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The youthful lad screams as his skull is firmly held, a massive digit digging into his face as his father's mighty palm grasps him by the neck. This moment from The Sacrifice of Isaac appears in the Uffizi Gallery, creating unease through the artist's chilling portrayal of the suffering child from the scriptural narrative. It seems as if the patriarch, instructed by the Divine to sacrifice his offspring, could snap his spinal column with a solitary twist. Yet the father's preferred approach involves the silvery steel blade he grips in his other palm, ready to slit the boy's throat. One certain aspect stands out – whomever posed as the sacrifice for this astonishing piece demonstrated extraordinary expressive ability. There exists not just dread, shock and pleading in his shadowed gaze but additionally deep grief that a guardian could betray him so utterly.

He took a well-known biblical story and transformed it so fresh and raw that its horrors seemed to happen right in view of the viewer

Standing before the artwork, viewers recognize this as a real face, an accurate depiction of a adolescent model, because the identical boy – identifiable by his tousled locks and nearly dark eyes – appears in two additional works by the master. In each case, that highly expressive face dominates the composition. In Youth With a Ram, he peers mischievously from the shadows while embracing a lamb. In Amor Vincit Omnia, he smirks with a hardness learned on the city's streets, his black plumed appendages demonic, a unclothed child running chaos in a well-to-do residence.

Amor Vincit Omnia, currently displayed at a London museum, constitutes one of the most embarrassing masterpieces ever painted. Observers feel completely disoriented looking at it. Cupid, whose darts fill people with frequently painful desire, is portrayed as a very tangible, vividly illuminated nude form, standing over toppled-over items that comprise stringed instruments, a music manuscript, metal armor and an builder's T-square. This heap of possessions resembles, deliberately, the mathematical and architectural gear scattered across the ground in the German master's engraving Melancholy – except here, the gloomy mess is created by this smirking deity and the turmoil he can release.

"Affection sees not with the eyes, but with the soul, / And thus is winged Cupid painted blind," wrote the Bard, shortly before this work was produced around the early 1600s. But Caravaggio's Cupid is not blind. He gazes directly at the observer. That countenance – ironic and rosy-cheeked, looking with brazen confidence as he poses naked – is the same one that shrieks in terror in The Sacrifice of Isaac.

As the Italian master created his three images of the identical distinctive-appearing kid in Rome at the dawn of the 17th century, he was the highly acclaimed religious artist in a metropolis enflamed by Catholic renewal. The Sacrifice of Isaac reveals why he was commissioned to adorn sanctuaries: he could take a biblical story that had been depicted many times before and make it so new, so raw and visceral that the terror appeared to be occurring immediately before the spectator.

Yet there was another aspect to Caravaggio, apparent as quickly as he came in the capital in the cold season that concluded 1592, as a artist in his initial twenties with no teacher or supporter in the urban center, just skill and boldness. The majority of the works with which he captured the holy metropolis's attention were anything but holy. That could be the absolute earliest resides in London's National Gallery. A youth opens his red mouth in a yell of pain: while stretching out his filthy fingers for a cherry, he has rather been attacked. Boy Bitten By a Lizard is sensuality amid squalor: viewers can discern Caravaggio's gloomy chamber reflected in the murky waters of the transparent vase.

The boy wears a pink flower in his coiffure – a symbol of the erotic commerce in early modern art. Venetian painters such as Tiziano and Jacopo Palma depicted prostitutes grasping flowers and, in a work lost in the second world war but documented through images, the master portrayed a famous female courtesan, clutching a posy to her chest. The meaning of all these floral signifiers is clear: intimacy for purchase.

What are we to make of the artist's erotic depictions of boys – and of one adolescent in particular? It is a question that has divided his commentators ever since he achieved mega-fame in the 1980s. The complex past reality is that the artist was neither the homosexual icon that, for instance, Derek Jarman presented on screen in his twentieth-century movie Caravaggio, nor so completely devout that, as certain art historians improbably assert, his Boy With a Basket of Fruit is in fact a portrait of Jesus.

His early paintings do offer overt erotic implications, or even propositions. It's as if Caravaggio, then a destitute young artist, identified with Rome's sex workers, offering himself to live. In the Florentine gallery, with this idea in mind, viewers might look to another initial work, the sixteenth-century masterpiece the god of wine, in which the god of alcohol gazes calmly at you as he begins to untie the black ribbon of his garment.

A several annums after Bacchus, what could have driven the artist to paint Victorious Cupid for the art patron the nobleman, when he was finally growing nearly respectable with important church projects? This profane pagan deity resurrects the erotic challenges of his initial works but in a more powerful, uneasy way. Fifty years afterwards, its hidden meaning seemed clear: it was a portrait of the painter's companion. A British traveller viewed Victorious Cupid in about 1649 and was informed its figure has "the body & face of [Caravaggio's|his] own boy or assistant that slept with him". The name of this adolescent was Cecco.

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