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A young lad cries out as his head is forcefully gripped, a massive digit pressing into his cheek as his father's powerful hand holds him by the neck. This moment from The Sacrifice of Isaac visits the Uffizi Gallery, creating unease through the artist's chilling rendition of the suffering child from the scriptural account. It seems as if Abraham, instructed by the Divine to kill his son, could snap his neck with a single twist. However the father's preferred approach involves the silvery steel blade he holds in his remaining palm, prepared to cut the boy's neck. A definite element remains – whoever posed as the sacrifice for this astonishing work displayed extraordinary acting ability. Within exists not just dread, surprise and begging in his darkened gaze but additionally profound grief that a protector could betray him so utterly.

He took a well-known scriptural story and made it so fresh and raw that its terrors seemed to unfold directly in front of the viewer

Standing before the painting, observers recognize this as a actual countenance, an accurate record of a adolescent subject, because the same youth – recognizable by his disheveled locks and nearly black pupils – appears in several additional works by Caravaggio. In every instance, that richly expressive face commands the composition. In John the Baptist, he gazes playfully from the darkness while embracing a lamb. In Amor Vincit Omnia, he smirks with a hardness acquired on Rome's alleys, his black feathery appendages demonic, a unclothed child running riot in a well-to-do residence.

Amor Vincit Omnia, currently displayed at a London museum, constitutes one of the most embarrassing masterpieces ever painted. Viewers feel totally disoriented looking at it. The god of love, whose arrows inspire people with frequently painful longing, is portrayed as a very tangible, brightly illuminated nude figure, straddling toppled-over items that include musical instruments, a musical score, plate armor and an architect's T-square. This pile of possessions echoes, deliberately, the geometric and construction gear scattered across the ground in the German master's print Melancholy – except here, the melancholic disorder is created by this smirking Cupid and the turmoil he can unleash.

"Love sees not with the eyes, but with the mind, / And thus is winged Love depicted blind," penned the Bard, just prior to this work was produced around the early 1600s. But Caravaggio's god is not unseeing. He stares directly at the observer. That face – sardonic and ruddy-cheeked, looking with bold confidence as he struts naked – is the identical one that shrieks in fear in The Sacrifice of Isaac.

As the Italian master painted his multiple images of the same distinctive-looking kid in the Eternal City at the dawn of the seventeenth century, he was the most acclaimed sacred artist in a city enflamed by religious renewal. Abraham's Offering demonstrates why he was sought to decorate sanctuaries: he could adopt a biblical story that had been portrayed numerous occasions previously and make it so new, so raw and visceral that the terror seemed to be occurring immediately in front of you.

Yet there existed another aspect to Caravaggio, apparent as quickly as he came in Rome 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. The majority of the works with which he captured the sacred city's eye were anything but holy. That may be the very first resides in London's National Gallery. A youth opens his crimson lips in a yell of pain: while stretching out his dirty fingers for a cherry, he has rather been bitten. Youth Bitten by a Reptile is sensuality amid squalor: viewers can discern the painter's dismal room reflected in the murky liquid of the transparent container.

The adolescent wears a pink flower in his coiffure – a symbol of the erotic commerce in early modern art. Northern Italian painters such as Titian and Palma Vecchio portrayed prostitutes holding blooms and, in a painting destroyed in the WWII but documented through photographs, the master represented a renowned woman courtesan, clutching a bouquet to her chest. The message of all these floral signifiers is obvious: intimacy for sale.

What are we to make of the artist's erotic portrayals of boys – and of a particular adolescent in specific? It is a question that has split his interpreters ever since he gained mega-fame in the twentieth century. The complex historical truth is that the artist was not the queer hero that, for instance, Derek Jarman presented on film in his twentieth-century movie about the artist, nor so completely devout that, as some artistic scholars improbably assert, his Boy With a Basket of Fruit is actually a portrait of Jesus.

His initial paintings do offer overt sexual implications, or including offers. It's as if the painter, then a penniless youthful creator, identified with Rome's sex workers, offering himself to live. In the Uffizi, with this idea in mind, observers might look to an additional initial creation, the 1596 masterpiece the god of wine, in which the god of wine gazes coolly at the spectator as he begins to untie the black sash of his robe.

A several years after the wine deity, what could have driven Caravaggio to create Victorious Cupid for the artistic collector the nobleman, when he was at last growing almost respectable with important church commissions? This unholy pagan deity resurrects the sexual challenges of his initial works but in a increasingly powerful, unsettling way. Fifty years afterwards, its secret seemed clear: it was a representation of Caravaggio's lover. A British traveller saw Victorious Cupid in about 1649 and was told its subject has "the body & face of [Caravaggio's|his] own boy or servant that laid with him". The identity of this adolescent was Cecco.

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