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A young lad cries out while his head is forcefully held, a massive digit digging into his cheek as his father's mighty palm 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 suffering youth from the scriptural account. The painting appears as if Abraham, instructed by the Divine to kill his son, could snap his spinal column with a solitary turn. However the father's chosen approach involves the metallic grey knife he grips in his other palm, ready to slit Isaac's throat. A certain element remains – whomever modeled as Isaac for this astonishing work demonstrated remarkable expressive ability. Within exists not only fear, surprise and pleading in his shadowed eyes but also deep grief that a guardian could betray him so utterly.

He took a well-known scriptural story and made it so fresh and raw that its horrors appeared to happen directly in view of you

Standing before the artwork, viewers identify this as a real face, an accurate depiction of a young model, because the identical youth – recognizable by his tousled locks and nearly dark pupils – appears in several other paintings by the master. In every case, that richly expressive face dominates the scene. In Youth With a Ram, he gazes playfully from the shadows while embracing a ram. In Victorious Cupid, he grins with a hardness learned on Rome's streets, his black feathery appendages demonic, a naked child creating chaos in a well-to-do dwelling.

Victorious Cupid, presently exhibited at a London museum, represents one of the most discomfiting masterpieces ever created. Observers feel totally unsettled looking at it. Cupid, whose arrows inspire people with often agonizing longing, is shown as a very tangible, brightly illuminated unclothed figure, standing over toppled-over items that include musical instruments, a music score, metal armour and an architect's T-square. This heap of possessions resembles, deliberately, the geometric and construction equipment strewn across the ground in Albrecht Dürer's print Melencolia I – save in this case, the gloomy mess is caused by this smirking Cupid and the mayhem he can unleash.

"Love looks not with the eyes, but with the mind, / And thus is feathered Love depicted sightless," wrote the Bard, just prior to this work was created around the early 1600s. But the painter's god is not blind. He gazes straight at the observer. That face – ironic and ruddy-faced, staring with bold assurance as he poses naked – is the same one that screams in terror in The Sacrifice of Isaac.

When Michelangelo Merisi da Caravaggio painted his three images of the identical distinctive-looking kid in the Eternal City at the start of the 17th century, he was the highly acclaimed sacred painter in a metropolis ignited by religious revival. Abraham's Offering reveals why he was commissioned to decorate sanctuaries: he could take a biblical narrative that had been depicted many occasions previously and render it so fresh, so raw and visceral that the horror appeared to be happening directly before you.

Yet there was a different side to the artist, apparent as soon as he arrived in Rome in the winter that ended the sixteenth century, as a painter in his initial 20s with no mentor or patron in the urban center, just skill and boldness. Most of the works with which he captured the sacred metropolis's eye were anything but devout. That could be the absolute first resides in London's art museum. A youth parts his crimson mouth in a yell of pain: while stretching out his dirty digits for a cherry, he has rather been attacked. Boy Bitten By a Lizard is eroticism amid squalor: observers can see the painter's gloomy room reflected in the cloudy liquid of the transparent container.

The adolescent wears a rose-colored flower in his hair – a emblem of the erotic commerce in early modern painting. Venetian artists such as Tiziano and Jacopo Palma portrayed courtesans grasping blooms and, in a painting lost in the WWII but documented through photographs, the master portrayed a famous woman courtesan, holding a bouquet to her chest. The message of all these floral signifiers is clear: sex for purchase.

How are we to interpret of Caravaggio's erotic portrayals of youths – and of one adolescent in particular? It is a inquiry that has divided his commentators since he achieved widespread recognition in the twentieth century. The complex historical reality is that the artist was neither the homosexual icon that, for example, Derek Jarman put on screen in his twentieth-century film Caravaggio, nor so completely devout that, as certain art historians improbably assert, his Youth Holding Fruit is actually a likeness of Jesus.

His early works indeed offer overt sexual suggestions, or even offers. It's as if Caravaggio, then a destitute young artist, aligned with Rome's sex workers, offering himself to live. In the Uffizi, with this idea in consideration, observers might turn to an additional initial creation, the 1596 masterpiece the god of wine, in which the deity of alcohol stares calmly at the spectator as he starts to undo the black sash of his robe.

A several annums following the wine deity, what could have driven Caravaggio to create Victorious Cupid for the art patron the nobleman, when he was finally becoming almost respectable with important church projects? This profane non-Christian deity resurrects the erotic challenges of his initial paintings but in a increasingly powerful, unsettling way. Half a century afterwards, its secret seemed obvious: it was a representation of the painter's companion. A English traveller saw Victorious Cupid in about 1649 and was informed its figure has "the physique and countenance of [Caravaggio's|his] own boy or assistant that laid with him". The name of this adolescent was Francesco.

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