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The youthful lad screams as his skull is forcefully held, a large thumb digging into his cheek as his parent's mighty hand holds him by the throat. That scene from Abraham's Sacrifice appears in the Uffizi Gallery, creating distress through the artist's chilling portrayal of the suffering child from the biblical account. The painting appears as if Abraham, instructed by God to sacrifice his son, could break his spinal column with a single twist. However the father's preferred approach involves the metallic grey knife he grips in his remaining palm, prepared to slit the boy's neck. One definite element stands out – whomever modeled as the sacrifice for this breathtaking piece demonstrated extraordinary expressive skill. Within exists not only dread, surprise and begging in his darkened eyes but also profound grief that a protector could betray him so utterly.

The artist took a well-known biblical tale and transformed it so fresh and raw that its terrors seemed to unfold directly in front of you

Viewing before the artwork, observers identify this as a actual face, an precise record of a adolescent subject, because the same youth – recognizable by his disheveled hair and almost dark eyes – appears in two additional works by the master. In each case, that highly expressive face commands the scene. In John the Baptist, he peers playfully from the darkness while embracing a lamb. In Amor Vincit Omnia, he grins with a toughness acquired on the city's alleys, his dark plumed appendages demonic, a naked adolescent running riot in a well-to-do residence.

Amor Vincit Omnia, presently displayed at a London museum, constitutes one of the most embarrassing masterpieces ever created. Viewers feel completely unsettled gazing at it. The god of love, whose darts inspire people with frequently painful desire, is shown as a very real, vividly lit nude figure, standing over overturned items that include stringed instruments, a musical score, plate armour and an architect's T-square. This heap of items resembles, intentionally, the geometric and construction equipment strewn across the floor in the German master's engraving Melancholy – save here, the melancholic mess is created by this grinning Cupid and the turmoil he can release.

"Affection sees not with the eyes, but with the soul, / And thus is feathered Love depicted sightless," wrote Shakespeare, shortly prior to this work was created around the early 1600s. But Caravaggio's Cupid is not unseeing. He gazes straight at you. That face – sardonic and ruddy-faced, staring with bold assurance as he poses unclothed – is the same one that screams in fear in Abraham's Test.

When Michelangelo Merisi da Caravaggio painted his three images of the same distinctive-appearing youth in Rome at the dawn of the 17th century, he was the highly acclaimed religious painter in a metropolis enflamed by Catholic revival. Abraham's Offering demonstrates why he was sought to adorn sanctuaries: he could adopt a biblical narrative that had been depicted numerous occasions previously and render it so new, so raw and visceral that the horror seemed to be occurring immediately in front of you.

Yet there existed another side to the artist, evident as quickly as he came in the capital in the winter that ended the sixteenth century, as a painter in his early twenties with no teacher or supporter in the urban center, just talent and boldness. The majority of the paintings with which he captured the sacred metropolis's eye were anything but devout. That could be the absolute first resides in London's National Gallery. A young man parts his crimson mouth in a yell of agony: while reaching out his dirty digits for a cherry, he has instead been attacked. Boy Bitten By a Lizard is eroticism amid poverty: viewers can discern Caravaggio's gloomy room reflected in the cloudy waters of the glass vase.

The boy wears a rose-colored blossom in his hair – a emblem of the sex trade in early modern art. Northern Italian artists such as Tiziano and Palma Vecchio portrayed prostitutes grasping blooms and, in a painting lost in the second world war but known through photographs, Caravaggio represented a famous female prostitute, clutching a bouquet to her chest. The message of all these floral signifiers is clear: intimacy for purchase.

How are we to interpret of Caravaggio's erotic portrayals of youths – and of a particular boy in particular? It is a inquiry that has split his interpreters ever since he gained mega-fame in the twentieth century. The complex historical reality is that the painter was neither the homosexual hero that, for instance, Derek Jarman put on film in his 1986 movie Caravaggio, nor so completely devout that, as certain art scholars improbably claim, his Youth Holding Fruit is in fact a portrait of Jesus.

His initial paintings indeed offer explicit sexual implications, or even offers. It's as if Caravaggio, then a destitute youthful artist, aligned with Rome's prostitutes, selling himself to live. In the Florentine gallery, with this idea in consideration, observers might turn to another initial creation, the sixteenth-century masterwork the god of wine, in which the deity of alcohol gazes calmly at you as he begins to untie the dark ribbon of his garment.

A several annums after the wine deity, what could have motivated the artist to create Amor Vincit Omnia for the art collector Vincenzo Giustiniani, when he was at last growing nearly established with prestigious church commissions? This unholy pagan god resurrects the sexual challenges of his initial paintings but in a more intense, unsettling manner. Fifty years afterwards, its hidden meaning seemed clear: it was a representation of the painter's companion. A English traveller viewed the painting in about the mid-seventeenth century and was informed its figure has "the physique and countenance of [Caravaggio's|his] owne boy or assistant that laid with him". The identity of this adolescent was Francesco.

The artist had been dead for about forty annums when this story was documented.