Jesus.

His initial paintings do offer overt sexual suggestions, or even offers. It's as if Caravaggio, then a destitute youthful creator, identified with the city's prostitutes, selling himself to survive. In the Uffizi, with this thought in consideration, viewers might look to another initial work, the 1596 masterpiece the god of wine, in which the god of wine stares coolly at you as he starts to untie the black ribbon of his robe.

A several annums following the wine deity, what could have driven Caravaggio to create Victorious Cupid for the artistic collector the nobleman, when he was at last becoming almost established with important ecclesiastical commissions? This unholy non-Christian god revives the sexual 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 the painter's lover. A British visitor viewed the painting in about 1649 and was informed its subject has "the body & face of [Caravaggio's|his] own boy or assistant that slept with him". The identity of this boy was Francesco.

The painter had been deceased for about 40 years when this account was recorded.