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A young boy screams while his skull is forcefully held, a massive digit digging into his cheek as his father's powerful hand holds him by the neck. This moment from Abraham's Sacrifice visits the Uffizi Gallery, evoking distress through Caravaggio's chilling rendition of the suffering child from the biblical narrative. The painting appears as if the patriarch, instructed by God to kill his offspring, could break his neck with a solitary twist. Yet Abraham's preferred approach involves the silvery grey blade he holds in his remaining hand, ready to cut Isaac's throat. A definite element stands out – whoever modeled as Isaac for this breathtaking piece demonstrated remarkable expressive skill. Within exists not only fear, shock and begging in his darkened eyes but also deep sorrow that a guardian could abandon him so utterly.

He took a well-known biblical story and made it so vibrant and raw that its terrors appeared to unfold right in front of the viewer

Viewing in front of the painting, observers recognize this as a real face, an accurate record of a young model, because the same boy – identifiable by his disheveled hair and almost dark pupils – appears in several additional paintings by Caravaggio. In each case, that highly expressive face commands the scene. In John the Baptist, he peers mischievously from the shadows while embracing a ram. In Victorious Cupid, he smirks with a hardness learned on the city's alleys, his black plumed wings demonic, a unclothed adolescent running chaos in a affluent residence.

Victorious Cupid, presently exhibited at a British museum, constitutes one of the most embarrassing masterpieces ever created. Observers feel totally unsettled looking at it. The god of love, whose arrows fill people with frequently agonizing desire, is portrayed as a extremely tangible, brightly illuminated nude figure, standing over overturned items that include stringed devices, a musical score, plate armor and an builder's T-square. This heap of items echoes, deliberately, the geometric and construction equipment scattered across the floor in the German master's print Melencolia I – save in this case, the melancholic disorder is created by this grinning Cupid and the mayhem he can release.

"Affection sees not with the eyes, but with the mind, / And therefore is feathered Cupid painted sightless," wrote Shakespeare, shortly before this painting was produced around the early 1600s. But Caravaggio's Cupid is not blind. He gazes straight at the observer. That countenance – sardonic and ruddy-cheeked, looking with brazen assurance as he struts unclothed – is the identical one that screams in fear in Abraham's Test.

When the Italian master created his three portrayals of the same unusual-looking youth in Rome at the start of the 17th century, he was the most celebrated sacred painter in a metropolis ignited by Catholic renewal. Abraham's Offering demonstrates why he was sought to decorate sanctuaries: he could take a scriptural narrative that had been depicted numerous occasions previously and render it so fresh, so unfiltered and visceral that the horror appeared to be happening directly before you.

Yet there was another side to Caravaggio, evident as quickly as he arrived in Rome in the cold season that concluded the sixteenth century, as a artist in his initial 20s with no teacher or supporter in the city, just skill and boldness. Most of the works with which he caught the holy city's eye were anything but holy. That may be the absolute first resides in the UK's art museum. A youth opens his crimson lips in a scream of agony: while reaching out his dirty fingers for a cherry, he has instead been bitten. Boy Bitten By a Lizard is eroticism amid squalor: viewers can discern Caravaggio's gloomy chamber mirrored in the cloudy waters of the transparent container.

The adolescent wears a pink blossom in his hair – a symbol of the erotic commerce in early modern art. Northern Italian artists such as Tiziano and Palma Vecchio depicted courtesans grasping flowers and, in a painting destroyed in the WWII but known through photographs, Caravaggio portrayed a famous woman prostitute, holding a bouquet to her chest. The meaning of all these botanical signifiers is clear: intimacy for sale.

How are we to make of the artist's sensual portrayals of youths – and of one boy in particular? It is a question that has divided his commentators ever since he achieved widespread recognition in the 1980s. The complex historical reality is that the artist was not the homosexual icon that, for example, the filmmaker presented on film in his twentieth-century movie Caravaggio, nor so completely pious that, as some art scholars unbelievably assert, his Youth Holding Fruit is actually a likeness of Jesus.

His initial paintings indeed make explicit erotic suggestions, or including propositions. It's as if Caravaggio, then a penniless young creator, aligned with Rome's prostitutes, offering himself to live. In the Uffizi, with this thought in mind, viewers might turn to an additional initial work, the sixteenth-century masterwork the god of wine, in which the god of alcohol gazes coolly at you as he begins to undo the dark sash of his robe.

A few years after the wine deity, what could have driven the artist to create Victorious Cupid for the artistic collector the nobleman, when he was finally becoming nearly respectable with important ecclesiastical commissions? This profane non-Christian deity revives the erotic challenges of his early works but in a more intense, uneasy manner. Half a century afterwards, its hidden meaning seemed obvious: it was a portrait of the painter's lover. A English traveller saw Victorious Cupid in about the mid-seventeenth century and was told its figure has "the body & face of [Caravaggio's|his] own youth or servant that laid with him". The identity of this adolescent was Cecco.

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