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A young boy cries out while his head is firmly held, a massive digit pressing into his face as his parent's mighty hand holds him by the throat. This moment from Abraham's Sacrifice visits the Uffizi Gallery, evoking distress through Caravaggio's harrowing rendition of the suffering child from the biblical narrative. The painting seems as if Abraham, commanded by God to sacrifice his son, could break his neck with a single turn. However the father's preferred method involves the silvery steel blade he grips in his other hand, prepared to slit Isaac's neck. One certain aspect stands out – whoever posed as the sacrifice for this astonishing work demonstrated remarkable acting skill. Within exists not only dread, surprise and pleading in his shadowed eyes but also deep sorrow that a guardian could abandon him so utterly.

The artist adopted a well-known biblical tale and transformed it so fresh and visceral that its terrors appeared to happen directly in view of the viewer

Standing in front of the painting, observers recognize this as a real face, an accurate depiction of a young subject, because the identical youth – recognizable by his tousled hair and nearly dark eyes – appears in two additional paintings by the master. In every instance, that richly emotional face commands the scene. In John the Baptist, he gazes mischievously from the shadows while holding a lamb. In Victorious Cupid, he grins with a toughness learned on the city's streets, his black feathery wings demonic, a naked child running riot in a affluent dwelling.

Victorious Cupid, currently exhibited at a British gallery, represents one of the most discomfiting masterpieces ever created. Observers feel totally unsettled gazing at it. The god of love, whose darts fill people with frequently agonizing longing, is shown as a extremely tangible, brightly lit nude form, standing over toppled-over objects that include stringed instruments, a musical score, plate armour and an builder's T-square. This pile of items resembles, intentionally, the geometric and construction equipment scattered across the floor in the German master's engraving Melancholy – except in this case, the gloomy mess is caused by this smirking deity and the mayhem he can unleash.

"Love looks not with the vision, but with the mind, / And thus is winged Love painted blind," penned the Bard, shortly prior to this painting was created around the early 1600s. But Caravaggio's Cupid is not blind. He stares directly at the observer. That countenance – ironic and rosy-faced, staring with bold confidence as he struts unclothed – is the identical one that shrieks in terror in Abraham's Test.

As the Italian master created his multiple images of the same distinctive-looking youth in the Eternal City at the dawn of the 17th century, he was the highly acclaimed sacred painter in a metropolis ignited by religious renewal. The Sacrifice of Isaac reveals why he was commissioned to decorate sanctuaries: he could take a scriptural story that had been depicted numerous occasions before and make it so fresh, so raw and physical that the terror appeared to be occurring immediately in front of the spectator.

Yet there existed another side to the artist, apparent as quickly as he came in Rome in the cold season that concluded the sixteenth century, as a artist in his initial twenties with no teacher or supporter in the city, just skill and audacity. The majority of the paintings with which he caught the holy metropolis's eye were anything but devout. That could be the absolute earliest hangs in the UK's art museum. A young man opens his crimson lips in a yell of pain: while reaching out his filthy fingers for a cherry, he has rather been bitten. Youth Bitten by a Reptile is sensuality amid squalor: viewers can see Caravaggio's dismal room reflected in the cloudy waters of the glass container.

The boy sports a pink blossom in his coiffure – a symbol of the erotic trade in Renaissance painting. Northern Italian painters such as Tiziano and Palma Vecchio portrayed prostitutes grasping flowers and, in a painting destroyed in the second world war but known through images, Caravaggio represented a famous woman courtesan, clutching a bouquet to her chest. The message of all these floral indicators is obvious: sex for sale.

What are we to make of Caravaggio's sensual portrayals of youths – and of a particular boy in specific? It is a question that has split his interpreters ever since he gained mega-fame in the twentieth century. The complicated historical truth is that the artist was not the homosexual hero that, for example, Derek Jarman presented on film in his twentieth-century movie Caravaggio, nor so entirely pious that, as certain artistic historians improbably assert, his Youth Holding Fruit is in fact a likeness of Christ.

His initial paintings indeed offer explicit erotic suggestions, or including propositions. It's as if the painter, then a penniless youthful artist, aligned with Rome's prostitutes, selling himself to live. In the Uffizi, with this idea in consideration, observers might look to an additional initial work, the 1596 masterwork the god of wine, in which the god of wine stares calmly at you as he begins to untie the dark ribbon of his robe.

A few years following Bacchus, what could have driven Caravaggio to create Amor Vincit Omnia for the artistic patron Vincenzo Giustiniani, when he was finally growing nearly established with prestigious ecclesiastical commissions? This unholy non-Christian god revives the sexual provocations of his early works but in a increasingly powerful, unsettling manner. Fifty years afterwards, its secret seemed clear: it was a portrait of Caravaggio's companion. A British traveller viewed Victorious Cupid in about 1649 and was informed its figure has "the physique and countenance of [Caravaggio's|his] own youth or assistant that slept with him". The name of this boy was Cecco.

The painter had been deceased for about forty annums when this account was recorded.