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The youthful boy cries out as his head is forcefully held, a massive digit digging into his cheek as his parent's powerful hand grasps him by the neck. This moment from Abraham's Sacrifice visits the Uffizi Gallery, creating unease through Caravaggio's harrowing portrayal of the suffering child from the biblical account. The painting appears as if the patriarch, commanded by the Divine to kill his son, could snap his spinal column with a single turn. Yet the father's chosen method involves the silvery steel knife he holds in his other hand, ready to slit the boy's throat. A certain element stands out – whoever modeled as the sacrifice for this breathtaking piece demonstrated extraordinary acting ability. Within exists not only dread, shock and pleading in his darkened eyes but also profound sorrow that a protector could betray him so utterly.

The artist adopted a familiar biblical tale and made it so fresh and raw that its horrors seemed to unfold right in front of you

Viewing in front of the artwork, observers identify this as a real face, an accurate depiction of a adolescent model, because the identical youth – identifiable by his tousled hair and nearly black pupils – features in several other works by Caravaggio. In each case, that highly expressive visage dominates the scene. In John the Baptist, he gazes playfully from the shadows while holding a lamb. In Amor Vincit Omnia, he smirks with a hardness acquired on the city's alleys, his dark feathery wings sinister, a unclothed adolescent creating chaos in a well-to-do residence.

Victorious Cupid, currently exhibited at a London gallery, constitutes one of the most discomfiting artworks ever painted. Viewers feel totally unsettled looking at it. The god of love, whose darts inspire people with frequently painful longing, is shown as a extremely tangible, vividly lit nude form, straddling toppled-over objects that comprise musical devices, a music score, metal armour and an builder's T-square. This pile of items echoes, deliberately, the geometric and construction equipment strewn across the floor in Albrecht Dürer's engraving Melencolia I – save here, the melancholic mess is created by this smirking deity and the mayhem he can release.

"Affection sees not with the eyes, but with the mind, / And therefore is winged Cupid painted blind," wrote Shakespeare, just before this painting was created around 1601. But the painter's Cupid is not unseeing. He stares straight at the observer. That countenance – sardonic and rosy-faced, staring with brazen assurance as he poses naked – is the identical one that screams in terror in The Sacrifice of Isaac.

As the Italian master created his multiple images of the same unusual-appearing kid in the Eternal City at the dawn of the seventeenth century, he was the highly acclaimed sacred painter in a city enflamed by Catholic revival. Abraham's Offering demonstrates why he was sought to decorate sanctuaries: he could take a biblical narrative that had been portrayed numerous occasions previously and render it so fresh, so unfiltered and physical that the horror seemed to be occurring immediately before you.

However there existed a different side to the artist, apparent as quickly as he arrived in Rome in the winter that concluded the sixteenth century, as a artist in his early 20s with no mentor or patron in the urban center, just skill and audacity. The majority of the works with which he caught the holy metropolis's eye were anything but holy. That could be the absolute first hangs in London's National Gallery. A young man parts his crimson lips in a yell of agony: while reaching out his filthy fingers for a fruit, he has rather been attacked. Boy Bitten By a Lizard is eroticism amid poverty: viewers can discern Caravaggio's gloomy chamber mirrored in the murky liquid of the transparent container.

The adolescent wears a rose-colored flower in his hair – a emblem of the sex trade in early modern art. Northern Italian painters such as Titian and Jacopo Palma portrayed prostitutes holding flowers and, in a work lost in the WWII but documented through images, the master portrayed a famous female prostitute, holding a bouquet to her bosom. The message of all these botanical indicators is obvious: sex for sale.

What are we to make of the artist's sensual depictions of boys – 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 truth is that the artist was neither the queer hero that, for instance, Derek Jarman put on screen in his 1986 film about the artist, nor so completely pious that, as certain art scholars improbably assert, his Boy With a Basket of Fruit is in fact a portrait of Christ.

His initial works indeed offer overt sexual suggestions, or even offers. It's as if Caravaggio, then a destitute youthful artist, identified with Rome's sex workers, selling himself to survive. In the Florentine gallery, with this thought in consideration, observers might turn to an additional initial work, the 1596 masterwork Bacchus, in which the god of alcohol stares calmly at you as he starts to untie the dark ribbon of his garment.

A few years following the wine deity, what could have driven the artist to paint Victorious Cupid for the artistic collector Vincenzo Giustiniani, when he was finally becoming nearly respectable with prestigious ecclesiastical projects? This unholy pagan god resurrects the sexual challenges of his early paintings but in a increasingly intense, unsettling manner. Half a century afterwards, its secret seemed clear: it was a portrait of the painter's companion. A English visitor saw Victorious Cupid in about the mid-seventeenth century and was informed its subject has "the body & face of [Caravaggio's|his] own youth or assistant that laid with him". The identity of this boy was Cecco.

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