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The youthful lad screams while his skull is forcefully held, a large digit digging into his cheek as his father's powerful palm holds him by the throat. That moment from The Sacrifice of Isaac appears in the Florentine museum, creating unease through Caravaggio's harrowing portrayal of the tormented child from the scriptural account. The painting seems as if the patriarch, instructed by the Divine to sacrifice his offspring, could break his spinal column with a single turn. Yet Abraham's chosen method involves the silvery steel blade he holds in his other hand, prepared to slit the boy's neck. One certain aspect stands out – whoever modeled as the sacrifice for this astonishing piece displayed remarkable expressive skill. There exists not only fear, shock and begging in his shadowed gaze but additionally profound grief that a guardian could betray him so completely.

The artist took a well-known scriptural tale and made it so vibrant and raw that its terrors appeared to unfold directly in front of you

Viewing in front of the painting, viewers recognize this as a real face, an precise depiction of a young model, because the identical youth – identifiable by his tousled locks and nearly black eyes – features in two other paintings by Caravaggio. In each case, that highly expressive visage dominates the scene. In John the Baptist, he gazes playfully from the darkness while embracing a lamb. In Amor Vincit Omnia, he smirks with a toughness learned on Rome's streets, his black plumed wings demonic, a naked adolescent creating chaos in a well-to-do residence.

Victorious Cupid, currently exhibited at a British museum, constitutes one of the most discomfiting artworks ever painted. Viewers feel totally unsettled looking at it. The god of love, whose arrows fill people with often painful longing, is portrayed as a extremely tangible, brightly lit unclothed form, standing over toppled-over items that comprise stringed devices, a musical score, metal armour and an builder's ruler. This heap of items resembles, deliberately, the geometric and construction gear strewn across the floor in Albrecht Dürer's print Melencolia I – except here, the melancholic mess is created by this grinning deity and the mayhem he can unleash.

"Love looks not with the eyes, but with the soul, / And therefore is feathered Cupid depicted sightless," wrote Shakespeare, shortly prior to this work was produced around the early 1600s. But the painter's Cupid is not unseeing. He stares directly at the observer. That face – sardonic and rosy-cheeked, looking with brazen confidence as he poses unclothed – is the same one that screams in terror in The Sacrifice of Isaac.

As Michelangelo Merisi da Caravaggio painted his three images of the same unusual-appearing youth in the Eternal City at the dawn of the seventeenth century, he was the highly celebrated religious painter in a metropolis ignited by religious revival. The Sacrifice of Isaac reveals why he was commissioned to decorate sanctuaries: he could take a biblical story that had been depicted many occasions before and make it so fresh, so unfiltered and visceral that the horror seemed to be occurring immediately before you.

However there existed a different aspect to Caravaggio, evident as soon as he arrived in Rome in the cold season that concluded the sixteenth century, as a artist in his initial twenties with no mentor or patron in the urban center, just skill and boldness. Most of the works with which he caught the sacred metropolis's attention were anything but devout. What could be the absolute earliest hangs in London's art museum. A young man parts his red mouth in a yell of pain: while reaching out his filthy digits for a cherry, he has instead been attacked. Boy Bitten By a Lizard is eroticism amid squalor: viewers can discern Caravaggio's dismal chamber reflected in the cloudy liquid of the glass container.

The adolescent sports a rose-colored flower in his hair – a symbol of the sex trade in Renaissance painting. Venetian artists such as Tiziano and Palma Vecchio portrayed prostitutes grasping flowers and, in a painting destroyed in the second world war but documented through images, Caravaggio represented a renowned woman courtesan, holding a posy to her bosom. The meaning of all these botanical signifiers is obvious: intimacy for sale.

What are we to interpret of Caravaggio's sensual depictions of youths – and of one boy in particular? It is a inquiry that has split his interpreters since he achieved widespread recognition in the twentieth century. The complicated past truth is that the artist was not the queer icon that, for example, the filmmaker put on film in his 1986 film about the artist, nor so completely devout that, as some artistic scholars improbably claim, his Boy With a Basket of Fruit is actually a portrait of Christ.

His initial paintings do make overt sexual suggestions, or even offers. It's as if Caravaggio, then a penniless youthful creator, aligned with the city's sex workers, selling himself to survive. In the Florentine gallery, with this thought in consideration, viewers might look to another early creation, the 1596 masterwork Bacchus, in which the god of alcohol stares calmly at you as he begins to untie the dark ribbon of his robe.

A few years following the wine deity, what could have motivated Caravaggio to paint Victorious Cupid for the art collector the nobleman, when he was at last growing nearly established with prestigious church commissions? This unholy non-Christian god resurrects the sexual provocations of his early paintings but in a more intense, unsettling manner. Half a century afterwards, its hidden meaning seemed obvious: it was a representation of Caravaggio's lover. A British traveller saw the painting in about the mid-seventeenth century and was informed its subject has "the body & face of [Caravaggio's|his] owne youth or servant that laid with him". The identity of this adolescent was Cecco.

The painter had been dead for about forty years when this story was documented.