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The young boy screams as his head is firmly gripped, a massive thumb pressing into his cheek as his parent's powerful palm holds him by the throat. This scene from The Sacrifice of Isaac visits the Uffizi Gallery, creating distress through the artist's chilling rendition of the suffering youth from the biblical narrative. It seems as if the patriarch, commanded by God to kill his son, could break his neck with a single turn. Yet the father's preferred approach involves the metallic steel blade he grips in his remaining palm, prepared to cut Isaac's neck. One certain aspect remains – whoever modeled as Isaac for this astonishing work displayed extraordinary acting skill. There exists not just fear, surprise and begging in his shadowed gaze but additionally deep grief that a protector could abandon him so completely.

The artist adopted a well-known scriptural tale and made it so vibrant and visceral that its terrors seemed to happen right in front of the viewer

Viewing before the artwork, viewers identify this as a actual face, an precise record of a young model, because the same youth – identifiable by his tousled hair and almost dark eyes – features in two additional works by Caravaggio. In every instance, that richly emotional face commands the composition. In John the Baptist, he peers mischievously from the shadows while embracing a lamb. In Victorious Cupid, he smirks with a hardness learned on Rome's alleys, his dark feathery wings demonic, a unclothed child running chaos in a well-to-do dwelling.

Victorious Cupid, presently exhibited at a British museum, constitutes one of the most embarrassing artworks ever created. Observers feel totally unsettled gazing at it. Cupid, whose arrows fill people with often painful desire, is shown as a very real, vividly illuminated unclothed form, straddling toppled-over objects that comprise musical devices, a music manuscript, metal armor and an architect's ruler. This heap of possessions resembles, intentionally, the mathematical and construction equipment scattered across the ground in the German master's engraving Melencolia I – save in this case, the melancholic mess is created by this smirking deity and the mayhem he can unleash.

"Love looks not with the vision, but with the mind, / And thus is feathered Love painted sightless," penned Shakespeare, just prior to this work was created around the early 1600s. But Caravaggio's god is not unseeing. He gazes straight at the observer. That face – sardonic and rosy-cheeked, staring with bold assurance as he struts naked – is the same one that screams in fear in Abraham's Test.

As the Italian master painted his multiple portrayals of the identical distinctive-looking kid in Rome at the start of the seventeenth century, he was the most celebrated religious artist in a city enflamed by religious renewal. Abraham's Offering demonstrates why he was commissioned to decorate sanctuaries: he could adopt a scriptural narrative that had been depicted many times before and render it so new, so raw and physical that the terror appeared to be occurring directly in front of you.

However there was a different aspect to Caravaggio, evident as soon as he came in Rome in the cold season that concluded 1592, as a artist in his early twenties with no teacher or patron in the city, only skill and audacity. Most of the works with which he captured the holy city's eye were anything but devout. What may be the very first hangs in London's National Gallery. A young man parts his crimson mouth in a scream of agony: while stretching out his dirty fingers for a fruit, he has instead been attacked. Youth Bitten by a Reptile is eroticism amid poverty: viewers can discern the painter's dismal chamber reflected in the cloudy waters of the glass container.

The adolescent sports a rose-colored flower in his coiffure – a symbol of the erotic trade in early modern painting. Venetian artists such as Tiziano and Jacopo Palma depicted courtesans holding flowers and, in a work destroyed in the WWII but documented through photographs, Caravaggio portrayed a famous woman prostitute, clutching a bouquet to her bosom. The meaning of all these botanical signifiers is clear: intimacy for purchase.

How are we to make of Caravaggio's sensual portrayals of boys – and of a particular boy in specific? 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 artist was neither the homosexual hero that, for instance, the filmmaker put on film in his twentieth-century movie Caravaggio, nor so entirely pious that, as certain art historians unbelievably assert, his Boy With a Basket of Fruit is in fact a portrait of Christ.

His initial paintings indeed offer explicit erotic implications, or including propositions. It's as if the painter, then a destitute youthful creator, identified with Rome's prostitutes, offering himself to live. In the Florentine gallery, with this idea in consideration, viewers might look to another early work, the 1596 masterpiece Bacchus, in which the deity of alcohol stares coolly at the spectator as he starts to undo the black ribbon of his robe.

A several annums following Bacchus, what could have motivated Caravaggio to paint Victorious Cupid for the art collector Vincenzo Giustiniani, when he was at last becoming almost respectable with important church projects? This profane pagan god revives the erotic challenges of his early paintings but in a more powerful, unsettling way. Half a century later, its hidden meaning seemed obvious: it was a portrait of Caravaggio's lover. A English visitor viewed Victorious Cupid in about the mid-seventeenth century and was informed its figure has "the body & face of [Caravaggio's|his] owne boy or assistant that laid with him". The name of this boy was Francesco.

The artist had been deceased for about 40 annums when this account was documented.