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The youthful lad screams as his head is forcefully held, a massive digit digging into his cheek as his father's powerful hand holds him by the throat. This moment from The Sacrifice of Isaac visits the Uffizi Gallery, evoking unease through Caravaggio's harrowing portrayal of the suffering child from the biblical narrative. The painting seems as if Abraham, commanded by the Divine to sacrifice his offspring, could break his spinal column with a single twist. However the father's chosen approach involves the metallic grey blade he holds in his other palm, prepared to slit Isaac's throat. A certain element stands out – whomever posed as the sacrifice for this breathtaking work demonstrated extraordinary acting ability. Within exists not only dread, surprise and pleading in his shadowed eyes but also profound grief that a protector could abandon him so completely.

He took a familiar scriptural story and transformed it so vibrant and visceral that its terrors seemed to unfold right in front of the viewer

Standing before the artwork, viewers identify this as a actual face, an accurate depiction of a young model, because the identical youth – identifiable by his tousled hair and nearly dark pupils – appears in two additional paintings by the master. In each instance, that highly expressive visage dominates the scene. In Youth With a Ram, he peers mischievously from the shadows while embracing a ram. In Amor Vincit Omnia, he smirks with a toughness acquired on the city's alleys, his dark plumed wings sinister, a unclothed child running chaos in a affluent dwelling.

Victorious Cupid, presently displayed at a London gallery, constitutes one of the most discomfiting artworks ever created. Observers feel completely disoriented looking at it. Cupid, whose arrows inspire people with frequently painful desire, is shown as a extremely tangible, brightly illuminated nude form, standing over toppled-over items that comprise musical instruments, a music score, metal armor and an architect's T-square. This heap of items echoes, deliberately, the geometric and construction gear strewn across the ground in Albrecht Dürer's print Melencolia I – save here, the melancholic disorder is created by this grinning Cupid and the mayhem he can release.

"Affection looks not with the vision, but with the soul, / And therefore is winged Cupid painted blind," wrote Shakespeare, just prior to this work was produced around the early 1600s. But Caravaggio's Cupid is not blind. He stares directly at the observer. That countenance – ironic and rosy-cheeked, looking with brazen assurance as he poses unclothed – is the identical one that shrieks in fear in The Sacrifice of Isaac.

When Michelangelo Merisi da Caravaggio painted his three images of the same unusual-appearing kid in the Eternal City at the dawn of the 17th century, he was the most celebrated sacred painter in a metropolis enflamed by Catholic renewal. Abraham's Offering reveals why he was sought to adorn churches: he could take a scriptural narrative that had been portrayed numerous occasions previously and make it so fresh, so raw and physical that the horror appeared to be occurring directly in front of the spectator.

However there existed another aspect to Caravaggio, evident as soon as he came in the capital in the winter that ended the sixteenth century, as a artist in his initial twenties with no mentor or patron in the city, just skill and audacity. The majority of the paintings with which he caught the sacred metropolis's attention were anything but devout. What may be the very earliest resides in London's National Gallery. A young man opens his red lips in a scream of agony: while reaching out his filthy fingers for a cherry, he has rather been attacked. Youth Bitten by a Reptile is eroticism amid poverty: observers can see Caravaggio's dismal chamber mirrored in the cloudy waters of the glass vase.

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 Jacopo Palma depicted courtesans holding flowers and, in a work destroyed in the second world war but known through images, Caravaggio represented a famous female courtesan, clutching a bouquet to her chest. The message of all these floral signifiers is obvious: sex for purchase.

What are we to make of Caravaggio's erotic portrayals of youths – and of a particular boy in particular? It is a question that has divided his interpreters ever since he achieved widespread recognition in the 1980s. The complicated historical truth is that the artist was not the queer icon that, for instance, Derek Jarman presented on film in his twentieth-century film about the artist, nor so entirely pious that, as certain art historians unbelievably assert, his Youth Holding Fruit is actually a portrait of Christ.

His early paintings do offer explicit erotic implications, or including offers. It's as if the painter, then a destitute youthful creator, identified with the city's sex workers, selling himself to survive. In the Florentine gallery, with this idea in consideration, observers might look to another early work, the 1596 masterpiece the god of wine, in which the deity of wine stares calmly at the spectator as he begins to undo the black ribbon of his robe.

A few years after Bacchus, what could have motivated Caravaggio to create Victorious Cupid for the artistic collector Vincenzo Giustiniani, when he was at last growing almost respectable with important church projects? This unholy pagan god resurrects the sexual challenges of his initial paintings but in a increasingly intense, unsettling manner. Fifty years afterwards, its secret seemed obvious: it was a representation of Caravaggio's lover. A British visitor viewed Victorious Cupid in about the mid-seventeenth century and was informed its subject has "the physique and countenance of [Caravaggio's|his] owne youth or assistant that laid with him". The name of this boy was Cecco.

The painter had been deceased for about forty annums when this story was documented.