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The youthful lad cries out while his skull is forcefully gripped, a massive thumb pressing into his face as his parent's powerful hand grasps him by the throat. That moment from Abraham's Sacrifice appears in the Florentine museum, evoking distress through Caravaggio's harrowing portrayal of the suffering child from the scriptural narrative. It seems as if the patriarch, commanded by the Divine to kill his son, could snap his spinal column with a solitary turn. Yet Abraham's preferred approach involves the metallic steel blade he grips in his remaining palm, ready to cut Isaac's neck. A definite element stands out – whoever modeled as Isaac for this astonishing work displayed extraordinary expressive ability. There exists not only dread, shock and begging in his shadowed gaze but also profound sorrow that a protector could betray him so utterly.

The artist took a familiar scriptural story and transformed it so fresh and visceral that its horrors appeared to unfold directly in front of you

Viewing in front of the artwork, observers identify this as a actual countenance, an precise depiction of a young subject, because the identical boy – recognizable by his disheveled hair and almost dark pupils – features in two other paintings by Caravaggio. In every instance, that richly emotional face dominates the scene. In John the Baptist, he peers mischievously from the darkness while holding a ram. In Amor Vincit Omnia, he smirks with a hardness acquired on the city's alleys, his black feathery wings sinister, a unclothed adolescent creating riot in a affluent residence.

Victorious Cupid, currently exhibited at a British museum, constitutes one of the most embarrassing artworks ever painted. Observers feel completely disoriented looking at it. The god of love, whose arrows inspire people with frequently agonizing longing, is shown as a very real, vividly illuminated nude figure, straddling overturned objects that comprise stringed devices, a musical manuscript, metal armor and an architect's T-square. This heap of possessions echoes, deliberately, the mathematical and construction equipment strewn across the ground in Albrecht Dürer's print Melencolia I – save in this case, the melancholic disorder is created by this smirking Cupid and the turmoil he can unleash.

"Affection looks not with the vision, but with the soul, / And thus is feathered Cupid painted blind," penned Shakespeare, shortly prior to this work was created around 1601. But Caravaggio's Cupid is not blind. He stares directly at you. That countenance – ironic and rosy-faced, looking with brazen confidence as he struts unclothed – is the identical one that screams in fear in Abraham's Test.

As Michelangelo Merisi da Caravaggio painted his three portrayals of the same distinctive-appearing youth in the Eternal City at the dawn of the seventeenth century, he was the most celebrated religious painter in a city ignited by religious revival. Abraham's Offering demonstrates why he was sought to adorn sanctuaries: he could adopt a biblical narrative that had been depicted numerous times before and make it so fresh, so unfiltered and visceral that the terror seemed to be happening directly in front of the spectator.

Yet there existed another side to Caravaggio, apparent as quickly as he came in the capital in the cold season that ended 1592, as a artist in his early 20s with no teacher or patron in the urban center, just skill and boldness. Most of the works with which he caught the sacred city's attention were everything but devout. What could be the absolute earliest resides in London's art museum. A youth opens his crimson lips in a scream of agony: while reaching out his dirty fingers for a cherry, he has instead been attacked. Youth Bitten by a Reptile is sensuality amid squalor: observers can see the painter's dismal chamber mirrored in the murky waters of the glass vase.

The adolescent wears a pink blossom in his coiffure – a emblem of the sex trade in early modern painting. Venetian painters such as Tiziano and Jacopo Palma depicted courtesans holding blooms and, in a painting destroyed in the second world war but known through photographs, Caravaggio represented a renowned female prostitute, clutching a posy to her chest. The message of all these botanical signifiers is clear: sex for sale.

How are we to make of the artist's erotic portrayals of youths – and of a particular adolescent in specific? It is a inquiry that has divided his interpreters since he achieved mega-fame in the twentieth century. The complicated past reality is that the painter was neither the homosexual hero that, for instance, Derek Jarman presented on film in his twentieth-century film about the artist, nor so entirely pious that, as some art scholars improbably claim, his Youth Holding Fruit is in fact a likeness of Christ.

His early paintings indeed make explicit sexual suggestions, or including propositions. It's as if Caravaggio, then a destitute youthful creator, identified with Rome's prostitutes, selling himself to survive. In the Uffizi, with this thought in consideration, observers might look to another initial work, the 1596 masterwork the god of wine, in which the god of wine stares coolly at the spectator as he begins to untie the black sash of his robe.

A several years following the wine deity, what could have driven Caravaggio to paint Victorious Cupid for the art patron Vincenzo Giustiniani, when he was finally growing almost respectable with important church commissions? This unholy non-Christian god resurrects the sexual provocations 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 viewed Victorious Cupid in about 1649 and was informed its figure has "the body & face of [Caravaggio's|his] own youth or assistant that laid with him". The name of this adolescent was Cecco.

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