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The young boy screams as his skull is firmly held, a massive digit digging into his cheek as his father's mighty hand holds him by the throat. This moment from The Sacrifice of Isaac appears in the Florentine museum, evoking distress through Caravaggio's chilling portrayal of the tormented youth from the scriptural account. It appears as if Abraham, commanded by God to kill his offspring, could snap his neck with a single twist. Yet the father's preferred method involves the silvery steel knife he holds in his other palm, prepared to slit the boy's throat. A definite element stands out – whomever posed as the sacrifice for this astonishing work displayed extraordinary expressive skill. Within exists not only fear, shock and begging in his shadowed eyes but additionally profound sorrow that a guardian could betray him so utterly.

The artist adopted a well-known biblical tale and made it so fresh and visceral that its horrors appeared to unfold right in front of you

Viewing in front of the artwork, observers recognize this as a actual countenance, an precise depiction of a adolescent subject, because the same boy – identifiable by his tousled locks and nearly black eyes – appears in two other works by the master. In every case, that highly emotional visage dominates the composition. In John the Baptist, he gazes playfully from the darkness while holding a ram. In Amor Vincit Omnia, he grins with a hardness acquired on the city's streets, his dark feathery appendages sinister, a unclothed adolescent creating riot in a affluent dwelling.

Victorious Cupid, currently displayed at a London gallery, constitutes one of the most embarrassing artworks ever created. Viewers feel completely unsettled gazing at it. Cupid, whose arrows fill people with frequently painful longing, is portrayed as a extremely tangible, brightly lit unclothed form, standing over toppled-over items that include stringed devices, a music manuscript, plate armor and an architect's T-square. This heap of possessions echoes, intentionally, the mathematical and construction gear strewn across the ground in the German master's print Melencolia I – except in this case, the melancholic disorder is caused by this smirking Cupid and the mayhem he can release.

"Love looks not with the eyes, but with the soul, / And thus is feathered Love depicted sightless," wrote the Bard, just prior to this painting was produced around the early 1600s. But the painter's Cupid is not unseeing. He stares straight at you. That face – ironic and ruddy-cheeked, staring with bold confidence as he struts naked – is the same one that shrieks in terror in The Sacrifice of Isaac.

When Michelangelo Merisi da Caravaggio painted his three portrayals of the identical unusual-appearing kid in Rome at the start of the seventeenth century, he was the highly acclaimed religious painter in a metropolis ignited by Catholic renewal. Abraham's Offering reveals why he was sought to adorn sanctuaries: he could take a biblical narrative that had been depicted numerous occasions previously and make it so new, so unfiltered and visceral that the horror seemed to be occurring immediately in front of the spectator.

Yet there existed another side to the artist, evident as soon as he arrived in the capital in the cold season that ended 1592, as a painter in his initial twenties with no teacher or patron in the city, just talent and audacity. The majority of the works with which he captured the sacred metropolis's attention were everything but devout. What may be the very earliest resides in London's art museum. A young man opens his crimson mouth in a yell of pain: while reaching out his dirty digits for a fruit, he has instead been bitten. Boy Bitten By a Lizard is sensuality amid poverty: observers can see Caravaggio's gloomy room reflected in the cloudy liquid of the glass container.

The adolescent wears a rose-colored blossom in his coiffure – a symbol of the erotic commerce in early modern painting. Northern Italian painters such as Tiziano and Jacopo Palma depicted prostitutes holding blooms and, in a painting destroyed in the second world war but known through images, Caravaggio represented a renowned female prostitute, holding a posy to her bosom. The message of all these floral indicators is obvious: intimacy for purchase.

What are we to interpret of the artist's erotic portrayals of boys – and of a particular adolescent in specific? It is a inquiry that has divided his commentators ever since he gained mega-fame in the 1980s. The complicated historical truth is that the painter was not the homosexual hero that, for example, the filmmaker put on film in his twentieth-century film Caravaggio, nor so completely devout that, as certain artistic historians improbably assert, his Boy With a Basket of Fruit is in fact a portrait of Christ.

His early paintings indeed offer explicit sexual suggestions, or even offers. It's as if Caravaggio, then a penniless youthful creator, identified with the city's prostitutes, offering himself to survive. In the Florentine gallery, with this thought in consideration, viewers might turn to another initial creation, the sixteenth-century masterwork Bacchus, in which the god of alcohol stares calmly at you as he starts to undo the dark sash of his robe.

A several annums following Bacchus, what could have motivated the artist to create Amor Vincit Omnia for the artistic collector Vincenzo Giustiniani, when he was finally growing nearly respectable with important ecclesiastical projects? This unholy non-Christian deity resurrects the sexual provocations of his early works but in a more powerful, unsettling way. Fifty years afterwards, its secret seemed obvious: it was a representation of the painter's lover. A British visitor viewed Victorious Cupid in about 1649 and was informed its subject has "the physique and countenance of [Caravaggio's|his] own youth or servant that slept with him". The identity of this adolescent was Cecco.

The painter had been dead for about forty annums when this account was documented.