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The youthful boy cries out as his head is firmly held, a massive thumb pressing into his face as his parent's powerful palm grasps him by the throat. That moment from Abraham's Sacrifice visits the Uffizi Gallery, evoking distress through Caravaggio's harrowing rendition of the tormented child from the scriptural account. It seems as if the patriarch, instructed by the Divine to kill his offspring, could break his neck with a single turn. Yet Abraham's chosen approach involves the metallic steel blade he holds in his other hand, ready to cut Isaac's throat. A certain element remains – whomever modeled as Isaac for this astonishing work displayed extraordinary expressive ability. Within exists not just dread, shock and pleading in his shadowed gaze but additionally deep grief that a guardian could betray him so utterly.

He adopted a well-known scriptural story and transformed it so vibrant and raw that its horrors seemed to unfold right in view of you

Standing before the artwork, viewers identify this as a real face, an accurate record of a young subject, because the identical boy – identifiable by his disheveled locks and almost black eyes – features in several additional paintings by the master. In each instance, that highly expressive visage commands the scene. In John the Baptist, he peers mischievously from the shadows while embracing a lamb. In Amor Vincit Omnia, he smirks with a toughness acquired on the city's alleys, his black plumed appendages demonic, a naked child running riot in a well-to-do residence.

Victorious Cupid, presently exhibited at a British gallery, constitutes one of the most embarrassing artworks ever created. Observers feel totally disoriented gazing at it. Cupid, whose darts fill people with often agonizing desire, is shown as a very real, brightly illuminated unclothed form, straddling toppled-over objects that include stringed instruments, a musical score, metal armour and an builder's T-square. This pile of items echoes, intentionally, the geometric and construction gear strewn across the ground in the German master's engraving Melancholy – except in this case, the melancholic mess is caused by this grinning Cupid and the turmoil he can release.

"Affection looks not with the vision, but with the soul, / And thus is winged Love painted blind," penned the Bard, shortly before this painting was created around the early 1600s. But the painter's god is not blind. He stares directly at you. That countenance – ironic and rosy-faced, staring with brazen assurance as he struts unclothed – is the identical one that shrieks in fear in The Sacrifice of Isaac.

When Michelangelo Merisi da Caravaggio painted his multiple images of the identical distinctive-appearing youth in Rome at the dawn of the 17th century, he was the most acclaimed sacred painter in a city enflamed by Catholic renewal. Abraham's Offering demonstrates why he was commissioned to adorn churches: he could adopt a biblical story that had been portrayed many times before and make it so new, so raw and physical that the horror seemed to be happening directly in front of you.

Yet there existed another side to Caravaggio, evident as quickly as he arrived in the capital in the cold season that concluded the sixteenth century, as a painter in his initial twenties with no mentor or patron in the city, just talent and audacity. Most of the paintings with which he caught the sacred metropolis's eye were everything but devout. That may be the absolute earliest resides in London's National Gallery. A youth parts his crimson mouth in a scream of pain: while stretching out his filthy digits for a fruit, he has rather been bitten. Boy Bitten By a Lizard is eroticism amid squalor: viewers can discern Caravaggio's gloomy chamber reflected in the murky liquid of the transparent container.

The boy wears a rose-colored flower in his coiffure – a symbol of the sex commerce in early modern art. Venetian artists such as Tiziano and Palma Vecchio portrayed prostitutes holding flowers and, in a work lost in the second world war but documented through photographs, Caravaggio portrayed a famous woman prostitute, clutching a posy to her bosom. The message of all these floral signifiers is obvious: intimacy for purchase.

How are we to interpret of the artist's sensual portrayals of youths – and of a particular boy in specific? It is a inquiry that has divided his interpreters ever since he gained widespread recognition in the twentieth century. The complex past truth is that the painter was not the queer hero that, for example, Derek Jarman presented on screen in his twentieth-century film Caravaggio, nor so entirely pious that, as some art scholars improbably assert, his Boy With a Basket of Fruit is in fact a portrait of Christ.

His initial works indeed make explicit sexual suggestions, or even offers. It's as if Caravaggio, then a penniless youthful artist, identified with the city's sex workers, selling himself to survive. In the Uffizi, with this idea in consideration, viewers might look to an additional initial work, the 1596 masterpiece the god of wine, in which the deity of alcohol stares calmly at the spectator as he begins to undo the dark ribbon of his robe.

A few annums after the wine deity, what could have driven the artist to create Victorious Cupid for the artistic collector Vincenzo Giustiniani, when he was finally becoming almost respectable with prestigious ecclesiastical projects? This profane non-Christian deity revives the erotic challenges of his early paintings but in a more intense, uneasy way. Fifty years later, its hidden meaning seemed obvious: it was a portrait of Caravaggio's companion. A English visitor saw Victorious Cupid in about 1649 and was told its figure has "the physique and countenance of [Caravaggio's|his] owne boy or servant that slept with him". The name of this adolescent was Francesco.

The painter had been dead for about forty years when this account was recorded.