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A young boy screams as his skull is firmly gripped, a massive thumb pressing into his face as his parent's powerful hand grasps him by the neck. This scene from Abraham's Sacrifice visits the Uffizi Gallery, creating unease through Caravaggio's harrowing portrayal of the suffering child from the biblical narrative. It seems as if Abraham, instructed by God to kill his son, could snap his neck with a single turn. Yet the father's preferred method involves the silvery steel blade he grips in his remaining palm, prepared to slit the boy's neck. A definite element remains – whoever posed as Isaac for this astonishing work displayed remarkable expressive skill. There exists not only dread, surprise and begging in his darkened eyes but also profound grief that a protector could betray him so completely.

He adopted a familiar scriptural story and transformed it so vibrant and raw that its horrors seemed to unfold right in view of the viewer

Viewing in front of the artwork, viewers identify this as a actual face, an precise depiction of a adolescent model, because the identical boy – identifiable by his tousled hair and almost black pupils – features in two other works by the master. In each instance, that highly expressive visage dominates the scene. In John the Baptist, he gazes playfully from the darkness while holding a lamb. In Amor Vincit Omnia, he smirks with a toughness acquired on Rome's streets, his black plumed wings sinister, a naked child running riot in a well-to-do dwelling.

Victorious Cupid, presently displayed at a British gallery, constitutes one of the most discomfiting masterpieces ever painted. Viewers feel completely unsettled looking at it. Cupid, whose arrows inspire people with often agonizing longing, is portrayed as a extremely tangible, brightly illuminated nude form, straddling overturned objects that comprise stringed devices, a musical manuscript, metal armor and an architect's T-square. This heap of possessions resembles, intentionally, the geometric and architectural equipment strewn across the floor in the German master's engraving Melancholy – save in this case, the melancholic mess is caused by this grinning deity and the mayhem he can release.

"Love sees not with the eyes, but with the mind, / And therefore is feathered Cupid painted blind," wrote the Bard, shortly prior to this work was produced around 1601. But Caravaggio's Cupid is not unseeing. He gazes straight at the observer. That face – sardonic and ruddy-cheeked, staring with brazen confidence as he struts naked – is the identical one that screams in fear in The Sacrifice of Isaac.

As the Italian master created his three portrayals of the identical unusual-appearing youth in Rome at the start of the seventeenth century, he was the most acclaimed sacred painter in a city ignited by Catholic revival. The Sacrifice of Isaac reveals why he was commissioned to decorate churches: he could adopt a scriptural story that had been portrayed many times previously and render it so fresh, so raw and physical that the terror appeared to be occurring immediately in front of you.

However there existed a different side to the artist, evident as soon as he came in Rome in the winter that concluded the sixteenth century, as a artist in his early twenties with no mentor or patron in the city, just skill and audacity. The majority of the paintings with which he captured the sacred city's attention were anything but holy. That may be the very first hangs in the UK's National Gallery. A youth opens his crimson lips in a scream of agony: while stretching out his filthy digits for a fruit, he has rather been bitten. Boy Bitten By a Lizard is eroticism amid squalor: observers can discern the painter's gloomy room reflected in the cloudy liquid of the glass container.

The boy wears a pink blossom in his hair – a symbol of the erotic commerce in Renaissance painting. Northern Italian artists such as Tiziano and Palma Vecchio depicted courtesans holding blooms and, in a painting destroyed in the second world war but documented through photographs, Caravaggio portrayed a famous female prostitute, clutching a bouquet to her bosom. The meaning of all these floral indicators is clear: intimacy for sale.

What are we to make of the artist's erotic depictions of youths – and of a particular adolescent in specific? It is a question that has split his interpreters ever since he achieved widespread recognition in the twentieth century. The complex past reality is that the painter was neither the homosexual hero that, for example, Derek Jarman presented on film in his 1986 film about the artist, nor so completely pious that, as some artistic historians improbably claim, his Boy With a Basket of Fruit is in fact a likeness of Christ.

His initial paintings do make overt erotic suggestions, or even propositions. It's as if the painter, then a destitute young creator, identified with the city's prostitutes, selling himself to survive. In the Florentine gallery, with this thought in mind, viewers might look to an additional early work, the 1596 masterwork the god of wine, 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 driven the artist to paint Victorious Cupid for the artistic collector Vincenzo Giustiniani, when he was at last becoming nearly respectable with important ecclesiastical commissions? This unholy pagan god resurrects the sexual challenges of his initial paintings but in a more powerful, unsettling way. Half a century afterwards, its secret seemed obvious: it was a portrait of Caravaggio's lover. A English traveller viewed the painting in about the mid-seventeenth century and was informed its figure has "the body & face of [Caravaggio's|his] owne boy or servant that slept with him". The name of this boy was Francesco.

The artist had been deceased for about forty years when this account was documented.