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The young boy cries out while his skull is firmly gripped, a large thumb pressing into his face as his parent's powerful palm grasps him by the neck. This moment from The Sacrifice of Isaac visits the Florentine museum, evoking distress through Caravaggio's harrowing portrayal of the tormented youth from the biblical narrative. It appears as if the patriarch, instructed by God to sacrifice his son, could snap his neck with a single turn. However the father's chosen approach involves the metallic steel knife he holds in his remaining palm, prepared to slit Isaac's neck. One definite element remains – whoever modeled as the sacrifice for this breathtaking piece displayed extraordinary acting ability. Within exists not only fear, shock and pleading in his shadowed gaze but also profound grief that a guardian could abandon him so completely.

He took a well-known scriptural story and made it so fresh and raw that its terrors appeared to unfold directly in front of the viewer

Standing before the painting, viewers recognize this as a actual face, an precise depiction of a young model, because the identical boy – recognizable by his disheveled locks and nearly dark pupils – features in several additional works by Caravaggio. In every instance, that highly emotional face dominates the composition. In Youth With a Ram, he gazes playfully from the shadows while holding a ram. In Amor Vincit Omnia, he smirks with a toughness acquired on the city's streets, his black plumed appendages sinister, a naked adolescent creating chaos in a affluent dwelling.

Amor Vincit Omnia, presently exhibited at a British museum, constitutes one of the most discomfiting masterpieces ever painted. Viewers feel completely unsettled looking at it. Cupid, whose arrows inspire people with frequently agonizing longing, is portrayed as a extremely tangible, brightly lit unclothed figure, straddling toppled-over objects that include musical instruments, a music score, metal armor and an architect's T-square. This pile of possessions echoes, intentionally, the mathematical and architectural equipment scattered across the ground in the German master's engraving Melancholy – save in this case, the melancholic mess is caused by this grinning Cupid and the turmoil he can release.

"Affection sees not with the vision, but with the mind, / And thus is winged Cupid painted blind," wrote the Bard, shortly prior to this work was produced around the early 1600s. But Caravaggio's Cupid is not blind. He gazes directly at you. That face – ironic and ruddy-cheeked, staring with brazen assurance as he poses naked – is the identical one that shrieks in terror in The Sacrifice of Isaac.

As the Italian master created his multiple images of the same unusual-looking kid in the Eternal City at the start of the 17th century, he was the highly celebrated religious artist in a metropolis ignited by Catholic renewal. Abraham's Offering reveals why he was sought to decorate sanctuaries: he could adopt a biblical narrative that had been depicted many occasions before and render it so fresh, so raw and visceral that the horror seemed to be occurring directly before the spectator.

Yet there was another aspect to Caravaggio, apparent as quickly as he arrived in Rome in the winter that concluded the sixteenth century, as a painter in his early twenties with no teacher or patron in the city, only skill and boldness. The majority of the works with which he captured the sacred city's eye were everything but holy. That could be the very first resides in the UK's art museum. A young man parts his red lips in a scream of agony: while stretching out his dirty fingers for a cherry, he has instead been bitten. Youth Bitten by a Reptile is sensuality amid poverty: observers can see the painter's gloomy room reflected in the murky liquid of the transparent container.

The boy wears a pink flower in his hair – a symbol of the sex trade in early modern painting. Northern Italian artists such as Tiziano and Palma Vecchio depicted prostitutes holding blooms and, in a work lost in the second world war but known through photographs, Caravaggio portrayed a renowned woman prostitute, holding a posy to her bosom. The message of all these floral signifiers is clear: intimacy for sale.

How are we to interpret of Caravaggio's erotic portrayals of youths – and of one boy in particular? It is a question that has split his interpreters since he achieved mega-fame in the twentieth century. The complex historical reality is that the artist was not the queer icon that, for example, Derek Jarman presented on screen in his twentieth-century film about the artist, nor so entirely devout that, as certain art scholars improbably assert, his Boy With a Basket of Fruit is in fact a likeness of Christ.

His initial works indeed offer explicit erotic suggestions, or including propositions. It's as if Caravaggio, then a destitute youthful creator, identified with Rome's prostitutes, offering himself to live. In the Florentine gallery, with this idea in mind, observers might turn to an additional initial work, the sixteenth-century masterpiece Bacchus, in which the god of wine stares coolly at the spectator as he begins to undo the dark ribbon of his robe.

A few years after the wine deity, what could have driven the artist to paint Victorious Cupid for the artistic patron the nobleman, when he was finally becoming nearly established with important ecclesiastical projects? This profane non-Christian god revives the erotic challenges of his initial paintings but in a increasingly powerful, uneasy way. Fifty years afterwards, its hidden meaning seemed obvious: it was a portrait of the painter's companion. A British visitor 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 servant that slept with him". The identity of this adolescent was Cecco.

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