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A youthful lad screams while his skull is forcefully gripped, a large digit digging into his face as his father's powerful palm grasps him by the neck. This moment from The Sacrifice of Isaac visits the Uffizi Gallery, evoking unease through Caravaggio's chilling rendition of the tormented child from the scriptural narrative. The painting appears as if the patriarch, instructed by God to sacrifice his son, could snap his spinal column with a single turn. However Abraham's chosen approach involves the silvery steel blade he grips in his other palm, ready to slit Isaac's throat. A certain aspect remains – whoever posed as Isaac for this breathtaking work demonstrated remarkable acting skill. There exists not just dread, shock and pleading in his darkened eyes but additionally deep sorrow that a guardian could abandon him so utterly.

He took a familiar scriptural story and made it so fresh and raw that its horrors appeared to happen right in view of you

Standing in front of the painting, observers identify this as a actual face, an accurate record of a adolescent subject, because the same boy – identifiable by his disheveled hair and nearly black pupils – appears in several other paintings by the master. In every case, that richly expressive visage dominates the composition. In Youth With a Ram, he peers mischievously from the darkness while holding a lamb. In Victorious Cupid, he grins with a hardness learned on Rome's streets, his dark feathery wings demonic, a unclothed child creating riot in a affluent residence.

Amor Vincit Omnia, presently displayed at a London museum, constitutes one of the most embarrassing artworks ever painted. Viewers feel totally disoriented gazing at it. Cupid, whose darts inspire people with frequently painful desire, is shown as a very tangible, vividly lit nude figure, standing over overturned objects that comprise stringed devices, a musical score, plate armor and an builder's ruler. This pile of possessions resembles, intentionally, the geometric and construction gear scattered across the ground in Albrecht Dürer's print Melancholy – except here, the gloomy mess is caused by this smirking Cupid and the turmoil he can release.

"Affection looks not with the vision, but with the soul, / And therefore is feathered Love depicted sightless," penned the Bard, just prior to this painting was produced around 1601. But Caravaggio's god is not unseeing. He gazes straight at the observer. That countenance – sardonic and rosy-faced, looking with bold assurance as he struts unclothed – is the identical one that shrieks in fear in Abraham's Test.

When the Italian master painted his three portrayals of the identical unusual-appearing youth in the Eternal City at the start of the 17th century, he was the highly celebrated religious artist in a city ignited by religious renewal. The Sacrifice of Isaac reveals why he was sought to adorn sanctuaries: he could adopt a scriptural narrative that had been portrayed many times before and make it so new, so raw and physical that the terror seemed to be occurring directly in front of the spectator.

Yet there was another side to the artist, evident as quickly as he came in Rome in the cold season that concluded 1592, as a painter in his early twenties with no teacher or patron in the urban center, just talent and boldness. Most of the works with which he captured the holy city's eye were anything but devout. That may be the very earliest hangs in London's National Gallery. A youth parts his crimson mouth in a yell of pain: while stretching out his filthy digits for a cherry, he has instead been bitten. Youth Bitten by a Reptile is eroticism amid poverty: observers can see the painter's dismal room reflected in the murky liquid of the glass container.

The adolescent wears a rose-colored flower in his hair – a emblem of the erotic commerce in Renaissance art. Venetian painters such as Titian and Jacopo Palma portrayed courtesans holding flowers and, in a painting destroyed in the second world war but known through photographs, Caravaggio portrayed a famous woman courtesan, clutching a bouquet to her chest. The meaning of all these botanical indicators is obvious: intimacy for sale.

What are we to make of the artist's erotic portrayals of youths – and of one boy in specific? It is a question that has split his commentators since he achieved mega-fame in the 1980s. The complicated historical truth is that the artist was neither the homosexual hero that, for example, the filmmaker presented on screen in his twentieth-century film about the artist, nor so entirely devout that, as certain artistic scholars unbelievably claim, his Youth Holding Fruit is in fact a portrait of Christ.

His early works indeed make explicit erotic implications, or including propositions. It's as if the painter, then a penniless young artist, identified with Rome's prostitutes, offering himself to survive. In the Florentine gallery, with this idea in mind, viewers might look to another early work, the sixteenth-century masterwork the god of wine, in which the deity of alcohol gazes calmly at you as he begins to undo the black ribbon of his robe.

A few years following the wine deity, what could have motivated Caravaggio to create Victorious Cupid for the artistic collector the nobleman, when he was at last becoming almost respectable with important ecclesiastical projects? This profane pagan deity revives the erotic challenges of his initial works but in a increasingly powerful, unsettling manner. Fifty years later, its secret seemed obvious: it was a portrait of the painter's lover. A English visitor viewed Victorious Cupid in about 1649 and was told its figure has "the physique and countenance of [Caravaggio's|his] owne boy or assistant that laid with him". The identity of this boy was Francesco.

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