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The young boy cries out while his head is firmly gripped, a massive thumb pressing into his cheek as his father's powerful palm holds him by the neck. This scene from Abraham's Sacrifice appears in the Uffizi Gallery, creating unease through Caravaggio's chilling rendition of the tormented child from the scriptural narrative. The painting seems as if Abraham, instructed by God to kill his offspring, could snap his spinal column with a single turn. Yet the father's chosen approach involves the silvery steel knife he grips in his other palm, prepared to slit the boy's throat. A certain aspect remains – whoever posed as Isaac for this astonishing work displayed remarkable acting ability. Within exists not just fear, shock and pleading in his shadowed eyes but additionally profound sorrow that a protector could abandon him so utterly.

He adopted a familiar scriptural tale and made it so fresh and raw that its horrors appeared to happen directly in view of the viewer

Viewing before the painting, observers identify this as a actual countenance, an precise depiction of a adolescent model, because the identical youth – identifiable by his disheveled hair and nearly dark eyes – features in two other works by Caravaggio. In each instance, that highly emotional face commands the composition. In Youth With a Ram, he peers playfully from the shadows while holding a lamb. In Victorious Cupid, he smirks with a toughness acquired on the city's alleys, his black feathery appendages sinister, a naked child creating chaos in a affluent residence.

Victorious Cupid, presently displayed at a British museum, constitutes one of the most discomfiting artworks ever painted. Observers feel completely disoriented gazing at it. The god of love, whose darts inspire people with frequently painful longing, is portrayed as a extremely real, brightly illuminated nude form, straddling toppled-over items that comprise stringed instruments, a musical manuscript, plate armour and an builder's T-square. This pile of possessions resembles, deliberately, the geometric and architectural equipment scattered across the floor in the German master's print Melencolia I – save in this case, the gloomy mess is caused by this smirking Cupid and the turmoil he can unleash.

"Affection sees not with the vision, but with the mind, / And therefore is feathered Love painted blind," wrote Shakespeare, shortly before this painting was produced around the early 1600s. But the painter's Cupid is not blind. He stares directly at the observer. That countenance – ironic and rosy-faced, staring with bold confidence as he struts naked – is the identical one that shrieks in fear in Abraham's Test.

When the Italian master created his three images of the identical distinctive-looking 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 demonstrates why he was commissioned to decorate sanctuaries: he could adopt a biblical story that had been portrayed numerous times before and make it so fresh, so raw and physical that the horror appeared to be happening immediately before the spectator.

Yet there existed another side to the artist, apparent as quickly as he arrived in the capital in the winter that ended the sixteenth century, as a artist in his early twenties with no mentor or supporter in the urban center, just talent and boldness. The majority of the paintings with which he caught the holy metropolis's eye were anything but holy. That may be the absolute earliest resides in the UK's art museum. A youth opens his red lips in a yell of pain: while reaching out his dirty fingers for a cherry, he has rather been bitten. Youth Bitten by a Reptile is sensuality amid poverty: viewers can discern the painter's gloomy room mirrored in the cloudy liquid of the transparent container.

The adolescent sports a pink blossom in his hair – a emblem of the erotic trade in Renaissance painting. Venetian painters such as Titian and Palma Vecchio depicted prostitutes grasping blooms and, in a painting lost in the second world war but documented through photographs, the master portrayed a renowned female prostitute, clutching a bouquet to her bosom. The meaning of all these botanical signifiers is obvious: intimacy for sale.

What are we to interpret of Caravaggio's sensual depictions of youths – and of one adolescent in particular? It is a question that has split his interpreters ever since he achieved mega-fame in the twentieth century. The complicated historical reality is that the artist was not the homosexual hero that, for instance, Derek Jarman put on film in his twentieth-century film about the artist, nor so entirely pious that, as some art historians improbably claim, his Youth Holding Fruit is actually a portrait of Christ.

His early works indeed make overt sexual suggestions, or including offers. It's as if Caravaggio, then a penniless young artist, identified with the city's sex workers, selling himself to survive. In the Florentine gallery, with this thought in mind, observers might look to an additional early work, the sixteenth-century masterwork Bacchus, in which the god of alcohol stares calmly at the spectator as he starts to untie the black sash of his robe.

A several annums following Bacchus, what could have driven the artist to paint Victorious Cupid for the art patron the nobleman, when he was finally growing almost respectable with prestigious ecclesiastical commissions? This profane non-Christian deity revives the sexual challenges of his early works but in a more intense, unsettling manner. Half a century later, its hidden meaning seemed obvious: it was a portrait of the painter's lover. A English visitor saw the painting in about the mid-seventeenth century and was told its subject has "the physique and countenance of [Caravaggio's|his] own youth or assistant that slept with him". The identity of this boy was Francesco.

The painter had been dead for about 40 annums when this story was documented.